Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

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....

Creating Ginger Ch. 06

by Ms_Allison on Jun 9, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consistent in referr...

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

Candy's Bukkake Moment

by Stillherer on Sep 17, 2017
BDSM

She had been so kind, so understanding of his needs, so nonjudgmental that he found himself gratefully allowing her to make him into the girl he had always wanted to be. When she hadn't freaked upon discovering his stash of female underwear and had honestly tired to understand what it was about them that excited him so he couldn't believe his luck. His bigge...

Getting Nailed

by jbirdman on Sep 25, 2017
Fetish

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something e...

Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

Training of Mistress' New Sub Day 01

by naughtyboy082 on Sep 19, 2017
BDSM

As Mistress Sharon has requested, a written story... THE FIRST MEETING MISTRESS SHARON sends out a late night text that her new submissive has been waiting for anxiously all week long as he sought to prove his obedience and worthiness. "Congratulations, sub! You have successfully completed your probationary period...official training begins in the morning...

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...