This is a print version of story Alice 1 by ratty9uk from xHamster.com

Alice 1

Alice

My name is Alan Smith, I am twenty two, about five foot six, fairly slim at just nine stone, my hair is dark blonde and fairly long, sometimes I put it in a pony tail. I have a degree in computer science, I work for an I.T. company, travelling around the southern half of England fixing computers and programming. I live with my dad Greg in a quiet suburb in Essex. My mum Elizabeth left us about four years ago, that was such a surprise as mum and dad got on very well, there did not seem any reason for her to leave, but dad and I have got over our loss now. Dad belongs to a singles social club, he sometimes dates different ladies from his club. Me, well I occasionally get a chance to date the odd girl, but I am not into any commitment. When mum left us, dad moved into the other bedroom, he never moved any of mum’s things, I suppose he hoped she would return. When I was home alone I used to go in mums room as I called it, to become Alice, and dress up in mums clothes, as she was a flirty lady, her clothes were very sexy. I loved the mini dresses and silky underwear, most of her clothes fitted me perfectly even our shoe size was the same. I used to look forward to my time alone dressing up and feeling girly.
My work often called for me to stay in a motel or hotel for a night or two, when I knew I would be away, I always picked some clothes and get dressed up in my hotel room, I had never been outside when dressed up, I was a closet dresser, I was too scared to venture out in case I was found out.
I was due to travel to Gloucester for work, then down to Hampshire, two or three days away. It was early afternoon, dad was at work, I went to mums room with my case. Stripping off my clothes, I had decided to try on a few things that I would take with me. I put on my favourite panties, corselet with suspenders dark sheer stockings with strappy three inch heeled sandals, I was feeling good. Looking through the wardrobe, I picked a light summer mini dress, sat at the dressing table and applied a little makeup and lipstick, brushed and fluffed my hair. Standing front of the full length mirror, I took a critical look at myself, I could not fault my appearance, more than passable, I actually look bl**dy good, I wished I could pull a girl that good, I would fuck her brains out. I was getting extremely horny admiring the sexy girl looking back at me. I walked back and forward, the hem was three inches above the knee, I realised that if I was outside I would have to be careful if I bent or sat down or my stocking tops would be on display. I had got quite used to wearing heels, four years of practice in mums shoes had given me confidence. I proceeded to put various bits of clothing in my case, even a business suit that mum wore occasionally, I liked the formal female look it gave me, once I had sufficient for a few changes of clothes I got a small makeup bag with all the things I would need, packed all the girlie things. I went to my bedroom and packed enough boy things for my work. I had promised dad I would get dinner ready for us, I went down to the kitchen and prepared the meal, set the table. Looked at the clock and saw it was time to become Alan again. After returning all the clothes carefully to their proper place, I washed the makeup off, put an elastic band around my hair to make my usual ponytail, dressed in my scruffy boy clothes then checked myself in the mirror, all ok, I was back to being a normal computer nerd.
‘Hi Alan’ dad called as he came home
‘Hi dad, I’m in the kitchen’
As usual when he entered we had to go through the routine of a ‘High five’ as a greeting, it was something he liked to do to show his affection, a sort of ‘dad-son’ thing.
‘Mmm, dinner smells good’
‘Nearly ready dad, about five minutes’
Dad was an office supervisor, working in a large London office, many years ago he saw the potential of the computer, he groomed me and sent me to technical colleges and pushed me until I had a degree in computer science. Any new innovation that came along in that field, he sent me on the course to study it. I had many diplomas for different aspects in the IT industry. As my work takes me into highly sensitive and secure areas, I had a pass card and identity badge, these contained everything about me, age, height, hair colour, bl**d group, iris recognition data, even my DNA profile, a little while ago I made an exact copy of these except they had me as Alice Smith, female, even the coded picture was me as Alice, I knew they would pass even the toughest scrutiny, I had even added Alice in the main data base as my twin s****r.
I put the dinner on the plates
‘Smells good son’ he said as he entered ‘you will make a great housewife for someone one day’
‘Yeah, and pigs might fly’ I grinned.
Dad and I didn’t get a lot of time together, what with his work and social life, and my work as well, so when we did get the opportunity we had a good chat, this was one of those times. We finished our meal, I washed up the dishes then dad got a couple of beers from the fridge. I don’t drink much, I like to be in control of my actions, so I declined the second one he offered.
‘Sorry dad, I have to be up early and I have a long drive tomorrow, I will be away for three or four days’
‘You take care Alan, you are the only one I have left in this f****y’
‘I will dad, goodnight’
We high fived as I left for bed.
The next day I pulled in to the motel in Gloucester, I was a bit weary after the three-hour drive, I had left home at five am. At eight thirty after checking in and unloading my suitcase and tool case in my room, I sat in the diner area and had a nice breakfast. Back in my room I phoned the client to say I would be on site around nine thirty. I arrived on site went through the security having my pass and badge scanned. I was introduced to the office manager, who then explained their problems. I set to work. Whilst going through the breakdown procedures for fault finding, I realised that ninety five percent of my work I was by myself, with very little contact with any of the other employees. I thought if it was not a regular customer, I could get away with attending a site as my alter ego, and as the next customer was down in Hampshire and they were a one off call the day after tomorrow, I got excited at the thought of going as a girl. I’ll try it, just the once, to see how it feels to be out in girl clothes. I had a light lunch in the canteen, again with no interaction with the employees except at the coffee machine when some man told me to go first as he was getting several for his table, I thanked him, drank my coffee and set back to work. At five pm, I reported to the office manager and told him everything was going well and should be finished tomorrow.
On the way back to the motel I popped in an off licence and bought a bottle of wine, I would have a couple of glasses to celebrate my decision to go girlie on the next call. Back in my room I stripped and showered, put on my corselet stockings and panties, then covered them over with my boy clothes, then went to my evening meal at the motel diner. I could feel the silky underwear on my skin every move I made, I was feeling very horny. I sat eating my meal when…
‘Hello’
I jumped, my chair went flying and I finished up on the floor.
‘I am so sorry’ a young pretty blonde girl said as she helped me up, ‘I didn’t mean to startle you, I am really sorry’
‘That’s ok, I don’t think I broke anything’ I muttered
‘I came over to tell you that when you get dressed you should make sure the curtains are pulled’ she grinned as she sat opposite me ‘Oh, and by the way, I love your sexy underwear’.
I looked down at my hands, my face turned crimson, I sat there hoping a hole would appear and swallow me up.
‘Please don’t feel embarrassed, you see I am a male too’
I looked up at her startled, she was a very attractive blonde girl, pretty face and lips I could kiss forever, I could not see her figure at the angle I was sitting.
‘You are very pretty’ I said awkwardly
‘Thank you, I think you will make a great looking girl too. Now finish your meal then we can talk’
I had gone off my food and just pecked at the remains
‘Come’ she said standing and holding her hand out for me, ‘let’s go and talk’.
I held her hand, it felt warm and soft, she was wearing a sleeved cotton dress, three inch heels nicely shaped nylon covered legs.
‘Where are we going’ I asked.
‘To your room so you can take off those boy clothes and get into proper clothes. I gather you have a dress with you. By the way, I’m Carol’
‘Alan or Alice’ I offered
I let us into my room, I was nervous, nobody had ever seen me in girl clothes.
‘Can I see what clothes you have’?
I showed her what I had brought with me.
‘Oh, please wear this one Alice’ she said holding up my cotton mini dress ‘it looks so much like the one I am wearing’
I took the dress and went into the bathroom and changed into the dress and shoes, I shook my hair out from the ponytail and fluffed it out. I was shaking as I stepped back in the room.
‘Wow, who’s a good looking chick then’?
she stepped up to me moved the odd stray hair from my face, I was so near to that pretty face and those luscious lips.
‘Why are you shaking Alice, is this your first time being seen’?
‘Yes Carol, you are the first’
‘Darling how sweet’
She leaned forward and kissed me on my lips, I put my arms around her and kissed her back, we began using tongues, after what seemed like an age, we parted lips, we were both out of breath.
‘I have wanted to do that ever since I fell on the floor, your lips looked so inviting’ I smiled at her.
‘I wanted to hold you ever since I saw you in underwear’ she giggled ‘now lets get your makeup on and I can repair mine, we have lots to talk about’.
I sat in front of the mirror, and applied my makeup, and brushed my hair.
‘You look fantastic Alice’ she said touching up her lippy.
‘I thought you were a real girl, you are very pretty’ I said ‘would you like some wine’
‘Yes please, have you any glasses’?
‘Only those in the bathroom, I wasn’t expecting visitors’
Sitting side by side on the bed, we started chatting and sipping the wine.
‘How long have you been dressing’
‘Since my mum left four years ago’
‘I have been doing it since I was twelve, I am now twenty four, and I love it. Have you ever wanted to go out when dressed’?
‘Yes, I decided today to try it just once, the day after tomorrow at my work’ I went on to explain my job, and how I don’t have much interaction with other people, and how nervous I felt about it.
‘I have been going out dressed for years, never where I live, I travel from my home in Oxford to motels well away from my area, and spend a few days as a girl, I never go out with anyone except a friend who also dresses, I met her online and we meet up from time to time, we go shopping sometimes’
‘Do you like real girls’ I queried
‘You mean am I heterosexual? well sort of , I like pretty girls whether they are cross dressers like us, or real ones’
‘When I first saw you, I thought you were a real girl, I fancied you, I thought you were sexy’ I said
‘Do you find me sexy now’?
‘Yes’ I admitted
‘Would you fuck me, given the chance’? Carol asked
I blushed again, I looked down at my nylon clad legs.
‘Yes’ I stammered ‘but only when you are dressed as a girl’
‘I feel the same, I would love to fuck you, I think you are very attractive’
I knew in my heart that I wanted her, I had been horny all day, and to have this pretty girl beside me was driving me nuts, and it seems she feels the same, I was a bit concerned about having to take her dick in me, but I really wanted to fuck her badly. The wine had loosened my normal feelings and I was prepared to lose my so called virginity so that I could have her.
‘Carol? Would you teach me’?
‘Oh Alice, darling, I would love to’
with that she put her arms around me and we started kissing again, but this time more passionately. She was caressing my leg with her hand, above the stocking top, she reached my panties grasped my dick and gave it a squeeze.
‘I want you to make love to me first, it will help to relax you, but first we have to prepare ourselves, I will nip back to my room and get a douche, it will make it so much nicer’ she left for her room and returned holding a small case.
‘Have you ever used one of these’? She asked
‘No, please would you show me how’
She lifted my dress up and hooked her fingers in the waistband and eased my panties down, I had to raise my bottom to assist her. I was embarrassed knowing she was looking at my dick.
‘Nice size, I will look forward to it’ she grinned
She lifted her dress, I was once again shaking as I lowered her panties down. Her dick popped out, it was around the same size as mine, about six and a half inches, it was shaved smooth, I felt I would like to kiss it.
‘By using this douche, it will stretch your anal tube and leave you squeaky clean inside, now bend over and I will put the tube in and fill you with warm soapy water, just try to hold it all inside for a few minutes, then we do it again twice more’
Carol filled the bag with warm water and put the tube into my bottom, it felt strange having it pushed in me, then she squeezed the bag, I could feel the water going deep inside me filling me up, it was very uncomfortable.
‘Now hold your bottom tight to hold it in’
I felt I was bursting and desperately wanting let it out, I could feel the gurgling of water sloshing about.
‘Now sit on the loo, but hold it in a little longer’
‘It is getting painful Carol, please can I go’?
‘Oh, ok then, as it’s your first time’
The relief as I opened my bowels was great, I finished and wiped myself clean, Carol then bent me over, pushed the tube back in and refilled me. The pain was not so intense now, the second flushing through made me feel empty, she added some oily stuff with the next load, and explained it would lubricate my insides. After the last filling and emptying, I washed myself, I felt so clean and comfortable inside. Carol then proceeded to wash out herself and cleaned up, we both jumped under the shower and very slowly and sexily washed us both down, then she grasped my hand and led me back into the bedroom. We both dressed in sexy underwear, and put on makeup, we held each other close and gazed in each other’s eyes, she smiled as she asked
‘Are you ready darling Alice’?
‘Yes, I think so’ I whispered nervously
She picked up her purse and produced a tube of KY lubricant, squeezing some on her fingers she then ran them all over my dick, she turned over and got on all fours on the bed.
‘You have to put some in my bottom now’
and passed the tube to me, I squeezed some on my fingers
‘Use one finger first and push some inside me, then start using two fingers and get some deep inside me’
I saw her puckered anus, I didn’t think I would get my dick in such a tiny hole. I pushed my lubed finger at her entrance and it popped in, she felt so warm.
‘Ooohh, now work the jelly all around in there’
I carried on, then added my second finger, working them right to my knuckles.
‘Now Alice, now is the time to fuck me, just go slowly’
I wanted her so much, my dick was the hardest it had ever been, I held my stiff dick to her hole, and gently pushed into her, the head of my dick popped in and was clutched tightly by her anal ring,
‘Oh Carol, you feel wonderful’ I said.
Easing slowly into her, feeling the tightness of her rectal tube gripping my dick, I finally got all in her, and began fucking in and out, she felt wonderful, I was finally fucking this pretty girl, she felt much nicer than a real girl, I was holding her by her hips as I gently slid in and out of her beautiful tight bottom, she was rocking in time with my thrusts, I was loving it. I carried on, I could feel my balls tightening I knew I could not last long.
‘Carol? Would you like me to pull out’
‘No, Alice darling, I want you to cum in me’
I pushed in as deep as I could, my dick pulsed and erupted as I pumped my seed deep inside, I cum so hard I could see stars. I rested with my dick in her, I was breathing hard, I so enjoyed that fuck. My dick was wilting and finally dropped out, she handed me some tissues.
‘Well, Alice, how do you feel’? she said rolling onto her back and looking up to me.
‘Fantastic, I think you are the best fuck I have ever had’
I looked at her sweet face, smiling at me, I could easily fall for her.
‘See this’? she said waving her hard dick at me ‘it wants you badly’
I knew the time had come for me to experience being fucked, although I was worried about my first time, I still wanted to give myself to her.
As I assumed the position on my hands and knees, I realised I actually wanted her to fuck me.
She kneeled beside me and spread the KY over her dick, then went behind me, I felt her finger at my anus, I jumped as it entered me
‘Don’t worry darling, I will be very gentle with you, just try to relax’
I could feel her finger loosening my ring, the second finger went in, it hurt a bit at first, then as I relaxed the pain went and her fingers were deep in me.
‘Now is the time Alice darling’
I felt pain as her knob entered me, but I knew it would gradually go, very slowly she entered me deeper and deeper, I had a sort of burning sensation and pain, I felt so full, her thighs touched the back of my legs, I knew she was fully in me now, she began little fucking motions in and out, the pain was gone and now I could feel her sliding smoothly inside me. I was being fucked like a girl, I hated to admit it, but it was now feeling good, I liked the feeling of her dick inside me, I backed up to her as she went forward, we got into a rhythm. I have now given my virginity to this lovely Carol, I am so pleased, I was enjoying being fucked by her.
