Tiny Dicked Sissy Stories

99,700 results
Orientation
Length
Source
Infinite Scroll

The Birthday Party

by today_i_am26 on Jul 27, 2020
BDSM

Chapter 1 - The Negotiation We sat, the four of us, in a coffee shop on the high street. To the causal onlooker, we probably looked like university students meeting their parents for a catch up. The reality was something quite different. My Wife, Goddess, Dominant, Keyholder, had answered an online advert on my behalf; a couple looking for a Sissy to att...

Courtesan Ch. 07

by Goodhusband on Sep 19, 2017
Loving Wives

This is the seventh episode in a series entitled "Courtesan". If you have not read the previous six episodes of this series, I encourage you do so before beginning this chapter. "Courtesan" is romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative lifest...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Young Master Ch. 04

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"I can explain..." I was standing in a French Maid outfit, with a sissy's cum still dripping from my chin because as usual she missed a spot, and I had just been caught bent over a desk getting pounded from behind...all I needed to make it the perfect shit storm was for Dale to notice my cock was stick disturbingly hard in my panties for some mind boggling r...

Nathalie's New World Ch. 04

by Cagivagurl on Oct 19, 2020
Transgender & Crossdressers

My life was in turmoil, with my wife seemingly in control. She had unearthed my desires and now I appeared to be totally at her mercy. After Stephanie left I had a chance to reassess what I was going to do. Thinking about it I laughed, 'I was getting my fantasies fulfilled.' Sex with Stephanie was everything I had ever dreamed about and Mia, god she was ins...

Strawberry Milk Pt. 03

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Now I was planning on going home for Christmas but given how I was changed and changing I'd need some sort of plan and to spend some thought on this. In the meantime I have a few things I wanted to do and that's well... Milking my titties and blending that milk into some of my body lotion and then going out for a walk, get some groceries and do some clothe...

Exposed as a Sissy Cuckold

by lapitup65 on Sep 18, 2017
Loving Wives

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her ph...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Financial Difficulties

by tazsis1 on Sep 12, 2017
Loving Wives

We got into some financial difficulty a few years ago. I'd borrowed a lot and Elaine and I spent too much over one Christmas on the kids and family. And then I lost my job. It was all very difficult and, as these things do, it affected our marriage profoundly. While we kept our troubles from the kids, Ellen and I talked about little else -- driving out all p...

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...