Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

The Talisman is the Longest Man

by DJBlax on Dec 12, 2018
Erotic Horror

Tim was never that fond of holidays. But for some reason, Halloween had a strange appeal. Maybe it because it was an excuse to act weird. Or maybe it was just the fact that people loaded up on beer and/or candy and just had a great time that made this an exception. With Vampires promising to dig teeth into the succulent flesh of necks and the thought that a...

Medical Training

by cybersky on Sep 13, 2017
First Time

Tim was a university student and had recently begun getting his doctorate, moving away from his old university friends. Moving away from his best friend, Nurah, was the hardest part. He had become almost like a member of the family, a point that still confused him. Nurha's family were of Pakistani origin, and always surprised him with how open and welcoming...

A Strange Advert

by Lion24655 on Sep 1, 2017
Group Sex

Chapter 1 It had seemed a strange advert. Not even in one of the pornographic magazines - it was in the local newspaper "personals" column. "Couples: We can help you have the experience of a lifetime. Would you like to get roped in to something magical? You are bound to enjoy it. For more details, phone..." And it gave a local number. It wasn't that Tim a...

Hot Babe Romi Ch. 04

by MONALISALEE on Sep 16, 2017
Group Sex

Next day, in the afternoon, Tim knocked the door and Romi opened it with a big smile on her face. She offered him a seat and sat in front of him. She was wearing pink lingerie and was looking damn sexy. He was little shy but gathered courage and said, "Mam today I don't have anything for sale. I have just come to meet you." Romi was surprised but kept on...

His Female Client is Really a Man

by walterio on Sep 16, 2017
Transsexuals & Crossdressers

Tim had just finished cutting the lawn and it was time to collect from Michelle Andrews. He always loved collecting from her as she always gave him the most incredible blow jobs. She didn't just suck his cock she made love to it. Sometimes she would make him last for 30 minutes before he unleashed a volcanic like ejaculation and sprayed his seed all over her...

The Adventures of Tim Bodge Ch. 02

by thodge1945 on Oct 6, 2020
Sci-Fi & Fantasy

I would like to Thank Driven2Read for helping by Beta Reader, Proof reading and some editing. Chapter 2 Tabitha and Tammy walk into the Officer's Lounge, looking around and seeing how the lounge looks for the first time. It is looking good. Tabitha said This looks like a real nice place to relax in. The girl's order drinks and cake, and Tim has asked them...

Making Tim Happy: Expanded

by Alan D on Aug 19, 2017
Exhibitionist & Voyeur

Author's note: This is a major rewrite of the original story. Your input told me I had rushed you through the development of their relationships and left too many things unexplained. Hopefully this will make it all clear to you…. Any comments? ***************************8 "You're missing the show," said Eric with an evil smile. "What do you mean?" answ...

Love Like a Blue Shell Pt. 02

by Spector_Dugan on Mar 13, 2018
Group Sex

Welcome to Part 2 of our epic four part story. Warning: as long as Part 1 was, this is even longer. Last time, Taylor got a bit too drunk and fooled around with another guy while her boyfriend watched. And she felt really bad about it. Her solution? Well, maybe two wrongs don't make a right, but what about two pussies? Everyone is over 18. Although he had...

Dot Makes Tim a Cuckold Ch. 08

by wantwhitewomen on Sep 19, 2017
Loving Wives

The next step in cuckolding is achieved by Dot. So if you don't want to read about her doing it and really pushing her husband stop now. * Since the kids were at one of grandmother's house, Tim and Dot were able to sleep in until almost noon the next day. Then they dressed and did the normal things they usually did on the weekend. Around 1PM Dot told Tim s...

Tim's First Date

by dauq on Oct 15, 2017
First Time

“I can’t believe she said yes! Dude you’re so lucky!” Phil said as he walked down the hallway his hand slapping Tim’s back. “I mean, Julie, she’s like the hottest girl I’ve ever seen.” Tim felt a little uneasy. Why was she going out with him? I mean it wasn’t his idea really. It was almost like his dad talked to her dad and then suddenly they were going on...