Long hot summer for crossdressing student doing vacation job
It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with a fairly old-fashioned landlady. The freedom of being fairly anonymous in this new job and town was making me feel randy, and my cock was twitching almost continuously. Although I was trying to kick the crossdressing habit, for the first time in months I was daydreaming about doing some very naughty things with panties. Still, it was a bit dangerous when in a strange environment to get dressed up or even just to buy a pair of panties at a nearby shop, what if gossip got around in this small town? Also my landlady didn't look the type to have anything other than functional underwear in her bottom drawer, so I put the idea out of my head.
After the first week at work was over I spent a lazy Saturday just looking round the town and doing some shopping. The next Sunday I decided to go for a walk into the countryside as the town was a bit boring. I walked for a few miles through a wood and then across some fields before coming to a picture-perfect English village. There was a village green complete with duck pond, pretty houses with gardens full of flowers, a couple of village pubs, some small shops and a cricket ground. The sun was hot and I was feeling lazy, so I decided to get a beer from one of the pubs and sit on the edge of the cricket pitch and watch the game.
Being the 1980s very short shorts were the fashion, and I was wearing a pair of old cut down faded tight jeans which barely extended an inch down my thighs, tennis shoes without socks and a pink and white t-shirt with the arms cut off. I had long, thin almost hairless legs. In fact my whole body was thin and almost hairless, only my pubic hair and underarm hair was really noticeable and even that wasn't very much. Add in shoulder length blond hair and even without dressing up in woman's clothing I had a very feminine look to me.
As I luxuriated on the warm grass watching the game I saw a fine looking older man sitting on a bench nearby me. He looked like he was in his late 50s, with receding grey hair and a moustache, and striking blue eyes. He was smoking a cigar and carried a cool air of authority. The reason I had noticed him was that he had been looking directly at me. Although occasionally turning his head to watch a bit of the game, he seemed to be more interested in looking at me, and made no secret of it, staring right into my eyes, and running his gaze over my lithe body, stretched out on the grass. In spite of myself I blushed, and even worse I felt my cock rapidly grow inside my jeans, I was getting a massive erection! I quickly turned over on to my stomach to escape his gaze, and also to hide my erection which I hoped he hadn't noticed, although the way he had raised his eyebrows made that unlikely.
I lay like that face down for a bit, wondering how long he would look at me for, and if when I turned round again he would still be staring at me. After 10 minutes or so of trying to relax and not show him that I was a bit shaken, I felt the warm sun on my back suddenly fade out. I turned round to see him standing behind me, blocking out the sun, his legs spread slightly apart. I couldn't help but notice the large bulge in his trousers. He spoke to me in a deep, confident voice.
"Well hallo there, I haven't seen you around here before. Are you here on a day trip from London, student I would guess?"
"No" I replied, "I'm staying in the town nearby, I just felt like a walk into the country today. But I am a student" I smiled.
The conversation got going, with him asking my name, and what I was doing for a job over the summer, and what I thought of cricket. He was skilled at teasing information out of me, and I started to relax a bit, as he guided the conversation in the direction that he wanted. Finally he asked me if I would like to go for lunch with him, in such a way that it was hard for me to say no.
"Ye-es" I stammered, "Th-thank you"
I stood up and walked with him in the direction that he beckoned, until after a short while on the outskirts of the village we came to a large house surrounded by walls and hedging. He announced that this was where he lived and opened the tall wooden gate, waving me inside. As I walked inside into his courtyard I heard the gate slam shut behind me, blocking out the outside world. I gulped a bit, and wondered what would happen next.
This man must be seriously rich I thought to myself, there was a swimming pool, tennis court, conservatory and sun terrace outside in the massive gardens. Two very expensive looking cars were parked on the gravel, there were probably others in the garage round to the side of the house. He opened his front door and gestured me to go inside.
"Welcome to my humble abode" he laughed. "By the way, my name is Jonathan"
"I'm Sam" I replied. He smiled strangely. "Ah a Sam. Well well".
I was shown to a beautiful enclosed courtyard, with tables and chairs.