‘Do you want me to pull out darling’
‘No Carol, I want it in me, I want to be yours completely’
I felt her begin to swell inside me, I could swear I felt her sperm travel up her dick then flooding my bowels with her essence. I was a girl now, her girl, I was dressed like one, I felt like one, and just been fucked like one, and I loved it.
‘Thank you so much Alice, you have given me your virginity, you were so tight at first, a bit more loose now though’ she giggled ‘how do you feel’
‘Wonderful, I feel so girlie, and you make such a good lover’
‘Well, I think I should give you another new experience’ how about straightening ourselves up and walk to the late night shop just up the road and get another bottle of wine, it’s only a hundred yards’
‘I have never been out before as a girl’
‘We will be together’
‘Ok’
‘Leave your panties off and keep your bottom clenched’
We fixed our makeup, got dressed, I put the key in her purse, and we went out. I was holding her hand tightly. After walking about half way, I began to enjoy the freedom and the clip clop of our heels, the swish of my dress, and the feel of nylon sliding on my legs.
We reached the shop, a sort of mini market, I found the wine while Carol was looking around. We met at the cashier’s desk, Carol was holding another purse. After paying, Carol handed me the new purse.
‘Here Alice, a little present to remember this day’
I gave her a big kiss on her lips
‘Thank you Carol, I will never forget today, you have changed my life, I feel so much more confident now’
We held hands on the way back, I felt a trickle run down my leg, ‘oops’ I thought, that is her cum, I giggled
‘What’s funny girlfriend’?
‘My bum is leaking’
we both laughed out loud
‘Come on gorgeous, I want to refill it again’
Once back in the room, we hugged and kissed passionately, I reached behind her and slowly unzipped her dress, we broke the kiss, she shrugged it down to reveal her silky underwear, she stepped out of her fallen dress on the floor, she stood in front of me in her bra and suspenders, if it wasn’t for her dick sticking out from her body, she would be a very sexy girl. I wanted to fuck her again, but I also wanted to be fucked by this lovely creature. She helped me out of my dress, as we got close for another clinch, our dicks rubbed together, we both looked down and giggled, I held hers and she held mine. She looked me in the eyes and whispered
‘Can I fuck you first this time, I do want you so badly’
‘I am all yours darling Carol, I loved you fucking me, I want to feel you in me again’.
‘Lay on your back and put the pillows under you, I am going to make love to you missionary style’
I got into position, she squeezed some KY and lubed us up, she lifted my nylon clad legs to her shoulders, I looked up at her pretty face as she pushed her dick gently into me. I hardly felt any pain while she fed more of her dick into me. That nice feeling of fullness as her thighs touched the back of my legs, then she began fucking me with long slow strokes. She smiled down to me
‘Alice darling, I am in heaven, you are such a beautiful girl and I am fucking you, I could easily fall in love with you’
‘I feel the same way Carol, you are a pretty girl and sliding deep in me, making love to me, I never dreamed it would be like this’
Slap slap as her thighs met my buttocks, slurp slurp as her dick slid in and out, I was being well and truly fucked, her movements began speeding up, she was grunting as she fucked harder, her dick was swelling, then I really did feel the throbbing of her dick as it unloaded her sperm deep inside me. It felt so good and I had satisfied my lover. After she started to wilt in me, she leaned forward and kissed me hard.
‘Alice darling, I am falling in love with you, I can’t help it, I have never felt this way before’
‘I feel the same Carol, you are the best thing that has ever happened to me’
Her dick plopped out, we quickly used tissues to clean each other.
‘Now Alice’ she said grasping my hard dick ‘it’s my turn to be on the receiving end, I want this inside me’.
We exchanged places, I used the KY then I lifted her legs to my shoulders, her nylon clad legs felt so good against my neck, I placed my dick and eased into her warm inviting body. Gazing in her eyes I went gently fully into her, she smiled back.
‘Mmm, I love being inside your body’ I whispered
I began fucking this sweet girl, I ran my hands up and down her silky legs, I stroked her limp dick and cupped her now empty balls, I had never known anyone as intimately as this before. I was fucking her for what seemed like ages, I was enjoying every second, she seemed to try and draw me in with a sort of gripping with her anus.
‘Do you like that darling’? she said ‘I am trying to milk your lovely dick with my bottom’
‘Mmm, feels so nice, you will have to teach me that’
I picked up the pace, my balls were aching for release
‘Oh Carol darling, ugh I’m cumming, ugh so deep, ugh in you’
I grabbed some tissues, as I leaned to kiss her my dick plopped out, I wiped us both clean.
‘God, that was fantastic, you are the best fuck ever, far better than a real girl’ I said as I lay on top of her, kissing her face all over.
The next thing I knew, I woke up with a start, my left arm had pins and needles, I looked over, and a warm glow came over me as I recognised Carol beside me. I had only met her yesterday, but we had fucked each other twice, I had given my virginity willingly to a pretty transvestite. I looked at the clock, nearly six. I eased my arm from under her, then quietly crept to the bathroom, my bum was a bit sore and was a bit crusted with dried cum, I ran the shower, removed the rest of my clothes and got under the warm spray, I soaped myself over and was bending to wash my legs and feet,
‘Gotcha’
I was suddenly startled when something touched my bum, I slipped and sat down hard on the tiled floor, I looked up to see Carol grinning at me
‘You frightened the life out of me, you cow’ I grinned back ‘please help me up’
We stood face to face, our makeup ruined and running down, we kissed and held each other tight under the warm water, both our limp dicks dangling together.
‘Please can I soap you’ I asked
She stood with her legs apart as, run my soapy hands all over her
‘What a nice shaped bum you have’
‘You should know, you have been in there enough’ she said laughing
‘It feels nice too’ I said cupping her buttocks in my hands.
‘Are you feeling horny this morning Alice’?
‘Well..yes’
‘I will only do it if you wear some girlie underwear, at least, and also some makeup, I did say I am sort of heterosexual, I don’t fancy men at all’
‘That, I must agree with you, I met a very sexy blonde girl yesterday, and yes, it was because she was girlie that I wanted her’
‘Ok cutie, let’s get it together then lets get together’ by the way she asked ‘what time do you have to be at work’?
‘Around nine fifteen, only two miles from here’ I answered
we put on stockings, bra and padded them out, I loaned her a baby doll top, I put on my corselet, both shared the mirror and added our makeup, both of us giggling like silly schoolgirls. We looked at each other up and down, both our dicks erect with anticipation.
‘I will be bottom first Alice’ as she lay on the bed ‘do you want me this way or on my knees’?
‘This way, so I can stroke your legs and see your pretty face while I make love to you’
She put the pillows under her and passed me the KY, once I had prepared us I looked down, she was so pretty in her baby doll top, she smiled as I eased into her,
‘Mmm, you look and feel so good’
‘How does this feel, my sexy girl’?
I could feel my dick being squeezed and drawn into her,
‘That feels wonderful, you will have to teach me how to do it’
‘You have pull your insides as if you were trying draw in the dick and squeeze your anus at the same time’ Carol murmured.
‘If you carry on doing that, I won’t be able to hold back’ I croaked
‘C’mon baby, fill me up, get me pregnant’ she grinned
I began pounding her lovely body, I got to the point of no return then emptied my balls into her.
‘Wow, you are one helluver fuck Carol’ I gasped
I wiped us with the tissues.
‘Thank you sweet girl’ she said rolling onto her back ‘I want you to kneel astride me’
I did as she asked, she squeezed the last of the KY getting us ready
‘Lower yourself on me Alice darling’
I grasped her dick behind me and guided it as I lowered down onto it, I was finding it easy to take her dick in me now, and it felt nice as I slipped further down onto her lap.
‘Are you comfortable’ she murmured sweetly
‘Mmm, yes’
‘Try to grip me with your rectum’
Although I had her dick in me and had stretched me, I tried gripping her with my anal muscle.
‘Do it harder’
I tried clamping her dick as if to part it in two.
‘That feels great, now try drawing me in at the same time’ she said putting her hand on my abdomen.
I started using my inner stomach muscles attempting to get her deeper in me at the same time as trying to cut her dick in half with my rectum.
‘Wow, you’ve got it, it feels so much better than a female pussy’
I smiled at her, then lifted my bottom up a few inches, Carol began fucking up into me furiously. I loved the feel of her dick sliding in and out while watching her smiling face below. I continued using my clenching and drawing of her dick, it seemed to enhance the exquisite feeling of being fucked. She was now thrusting hard, her dick swelling and began the pulsing as she shot her load into me.
‘That, darling Alice, was most definitely the best fuck I have ever had’ Carol panted.
‘I hope I am not turning gay, but I loved every second of it too’. I said concerned.
‘More like being a lesbian, we are two sexy girls making love, tell me, would you like to see a man doing you’?
‘No, when I think of it, I would hate the idea’.
‘Come let’s get sorted and grab some breakfast’
We undressed and dived in the shower naked, Carol was right, once the clothes and makeup came off, I did not fancy her at all, in fact I felt embarrassed seeing a man in my shower.
Carol got dressed in her girl clothes and put makeup on, I had to put on my boy clothes because I would be off to work. We had breakfast as a boy and girl, she explained she worked flexi time and tried to do a ten or twelve hour day and build up two or three days off, then off to a motel to be a girl.
‘I have not come out at home because my mum and dad would have a fit, but I do love shopping, going out in public and being accepted as a girl’
‘You certainly look like a pretty girl, if I hadn’t seen your dick I would never have guessed. My dad doesn’t know I dress either, I usually dress up when he is working, I use my mums clothes, they fit me perfectly, she left loads of really nice things behind, even her makeup and perfume’.
‘Tomorrow you said you were going to work dressed up and it would be your first time out. Well all you have to remember is that be confident, you are a girl, you look like a girl, and, by the way, you look very sexy also you have great legs’
We chatted over our coffee, swapped phone numbers and email addresses, just as we parted Carol hugged me then kissed me.
‘Ugh, I just snogged a man’ she giggled ‘we have to keep in touch, I will miss you, and let me know how you get on about tomorrow’
‘I will miss you too Carol, I feel I have met my soul mate with you. I will call you this coming weekend, ‘bye’.
‘’bye lover’
I packed my things and loaded the car. I made it on time to work at nine fifteen. Time seemed to drag, but I completed my work early afternoon. I made out my report then passed it to the office manager, he thanked me for my efforts, and said how pleased he was about how his system was working smoothly and had speeded up.

Later that afternoon, I arrived at the motel in Hampshire, once in the car park I let my hair down, removed my jacket and tie, put on a little lipstick then went and signed in as Alice Smith.
Then in my room, I carefully hung up my lady business suit and sorted my underwear and shoes for the next day. I showered and shaved my body and legs, I was very lucky that I had little body hair it was blonde, very fine and sparse. I blow dried my hair and gave it a little curl, I painted my nails, both hands and feet in a dark pink, dressed in matching bra and panties, corselet, stockings, made up my face and made a coffee from the service pack in the room.
Using my mobile phone, I contacted the manager of the company I would be visiting the next day and arranged to be there around nine am.
I was wishing Carol could be here, I felt I could do with some moral support, I missed her a lot, I knew I was falling in love with her, and the sex with her was out of this world.
I put on a cotton dress and short jacket, three-inch heels, grabbed the new purse Carol had bought me. As I reached for the door, I stopped, ‘well Alice, this is it’ I said to myself ‘my first outing alone as a girl’ I went out the door and made my way to the restaurant. It was fairly busy, only a few tables empty, I felt everyone was looking at me when the waiter came up and asked,
‘Table for one miss’?
‘Yes please’ I answered.
He seated me almost in the centre of the tables, I would have preferred being on one side, ‘never mind’ I thought, at least I would be on show for my initiation among people, I must try to act like a lady. I placed my order, and furtively glanced around, nobody seemed to be looking at me except for a young man over one side, as our eyes met he smiled, I looked down at my manicured hands. My order arrived, I ate as delicately as I could and not looking around. When finished I declined coffee, I thought I would have a drink at the motel bar, as I stood , I noticed the young man had already gone. As I entered the lounge bar, he was there seated on a stool at the bar. I tried to avoid him by going to the far end. I ordered a dry white wine, when it arrived I reached for my purse.
‘That’s ok miss, the gentleman over there paid’ he pointed to the young man.
I looked over to him, he smiled, I lifted my glass smiled back and mouthed ‘thank you’. I carefully made my way to an empty table with comfy armchairs.
‘Please may I join you miss’
I jumped
‘I am so sorry I startled you’ the young man said
‘I was deep in thought, I was not expecting anyone’
‘May I’? he indicated the chair opposite
I nodded
‘My name is Chris’ he said holding out his hand smiling
‘Alice’ as I shook his warm hand
‘On holiday’?
‘No just work’
‘You look like a model or something’
‘Thank you, but no, I am an IT engineer’
‘I never would have guessed, you should be in front of a camera. As for myself I am a salesman for office equipment, I come from Southend in Essex’
‘Brentwood Essex, I live with my father’
‘Not married’?
‘No, not even thinking of it either, I am very happy as I am’
He ordered another round of drinks
‘Please let me pay this time’ I asked
‘Certainly not, it is my privilege’
We chatted about all sorts of things, he seemed a nice person, he was single and not in any hurry to settle down, he asked me a couple of times whether I was in a relationship or not, but I avoided a direct answer, just mentioning that I had met someone a couple of days ago and was hoping to see them again sometime.
He went to order more drinks
‘Not for me thanks, I want to keep a clear head for tomorrow, especially as it is a new customer’
‘Will you be staying tomorrow night’?
‘Probably not, unless I run into any nasty problems’ I stood and offered my hand ‘it’s been nice to meet you Chris’
He shook my hand ‘Alice, I do hope we bump into each other again’
I smiled sweetly, then left and returned to my room. I knew by his manner that he would love to have got into my knickers. He was the first man that I had even found slightly attractive, ‘god, I am thinking like a girl now’. I undressed, washed, cleaned my teeth and popped into bed wearing the baby doll that Carol had worn this morning, thinking of her I drifted off to sl**p
I woke up gradually, I felt good as I stretched, then I realised that today I was going to work as Alice, I looked at the clock six-thirty, I quickly showered, had a very close shave, I usually only needed a shave every third day of my fine soft blonde beard, but today was special. I blow dried my hair adding the curl, I was meticulous with my makeup, I used a tight bikini pouch which pulled my dick under me, which once I put my panties on gave no sign there was anything there. Once fully dressed I scrutinised every detail of myself carefully, I looked one hundred percent girl, I even fancied the girl in the mirror looking back at me.
I was eating my breakfast when Chris came in
‘Good morning Alice, you are looking great today’
‘Morning Chris, and thank you’
‘May I join you’?
