Transsexuals & Crossdressers Stories

15,868 results
Orientation
Length
Source
Infinite Scroll

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

Her Dick's Bigger than Mine

by KittyAshleyy on Sep 28, 2020
Transgender & Crossdressers

I had been best friends with Chloe since I could remember. We were basically inseparable all through school and into our adult lives, even living in the same 2 bed apartment in our early 20s. I had known her so long that I knew her before she was Chloe, and while I had grown into what most would describe as a twink, she had grown into one of the most beautif...

Natalie has a New Reality

by natalieukcd on Sep 28, 2020
Transgender & Crossdressers

"Get dressed sissy and go home," Lewis ordered me. "But the key..." I said, as i got up, looking for my clothes. "I keep the key. You belong to me, sissy and I want you in that cage." "But... my wife... I need to remove it. She doesn't like it." I whispered. "I don't give a fuck about your wife. Besides, she won't be a problem," Lewis added. I stopped c...

Crossdresser Visits ABS

by iwant2suckabig1 on Oct 12, 2020
Transgender & Crossdressers

Thought I would post another one of my true adventures. Those of you who may have read my other adventures know that I enjoy dressing super slutty and being shocking in public. Nothing gets me more worked up than people watching me enjoy myself. With that in mind many of my adventures are dressing up and flashing my hard cock to people. While I enjoy both...

Two To Three Times Daily

by estories69 on Sep 19, 2017
Reviews & Essays

My name is Jason and here is my story. This is my first time writing in this manner so it probably won't come out the way I want it to. If that is the case, then I'm sorry. I'm a 22-year-old guy in college. This should be the time of my life. I'm living in the dorms, I'm away from my parents and I can do pretty much whatever I want. Well it isn't. I'm no...

Angel's BDSM Experience

by Angelscuck on Sep 19, 2017
BDSM

My wife enjoys having her bottom spanked. Not heavy pain but light to moderate. She told me she used to spank herself as a child of ten for the physical enjoyment. Lately she confided in me that she thought women's bottoms were sexy. I whole heartedly agreed and asked her if she had any fantasies concerning women's bottoms. She stated that it might be fun...

Black Cuckolding for Muslims

by Samuelx on Sep 11, 2017
Interracial Love

Another hot midsummer night in the City of Minneapolis, Minnesota. In the suburbs, for one Somali-American couple and their visitor, things were about to get even hotter. I want to see you suck his Turkish cock, Alimah Yassin told her husband Abdikarim. There was a brief hesitation on Abdikarim's part and he locked eyes with his wife Alimah, who put her hand...

BBW Anal Sex Training Camp

by Samuelx on Sep 17, 2017
BDSM

Howdy, folks. Brother Sam here. A tall, good-looking, forthrightly bisexual young black man with a poignant story to tell. Why do I bother with introductions anymore? Habit and protocol. At this point, all of you know who I am. I recently left the city of Boston, my usual hunting ground, because one of my stunts attracted way too much attention. So, I went t...

An Evening of Firsts

by MacSwain612 on Sep 16, 2017
First Time

I had the greatest experience of my young life the other night. I had gone to the local adult bookstore, to buy some jack-off magazines. I hadn't ever been there but heard that they had quite a selection. Also the fact that I was just 18 and I heard they wouldn't require I.D. for my purchase. They had every kind of porno magazine there. As I browsed a bit,...

Sarah has Some Thanksgiving Fun

by SarahCD on Dec 3, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then my writing skills have improved a little. While I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. --------- I felt like going out as Sarah and being a naughty girl. So I advertised on Craigslist for a naughty play mate. I had a prom...