Really hot early crossdressing and sexy adventues.

Carrying on from my story about my visits to Ron Manning and his sisters house and their sexy dirty little antics I did remember one period very vividly and fondly xx

I was getting a bit older now and I wouldn’t say I was getting ‘bored’ with going to their house most Sundays but it was always the ‘same’ and I’d started to discover girls, especially one called Carol. I think all my older men ‘friends’ who’d used me over, probably, the last five or six years were also aware that I was no longer the little boy they could manipulate and use for their sexual gratification. Having said that I was still enjoying the attention they showered on me, certainly the sex was still great, very much so, but things were changing. I’d stopped going to scouts and although I was still being used occasionally for sex by mr Vaughn I didn’t see him half as much as I used too however i still had the occasional trip into the countryside, trips to London with him or to the cinema to wank him off and his man friends.

The other aspect was that I was shooting up height wise, filling out a bit and when Ron and auntie Mary dressed me up as a little schoolgirl, which they did more and more often I think I was beginning to look a bit silly!! I loved the dressing up and them playing with me but like the other stuff, I was wanting more. It was about this time that Barry, who I’ve mentioned before and was about five years older than me, let me into his secret. Apparently he’d ‘discovered’ prostitutes!!!! Barry was probably more sexually driven than I was and loved sex in any shape or form and with anyone, or anything and anywhere, he was insatiable sex wise. He’d recently got a job, earning quite good money, which also included a firms car, a new ford cortina. Barry, unlike me, still saw mr Vaughn and his man friends regularly for gay sex and he also had a girlfriend called Anita who he was fucking whenever the opportunity arose, so he wasn’t being neglected in the sex department. It wasn’t enough for Barry though and now he had his car and a bit of cash he was also frequenting the local red light area. I don’t know how he found the time or the stamina but there you go!!

One night Barry invited me round to his bedroom (he was still living at home with his parents at this time) and after we’d both wanked and sucked each other off on his bed he suggested we could go for a drive. I think it was probably the first time I’d been out driving that late at night and definitely the first time I’d been to the red light area when it was in ‘full swing’ as you might say! It was amazing and I was completely knocked out by, not only by how many girls and women there were, standing on street corners, but how incredibly sexy they all looked in their short skirts, stockings, high heels, skimpy tops and tarty makeup. I loved it !!!! Of course Barry did too and before long I’d been ordered into the back seat and Barry had made his selection. I thought there were better looking ones than the one he picked but he seemed keen on her. She was in her mid to late twenties but she could have been a bit older with peroxide blond hair, probably the shortest mini skirt on show that night, stunning stocking clad legs, high stilettos and a skimpy tee shirt that did little to cover her ample breasts squeezed into a half cup bra. Barry soon agreed a price which, if I remember rightly was a fiver for full sex. Barry wanted to fuck her bareback but she wasn’t having that and made him put on a rubber. The cortina had a bench seat in the front so that’s where they did it. Initially she wanted another two pounds as I was going to watch but Barry talked her out of that. Barry was a bit of an a****l when it came to sex and I’m pretty sure she knew it too, by the time he’d finished with her. I suppose he’d fucked her for five or six minutes before he’d cum but I’d loved it and loved too listening to her ‘dirty talk’, her stockinged legs d****d over the seat not inches from me and the smell of cunt and her cheap perfume. I was hooked and I have to admit I cum in my pants. I couldn’t wait to have one myself!!!

A couple of weeks later I was again having Sunday dinner at Ron and auntie Mary’s and after we’d had our usual ‘sex’ games, I’d told them about my little adventure with Barry and how much I’d enjoyed it and everything about the whole red light area and ‘prostitute’ thing. Both Ron and Mary both agreed with me that things had to change but they were reluctant to lose me completely and offered to help me ‘progress’, as they put it. They’d already been thinking of changes and me telling them about ‘prostitutes’ only got them planning even more exciting things. One of the aspects of my ‘growing up’ that they’d noticed, Mary in particular, was how much I enjoyed wearing women’s clothes, well girly really, and how it made my cock so big and hard and that they could definitely help me there!

