Shemale Sissy Stories

7,624 results
Orientation
Length
Source
Infinite Scroll

Hentai Heaven

by hornyboi666 on Sep 28, 2020
Fantasy

=============================================================================== Important notes: 1- It seems that I am not a good writer. as of now, I wrote 17 chapters about (John - North Korean 21 yrs old boy). I made an effort to make it a story with a sex scene in each chapter and build up a story. If you are in rush or not sure if you will like it or no...

Open in Reader

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,...

Specimens of Gender

by darkheathyr on Sep 14, 2017
Sci-Fi & Fantasy

"Hmm. One more chapter?" I rested the thick, hardcover book on my chest and turned my head to check the clock. It was only 11:47 - late, but not as late as some of the nights I'd put in lately. Still, I did have to be up at 5:00 in the morning. "Better not," I decided with a sigh. Since it was too big for the nightstand, I reluctantly dropped the book on fl...

Chronicles of Heather Maureen Ch. 09

by HeatherMaureen on Sep 16, 2017
Transsexuals & Crossdressers

Final Exam While I was waiting in bed last night for George to join me he had gathered up my clothes and purse then locked them in my car to make sure I'd spend the day with him. His clothes would fit me like a tent and his wife's merely like a pup tent so they were no help. I resigned myself to staying here and inside for the day. He made breakfast for...

The Secret of the Island Pt. 04

by neoview on Oct 30, 2018
Sci-Fi & Fantasy

You thought the story had died but it was just my lazy ass refusing to continue. Also I was busy with my girlfriend so I couldn't really focus. Yes, I have a girlfriend now. Well "she" prefers to be called a girl even if she isn't. Without her I would finish this story much faster, but... she gave me some interesting ideas which were too good to ignore. ***...

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...

New planets new experiences

by latexdoll on Sep 26, 2017
Science Fiction

The little blue screen lights up as the video begins, the audio being transmitted directly to your audio implant. "We thank you for choosing Stellar Gold, the finest shuttle service, now with service to all 7 connected Galaxies with 2 more scheduled by 2475. Please enjoy this 10 minute video." The year is 2469 humanity has known that they are not t...

Open in Reader

A Dream?

by njcaptionlover on Sep 16, 2017
Transsexuals & Crossdressers

I nervously paced back and forth in my home waiting for the escort that I had called for while constantly checking my breath to see if it smelled good as well as my body. I felt like taking another shower but was worried that the escort would arrive while I was in the shower. As I continued to pace I wondered what she would look like, hoping that she was as...

Once Upon a Laundry Ch. 02

by thekestrelkid on Aug 7, 2018
Transsexuals & Crossdressers

At 7 sharp I knocked on Jessy's door nervous and anxious still not entirely sure what I was doing. I couldn't believe how hot a time I had down in the laundry room with her making me finger my own ass like a "pussy" and jerk off for her. The thought of taking it to the next level was exciting. Jessy answered the door dressed only in an over sized t-shirt a...

Made to Obey Ch. 07

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...