Crossroads Part 1 (fiction)

I had a lonely couple of years with no job and without much contact with other people and I really was beginning to find life a bit lonely after my divorce and eventual move into a small flat. What I really would have liked is a partner, someone to share things with and most importantly someone to come home to. Having seen an advert for help wanted in a charity shop in my town I thought I might try that as a way of meeting people. I was taken on and over a short period of time I was rapidly promoted to the paid job of manager with a few older ladies as volunteer staff. We all got on well and I know that at least one of these ladies had her eye on me but none of them interested me. Of course I would take of advantage of sneaky looks down their top or up their skirt - I am only human - male flesh and bl**d, and it had now been sometime without "s" "e" "x". Night after night I consoled myself with looking at various websites and giving myself manual relief fantasising over the whole gamut of the sexual world. Time after time I would come back to looking at photos and video of lesbians. In my fantasy world I would conjure up thoughts of being female and joining in with their lovemaking. I looked at crossdressers and transvestites in a similar way too. Seeing them in each others arms, their legs entwined and even though I knew they were men the image of them lingered on into my dreams at night.
Returning to the charity shop I'd find on most mornings a few black bin liners and a couple of cardboard boxes contain donations dropped off during the night on our doorstep. I made it my first job of the day to carry these through to the back room where they would be sorted and priced. This cold and frosty morning was no exception; there were the customary bags and boxes to greet me. Having nearly taken them all through I was greeted by Cath who had come in to help out a bit earlier than usual, she brought in the last remaining bag with her, the door was shut and the heating switched on. Cath also divorced is a largish lady in her 60's and not very worldly wise. She needed this work to get her out of her house and to meet people much the same as myself. We got along just fine especially as she now produced a hot mug of coffee for me. It was just going to be me and her as today was half day closing there was no need for anyone else. The place soon warmed up and at 9 am prompt Cath turned the sign from closed to open and returned back to the counter while I put the float into the till. I had a feeling it was going to be a quiet day if not for Cath chatting away! I swear that she had gills behind her ears as she never seemed to come up for breath as she chatted away eventually I needed to get away from her for a while so I went into the back room and as I did I heard the front door open and close and Cath greeted the customer and started chatting to them. I stayed out of the way - just to give my ear holes a rest! I put the kettle on to return the favour of the earlier coffee. I heard Cath at the till and moments late the door opened and closed and Cath appeared.
"You know that beautiful fake fur jacket that’s been here for ages and ages" I must have looked bemused as she continued" It's been on the size 8 rail ever since I have been coming here". It dawned on me now which jacket she spoke of, "well it ain’t there now! A lovely little lady has just bought it for herself" she beamed as if making a "prize" sale. I was certain she'd let the rest of the volunteers know of her sale as soon as possible.
Well it was coming up for 11 o'clock and just as I thought it had been a slow morning and Cath was getting to be more than I could endure with nobody else to talk to I had taken the full brunt of her conversational skills. I would drift off into my little fantasy world of lesbianism and crossdressing while she droned on about this and that with me thankfully nodding and agreeing in all of the right places. She got up and asked if I was happy with the front window display. I must admit it was looking tired and needed something doing to it to liven it up a bit. Cath was wearing what could be a secretarial outfit and I had noticed the tell tale bumps of suspender clips while we had sat side by side drinking our coffee behind the counter. I did wonder to myself if she was a regular stocking wearer or was this for my benefit. I put those thoughts to one side and went back to my fantasy world while I watched Cath bending over reaching goods in the front window. I didn't realise at first but I was becoming increasingly turned on watching her rounded buttocks in her tight grey skirt. I began to feel slightly uneasy about ogling her bottom but then thoughts began to turn to her clothing; I started to look at what she was wearing rather than her. The smart grey skirt had a nice inverted "V" shaped split that ended higher than was probably thought decent for her age and following the line of that it lead me to the zipper, then my eyes moved back down to sheer black nylons and black court shoes with a sensible heel. Her efforts had caused her white blouse to become untidy and she stood side on to me and tucked it back under the skirt waistband. Her breasts were largish and held in place by a white bra barely visible through the blouse. What was I thinking - what must she be thinking seeing me looking at her like this. She must have thought I was admiring her while all the time I was thinking there must be a wealth of clothes in the rear store room waiting for me to try on! I must have chuckled out loud when a particular thought crossed my mind as Cath stopped talking and asked what the matter was "nothing Cath, I was just thinking about what I might do later" I replied. In fact what I had been thinking of was a feminine name for myself and had thought of "Charity"! I clock watched for the rest of the morning and was glad when 1 o'clock arrived as this meant I would then have the shop to myself. I had already started to peruse the rails mentally picking out stock. "This place is a goldmine for a crossdresser - a veritable one stop shop" I thought to myself. It has everything I want even a selection of wigs, shoes, handbags, jewellery - everything!!
