Join the most popular community of UK swingers now
Login

Me and crossdressing

"From early days to the present"

19
8 Comments 8
1.6k Views 1.6k
1.9k words 1.9k words

It didn't used to be uncommon for two or more lads to engage in group masturbation, though without touching each other. But I had a best friend the same age as me who lived further up my road, we were inseparable, went everywhere and did everything together. We went much further with those sort of sessions, for in his house he used to strip naked and put on a pair of his mother’s nylon panties which he got out of her bedroom drawer, sometimes adding other things like a girdle and stockings or a slip. I would lay alongside him on his bed and fondle and feel him in his panties, while he wanked me off. He had a lovely smooth, hairless body and a nice cock. After he had made me cum, he would then finish himself off.

We did this regularly for about five years, in his house, in the countryside, camping, anywhere we could, and always with him in panties which he had obtained somehow or other, even to the extent of taking them off washing lines. We once did it in a cubicle in the park toilets, after which a man followed us out and asked, “Were you having fun in there?” whereupon we ran. I recall he once got hold of a girls' lycra swimming costume and put it on, when I squeezed his erect cock through the thin fabric. There was one occasion when I was laying on top of my face-down friend with his panties pulled down his bum cheeks and I was vigorously rubbing my cock off between the tops of his thighs, when he said, “You can put it in if you want.” It took me a moment to realise what he meant, but I declined, to me that was for doing to girls only.

We eventually started to follow different paths and drifted apart. My friend went on to get a girlfriend and marry long before I did, but I often wonder if he changed his ways. I would have liked to meet him again and find out; he put a profile on Facebook at one stage, but he didn’t respond to any contact.

Apart from two or three girlfriends at school I then had none at all till I was 20, as I was very shy and half-scared of females. My school sex education, by a bachelor religious education master, had a lot to do with that. He explained to us at great length what innocent, sensitive creatures women were, who needed repeated amounts of wooing and attention lavished on them to bring them around to the right frame of mind. Consequently it came as a big shock to me when I discovered they were almost as dirty-minded as us boys, and easily aroused too, quite the opposite of what I had been led to believe.

So I fulfilled my sexual curiosity and needs with frequent visits to London strip joints and hanging around in public conveniences where I read all the writing on the walls and exchanged “Age? Likes?” notes under the cubicle partitions on bits of toilet paper. During this time I experimented with putting on women's panties like my friend used to, encouraged by the drawings that were also on the walls, and I found that I felt so sexy in them. Just pulling a pair up around my cock would give me an instant hard-on, and I was soon addicted to it.

Then things changed, I started to attract girls like a magnet, but unfortunately the majority of these were “nice” girls who at the very most would only let you feel their breasts and stop you going any further. Until I met my future wife, that is. Very enthusiastic, she was just what I had been missing, and she was quite adventurous, too: for example we used to go to a local beauty spot of an evening and have sex in the grass with men watching, which turned her on enormously, but in later years although we often had sex on beaches, she declined to try car park dogging. Overall, though, she was far too passive, I always had to do all the work, while she disliked giving oral and was useless at doing a hand job. To give her her due, though, she enjoyed bum play, the signal was when I was fingering her, when she’d breathe “use both hands”, but we never got around to anal sex. As time passed, our sex life became rather patchy, with one or both of us too tired from work, or the kids were in the way. Now for many years it has stopped altogether, she has totally lost interest. I daren’t even touch her, she will freeze and push me away.