"Please sit down" he said, "let's drink a glass of red wine before I get the lunch ready"
"How very pleasant" I though to myself, "I wonder what he's up to?" Was it to just be a meal and a chat, or did he maybe fancy me a bit and want a bit of naughty cock action? The thought of being fancied by this sexy older man made me feel a rather naughty, I started to get aroused again.
Jonathan came back with a bottle of red and 2 glasses, and a picture frame under his arm. He poured out the wine and we clinked glasses and started to drink.
"This is my wife, Elaine" he said proudly, showing me the picture in the photo frame. A tall looking woman in an beautiful evening dress stared out of the picture at me. She looked about 50, very sexy and although slim she had enough curves in the right places.
"She's very beautiful" I said, thinking that maybe there wasn't much chance of anything happening after all.
"She just flew off this morning to Papua New Guinea for 2 months" he smiled wryly.
"Where?" I blurted out.
"Oh, a long way away, the other side of the world in fact"
"That's a shame" I replied.
"It is indeed" he said. "We had one hell of a day yesterday though" he smiled.
"For lunch Elaine got dressed up in her little black dress and her high-heels and stockings and suspenders" he grinned, watching me carefully.
"We had fantastic sex twice in the afternoon. Then it was out for a meal in the evening, but on the way to the restaurant the old girl was so horny I actually had to pull off down a quiet country lane so I could fuck her in the back of the car. Imagine that, she couldn't even wait to get home!" he laughed, "I can understand it, she won't be getting any for the next two months."
This was a little too much information for me. I started to blush. The idea of him fucking his sexy wife senseless was a turn on of course, but why was he telling me this? A bit much to be speaking to someone he hardly knew in this manner. Also I was feeling a bit disappointed, the chances of a bit of cock action were looking non-existent, this man was clearly very very heterosexual.
"Well anyway, she pulled her panties back on and we went on to the restaurant. When we finally got back home we made love on the chaise lounge, then it was up off to bed for a night of passion"
I still couldn't really see what this had to do with me so I just muttered "oh that's nice", thinking to myself that this Jonathan was a strange one.
He smiled and asked if I wanted another glass of wine. After I'd answered "yes please" he leaned over the table to pour. Just as he'd filled my glass to the brim the top of the bottle seemed to catch the rim of the glass and flip it over towards me. Red wine spilled over my t-shirt and onto my shorts and over my legs.
"Oh I'm so sorry" he cried, "how very clumsy of me!"
"Oh don't worry" I said, thinking that I was going to look very stupid walking all the way back to town with a red wine stain covering most of the clothes I had on.
"We must get you cleaned up and get those clothes washed before the stain sets. Quick, come with me."
He grabbed my arm and taking me into the house again led me up some wide stairs to the first floor. He ushered me in through a door into a plush magnificent big bath. Leaning over the bath he fixed the plug in the hole and turned on both antique taps, and steaming water started to gush out. Some bubble bath was squirted into the water, and he turned to me smiling.
"Quick then, out of those clothes and into this bath when it's ready, I'll put you're clothes in the washing machine."
I stepped out of my shoes, and took off my shorts and t-shirt, before hesitating about whether to take off my underpants or not. One reason for this was that I was a bit worried about what he'd do next, the other was that I was pretty sure that there was a wet patch on the underpants where the head of my cock was pressing when I had the erection earlier!
"Don't be shy" he ordered, "come on now then get out of them, it's all got to go in the washing machine. Don't think that I haven't seen it all before!"
I stepped out of my underpants and handed them to him. He took a slow look at them and raised his eyebrows. Damn, he had seen the wet patch! I had no trace of an erection any more, as I climbed into the bath and tried to hide my nakedness under the foaming bubbles.
"Excellent!" he exclaimed, "I'll be back up in a bit when I've sorted this out and attended to another couple of things. Have a good soak!"
