Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

Prison Made Me a Better Man Ch. 01

by Cuckyboy3 on Jan 7, 2020
Fetish

Chapter 1 - Going to Prison I looked at my calendar to see that I had a doctor's appointment today. It was with some new doctor in the city. My wife, Linda, set it up for me a month ago under the pretense of a 'joint health checkup'. It turned out that this Dr. Fleming was a well-known female sex therapist who had a great reputation for helping couples impr...

A Change is Gonna Come Pt. 01

by Deviana on Apr 1, 2020
Transgender & Crossdressers

The power of the mind- to protect, to inquire and to envision. When free of the cognitive restrictions of morals and forced standards Ch 1- Betty Unleashed "I'll be back in a few hours. You know Rhonda, down the street? She asked me to go out with her for some girl time. I shouldn't be late, but you know her. What do you think of these earrings she gave m...

Lust During Quarantine

by ClosetSissy2020 on Apr 13, 2020
Transgender & Crossdressers

I've been stuck in the house under quarantine for a couple of weeks now and saw a gif online recently that gave me my first story idea. I've been writing for a few days and have got enough to trickle out the first few parts. Some bits are from personal experience, and some are things I've fantasized over. Let me know what you think, I hope you enjoy reading...

Camp Queerbait

by GoddessCompels on Sep 28, 2020
BDSM

The camp counselor uniform piqued her interest. Jessica had stopped for gas along a lonely road, and decided to enter the convenience store to get food for the last leg of her journey after filling up. She spotted him immediately upon entering. She hadn't ever seen shorts that short or tight, at least on a man. The knee high, striped socks and running shoes...

Coerced Ch. 04

by HorribleHenry on Aug 31, 2020
Transgender & Crossdressers

COERCED CHAPTER FOUR "I feel much more comfortable now you have a prick the size of a Twiglet," smiled Petronella, keeping her eyes firmly on the road ahead. "Why should that be?" I asked, embarrassed by the analogy. "When you had a sizeable and functioning prick I often felt guilty I was not allowing you to put it to good use. And, as at the moment I am...

Dark as Daylight Ch. 13

by Prolonged_Debut10 on Sep 18, 2017
Novels and Novellas

NOTE: All persons in this novel are Fictitious. If you are looking for a great deal of sexual activity this story is not for you. Those scenes that are included will be evocative, rather than just for the sake of sex itself. This story is for your Reading Pleasure. Its length is undetermined at this time, because I do not know where my mind will take me as...

Rebecca and Rob Pt. 02

by marissacd on Sep 13, 2017
Transsexuals & Crossdressers

My mind was racing as I drove back to Rob and Rebecca's house that night. Earlier that day, while working in their basement, I had discovered Rob naked, bound and deprived of his hearing and sight. My sexual impulses got the better of me, and I took advantage of the opportunity to live out a fantasy, without considering the risks. My cock stirred as I though...

Bi Big Cock Fantasy Ch. 02

by Oppswalla on Sep 14, 2017
Fetish

Thanks for the feedback everyone on the last story. In an attempt to improve the story based on suggestion, there are a few stat changes I try to sneak in there. So excuse the inconsistencies, this is really my first "erotic" story I've written and posted. So hopefully they get better with time. Please feel free to leave comments and suggestions. They are ap...

Cindy's Slut Ch. 15

by Bastinado on Sep 15, 2017
BDSM

CH 15 KNOCKING KNOCKOUT I was just about 1/2 way through my third set on the bench press when her legs appeared above my head. She was wearing short-shorts. The legs of her shorts flared just enough that I could see all the way up to her crotch. A glimmer of a small white satin thong was just visible up between her legs. Her midsection was bare, with her 1/...

Sucker Boys

by TopsyBFox on Sep 13, 2017
BDSM

We meet in a bar, me, my best sissyboy painslut & you. We are all dressed in everyday office attire; you boys look so professional in your suits. I have on a tight white blouse which strains a little at the buttons, the sheer lace of my bra clearly showing through; a straight black skirt, net stockings & heeled patent black pumps. There are other such groups...