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Crossdresser Stories

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Anonymous

Friends leaving party

My friends leaving party turns out to be a party indeed

Part 4 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 r...

Anonymous

My introduction to anal

An unplanned stay over turns into a night of discovery

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 tim...

Anonymous

Sissyfication by my friend

My friend makes me his submissive slut

Part 2 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...

Anonymous

Stay over turns into fun night

The night I accidentally inseminated my friend

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 tim...

Anonymous

The night things changed

My friend turned the tables and I ended up a sissy slut

After that unexpected night with my friend, and what we did, I tried to process it all in my mind. 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, m...

Anonymous

8 into 1 does go

Steven arranges a gang bang party for me with a surprising ending

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 mor...

Anonymous

Stevens friend takes me in hand

Stevens friend wanted to see if he could replicate his handiwork

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 of...

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Anonymous

1st threesome

My friend invites a dominant friend

After that momentous and memorable night, my friend and I met up for a session of me being sissified for his, and now my, pleasure on a regular basis. By now my then girlfriend had moved away to university so I had ample free time to be Christine and made...

Anonymous

You're the Wife Now!

A message from an older house wife who wanted me to be her replacement in more ways than one...

This is not a story as such. It is a message request I received from a lady from this site who is part of a couple. Ever since I received it, it has become my biggest fantasy. I had been on a different swinging website for a few months and found the exper...

slim crossdresser fucked by group

big cocks fuck cross dresser pussy

After a busy few days working London it came to Thursday evening and was due to go home the next day. I had brought with me some white lingerie, short dress, bra and sexy underwear and had booked a hotel close to a local TV friendly. So showered and dress...

Meeting Tanyas other Secret

Meeting my lovers secret lover

Tanya opened the door dressed in a white short cropped top, with a 60's rockabily skirt on with tan stockings and black high heeled shoes. Her red lipstick looked lush and inviting as she smiled a heavenly wide smile at me. 'Hello my darling girl' She sai...

Unexpected friendship

Where I would love my cross dressing to take me

First of all, I am a long time crossdresser who has had a number of meetings with men but always been left feeling there should be more. I am married and my wife knows and approves of my dressing and meeting. We used to be a cuckold couple, with me as the...