‘Yes of course’
He went off to get his meal, as I watched him walk to the servery, I wondered what it would feel like to be kissed by a man, I knew that kissing Carol was really nice, but it did feel I was kissing a girl, is a man different? I thought.
‘I’m famished’ he said sitting opposite
His table manners were very good, he did not talk while eating and he chewed with his mouth closed, when he finished, he put his knife and fork together neatly on his plate, ‘mmm, he was nice looking, here I go again’ I thought, ‘thinking like a girl’.
He came around the table, offered me his hand
‘Coffee in the lounge’? he asked
I took his hand and rose from the chair
‘That would be nice, thank you’
We walked holding hands to the lounge, he led me to a table,
‘I’ll get them, how do you like it’
‘Just a hint of milk and one sugar please’
Again I watched him as he walked away, then when he was returning he was concentrating not to spill the drinks, I noticed the outline of his dick in his trousers, half hard and a fair size, ‘once more I was thinking like a girl, I have got to stop it, I am not gay’ I was getting annoyed with myself.
We sat sipping our drinks, Chris put his hand on mine
‘Alice, I really want to see you again, I would love to take you out and wine and dine you one evening’
‘Thank you Chris, that is a nice offer, but I don’t think we would be suited’
‘I think you are the most attractive and sexiest lady I have ever met’.
‘Please don’t spoil the day for me, you are a very nice handsome man, I like you, but I am afraid it would never go further than that’.
‘Can we at least be friends’?
‘That would be nice, but look, I have to go, I don’t want to be late for a prospective new customer’
‘Here, take this, please call me’ he said handing me a piece of paper
It had his home and mobile phone number and email address.
‘I will. Goodbye Chris’
I collected my laptop and tools from my room and set off.

Arriving at Santex, the security guard pointed to the visitors parking. I parked and collected my things, pinned my identity badge to my jacket, I felt so nervous as I entered into the reception, I handed my security card to the receptionist, she scanned it.
‘Welcome miss Smith, you are expected by Mr Paul Copeland the senior office manager, would you go to his secretary on the fourth floor, she will be expecting you’ as she handed back my card.
I took the lift and found Mr Copeland’s secretary, she was ready and waiting for me.
‘Hello miss Smith, please go in, Paul is expecting you
‘Thank you’ I said entering the office
‘Ahh, miss Smith, or may I call you Alice’?
‘Alice would be fine Mr Copeland’
‘Please call me Paul, I hate formalities’ he handed me a batch of papers ‘these are our problems with our computer network system, I am sure you wish to study them, so I have arranged a private office, a computer and terminal, for you, my secretary Jean will show you around’ he pressed a buzzer ‘Jean? Alice is all yours now’.
We shook hands. Jean was waiting for me.
‘Hi Alice, you have an office on this floor, I will show you, and please if you need anything please call me’
She showed me the coffee machine and toilets and led me to a room.
‘I will give you a call at twelve-thirty lunch time’ she showed me a direct call button to her desk ‘anything at all, just call’ she grinned
‘Thanks Jean’ I smiled back.
I removed my jacket and sat in the comfortable swivel chair, plugged in my laptop, booted then set the diagnostic programme to run. I began reading the papers Paul had handed me, usual problems, the odd crash, running slow, memory hiccups, general things until I noticed that Santex had been pre-empted on tenders for estimated costs a few times by other companies. I quickly stopped the diagnostic programme and started a programme I had made, I watched the screen, a few anomalies began to show up. After an hour I had a list of peculiar happenings. I used their computer to follow trails on the internet, a further hour, I found that there was a company called Unix corporation who had access to Santex main frame they had also included a warning system to let them know if Santex had alterations or modifications made to their computer system, luckily I had stopped the authorised diagnostic programme, as once it had got into Santex system, Unix would have been notified, but my own programme could not be detected. ‘I better tell Paul’ I said to myself. I pressed the button for Jean
‘Hello Alice, can I help’
‘I have some sensitive information I ought to pass to Paul’ I said
A minute later Paul entered.
‘Do you have a problem Alice’?
‘No, but I think Santex have, do you know a firm called Unix corporation’?
‘Yes of course, they have been our hardware and software service company for over two years, the reason your company was called in is because they couldn’t get here for another week and your company has the highest security. Why is there a problem’?
‘They have left a small programme running in your system, it gives them access to all of your information, and also of any alteration of your software, even a diagnostic check would alert them. I had just started to run the programme when I saw your company had been pre-empted on several occasions on your estimated tender quotations, that means that somehow a rival company was getting fore knowledge of your pricing. I stopped the diagnostic programme immediately, and started one I devised myself for detection, I found the offending link, I made a fictitious entry to purchase one hundred cards for an estimated one hundred thousand, purely so that keywords would send the message, and by using my laptop computer, I was able to follow the message through two drones, which then directed it to the final web IP address. Which with a bit of checking, I found it to be Unix.’
‘bl**dy hell, oops, sorry Alice, that means the whole of our database is breached, can you remove the offending programme’?
‘Not without them knowing. I would suggest you find who commissioned them in the first place, you may have someone who has been planted here’.
‘I will get on it immediately’ Paul said rushing out
I was a bit stuck, if I started sorting out Santex problems, it would notify Unix, so until Paul gave me the OK to remove the offender, I could only do some unobtrusive checks. A little while later, Jean popped in.
‘Hi Alice, ready for lunch’?
‘Mmm yes’
I put my jacket on and we went in the canteen. After sitting at a table with our lunch, Jean said
‘I don’t know what you said to Paul, but he looked really serious and went straight on the phone to the MD’
‘Oh, it’s nothing really, you will find out later’
We chatted over lunch, she was surprised I didn’t have a boyfriend
‘A girl who is sexy and attractive like you, you should be fighting them off’
‘In between at the moment’ I replied
‘Alice? I am sorry to disturb your lunch, but would you have a word with the MD please? It is very important’ Paul asked anxiously, ‘and Jean would you come too please’?
We went to the Managers office, there was a middle aged gentleman in there,
‘Andrew, let me introduce miss Alice Smith’ Paul said ‘Alice this gentleman is our managing director Mr Andrew Snelling’
‘Pleased to meet you Alice’ Andrew shook my hand ‘Please call me Andrew. Well young lady, it looks like you have stirred up a hornets nest, I can’t thank you enough for bringing this to light, Andrew has told me how you used your homemade checking programme so as not to alert the enemy, so to speak, also how you traced them. I have made arrangements with the authorities to enter their premises and check their computers and main frame, but that will happen this afternoon. I will contact your office and ask if it is possible for you to come back tomorrow, to finish your work’?
‘Thank you Andrew. Is there anything I can do this afternoon’?
‘Not on our computer system, we are only using them for minimal work until their system is quarantined, so you may as well have the rest of the day off’.
‘I will see you all tomorrow then’.
I had dropped myself deeply in the mire, he was going to phone my office, who have not got an Alice on their books, ‘shit’ I thought, I will be found out and lose my job. On the way back to the motel, I stopped off at a pharmacy and purchased a colonic douche, after being with Carol I liked the feeling of being clean inside, back at the motel I carefully removed my suit and hung it up. My mobile rang, I started to shake with nerves when I answered it.
‘Hello’ it was my manager,
‘Good afternoon MISS Smith, I have just come off the phone from Andrew Snelling, I have agreed to let you go back tomorrow to finish off your work. I don’t want you to explain now, but I want you in my office on Monday morning dressed exactly how you were this morning at Santex, I mean exactly. Then I will need explanations why, then, how come you make your own programme and run it on our clients system. In conclusion, Mr Snelling thinks very highly of you and praised, in his words, quote ‘a very attractive intelligent young lady’ unquote. And from me, thank you for doing a good job, See you on Monday Alice, ‘bye’
I didn’t know what to think, I had been reprimanded and praised, I do hope I won’t lose my job over it all. I started to cry, I was in a bit of mental turmoil.
Knock. Knock. on my door who on earth can that be? I opened it to find Chris standing there.
‘Wow you look…oh Alice your crying’
He rushed in and hugged me tight, I realised that I was only wearing my underwear, he gently wiped my tears with his finger then kissed me, I was not expecting that, his tongue was probing my lips, I was off guard and let it in, the kiss lingered I was enjoying it now, both our tongues probing each others mouth, I could feel his dick pressing on my stomach. Finally I pushed him away from me.
‘No Chris, I don’t want this, I am sorry but you would not understand’
‘From the way you kissed me back, I know you enjoyed it, after all we are both adults, what objections do you have? I think you like me, I know I like you very much and you look fantastic, what is it that I would not understand’?
I sat down, put my head in my hands
‘You would hate me, I want you to leave’
I started to cry again.
‘What is troubling you Alice, I would really like to help if I possibly can, please give me a chance’.
‘It’s not you Chris, it is me and what I have done’.
‘I beg you Alice, please tell me’
‘I will say one sentence, then I think you should leave’
‘Go on, please’
‘I am not a girl’
‘Of course you are a girl, may I add, a very sexy girl’
I stood up lowered my panties, put my hand under and removed the plaster so my dick appeared, the look of shock on his face, his eyes opened wide.
‘Now you can leave Chris’. I said
‘I…I still want to stay, I want to hear your story, and I still think you are very sexy’
I told him of how I dressed at home, and in motels and that this time I met another transsexual girl, also that I had decided I would go out for the first time dressed and go to work, how the customer phoned my boss and how my boss wants me in his office dressed on Monday.
‘And that was why I was crying, because I could lose my job’
I had not told him about my work.
‘Can I still wine and dine you this evening Alice’? he asked
‘You want to? Even though I am not a girl’?
‘I would be proud to have you on my arm, I still think you are gorgeous’
He stood and came over to me, grasped my hand and lifted until I stood half naked in front of him, he lowered his face to mine and we kissed, it became a passionate kiss, my dick became hard. After a while we broke the kiss and he lowered himself onto his knees, he clasped my dick then kissed all around it, then sucked it in his mouth, his head bobbing back and forward, with one hand he was caressing my balls, the other was stroking my nylon clad legs, he licked the underside of my dick as he sucked it in his warm moist mouth, I was enjoying a blow job from a man, I had to warn him
‘I am going to cum’
He held me in and sucked harder, I felt my dick explode into his throat, he gulped and gulped, swallowing all my sperm. My knees started to buckle, as I slowly lowered to the chair, he licked my dick clean.
‘I said I wanted to stay, didn’t I’?
‘You were so good, you must have done that before’
‘Honestly, that was the first time I have ever even touched a dick, I know what girls have done for me, so I just copied their method’
He leaned forward and kissed me tenderly, and whispered, I want to make love to you Alice’
I began thinking, if I let him, it means I am letting a man into me, which therefore makes me gay, but I would still like his dick in me.
‘Only if you take it slowly and wear a condom, I will have to get ready first’
I went in the bathroom and gave myself a douche, I realised then that I wanted to be fucked as a girl by a man. I returned to the bedroom.
‘Oh Alice darling, you look fantastic’
He quickly undressed, his hard dick sprung out, larger than Carols, I placed my hand around it kissed his knob, licked up and down, it was very hard. He lifted me up and carried me to the bed, I got on my hands and knees, my bottom in the air. I looked back as he put on a condom.
‘There is some skin moisturiser in the bathroom, I will need some in me first’
he went and got the bottle, his dick waving up and down as he walked, I felt him lubricating me, using his fingers, then his dick pressing at my anus, I relaxed, then he popped inside me, his dick stretched me.
‘Gently please Chris’
He slowly pushed into me, it was a bit painful, deeper and slowly deeper, I felt his thighs against the back of my legs, he stopped moving, fully in me.
‘God you are tight Alice, but you feel wonderful, are you ok’?
As an answer, I gripped and drew him like Carol had taught me, then wiggled my butt.
‘Wow, that’s fantastic’ he gasped
He began fucking me, withdrawing and sliding back in, any pain had gone, all I could feel was a nice large dick moving inside me.
‘Can we change position? I want to look at your pretty face’
He withdrew from me, I felt so empty as I rolled onto my back, I placed the pillows under me lifting and offering my bottom to him, he lifted my legs to his shoulders, then he leaned over and put his dick back in, he smiled. I smiled back at his handsome face.
‘You are so pretty Alice’
He was soon pumping in and out of me again, he was stroking my half hard dick, I was really enjoying my first man making love to me, he gritted his teeth then I felt his dick pulsing inside. At that moment I knew that I was bisexual, I liked being fucked, and I liked fucking, especially Carol.
Chris withdrew his dick, leaned and kissed me tenderly.
‘You are amazing Alice, that was the best fuck I have had for years, I have never been with anyone but female before, you are my first cross-dressing girl’.
‘You, darling Chris, are only the second person who has fucked me’.
He removed the condom and went to the bathroom, when he came back he said
‘Are you hungry yet’?
‘Yes I am a bit, I never quite finished my lunch’.
‘I will call back for you, is an hour long enough? Then I will wine and dine you’
‘That’s fine, it will give me time to get ready’
He held me close, we had a tongue fighting kiss’. He got dressed.
‘God, you are so sexy’ he said as he left.
An hour later, I was dressed and made up, just checking my purse Carol had bought me when Chris arrived.
‘Wow, you are a real knockout Alice, fancy a quickie before dinner’? He said grinning.
‘You have to feed me first’ I said pecking him on the cheek
‘Does that mean I am on a promise then’?
‘If you feed me first and will still want me after’.
‘You can bet on it, I can’t wait to get back in your pretty panties’
‘I reckon you would look good in them, but you would have to shave all over’ I grinned.
We had a good romantic meal, he was very attentive and kept whispering sweet things to me. We danced a few slow ones, his dick was constantly hard, I grabbed it a couple of times when no one was looking.
‘I want you so badly Alice, can we leave soon’?
‘Ok, but I have a long day tomorrow, so you must leave by midnight, until then, I am yours’
He drove back fast, no sooner had we got in the room he was stripped off, he helped me off with my dress and shoes, I took my panties off letting my stiffy free, once again he gave me a very good blow job and swallowed the lot. He put on a condom and once lubricated me with moisturiser, he gently entered me with my legs on his shoulders, he is a considerate lover, making sure I was comfortable as he fucked me like a woman. I loved having his dick sliding in and out of me, I felt very girlie being made love to. His face took on an urgent look, he thrust into me harder, his dick throbbed as it unloaded his man juice. He pulled out his softening member, removed and tied off the condom, wiped his dick with a tissue. We went into a long lingering kiss, he was holding me close, and whispered,
‘I could easily fall for you’
‘Now Chris, you know that is impossible’
‘But you are so sexy and feminine’
He started kissing my neck then gradually down my body, he put his tongue in my belly button, then proceeded down my leg, he sucked each painted toe through my stockings, to the other foot, up that leg, he turned me on my front and tongue fucked my rectum, this was turning me on, I was getting a hard on.
‘Would you like to fuck me’? he asked.
‘Do you want me to’?
