Spanked Sissy Stories

24,820 results
Orientation
Length
Source
Infinite Scroll

The Making of a Mistress Pt. 03

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This fictional series about a character first introduced in my "Coming Home; Coming Out" serial continues with Marie, now engaged, is going to meet Charles's parents. She also takes Charles to meet her mentor, Dr Sara Walters and her sissy cuckold, Paula. As in all of my work, every character is over 18 years of age, and all sexual practices a...

The Wedding Ch. 05

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Patti Cake part 3) Chapter 5 -- Femdom, Fucking and Femininity... At the end of our time spent with Ms. Walsh, I was left with a lot of questions and I wasn't sure how to deal or cope with any of it... But one thing was for certain, I was starting to see more of the old Patti bubbling back to the surface, being direct and without compromise... The whole d...

He Brought Me Panties

by Cute Little Thing on Sep 14, 2017
Transsexuals & Crossdressers

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. This made sense and I wasn't that surprised. I'm on the small side, 5...

HSPL - Trip to the Sorority

by sissydn on Aug 7, 2019
Transgender & Crossdressers

"After being left on the road by Meghan and Sophie, princess was caught by Cindy and her companions. Zoe, apparently the leader in the group, had informed sissy that she could get back to Sophie and Meghan if she pledged the sorority and joined with honor. If she chooses not to pledge, they would drive her to the other end of town and leave her there in her...

Sissy Life Pt. 04

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I stood to attention on my 'sissy spot', the small 'x' drawn on the floor of my Mistress' study. My spot faces the desk behind which is a large leather chair. It is here that I was told I would be placed in chastity. It was here on my spot that events unfolded leading me to serve my Mistress' lover Tony. I was understandably nervous about being stood here ag...

A Roleplay Gone Awry

by ronald81 on Sep 15, 2017
BDSM

All people within this story are over the age of 18. ***** For as long as I can remember, I have always been into cross-dressing as a young boy. Yet, I would hide these feelings deep down as I grew up. The following story is partly true, as much as I can remember. It all started when I was playing a roleplaying game featuring a text based game that was su...

She Forces Me into Cuckoldry

by hismasterdivine on Sep 25, 2017
Loving Wives

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax! ***** Dominant girlfriend wants a black lover, deluded b...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

Quenching Thirst Ch. 02

by PutItInMyMouth420 on Jul 10, 2018
Transsexuals & Crossdressers

So there I was covered in Black mans jizz and piss, handcuffed to a handrail in a gay strip club. I was hard as a rock at this point and had realized in the midst of my humiliation that the sexiest part of all of this degrading shit was my lust for Mr. Warden. I wanted to know how it felt to truly give myself to a real man. Even though my ass was virgin, i w...

Cruise Ship Cuckold Ch. 08

by Angelscuck on Sep 14, 2017
Novels and Novellas

Story from Angel's point of view: My husband asked me to write this next installment due to the fact that he is a bit tied up at the moment. I am more than happy to tell you our story. As you may or may not remember, my husband and I were in the captain's wife's cabin with him and his nephew Daniel. We were there to pay up on the bet my husband lost to Ev...