Cath was lingering and I desperately wanted her to go but did not want to arouse any suspicions by trying to get her to leave. I'm not sure of her intentions but I felt that she would have liked to stay until I locked up. I came up with "Thanks Cath, for tidying the window looks a lot better now, would you turn the front lights out and turn the sign over on your way out". I could almost see her deflate after I said that and it was obvious to me then that she wanted to remain until I left, but I had other plans - which did not include her. After she left I almost lunged at the front door to lock it and grabbed a few items that I had earmarked as I went back through. I was feeling fortunate that in this town clothing to suit all ages was donated to this shop. I was going to have a field day! The previous occupier of these premises was a women’s clothing store and a couple of changing areas had been kept, fortunately so had the full length mirrors on the three walls inside the curtained booths. My nerves were shot to pieces as I entered the back room, my hands trembled as touched this clothing with a whole new sense of meaning. I had picked out and brought back a couple of skirts, one grey and similar to what Cath had been wearing and a kilt, both size 18. Other items included a green and a red roll neck jumper, modern looking beige handbag and a pair of ankle boots in a similar colour. Another foray into the front half of the shop saw me return with suitable underwear and some brand new barely black tights. This time I closed the door to the back of the shop behind me and put my coat on the floor to stop light from being seen by any passer by. I knew what I had to do now and that was to strip off right here and get changed - no niceties - just change in to female attire. It was not as easy as that, the stripping was easy enough but with each item of clothing that went on the changes went deeper than just putting on the opposite sexes clothing - it became a state of mind. The black bra needed something to fill out the cups but the black silky knickers felt delicious. With trembling hands I took out the tights and rolled them up each leg one bit at a time, above the sound of my heart pumping faster came the sound of the stretching newness of the nylon. To me my nylon encased legs seemed to take on another shape as I ran my hands around feeling my sex and caressing my buttocks now held so tight. Next I put on the kilt and the red roll necked jumper. I felt so sexy, I caressed my breasts and run my hands around my body and up and down my legs, yes I had an erection even though for some reason I felt guilty, guilty for feeling enjoyment. Placing a hand against a wall I stepped into a boot and pulled it fully on, swapping hands I did the same with the other boot. Suddenly taller and feeling wobbly on the 2" narrow heels I looked down at them "Mmmm not a bad choice" I thought. I stepped away from my male clothing tottering slightly, my ankles definitely did not belong to me! This was more difficult than I could have believed. I would have to take this little collection home with me and practice though I knew I could stay here a lot longer I felt I needed the security of being in my own home. I felt like a burglar as I found a hold all and as I stripped off filled it with my new found "other self". Before I left for the day I found a blonde wig that I thought might suit me, some clip on earrings, a necklace or two, odd bracelets, a watch and a couple more packs of tights just in case I laddered a pair and of course a suitable coat. "There", I thought "all a girl needs! For now anyway!" I had a deep gut feeling that I had stumbled upon something not just exciting but something deeper, something that perhaps had been lurking there just waiting. "Perhaps I should call myself Pandora" I said to the empty shop, for Pandora's Box had now been opened.
