Transsexuals+&+crossdressers Stories

15,868 results
Orientation
Length
Source
Infinite Scroll

Annual Physical

by trotsfox on Jan 6, 2020
Transgender & Crossdressers

Editor's note: this submission contains scenes of non-consensual or reluctant sexual situations. Author's Note: This story was written with the prompt: "Something medical/casual, where it's not acknowledged that anything sexual is happening." -- "Dr. Carson is ready for you!" Your head perks up, the words pulling you out from your half-asleep daze. You...

Cocks are for boys

by Sissyhalo1 on May 12, 2020
Transgender & Crossdressers

It all changed my 3rd week of October in my first year here at college. I'd just started to settle in with the dorms and classes and started to have a social life. Well not really, with college so big I didn't matter so I wasn't unpopular enough to get tossed from the parties I went to with everyone else. I was just part of the crowd. Drink a few beers,...

The new Secretary Ch. 03

by 13feathers on May 13, 2020
Transgender & Crossdressers

Melody climbed the stairs, teetering in her new, tight long skirt and stiletto boots. She almost fell twice, and only saved herself with a quick jerk of the railbar. Adam was waiting for her, not paying her any attention until she was standing right in front of him. 'Hello Adam.' she said softly. 'Good morning Melody.' he said with a scowl. 'Can you gues...

No Turning Back

by Wanttobefemme on Jun 9, 2020
Transgender & Crossdressers

The story continues. Reading my previous submissions may help you appreciate what's about to take place next. However, the story also stands on its own. The shower was nearly over, but the real journey had not even begun. He had never experienced anything even close to living out this lifelong fantasy. Being dressed and used as a plaything, a slave, to...

Journey of a Boi Ch. 01: Prologue

by Anissa23 on Jun 9, 2020
Transgender & Crossdressers

Everyone has their own way of going through college life. Some people just go through the motion and study meticulously. Some people party and flirt every night. Still, most people will properly finish their studies and graduate successfully. The result, university transforms you completely into a different person from the day you started. Likewise a boy na...

Babygirl Ch. 03

by AdamWestie on Jul 13, 2020
Transgender & Crossdressers

I woke up refreshed and took off my nappy. It was dry. I used the bathroom, had a shower and a shave and then wandered into Mummy and Dada's room. They were starting to stir, so I crept under the covers and wormed my way between them. Soon enough they were stirring. My little peewee was all hard and pressing into mummy's butt crack, I could feel dada's big p...

Goth-night Getdown

by JaxRhapsody on Jul 6, 2020
Transgender & Crossdressers

"90's goth, I like it. Too many of these people are borderline emo looking," she complimented, sitting next to him at the bar. "Ah yeah, thanks. I just prefer the look I grew up with," he looked at my pair of Tripps and Anarchy boots. "Same, look," she stood up, presenting herself; black miniskirt, Mary Jane boots, flannel shirt and push-up bra. "You like?...

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

Natalie Succumbs Yet Further

by natalieukcd on Sep 28, 2020
Transgender & Crossdressers

I was lying on my bed on my back with my legs dangling over the side. I had Lewis stood between my legs, gloating at me in my underwear and cock cage. He suddenly moved around the bed and undressed quickly, as i watched him behind me. I was so nervous that i did not move. "Lift your knees up Natalie and hold them up behind the knees." I did as i was told a...

Daddy's Sissy Staircase Ch. 02

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

Thanks for reading and your comments! As this is the continuation of a story, it will make a lot more sense if you go back and read Chapter 1. Almost from the very start of us getting together, there were sex toys and accessories added to the mix by Daddy to make the experiences more and more titillating for both of us. From the beginning, there was always...