‘I wondered what it would be like’
‘I’ll tell you what, if you don’t like it or if you want me to stop, just say, but you would have to give me another blow job instead’
He passed me a condom, I prepared his rectum with moisturiser and managing to get two fingers in him. His bum was in the air ready. I pressed my dick at his entrance,
‘Just relax, Chris’
The head of my dick popped in
‘Ow’ he yelped
‘Sissy’ I teased
I eased in very slowly, he grunted a little as I got deeper, finally I was fully in him, I rested a while to let him get used to me, I could tell that the pain was going when he moved back on me. I began fucking with small movements. Although I did not find it sexy to fuck this man, the warm tight grip on my dick felt great, I found by closing my eyes and imagining I was fucking Carol, gave me extra lust, and I began fucking harder. After a while, I could not hold back and shot my load. I slowly removed my wilting dick, making slurping noises on the way out.
‘I now know how you feel, once the pain subsided I rather enjoyed it, it was my first time being fucked, and by a sexy girl as well’ Chris smiled
I removed the condom, and wiped my soft dick
We held each other close, I whispered in his ear
‘Fuck me’
He didn’t need telling twice, in record time he had me on my back and moisturised, his dick sheathed, and was entering me. I was getting used to his large dick, it didn’t take long before he was fucking me with the full length. It was a long leisurely fuck, no urgency, both savouring good sex. Eventually his dick swelled and pumped out his load. After he sorted himself out, we just lay in each other’s arms just as normal lovers would. I looked at the clock, just gone midnight.
‘I am going to turn into a horrid witch any second’ I said pointing to the clock.
‘Sorry darling, I was feeling so happy being with you’
He got up and was dressing
‘Can I see you again Alice’?
‘I am not sure, it’s according to how my work goes, when do you have to leave’?
‘Friday morning after breakfast, I am working all day tomorrow, so I have one more night here after tonight’
‘Give me your number at breakfast’
‘Ok darling, see you there’
He gave me a loving goodnight kiss and left.
I slept like a log, the alarm went off startling me to the morning, in the shower I shaved all over. Dressed in my suit I looked in the mirror checking every detail, ‘yes’ I thought ‘I do look good’, as I walked to breakfast, my bottom was a bit tender reminding me of the good fucking I had the night previous.
‘Hello beautiful, how are you this lovely morning’ Chris said beaming as he came to my table
‘Happy now I have seen your handsome face’ I smiled sweetly
‘I bet you say that to all the men’
‘No, only the ones that have fucked me silly half the night’
‘You said I was the only one’
‘And you are the only one I have said it to’
We both burst out laughing. He gave me a card with all his details, I finished my breakfast
‘I have to go’ I kissed him on the cheek
I arrived at Santex, went through the security check in reception, made my way to Paul’s office
‘Hello Alice, go right in, they are expecting you’ Jean piped up cheerfully
‘Hello Jean, thanks’
I was nervous of what to expect, I knocked and entered, Paul and Andrew were there
‘Ahh, Alice Smith’ Andrew stepped forward and shook my hand warmly ‘you are our angel, you have probably saved this company many thousands with you discrete findings, you will have to excuse me, I feel a bit ragged today, I have spent most of the night with the fraud squad and police. Unix has had all their computers, mainframe and peripherals confis**ted and taken to police forensics for examination. We will keep your company informed of the outcome. As head of Santex I offer you our heartfelt thanks’
‘Thank you Andrew, it is only part of my job’
‘I hope to speak to you again before you leave today’
‘May I get to finish my work now’?
‘Yes it is safe to carry on now’
I smiled and left the office
‘Catch you for lunch at twelve thirty Alice’ Jean said
‘Look forward to it Jean’
I set to work, I ran the diagnostic programme, found many faults and anomalies, made a folder to hold the rarely used programmes, and generally cleaned up the whole networked system.
‘Hi Alice, fancy a bite’ Jean put her head around the door.
‘Goodness is that the time, be right with you Jean’.
Once seated with our meals, Jean remarked
‘Well, who’s the flavour of the month then? Andrew and Paul haven’t stopped talking about you all morning’
‘I was just lucky I noticed it’
‘Not only your work, they both fancy you’?
‘Oh no, that’s embarrassing’ I blushed
‘They reckon you are really sexy’
My bottom was still a little tender from last night, but it still gave a twitch at the thought of men wanting to put their dicks in me. Wow, if only they knew, I would be thrown out so quick my feet wouldn’t touch the floor. I was beginning to regret dressing as Alice.
‘I’m not sexy, I am just me’
‘Well, even I think you’re sexy, don’t get me wrong, I am not lesbian, but there is something about you that is very attractive’
‘Now I really am embarrassed’ I felt my face blushing
I thought that she was sexy and I would love to fuck her, but she would run a mile if I got my dick out.
‘Come let’s have coffee in the lounge’ she urged
I was getting aroused and it was uncomfortable with my dick taped back, but thankfully the chat went off sex and became girl talk, clothes, makeup etc.
‘Ah well, back to work’ Jean said ‘catch you later Alice’
‘Yes, see you’ I replied
I settled down in my loaned office, I had about two hours work at most, I concentrated on what I was doing. Finally I finished. I went to Jean and asked to see Paul, she called through the speakerphone
‘Send her in Jean’ Paul’s voice replied ‘Ah Alice, how are things going’?
‘All finished Paul, except for rebooting the system for the changes to take effect’
I could see by his eye movements that he was mentally undressing me, I smiled to myself.
‘Jean’? He called ‘can you arrange a short shutdown on the computer system please’ then to me ‘please take a seat Alice’
Keeping my knees together and adjusting my skirt, I sat carefully on the offered chair. Two minutes later, Jean called
‘Ready Paul’
‘All yours Alice’ he said
I went back to the office and rebooted the system, once back, I checked everything was working ok, no problems running smoothly. I gathered my things, then back to Paul’s office.
‘All finished Alice’? Jean asked
‘Yes thanks Jean’
She ushered me through the door.
‘All ok Alice’?
‘Yes fine thanks Paul’
‘I can assure you that your company will get a glowing report concerning your work, I can’t thank you enough for your efforts’ he shook my hand warmly ‘goodbye Alice, I am pretty sure we will see you again’
I groaned inwardly
‘Goodbye Paul, I am glad I was able to help’
Jean came to the lift with me, she turned me and kissed me on the lips, I was helpless holding my cases in each hand, I kissed back.
‘Goodbye sexy girl’ she whispered
I smiled and blew her a kiss as the lift doors closed. once back in my hotel room I looked at the clock, four thirty, I didn’t fancy the drive home as I would hit the rush hour, and I was a bit weary from the day, so I decided to leave tomorrow after breakfast. I stripped off and had a shower, gave myself a douche, once cleaned inside and out, I put on the corselet, panties, bra, stockings, mini skirt and blouse. I put on new makeup and brushed my hair. I felt and looked good, hopefully Chris will be around later and give me a good fucking. At six o’clock, I reckoned I will be spending the evening by myself, as I grabbed my purse
‘knock, knock’
An attractive brunette woman in a short dress was standing there, I was just about to ask what she wanted, when I recognised it was Chris.
‘Oh my god, it’s you Chris’
‘Let me in quick’ he said as he rushed by me
‘Stand back, I want to see you, why this’? I asked pointing to him
‘You are one of the most sexy girls I have ever met, I love fucking you, and I enjoyed you fucking me last night. You did say something about me wanting to get in your panties. I got to thinking, what it would feel like dressing as a girl, so I did a bit of shopping’.
‘Actually you don’t look too bad, and I like the hairpiece’
‘I have shaved all over, I am a bit unsteady with the heels, but I need you to make up my face’
‘Come, sit over here, I will make you pretty’ I pointed to the vanity stool
‘Can you call me Christine now’?
I kissed her lips
‘Hi Christine’
I started making up her face, after twenty minutes she looked very attractive, I turned her so she could see in the mirror.
‘Coo, I look really nice and girlie’
‘So good that I will have to fuck your brains out later’ I grinned at her. ‘Now stand and walk about’
She was unsteady with her heels, but she was definitely passable as a girl.
‘Keep practicing, and take shorter steps’
‘It feels so nice wearing these clothes’
‘You are looking good Christine, are you hungry’?
‘Yes but I will have to change back first, no way am I going out like this’
‘Oh yes you are, you are very passable as a girl, we will go to where you took me, it has subdued lighting and nobody knows us anyway’
‘But you have done it before’
‘Until yesterday I had never been out except to go to the corner shop and that was late at night’
‘Really? You look so natural and confident’
‘Come girlfriend, my treat tonight’
Christine looked worried as I drove, I parked up and held her hand as we walked into the restaurant.
‘Good evening ladies, table for two’?
‘Yes please’ I answered ‘to one side if possible’
‘Certainly madam, this way please’
There were a few customers seated, two or three looked up at us but then carried on eating, one man took a second glance at us.
‘Horny bastard’ I thought
Once seated, Christine relaxed a little.
‘There, piece of cake, wasn’t it’?
‘Do you think anyone knows’?
‘Of course not, even the man over there was leering after you’
Christine giggled. The waiter came and took our orders, Christine unobtrusively glanced around,
‘Oh my, he smiled at me’ she said nervously
‘There, I told you how good you looked, now you have an admirer, don’t worry, he only wants to fuck you’
‘Ugh. That’s gross’
‘I bet he has a big dick’
‘Do you think so’? Christine enquired
‘Would you like to try it’?
‘No certainly not’
‘Even if he paid you’?
‘No, it would make me a prostitute, anyway how much would he pay once he found out I was not a real girl’?
‘I could tell him anal only and he would have to use a condom, maybe you could get eighty to one hundred pounds, just to get his nuts off’
‘Wow, all that just to fuck little old me’
‘Want to try it’?
‘No Alice, I only want you tonight’
‘I could chat him up for you and haggle the price’
‘Why do you want to sell me to a stranger’?
‘You said you enjoyed being fucked, and it would give you confidence as a girl, to know that you are attractive enough for someone to want you’
‘Where would we do it? Certainly not back at the motel as he could find out who I am’
‘Behind my car in the car park, it’s facing into a dark corner, you could bend over the bonnet’
‘My god, you really want me to go through with it, don’t you’?
‘It would only be for about ten minutes’
‘A hundred pounds for ten minutes’
‘Just turn and smile at him, to see if he is interested’
Christine turned her head and gave him a sexy smile, the man smiled back and made his way over to our table.
‘Good evening ladies, may I introduce myself, my name is John, could I have the pleasure to buy you a drink at the bar’?
He was talking to Christine as he asked, I could see by his gaze that he fancied her.
‘Thank you, that would be nice, this is Christine and my name is Alice, we will freshen up and meet you there’ I answered
‘I will get the drinks in, what would you girls like’?
‘Two dry white wine please’ Christine quickly chirped in
John headed to the bar, I paid the bill, then led Christine to the ladies.
‘Alice, I am so nervous, I am not sure I can go through with it’
‘You will be fine, all you have to do is bend over and think of England while he has his wicked way with your bottom’ I said grinning ‘drop your panties and let me prepare you’
She pulled her panties down, I removed the tape from my dick and taped hers up tight, then using the skin moisturiser from the ladies vanity shelf, I lubricated her anus and managed to eventually get three fingers into her, stretching her rosebud open. I tucked my dick back and pulled my panties up tight.
‘Let’s go girl, John is waiting’
I led a very nervous Christine to the bar, John was seated on a sofa by a small table with the drinks on.
‘Hi girls, have a seat’
‘Can I have a quiet word John’? I asked
John stood up and led me to an empty alcove.
‘Christine is just about to go on the game, she has never sold herself before, I have offered to help her out with her first few clients, it would cost you a hundred pounds cash up front if you want to be her first, but you can only have her anally and you must wear a condom’
‘Supposing she isn’t very good, it seems a lot of money’
‘Ok, if you give me eighty pounds, you can have her, but if you enjoy her, you can give me another twenty. How does that sound’?
‘Seems fair’
He peeled off four twenties and handed them to me, we returned to the sofa, Christine glanced at me nervously. John put his arm around her and whispered something in her ear, she went bright red and nodded to him. John stood up and held his hand out to her, she grasped his hand as he led her outside, she gave me a very worried look as she left with him. I checked my watch, just twenty to the hour, I thought I would give them to the hour before I would get concerned. I sipped my drink, feeling bad about putting her in this position, I began sipping her drink, constantly looking at my watch. As the minute hand reached the hour, I was feeling panicky, just a few more minutes I thought. At ten past, I stood up ready to go and look for her, when they strolled in arm in arm, Christine’s face was bright red and she was walking unsteadily. John helped her onto the sofa, noticed our glasses were empty.
‘I will get fresh drinks’ he said as he left for the bar.
‘Well’? I said
‘God, he is so big, and at least eight inches, I thought he was going to split me in two, and he kept going for such a long time before he cum’
‘How do you feel’?
‘Wonderful, but a bit sore, I feel so girly, he kept telling me what a great fuck I was. Oh Alice, I loved it. He is ever so nice, he treated me like a lady, and he fucks like a stallion, he pleaded with me not to be a whore and asked me to live with him.. oh, here he comes.. tell you later’
John returned with the drinks,
‘Here you are girls’ as he put the drinks down
He pulled out his wad of notes and handed me another four twenties, winked at me and said quietly
‘Best fuck for years’ grinning broadly ‘oh, and by the way, I know she is a he’
‘How’?
‘Christine got a stiff dick while I fucked her, even the tape couldn’t hide that’
he turned to Christine,
‘I really want to see you again, I would like you to be my regular girlfriend’ he lifted her hand and kissed it.
‘I think I would like that too John’ she whispered as she kissed his cheek
‘Before I get in the way of you two lovebirds, I owe you some money Christine’
‘Keep it Alice, if it hadn’t been for you, I would never have met her’
‘But she earned it’ I said
‘Treat yourself to something nice’ Christine said ‘I have got what I want right here’ she said kissing his cheek again ‘I will see you before you leave, say around nine at breakfast’
‘I will make sure she is there’ John said earnestly
I made my farewells and returned to the motel, thinking about Christine and John.
Next morning, I decided to stay as Alice to drive home. I packed my boy clothes and wore my summer dress to go to breakfast, I was feeling so alive and happy as a girl. At ten to nine whilst eating my breakfast, Christine arrived and I could see by the rings under her eyes and the careful way she walked, that she had been busy last night’
‘God, Alice, I am in love with him, I can hardly walk and my bum is so sore, he kept making love to me half the night. You were so right when you said I looked good as a girl. I have come to collect my things, I am going to move in with him, he is waiting outside to take me shopping for clothes and I am booked in for a makeover. Thank you so much for everything. Here take my card, it has my mobile number and email address, please contact me over the weekend’
I gave her my card, the one with Alice Smith on it.
‘I am so pleased for you Christine, I do hope you will be happy, take care sweetie’ I kissed her cheek.
Continued in Alice part two.













