I lay back in the hot steamy bath, trying not to worry too much. After a while I started to wash in the warm soapy water. It felt good on my smooth bare skin. When I washed my cock I immediately started to get hard. I played with it absent mindedly for a bit, then stopped with a jolt as Jonathan came back in through the door. He grinned at me, sensing my discomfort. Had he seen me playing with my cock? It was doubtful as there was so much foam in the bath, but that tell-tale pulling away of the hand when you get caught playing with yourself had probably given me away. My erection sunk again.
"Here's a towel" he said, holding out a huge burgundy bath towel. "Get out and get dried off, I've found some clothes for you to wear until yours are dry again."
I dutifully got out of the bath and dried myself off, trying hide my body from his roaming eyes. Once I was dry he led me out into the hallway and along the corridor.
"Here we go then, this is my bedroom, I've laid the clothes put on the bed for you."
He moved aside to let me pass, and I walked through the door into his bedroom. I looked at the bed and suddenly lost my breath., shocked at what I saw. What was lying on the bed was not the pair of jeans and t-shirt that I was expecting, but carefully laid out woman's clothing!
I was speechless as my eyes moved over the various items. The sheer black nylon stockings caught my glance first, and next to them a pair of skimpy black lacy panties. There was a lacy similarly skimpy suspender belt and bra to match the panties. The main item of clothing was what looked like a fairly short strappy black velvet cocktail dress, and to round it all off a pair of black patent slingback high heels.
My God! How did he know I was a crossdresser? Did he really just know, am I really so effeminate? Or was it just a wild guess, does he do this to every boy he meets at the cricket ground? Although I was completely speechless all those thoughts ran through my head. I felt the towel being pulled away firmly from my naked body, and then I got my answer.
"Well Sam, or should I say Samantha? You're not really much of a Samuel are you? I could tell right away that this is your game. You're gagging for this, aren't you?"
"I - I -I don't know what you mean Jonathan" I finally managed to blurt out.
"Come on now. At least your cock isn't telling me any lies Samantha."
I looked down. It was true, I was now sporting a massive erection, and the truth was I felt randy as hell. I really wanted to do it, I wanted to dress up in the clothes. What the hell, this is what I love doing sexually, and I really fancied him too! This could be my first time with a man while I'm dressed! Slowly, almost involuntarily, I moved towards the bed.
"Yes, I knew it!" exclaimed Jonathan triumphantly. "These are the clothes my wife was wearing yesterday. She's nearly as tall as you, I think they'll suit you very well indeed."
I leant down and ran a hand over the sheer stockings. My legs were shaking, and my breathing was heavy. Just as I had in the past when I sneaked into my mothers bedroom when she was out, I picked up the suspender belt first, arranged it round my waist and fastened the clasp in the small of my back. With shaking hands I picked up one stocking, rolled it down and put my foot in, before pulling it back up and smoothing it up to the top of my thigh. I fastened the suspenders onto it. Then the same with the other leg and the other stocking. I looked down at myself and saw my long shapely legs encased in nylon, with my erection reaching up proudly to the suspender belt itself. Jonathan was beaming broadly, a massive bulge in his trousers.
Time for the panties. I held them up close to me, working out which way round they went so that I could step into them. As I go them into the correct shape I could see that the crotch was filthy and still glistening with wetness.
"Yes" said Jonathan, "they're rather dirty. They should be, wife was wearing them all afternoon and evening, well not all the time, they must have come off and on again at least 5 or 6 times when I was licking her and fucking her!"
I couldn't help it, I held them up to my nose. The stench was overpowering, a mixture of cunt juice, sweat, stale sperm and pee. It was fantastic. Jonathan grinned widely as I stepped into them and pulled them up over my stocking tops. By now he had removed his enormous erect cock from his trousers and was slowly stroking it. I pulled the panties up and gasped as the still soaking wet crotch made contact with my the base of my cock. I was now feeling totally wanton, I wanted to get dressed so much and then be on the end of a fantastic seeing-to from this man and his wonderful cock.
I picked up the bra, slid my arms into it, positioned it and then fastened it behind my back. Next I held up the black velvet cocktail dress by the straps. The zip down the back was undone, so I stepped into it, then pulled it up until my arms could slip through the straps. I wriggled around until the straps were on my shoulders, marvelling at the thrilling sensation of the dress sliding up over the sheer nylon stockings. I reached round and zipped up the back. It was a nice snug fit, it was great to feel how it sat on my body and how the skirt swished around my smooth stocking-clad legs.