Setting the alarm I hurried to the front door with hold all and keys at the ready. As the alarm rapidly beeped for the final few seconds before arming I took a quick look around to see if I missed something. I felt I had. I opened and closed the door raised the key to the hole and was greeted by "Hello" I turned and saw the fake fur jacket that had adorned our clothing rail for so long being worn by a petite lady......... I looked again........ Was she? Was she a he? I could not tell or be certain so tact played the better of me and I preferred to think of her as all female. "Hello" I replied "I think I missed you earlier when you came in earlier" I said finally rotating the keys as the alarm inside went into its final frenzy before setting itself. "Looks like you’ve just raided the shop with that hold all, that and the guilty look" she said. I think she had me weighed up all too quickly, did I look that guilty?! "The hold all of guilty secrets" I replied, "actually I run the shop" I said hoping to head off any more conversation so I could get home. "I don't normally "do" charity shops" my friendly stranger said, "but I found this hard to resist" she said stroking the collar of her latest buy. What I found hard to accept was she was looking at my crotch while she said that. I cleared my throat and said "can I help you in any way miss? As you can see I was just locking up, but if there is anything..........." I trailed off leaving her to fill in the blanks. " No, no, I'm okay, just looking around this little town, getting to know my way around. Actually, perhaps you could help, could you point me in the direction of a hotel........... please"
"Well we have plenty to choose from normally but this is the winter season, I'm not sure whether you'll be in luck" I said mentally kicking myself for now realising that I'd have no makeup to wear when I got dressed (crossdressed?), "I normally have a coffee before I head back to my horrible little flat and it's on the way to where most of the hotels are....... errr....... miss, can I treat you?"
"Call me Rachel, and yes thank you ........ Mr." she looked up at me with a cheeky smile.
"Michael, Mike, Mick, I'll answer to most names!" I replied as her right arm threaded itself between me and over my left arm. We must have looked like a man and wife walking along. Not that I minded at all, it felt nice, natural, actually I felt damned pleased with myself!! I hoped that the whole world could see me with an attractive lady on my arm...... probably the male ego had kicked in replacing the crossdressed turmoil of earlier. On reaching the cafe I liked to use we found an empty table, it was quite full for a Wednesday afternoon so I could only assume that shoppers had come in here for a warm before leaving for home. We chatted pleasantly over a hot drink and my doubts over her sexuality were confirmed....... I think. If I was talking to a male then I was talking to a pretty convincing feminine male. Thoughts of earlier fantasies returned. If I felt I was in turmoil before then at this moment I was in a state of near panic. Not only had I forgotten how to talk to a lady but I had no idea how to talk to this person - Rachel........
"Errr Rachel........."I started lamely, "what brings you to this town on a cold winter’s day?"
"I want to visit a certain little place and really don't want the drive to and from it today, so I thought I'd come and have a look around and stay the night", she explained.
"Is it friends you’re visiting?" I asked
"Not quite" came the quick reply, she smiled briefly at some inner thought. This person who sat before me was a "she", I couldn't think of her any other way.
"You chose the wrong day to come and have a look around this town. I'm not saying this place is quiet but I think the town is waiting for us to go so they can turn out the lights and put the cat out!", I quipped making her perfect smile appear again.
"What would a visitor do then", she tested me on that one as I had to think hard. What would a visitor to the town do on a day like today apart from turn around and head straight back out!
"I really wouldn't know, err.... Rachel", and I truly didn't know, "if you hadn't have stopped me I would’ve just gone back to my flat and waited for tomorrow"
"So you wouldn't have emptied out your bag and sorted it out then?" she probed. I felt my face redden.
Thoughts ran around my mind, "Had she seen me grabbing the clothes? Was she just testing me? Had she seen something in me that I hadn't? How does this shemale / crossdressing thing work anyway?"