Alice

My name is Alan Smith, I am twenty two, about five foot six, fairly slim at just nine stone, my hair is dark blonde and fairly long, sometimes I put it in a pony tail. I have a degree in computer science, I work for an I.T. company, travelling around the southern half of England fixing computers and programming. I live with my dad Greg in a quiet suburb in Essex. My mum Elizabeth left us about four years ago, that was such a surprise as mum and dad got on very well, there did not seem any reason for her to leave, but dad and I have got over our loss now. Dad belongs to a singles social club, he sometimes dates different ladies from his club. Me, well I occasionally get a chance to date the odd girl, but I am not into any commitment. When mum left us, dad moved into the other bedroom, he never moved any of mum’s things, I suppose he hoped she would return. When I was home alone I used to go in mums room as I called it, to become Alice, and dress up in mums clothes, as she was a flirty lady, her clothes were very sexy. I loved the mini dresses and silky underwear, most of her clothes fitted me perfectly even our shoe size was the same. I used to look forward to my time alone dressing up and feeling girly.
My work often called for me to stay in a motel or hotel for a night or two, when I knew I would be away, I always picked some clothes and get dressed up in my hotel room, I had never been outside when dressed up, I was a closet dresser, I was too scared to venture out in case I was found out.
I was due to travel to Gloucester for work, then down to Hampshire, two or three days away. It was early afternoon, dad was at work, I went to mums room with my case. Stripping off my clothes, I had decided to try on a few things that I would take with me. I put on my favourite panties, corselet with suspenders dark sheer stockings with strappy three inch heeled sandals, I was feeling good. Looking through the wardrobe, I picked a light summer mini dress, sat at the dressing table and applied a little makeup and lipstick, brushed and fluffed my hair. Standing front of the full length mirror, I took a critical look at myself, I could not fault my appearance, more than passable, I actually look bl**dy good, I wished I could pull a girl that good, I would fuck her brains out. I was getting extremely horny admiring the sexy girl looking back at me. I walked back and forward, the hem was three inches above the knee, I realised that if I was outside I would have to be careful if I bent or sat down or my stocking tops would be on display. I had got quite used to wearing heels, four years of practice in mums shoes had given me confidence. I proceeded to put various bits of clothing in my case, even a business suit that mum wore occasionally, I liked the formal female look it gave me, once I had sufficient for a few changes of clothes I got a small makeup bag with all the things I would need, packed all the girlie things. I went to my bedroom and packed enough boy things for my work. I had promised dad I would get dinner ready for us, I went down to the kitchen and prepared the meal, set the table. Looked at the clock and saw it was time to become Alan again. After returning all the clothes carefully to their proper place, I washed the makeup off, put an elastic band around my hair to make my usual ponytail, dressed in my scruffy boy clothes then checked myself in the mirror, all ok, I was back to being a normal computer nerd.
‘Hi Alan’ dad called as he came home
‘Hi dad, I’m in the kitchen’
As usual when he entered we had to go through the routine of a ‘High five’ as a greeting, it was something he liked to do to show his affection, a sort of ‘dad-son’ thing.
‘Mmm, dinner smells good’
‘Nearly ready dad, about five minutes’
Dad was an office supervisor, working in a large London office, many years ago he saw the potential of the computer, he groomed me and sent me to technical colleges and pushed me until I had a degree in computer science. Any new innovation that came along in that field, he sent me on the course to study it. I had many diplomas for different aspects in the IT industry. As my work takes me into highly sensitive and secure areas, I had a pass card and identity badge, these contained everything about me, age, height, hair colour, bl**d group, iris recognition data, even my DNA profile, a little while ago I made an exact copy of these except they had me as Alice Smith, female, even the coded picture was me as Alice, I knew they would pass even the toughest scrutiny, I had even added Alice in the main data base as my twin s****r.
I put the dinner on the plates
‘Smells good son’ he said as he entered ‘you will make a great housewife for someone one day’
‘Yeah, and pigs might fly’ I grinned.
Dad and I didn’t get a lot of time together, what with his work and social life, and my work as well, so when we did get the opportunity we had a good chat, this was one of those times. We finished our meal, I washed up the dishes then dad got a couple of beers from the fridge. I don’t drink much, I like to be in control of my actions, so I declined the second one he offered.
‘Sorry dad, I have to be up early and I have a long drive tomorrow, I will be away for three or four days’
‘You take care Alan, you are the only one I have left in this f****y’
‘I will dad, goodnight’
We high fived as I left for bed.
The next day I pulled in to the motel in Gloucester, I was a bit weary after the three-hour drive, I had left home at five am. At eight thirty after checking in and unloading my suitcase and tool case in my room, I sat in the diner area and had a nice breakfast. Back in my room I phoned the client to say I would be on site around nine thirty. I arrived on site went through the security having my pass and badge scanned. I was introduced to the office manager, who then explained their problems. I set to work. Whilst going through the breakdown procedures for fault finding, I realised that ninety five percent of my work I was by myself, with very little contact with any of the other employees. I thought if it was not a regular customer, I could get away with attending a site as my alter ego, and as the next customer was down in Hampshire and they were a one off call the day after tomorrow, I got excited at the thought of going as a girl. I’ll try it, just the once, to see how it feels to be out in girl clothes. I had a light lunch in the canteen, again with no interaction with the employees except at the coffee machine when some man told me to go first as he was getting several for his table, I thanked him, drank my coffee and set back to work. At five pm, I reported to the office manager and told him everything was going well and should be finished tomorrow.
On the way back to the motel I popped in an off licence and bought a bottle of wine, I would have a couple of glasses to celebrate my decision to go girlie on the next call. Back in my room I stripped and showered, put on my corselet stockings and panties, then covered them over with my boy clothes, then went to my evening meal at the motel diner. I could feel the silky underwear on my skin every move I made, I was feeling very horny. I sat eating my meal when…
‘Hello’
I jumped, my chair went flying and I finished up on the floor.
‘I am so sorry’ a young pretty blonde girl said as she helped me up, ‘I didn’t mean to startle you, I am really sorry’
‘That’s ok, I don’t think I broke anything’ I muttered
‘I came over to tell you that when you get dressed you should make sure the curtains are pulled’ she grinned as she sat opposite me ‘Oh, and by the way, I love your sexy underwear’.
I looked down at my hands, my face turned crimson, I sat there hoping a hole would appear and swallow me up.
‘Please don’t feel embarrassed, you see I am a male too’
I looked up at her startled, she was a very attractive blonde girl, pretty face and lips I could kiss forever, I could not see her figure at the angle I was sitting.
‘You are very pretty’ I said awkwardly
‘Thank you, I think you will make a great looking girl too. Now finish your meal then we can talk’
I had gone off my food and just pecked at the remains
‘Come’ she said standing and holding her hand out for me, ‘let’s go and talk’.
I held her hand, it felt warm and soft, she was wearing a sleeved cotton dress, three inch heels nicely shaped nylon covered legs.
‘Where are we going’ I asked.
‘To your room so you can take off those boy clothes and get into proper clothes. I gather you have a dress with you. By the way, I’m Carol’
‘Alan or Alice’ I offered
I let us into my room, I was nervous, nobody had ever seen me in girl clothes.
‘Can I see what clothes you have’?
I showed her what I had brought with me.
‘Oh, please wear this one Alice’ she said holding up my cotton mini dress ‘it looks so much like the one I am wearing’
I took the dress and went into the bathroom and changed into the dress and shoes, I shook my hair out from the ponytail and fluffed it out. I was shaking as I stepped back in the room.
‘Wow, who’s a good looking chick then’?
she stepped up to me moved the odd stray hair from my face, I was so near to that pretty face and those luscious lips.
‘Why are you shaking Alice, is this your first time being seen’?
‘Yes Carol, you are the first’
‘Darling how sweet’
She leaned forward and kissed me on my lips, I put my arms around her and kissed her back, we began using tongues, after what seemed like an age, we parted lips, we were both out of breath.
‘I have wanted to do that ever since I fell on the floor, your lips looked so inviting’ I smiled at her.
‘I wanted to hold you ever since I saw you in underwear’ she giggled ‘now lets get your makeup on and I can repair mine, we have lots to talk about’.
I sat in front of the mirror, and applied my makeup, and brushed my hair.
‘You look fantastic Alice’ she said touching up her lippy.
‘I thought you were a real girl, you are very pretty’ I said ‘would you like some wine’
‘Yes please, have you any glasses’?
‘Only those in the bathroom, I wasn’t expecting visitors’
Sitting side by side on the bed, we started chatting and sipping the wine.
‘How long have you been dressing’
‘Since my mum left four years ago’
‘I have been doing it since I was twelve, I am now twenty four, and I love it. Have you ever wanted to go out when dressed’?
‘Yes, I decided today to try it just once, the day after tomorrow at my work’ I went on to explain my job, and how I don’t have much interaction with other people, and how nervous I felt about it.
‘I have been going out dressed for years, never where I live, I travel from my home in Oxford to motels well away from my area, and spend a few days as a girl, I never go out with anyone except a friend who also dresses, I met her online and we meet up from time to time, we go shopping sometimes’
‘Do you like real girls’ I queried
‘You mean am I heterosexual? well sort of , I like pretty girls whether they are cross dressers like us, or real ones’
‘When I first saw you, I thought you were a real girl, I fancied you, I thought you were sexy’ I said
‘Do you find me sexy now’?
‘Yes’ I admitted
‘Would you fuck me, given the chance’? Carol asked
I blushed again, I looked down at my nylon clad legs.
‘Yes’ I stammered ‘but only when you are dressed as a girl’
‘I feel the same, I would love to fuck you, I think you are very attractive’
I knew in my heart that I wanted her, I had been horny all day, and to have this pretty girl beside me was driving me nuts, and it seems she feels the same, I was a bit concerned about having to take her dick in me, but I really wanted to fuck her badly. The wine had loosened my normal feelings and I was prepared to lose my so called virginity so that I could have her.
‘Carol? Would you teach me’?
‘Oh Alice, darling, I would love to’
with that she put her arms around me and we started kissing again, but this time more passionately. She was caressing my leg with her hand, above the stocking top, she reached my panties grasped my dick and gave it a squeeze.
‘I want you to make love to me first, it will help to relax you, but first we have to prepare ourselves, I will nip back to my room and get a douche, it will make it so much nicer’ she left for her room and returned holding a small case.
‘Have you ever used one of these’? She asked
‘No, please would you show me how’
She lifted my dress up and hooked her fingers in the waistband and eased my panties down, I had to raise my bottom to assist her. I was embarrassed knowing she was looking at my dick.
‘Nice size, I will look forward to it’ she grinned
She lifted her dress, I was once again shaking as I lowered her panties down. Her dick popped out, it was around the same size as mine, about six and a half inches, it was shaved smooth, I felt I would like to kiss it.
‘By using this douche, it will stretch your anal tube and leave you squeaky clean inside, now bend over and I will put the tube in and fill you with warm soapy water, just try to hold it all inside for a few minutes, then we do it again twice more’
Carol filled the bag with warm water and put the tube into my bottom, it felt strange having it pushed in me, then she squeezed the bag, I could feel the water going deep inside me filling me up, it was very uncomfortable.
‘Now hold your bottom tight to hold it in’
I felt I was bursting and desperately wanting let it out, I could feel the gurgling of water sloshing about.
‘Now sit on the loo, but hold it in a little longer’
‘It is getting painful Carol, please can I go’?
‘Oh, ok then, as it’s your first time’
The relief as I opened my bowels was great, I finished and wiped myself clean, Carol then bent me over, pushed the tube back in and refilled me. The pain was not so intense now, the second flushing through made me feel empty, she added some oily stuff with the next load, and explained it would lubricate my insides. After the last filling and emptying, I washed myself, I felt so clean and comfortable inside. Carol then proceeded to wash out herself and cleaned up, we both jumped under the shower and very slowly and sexily washed us both down, then she grasped my hand and led me back into the bedroom. We both dressed in sexy underwear, and put on makeup, we held each other close and gazed in each other’s eyes, she smiled as she asked
‘Are you ready darling Alice’?
‘Yes, I think so’ I whispered nervously
She picked up her purse and produced a tube of KY lubricant, squeezing some on her fingers she then ran them all over my dick, she turned over and got on all fours on the bed.
‘You have to put some in my bottom now’
and passed the tube to me, I squeezed some on my fingers
‘Use one finger first and push some inside me, then start using two fingers and get some deep inside me’
I saw her puckered anus, I didn’t think I would get my dick in such a tiny hole. I pushed my lubed finger at her entrance and it popped in, she felt so warm.
‘Ooohh, now work the jelly all around in there’
I carried on, then added my second finger, working them right to my knuckles.
‘Now Alice, now is the time to fuck me, just go slowly’
I wanted her so much, my dick was the hardest it had ever been, I held my stiff dick to her hole, and gently pushed into her, the head of my dick popped in and was clutched tightly by her anal ring,
‘Oh Carol, you feel wonderful’ I said.
Easing slowly into her, feeling the tightness of her rectal tube gripping my dick, I finally got all in her, and began fucking in and out, she felt wonderful, I was finally fucking this pretty girl, she felt much nicer than a real girl, I was holding her by her hips as I gently slid in and out of her beautiful tight bottom, she was rocking in time with my thrusts, I was loving it. I carried on, I could feel my balls tightening I knew I could not last long.
‘Carol? Would you like me to pull out’
‘No, Alice darling, I want you to cum in me’
I pushed in as deep as I could, my dick pulsed and erupted as I pumped my seed deep inside, I cum so hard I could see stars. I rested with my dick in her, I was breathing hard, I so enjoyed that fuck. My dick was wilting and finally dropped out, she handed me some tissues.
‘Well, Alice, how do you feel’? she said rolling onto her back and looking up to me.
‘Fantastic, I think you are the best fuck I have ever had’
I looked at her sweet face, smiling at me, I could easily fall for her.
‘See this’? she said waving her hard dick at me ‘it wants you badly’
I knew the time had come for me to experience being fucked, although I was worried about my first time, I still wanted to give myself to her.
As I assumed the position on my hands and knees, I realised I actually wanted her to fuck me.
She kneeled beside me and spread the KY over her dick, then went behind me, I felt her finger at my anus, I jumped as it entered me
‘Don’t worry darling, I will be very gentle with you, just try to relax’
I could feel her finger loosening my ring, the second finger went in, it hurt a bit at first, then as I relaxed the pain went and her fingers were deep in me.
‘Now is the time Alice darling’
I felt pain as her knob entered me, but I knew it would gradually go, very slowly she entered me deeper and deeper, I had a sort of burning sensation and pain, I felt so full, her thighs touched the back of my legs, I knew she was fully in me now, she began little fucking motions in and out, the pain was gone and now I could feel her sliding smoothly inside me. I was being fucked like a girl, I hated to admit it, but it was now feeling good, I liked the feeling of her dick inside me, I backed up to her as she went forward, we got into a rhythm. I have now given my virginity to this lovely Carol, I am so pleased, I was enjoying being fucked by her.
