Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

Brown Sugar Ecstasy

by ILuvItBlack on Oct 3, 2018
Interracial Love

After a very nice night with Henri and his woman, I took some time off, both to let my asshole return to as normal as possible, and to think about Henri, and what he and I did for each other. My only "gay thoughts" were on being in bed with him. But they were offset when I would think about how great it had been having his woman, Althea, in bed. All in all,...

Awakening My Inner Trixie Ch. 02

by Sissyhalo on Jun 5, 2018
Transsexuals & Crossdressers

For everything that happened I slept really deeply. Waking was a bit of a thought storm though with me realizing that Kiki's in bed with me snuggled up and her huge tits were pressed into me. Then there was this feeling in my ass. She fucked me last night twice after fingering me and vibing me and she was good at doing that. I didn't hurt, I definitely f...

Alexa's Journey Ch. 03

by sj_53 on Nov 26, 2018
Transgender & Crossdressers

Author's Note: I apologize for the long wait for this chapter. I have been very busy and a bit of writer's block further limited progress. I hope you have enjoyed this series. If you have read Ch. 1 & 2, I would suggest that you may want to skim the storyline before reading this chapter. Your comments and feedback are appreciated. sj_53 ********************...

Cheer Raider & SABRE Panther Ch. 11

by PervOtaku on Sep 19, 2017
Sci-Fi & Fantasy

"All characters participating in sexual activity are age 18 or older." ***** [Opening Theme: "Violet Skies" by In This Moment] EPISODE 11: "Mecha Meets its Match? Cheer Raider Captured!" "Alright, Matt, come at me," Jennifer invited. Matt smiled and ran towards her, his fist raised in preparation for a punch. The next thing he knew, he was flat on his...

Uurf Ch. 04

by Beatnic_jazzman on Sep 16, 2017
Sci-Fi & Fantasy

After breakfast the next morning I settled our bill and we strolled out onto the sunlit street. A travel agent was our next port of call and I hailed a cab in the street to take us there. "Here driver, that one will do." I had adopted the 'casual touristy look" with shirt, shorts and bold sunglass's, the person in behind the desk was , by contrast, in shir...

The Bookstore

by aaronsandler on Sep 13, 2017
Fetish

Aaron had been showing his wife off online for a few years. It started slow, with just some bikini shots with her face blurred, or faceless nudes, but over time he began to show more and more. He found groups and chatrooms that specialized in that sort of thing; guys who liked to show off their wife. And she was worth showing off. Even now, in her 30's, she...

A Fishing Trip, But I'm The Bait Ch. 08

by stickygirl on Sep 12, 2017
Transsexuals & Crossdressers

The concluding non-erotic, but nevertheless gripping, chapter about our heroine, Jane. * I knew as soon as Paul started the engine to drive me home that our relationship was doomed. When he had made love to me under the dark trees of the wood I knew that it was likely to be out last time together, at least as lovers. Perhaps at some time in the future we...

The Neighborhood Nympho Ch. 09

by lex_ludite on Sep 15, 2017
BDSM

Synopsis: Keeping his new bride, a hopeless but happy nymphomaniac, satisfied is a full time job for her harried husband. Candice can't help herself as she seduces and is seduced by everyone in the neighborhood as well as her coworkers, and discovers that many of her new conquests are as kinky in their own way as she is. * Getting Candice back to our place...

Journal Extracts Ch. 18

by JRPMTP on Sep 14, 2017
BDSM

WEDNESDAY, JULY 22, 2009. Tonight's council meeting will be the first I've attended wearing knickers, stockings and suspenders. There's no way I can avoid wearing them because Max said he intends to check and woe betide me if he finds I'm not. I've donned a pair of trousers which are hopefully loose enough not to reveal the suspenders beneath, and long sock...

Alexis' First Time Ch. 02

by alexis19901 on Apr 27, 2020
Transgender & Crossdressers

A few people seemed to enjoy the first story I wrote so I thought I'd give Ch. 02 a go. Again this is not a true story but you never know, one day it might be. After my first time being fucked, I wanted more. So back to the site where I met 'Daddy' from the previous to chapter to see what I could make happen. I'd been on the site for a number of months and...