Her hand reached out and touched mine, "its okay, I saw you through the window" she said in a tender, caring way as if she knew what was going on inside of me. Tears welled up in my eyes. What were they for? Relief? The fact that I'd been caught?.......... What? Rachel continued, "Not only did I see you collecting clothes off of a rail your size after the shop was closed, but you sort of made it obvious on a crossdressing message board a few nights ago where you worked and I thought I'd come and check you out. I just put two and two together".
"So that was it. This is a fine mess. Now what do I do!" I thought.
"You really have me stumped Rachel" my voice sounding more than a little shaky. In truth I felt like running out of the cafe, leaving behind the mess I had made - the cowards way out. But I liked Rachel, and I have always considered myself a gentleman and would not have left her to pay for our drinks. The biggest test of my extremely short crossdressing life came sooner than I thought as Rachel turned her head this way and that then said "I won't be a 'mo, just going to tidy myself up a bit" up she got handbag and all and headed off to the ladies toilet. I sat there dumbfounded which was not hard for me to do considering how my day was turning out! As Rachel returned I realised that I had my feet pressed to the floor ready to leap up and run. "There" she said "ready?" The "ready" part was as much a question as telling me she wanted to leave. I looked up to see she'd applied some more lipstick and somehow looked prettier.......... a woman's touch I supposed. I paid the bill and she linked her arm in mine again, all perfectly natural for her. I hadn't a clue what to do or where to go. Standing outside I knew that I wanted to head for somewhere warm and get to know my new found friend a bit more. I turned to continue my normal route home mainly out of habit and partly because we still had to find a hotel for Rachel.
We stopped outside a dress shop. I looked at Rachel's reflection. Our eyes met. Embarrassed I turned away and said "Is your car nearby?" We continued on for a shop or two more. "Not far" was all she said admiring the mannequins clothes. Getting to the end of the shops we reached a crossroads.......... I reached a different sort of crossroads. I could have directed Rachel to a nearby hotel to the left. On the right was the road to my flat and straight on was the seafront. The chill wind picked up as we stood there then a light rain which was threatening to become more started. "Which way Mike?" once again she had read my mind.
"I think the seafront is out in this weather" my words whipped away as a gust of wind flung the rain harder into our faces. If we didn't move soon we would have been soaked. "Come with me. Quick". Hand in hand we crossed to the right hand road. What was light rain mere seconds ago was now horrible, cold, driving sleet.
We arrived at the door to my flat soaked through and cold. I fished in a cold wet pocket for my door keys with a cold wet hand. All I could think of was getting out of these clothes and getting warm. Warm, warm warm! At last we entered and thankfully I had set the heating to come on for midday so now at nearly 3 o'clock it felt pleasant. Although I called "home" a flat it was more like a large bed-sit so the first thing to greet us was the unmade bed. Looking at my visitor I helped her off with her coat, "Rachel I know it's not much but please make yourself at home. Turn the fire on and I'll get us some warm towels straight out of the airing cupboard" The cupboard was in the bathroom as I shut the door behind me I stripped off and took my dressing gown from the hook on the door. What a relief to get those cold wet clothes off. I started to feel warmer immediately. I chose a big fluffy towel for Rachel and returned with an equally fluffy dressing gown to see that she'd turned the gas fire on and was absorbing as much heat as a person could. "Did you bring any more clothes with you Rachel if not I can dry off what you have".
Rachel looked up at me surprised to see that I had undressed so quickly, "I've got a few bits and pieces with me, not a lot really, just a few night time clothes, bit of an overnight bag really".
"Rachel I sorry, I didn't want to embarrass you. But I suggest you do the same", indicating my dressing gown and the one I brought for her. This lovely person who a short while ago now looked as helpless as any lady would caught in the same situation. "I can get dried off a bit more and after I get changed and warmed up I could find your car and bring it here that way at least you'd have your bag". Rachel who by now was starting to feel more relaxed sitting crosslegged in front of the fire turned reached out and stroked the back of my leg in a very feminine gesture, "Thanks Mike" she almost purred. I stood there heart in mouth. I had just been touched by somebody of the same sex as me - alarm bells rang in my mind. Was it not a nice feeling to be appreciated? But SHE TOUCHED ME! I had to get a hold on these strange emotions. Rachel was undressing down to her bra as she sat there and I automatically d****d the dressing gown around her shoulders which she then pulled tighter together reveling in its warmth. I walked around the room gathering from various drawers what I was going to wear and took these back into the bathroom where I dressed. I felt much warmer but still at some unease with the situation - why?