‘Do you want me to pull out darling’
‘No Carol, I want it in me, I want to be yours completely’
I felt her begin to swell inside me, I could swear I felt her sperm travel up her dick then flooding my bowels with her essence. I was a girl now, her girl, I was dressed like one, I felt like one, and just been fucked like one, and I loved it.
‘Thank you so much Alice, you have given me your virginity, you were so tight at first, a bit more loose now though’ she giggled ‘how do you feel’
‘Wonderful, I feel so girlie, and you make such a good lover’
‘Well, I think I should give you another new experience’ how about straightening ourselves up and walk to the late night shop just up the road and get another bottle of wine, it’s only a hundred yards’
‘I have never been out before as a girl’
‘We will be together’
‘Ok’
‘Leave your panties off and keep your bottom clenched’
We fixed our makeup, got dressed, I put the key in her purse, and we went out. I was holding her hand tightly. After walking about half way, I began to enjoy the freedom and the clip clop of our heels, the swish of my dress, and the feel of nylon sliding on my legs.
We reached the shop, a sort of mini market, I found the wine while Carol was looking around. We met at the cashier’s desk, Carol was holding another purse. After paying, Carol handed me the new purse.
‘Here Alice, a little present to remember this day’
I gave her a big kiss on her lips
‘Thank you Carol, I will never forget today, you have changed my life, I feel so much more confident now’
We held hands on the way back, I felt a trickle run down my leg, ‘oops’ I thought, that is her cum, I giggled
‘What’s funny girlfriend’?
‘My bum is leaking’
we both laughed out loud
‘Come on gorgeous, I want to refill it again’
Once back in the room, we hugged and kissed passionately, I reached behind her and slowly unzipped her dress, we broke the kiss, she shrugged it down to reveal her silky underwear, she stepped out of her fallen dress on the floor, she stood in front of me in her bra and suspenders, if it wasn’t for her dick sticking out from her body, she would be a very sexy girl. I wanted to fuck her again, but I also wanted to be fucked by this lovely creature. She helped me out of my dress, as we got close for another clinch, our dicks rubbed together, we both looked down and giggled, I held hers and she held mine. She looked me in the eyes and whispered
‘Can I fuck you first this time, I do want you so badly’
‘I am all yours darling Carol, I loved you fucking me, I want to feel you in me again’.
‘Lay on your back and put the pillows under you, I am going to make love to you missionary style’
I got into position, she squeezed some KY and lubed us up, she lifted my nylon clad legs to her shoulders, I looked up at her pretty face as she pushed her dick gently into me. I hardly felt any pain while she fed more of her dick into me. That nice feeling of fullness as her thighs touched the back of my legs, then she began fucking me with long slow strokes. She smiled down to me
‘Alice darling, I am in heaven, you are such a beautiful girl and I am fucking you, I could easily fall in love with you’
‘I feel the same way Carol, you are a pretty girl and sliding deep in me, making love to me, I never dreamed it would be like this’
Slap slap as her thighs met my buttocks, slurp slurp as her dick slid in and out, I was being well and truly fucked, her movements began speeding up, she was grunting as she fucked harder, her dick was swelling, then I really did feel the throbbing of her dick as it unloaded her sperm deep inside me. It felt so good and I had satisfied my lover. After she started to wilt in me, she leaned forward and kissed me hard.
‘Alice darling, I am falling in love with you, I can’t help it, I have never felt this way before’
‘I feel the same Carol, you are the best thing that has ever happened to me’
Her dick plopped out, we quickly used tissues to clean each other.
‘Now Alice’ she said grasping my hard dick ‘it’s my turn to be on the receiving end, I want this inside me’.
We exchanged places, I used the KY then I lifted her legs to my shoulders, her nylon clad legs felt so good against my neck, I placed my dick and eased into her warm inviting body. Gazing in her eyes I went gently fully into her, she smiled back.
‘Mmm, I love being inside your body’ I whispered
I began fucking this sweet girl, I ran my hands up and down her silky legs, I stroked her limp dick and cupped her now empty balls, I had never known anyone as intimately as this before. I was fucking her for what seemed like ages, I was enjoying every second, she seemed to try and draw me in with a sort of gripping with her anus.
‘Do you like that darling’? she said ‘I am trying to milk your lovely dick with my bottom’
‘Mmm, feels so nice, you will have to teach me that’
I picked up the pace, my balls were aching for release
‘Oh Carol darling, ugh I’m cumming, ugh so deep, ugh in you’
I grabbed some tissues, as I leaned to kiss her my dick plopped out, I wiped us both clean.
‘God, that was fantastic, you are the best fuck ever, far better than a real girl’ I said as I lay on top of her, kissing her face all over.
The next thing I knew, I woke up with a start, my left arm had pins and needles, I looked over, and a warm glow came over me as I recognised Carol beside me. I had only met her yesterday, but we had fucked each other twice, I had given my virginity willingly to a pretty transvestite. I looked at the clock, nearly six. I eased my arm from under her, then quietly crept to the bathroom, my bum was a bit sore and was a bit crusted with dried cum, I ran the shower, removed the rest of my clothes and got under the warm spray, I soaped myself over and was bending to wash my legs and feet,
‘Gotcha’
I was suddenly startled when something touched my bum, I slipped and sat down hard on the tiled floor, I looked up to see Carol grinning at me
‘You frightened the life out of me, you cow’ I grinned back ‘please help me up’
We stood face to face, our makeup ruined and running down, we kissed and held each other tight under the warm water, both our limp dicks dangling together.
‘Please can I soap you’ I asked
She stood with her legs apart as, run my soapy hands all over her
‘What a nice shaped bum you have’
‘You should know, you have been in there enough’ she said laughing
‘It feels nice too’ I said cupping her buttocks in my hands.
‘Are you feeling horny this morning Alice’?
‘Well..yes’
‘I will only do it if you wear some girlie underwear, at least, and also some makeup, I did say I am sort of heterosexual, I don’t fancy men at all’
‘That, I must agree with you, I met a very sexy blonde girl yesterday, and yes, it was because she was girlie that I wanted her’
‘Ok cutie, let’s get it together then lets get together’ by the way she asked ‘what time do you have to be at work’?
‘Around nine fifteen, only two miles from here’ I answered
we put on stockings, bra and padded them out, I loaned her a baby doll top, I put on my corselet, both shared the mirror and added our makeup, both of us giggling like silly schoolgirls. We looked at each other up and down, both our dicks erect with anticipation.
‘I will be bottom first Alice’ as she lay on the bed ‘do you want me this way or on my knees’?
‘This way, so I can stroke your legs and see your pretty face while I make love to you’
She put the pillows under her and passed me the KY, once I had prepared us I looked down, she was so pretty in her baby doll top, she smiled as I eased into her,
‘Mmm, you look and feel so good’
‘How does this feel, my sexy girl’?
I could feel my dick being squeezed and drawn into her,
‘That feels wonderful, you will have to teach me how to do it’
‘You have pull your insides as if you were trying draw in the dick and squeeze your anus at the same time’ Carol murmured.
‘If you carry on doing that, I won’t be able to hold back’ I croaked
‘C’mon baby, fill me up, get me pregnant’ she grinned
I began pounding her lovely body, I got to the point of no return then emptied my balls into her.
‘Wow, you are one helluver fuck Carol’ I gasped
I wiped us with the tissues.
‘Thank you sweet girl’ she said rolling onto her back ‘I want you to kneel astride me’
I did as she asked, she squeezed the last of the KY getting us ready
‘Lower yourself on me Alice darling’
I grasped her dick behind me and guided it as I lowered down onto it, I was finding it easy to take her dick in me now, and it felt nice as I slipped further down onto her lap.
‘Are you comfortable’ she murmured sweetly
‘Mmm, yes’
‘Try to grip me with your rectum’
Although I had her dick in me and had stretched me, I tried gripping her with my anal muscle.
‘Do it harder’
I tried clamping her dick as if to part it in two.
‘That feels great, now try drawing me in at the same time’ she said putting her hand on my abdomen.
I started using my inner stomach muscles attempting to get her deeper in me at the same time as trying to cut her dick in half with my rectum.
‘Wow, you’ve got it, it feels so much better than a female pussy’
I smiled at her, then lifted my bottom up a few inches, Carol began fucking up into me furiously. I loved the feel of her dick sliding in and out while watching her smiling face below. I continued using my clenching and drawing of her dick, it seemed to enhance the exquisite feeling of being fucked. She was now thrusting hard, her dick swelling and began the pulsing as she shot her load into me.
‘That, darling Alice, was most definitely the best fuck I have ever had’ Carol panted.
‘I hope I am not turning gay, but I loved every second of it too’. I said concerned.
‘More like being a lesbian, we are two sexy girls making love, tell me, would you like to see a man doing you’?
‘No, when I think of it, I would hate the idea’.
‘Come let’s get sorted and grab some breakfast’
We undressed and dived in the shower naked, Carol was right, once the clothes and makeup came off, I did not fancy her at all, in fact I felt embarrassed seeing a man in my shower.
Carol got dressed in her girl clothes and put makeup on, I had to put on my boy clothes because I would be off to work. We had breakfast as a boy and girl, she explained she worked flexi time and tried to do a ten or twelve hour day and build up two or three days off, then off to a motel to be a girl.
‘I have not come out at home because my mum and dad would have a fit, but I do love shopping, going out in public and being accepted as a girl’
‘You certainly look like a pretty girl, if I hadn’t seen your dick I would never have guessed. My dad doesn’t know I dress either, I usually dress up when he is working, I use my mums clothes, they fit me perfectly, she left loads of really nice things behind, even her makeup and perfume’.
‘Tomorrow you said you were going to work dressed up and it would be your first time out. Well all you have to remember is that be confident, you are a girl, you look like a girl, and, by the way, you look very sexy also you have great legs’
We chatted over our coffee, swapped phone numbers and email addresses, just as we parted Carol hugged me then kissed me.
‘Ugh, I just snogged a man’ she giggled ‘we have to keep in touch, I will miss you, and let me know how you get on about tomorrow’
‘I will miss you too Carol, I feel I have met my soul mate with you. I will call you this coming weekend, ‘bye’.
‘’bye lover’
I packed my things and loaded the car. I made it on time to work at nine fifteen. Time seemed to drag, but I completed my work early afternoon. I made out my report then passed it to the office manager, he thanked me for my efforts, and said how pleased he was about how his system was working smoothly and had speeded up.

Later that afternoon, I arrived at the motel in Hampshire, once in the car park I let my hair down, removed my jacket and tie, put on a little lipstick then went and signed in as Alice Smith.
Then in my room, I carefully hung up my lady business suit and sorted my underwear and shoes for the next day. I showered and shaved my body and legs, I was very lucky that I had little body hair it was blonde, very fine and sparse. I blow dried my hair and gave it a little curl, I painted my nails, both hands and feet in a dark pink, dressed in matching bra and panties, corselet, stockings, made up my face and made a coffee from the service pack in the room.
Using my mobile phone, I contacted the manager of the company I would be visiting the next day and arranged to be there around nine am.
I was wishing Carol could be here, I felt I could do with some moral support, I missed her a lot, I knew I was falling in love with her, and the sex with her was out of this world.
I put on a cotton dress and short jacket, three-inch heels, grabbed the new purse Carol had bought me. As I reached for the door, I stopped, ‘well Alice, this is it’ I said to myself ‘my first outing alone as a girl’ I went out the door and made my way to the restaurant. It was fairly busy, only a few tables empty, I felt everyone was looking at me when the waiter came up and asked,
‘Table for one miss’?
‘Yes please’ I answered.
He seated me almost in the centre of the tables, I would have preferred being on one side, ‘never mind’ I thought, at least I would be on show for my initiation among people, I must try to act like a lady. I placed my order, and furtively glanced around, nobody seemed to be looking at me except for a young man over one side, as our eyes met he smiled, I looked down at my manicured hands. My order arrived, I ate as delicately as I could and not looking around. When finished I declined coffee, I thought I would have a drink at the motel bar, as I stood , I noticed the young man had already gone. As I entered the lounge bar, he was there seated on a stool at the bar. I tried to avoid him by going to the far end. I ordered a dry white wine, when it arrived I reached for my purse.
‘That’s ok miss, the gentleman over there paid’ he pointed to the young man.
I looked over to him, he smiled, I lifted my glass smiled back and mouthed ‘thank you’. I carefully made my way to an empty table with comfy armchairs.
‘Please may I join you miss’
I jumped
‘I am so sorry I startled you’ the young man said
‘I was deep in thought, I was not expecting anyone’
‘May I’? he indicated the chair opposite
I nodded
‘My name is Chris’ he said holding out his hand smiling
‘Alice’ as I shook his warm hand
‘On holiday’?
‘No just work’
‘You look like a model or something’
‘Thank you, but no, I am an IT engineer’
‘I never would have guessed, you should be in front of a camera. As for myself I am a salesman for office equipment, I come from Southend in Essex’
‘Brentwood Essex, I live with my father’
‘Not married’?
‘No, not even thinking of it either, I am very happy as I am’
He ordered another round of drinks
‘Please let me pay this time’ I asked
‘Certainly not, it is my privilege’
We chatted about all sorts of things, he seemed a nice person, he was single and not in any hurry to settle down, he asked me a couple of times whether I was in a relationship or not, but I avoided a direct answer, just mentioning that I had met someone a couple of days ago and was hoping to see them again sometime.
He went to order more drinks
‘Not for me thanks, I want to keep a clear head for tomorrow, especially as it is a new customer’
‘Will you be staying tomorrow night’?
‘Probably not, unless I run into any nasty problems’ I stood and offered my hand ‘it’s been nice to meet you Chris’
He shook my hand ‘Alice, I do hope we bump into each other again’
I smiled sweetly, then left and returned to my room. I knew by his manner that he would love to have got into my knickers. He was the first man that I had even found slightly attractive, ‘god, I am thinking like a girl now’. I undressed, washed, cleaned my teeth and popped into bed wearing the baby doll that Carol had worn this morning, thinking of her I drifted off to sl**p
I woke up gradually, I felt good as I stretched, then I realised that today I was going to work as Alice, I looked at the clock six-thirty, I quickly showered, had a very close shave, I usually only needed a shave every third day of my fine soft blonde beard, but today was special. I blow dried my hair adding the curl, I was meticulous with my makeup, I used a tight bikini pouch which pulled my dick under me, which once I put my panties on gave no sign there was anything there. Once fully dressed I scrutinised every detail of myself carefully, I looked one hundred percent girl, I even fancied the girl in the mirror looking back at me.
I was eating my breakfast when Chris came in
‘Good morning Alice, you are looking great today’
‘Morning Chris, and thank you’
‘May I join you’?
‘Yes of course’
He went off to get his meal, as I watched him walk to the servery, I wondered what it would feel like to be kissed by a man, I knew that kissing Carol was really nice, but it did feel I was kissing a girl, is a man different? I thought.