The next week things were very different!!! For starters they told me I had to tell my parents that although I was going to Ron and auntie Mary’s house for dinner, it was now going to be later in the evening and I could be late getting home. When I arrived, Ron was there waiting for me with a big smile on his face, which was unusual for Ron as he was quite a serious person. What shocked me though was Mary, who appeared dressed, and there’s only one word to describe it, as a ‘whore’. Mary, although by now in her late fourties’, didn’t have a bad figure, scrubbed up well and she did love sex, was dressed in a very very short white leather look mini skirt, black stockings and suspenders, quite high heels (high for Mary anyway!!) and a sort of lurex black top which made no effort to cover her large breasts which were encased in a black lacy bra. I think I’d mentioned before that Mary’s cunt was very hairy and the skirt was so short that it was obvious that she’s wasn’t wearing any knickers as I could see her hairy cunt. Ron explained that we weren’t having a dinner that evening, only a sandwich and that we were going out ‘curb crawling’ around the red light area looking at the prostitutes which I was well up for! As it was a Sunday night there didn’t seem to be as many on the street corners as when I’d gone with Barry but there were still plenty to ogle at and some of them looked even more amazingly sexy than last time. I sat in the back with auntie Mary who seemed to be, surprisingly, enjoying it as much as I was especially as she soon had my cock out and her short skirt offered me no hindrance to playing with her by now wet cunt. Ron cruised around stopping to talk to a couple of the women asking them what they did and how much? One particular one looked really over the top, dress wise, compared to the rest. She was probably one of the youngest ones out that night, probably not much older than me and was wearing a red plastic skirt, no more than about four inches deep, beautifully long oiled tanned legs, red high stilettos, white cotton knickers, which you could see and just a boob tube top. She looked so young and innocent but incredibly sexy. I’d have gone with her in a flash but it was obvious that Ron and Mary had other ideas for me.

After a while Ron stopped the car and Mary got out and walked off down the street really looking the part tottering on her high heels. I got in the front with Ron and we both watched as Mary stopped on the street corner, hitching up her skirt even higher, soliciting for business. Ron and I both had our cocks out, giving each other a nice leisurely wank whilst watching Mary, who, again surprisingly, seemed to be very much entering into the spirit of the evening. Several cars drove by and after two or three stopped to talk to her, she decided to get in a green jaguar, driven by what looked to be a middle aged businessman. I’m not sure if this was part of the plan but before Ron and I could sort ourselves out she was gone! We did try to follow her but to no avail and returned to our parking spot, Ron definitely very worried. After about twenty minutes Mary came tottering back around the corner with a smile a mile wide on her face. I don’t think Ron’s heart would take much more excitement so off we went home. We couldn’t shut Mary up as she went through every intimate detail of her sex with the punter. They’d apparently gone up a deserted lane and he’d fucked her hard up against the car as he didn’t want to soil the leather seats, which was fine with Mary!! He’d not worn a rubber (he’d told her the girls usually charged more for bareback!!) and, according to Mary had given her a good seeing to and by the amount of spunk dripping out her cunt and down her thighs he had been a very heavy cummer. Oh and he’d given her a fiver, the going rate!

When we got home we all had a sandwich and a cup of tea but auntie Mary was definitely on a sexual high and couldn’t keep her eyes or hands off me and mine off her, for that matter and before long the pair of us were fucking like rabbits on the living room floor watched excitedly by Ron, wanking himself off furiously. It was unusual for me to fuck Mary but that night she was insatiable and, up to that time, one of the best fucks I’d ever had! Big, very wet cunt and so very sensual xx

