Crossdressers In The Park Sex Stories Stories

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Craigslist CD Hookup

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I have been crossdressing since I was a kid. I started out with a pair of my mother's pantyhose, as most other crossdressers start out the same way. Once you get bit by the bug, you're hooked. This is my first story, but I have so much to tell that this certainly won't be my last. All of what I tell you here will be 100% true. I will not dramatize or sensati...

Want Some Dick

by Marlene on Sep 11, 2017
Transsexuals & Crossdressers

Sometimes I get so hot and horned up that I have to have some cock sex. As most of you who read my stuff know I like it both ways but sometimes the thought of having a big cock in my mouth or in my asspussy is so irresistible that I have to act on it. I have to make it happen. There’s a park that I know about. Guys go there looking for sex. I assume some ge...

Mia More

by seams_straight2me on Sep 16, 2017
Transsexuals & Crossdressers

It was 5 days after my very close encounter with Mia. I was still on very high spirit after meeting her, and fucking her. I could think of nothing else. We kept in touch via text messages and phone calls. She was "on location" for some photo shoot. One less about fashion and more about horny transsexuals having very sexy fun. She sent me a few pictures of...

Interactive Crossdresser...Dare Me Ch. 02

by PorscheKaru on Sep 16, 2017
Transsexuals & Crossdressers

Hi Porsche I loved your kinky stories and I think its hot how you let strangers tell you what to do. I would like to hear you do something more humiliating though... Are you ready? I dare you... to dress as a hot woman, very high heels, fishnets, tits on, makeup, but with a very short mini skirt and no panties. I want you to get a dog collar and a lead...

The Hitchhiker

by hydrangealawrence on Oct 8, 2019
Transgender & Crossdressers

I shade my eyes and scan the road. It's been at least half an hour since the last car. The heat radiates off the asphalt. I lick my parched lips. I'm almost out of water. I spot a vehicle approaching through the shimmer. I jut my hip, stick out my thumb, and hope. A rusted Ford pickup rolls to a stop in front of me. A man in tinted aviators and a sleeveles...

Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

Third Stop in a Lifetime of Travel

by dadavox on Jul 15, 2020
Transgender & Crossdressers

Hello, great people! More sexy stuff coming your way. Hope you guys are enjoying the stories. Blessings! - - - - - - - - - - - - - - - - - The second day I woke up around 8 am, feeling wonderful. I had a gorgeous woman lying on my chest, we were staying in a beautiful beach town in Mexico, and our vacations were just staring. What a lucky bastard! Ka...

Cabin in the Woods

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

Finally, I get to give you another TRUE story after a WAY too long 'dry spell'. This story is completely true (and may be a little boring maybe...would love any feedback). Only the names have been changed to blah blah blah... Anyone who is familiar with my writings knows my stories are true and not made up unless I openly state at the beginning that it's a...

Jamie the Gloryhole Slut Ch. 02

by jr0777 on Sep 16, 2017
Transsexuals & Crossdressers

Hi guys, I got a lot of positive feedback on my last story, part 1 of Jamie The Gloryhole Slut. Thank you everyone for the encouragement. With that encouragement in mind, I give you my second story about slutty Jamie. I hope very much that you enjoy it and it turns you on -- it does for me. Love, Jamie * It was a typical weeknight dinner meeting with cli...

Skype Disaster Pt. 06: Cum Together

by GeorgiaD on Oct 8, 2018
Transgender & Crossdressers Stories

(Catch up: After having dressed in an uncharacteristically slutty way, whilst preparing to watch some tranny porn, and perhaps appear on webcam, Georgia's preparations had been interrupted by Tim, who had previously cancelled his date with her that night. Tim's reaction to Georgia's appearance was, not surprisingly, one of quickly growing sexual interest.......