‘I’m famished’ he said sitting opposite
His table manners were very good, he did not talk while eating and he chewed with his mouth closed, when he finished, he put his knife and fork together neatly on his plate, ‘mmm, he was nice looking, here I go again’ I thought, ‘thinking like a girl’.
He came around the table, offered me his hand
‘Coffee in the lounge’? he asked
I took his hand and rose from the chair
‘That would be nice, thank you’
We walked holding hands to the lounge, he led me to a table,
‘I’ll get them, how do you like it’
‘Just a hint of milk and one sugar please’
Again I watched him as he walked away, then when he was returning he was concentrating not to spill the drinks, I noticed the outline of his dick in his trousers, half hard and a fair size, ‘once more I was thinking like a girl, I have got to stop it, I am not gay’ I was getting annoyed with myself.
We sat sipping our drinks, Chris put his hand on mine
‘Alice, I really want to see you again, I would love to take you out and wine and dine you one evening’
‘Thank you Chris, that is a nice offer, but I don’t think we would be suited’
‘I think you are the most attractive and sexiest lady I have ever met’.
‘Please don’t spoil the day for me, you are a very nice handsome man, I like you, but I am afraid it would never go further than that’.
‘Can we at least be friends’?
‘That would be nice, but look, I have to go, I don’t want to be late for a prospective new customer’
‘Here, take this, please call me’ he said handing me a piece of paper
It had his home and mobile phone number and email address.
‘I will. Goodbye Chris’
I collected my laptop and tools from my room and set off.

Arriving at Santex, the security guard pointed to the visitors parking. I parked and collected my things, pinned my identity badge to my jacket, I felt so nervous as I entered into the reception, I handed my security card to the receptionist, she scanned it.
‘Welcome miss Smith, you are expected by Mr Paul Copeland the senior office manager, would you go to his secretary on the fourth floor, she will be expecting you’ as she handed back my card.
I took the lift and found Mr Copeland’s secretary, she was ready and waiting for me.
‘Hello miss Smith, please go in, Paul is expecting you
‘Thank you’ I said entering the office
‘Ahh, miss Smith, or may I call you Alice’?
‘Alice would be fine Mr Copeland’
‘Please call me Paul, I hate formalities’ he handed me a batch of papers ‘these are our problems with our computer network system, I am sure you wish to study them, so I have arranged a private office, a computer and terminal, for you, my secretary Jean will show you around’ he pressed a buzzer ‘Jean? Alice is all yours now’.
We shook hands. Jean was waiting for me.
‘Hi Alice, you have an office on this floor, I will show you, and please if you need anything please call me’
She showed me the coffee machine and toilets and led me to a room.
‘I will give you a call at twelve-thirty lunch time’ she showed me a direct call button to her desk ‘anything at all, just call’ she grinned
‘Thanks Jean’ I smiled back.
I removed my jacket and sat in the comfortable swivel chair, plugged in my laptop, booted then set the diagnostic programme to run. I began reading the papers Paul had handed me, usual problems, the odd crash, running slow, memory hiccups, general things until I noticed that Santex had been pre-empted on tenders for estimated costs a few times by other companies. I quickly stopped the diagnostic programme and started a programme I had made, I watched the screen, a few anomalies began to show up. After an hour I had a list of peculiar happenings. I used their computer to follow trails on the internet, a further hour, I found that there was a company called Unix corporation who had access to Santex main frame they had also included a warning system to let them know if Santex had alterations or modifications made to their computer system, luckily I had stopped the authorised diagnostic programme, as once it had got into Santex system, Unix would have been notified, but my own programme could not be detected. ‘I better tell Paul’ I said to myself. I pressed the button for Jean
‘Hello Alice, can I help’
‘I have some sensitive information I ought to pass to Paul’ I said
A minute later Paul entered.
‘Do you have a problem Alice’?
‘No, but I think Santex have, do you know a firm called Unix corporation’?
‘Yes of course, they have been our hardware and software service company for over two years, the reason your company was called in is because they couldn’t get here for another week and your company has the highest security. Why is there a problem’?
‘They have left a small programme running in your system, it gives them access to all of your information, and also of any alteration of your software, even a diagnostic check would alert them. I had just started to run the programme when I saw your company had been pre-empted on several occasions on your estimated tender quotations, that means that somehow a rival company was getting fore knowledge of your pricing. I stopped the diagnostic programme immediately, and started one I devised myself for detection, I found the offending link, I made a fictitious entry to purchase one hundred cards for an estimated one hundred thousand, purely so that keywords would send the message, and by using my laptop computer, I was able to follow the message through two drones, which then directed it to the final web IP address. Which with a bit of checking, I found it to be Unix.’
‘bl**dy hell, oops, sorry Alice, that means the whole of our database is breached, can you remove the offending programme’?
‘Not without them knowing. I would suggest you find who commissioned them in the first place, you may have someone who has been planted here’.
‘I will get on it immediately’ Paul said rushing out
I was a bit stuck, if I started sorting out Santex problems, it would notify Unix, so until Paul gave me the OK to remove the offender, I could only do some unobtrusive checks. A little while later, Jean popped in.
‘Hi Alice, ready for lunch’?
‘Mmm yes’
I put my jacket on and we went in the canteen. After sitting at a table with our lunch, Jean said
‘I don’t know what you said to Paul, but he looked really serious and went straight on the phone to the MD’
‘Oh, it’s nothing really, you will find out later’
We chatted over lunch, she was surprised I didn’t have a boyfriend
‘A girl who is sexy and attractive like you, you should be fighting them off’
‘In between at the moment’ I replied
‘Alice? I am sorry to disturb your lunch, but would you have a word with the MD please? It is very important’ Paul asked anxiously, ‘and Jean would you come too please’?
We went to the Managers office, there was a middle aged gentleman in there,
‘Andrew, let me introduce miss Alice Smith’ Paul said ‘Alice this gentleman is our managing director Mr Andrew Snelling’
‘Pleased to meet you Alice’ Andrew shook my hand ‘Please call me Andrew. Well young lady, it looks like you have stirred up a hornets nest, I can’t thank you enough for bringing this to light, Andrew has told me how you used your homemade checking programme so as not to alert the enemy, so to speak, also how you traced them. I have made arrangements with the authorities to enter their premises and check their computers and main frame, but that will happen this afternoon. I will contact your office and ask if it is possible for you to come back tomorrow, to finish your work’?
‘Thank you Andrew. Is there anything I can do this afternoon’?
‘Not on our computer system, we are only using them for minimal work until their system is quarantined, so you may as well have the rest of the day off’.
‘I will see you all tomorrow then’.
I had dropped myself deeply in the mire, he was going to phone my office, who have not got an Alice on their books, ‘shit’ I thought, I will be found out and lose my job. On the way back to the motel, I stopped off at a pharmacy and purchased a colonic douche, after being with Carol I liked the feeling of being clean inside, back at the motel I carefully removed my suit and hung it up. My mobile rang, I started to shake with nerves when I answered it.
‘Hello’ it was my manager,
‘Good afternoon MISS Smith, I have just come off the phone from Andrew Snelling, I have agreed to let you go back tomorrow to finish off your work. I don’t want you to explain now, but I want you in my office on Monday morning dressed exactly how you were this morning at Santex, I mean exactly. Then I will need explanations why, then, how come you make your own programme and run it on our clients system. In conclusion, Mr Snelling thinks very highly of you and praised, in his words, quote ‘a very attractive intelligent young lady’ unquote. And from me, thank you for doing a good job, See you on Monday Alice, ‘bye’
I didn’t know what to think, I had been reprimanded and praised, I do hope I won’t lose my job over it all. I started to cry, I was in a bit of mental turmoil.
Knock. Knock. on my door who on earth can that be? I opened it to find Chris standing there.
‘Wow you look…oh Alice your crying’
He rushed in and hugged me tight, I realised that I was only wearing my underwear, he gently wiped my tears with his finger then kissed me, I was not expecting that, his tongue was probing my lips, I was off guard and let it in, the kiss lingered I was enjoying it now, both our tongues probing each others mouth, I could feel his dick pressing on my stomach. Finally I pushed him away from me.
‘No Chris, I don’t want this, I am sorry but you would not understand’
‘From the way you kissed me back, I know you enjoyed it, after all we are both adults, what objections do you have? I think you like me, I know I like you very much and you look fantastic, what is it that I would not understand’?
I sat down, put my head in my hands
‘You would hate me, I want you to leave’
I started to cry again.
‘What is troubling you Alice, I would really like to help if I possibly can, please give me a chance’.
‘It’s not you Chris, it is me and what I have done’.
‘I beg you Alice, please tell me’
‘I will say one sentence, then I think you should leave’
‘Go on, please’
‘I am not a girl’
‘Of course you are a girl, may I add, a very sexy girl’
I stood up lowered my panties, put my hand under and removed the plaster so my dick appeared, the look of shock on his face, his eyes opened wide.
‘Now you can leave Chris’. I said
‘I…I still want to stay, I want to hear your story, and I still think you are very sexy’
I told him of how I dressed at home, and in motels and that this time I met another transsexual girl, also that I had decided I would go out for the first time dressed and go to work, how the customer phoned my boss and how my boss wants me in his office dressed on Monday.
‘And that was why I was crying, because I could lose my job’
I had not told him about my work.
‘Can I still wine and dine you this evening Alice’? he asked
‘You want to? Even though I am not a girl’?
‘I would be proud to have you on my arm, I still think you are gorgeous’
He stood and came over to me, grasped my hand and lifted until I stood half naked in front of him, he lowered his face to mine and we kissed, it became a passionate kiss, my dick became hard. After a while we broke the kiss and he lowered himself onto his knees, he clasped my dick then kissed all around it, then sucked it in his mouth, his head bobbing back and forward, with one hand he was caressing my balls, the other was stroking my nylon clad legs, he licked the underside of my dick as he sucked it in his warm moist mouth, I was enjoying a blow job from a man, I had to warn him
‘I am going to cum’
He held me in and sucked harder, I felt my dick explode into his throat, he gulped and gulped, swallowing all my sperm. My knees started to buckle, as I slowly lowered to the chair, he licked my dick clean.
‘I said I wanted to stay, didn’t I’?
‘You were so good, you must have done that before’
‘Honestly, that was the first time I have ever even touched a dick, I know what girls have done for me, so I just copied their method’
He leaned forward and kissed me tenderly, and whispered, I want to make love to you Alice’
I began thinking, if I let him, it means I am letting a man into me, which therefore makes me gay, but I would still like his dick in me.
‘Only if you take it slowly and wear a condom, I will have to get ready first’
I went in the bathroom and gave myself a douche, I realised then that I wanted to be fucked as a girl by a man. I returned to the bedroom.
‘Oh Alice darling, you look fantastic’
He quickly undressed, his hard dick sprung out, larger than Carols, I placed my hand around it kissed his knob, licked up and down, it was very hard. He lifted me up and carried me to the bed, I got on my hands and knees, my bottom in the air. I looked back as he put on a condom.
‘There is some skin moisturiser in the bathroom, I will need some in me first’
he went and got the bottle, his dick waving up and down as he walked, I felt him lubricating me, using his fingers, then his dick pressing at my anus, I relaxed, then he popped inside me, his dick stretched me.
‘Gently please Chris’
He slowly pushed into me, it was a bit painful, deeper and slowly deeper, I felt his thighs against the back of my legs, he stopped moving, fully in me.
‘God you are tight Alice, but you feel wonderful, are you ok’?
As an answer, I gripped and drew him like Carol had taught me, then wiggled my butt.
‘Wow, that’s fantastic’ he gasped
He began fucking me, withdrawing and sliding back in, any pain had gone, all I could feel was a nice large dick moving inside me.
‘Can we change position? I want to look at your pretty face’
He withdrew from me, I felt so empty as I rolled onto my back, I placed the pillows under me lifting and offering my bottom to him, he lifted my legs to his shoulders, then he leaned over and put his dick back in, he smiled. I smiled back at his handsome face.
‘You are so pretty Alice’
He was soon pumping in and out of me again, he was stroking my half hard dick, I was really enjoying my first man making love to me, he gritted his teeth then I felt his dick pulsing inside. At that moment I knew that I was bisexual, I liked being fucked, and I liked fucking, especially Carol.
Chris withdrew his dick, leaned and kissed me tenderly.
‘You are amazing Alice, that was the best fuck I have had for years, I have never been with anyone but female before, you are my first cross-dressing girl’.
‘You, darling Chris, are only the second person who has fucked me’.
He removed the condom and went to the bathroom, when he came back he said
‘Are you hungry yet’?
‘Yes I am a bit, I never quite finished my lunch’.
‘I will call back for you, is an hour long enough? Then I will wine and dine you’
‘That’s fine, it will give me time to get ready’
He held me close, we had a tongue fighting kiss’. He got dressed.
‘God, you are so sexy’ he said as he left.
An hour later, I was dressed and made up, just checking my purse Carol had bought me when Chris arrived.
‘Wow, you are a real knockout Alice, fancy a quickie before dinner’? He said grinning.
‘You have to feed me first’ I said pecking him on the cheek
‘Does that mean I am on a promise then’?
‘If you feed me first and will still want me after’.
‘You can bet on it, I can’t wait to get back in your pretty panties’
‘I reckon you would look good in them, but you would have to shave all over’ I grinned.
We had a good romantic meal, he was very attentive and kept whispering sweet things to me. We danced a few slow ones, his dick was constantly hard, I grabbed it a couple of times when no one was looking.
‘I want you so badly Alice, can we leave soon’?
‘Ok, but I have a long day tomorrow, so you must leave by midnight, until then, I am yours’
He drove back fast, no sooner had we got in the room he was stripped off, he helped me off with my dress and shoes, I took my panties off letting my stiffy free, once again he gave me a very good blow job and swallowed the lot. He put on a condom and once lubricated me with moisturiser, he gently entered me with my legs on his shoulders, he is a considerate lover, making sure I was comfortable as he fucked me like a woman. I loved having his dick sliding in and out of me, I felt very girlie being made love to. His face took on an urgent look, he thrust into me harder, his dick throbbed as it unloaded his man juice. He pulled out his softening member, removed and tied off the condom, wiped his dick with a tissue. We went into a long lingering kiss, he was holding me close, and whispered,
‘I could easily fall for you’
‘Now Chris, you know that is impossible’
‘But you are so sexy and feminine’
He started kissing my neck then gradually down my body, he put his tongue in my belly button, then proceeded down my leg, he sucked each painted toe through my stockings, to the other foot, up that leg, he turned me on my front and tongue fucked my rectum, this was turning me on, I was getting a hard on.
‘Would you like to fuck me’? he asked.
‘Do you want me to’?