But during my years of marriage, I became more of a secret lingerie wearer. The more I had sex with a woman, the more I wanted to experience being a feminine plaything getting horny in sexy undies. A canvas bag hidden behind the driving seat of my work van contained lots of little nylon panties and some suspender belts, stockings, bras and slips, all organised in plastic bags, while at one stage I had strappy heeled sandals, a stretch micro mini skirt and a semi-transparent pink-and-black top that slid off the shoulders, bought from a charity shop. I was on the road for nearly 30 years as a skilled technician for a large company, and I didn’t work fixed hours, so I had plenty of opportunities to dress in car parks and toilets, where I enjoyed being wanked off by strangers, or I’d visit Soho sex cinemas, and later Fantasy Video in Islington, with the undies under my street clothes and enjoy shared masturbation. I didn't do anal then, though, either way. In the evenings I’d say I was going out for a pint, instead I’d go to a car park where I’d undress and put on suspenders, stockings, panties and bra under my trousers and top, then I’d drive to a dark cottage where I’d remove my street clothes in a cubicle and stand there with the door not quite pushed to, when it wouldn’t be long before someone came in and wanked me off. There were also solo trips to Paris, Barcelona and the Canaries when I packed undies in my suitcase and had fun dressed in adult cinemas and video booths. Most Paris sex shops had a device on the booth doors so they could tell if you hadn’t closed it, and your video would stop, but I found one place where I could safely leave it ajar while I sat in a leatherette chair wearing undies and waiting for company. It was also during this period that someone, a CD in fact, told me about dogging. As I know my way around I found the place he told me about with no trouble, and I was immediately successful, From then on I spent a lot of time driving to car parks looking for shows from couples.

My job involved working in women’s homes, where I’d find lost bits of their underwear behind furniture and appliances, and I became adept at pocketing them unnoticed. I would even put them through the washing machine at home if they were too dusty. The panties in particular would make me so horny, especially as I had met their previous wearers, so after my lunchtime sandwich in a woodland car park I would go into the rhododendrons, strip right off and try them on, together with some of my other items. At one car park there was an old fellow who used to look out for me, he would follow me and give me a really nice wank to completion while I stood there dressed in nothing but lingerie.

The thought of my cock in a pair of delicate little nylon panties designed for a female pussy was, and still is, a huge turn on. After I had watched women giving themselves in those porn films, or if I’d had a close look at a woman having sex in a car and. if I was lucky, getting a feel of her, I would have an overwhelming urge to be like that woman, wearing flimsy feminine underwear, pleasuring her man and being used in return. Then I just couldn't wait to get a pair of panties on, so I would drive to a car park, strip naked, put on full lingerie and suck off any man who got his dick out at my car door while I wanked myself in the panties. I love the feeling of the head of a cock in my mouth, and I like having a man very, very gently fucking my mouth till he cums in it like it's his wife's wet hole. I don't like fumbling through trouser flies, I like plenty of bare flesh that I can clasp my hands around while I am sucking him. I will gladly do it to another man in panties too, but I will stress that without lingerie involved ordinary male-to-male sex does nothing for me.

Now, the important bit: Contrary to what might be expected, these activities gave a huge boost to my marital sex life. I would go home and get into bed so aroused that I just had to have sex, although if I was doing it doggy style I’d imagine I was fucking a man who was wearing lingerie. But only a couple of days after that I would long to be in undies again and have some more cock, and so the cycle continued, each one stimulating the other.

The second point is, as I said earlier, there has been absolutely no sex whatsoever at home for many years now, so the above activities have become the substitute – but there is one very big change. While females remain my first preference, I am in no doubt about that, with dogging, nude beaches and adult cinemas my only hope, the difference is that instead of dressing up myself I now crave a man dressed up, with his erect cock bulging in sexy panties, ideally with stockings and other items of lingerie, and not me being the dressed one. I very occasionally put things on like I used to, but it is my last choice, one that I finish the evening off with when the first two are not achieved, which is all too often, sadly.

In more recent years I used to play with a silicone probe and KY jelly, when I’d kneel on the bed with panties pulled down just a little and position myself so I could see what I was doing in the mirror, that was such a thrill. Now in my twilight years, I regret that I didn’t make more of it. I wish I had dressed more often, found some clubs to go to (not easy in pre-internet days), had some group sessions with other dressers, sucked more cocks, and I’d like to have been fucked. While my marital sex life lasted, it would truly have been the best of both worlds.

Published 
Written by Oldbidogger

Get Free access to these great features

  • Create your own custom Profile
  • Match with Swingers near you
  • Arrange Meets with hot Swingers
  • Discover adult parties in your area
  • Chat with like minded people
  • Browse our real amateur Swingers gallery

Comments