Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

Guys, Girls, and Sissies Pt. 01

by DaveLoveAss on Jul 13, 2020
Transgender & Crossdressers

This story contains sexual themes that aren't everyone's taste. If the title and tags of this story don't appeal to you then don't read ahead. For those who enjoy these stories, it starts off slower but ramps up and is worth the wait. Enjoy. ************ Looking out of the car window I watched the woods, slowly become the suburbs, which in turn finally gav...

Lost in a Female's Pleasure Pt. 06

by LucysFox on May 6, 2019
Transgender & Crossdressers

Synopsis: Damien is looking forward to a relaxing weekend free from his abusive father, but things quickly take a downward turn when he's kidnapped and wakes up in a confusingly elegant room and learns that his life is about to change forever. In ways that won't be as bad as he first thinks. (Everyone in this story is over the age of 18. This story contain...

Candy's Fashion House Ch. 04

by Cagivagurl on May 20, 2019
Transgender & Crossdressers

Thanks to Charlie again for his editorial skill, support and encouragement. ***** Alecia, what the fuck was she doing here??? I turned to look at Lauren; she was talking to Maddison who was in turn pointing over at me! I got up and walked over, "Hi Lauren I was just wondering if you wanted to get lunch somewhere?" She hugged and kissed me, "Sorry baby...

Shiny Pebbles Pt. 02

by ValoryG on May 20, 2019
Transgender & Crossdressers

Tamara and I set out on a partly cloudy, cool fall day to beach-walk, packing some sandwiches, cameras and a couple beers. I'm wearing some tight, slender jeans with a nicely tight thong underneath, along with my lightly insulated, maroon windbreaker with black turtleneck and embroidered black bra underneath. Topping it all off with conservative earrings, ba...

Candy's Fashion House Ch. 03

by Cagivagurl on May 21, 2019
Transgender & Crossdressers

The transformation begins Thanks to Charlie for his assistance and editorial skill. ***** That night I cried myself to sleep and I woke up late feeling worse than when I went to bed. I rang in sick for the next couple of days because I couldn't stop crying, out of the blue for no apparent reason it would hit me and then the waterworks would start all over...

Expectations be Damned

by Angelpenpal on May 11, 2020
Transgender & Crossdressers

The car came to a slow stop. I could hear the engine idling for a few seconds before it stopped abruptly. The silence was amplified by my nervousness. It's not like I'd never done this before, but it had been a while. "Ready?" I heard a playful voice from the driver's seat chip in. Looking over at Caroline for the first time since getting in her car I saw h...

The Double Date

by married40scouple on May 11, 2020
Transgender & Crossdressers

Josh and I talk on the way home from work about everything. He has been telling me about this girl he met at lunch by accident and then having planned their lunch breaks together. I asked if he got lucky yet. He slowed his response and said he was not so sure about next steps with her. He said she was really pretty, sexy, funny, easy to talk with, and they h...

The Good Neighbour Ch. 03

by MicheleNylons on Sep 9, 2019
Transgender & Crossdressers

Chapter Three - Beatrice McLennan Now... The young man pawed at Abigail, he was so excited that he didn't know where to start. Now that this sexy, mature woman had finally consented to his advances he was overjoyed and overexcited. He kissed her, driving his tongue into her mouth, he stroked her breasts through her blouse and then put his hands under her...

The Making of a TLB Pt. 03

by TheMarlboroMan on Sep 23, 2019
Transgender & Crossdressers

I suggest you read parts one and two to pick up a man's journey to womanhood caused by the woman he loves, his wife. Some of the items used may not be available in the market today. Rest assured they will be. The key to any conversion is the manipulation of one's mind. What the wife fails to remember is that each one of us has freedom of thought. I got up e...

A Very Different, "Three's Company" Ch. 05

by walterio on Oct 21, 2019
Group Sex

Jack, Chrissie and Janet were sitting on the deck out back. It was a Sunday morning and they were reflecting on the weeks' vacation in the Caribbean. They had heard that things could get wild at the all-inclusive resort but they never expected what they experienced. Chrissie offered, "I wish that we had places like that here at home." "There are some sens...