My Mum and Dad had a Hotel on the South Coast of England, but from a baby I wore my s****rs old clothes, (My s****r was four years older than me), I wore her, shoes, ankle socks, panties, blouses and dress’s until the age of 5, it was only because, I started school, I stopped wearing her things, I became sexually aware, at the age of 12, I was fascinated at all the messages, I found on the Mens toilets, the drawings of Massive Ejaculating cocks with messages on the walls and holes you could see through into the next cubicle, I would go and hang around these toilets, excited as hell waiting to see if anything would happen, but it never did, I had always known that I was trans-gender,. at the age of 14 I started to Cross-dress by borrowing my older s****rs undies and stockings again, my s****r found out, but the surprising thing is, she let me, carry on, she even encouraged me, to do it, playing for hours in our bedrooms, dressed as girls, I accepted that my femme side would never go away, I loved dressing up and the things we used to get up, to, late at night, makes me giggle now, thinking about it, ha, ha, ha, I became fascinated at all the messages, I found on the walls in Mens toilets, the drawings of Massive Ejaculating cocks with messages on the walls with times and dates, the holes you could see through into the next cubicle, I started to hang around these toilets, excited as hell , waiting to see if anything would happen, but it never did, I helped out in the hotel when I wasn't at school, so I would never be able to go there at night, when I knew these meetings happened, I became so frustrated because I wanted to know what went on
At the age of 15 I had grown taller, I was just over 5'4", I had a slim body with long shoulder length hair, I was still, trying on my s****r things, but her underwear was getting very, very Sexy, by now, and I knew she was, having sex, So I had the choice of Wigs, 6" High Heels, Basque's, stockings and suspenders, Makeup, Nails, Dress’s ete; ete; the lot, so I tried it all on I now looked very, very, girly dressed in her clothes and couldn't stop getting an erection, I would wank myself of silly looking at myself in the bedroom mirror, it was worse if I went out all dressed up walking the streets Cars pulled up asking where I was going and did I want a lift anywhere In fact, I was very girly dressed as a boy with my long hair, When I was out, I usually wore my tight hipster jeans, and a nice tight fitting Teashirt which showed of my thin waist line, I knew this worked in attracting the right sort of man because they would follow me through the streets, I would go down to the beach and they would watch me, as I got changed to go for a dip, they would sit not too far away from me, looking or should I say leering at me, sometimes I had a crowd 3-4-5 or more dotted around the beach, watching me, I would lay down on my front, stick my bum high into the air and peel off my ordinary swimming trunks to reveal that I had on a very skimpy G-String on underneath, I just loved to watch, as they got themselves nice and hard, but I wasn't brave enough to go over to them in broad daylight, but of coarse, I wondered, what it might be like, to let one of these men have there way with me and what it would be like, holding there Cock in my hand, or Sucking them off, in Public it was very, very tempting, but it had, always been so for me
But the next Summer Season, things started to change, before the new season started, we had employed some new Catering staff and this is the story of my first sexual experience, with a man, a 60 year old called John, who worked as a goffer and pot washer in our hotel kitchen, I was in my mid-teens by then and still frustrated as hell, at not being able to enjoy a sexual relationship with a man, We called him old John, he was my height but a bit thin and scrawny and I was sure that I had seen him on the beach the year before watching me do my teasing, My Dad had given him a job, because he had been, going around all the hotels on the seafront asking if there was any work, I think he was homeless, because he asked to have a live in position and my dad had given him a room in the basement, behind the Snooker and Games rooms, He was a bit smelly and very dirty to look at and I wondered why my dad had given hin a job, anyway my dad pulled me into the office and told me that he wanted me to look after old John as he was taking, Mum and s****r to do some last minute shopping before we open for the Summer season and then they were going to see my Auntie and Uncle, in Eastbourne, So they might be late coming home, So he wanted me, to look after John, my dad said, "I was to get him something to eat and show John, where his bedroom was and the staff bathroom was and give him some off my clothes to wear for the time being and burn the ones he's got on", I complained saying "but dad I was going