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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.

Trending 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 now. I also had the photo of me holding Rich’s cock in my hand as insurance should he ever threaten to expose me in the future. I told myself I’ll never be in that positi...

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A twist of Lemon

An early morning dream, pieced together.

So this morning I woke from a dream horny and hard but at the same time confused and feeling a bit vulnerable. I shall attempt to piece it together. Rewind 20 years to when things were going south between me and my ex. She was working as a barmaid at the Flowerpot in Derby. We’d had a discussion about her being allowed to snog guys at work if she felt like it and not being a jealous guy I was ok with that. Then it progres...

Meeting David again

David likes to make me his gurl

If you’ve read previous instalments, you’d have seen that I met David at a toilet block and then followed up by messaging him to arrange a further meet. This is the story from the third time I met him. A few days after our session in the car park of a picnic area, well-known to the dogging community, David messaged me saying, ‘Well, Joanna, you performed well as my slut, so I’d like to see you again and teach you more. Ar...

A Cottage by the river,

how it all began,

I am Cathy, A mature transvestite from Cambridge, I have shared several of my Currant experiences of cruising on htis site, This time i would like to go back in time to explain how i reached this stage, I am sure i was born homosexual , many are and manage to surpress their feelings , Mine were recognised from an early age and instread suppression i was encouraged to nurture these feelings, pretty clothes were given as pr...

As I'm getting older it's becoming more difficult to have fun so I have to grab the chance whenever I can . Obviously to fill in the times I can always rely on the people on here x. I'm now retired but still love to dress . Unfortunately my wife has also retired so I have to make the most of the times that she's visiting friends. One of those times happened last week. She was off to Norfolk for a few days which gave me ti...

My first time Pt6

News of my unusual ejaculation spreads amongst Stevens friends ending in another party invite with a surprise ending for me

After that explosive meeting with Paul, I was lost within myself, reliving that moment in my head where he made me shoot my spunk literally everywhere , I tried edging myself but never came close to how Paul had expertly wanked me off, I knew I wanted more and it was becoming increasingly clear I was a sissy slut that needed sex as a submissive, not that person who accidentally inseminated his friend that first time a few...

My name is Cathy, I am a mature transvestite from Cambridge, I have Written several times of my experiences cruising around the Cambridge area,, I consider myself having a healthy appertite towards sex as i regularly cruise two evenings a week, I still live with my wife and although my situation is accepted i am not permitted to bring men back to the house, My ford car was a regular sight in the dark laybys and the local...

The loneliness of a long distance lorry driver. Part 6. After hitching up a trailer full of provisions, my destination was Scotland, Inverness actually. We were in for a long drive with at least 3 stops. The first being on the M25 South Mmmm’s. Then the A1M north. Rest up at Penrith, Next planned stop Scots corner. I knew Scot’s corner well from driving smaller vehicles. I had been propositioned here several times, also I...

Part 5. I woke next morning, Maxine was still snuggled up close my hand still cupping a breast. The only difference was I was now pushing back as I was very erect. Maxine felt me press against her, she lifted her leg to allow me to push against her tight pink ring. “Breed me lover, I need you and want you, fill me darling.” Maxine panted as she pushed back. I slid inside her not fully, our angle of making love prevented f...

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The loneliness of a long distance lorry driver Part 4. It was a 10 minutes walk to my flat, from the service garage. Maxine had her rucksack that was bulging my pull along case was struggling to contain the rest. Back at my flat I showed her round. We unpacked our lingerie first for a quick wash. The skirts, blouses etc for a longer wash. “Is it ok for me to shower?” Maxine asked. “Yes of course it is, towels in the cupbo...

The loneliness of a LDLD. Part 3: I made us both a cup of tea, not the best but it was hot and wet. We struggled to shower together as space was tight. It did make for fun. Now we were both hot and wet. We dried each other which almost ended in returning to the bed, then we have to shower again. I clipped my bra in place in inserted my boobs. Watching Maxine put her bra on and settle her boobs in the cups. My next item I...

The loneliness of a LDLD. Part 2: We made good going across the island and the bridge. Back on the mainland and heading for our next destination. My phone pinged in its cradle. “Do you want me to read that?” Maxine asked from the centre seat. She had moved towards me to be able to caress my stocking tops and suspender straps. I in turn was able to keep her semi aroused in her panties, she had changed yesterday’s to a love...

My first time Pt5

Paul invites me round for a one on one experience I'll never forget

So, my first gang bang behind me and my friend now down in London I was really at a loose end, Steven kept in touch via text messaging but no physical meets which I really needed, then out of the blue I got a call from the guy who so expertly wanked me off that night asking how I was and the possibility of me going round to his for some fun, apparently he had asked Steven for my number as he was still impressed at how he'...

My first time Pt4

Steven introduces me into the world of group sex

It had been several weeks since I'd been expertly fucked by Steven, my friend and I kept up our regular meetings although I desperately wanted another night with him, especially after what he did to me, and remembering how dominant he was which I really enjoyed . Then the golden opportunity presented itself. My friend had got a job in London and a leaving party was organised, he told me Steven would be there, for a moment...

The loneliness of a long distance lorry driver

Carole picks up a hitchhiker with amazing coincidence

The loneliest of a LDLD. (Long distance lorry driver) Part 1 While some of the highway regulations that are applied to LDLD’s, might not be fact. I have tried to research some them. Meanwhile this is fictional erotica not about driving articulated lorries around the UK. I would add driving in Europe, but there are to many accidents, probably because they drive on the wrong side of the road. Europeans say they are not on t...

Fucked in Morley

Fucked Hard

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 arranged. He lived in Morley near Leeds and lived alone. He had shown me some pics that a cockold husband had taken of him whilst banging his wife. She looked well pleased as...