Sissy Tim Stories

12,400 results
Orientation
Length
Source
Infinite Scroll

Sissy Awakening Ch. 03

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- Sissy Meets Sarah's Bull - Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these! She said to wash inside and out, and not to miss a spot. That meant...

Waking Holly

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It's been about a month since I told Holt, Holly the truth and moved her into my house. I never expected the side effects of what I did to her to be her to be her becoming a whole other person. I know it sounded like that's the point but the point is that you changed them, bent them, broke them and made them worse. And I fucking hated Holt, I really fuckin...

Sex Change for a Cursed Exchange Ch. 01

by sucuminx on Sep 19, 2017
Transsexuals & Crossdressers

You wouldn't believe me when I say that today changed my life. Why? Well it all started with Randy Smith, a delinquent classmate in my college. We grew up together ever since middle school and we been good friends since then. He was your typical bad boy with slick blonde hair that matched his toned muscular body and that smile that would make any girl go i...

Cable Guy

by Girochen on Dec 10, 2017
Erotic Couplings

Sometimes I write little snippets, sometimes they are longer. Like snapshots of life, they occur to me and I must capture them. This is one that I wanted to share because I like it. It has some weird in it, man on trans man-girl, and some regular sex. But the real story is in between like a waffle holds the butter and syrup but isn't anything without the act...

Hugo From Pode Hole

by egmontgrigor2010 on Sep 13, 2017
Romance

CHAPTER 1 The ruggedly handsome guy with long black hair and very pale complexion leaned back on the chair in the half-empty Starbucks and wished he'd chosen a coffee that tasted like coffee. Idly he studied three under thirties women at a table who were dressed like businesswomen. He winked at one and she turned away embarrassed and their heads went togeth...

The Stress of Revision Ch. 02

by TheJonsterMonster on Sep 13, 2017
Erotic Couplings

Part One. Jon twisted the shower control and was rewarded with an ice cold gush of water in his face. "Have you got it warm enough yet?" came the whisper from the other side of the curtain. "No!" he gasped. "Just getting warm now," he added a few seconds later. The curtain parted, and Bianca slipped in beside him, and promptly positioned herself under...

The Descending of Jessica Ch. 17

by Jessie92 on Sep 19, 2017
Novels and Novellas

Welcome back readers, thanks for coming on this journey with me. I know it's been a while, but life has been, well interesting of late. By my count this is the 17th chapter in what was supposed to be a three or four chapter story, and it's still not quite done. Well, the second part isn't done, obviously since these last few chapters were originally epilogue...

Watching the Detectives

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** 1 Philippa For the umpteenth time I needed to move to get my circulation going again. I tried to stretch my legs but it's not easy in the front seat of my small car. Fuck, I thought as I snagged my tights against something beneath the steering wheel. If that was another pair ruined I would scream. I was parked facing a nondescri...

Magic Dress - Fleur

by SlightlyRude on Sep 24, 2019
Transgender & Crossdressers

CHAPTER 1 I met him in Paris, the most romantic city in the world. We were both spending a bit of time after finishing school. I was taking a year before university, he had just the summer after leaving school and before starting work. Two eighteen-year olds out in the world. He thought I was French and local because of the way I was talking with some othe...

The Waitress Ch. 10

by goldsssnake on Sep 19, 2017
BDSM

You cannot use this story for any commercial purpose, and you cannot publish it in any website other than Literotica. Respect original writing. Thanks. ******* I dedicate this story to Connie the Hot Cunt, and its conclusion to miss X, there in Alabama. Thanks very much to all the readers that heartily agreed with me in my points of view that I expressed...