Sissies Stories

1,006 results
Orientation
Length
Source
Infinite Scroll

The Fantasy Twist Ch. 02

by oneguy4fun on Sep 18, 2017
Transsexuals & Crossdressers

Sunday morning was a morning for sleeping in. Dan spooned Lisa's naked body. This was not typical of Dan, as he usually preferred to sleep facing away from Melissa. Melissa was happy with this change. She enjoyed the warmth of his body. She stirred under the covers, snuggling even closer to Dan. Dan broke the morning silence, whispering into Melissa ear, "L...

The Peter Principle

by oneiria on Sep 26, 2017
Humor & Satire

The Summoning Dr. Catherine D'Great finally opened the door. "Sorry to make you wait, Mr. Crachit. I'm running a little late today." Robbie took in the elaborate furnishings of her office: A desk made of pure petrified wood, a wide consulting couch that appeared to be sleep number adjustable, and two lava lamps mounted on opposite walls. Above him loome...

Afro Stress Relief Ch. 04

by llts1970 on May 2, 2018
Transsexuals & Crossdressers

I didn't wake until 9am the next day which was late for me, I showered, shaved everywhere and put some jogging gear on, with a pink thong of course, and decided to go for a couple of miles run. I didn't want to put any weight on, I needed to be nice and slim for those Afro-studs; shit I thought why was I thinking like this, it was all getting very confusing....

Life as a New Hire Ch. 25

by FinalStand on Sep 18, 2017
Sci-Fi & Fantasy

*This story plays fast and loose with Ancient History and Linguistics; be warned* *Never judge a friend by what they give, but of how much of themselves they give* *Editing magic performed by KJ24 and Shyqash, plus contributions by the regular gang of brigands and neer-do-wells* *There is a bit of mangling of the Iliad going on. My apologies to Homer and...

It's a Wonderful New Life

by alexyzia on Sep 16, 2017
Transsexuals & Crossdressers

I met Sherry at a bar. Imagine that. I often picked up women at bars. I'm a good looking man, have a nice sporty car, cash flows freely from my pockets - at the bar anyway. So I do OK at snagging a tipsy babe for a nights folly. But all of the sudden karma has caught up with me. When I hit on her she told me to back off or I'd be sorry. When I persisted, pol...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

The Summer I Met Nina

by peacekeeper25 on Sep 11, 2017
Erotic Couplings

I met Nina the summer I worked as a waiter at Pocmont Lodge—a glitzy, somewhat seedy resort in the Pocono Mountains. It was a good way to earn a lot of money in ten weeks because we worked for room and board and got good tips. All the waiters and bus boys bunked in a cabin that looked more like a chicken house. The shabby cabin next door housed the band that...

Red Swallow Ch. 06

by RRswede on Apr 28, 2020
Transgender & Crossdressers

I was inspired to reach out to Barbara Jean Goodhead after reading her story, "The Diary of Jewel Delacroix" If you haven't read it, I encourage you to do so. I had an idea for a story, but have never published erotica, so asked if Barbara Jean would like to collaborate. Happily, she agreed, and the result has been this tale of Dustin's journey to becoming...

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...

Lady in Red Ch. 03

by Harddaysknight on Sep 25, 2017
Novels and Novellas

Gwen knew real fear as she looked at Mort's face and heard his intentions. She threw her door open and ran into the woods. She heard Mort curse and then the engine started. Headlights lit up the forest, forcing Gwen to flee farther into the night. She remained quiet until she was certain that she heard Mort drive away. She had the presence of mind to listen...