How I Got Started...
So how did I start crossdressing and hooking up with men? Well, here's a concise version of that story...
I'd been playing dress-up with my sister since I was about 4 and it had just been a game youngsters played, but I remember one Saturday night when I was 10 thinking about how I used to do that and almost daring myself to do it again but this time fully, wearing a bra, knickers and tights as well as a dress. I remember it was a Saturday because my mum would always take us to our nans on Sunday afternoons so I had decided to make an excuse to stay home this time. So that Sunday afternoon after they had gone, I went into mum's room and did as I planned. I stayed dressed in her clothes for a couple of hours and while it was initially because of enjoying the thrill, it soon changed to enjoying how it felt to wear them. I knew this was something I wanted to do more often.
I kept this secret for a few years but one day when i was 13 i let it slip, unintentionally. I was round my next-door neighbours house and it was just him and me there. We were playing dares and he dared me to put on his mum's clothes. I pretended to be shocked and reluctant and all that, but of course inside I was thrilled at the chance, not just to wear his mum's clothes but to be with someone else at the same time who could see me in them. Bear in mind I was 13, this was 1985 and there was no internet, so I thought I was the only person who liked doing this. Anyway, where I slipped up was that instead of pretending to not know how to put on a pair of tights, or how to put on a bra, I put them on in a way that clearly must have shown that I knew how to, and he noticed this. He didn't say anything, but at the same time must have liked it, because this was far from the only time I wore his mums clothes while there. It wasn't until I was around 15-16 that I started to buy lingerie, clothes and shoes for myself, so until then the only chance i had was either at home when i was alone, or round my neighbours house while his parents were out.
Initially there was no sexual contact when i was playing dares with my neighbour... but that did change. There was often a lot of nudity involved, which then changed to him stripping off while i'd be dressed in his mum's clothes, so there was often a very sexually charged atmosphere. While I had unintentionally given away that I crossdressed, he also unintentionally (or maybe not) gave away that he liked seeing me dressed as he not only dropped the whole dare thing regarding it and would just ask me if I wanted to change into his mum's clothes, but he would also have picked out a particular dress or skirt and top that he wanted me wearing at that time. The dare game continued but by now it was little more than a thin disguise for allowing us to "experiment". The first physical contact with any sexual connotation had me kissing his bum, which I loved doing. That eventually became a routine to the extent where I would be dressed, he'd be laying on the bed and we'd be chatting as I kissed it over and over. The dares started up again and that was when I first had a cock in my mouth. First time it was just literally that, he held his cock steady while I put my mouth around it, but the only contact between my lips and his cock was when I closed them once it was in. The next time was more like a blow job in that I slid his cock in between my lips when taking it in and again when taking it out. The third time would actually be considered a blow job, i slid his cock between my lips and had them sliding up and down it over and over while also sucking, though i didn't use my tongue. Maybe that's why he didn't cum although to this day I have no idea how he didn't since he really was rock hard and leaked a lot of precum. So I guess I was 14 when I gave my first blowjob... he was a year older. Sadly they moved house a few months later so that was the last time I did anything with him, so although I still enjoyed dressing privately at home, it lacked the intense sexual atmosphere that had developed when I would be next-door.
So as i mentioned before, once i was 15-16 i had started buying my own outfits, lingerie and high heels, and it felt even better knowing that i was wearing my own outfits, not just what my mum had. And it was around this time i finally discovered that i wasn't alone, that there were other crossdressers and transvestites. Now that i knew what to look for, i began to read about it and found adverts from other CD/TV's in the lonely hearts columns of the local paper and in things like the Exchange & Mart. Once i reached 18 i started putting my own adverts in and remember being amazed by the response i got to my first advert. This lead to my first encounters with another CD/TV and with a man i'd never met before, but those are stories for another time...
Tina xxx
If you want to read more, please let me know xxx
I'd been playing dress-up with my sister since I was about 4 and it had just been a game youngsters played, but I remember one Saturday night when I was 10 thinking about how I used to do that and almost daring myself to do it again but this time fully, wearing a bra, knickers and tights as well as a dress. I remember it was a Saturday because my mum would always take us to our nans on Sunday afternoons so I had decided to make an excuse to stay home this time. So that Sunday afternoon after they had gone, I went into mum's room and did as I planned. I stayed dressed in her clothes for a couple of hours and while it was initially because of enjoying the thrill, it soon changed to enjoying how it felt to wear them. I knew this was something I wanted to do more often.
I kept this secret for a few years but one day when i was 13 i let it slip, unintentionally. I was round my next-door neighbours house and it was just him and me there. We were playing dares and he dared me to put on his mum's clothes. I pretended to be shocked and reluctant and all that, but of course inside I was thrilled at the chance, not just to wear his mum's clothes but to be with someone else at the same time who could see me in them. Bear in mind I was 13, this was 1985 and there was no internet, so I thought I was the only person who liked doing this. Anyway, where I slipped up was that instead of pretending to not know how to put on a pair of tights, or how to put on a bra, I put them on in a way that clearly must have shown that I knew how to, and he noticed this. He didn't say anything, but at the same time must have liked it, because this was far from the only time I wore his mums clothes while there. It wasn't until I was around 15-16 that I started to buy lingerie, clothes and shoes for myself, so until then the only chance i had was either at home when i was alone, or round my neighbours house while his parents were out.
Initially there was no sexual contact when i was playing dares with my neighbour... but that did change. There was often a lot of nudity involved, which then changed to him stripping off while i'd be dressed in his mum's clothes, so there was often a very sexually charged atmosphere. While I had unintentionally given away that I crossdressed, he also unintentionally (or maybe not) gave away that he liked seeing me dressed as he not only dropped the whole dare thing regarding it and would just ask me if I wanted to change into his mum's clothes, but he would also have picked out a particular dress or skirt and top that he wanted me wearing at that time. The dare game continued but by now it was little more than a thin disguise for allowing us to "experiment". The first physical contact with any sexual connotation had me kissing his bum, which I loved doing. That eventually became a routine to the extent where I would be dressed, he'd be laying on the bed and we'd be chatting as I kissed it over and over. The dares started up again and that was when I first had a cock in my mouth. First time it was just literally that, he held his cock steady while I put my mouth around it, but the only contact between my lips and his cock was when I closed them once it was in. The next time was more like a blow job in that I slid his cock in between my lips when taking it in and again when taking it out. The third time would actually be considered a blow job, i slid his cock between my lips and had them sliding up and down it over and over while also sucking, though i didn't use my tongue. Maybe that's why he didn't cum although to this day I have no idea how he didn't since he really was rock hard and leaked a lot of precum. So I guess I was 14 when I gave my first blowjob... he was a year older. Sadly they moved house a few months later so that was the last time I did anything with him, so although I still enjoyed dressing privately at home, it lacked the intense sexual atmosphere that had developed when I would be next-door.
So as i mentioned before, once i was 15-16 i had started buying my own outfits, lingerie and high heels, and it felt even better knowing that i was wearing my own outfits, not just what my mum had. And it was around this time i finally discovered that i wasn't alone, that there were other crossdressers and transvestites. Now that i knew what to look for, i began to read about it and found adverts from other CD/TV's in the lonely hearts columns of the local paper and in things like the Exchange & Mart. Once i reached 18 i started putting my own adverts in and remember being amazed by the response i got to my first advert. This lead to my first encounters with another CD/TV and with a man i'd never met before, but those are stories for another time...
Tina xxx
If you want to read more, please let me know xxx
4 years ago