‘I wondered what it would be like’
‘I’ll tell you what, if you don’t like it or if you want me to stop, just say, but you would have to give me another blow job instead’
He passed me a condom, I prepared his rectum with moisturiser and managing to get two fingers in him. His bum was in the air ready. I pressed my dick at his entrance,
‘Just relax, Chris’
The head of my dick popped in
‘Ow’ he yelped
‘Sissy’ I teased
I eased in very slowly, he grunted a little as I got deeper, finally I was fully in him, I rested a while to let him get used to me, I could tell that the pain was going when he moved back on me. I began fucking with small movements. Although I did not find it sexy to fuck this man, the warm tight grip on my dick felt great, I found by closing my eyes and imagining I was fucking Carol, gave me extra lust, and I began fucking harder. After a while, I could not hold back and shot my load. I slowly removed my wilting dick, making slurping noises on the way out.
‘I now know how you feel, once the pain subsided I rather enjoyed it, it was my first time being fucked, and by a sexy girl as well’ Chris smiled
I removed the condom, and wiped my soft dick
We held each other close, I whispered in his ear
‘Fuck me’
He didn’t need telling twice, in record time he had me on my back and moisturised, his dick sheathed, and was entering me. I was getting used to his large dick, it didn’t take long before he was fucking me with the full length. It was a long leisurely fuck, no urgency, both savouring good sex. Eventually his dick swelled and pumped out his load. After he sorted himself out, we just lay in each other’s arms just as normal lovers would. I looked at the clock, just gone midnight.
‘I am going to turn into a horrid witch any second’ I said pointing to the clock.
‘Sorry darling, I was feeling so happy being with you’
He got up and was dressing
‘Can I see you again Alice’?
‘I am not sure, it’s according to how my work goes, when do you have to leave’?
‘Friday morning after breakfast, I am working all day tomorrow, so I have one more night here after tonight’
‘Give me your number at breakfast’
‘Ok darling, see you there’
He gave me a loving goodnight kiss and left.
I slept like a log, the alarm went off startling me to the morning, in the shower I shaved all over. Dressed in my suit I looked in the mirror checking every detail, ‘yes’ I thought ‘I do look good’, as I walked to breakfast, my bottom was a bit tender reminding me of the good fucking I had the night previous.
‘Hello beautiful, how are you this lovely morning’ Chris said beaming as he came to my table
‘Happy now I have seen your handsome face’ I smiled sweetly
‘I bet you say that to all the men’
‘No, only the ones that have fucked me silly half the night’
‘You said I was the only one’
‘And you are the only one I have said it to’
We both burst out laughing. He gave me a card with all his details, I finished my breakfast
‘I have to go’ I kissed him on the cheek
I arrived at Santex, went through the security check in reception, made my way to Paul’s office
‘Hello Alice, go right in, they are expecting you’ Jean piped up cheerfully
‘Hello Jean, thanks’
I was nervous of what to expect, I knocked and entered, Paul and Andrew were there
‘Ahh, Alice Smith’ Andrew stepped forward and shook my hand warmly ‘you are our angel, you have probably saved this company many thousands with you discrete findings, you will have to excuse me, I feel a bit ragged today, I have spent most of the night with the fraud squad and police. Unix has had all their computers, mainframe and peripherals confis**ted and taken to police forensics for examination. We will keep your company informed of the outcome. As head of Santex I offer you our heartfelt thanks’
‘Thank you Andrew, it is only part of my job’
‘I hope to speak to you again before you leave today’
‘May I get to finish my work now’?
‘Yes it is safe to carry on now’
I smiled and left the office
‘Catch you for lunch at twelve thirty Alice’ Jean said
‘Look forward to it Jean’
I set to work, I ran the diagnostic programme, found many faults and anomalies, made a folder to hold the rarely used programmes, and generally cleaned up the whole networked system.
‘Hi Alice, fancy a bite’ Jean put her head around the door.
‘Goodness is that the time, be right with you Jean’.
Once seated with our meals, Jean remarked
‘Well, who’s the flavour of the month then? Andrew and Paul haven’t stopped talking about you all morning’
‘I was just lucky I noticed it’
‘Not only your work, they both fancy you’?
‘Oh no, that’s embarrassing’ I blushed
‘They reckon you are really sexy’
My bottom was still a little tender from last night, but it still gave a twitch at the thought of men wanting to put their dicks in me. Wow, if only they knew, I would be thrown out so quick my feet wouldn’t touch the floor. I was beginning to regret dressing as Alice.
‘I’m not sexy, I am just me’
‘Well, even I think you’re sexy, don’t get me wrong, I am not lesbian, but there is something about you that is very attractive’
‘Now I really am embarrassed’ I felt my face blushing
I thought that she was sexy and I would love to fuck her, but she would run a mile if I got my dick out.
‘Come let’s have coffee in the lounge’ she urged
I was getting aroused and it was uncomfortable with my dick taped back, but thankfully the chat went off sex and became girl talk, clothes, makeup etc.
‘Ah well, back to work’ Jean said ‘catch you later Alice’
‘Yes, see you’ I replied
I settled down in my loaned office, I had about two hours work at most, I concentrated on what I was doing. Finally I finished. I went to Jean and asked to see Paul, she called through the speakerphone
‘Send her in Jean’ Paul’s voice replied ‘Ah Alice, how are things going’?
‘All finished Paul, except for rebooting the system for the changes to take effect’
I could see by his eye movements that he was mentally undressing me, I smiled to myself.
‘Jean’? He called ‘can you arrange a short shutdown on the computer system please’ then to me ‘please take a seat Alice’
Keeping my knees together and adjusting my skirt, I sat carefully on the offered chair. Two minutes later, Jean called
‘Ready Paul’
‘All yours Alice’ he said
I went back to the office and rebooted the system, once back, I checked everything was working ok, no problems running smoothly. I gathered my things, then back to Paul’s office.
‘All finished Alice’? Jean asked
‘Yes thanks Jean’
She ushered me through the door.
‘All ok Alice’?
‘Yes fine thanks Paul’
‘I can assure you that your company will get a glowing report concerning your work, I can’t thank you enough for your efforts’ he shook my hand warmly ‘goodbye Alice, I am pretty sure we will see you again’
I groaned inwardly
‘Goodbye Paul, I am glad I was able to help’
Jean came to the lift with me, she turned me and kissed me on the lips, I was helpless holding my cases in each hand, I kissed back.
‘Goodbye sexy girl’ she whispered
I smiled and blew her a kiss as the lift doors closed. once back in my hotel room I looked at the clock, four thirty, I didn’t fancy the drive home as I would hit the rush hour, and I was a bit weary from the day, so I decided to leave tomorrow after breakfast. I stripped off and had a shower, gave myself a douche, once cleaned inside and out, I put on the corselet, panties, bra, stockings, mini skirt and blouse. I put on new makeup and brushed my hair. I felt and looked good, hopefully Chris will be around later and give me a good fucking. At six o’clock, I reckoned I will be spending the evening by myself, as I grabbed my purse
‘knock, knock’
An attractive brunette woman in a short dress was standing there, I was just about to ask what she wanted, when I recognised it was Chris.
‘Oh my god, it’s you Chris’
‘Let me in quick’ he said as he rushed by me
‘Stand back, I want to see you, why this’? I asked pointing to him
‘You are one of the most sexy girls I have ever met, I love fucking you, and I enjoyed you fucking me last night. You did say something about me wanting to get in your panties. I got to thinking, what it would feel like dressing as a girl, so I did a bit of shopping’.
‘Actually you don’t look too bad, and I like the hairpiece’
‘I have shaved all over, I am a bit unsteady with the heels, but I need you to make up my face’
‘Come, sit over here, I will make you pretty’ I pointed to the vanity stool
‘Can you call me Christine now’?
I kissed her lips
‘Hi Christine’
I started making up her face, after twenty minutes she looked very attractive, I turned her so she could see in the mirror.
‘Coo, I look really nice and girlie’
‘So good that I will have to fuck your brains out later’ I grinned at her. ‘Now stand and walk about’
She was unsteady with her heels, but she was definitely passable as a girl.
‘Keep practicing, and take shorter steps’
‘It feels so nice wearing these clothes’
‘You are looking good Christine, are you hungry’?
‘Yes but I will have to change back first, no way am I going out like this’
‘Oh yes you are, you are very passable as a girl, we will go to where you took me, it has subdued lighting and nobody knows us anyway’
‘But you have done it before’
‘Until yesterday I had never been out except to go to the corner shop and that was late at night’
‘Really? You look so natural and confident’
‘Come girlfriend, my treat tonight’
Christine looked worried as I drove, I parked up and held her hand as we walked into the restaurant.
‘Good evening ladies, table for two’?
‘Yes please’ I answered ‘to one side if possible’
‘Certainly madam, this way please’
There were a few customers seated, two or three looked up at us but then carried on eating, one man took a second glance at us.
‘Horny bastard’ I thought
Once seated, Christine relaxed a little.
‘There, piece of cake, wasn’t it’?
‘Do you think anyone knows’?
‘Of course not, even the man over there was leering after you’
Christine giggled. The waiter came and took our orders, Christine unobtrusively glanced around,
‘Oh my, he smiled at me’ she said nervously
‘There, I told you how good you looked, now you have an admirer, don’t worry, he only wants to fuck you’
‘Ugh. That’s gross’
‘I bet he has a big dick’
‘Do you think so’? Christine enquired
‘Would you like to try it’?
‘No certainly not’
‘Even if he paid you’?
‘No, it would make me a prostitute, anyway how much would he pay once he found out I was not a real girl’?
‘I could tell him anal only and he would have to use a condom, maybe you could get eighty to one hundred pounds, just to get his nuts off’
‘Wow, all that just to fuck little old me’
‘Want to try it’?
‘No Alice, I only want you tonight’
‘I could chat him up for you and haggle the price’
‘Why do you want to sell me to a stranger’?
‘You said you enjoyed being fucked, and it would give you confidence as a girl, to know that you are attractive enough for someone to want you’
‘Where would we do it? Certainly not back at the motel as he could find out who I am’
‘Behind my car in the car park, it’s facing into a dark corner, you could bend over the bonnet’
‘My god, you really want me to go through with it, don’t you’?
‘It would only be for about ten minutes’
‘A hundred pounds for ten minutes’
‘Just turn and smile at him, to see if he is interested’
Christine turned her head and gave him a sexy smile, the man smiled back and made his way over to our table.
‘Good evening ladies, may I introduce myself, my name is John, could I have the pleasure to buy you a drink at the bar’?
He was talking to Christine as he asked, I could see by his gaze that he fancied her.
‘Thank you, that would be nice, this is Christine and my name is Alice, we will freshen up and meet you there’ I answered
‘I will get the drinks in, what would you girls like’?
‘Two dry white wine please’ Christine quickly chirped in
John headed to the bar, I paid the bill, then led Christine to the ladies.
‘Alice, I am so nervous, I am not sure I can go through with it’
‘You will be fine, all you have to do is bend over and think of England while he has his wicked way with your bottom’ I said grinning ‘drop your panties and let me prepare you’
She pulled her panties down, I removed the tape from my dick and taped hers up tight, then using the skin moisturiser from the ladies vanity shelf, I lubricated her anus and managed to eventually get three fingers into her, stretching her rosebud open. I tucked my dick back and pulled my panties up tight.
‘Let’s go girl, John is waiting’
I led a very nervous Christine to the bar, John was seated on a sofa by a small table with the drinks on.
‘Hi girls, have a seat’
‘Can I have a quiet word John’? I asked
John stood up and led me to an empty alcove.
‘Christine is just about to go on the game, she has never sold herself before, I have offered to help her out with her first few clients, it would cost you a hundred pounds cash up front if you want to be her first, but you can only have her anally and you must wear a condom’
‘Supposing she isn’t very good, it seems a lot of money’
‘Ok, if you give me eighty pounds, you can have her, but if you enjoy her, you can give me another twenty. How does that sound’?
‘Seems fair’
He peeled off four twenties and handed them to me, we returned to the sofa, Christine glanced at me nervously. John put his arm around her and whispered something in her ear, she went bright red and nodded to him. John stood up and held his hand out to her, she grasped his hand as he led her outside, she gave me a very worried look as she left with him. I checked my watch, just twenty to the hour, I thought I would give them to the hour before I would get concerned. I sipped my drink, feeling bad about putting her in this position, I began sipping her drink, constantly looking at my watch. As the minute hand reached the hour, I was feeling panicky, just a few more minutes I thought. At ten past, I stood up ready to go and look for her, when they strolled in arm in arm, Christine’s face was bright red and she was walking unsteadily. John helped her onto the sofa, noticed our glasses were empty.
‘I will get fresh drinks’ he said as he left for the bar.
‘Well’? I said
‘God, he is so big, and at least eight inches, I thought he was going to split me in two, and he kept going for such a long time before he cum’
‘How do you feel’?
‘Wonderful, but a bit sore, I feel so girly, he kept telling me what a great fuck I was. Oh Alice, I loved it. He is ever so nice, he treated me like a lady, and he fucks like a stallion, he pleaded with me not to be a whore and asked me to live with him.. oh, here he comes.. tell you later’
John returned with the drinks,
‘Here you are girls’ as he put the drinks down
He pulled out his wad of notes and handed me another four twenties, winked at me and said quietly
‘Best fuck for years’ grinning broadly ‘oh, and by the way, I know she is a he’
‘How’?
‘Christine got a stiff dick while I fucked her, even the tape couldn’t hide that’
he turned to Christine,
‘I really want to see you again, I would like you to be my regular girlfriend’ he lifted her hand and kissed it.
‘I think I would like that too John’ she whispered as she kissed his cheek
‘Before I get in the way of you two lovebirds, I owe you some money Christine’
‘Keep it Alice, if it hadn’t been for you, I would never have met her’
‘But she earned it’ I said
‘Treat yourself to something nice’ Christine said ‘I have got what I want right here’ she said kissing his cheek again ‘I will see you before you leave, say around nine at breakfast’
‘I will make sure she is there’ John said earnestly
I made my farewells and returned to the motel, thinking about Christine and John.
Next morning, I decided to stay as Alice to drive home. I packed my boy clothes and wore my summer dress to go to breakfast, I was feeling so alive and happy as a girl. At ten to nine whilst eating my breakfast, Christine arrived and I could see by the rings under her eyes and the careful way she walked, that she had been busy last night’
‘God, Alice, I am in love with him, I can hardly walk and my bum is so sore, he kept making love to me half the night. You were so right when you said I looked good as a girl. I have come to collect my things, I am going to move in with him, he is waiting outside to take me shopping for clothes and I am booked in for a makeover. Thank you so much for everything. Here take my card, it has my mobile number and email address, please contact me over the weekend’
I gave her my card, the one with Alice Smith on it.
‘I am so pleased for you Christine, I do hope you will be happy, take care sweetie’ I kissed her cheek.
Continued in Alice part two.















































Story URL: http://xhamster.com/user/ratty9uk/posts/28239.html