This is a series of stories rather than one story. It talks of my experiences as a crossdresser.
My first experience as a crossdresser came as a teenager when I tried out some of the clothes belonging to a woman who was staying at our home. She was a gorgeous French woman with very pretty clothes and I did enjoy trying them on, but primarily as it got me closer to this woman who was way out of my league.
When away from home the first time I bought a few clothes through a mail order catalogue - a dress, one-piece swimsuit, skirt, nightwear and lingerie. I tried them on and slept in the nightwear but I thought that I looked foolish when I saw myself in the mirror and soon discarded the clothes.
My primary attraction was towards women and I had girlfriends but not a lot of success in getting them into bed, though the times I did succeed were good for me. However, I did have an attraction from a fairly young age to men, specifically to their butts. I didn't see men and think, 'I want to have sex with him' but I did see men's butts and think 'nice butt, I would like some of that'.
My first sexual experience with a man, maybe 25 years of age, came when I was 18. We were both taking a train through Europe and he invited me to come to his apartment when we got to his hometown of Amsterdam. I hadn't really noticed his ass and my first thought after his invitation was that I would have a place for a nice shower, which was going to be welcome after a few days travelling. On the way across town to his place it dawned on me that he had more in mind than showing me his home town and indeed, right after that welcome shower, I was led to his bed and soon having my first experience of being fucked.
I liked it enough that we stayed in that bed for most of 36 hours before I decided that I had better get back on the train. My next man came at the end of university when one of my classmates, whom I had spent plenty of time with going to bars, working on papers and just chilling, admitted that he was attracted to me and that, though he knew I had no interest in him, would I be willing to go off with him for a weekend. I pretended to be innocent and go with him to chat but within a few minutes of arriving at the hotel he had succeeded in persuading me to take a shower with him and another 36 hours spent primarily in bed was enjoyed.
A good decade or more later, I returned to college to get a practical qualification to go with my degree. I had a nice girlfriend for much of that time and had had a few in the intervening years as well, feeling quite content to leave gay sex as a distant memory (even if butts did still catch my eye from time to time. After breaking off with the girlfriend (she graduated earlier and headed home) I tried a one night stand with a bar pick-up which was not really satisfying in any way.
But I left college completely broke and unable to get work right away. I was surviving on the part-time job I had when I was a student but this barely paid the necessities of food and rent. So, when a job offer did come, I was not sure if I could accept the offer as it meant moving to a new city and I had no money for the move or for first and last rent.
This was in the early days of wider access to the Internet and one site I had found was an early gay dating site. I had set up a profile and emailed with a few people but not really tried to make things happen. When this job offer came, though, I had started to email a guy in the town that I was moving to and I mentioned my predicament to him. He had a ready answer - come live with me!
In those days with dial-up access and no digital cameras, photographs were hard to get online. All I knew of this guy was his alias and what he said in his profile, which need not have any relationship to reality. So we agreed to meet - to see if we were compatible and to work out an arrangement if we were.
He came by one Saturday. As his profile said, he was 50 years old, a computer professional, long-time out of the closet but a masculine gay, and I was much of what I had said I was - 33, bisexual, broke. I stayed the night in his hotel room where he demonstrated his preference for sensual, slow, intimate sex. The best sex I had enjoyed
We agreed to go through with the plan and a week or two later he came by to pick up my stuff and take me to his spotless two bedroom condo on the outskirts of the gay section of the city. My stuff was parked in the second bedroom (never to be touched!) and I moved in with him to his room. The agreement was for me to stay until I could get myself established so I was paying only for food and my personal expenses. We estimated I would stay two-three months. He wasn't interested in me in the long term as I was in the closet and planned to stay there.
In his profile he'd talked about candlelit dinners, candlelit baths, slow and sensual sex, and sensual massages. All of that was true. What he had not mentioned, perhaps as it was not on his mind at the time, was what he wanted me to wear.
On my limited budget I had college clothes, mostly worn and tired. Any money I made first went to buying a new wardrobe. He didn't like my old wardrobe and didn't like the idea of wearing office clothes at home. So he went shopping for me. And here was the unexpected novelty. The clothes that he bought for me were smart women's outfits - lingerie, nightwear, skirts, dresses, sweaters, jewellery, makeup, wig and shoes. Smart casual outfits for the home.
He told me that he had never had a crossdresser as a boyfriend and had not had this idea for me until I had arrived at his apartment. I was a temporary partner and for him, he said, this was a temporary experience. Perhaps this was part of his justification for taking in a temp boyfriend. He did treat me as a boyfriend, bringing me along with him to dinners and drinks with (non-work) friends, though on those occasions I wore my own, male, clothes.
For the five months I stayed with him, I lived in the clothes that he bought for me any time I was in the home. He told me I was a good looker even though, when I looked in the mirror, I felt I looked like a guy trying out dresses for the first time, unconvincingly.
We rarely had sex with me dressed in the clothes (excepting the odd blow job) but he loved to undress me and loved to have sex with me wearing one or two pieces of lingerie or any nightdress or nightshirt. He wanted me naked, though, whenever I entered him.