Next it was the shoes. I sat down on the bed for this, carefully smoothing the skirt of the dress under my legs so that it didn't get crushed. I put the left hand one on first. She was only a size or 2 smaller than me so it fitted fairly well, as I slid my foot in the front and fastened the elastic strap behind my ankle. Then the same with the right foot. I stood up again, now 3 inches taller than normal because of the heels, but still a few inches shorter than Jonathan. It felt fantastic, perched on sexy high-heels, dressed in a such sexy clothes, with a pair of wet panties clinging to my crotch. I felt 100% woman, and 100% slut.
Jonathan was still slowly stroking his huge cock, but now he moved over and taking my arm guided me over to a full length mirror hanging on the bedroom wall. To myself I looked really sexy and dirty. Some make-up and jewellery and some clips in my hair and I would have looked very convincing. As Jonathan started to run his hands over my body though, I knew by just one glance at his juicy throbbing cock that there wasn't going to be enough time to put on any make-up first!
I could feel his big stiff thick cock pressing against against the small of my back, and by God I wanted it, I wanted to behave like a dirty randy slut and feel that beautiful hunk of meat inside me!
I turned around, and got down on my knees in front of him. Jonathan peeled back his foreskin and pressed his big smooth purple cock head against my lips. It was huge, but I really liked the smell, and I wanted to taste it in my mouth. I wet my lips with my tongue, and sliding them slowly over that glistening cock head I let a good 4 inches of the shaft slide into my mouth.
It really was massive, my mouth was wide open but it was still stuffed completely full of cock. It tasted so good, and felt so good too! I wondered if it was good for Jonathan, if my warm wet mouth felt good on his cock. It seemed so, as he started to moan, and thrust his proud erection in and out of my mouth. I responded in kind, moving my head backwards and forwards to meet his thrusts, and sucking hard on his rock hard manhood.
I felt deliciously slutty and subservient, kneeling down like this in the sexy dress and stockings, serving a dominant alpha male like this. I was wondering how his cum would taste, when Jonathan groaned loudly, then quickly pulled his shaft out of my mouth.
"Any more of that and I'm going to come Samantha" he explained. "I will come in your mouth later, but I think for the first time I'm going to fuck you senseless and cum deep inside you."
This was exactly what I had longed to hear, I stood up on the sexy high-heels as best I could, with my legs quivering like jelly. My cock felt like it grew even bigger and harder, although I'm not sure how that was possible, as I was already so excited. I threw my arms round his neck and gave him a slow, lingering kiss.
Jonathan lifted me in his strong arms, then strode the few steps to the big double bed before throwing me onto it on my back. My God! He tore of his shirt and stepped out of his trousers. I was already about to cum just from looking at his naked muscular body and his proud erect cock.
Lying on the bed like that with him moving in on me I suddenly felt a rush of wanton desire. I reached down and pulled the cocktail dress up to my waist, exposing the stockings and suspenders, and also the skimpy panties with my 7" erect cock poking out over the top of the lacy elastic waistband. I drew back my legs a bit and spread them slightly to show him the crotch of the panties.
He moved in and grabbed the elasticated waist, before slowly pulling the panties away from my cock and balls and slowly down over my stocking tops. The sensation of the panties being pulled off over my skin was incredible. He slowly pulled them down over my smooth nylon clad legs before getting them off of my left foot. He left them dangling from the high heel on my right foot, a nice touch. Holding both my ankles tight I felt him push my legs back, until my bare virgin hole was completely exposed and at his mercy.
Suddenly his beautiful big purple cock head pressed against my tight little anus. I gasped, it was as if I'd been hit with a jolt of electricity. He started to press it in harder, and move it around, teasing my naughty little hole. I could feel his copious slippery love juices being transferred from his cock to my hole, and I realised that there would be no lubricant involved. That scared me a bit, his cock was so big!
