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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.

Popular Stories

My Sister’s Ex 2 - Becoming His Slut

Submitting to my sister’s bully ex as things escalate to new desires.

It was four days since I deepthroated Rich to a huge orgasm in the living room of my sister’s house. I wasn’t sure if he would keep to his word and keep my true identity intact but I thought that if he was intending to expose me it would have happened by...

All Stories

I've been dressing since my early teens so I've had lots of " adventures". Lots of them in the early days we're in the local public toilets . It was there as a skinny young man dressed in stockings and suspenders that I discovered my love of pleasing men...

I mentioned before, that i inherited a Mercedes van, It seemsd a waste to have it parked on the drive so i cleaned it out and installed a matress and cushions in the back, Well the bank holiday dawned unusually sunny , with nice warm evenings, Five oclock...

Amanda and Stuart 2

Amanda and Stuart wanted a rematch, this time they brought the ultimate male with them

It would be just over a fortnight before I heard from stuart and Amanda asking how I was, The next sentence was a little more of an eye-opener as they Initially came over as newbies, especially Stuart but I was beginning to sense they were something more...

Sissy Boy Wimp pt3

Another surprise for me !

After Mark had left and both myself and my wife had recovered, we had a full discussion about what had happened to both of us. She asked if I liked what had happened to me up to now and I had to confess that I had enjoyed it. This must have pleased my wif...

End game

Steven takes me dogging with disastrous consequences

The last 12 months had been anything but smooth! , my wife actually leaving me for Kev , I didn't expect that at all considering all we've been through, Gary and Steven, then splitting up, Steven then taking care of me . He was in the right place at the r...

Sissy Boy Wimp pt2

My wife expands my feminism

My wife encouraged my feminisation more over the next couple of weeks. She often had me dressed more girlie whenever we were alone at home. I even had to wear a bra while I was dressed and she took great delight in fondling my breasts and patting me on th...

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A Vantastic time

Free delivery ,

I woke up and looked at The blue Mercedes van parked on my drive, My grandson had told me he was leaving it, "I have a works van now so I won't need the Mercedes, I shall get rid of it eventually but use it when you want,", "Right, Thanks a bundle i thoug...

Turn on

My kind of man

Ive been dressing now for over 50 years . Well before the internet. Which meant meeting in public toilets . Thankfully there was quite a few.of them around . I dressed at home but my first few times in the toilets I wasnt dressed. Then I saw the drawings...


Steven and I become lovers, however a meeting with friends was about to change all that with a surprise revelation from one of them.

The first few months after we went our separate ways was, for me, the most difficult. I'd lost my confidence, my ED raised its ugly head, then the sale of the house fell through so we were still financially connected as we rented it out with at least a st...

girly boy

life as a crossdresser

As a child their were 4 of us in my family me, the baby my 2 older sisters and our young mum . my sisters were always dressing me up and to be honest i didn't mind and as i started secondary school they lost interest playing with me and i forgot about it...

Sissy Boy Wimp

My wife made me do it !

My marriage has been a long suffering affair. I’m not the most forceful or demonstrative of men and my wife had often chided me for it. We more or less did what she decided what we were doing and of course our sex life was included in that. Its not that I...

Hi all managed to get a meet organised last week with a sexy mature shaved 68 year old guy , firstly we exchanged numbers txting each other about what we like to do things he wants me dressed in etc , he loved kissing which is a must for me such a turn on...

Over my long life i have loved the life of a Transvestite, It has never just been about the clothes, unlike many crossdressers ,i have all a woman yearnings, The longing to be held close and loved, to be kissed and fondled, It was by choice that i chose a...