Ultimate Sissy Weekend Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

Cyber Sissy Ch. 03

by missvicky53 on Sep 25, 2017
Fetish

"Good, you may begin by repaying my hospitality. I want you to clear the table and rinse the china. You may then put everything in the dishwasher. When you are finished, I will continue your training." I obeyed at once, being very careful with the china. I wondered where Megan was while I was doing my domestic chores. The answer to that came a minute later....

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Bayonetta's Abuse Ch. 03

by ChainedToAKeyboard on Sep 13, 2017
BDSM

As anticipated, James will be spending the weekend at Jeanne's manor while Bayonetta is away on business. What pleasures and horrors await within? Bayonetta's Abuse III - Weekend At Jeanne's It was another bright spring day as James and Bayonetta made their way up the long walkway to Jeanne's estate. The compound was well fortified with a chain link fence...

Cuckold CEO Ch. 09

by drdick69 on Oct 15, 2018
Fetish

Monday morning came as a blessing. The weekend turned out to be a sex charged fuck-fest that culminated with me eating James' cum from my wife's ass. All day at work, my mind returned to the events of the weekend. The domination, power and shear supremacy of James was astounding. He had total and absolute control of not only my wife, but of me also. I could...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

The Sexy Cuckold Couple Pt. 02

by cuckcpl4play on Sep 26, 2017
Fetish

While neither of us slept great, we did manage to get a little bit of rest before we were suddenly woken up with Jen's phone blowing up. She checked her text messages to see that Brian had requested we meet in his office at noon today. He made it clear that unless there was an emergency or other, he would expect to see us both there. We were a bit surprised...

The Sexy Cuckold Couple Pt. 12

by cuckcpl4play on Sep 19, 2017
Fetish

AGAIN, cuckold story with humiliation and if this offends you, please don't read! While fiction, we have experienced ample aspects of this story and this lifestyle. ***** Part 12 Vegas The men hustled out of the limo and rushed up the stairs to get a seat in close proximity to my wife. Master ordered me to keep sucking the used condom and rather than allo...

Steel Heaven

by LockedDarius on Sep 11, 2017
BDSM

I stood in the shower, allowing the hot water to caress my body in an attempt to wake myself up. The thought of another long day at work wasn't helping the situation, but at least it was Friday. "Get through today and enjoy the weekend," I thought. I stepped out of the shower and immediately realized I had forgotten to bring a towel into the bathroom from t...

Wife in Control Ch. 03

by wifetoy on Sep 25, 2017
Fetish

This is the third chapter in the story of my submission to my wife for punishment for failure to control my orgasm. My full offer of punishment for my transgression is fully set out in the first chapter for your reference. Each part of this story is true and is told as it actually occurred. As with the previous chapters, my wife told me to let the readers kn...