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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.

Very horny

Very erotic

This happened a few months ago I started seeing this woman from down the country we been together for About 2 years but I never went to her home place down the country call it Meath we both live and work in Dublin we have a great sex Life she 40 I’m 50. She brought me down to her cousins wedding we arrived on the fri evening met her folks her sisters everything was going well she told me her young brother was coming from...

The Tourist

An interesting afternoon

It started with a posting on Craigslist “ married American male tourist in nice hotel seeks similar for fun times “... I replied - “hi there, sounds like you’re horny ... could you tell me more?” ... to be told “ 5’10, well built , hung , dominant , wife and children gone back to States and I’ve two days to play “ .... I asked what hotel and it was a four star in Temple Bar .. so far so good ..” I like to dress if that’s...

Hi all. I'm not even sure why I'm writing this. I think I'm bored or it might be somewhat freeing or some nonsense like that.I'm a secret crossdresser. Only one other person knows this...........and had a lot of fun with it. This is no more. I started out very differently. I had an ex-girlfriend who constantly made me wear her g-strings while having sex. It was awkward at first but I would have done anything for her. She...

Discovery of Exhibitionism

watched while cross dressed

By the time I was around 18 I was crossdressing almost all the time I could , I had progressed to makeup and even a couple of wigs, my wardrobe had increased in size 10 fold and mum's things were nearly safe from use apart from the odd suspender belt or bra , she too had become more relaxed and accepting that her son had not turned into the manly he man but more of a feminine stockings wearing get down on your knees for a...

The Chronicles of Alex

young guy discovers his feminine sexual side

As College had finished and early summer arrived Alex spent most of his day lounging around the house and garden whilst Mum was away at work , a very successful business woman also very independent and sexy , Alex's father had passed away when he was a very small child so it was just him and Mum . A few weeks after his 18th birthday Alex had met Julia a very interesting and a bit weird also she was a bit Goth'y and wore l...

John D

Friend in a new light 3

Fucked my friend

Me and Jeff have been at it like rabbits for few weeks now recently we were at a friend's wedding I asked him to ask Laura could he wear her panties under his suit thinking it was for her benefit she said of course. When we were drinking later on our own Jeff said Laura was horny at thought of him wearing her panties that she gave him a blowjob on the way to hotel as he drove. He came in her mouth and said when she kissed...

John D

Friend in a new light 2

Fucked my friend

After we had something to eat and had cooled down we both had a shower we shared it and played a bit in there too my first time sucking cock was probably helped by it being so clean Jeff sucked me to and rimmed me as well which was weirdly sexy tbh. When we were finished he said give me 2 mins in the bedroom to get ready he called me and when I came out he still had the wig on even in the shower because I told him I'm not...

John D

Friend in a new light

Fucked my friend

Hi I am a straight male who is in a happy relationship I do watch a lot of porn on my phone lately the usual stuff wasn't doing much for me. I started to look up cross dressers and femboy some of these vids are insanely hot. I have looked at gay porn but when I look at a man I don't feel anything sexual however this femboy/ CD stuff has me so horny. I jokingly mentioned it to my mate telling him this stuff is hot to watch...

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Well, I went to Hazelbank for a wee cruise and as usual, nothing going on. I then went to Shaws Bridge for a wee look and it was like wacky races with people flying round from shaws to minnowburn to Malone House and back again. Anyhow, sat and waited and no one was interested, I decided, one more look at shaws, have a smoke then head home. There was a car parked and it looked like no one was in it, so I got out and fixed...

As i pull my panties up and get ready he texts me asking me to keep the door open and tell him what room i am in i text him back to tell him the 2nd room and ask what time will he be here. 5 mins was his text. I quickly pull the tights up my soft shaved legs which he loves put my make up on and wig and the sexy secretary look is complete. I hear him come in down stairs and close the front door.I am sitting on a bed with o...