First crossdressing experiences - old man in hotel
As a young teenager, I remember getting a bit of a cheap thrill whenever I found some knickers or ladies underwear where we played as k**s, usually under bridges and tips etc. But it wasn't until I was in my early 20's, when I realised that there was anything other than peeing to be done in a public toilet. I discovered a large public toilet with very small holes in the adjoining wooden walls - this certainly opened my eyes. I was (and am) straight, but seeing guys playing with their cocks for all to see was such a thrill. First day I just watched one guy playing with himself. After a day or two I had seen several, and then it happened, some guy in suspenders and stockings wanking himself off - I was amazed, thrilled, super horny, I still remember it to this day.
Within a few days I was in there, wearing my girlfriends gear, just sitting there with my cock pointing upwards between my stockings and suspender belt - getting lots of messages slipped under the walls to me. That was enough for me for a long time, I was happy to wank myself off in undies whenever I could.
By the time I was in my mid twenties I had a good job that involved a lot of travel and hotels. My thrill by that time was to leave my hotel late in the evening, and go out running in some super tight lycra dance shorts in the dark. It gave me a monster hard on. I loved the occasional car going past and knowing they couldn't miss my bulge in the headlights.
Eventually I had my first real contact with another man. I was in a hotel near the M5, and I had a few drinks with dinner and got chatting to some other suited guys in the bar. It was just a few words here and there watching football. By the time it got towards midnight, it was just myself and an older stocky guy with a moustache and slightly posh accent. His name was Derek. We chatted away a bit more and he was asking if I was married and this and that, and he got round to talking about the time spent away by guys in hotels. He started talking about dirty magazines he found under beds in hotels rooms ( the internet was in its ******y at this point), and jokingly asked me if I wanted to borrow some. I had had a good few drinks by then, and said "too right". He told me to drink up and we went back to his room. The mini bar was soon opened and he was sort of joking about putting a porn movie on. I said I was uncomfortable with that - and I was. I wasn't really up for what I was beginning to suspect was a gay encounter. Anyway, he got a huge stash of Magazines out - 80's glamour mags, my favourites, Razzle, E***** etc, loads of nice undies on show. We both agreed they were great, and I was starting to feel horny as he poured me another drink. Then he threw down another few mags - German I think they were, a lot of the pics in black and white, and he told me these were his favourites. My eyes nearly popped out when I looked. Typically lots of huge breasts in leather etc, but then....... several pages of men in ladies underwear, suspenders, heels stockings girdles etc and lots of big hard cocks. Derek asked me if I liked that, and I said I did. I was so thrilled and horny and shaking, I'll never forget it.
He told me to enjoy, and he would be back in a sec and he disappeared into the toilet. When he was in the loo, I could help but give myself a quick feel through my trousers. My heart was hammering in my chest. I heard Derek come back out of the loo as I sat facing slight away on the bed looking at the mag. I could sense him a couple of feet away and hear his breathing, so I very quickly glanced up and caught a bit of reflection in the mirror. Good god, he was standing there in big white knickers and some tan stockings. My face flushed red hot. He walked right up to the edge of the bed and I could see his cock stiff through the fabric. It wasn't very big, but look like it was rock hard.....................I'll never forget the next ten minutes.
Within a few days I was in there, wearing my girlfriends gear, just sitting there with my cock pointing upwards between my stockings and suspender belt - getting lots of messages slipped under the walls to me. That was enough for me for a long time, I was happy to wank myself off in undies whenever I could.
By the time I was in my mid twenties I had a good job that involved a lot of travel and hotels. My thrill by that time was to leave my hotel late in the evening, and go out running in some super tight lycra dance shorts in the dark. It gave me a monster hard on. I loved the occasional car going past and knowing they couldn't miss my bulge in the headlights.
Eventually I had my first real contact with another man. I was in a hotel near the M5, and I had a few drinks with dinner and got chatting to some other suited guys in the bar. It was just a few words here and there watching football. By the time it got towards midnight, it was just myself and an older stocky guy with a moustache and slightly posh accent. His name was Derek. We chatted away a bit more and he was asking if I was married and this and that, and he got round to talking about the time spent away by guys in hotels. He started talking about dirty magazines he found under beds in hotels rooms ( the internet was in its ******y at this point), and jokingly asked me if I wanted to borrow some. I had had a good few drinks by then, and said "too right". He told me to drink up and we went back to his room. The mini bar was soon opened and he was sort of joking about putting a porn movie on. I said I was uncomfortable with that - and I was. I wasn't really up for what I was beginning to suspect was a gay encounter. Anyway, he got a huge stash of Magazines out - 80's glamour mags, my favourites, Razzle, E***** etc, loads of nice undies on show. We both agreed they were great, and I was starting to feel horny as he poured me another drink. Then he threw down another few mags - German I think they were, a lot of the pics in black and white, and he told me these were his favourites. My eyes nearly popped out when I looked. Typically lots of huge breasts in leather etc, but then....... several pages of men in ladies underwear, suspenders, heels stockings girdles etc and lots of big hard cocks. Derek asked me if I liked that, and I said I did. I was so thrilled and horny and shaking, I'll never forget it.
He told me to enjoy, and he would be back in a sec and he disappeared into the toilet. When he was in the loo, I could help but give myself a quick feel through my trousers. My heart was hammering in my chest. I heard Derek come back out of the loo as I sat facing slight away on the bed looking at the mag. I could sense him a couple of feet away and hear his breathing, so I very quickly glanced up and caught a bit of reflection in the mirror. Good god, he was standing there in big white knickers and some tan stockings. My face flushed red hot. He walked right up to the edge of the bed and I could see his cock stiff through the fabric. It wasn't very big, but look like it was rock hard.....................I'll never forget the next ten minutes.
8年前
