Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

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...

Coerced Ch. 03

by HorribleHenry on Jul 27, 2020
Transgender & Crossdressers

There we were, Petronella and me, sitting in the bed opposite one another, admiring each other's breasts, and wearing identical silky pyjamas. From the outside looking in we would have appeared to be a very erotic pair. And I was anxious to get on with some practical eroticism. "I have decided, Honey," smiled Pet. "Tomorrow we will gather up all your male c...

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...

Sissy Perfection

by cornthuxton on Dec 23, 2019
Transgender & Crossdressers

Hello. I had done just about everything there was to do mature, lesbians, trannies. And several times each variety. So I thought it was time for a twink. As with my previous adventures Hong Kong was my hunting ground. Two, week long trips a year made it easy for me to indulge me desires. I guess I am pan sexual...whatever that means. I'm open to lots of...

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...

Becoming Joey Ch. 07

by First_time_bi on Apr 27, 2020
Transgender & Crossdressers

Monday Susan urged Joey to get moving. "Just put on a pair of shorts and a t shirt honey. Nobody is going to see you." "Dr. Beaumont will see me," Joey said, as she stumbled to the bathroom to fix her hair and makeup. "Dr. Beaumont already loves everything about you." "I'll just be a few minutes, Mistress...please?" "Don't take too long. We don't want t...