The next weekend (I was down at their house more than at home now it seemed!) it was obvious that again we were going to the red light area, Mary again dressing like a prostitute, even more so and definitely more up for it than the week before. This time though they wanted me to dress as a prostitute too which, at first, I was not too keen but when Mary showed me what they’d bought for me I was won over. Like I said earlier, I was now filling out but still quite slim and probably about five foot ten tall. I’ve always looked quite feminine so I just handed myself over to Mary. They’d really pushed the boat out clothes wise! First of all she fitted me with my beautiful little pink satin bra, pink knickers and matching suspender belt, the feeling of which was wonderful, and then my stockings. I’d never worn stockings before, well properly anyway, and they were lovely and sheer and I adored immediately that special feeling that all stocking wearers know only to well xx I was starting to feel a million dollars and when Mary showed me my amazing skimpy tart dress I think I started to cry and when she showed me my heels, wig and makeup case I certainly did. Once she’d finished with me I couldn’t stop looking in the mirror, I thought I looked gorgeous, my wig back combed, my make up amazing and my lovely four inch stilettos, gosh I looked the part! And more importantly so girly, feminine and whorey looking xx

Of course I’d been with lots of men before but never in this environment so I was as nervous as hell. The plan, there was always a plan with Ron, was that we’d go down to the red light area and both Mary and myself would see if we could attract a punter. As it was the first time for me, Mary would take the lead and tell the punter I was her daughter and new to the game, which seemed a good plan. I definitely wasn’t prepared to be fucked but I did say I would have oral sex if they wanted it which was fine with Ron and Mary. When we got out of the car I was a bit unsteady in my heels but by the time we got to the corner I was sort of okay. I was holding on to Mary anyway, quite tightly, I can tell you!!! On the next corner was the young prostitute we’d seen the week before looking as stunning as the last time I’d saw her. She was with a very tall black girl, about the same age, and very pretty too. Both were dressed in not very much as it was quite a warm sultry evening and showing off their wares to full advantage. She waved to Mary but obviously or hopefully didn’t recognise me which wouldn’t have done my confidence much good. We’d been there only about five minutes or so before a couple of cars started to ‘circle’ us. The first one to stop and ask us if we were ‘available’ was a older looking man who looked a bit rough around the edges so Mary sent him on his way but the next one seemed more to her liking. For a woman in her forties who’d never worked the streets before, she was acting like a real pro and had soon agreed for the pair of us to go with a young Asian guy who was quite prepared to just fuck Mary whilst her ‘daughter’ watched. Mary got in the front whilst I got in the back and was soon directing him to the same quiet lane she’d taken her previous customer. It certainly was a great secluded spot, no one around at all.

Mary had taken complete control and directed all of us to get out of the car whereupon she led back on the bonnet of the car, brazenly opened her legs, hitched up her already obscenely short skirt exposing her knicker less hairy cunt and directed me to sort his cock out. I don’t think he’d ever had two ‘prostitutes’ servicing him and offered no resistance as I dropped his jogging bottoms and pants and, squatting in front of him took his semi hard cock in my mouth. I’d done this loads of times and, if I say so myself, gave a pretty good blow job back then and he was soon rock hard. I think I heard him say that he wanted to fuck the ‘younger one’ but Mary wasn’t having any of that and pulled him onto herself, her hands helping to thrust his loins into her demanding cunt. He didn’t last long and, like the time before, Mary hadn’t asked him to wear a rubber and once again her hairy cunt was covered in spunk. I can’t begin to describe the sheer feeling of excitement, pleasure, happiness, danger, contentment all rolled into one. I think it was the best experience in my life up to that time without a doubt and the icing on the cake was that he’d had no idea that I wasn’t a ‘girl’.

Back we went to Ron, patiently waiting for us in the car, who wanted to know every sordid detail both of what I’d done and Mary too, but before that, he demanded that I suck his hard cock off and I think he had the heaviest and strongest cum I known him have. Gosh I felt good, loved being dressed as a whore as obviously Mary did too and when we got home we again had an amazing fuck on the living room floor only this time we both stayed dressed in our ‘whore’ outfits and I fucked Mary while sucking Ron, who was knelt down beside us telling us both how amazingly sexy we both looked xx I wanted to keep my whores clothes on as I felt so good but come the end of the evening Mary and myself had to change back into our dreary ‘normal’ clothes but not before Mary and I had both had a bath together soaping each other down and ending in yet more sex. What a night but it wasn’t to be our last foray into the sexier deeper side but it did start me off on a cross dressing journey that I’m still on today and a lifetime fascination with ‘prostitutes’.