I returned to Rachel and asked her how long before she had to meet her friends thinking that she might like something to eat before she left. "Oh, I haven't got to be there 'till seven, or even later" she said raising her arms and stretching her body, "And really Mike I still have to find a place for tonight" turning to me and looking directly at me continued, "To be honest I don't feel like doing anything but staying in front of this fire!"
"Could I tempt you away from there with the offer of a nice hot bath?" I said smiling
"You might......." her words hung in the air. They meant more than just words.
"Well it would be silly to leave and find a room elsewhere" Me, ever the practical one. "Now where did you park your car and what do I look for?" I was forming a small plan.
As I left the flat Rachel said that she was going to take advantage of the offer of a bath. I promised her that she would have at least half an hour to herself before I returned. "Well" I thought to myself as I headed along the wet pavements, "At least the rain has stopped". I looked at the shop that we had stopped at earlier and continued along past the darkened shops and the cafe and found myself at "my" shop. I entered turned on a couple of lights and turned off the alarm. I had been right....... there on the size 8 rail was something very similar to what Rachel had been looking at. I took that and went in search of some undies, I knew we had a good stock of them as a major clothing store had donated a large quantity of "end of line" and there were some "seconds" as well. By the time I locked up again I knew that Rachel was going to be well pleased with my selection and so with a lighter step I went in search of her car. It was just where she said it was and as I shut the car door I breathed in her feminine scent as I settled down to familiarise myself with the controls. Arriving at the rear of my flat I parked the car and looked up at my flat, the bathroom light was still on and silhouetted against the blind I saw her shape. The light soon went off and I gladly left her cooling car to return to the warmth of my flat. Rachel was delighted with the clothing, touching and feeling each item before trying them on. When I had returned she had been sitting crosslegged in front of the fire again. All of her clothes were piled up on the worktop above the tumble drier including, I noticed, her bra and knickers. Turning her back to me now she opened her dressing gown and slid the black silky knickers up her legs, still with her back to me she shrugged the gown off and put on the matching bra. She had no trouble in matching the hook and eye fastening around her back and turned to face me striking a pose before coming over to hug me and planting a kiss on my cheek. She was so happy! "Thank you darling" she breathed into my neck and returned to open a packet of tights. I had to turn away and busy myself doing...... something! I had found putting on tights earlier such a turn on I was afraid for my emotions or reactions if I was to see her put them on. I went over to the kitchen area and busied myself make us both a coffee. I turned to ask Rachel something just as she bent over to fiddle with the shortish dark green pleated skirt. The black tights pulled to a pale opaqueness over Rachel's taught round buttocks was a sight I would never forget. I was transfixed - like a rabbit staring into car headlights! The kettle clicked off and brought me back to this world. What was it I was going to ask Rachel? Never mind! "Rach", I said, "Looks like a label is still attached to your knicks". A small delicate hand appeared, thumb inside the waistband which moved this way and that until the offending label was found. "Do me a favour Mike, please". I got a pair of scissors and advanced towards Rachel's sexy little bottom. I called upon all the god's to give me the strength and willpower not to fondle, kiss, caress, touch, bite, lick or any other thing which would betray how I now felt towards Rachel. A trembling finger located the label. It was held in by one of those horrible plastic threads, if I hadn't noticed it it would have irritated Rachel no end. I snipped and the label came free but where on earth did part of the thread go........ "Rachel, I think we have a problem" and I was not talking about my growing erection either! I was sure the missing part had fallen inside her knickers. As I explained Rachel giggled, she was not at all worried...... it was my fault so I had to find it was her reasoning!! I truly believed at that moment the gods were failing me, they departed one by one laughing at me, taunting my sexuality, my reasoning as I pulled the combined waistbands of her knickers and tights away and looked for the first time at her creamy smooth buttocks. How I would have dearly liked to bend her over and.......... I saw it, that damned little piece of plastic. "Please, let me just get it and let me return to "normal" PLEASE I promise I won't look at any more crossdressing websites" I mentally pleaded with the few remaining gods who'd stuck around to see if I crumbled under this seemingly innocent favour. I wetted a finger and touched it and it came away. I had it. "Nice view?" Rachel teasingly enquired. My throat had tightened to a point where I could only reply with "MMmmm". What I had wanted to say was the truth.......that at that moment I would have worshipped her ass given the chance. I looked at her back the smooth pale skin contrasting with the black underwear. Feeling a kind of bravado I slipped a finger under the back of the bra to see if there was any sign of a label there. No. I left her to return to the kettle and to discreetly rearrange my erection. Coffee made I was beginning to fight with the angels and demons inside me - I wonder if I had missed an opportunity of a lifetime to fondle Rachel - why should I break the trust of an innocent person who asked me to do a favour - there might never be another time - I need a friend and so on the arguments went on. I knew what was right and what was wrong and I also knew that I did the right thing no matter how Rachel teased with her comment about the view. It was all done in such sweet innocence by her who in a way made it easier for me..... in the end. Looking back Rachel continued putting on the clothes which all seemed to be fitting her perfectly, partly a lucky guess on my side, partly because of the work I was doing I supposed. Time was getting on and if Rachel was to meet up with her friends then it was nearly time for her to leave. Off she went to the bathroom carrying her makeup bag. I looked admiringly at her legs, she cast me a glance giving me a knowing smile, and she knew what I was thinking. I must have been read like an open book to her, in a strange way I think she knew me better than I did. "Are you going to be able to find my flat again okay Rachel", I called. The reply came back, "Pardon?" I walked around to the bathroom door to see her sitting on the loo with a small mirror in one hand and brushing something around her eyelids with the other. I was slightly taken aback to see her in this position, but if I'd learnt one thing about her I knew that everything she did she did with an air of innocence. It was me that had the hang ups. "Will you be okay finding this place again after you’ve seen your friends?" I asked again. "I hadn't thought about that" she said waving the small mirror to one side and looking at me, "Tell you what why don't you come with me" It was then that I learned that she was going to meet up with even more crossdressers for a social chit chat and maybe a glass of wine. I didn't know what to say. "Could I just go as I am" I certainly didn't want to be seen by anyone else. "Okay Mike, but you'll wish differently when you get there" was Rachel's reply meant to give me the impetus I needed. I hadn't even opened the bag of clothes that I took from the shop, thankfully the bag was waterproof and I had wrapped most of the items into carrier bags as well. While Rachel put final preparations to her makeup I laid out the contents on the bed. Still full of self doubt I thought I would undress and make a start putting on some of these items while I had some privacy. "MMM" I heard when I had taken off my last piece of male clothing, "That is going to have to be shaved and its going to be a job to hide that in a pair of knicks" Rachel flipped a painted fingernail in the general direction of my "pride and joy". In a motherly tone she continued, "When we get back I want you in the bath and I am going to give you a damned good shave, it's going to take too long to get you ready now", I hadn't heard her speak like this before and I took note, "you'll have to go as "him", but later after I have worked on you for two or three hours I think you'll be okay". Who was I to argue!! We left soon after this and it was decided between us that Rachel would drive us there and I would drive back. We stopped on the way to buy a couple of bottles of wine for when we returned. Under the street lights I watched Rachel’s slender legs work the pedals, I'm not sure if she knew it but the skirt had ridden up high and I could see a flash of thigh. I was certainly attracted to her or perhaps it was the idea of her or maybe it was just male lust!! Leaving the lights of the town behind us we continued on to a country road. Turning to me grinning she said "I think maybe I should have used the bathroom once more before we left".
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Categories: Shemales
Posted by michaella_cd
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