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Crossdressing Stories

crossdressing

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...

Open To Offers

How I would like a outdoor meeting to go

Hi all, I hope that this out-line of a story/fantasy is not out of order here. Well over the last couple of weeks, I have been reading all the 'Crossdressing' stories (Yes all 70 pages. But I was mostly interested in the Outdoor/Wooded area and Adult Cinema ones) on here. To give me some inspiration has how to write this encounter. It was when I came across a story which told me of a 'Dogging site' at a wooded area (Noman...

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 the bottom as I went past her. She even complemented me if I did something right saying I was a good girl. You’re now thinking how I felt about all this. Well, the truth is...

My Sister’s Ex Pt1 - My Favourite Blue Dress

My sister’s bully ex notices me dressed and I can't resist

My name is Sophia and I’m a twenty-one-year-old sissy girl who loves to dress femme all the time. Over the past few years, I have got more and more daring with my feminine side, going out in public dressed. It was on one of those adventures I discovered a nightclub in town that was a hotspot for the LGBTQ+ community. I would often go there fully dressed and make new friends, drink, dance and have some fun. It was on one o...

Always the bridesmaid

A change to dress up at a wedding goes slightly wrong

My wife, Hannah, and I drove from the North West to Reading for a wedding. My wife was going to be one of three bridesmaids for her best friend Claire. The wedding was on Saturday but we got down to the Motel, a coach house on London Road, mid-Friday. Having sorted our room and cases out, Hannah announced that she needed to take her bridesmaid dress and accessories to a room that had been booked especially as a dressing r...

Adventures of a married man 2

Gay Bi sexual adventures

I am writing my adventures in no chronological order, just memories coming back to me, I have written before about my wife having her fling with a young colleague from her work which still turns us on when fucking, I am still reluctant to tell her my escapades as unsure how she will take the news lol! Soooo, sorry, zzz My story starts when she was away at her sisters a few years ago, I felt horny and fancied some cock in...

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...

Christine63

My partner introduces me to cuckolding

An evening with Ann's friends opens my eyes to the pleasure of cuckolding

I always told myself that the last gang bang would be my last now that I'd been claimed by Ann my future wife who also was my mistress so I was in heaven. By now things had quietened down and for a while Ann had me all to herself, our sex life was amazing, she being the dominant partner she'd really put me through my paces and if satisfied I'd be allowed to fuck her, she liked me her sissy slut and I really enjoyed being...

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Anonymous

8 into 1 dies go

Steven invites me to meet his friends with a surprising outcome

Part 6 After another explosive meeting with Paul,the man who had expertly made me cum hard at a previous party, 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 t...

Crossdressing Journey - Tentative Steps

The first taste of fun, whilst wearing nylons

After indulging my fantasies of nylons, lingerie and heels on my own for some time, I decided to be brave and see if I could be ‘used’ whilst dressed in my girly clothes. I’m not a convincing CD, so I wasn’t going to hit the streets looking for attention, so I decided to see what happened on one of my business trips, which seems to be a standard approach for discreet crossdressers. As I travel for work, I will often bring...

Anonymous

Totally dominated

My friend invited his dominant friend round and it changed my life forever.

Part 3 After that momentous and memorable night, my friend and I met up often for him to continue to use me as his submissive sissy for his and now my pleasure. My girlfriend had now moved away to university so I had ample time to be Christine which my friend took full advantage of. I got a text Thursday dinner time from my friend telling me to expect a surprise when we met on our now regular weekend meeting . Intrigued ,...

This is not a raunchy story. I just wanted to share my journey to crossdressing and, once shared, it may encourage me to share some other stories relating to my obsession with nylons. I’ve always been into nylons and high heeled shoes or knee high boots since I was a child. Never having a sister meant I only got access to tights and stockings once I started dating girls in my teens. I’d always loved the look of nylons on...

On holiday down south

Crossdresser taken

I was on my own having a day pottering around a seaside resort and noticed a toilet in the car park, the thought of having an accidental meet crossed my mind as I was wearing a green and white gingham bra and matching panties with black hold-ups under my jeans and sweat shirt. I slowly walked towards them with my fem dick feeling as if it was coming to life. Walking in round the corner it was a metal long urinal with one...

An Unexpected Guest

Another Fantasy of Mine

I'm wearing my polka dot dress, stockings, suspenders, boots. Tidying the house and general day to day stuff. I hear a knock at the door, so go to answer it. The man at the door is broad shouldered, maybe 6ft, jeans, long coat to his knees, looking down (as you do), I see his meaty cock already out and proud, leaking precum and hidden by his coat. He pushes passed me and walks in. Closing the door, I turn and face him. He...

Anonymous

The leaving party

What should have been a night out with my friend turned into my first gang bang

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 liked . 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 m...