Crossdressing

Sissy Theater Part III

Posted by: Sissytrap Age: 35 Posted on: 28 Jan 2025 5 comments
4 likes 18 views Category: Crossdressing Tags: Sissy, crossdresser, gangbang, submissive, chastity belt, ass to mouth, anal fingering

As we ended part 2, I was in a tiny pink chastity cage, and was in the passenger's seat of the taxi, leaning over Alex's lap, taking his cock into my mouth as deep as I could, while he spanked me and fingered my ass...

After a few minutes of sucking, Alex pulled me up by my hair, telling me he didn'... » Read more
Another Experiment

Posted by: MiabUK Age: 50 Posted on: 10 Jan 2025 7 comments
7 likes 13 views Category: Crossdressing Tags: crossdressing, wanking crossdresser, cum in knickers, sucking shemale cock, married crossdresser, trans cum

My first time playing with a cross-dresser.

Always wanting to try new things, I started to wonder what sex with a cross-dresser might be like. As usual there’s only one way to find out. Contacting a number via a swingers site I am on, I eventually found amongst the usual timewasters someon... » Read more
Sissy Theater Part II

Posted by: Sissytrap Age: 35 Posted on: 21 Oct 2024 7 comments
3 likes 39 views Category: Crossdressing Tags: Sissy, crossdresser, gangbang, zesty

Part 2 of Sissy Theater. To sum up, at the end of part one, I was in the cab, I had promised myself to the driver for at least the night, and as my costume for the play dictated, was wearing a short green frock dress with green thigh highs, a little green thong, and at the point where I ended part one, had placed a ...
Part of the fun for me, as kind of a new sissy, was being paraded around the sex shop and then the gas station to get ice, in my little outfit. He kept on making me bend down to retrieve things, thereby exposing my bottom for everyone to see. I was dribbling cum from my cock, soaking the front of my little thong. The d... » Read more
Wearing Panties For The First Time On Cam

Posted by: BiCurious00 Age: 45 Posted on: 20 Oct 2024 10 comments
8 likes 39 views Category: Crossdressing Tags: male, solo, cam masturbation, panties on men, crossdressing fetish, group masturbation, zesty

The story of the first time I wore panties on camera with other men

During lockdown I started using online chat rooms, stroking along with other guys online. I've always enjoyed watching other men wanking whilst wearing women's panties, especially nice sexy ones with a bit of lace on ... » Read more
Sissy Theater Part I

Posted by: Sissytrap Age: 35 Posted on: 09 Oct 2024 8 comments
3 likes 34 views Category: Crossdressing Tags: Sissy, crossdresser, gangbang, chastity belt, zesty

Hooked up with a taxi driver taking me home from a play I was in at the local theater. I was dressed like a sissy at the time because of my costume, but he, and later that night, his roommate, were ready to go, and ready to fuck me like a girl. I had no idea at the time, but I was about to be dominated in very kinky...
A few years ago I was in a local play. I did not drive, so I had to get a ride home in a taxi. My costume was complex, and quite feminine. It made me feel sexy even though I'm technically male. Now, because of the things I had to do in the play, I needed to make certain adjustments. For instance, I was up on cables... » Read more
Dressing Up In Panties And Riding A Dildo And Feeling You Cumming In My Ass

Posted by: Pantydude Age: 57 Posted on: 10 Sep 2024 5 comments
4 likes 34 views Category: Crossdressing Tags: Panties, crossdressing, anal play, Watch my wife stroke other cocks, Sister

I want to dress up in sexy lingerie and make LOVE to a man who will respect me.

Another way I enjoy to get off is to dress up all sexy and get fucked by my "man"! Sometimes I get in one of my "I want a cock in my ass" moods. I am bisexual but only acted on that side once whi... » Read more
Trying To Understand

Posted by: Wetgirl2 Age: 24 Posted on: 09 Sep 2024 8 comments
7 likes 36 views Category: Crossdressing Tags: Cross dressing

I’m always up for helping others explore their sexual feelings and fantasies-whatever they may be. It became apparent that The Lovely Chris’s brother (and sole supplier of cock to me) has a panty fetish, but I wanted to find out in what way, what he might be hiding from me (for whatever reason) and where...
Panty smelling? Well yes, of course. I suspect most men/boys enjoy this, and why not? They enjoy our scent of their fingers and cocks, so why wouldn’t they enjoy smelling our panties too? I know I've always adored smelling other girls undies. But I sensed there was more something heartily d... » Read more
One Night On Fenchurch Street

Posted by: GalerioMano Age: 18 Posted on: 02 Sep 2024 3 comments
2 likes 31 views Category: Crossdressing Tags: Young, Trans, adventure, fiction, dark

A student in London is relaxing during the interval between his national exams and his first day in his chosen campus. The interval was meant to be relatively quiet, but Fate has other plans. This is the beginning of the downfall. This is part one.

It was a cold summer evening somewhere near Fenchurch Str... » Read more