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Cross Dressing Stories

Crossdressing, usually more common for men, is an interest that explores self-expression by wearing clothes from the opposite gender.

Often the clothes chosen will either belong to a spouse or a partner which unlocks a door for new erotic pleasures. Adapting the comfort of clothes that aren't normally worn can be an activity that takes place behind closed doors or be an exhilarating experience outside as well. Wearing a dress, high heeled shoes, feeling pleasure from wearing lace and satin, and choosing the name of the opposite gender, are all traits associated with cross dressing.

Have you become a crossdresser or are sexually attracted to crossdressing? Share your exciting discoveries by writing your own erotic encounter below.

Lingerie Lover part 2

What happened next

I left you when I tried to put Ellies moms things back to when I started wearing them, I didn't see them for a couple of weeks, but two weeks later Ellie came home for the weekend, I saw her mom when I picked her up, she didn't say anything but I think I...

Lingerie Lover part 1

How I started a life long affair with lingerie

I have loved lingerie as long as I can remember, I grew up with five sisters and a very attractive mom, this was in the 60's slips and stockings were everywhere especially in our house. But the story really got interesting when I met a lovely girl while o...

Sex on a pension

George cums too

Jenny was on Holiday and as promised i had called round to check on her Grandfather, Cyril was quite well when i called but before i left he complained of a rash in his groin, When he removed his trousers for me to apply the savlon i was faced with an ere...

I live very close to a country park. It has 4 carparks . 3 of them are very open plan and used well . The 4th one is more secluded and the road into it is pot holed so it doesn't get used much . Obviously this is the one to use for fun ! As usual I cleane...

Been a lover of womens clothes all my life. Love the sexy lingerie and the high heels. Tottering about and posing with legs showing off tight muscles. My first encounters were with men although I liked girls it was the pure sexual thrill of handling a big...

Starting Out Part 4

First Blowjob

This is the final part of my starter journey into crossdressing. I have always had a slight and slender frame, never carried much weight so I always looked good in lingerie and short tight skirts. I was a soft featured youth and looked like a tomboy girl....

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We were meeting a couple of times each week at his house for some fun and frolics. The idea of me getting dressed up and handling cock was great. I knew it wouldn’t go on forever but it was going good. He was trying to get me to blow him but I wasn’t too...

Starting out Part 2

Got me in his room

Well, after we had that encounter in the park, the next day when reality at what we had done set in I wondered how it would affect us as mates etc. We all turned up at the same hangouts we normally did. We cracked on as though nothing had happened and I t...

Start of the journey

When I realised I liked cock.

How did I get into dressing up? It couldn’t have helped being bossed about by two older sisters who used to dress me up in girls clothes and call me Doris. I wasn’t keen on this but guess what? It grew on me. I was always getting hit upon by men when I wa...

Big Rough Fuck

Hard cock stuffed in me.

About 3 years ago I was in conversation with a guy who wanted to fuck a crossdresser. Music to my ears. We arranged a meet and about 2 days later I went to his place for a session. He was a big lad with a bit of a belly on him. Didn’t look that great but...

Training course

I’m sent to the Lake District for a week

Training session. I had new employment, but it meant going on several training sessions away from home. Leaving my flat empty. My neighbour took in my mail. I had no pets or anyone to consider. Monday morning I climbed on board my first train heading to W...

Fucked in Leeds

Got banged good in LBD

Well I had been chatting to a guy who said he was into crossdressers and the chat was horny and I thought I must go and see if he is the real thing. I was living away from the Leeds area and was back for a bit of family business and so a meeting was arran...