Transgender Stories

4,333 results
Orientation
Length
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Infinite Scroll

Cora

by Cora93 on Aug 21, 2019
Transgender & Crossdressers

Hey guys, this is my first story. It's a bit of a slow burner and although it gets pretty sexy it's designed as an introduction piece for this series. So enjoy getting to know Cora, any feedback and comments would be greatly appreciated! x ***** Introduction - I'm Cora, but most people would know me as Craig. I'm 23 years old though, according to every...

A Jamaican Vacation Ch. 01

by sissyashley4bbc on Aug 27, 2019
Transgender & Crossdressers

The only silver lining of my fiancé calling off our wedding was that I still had a non-refundable trip to Jamaica already booked. The trip gave me something to look forward to after this nightmare of a month. So a few days after my original wedding date, I hopped on a plane and went on my planned honeymoon by myself. The resort was beautiful, and coming...

Going Home with my Girlfriend

by fantaseeboy on Mar 23, 2020
Transgender & Crossdressers

My mom had met my girlfriend, Tonya, once before while she was passing through town. The two of them got along right from the start. They were both tall, strong women with domineering personalities. They both loved their motorcycles and going to motorcycle events. That was where my mom was headed, to a motorcycle rally. My girlfriend hadn't planned to go, bu...

Sleeping Beauties Ch. 05

by MicheleNylons on Dec 9, 2019
Transgender & Crossdressers

Chapter Five - Felicity's Proposition Bethany Stills had been a delight. He first saw her when he was sitting in his car parked outside of a modern business complex where he had just met with several doctors to espouse to them of the latest advances in a blood thinner developed by Kent Pharmaceuticals. One of the businesses in the complex was a women's-onl...

Sex Adventures with Alisha Ch. 07

by GeorgiaSexAdventurer on Jul 13, 2020
Transgender & Crossdressers

SEX ADVENTURES WITH ALISHA SEVEN I really didn't give it any thought when Alisha told me that she wanted me to meet her friend Mia. Even though I've been sharing the sexual awakening that Alisha and some of her friends have given me with my readers, the truth is that Alisha and I have a lot of friends, most who live normal, monogamous lives with their signi...

The Office Ch. 07

by EasilyConfused on Sep 14, 2020
Transgender & Crossdressers

The instructions had been concise, anything more detailed and it was highly likely that they would have been forgotten or led to unnecessary confusion. "Do you understand?" "Yes Ms Smyth," they each chimed. Not completely in unison but the solidarity was sufficient for Tracey to be satisfied that each understood their role. Tonight the trio were to be esc...

Neighbourhood Terror to Sissy Pt. 22

by Fibaro on Jul 6, 2020
Transgender & Crossdressers

Chapter 24 "Okay Marcy, now get back up and Minthe back to the vanity table. Jutht like it'th important to know how to apply makeup, it'th important to know how to remove it ath well. After all we don't want you developing a bad thkin cauthe of all the makeup you're uthing." Stephanie ordered not even giving Marcy a few minutes to deal with what had just ha...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Giant Steps Ch. 02

by maid4lovin on Sep 24, 2019
Transgender & Crossdressers

The sun was coming up as Sam's eyes started to flutter open. He felt good, relaxed. He looked over to his right and saw Jane deep in sleep sprawled out on the bed. They must have both tossed and turned throughout the night. He smiled as he looked at her, relishing all the connections they had made the night before. Though he was used to waking up early mos...

Barrack Room Betty Ch. 02

by MicheleNylons on Oct 8, 2019
Transgender & Crossdressers

Chapter Two – Wren Division Ho! The four Leading Recruits were hungover and hungry and in the grey dawn and cold bleak light of day they weren't sure that their prank was really worth it. They entered the cabin and found the four 'Wrens' stood at attention and immediately began to break down in laughter. "Of my fucking god you guys look stupid!" Jean Burge...