Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

My Teasing Hotwife Ch. 06

by footslave85 on Apr 23, 2019
Fetish

Part six - the morning after I awoke to feel a sharp pain once again in my balls and it took me a moment to remember that I was still in the chastity cage and my cock was trying to get hard once again. I'd been woken up a couple of times during the night with the same pain and it took a few minutes to gather my thoughts and let the pain subside. The room n...

Steph and Giulia Ch. 05: Short Shorts

by BigHand32 on Sep 16, 2017
Fetish

It was dark. Giulia looked at the clock. 7 AM. She had explicitly told Stephen to come to her room after he took a bath, and "Come fuck me like a man". This wasn't for her. In fact, the thought didn't really appeal to her that much... his tiny body and tiny cock working inside her until he had a pathetic orgasm. She just wondered if he would if he was not j...

Count Down To Moonlight Ch. 05

by fairydust22 on Sep 16, 2017
NonHuman

The long silver car sped down the dark deserted country road, its headlights illuminating the dense forest as it slithered and wound like a snake to its destination. The occupants of the car sat quiet and still. Keelay, whose pale face rivaled the quarter moon, twisted her fingers and tugged at her skirt. Her head swam with doubts and questions. What the hel...

No Safe Word

by CBM514 on Sep 14, 2017
BDSM

No safe word There is a world of difference between a slave and a submissive. Submissives are treated fairly (most times) and their master or mistress will consider their limits and occasionally push past them for one reason or another. But in truth it is the submissive that holds the power since they have a "safe word" that both parties have agreed to hol...

Wife and I Get a Roommate Ch. 05

by tonyl65 on Sep 25, 2017
Group Sex

We have all been getting along really well. David enrolled in the local community college and would be starting in September. David was also looking for a part-time job. Carol and I were going to the local State College and starting back about the same time. It was already the middle of August and we only had a couple more weeks before our schedules would ge...

Sissy Hubby Ch. 07

by buttboi on Sep 19, 2017
Transsexuals & Crossdressers

I wish to offer my thanks to Earl Grey for his editting assistance. Your feedback and votes are ALWAYS appreciated! *** Kim and I stepped through the door to my house to find my wife Stacy, just inside wearing a floor length black, silk robe. Her make-up was a little thicker than usual, which gave her a trashy appearance: she looked hot! Stacy took my ha...

Beneath Ch. 02

by Shwenn on Sep 26, 2017
BDSM

I woke the next morning immersed in a feeling a dread. I'm normally long to wake in the morning but the anticipation of the day brought me to a fully wakeful state almost immediately. I made myself coffee anyway, habits being what they are. I had two hours before I had to leave. Sipping my coffee, I reread the instructions. I had done so the previous night...

Teaching Assistants CH. 02

by Eli is Coming on Sep 12, 2017
BDSM

[Chapter one is located in the Transsexual/Crossdressers category.] ANNA The following afternoon as was custom Xander and Anna met for coffee before their Latin America class. Both were punctual to a virtue but this time she was early, giving her the pleasure to find him walking through the door. Well, walking was not the proper word for it, more like hobb...

When Johnny Comes Marching Home Ch. 01

by MADMADMADMAXine on Sep 15, 2017
Non-Erotic

Hero veteran returns home disgraced and in poor health. Once a big, scary, well-conditioned brute of a man, Johnny used to be a mean and nasty son of a bitch. If you were his enemy, especially if you were his enemy, he'd as soon as kill you than look at you. Now just a poor excuse for a man, broken and despondent, he was the shell of the man he used to be....

Chrissie a True Slut

by easyballs on Sep 14, 2017
Erotic Couplings

Chrissie 'Cums' to prefer the 'Bully Boy' to Fiancée Again my thanks to Jill for her input and suggestions. If you are easily offended by stories regarding sexual intercourse don't continue reading go buy the dandy! ***** Hi my name is Chrissie, I'm a nineteen year old student and I just had to tell someone about my own story. I had a boyfriend who I was...