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Crossdresser Stories

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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...

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...

My first time Pt3

This would be a defining moment in my life

After that memorable night where my friend unexpectedly dominated and sissified me, I wanted more.We now met on a regular basis and we're more daring with each other, well mainly him!. By now my then girlfriend had moved away to university so I had ample free time to be Christine and made the most of it dressed when at home, it felt so liberating and sensual. My friend knew this and made full use of my new sexual freedom....

My first bisexual experience continues

My friend was about to turn the tables on .me, I'm glad he did!

After that incredible night with my friend, I tried to process it all in my head. I wasn't gay? I had a girlfriend and enjoyed sex with her but also enjoyed what I did that night with my friend. For a couple of days I avoided my friend, mainly out of embarrassment but that didn't last long as he had sensed this and suggested we meet to clear the air so to speak down the local coffee shop. Invitation accepted I made my way...

My first bisexual experience

A chance stop over at my friend's lead to my first bisexual experience

Although this happened a long time ago I'll never forget my first experience so I'll write this as best as I can remember, I hope it invokes memories of your first experiences. This happened unexpectedly when after a night out on the town with my long time friend I crashed at his place. I'd sort of known for a while he might have gay feelings, I wasn't sure if he knew that I liked wearing women's clothes but I guess somet...

After the toilet block visits

I finally meet Mark again, the guy from my first visit to the toilet block

When I wrote about my first toilet block experience, I mentioned one of the guys that I met was called Mark. He was a respectful lover and had offered me his phone number before he left. I messaged him a few days later and immediately regretted it, thinking that I was just someone to ‘chalk off’ from a toilet encounter and that remorse would prevent him from wanting to be the same CD again. After a while, though, I did re...

Impromptu Fun

There’s a lot of fun on offer, if you look in the right places

I used to think it was really difficult to stumble on some fun when you're seeking action. I've read the stories about fun in toilets, but felt I must have only visited straight guy loos, as there was never any action. I was ready to give up on it when I decided one day to try something different and went out dressed with black holdups and a blue satin thong underneath my male clothes. I brought a backpack containing knee...

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Helpful Neighbour

My neighbour helps me so I help him too.

It was Friday morning and the first day of a fortnight's holiday from work. I woke with a very strong feminine urge and decided today was definitely a dress up day. I got up, had a bite to eat, and then ran myself a nice hot bubble bath. I added some rose petals and bergamot oil to the water and took a nice long soak. I then shaved myself from chin to toe, dried, and spent 20 minutes moisturising my skin - the smell was d...

The Old Man and the Sissy

The beginning of a Tv's journey

Some context first. I was born hypospadeas (look it up, easier than explaining). Reconstructive surgeries started from just after birth until my late teens, were extremely painful and traumatising. As such I was a late developer, physically. I was under 5ft until I was 16, under 5'3" until I was around 19, and had a very narrow waist...25in... and slim, almost hairless limbs and torso, until I was around 30. During my las...

Winning a Bet

When I was young and carefree

Regarding the picture of me nude under a leather coat wearing thighboots. About 15 years ago I used to teach (adult) nightclasses. One of the students was another mate who my partner and I had played with a few times, along with his wife. All of us bisexual. We had met for lunch and he asked me about the thighboots he knew I owned, the usual questions I suppose. At some point we made a bet that I could get from where the...

This story is a continuation of my previous story “ I Confess” My brief career in shop work ended in my early twenties in another town. Shop management was all glory and low pay. I took a job in a local factory with much better wages. I was also living Independently and for once l had money to spend. Some of which l intended to spend on cross dressing after l had seen it in imported ( and probably not legal at the time )...

First black cock I’m 47 and only had a little bi experience over the years . In the last few months I got chatting to an Indian guy hes 54 , vwe and very kinky . While chatting we got kinkier and I started to feel more and more slutty , wearing hold ups and panties under my clothes at a family get together . Knowing my dad was homophobic and a little racist this turned the horny Indians guy on We arranged to meet , even t...

Crossdressing Journey: Tentative Steps - The Next Evening

The climax of two fun nights in Bath with a fellow bi guy

This continues after the exploits of the morning before breakfast. I spent the day with a heightened level of arousal in anticipation of what might unfold tonight. I didn’t set any expectations, so that I wouldn’t be disappointed, and instead just thought about my lover’s cock. All I knew was that I was expected to wear my black high heeled over-the-knee boots and a short skirt or dress. I was more than happy to satisfy t...

Crossdressing Journey: Tentative Steps - The Next Day

Finally, the follow up to my encounter with a new friend in a hotel

The next morning I woke with a pleasing memory of the previous evening. The thoughts of being played with whilst dressed as a girl were amazing and now a new day had dawned with the promise of more adventure. I got up and showered and douched in case things advanced this evening. I hadn’t heard from him yet, but I thought I’d go to breakfast in nylons and another skimpy pair of panties under my male clothes. Just as I was...