Sissy Strapon Stories

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Fantasies Fulfilled Ch. 02

by HerLittlePiggy on Sep 19, 2017
Group Sex

Sherry stood by the bed dressed in a black leather corset that accentuated her big 36dd tits, her tiny waist and her full hips and beautiful round ass. High healed thigh high leather boots completed her dominatrix outfit and a thick black strap on hung lewdly from her waist as she barked orders to me and the three muscular men in the room. It was September...

Punished Asian Shoplifter Ch. 11

by asianspankee on Sep 15, 2017
Anal

It's now time for my second to last punishment session at your office. It's going to be another after-hours one, which hints that something unusual is going to take place again. I cringe at the thought of what else could it possibly be that I haven't been subjected to already? Well for starter, when I walk into your office there's an odd-looking wooden benc...

Mistress Monique

by bleedndkn on Sep 25, 2017
Fetish

I met Monique at a show. She wore a tight black dress, dark eyeshadow and was by far the hottest girl at the venue. I didn't have a chance. A mutual friend introduced us and I became immediately enraptured with her and in the days to come would constantly think about how to spend more time with her. Then, after an evening with Monique and mutual friends at...

Life With Miss Ida Ch. 06

by Sheermistress on Dec 5, 2017
Transsexuals & Crossdressers

Life with Miss Ida – Part 6 - A New Development On most weekends Mistress and I would enjoy a nice wine or two with our evening meals however, on this particular Saturday, Mistress was enjoying more wine than she usually drinks – we had decided to do the twin, 'Schoolie-Slut' thing this evening, with both Mistress and I in matching, tartan mini-skirts, whi...

BDSM by the Book

by Stefani on Sep 11, 2017
BDSM

I was rather slow when it came to dating. My love life moved at glacial speed until I met my wife. In high school I was skinny and too short to be any good at sports. At school and in the town I grew up in outside Sioux City, I got pushed around a lot by other boys, all of which translated into a lack of confidence. Particularly around women. When I got to...

Penis Shrinking from Chastity

by tinywhiteboi on Sep 19, 2017
BDSM

After losing my wife to her big dicked black lover I was pretty depressed. I knew that my 4 inch skinny penis was not big enough to satisfy any experienced women. Sure it was fine as a teenager fucking young girls, but in my mid thirties I figured pussy for me was likely to be rare. While reading pornography on the web I discovered stories about small penis...

Last Friday: First Sissy Experience

by sissysyzygy on Mar 5, 2018
Transsexuals & Crossdressers

Been a lurker for a little while, and thought it was time I contributed with a post! *** Title: Last Friday "You ready for your surprise?" she asked me coyly. "Yes!" I said excitedly, thinking of the possible toys we had been looking at online, or perhaps a striptease. We had our eye on a Bad Dragon dildo as our starter strapon kit had grown my interest...

Sissywife Humiliation Action

by Cocktopia on Sep 15, 2017
BDSM

The dyed-black haired girl, mistress of this dungeon, was covered in large colourful flower tattoos, her hair cropped in an uneven fringe around the shaved sides of her head. Her nipples, clit, eyebrows and nose were pierced and threaded with simple silver rings which glinted in the dungeon's harsh light. She was very young and very pretty but her sex appeal...

Watching My Wife!

by limpjake on Sep 16, 2017
Loving Wives

My wife's decision to allow me to watch her began on Sunday at our family BBQ over memorial day weekend. We went to a near by state park camp ground where family members were camping for the weekend. We were having a good time conversing with family and friends, and eating the deliciously grilled chicken. That is when my wife asked me to walk with her to the...

Chatroom Trick Ch. 03

by ukmaleslave on Sep 15, 2017
Transsexuals & Crossdressers

For those of you first reading this let me fill you in on a Friday that that opened my eyes. I am a 26-year-old normal guy who had for sometime been flirting and playing with an older woman named Mary via an Internet chat room. She was about 41 a firm fit body and gorgeous red hair, perfect, better than that she didn’t live too far away. Our chats didn’t rea...