My Crossdressing Story / page: 285 - Erotic story Collection

My Cross-dressing Story

All 100% true.


I was about 13 when I was home alone during the day, I went into my (older) sister’s bedroom and saw her school dress on the floor. For some reason, I thought I would try it on, so I undressed, put it on, and paraded in front of the mirror (no underwear). My immature little penis got stiff, but I had yet to discover the delights of ejaculation.

I walked around upstairs for about 30 minutes, then took it off and put my boy clothes back on.

The next year we moved house, and I started to get an interest in the laundry basket! Every bath time, I would have a look through and discovered my mother’s nylon full slips. I still hadn’t discovered what my right hand was for, so just got stiff which was nice.

It was around this time that one of my (male) friends and I started to ‘play’ - just undressing each other and groping each others cock. One day he suggested I wear one of his mum’s old bras, I did, it was nice! He tried it on as well. We continued to play in this way, then one evening he came to stay over while my folks were away. We looked through my sister’s things (she was away at college), and found a nice blue full slip, and a lovely baby-doll, very sheer and tiny sheer panties. We undressed each other, then he put the slip on, and I put the baby-doll on. As I pulled the panties up, I all of a sudden ejaculated. We both thought this was funny, but didn’t do anything more.

I then discovered girls, and my dressing reduced (but didn’t stop). When I finished college I moved away from home, sharing a flat with a friend from college. I had a good stash of porn, including some tranny mags. On the return from one of my trips home, I walked into a Dorothy Perkins shop. I came out with my first items – a white lacy front fastening bra, matching tie-sided panties, and a long waist slip (floor length). I got back to the flat, and dressed in my own things for the first time – heaven! I can’t remember how many times I came that night, but it was great!

I then bought a house, had much more privacy so my collection increased. Several slips (full and waist), several bra/panty sets, a couple of suspender belts, stockings, a basque, a short nightie and a long nightie (both with negligees). This was way before digital cameras, but I processed my own B&W films, so had a few pics.

Girls came and went, but then I met ‘the one’. We were married just over a year later and I got rid of my collection (and the pics). I stopped dressing – or so I thought. I was travelling around the country a fair bit, and started wandering into stores when away and looking at the lingerie, then bought a few items. I had a small collection that I kept in my car for nights away.

Trips to the US were fun, I would always got to a J C Penney or similar and buy a slip, bra and panties to keep me happy away from home.

Towards the end of this time, digital cameras cam out, and I found I could use mine as a web-cam. I had my first cam 2 cam session, came 4 or 5 times during the night while playing with like-minded others.

The sexual side of the relations hip with my wife was on the wane, so masturbation was my primary relief. She threw out some of the undies I had bought for her (2 white teddies), and also a lovely Kayser full slip. I managed to acquire these before they reached the rubbish and still have them.

There were many changes at work and I ended up home based. I had quite a few conference calls with customers were I was wearing just the Kayser slip!
I gradually added to my collection, and started to dress more and more. My wife retired, and this put a stop to things.

Now, in retirement, I can only wear when she is out for long enough, but I do like to cam with others.

I consider myself straight, and wouldn’t do anything without lingerie (or at least nice man undies), but I do get aroused by a hard cock in lingerie, and I have made quite a few guys cum just by dressing on cam for them. I have no wish to be a ‘gurl’, I’m just a hairy guy that like lingerie (on women as well).

How long will I continue? As long as it still feels good!!!

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