Now he started to push forward in earnest. His big slippery cock head was testing my defences, pushing harder and harder against my tight hole. It began to feel sore, as he managed to part my anal lips with the very tip of his cock. Now he started to push really hard and I felt my hole being stretched wide as it rode a bit further up his cock head. He pulled out slightly then thrust forward again. The pain suddenly became intense as he grunted and rammed his huge stiff cock forward. I felt that big cock head suddenly clear my tightly stretched anus and slide 2 or 3 inches inside me. I had lost my virginity! For the first time in my life a big stiff cock had penetrated my hole and stuffed itself up my rectum.
Jonathan grinned and started to slowly thrust his cock in and out of me. The length of cock that slid up inside me got greater with each thrust, until I could feel his belly slapping against the base of my cock and his huge balls swinging against my buttocks. The pain was mostly gone now and the feeling of being filled up by that amazing hunk of man-meat was incredible. It was so big that it was hard to believe that it would all fit inside me, but I'd managed to take it right up to the hilt. It felt like I was being stretched in every possible way by his big thick shaft as he slid it in and out of me.
The pleasure was so intense that I started to moan gently. This got Jonathan really excited and he started to give me a serious fucking, pounding his meat like a piston in and out of my eager slippery hole, and talking dirty to me.
"Yes you love it don't you, you filthy little slut? Flat on your back with your panties off and your stocking clad legs up in the air for me. You're going to cum aren't you, you dirty slut?"
He wasn't wrong, I could feel the most wonderful orgasm mounting as his strong cock continued giving me my first ever fucking, the sensation as his cock slid backwards and forwards over my prostate gland was driving me crazy, this was going to be a far stronger orgasm than anything I'd ever achieved through masturbation.
"Cum bitch!" he shouted ramming his cock even harder into slutty tranny hole, "I want to see you squirting you dirty pervy little girl."
This was enough for me, I couldn't hold out any longer. I started to scream as his thrusting cock drove me to orgasm, and suddenly as it hit my whole body shook and I saw flashing colours and felt my cock twitch violently and start to squirt spunk all over my belly and suspender belt, even right up over the sexy dress and onto my neck and throat.
"That's it, squirt for me you slut" he shouted as my cock shot spunk all over the place.
After what seemed like 8 or 9 jets had shot out, my blinding orgasm began to subside, and I whimpered as less powerful contractions of my prostate squeezed the last of my spunk up my cock to come slowly oozing out of the tip.
The sight of me cumming like that had made Jonathan even more excited, he was now fucking me harder than ever. I was held very firmly with my legs pinned back and my high-heels up round my head as his cock went faster and faster in and out of me.
"That's it, I'm cumming, I'm cumming" roared Jonathan as his furious pounding reached a crescendo, and suddenly gasped and growled loudly and I felt his cock twitching inside me as he spurted all his lovely creamy goodness deep inside me. His orgasm seemed to go on for ages as he discharged the heavy load that was in his huge balls, and I felt more and more spunk being pumped up my greedy tranny cunt.
Finally he was finished, and he smiled as he slowly pulled out his still huge but now softening cock.
"My God, that was fantastic" he said as he rolled over to lie beside me on the bed.
I couldn't do anything other than gasp "yes!", as I lay there recovering from the outrageous fucking he had just given me. Then a felt another amazing sensation, as something warm and slippery and liquid started to trickle out of my hole. Jonathan had left so much spunk inside me that it was now almost gushing out of me, and my first ever cream pie felt so very good as it oozed out of my stretched anus and trickled down my buttocks.
The next 8 weeks were like heaven, as soon as work was finished I would rush off to Jonathan's house to stay the night, or the whole weekend. I was wined and dined, dressed in his wife's underwear, clothes and shoes, sat in front of her dressing table to put on her make-up and jewellery, and even taken out for the evening while dressed. But most of all I was treated to 2 months of red-hot almost non-stop steamy sex.
Unfortunately all good things must come to an end, and the morning of the day his wife came back home was the last time I ever saw him. But this is not the last tale of my time with Jonathan, the next story will be about one very special evening he set up for me towards the end of our time together.