out" he didn’t listen to me, he just carried on with what he was saying, "and get John some soap and towels for him as well, He Turned to John and said, “I'll see you tomorrow John, 6 o’clock in the morning OK" speaking to me he said,"Vic, you can go out, after John has had his bath, something to eat and settled in, so off you go, the quicker you do it the faster you can go out and make sure you lock everything up before you go Vic, I quickly grabbed his bags and took him downstairs, showed him where his bedroom was and the bathroom, I left him there running the bath water, while I raced off to get him some of my clothes, I quickly gathered some of my things and went back to him, I knocked on his bedroom door and he shouted out, "I'm in here young chum, I'm in the bath, leave them on the bed for me will you" I thought it would be a good idea to take them to him so he would finish quicker, so I knocked on the bathroom door and asked if it was alright to come in, "Yeaaa ok come in, chum," I went in "Here you are," I said, with my head turned away, "here's some of my things for you to wear, I hope they fit you OK alright, I’ll just go and fix you some super" as I turned around to go out, I caught sight of him, he was standing up in the bath, washing his bum and crutch with soapy water, I didn’t notice how black the water had got because, I was transfixed, I just stood there, I couldn’t help it I just stared at him, while he washed his cock, in front of me, it was wriggling and flopping about, as he ran his hand over its length, the purple head of his cock, made it look like a snake, he just carried on washing it, with out a care in the world, then he said, "could you do me chum" I was still looking at his, half erect cock sticking out in front of him, like a fishing rod under strain,
I just muttered out loud"WWWWWHAT, WWWWWHAT" this was the first time, I had seen a mans cock up close, It was something that I had been having wet dreams about, for ages, I was getting hard, myself and my Erection was pushing out my the front of my Football shorts "Can you do my back for me chum," I mumbled, "I don't know, if I should, I don't know," he could see that the sight of his cock had got me in all of a fluster and I was shaking, with either fear or excitement, He said, "Oh go on, it will be our little secret, chum, I won't bit you, I can't do it myself, now can I, can I" after a few moments, thinking about it, I mumbled again, "Mmmmmmmmm, No I suppose not, ok pass me the cloth, and turn around and I’ll do your back, your food is in your bedroom with a mug of tea, I’ll just wash your back and then I must go and get changed and meet my friends," He answered "ok and handed me the cloth, I washed his back, as quickly as I could but he kept turning around so his half erect Cock kept coming around to face me and I kept on brushing it with my arms as it swung around, I bent down to rinse the cloth out, he turned around again and his cock hit me, "SLAP" across the face, I was so shocked that I didn't know what to do,
I just ran out and up to my room sat on my bed, and thought about what had just happened, I started to giggle and then broke out grinning I didn’t get changed or go out that night but stayed in and thought about what had happened and fiddled with myself all night, I didn’t get much sl**p I just kept thinking about his Cock, How Big, How Long, How Thick, Did he like me, Did he want me, But it didn’t go any further between us for the whole of that summer, but he did follow he down to the beach sometimes and once or twice he would accidently find me laying on the beach sun bathing in my skimpy trunks on and sit with me we got on very well together and became friends, but not intimate friends if you know what I mean.
In late September we were both working in the dinning room when my parents were out, we were just moving the dinning tables and chairs around so we could clean the carpet, we were both sweating a lot so I took of my shirt and tracksuit bottoms so I was just in a T-shirt and boxer shorts, as I did this, I said to John, “that’s enough for today John, make us a mug of tea would you and have one yourself, he brought me the tea and I asked him to sit with me and turnoff the main lights and relax he asked me if I had a girl friend waiting for me, I said something like a chance would be a fine thing, I’m always working here aren’t, I one thing led to another and we got onto the subject of sex and he asked me if I had, sex with a girl and I said, “No, Why” and he said, “well if you want to find out I could show you chum”, I said, “how’s that”, “Well” he said, “I’ve got false teeth and if I took them out and sucked your cock it would feel the same as putting it in a woman’s pussy do you want to try it Vic” He kept on about it, while I thought about it, “go on you’ll like it I bet you will, go on try it, come try it,” in the end,
