Sissy Lingerie Stories

30,229 results
Orientation
Length
Source
Infinite Scroll

Chains Willing Ch. 04

by Radiantlies5 on Oct 31, 2018
Sci-Fi & Fantasy

Chapter Four: A Princess Bound In... "We held hands as we watched their world burn." -An excerpt from the journal of Illiana Worms. She wrapped my, now almost entirely white, hair around her hand on the back of my head and forced her cock deeper into my throat. My nose dug into her bushy pubes and my chin rested on her balls. Sweat painted glistening love...

The Feminisation Initiative

by Slipperylock on Oct 31, 2018
Transgender & Crossdressers

It begun in the year 2100. A culmination of over-population, unemployment and sexual harassment demanded a response. In America, where the crisis hit hardest, there were massive talks and debates across the country. How was the problem to be fixed? Global warming had been identified, assessed, targeted and dealt with. Beginning in 2030 with the first femal...

Angel without Wings Pt. 02

by Madelyne13 on Jul 16, 2019
Erotic Horror

The devils influence continue to grow. Desire and dreams merge with reality. Can even an angel comprehend the malign purpose? I woke up the following morning as fingers of light poked into the room, around my curtains. With one eye open I pulled the bed covers over me and buried my face in the pillow. I tried to find a context for what had happened, but the...

Someday Scores Settled? Ch. 01

by eymach on Dec 25, 2018
First Time

The reader is encouraged to read 'The Beach' as it's a story that provides a little insight and background about Ryan and Ricki's parents and their close relationships. Hopefully each of the next few stories can stand on their own at the same time exhibit a link to the next. ***** Chapter 01 Doing the Deed For Ryan Winn Gunnels and Ricki Lyn Boden, it w...

"Caught By Her"

by tcs1963 on Apr 10, 2019
BDSM

Copyright 2019 by tcs1963 All Rights Reserved This story contains aspects of Bisexuality, Homosexuality, Female and Male Domination, and Force or Coercion. Please have an open mind. CAUGHT BY HER By tcs1963 Chapter 1 "The Beginning" Tom roughly grabbed the back of my head, holding my face tight against his groin. As he slid further into my throat, ca...

Futanari Academy Ch. 08

by TheOrcKing on Jun 5, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. ***** "Pull the lead out of your ass Surbrina!" Miss Angeli barked, blowing her whistle. "You're a Nazi, coach!" Surbrina whined as she moved th...

Happy Birthday Mike Ch. 01

by TheOrcKing on Jun 12, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** (All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Synopsis: It's Mike's birthday and he is stuck home alone with his...

Wife Humiliates, Hubby's Turned On

by Quietoldie on Oct 21, 2019
Transgender & Crossdressers

The wife Carol is the main narrator of this story with some comments from her hubby Bernard. I've tried to give a slightly different twist to cuckolding and cross dressing compared to many stories on Literotica. ***** CAROL "You're not much of a man are you?" I said to Bernard. I was angry and unfairly blamed my hubby after receiving the news that his spe...

Cum Addicted Husband Ch. 06

by Subone1 on Dec 9, 2019
Loving Wives

The big day finally arrived - my final exam! If I make it through the party tonight, I will get to be my wife's cum slave forever. I wouldn't have to settle for "left over cum", I would be entitled to eat it directly from her freshly fucked cunt whenever it was available -- A treat I relish with delight! I took the day off work at Karen's direction - she m...

Ms. Tanaka Fixes Me Ch. 01

by chenwanli on Apr 27, 2020
BDSM

Chapter 1: Meeting my Future Wife and her Mother I met my wife Hiroki in my mid-20's when I was living in Osaka. I'd been living in Japan for a few years leading the bachelor life and dating some gorgeous women but the majority were stereotypically Japanese: expecting to be subservient and deferential to the man, which I found boring in anything longer than...