Transexual Stories

153 results
Orientation
Length
Source
Infinite Scroll

No Holes Barred

by michaelhunt on Sep 16, 2017
Group Sex

Colette's 35th birthday was coming up soon and I asked what she wanted for her big day. We were laying in bed when I asked and she grinned at me and said she wanted another group sex party. She said the three couples of Scott & Lisa, Jeff & Rebecca and us would make it a fun night. Ever since us guys had got back from our cruise and Scott had hooked up with...

Q-tips Healthy Palace

by ClamSodomizer on Sep 13, 2017
Humor & Satire

Just yesterday I was browsing literotica. I went to the "Transexuals & Crossdressers" Top List, and after a few clicks I found what I wanted: “A Slut is Born”. It's a story about a college kid whose clothing gets soaked in the rain and so he stops at a guy's house, his neighbor or something, to get out of the rain. The neighbor gives him panties and a dress...

My Best Friend's Dildo

by Sakka66 on Sep 13, 2017
Sci-Fi & Fantasy

Sidled up alongside the Galaxy Fleet hospital ship "Mercy", the scout ship "Gazelle" was a mere speck--a hundred-meter arrowhead docked to a bulbous cylinder ten times longer and displacing a hundred times more mass. Of course, the single pilot of the "Gazelle"--30-year old Galaxy Scout Galina Barding--was used to the gigantic ego of the Galaxy Fleet. All s...

Tranny Attack Ch. 02

by cbachtland on Sep 16, 2017
Transsexuals & Crossdressers

Thanks for the great feedback. Here is part two. I encourage you to send in more ideas of what you would like to see happen. "You'll be hearing from me again, sweety!" With those words Julia had kicked me out of her apartment. I dragged by bruised and ass-fucked body home. Thankfully, Jane was not back as yet. All through the journey back to my house ima...

La Playa Ch. 14

by Fog43 on Sep 14, 2017
BDSM

The Dungeon – Three Vignettes of the BDSM Lifestyle at La Playa Author's Note: This story provides little character development, as I hope you'll see in the first two paragraphs. To understand the narrators readers may want to review La Playa Ch.1 in the Group Sex category. Scene 1: Master Paul Hector screamed. He didn't cry out, moan, groan, pant, or mum...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Hogmanay

by CalliopeTheThird on Apr 4, 2018
Transsexuals & Crossdressers

This is a work of fiction. It involves an encounter with a female transexual. Nobody is forced to do anything and there is no element of humiliation. If you need either of those things in stories of this kind, this isn't for you. * "If you're really going to do it, you've got to go to Scotland." That's what all my friends said when I broached the idea of g...

Transexual Encounter Ch. 02

by SluttyValerie on Sep 16, 2017
Transsexuals & Crossdressers

It had been a while since I had first seen this slim sexy TS, she was so sexy I thought about her quite a bit. My company had laid me off a few months after my encounter with her. I was still comfortable since I saved and had a decent severance package, but I was antsy about getting back to work. I looked around for things that I normally wouldn't have cons...

The Cigarslut

by MichelleRose3 on Sep 19, 2017
Transsexuals & Crossdressers

I strutted into the bedroom, my seamed nylon stockings swishing beneath my evening gown, a cloud of expensive perfume surrounding me. I stopped and placed a gloved hand on my satin hip. "Well," I asked seductively. "Do you like what you see?" He stared at me and took the cigar out of his mouth. "My god," he muttered. "You look incredible." "Incredibly edi...

A mixed better girl

by tre37harr on May 12, 2020
Transgender & Crossdressers

- Zoom in on a mere, simple, everyday, run of the mill 2020 living room; there was a feature wall of a large circler clock and 7 different in size and design picture frames. In the alcove were a few book shelves, stacked up with books from cookery books, celebrity memoires, fitness and exercise guides to sci-fi novels and non-fiction stories, there was even...