I got to rather enjoy dressing as a woman, not least of all because they were very attractive and good quality clothes. When I did leave, though, he allowed me to take only a single pair of panties with me. The rest he threw out with the trash.
In my new job I hooked up with a pretty co-worker for a good long but solely casual relationship (her parents wanted her to marry a fellow Indian so I would never be allowed to be her real date) and I was quite happy leaving men behind. I had enjoyed the older man and the sex was the best I had had (with any gender) but sex with this woman, and a few others after her, was more relaxed and fun.
Then I got married, had a good decade with my wife and barely thought about guys, even if I did see a nice ass.
Sadly, my wife passed away and for a good long time no woman or man was of any sexual interest to me. Then I started back onto the singles web sites and put up profiles on both straight and gay sites. I met one guy in a hotel for the worst sexual experience I had had (way too much wiry hair!) and then corresponded with an older man.
I can't remember why I ever wrote with him in the first place other than perhaps he was not interested in anything long term. He had a cottage and was looking for a man to join him on the weekends in the summer. Maybe being by the beach was what interested me? I was now into my 40's, while he was 60 and retired (but working part-time for fun). He admitted in his profile that he was a bit overweight and when we had coffee together he was indeed rather large. But I went with him the following week anyways.
His cottage was on the water but quite private so we were able to spend the day hanging out by the water and relaxing. After dinner it was time for fun so we went to his room where he brought out a little collection of vibrators (he admitted that sometimes he used them when his own tool was not cooperating) and got me to lie on my stomach. For a long time he played with my ass using his toys but then was able to get his own cock into shape and gave me a surprisingly enjoyable fuck.
He enjoyed the return fuck but it was clear his preference was to play with me. So I was not totally surprised when he brought out panties and a nightshirt for me to wear as he went back to playing with my ass. He was not into having me dress up for him as much except for bed time -though 'bedtime included sex on the lawn in front of the cottage after dark when we could see boats passing by but hoping nobody would make us out int he dark.
I spent perhaps half a dozen weekends with him, spending hours with him playing with my ass but also enjoying his a few times a night. Each visit came with a new selection of lingerie and nightwear and often a new toy for my ass. He also liked the occasional gay movie, which did not work as well for me.
After him, I had a brief relationship with another older, but much fitter, man and started to think that any future guys were also likely to be the older type.
Until I met Andrew.
He, like me, was a golf addict and we starter to meet up on the course quite often as we were of similar standard of play though his short game was better than miner and, despite the age difference, I could usually hit further than him. I had no notion at first that we would ever consider sex and I hadn't even particularly noticed his ass (I guess I assumed that it was off limits so hadn't wanted to be disappointed!).
But then I noticed him, as we sat having drink after a round, adjusting himself - and he saw that I saw him. The next round that we played he wore white trousers and I could see his grey briefs through the pants - and told him so. When we ended up in the woods later to look for a golf ball, he briefly opened his trousers and told me - and showed me - that they were in fact blue briefs. Again we found ourselves fiddling with our trousers in the clubhouse so, when we later got to our cars, he asked me if I was interested. I said yes, but was surprised about him.
In a two minute chat we determined that he just wanted to see if this was a fantasy or a preference and that he was not looking for a lover or partner, not that he wanted us to stop playing golf together if the sex didn't work out.
It worked out great.
We both loved slow and luscious sex, with brief high energy moments, and liked kissing during and after sex, which I wanted too. We enjoyed a few afternoons at my place but decided we wanted to spend the odd night together as well (though still not interested in a relationship). So we booked a twin room at a golf resort and had two days of golf and a night of very enjoyable sex. And we did it again a month or two later.
Now we wanted a little longer trip together so we went down to the US for a four day/three night golf trip. And here came the clothes again. As we drove to the resort from the airport he turned in to a Walmart and I wanted by the car as he quickly shopped and returned. That night, after we showered and returned to the room naked, I asked what he had bought and he, having not opened the bag in case I would think badly of him, nervously opened it up to show a six-pack of cute panties and four cute little nightshirts.
He admitted that he had always wanted to wear girls' clothes but only in private. So we quickly put on a pair of panties and a shirt and went to bed. Neither of us looked at all feminine but we both enjoyed working with these clothes and the sex, which had been good anyways, was especially fun and hot that night. Each day we hid the clothes in the rental car and then got dressed after our showers before bedtime.
Each trip thereafter we continued to stop on the way tot eh resort to get panties and tops and each time the sex was better and more fun than the few times we now came to my place for sex.
It all stopped, though, when a woman joined us. She knew about us, about the fun we had off the course, but she wanted us anyways and succeeded. We never told her about our panty fun but now we had new fun to play with so panties were no longer required. Being close to Andrew's age (25 or so), they would check in to the hotel as a couple and then come over to my room alone or together during the trip.
No more panties for now. For some reason guys like me to wear them but expecting a woman to do the same is too much to hope for.
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