I said, “Ok show me,” so he got down on his knees, in front of me and pulled the front of my shorts down and put my limp cock in his mouth and started to suck on it, I was shaking with excitement, it didn’t take long to get hard as a rock and john’s head was going at it like a hammer drill and sucking at my cock like a hoover only stopping to ask if I was liking it, “mmmmmm yes I said its lovely John” I laid back in my chair, opened my legs wide and really started to enjoy what he was doing to and my Cock “mmmmmmm yesss John ,that’s nice, mmmmmmmmmmm oh thank you John, thank you that is so nice, he asked me “if I was cuming yet” I said ,“no not yet john” then after about 10 minutes, I started to feel I was cuming I Shouted out, I’m Cuming, I’m Cumming, oooooooooooh John, John, as I felt my Cock reaching a Climax John’s reaction was to suck harder and harder on my swollen Cock which made me wriggle in my chair with pain and ecstasy I was now lifting my hips and fucking his Face as he sucked me off I’m Cuming I’m Cuming oooooh Yesssssss John, John That’s it harder, harder, suck it, Harder, John Suck me, Oooooooooooh Yeaaaaaaaaaa Fuck Fuck Fuck now, now, I’m Cuming yesssss aaaaaaaah ayeeeeeessssssssssss, I came like a Express train, not a drop of my cum escaped his mouth and he said that was the best cum shot he had ever sucked on and I should let him do to me every night, because it would make my cock grow bigger,
I said ,“I enjoyed it so much John, that I would let you suck me off twice a day or night if you wanted too”, He asked me if I wanted to do the same for him I said, “ I don’t know”, “Oh go on Chum” he said, “you don’t have to put it in your mouth if you don’t want to, Shall I get it out, for you and you can decide for yourself what happens, Chum, Go on lets swop places shall we, I wasn’t to sure about it and it took awhile to think it over, I could see how excite he was at the though of me playing with his Cock had gotten him, he was already hard by the bulge in his britches, I’ve wanted to play with a mans Cock for ages, to see what happens and now this old man was offering it to me on a plate the more I thought about it the more I wanted too, Finally I said “alright I’ll do it, But I‘ll stop if I want OK” “ yes my little chum” He said as he took my place in the chair, I got down in front of him and said, “what do I do now John” Well He said, Don’t be frightened, I know you haven’t done this before, take your time, just rub it gently, with that he place one of my hands on the very noticeable, ridge running down the inside of his trousers, I felt the warmth of his Cock through the material as I clumsily pressed my hand down and along it length, but soon eased the pressure, when he told me too, he said, “Gently chum this is supposed to be a tender moment, be gentle, use your fingers to explore what your doing, it will get better results in the end mmmmmmmmmmmmm that’s better chum, oooooooooooooooooo yes that’s much, much better”
I could feel and see what he meant when he said soft and gentle was better as his Cock started to grow in length and thickness, I said, “oh John its getting bigger, much bigger and wider, too”, “Mmmmmmmmm” he went, “that’s good Vic, your doing fine and when your ready, unzip me and pull it out, are you enjoying it so far Vic” “mmmmmmm, yea”, I said, as I started to bite on it gently going from the head to the hilt and rubbing my lips a long it too “How big is it John, you know, how big is it when, when its”, he cut me off by saying “oh about 9 ½ “and 2 ½ “wide but that’s only if I’m really excited”, I replied, “are you getting excited John, I know I’m excited” as I lent forward to undone his top button, “I certainly am chum, your doing fine and you are quite a naughty boy really, aren’t very naughty indeed”, and he lent his head forward and kissed me on the head and laid back again, placing his hands behind his head, “God” I thought “no one has ever kissed me like that except my parents” it sent a shiver of exhilaration running though my torso and gave me the courage to unzip his trousers, put my hand in, I was surprised that he hadn’t got any under pants on and no hair on his balls, or around his groin, none at all, I started to run my fingers tips, over the length of his Cock, I could feel his body tense, as I teased it. clawing at it, with my finger nails which made him look down at what I was doing “ooooooooooo that’s nice chum, that’s really nice, it made him look down at what I was doing Now are you brave or naughty enough, to pull it out into the open Vic, I think you are, am I right chum”,
