Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

Manning the Yard Sale

by AntaeusQ on Aug 18, 2017
Fetish

[Generously edited by CopyCarver from Literotica.] * My wife Susan spent all Friday getting ready for the yard sale. She painted the signs, typed up the Craigslist ad, and alerted her Facebook friends. She has a couple hundred of those, most her age, and a fair number recent mothers or pregnant. I used to give her grief about all the time she spent online,...

Courtesan Ch. 28

by Goodhusband on Sep 19, 2017
Loving Wives

This is the twenty-eighth episode in a series entitled "Courtesan". If you have not read the previous twenty-seven 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 alt...

Tim Ch. 04

by TimT1972 on Sep 12, 2017
BDSM

This story continues on from "Tim Ch. 3 -- Tim serves as a kinky French maid & is punished & humiliated.". This chapter works as a stand-alone story. * It was now almost two years since Tim had been kidnapped and forced to work as a submissive sex slave. In that time he had accepted his status as a plaything for rich women and had got used to satisfying t...

Peeping Tim

by JoeVartos on Jun 1, 2020
Exhibitionist & Voyeur

Tim was an 18-year old high school student nearing graduation. Tim was tall and athletic, but a shy kid. He had lived next door to Sadie and her family his entire life. Tim and Sadie's parents were good friends and often went out to dinner and had parties together. Any time one family had a party or event, the family next door was invited. Which also meant t...

Christmas Love

by L.A. Wicker on Sep 19, 2017
Romance

A big thank you to Tigerjen for taking time out of her busy schedule to edit my story at the last minute... And I mean the last minute! * * * * * It was a long five hour drive from the hospital. Seven year old Tim, and his father had been doing it since his mother had been diagnosed with cancer, last spring. Tonight was Christmas Eve, and it was snowing v...

A Russian Kiss

by MatveiPavlovitch on Sep 19, 2017
Group Sex

// Dedicated to LEAGEL, my wonderful editor// My name is of no importance. In this story I wasn't the hero, I wasn't even an extra. Yes, it is true that I had a part in this play. But for me the most important thing was to be there and to let it all happen. My wife Anastasia and I live in Denmark. I work in an international technology company. She is a...

The Descending of Jessica Ch. 11

by Jessie92 on Sep 19, 2017
Romance

So, in the last chapter we finally arrived at Brent's big fuck up. If you haven't read the previous 10 chapters, you probably should, or you will have no idea what is going on. I haven't as yet gotten a lot of feedback since Chapter 8, so there's not much to say here. Sorry for the delays in getting this out, but as I've said before, life has been busy. I'm...

At Some Point in Time

by bigpapabare on Sep 14, 2017
Erotic Couplings

Chapter 1 - The First Encounter When Tim first spied Lois it was in passing in one of the passageways of their winding office complex. As they passed each other they exchanged brief smiles as co-workers do and continued along their separate ways—although their minds immediately formed visions of the other. Tim was an older and married man, who was beginnin...

Divorcing Myself from Myself Ch. 09

by ThatJimGuy on Oct 22, 2019
Erotic Couplings

Note: This story is part of a small volume of stories that I have posted here previously. They will appear with different names as chapters (10 in all). I think these stories stand alone well, but they are meant to be read as part of a larger work entitled "Divorcing Myself From Myself." This chapter, #9, is called "Full Report: A Play in One Act." It has...

Dot Makes Tim a Cuckold Ch. 13

by wantwhitewomen on Sep 19, 2017
Loving Wives

After Tim's wife left with Antwan he was extremely sad and very mad and confused. Was this the end of their marriage? Was she leaving him or should he not be there when she got back? Tim didn't know. Hell he didn't know if he even wanted to be married any more. He was cussing and yelling to no one that he would dump the bitch and divorce her for fucking anot...