I looked at him with a cheeky grin on my face, then looked back to what I was doing, while I was thinking about it, he lent forward again and whispered in my ear, sending shivers down my neck and back, saying “Go on Vic I dare you, to pull it out for me and lick it, are you naughty enough to do it, well are you, you naughty boy mmmm”, I looked into his eyes with that cheeky grin off mine, nodded a “Yes”, as I started to tug at his Cock and pulled it out, It was the first real mans Cock I had ever had in my hand I could hardly get my fingers around it, to me it was so monstrous and shocking, I squealed “Jesus, John its so big and fat, I couldn’t get all of that in my mouth” to which he said “Well don’t Vic, but you could Lick it couldn’t you I know you want to go on Lick and see what it tastes like” So I moved my head down into his lap stuck my tongue out and licked his balls and climbing slowly dragging my tongue up the shaft, it seemed a long way up but finally I hit the purple knob, “ooooooooooooooooooooo, You clever little slut, what you going to do now”, he remarked as I was wiggling my tongue over the bl**d engorged head of his member, I opened my mouth and gently slid my teeth over it teasingly nibbling away, then Sucking it into my mouth so I had the head in and started to Wank his Cock with both hands His head fell back as he let me carry on what I was doing moaning to himself “mmmmmmmmmmmmm do that again Vic ooooooooooo Yeaaaaaaaaaa yesssss that’s it just like that, Mmmmmmmmm oooooooooooooooo god, you do that so well”,
I carried on doing it for awhile and then I made a grab for his balls, kneading them with my fingers, while I was Sucking on and teasing his Cock with my teeth, as I pushed my mouth down on his impressive member I pushed a finger behind his Ball sack and pressed quite hard, moving it in a circle, which I know helps me to ejaculate quicker, By this stage I was getting braver and enjoying it tremendously and felt the power I now had over his man, a nibble here and a little squeeze there was making him contort his body as he laid there, with his hands behind his head sending him to heaven, I tell you it made me feel so powerful, as he laid there moaning at what I was doing to his Cock he would say things like, “I thought you had never done this before Vic”, you are so Slutty, Vic I can’t believe you have never done this before, your so good, at it” I said “No I haven’t John, you’re the first real man I’ve ever had, honest ,really I haven’t done anything like this before” “Well, I think I’m going to Cum in a minute Vic, That’s how good at you are”, “Suck on it you dirty slut, mmmmmmmmmmmmmmmmmmmmmmmmm oh, oh, oh, I’m cuming, I’m Cuming Now” I felt his Cock start to twitch, He said, “Suck it Vic I’m going to Cum”, I put my mouth over his purple Cock head again, just in time I had only Sucked on his Cock head for about 30 seconds and had the head and a couple of inches in my mouth when Suddenly, he came, his hole body was in convulsion, as he spurted, a stream of hot creamy spunk into my mouth, he came with such f***e I had to hold his Cock with both hands, while I drank his cum and could feel it sliding down my throat spurt after spurt I made the mistake of thinking he had finished and took it out of my mouth only to be greeted with more as two spurts hit me in the face in quick succession and then more spurts shooting Cum in the air and landing on my chest, I put my lips around it once again and f***ed it into my mouth, I was absolutely covered with hot sticky juice as I felt him quieting down and his Cock start to go limp in my mouth, I squeezed it with both hands and tried to push more of him into my mouth greedy for more, thinking that if I did this he would get hard again, His Cock just got floppier and with the that I ended with up with my lips kissing his balls and his Cock, in my mouth all soft and floppy,
I withdrew it and sat up looking at him He said, “How do you feel Vic, did you enjoy yourself, you certainly looked as if you did, young man, Why you got that frown on your face now”, “I thought it would last longer, can we do it again John, Please, Please” I pleaded, he replied, “Not at the moment sweet boy, I needed time to recover you know, You’ve drain the Cum right out of me Vic, I tell you what, get cleaned up and go and lock all the doors to the hotel, I’ll finish in here, then when everyone is in bed, you come downstairs, to my room and we can have another go and this time it will last much longer, but you must come down nice and quietly OK” “ah I see you’ve got that grin on your face again Vic now go and I’ll see you later” Well I did go down to him later and I had a great time in his bed that night and he was right it did last longer I stayed all night and never got to sl**p, my farther was wondering why both John and I were so sl**py.
Our secret relationship grew and grew and lasted for about 1 ½ years none of my f****y knew about it, until he was sacked by my farther, when he found out that John was fucking me in the ass with his 9 ½ “ Cock, every night while I was dressed as a Very Slutty Female. Stretching my Anal passage to the full but that is another story for the future x x x x x x x x x x xx x Love Viki