Sissy Surgery Stories

14,633 results
Orientation
Length
Source
Infinite Scroll

Feminized by a Black Thug

by Tinydickthongboy88 on Sep 25, 2017
Transsexuals & Crossdressers

I had been with my girlfriend since college. Somehow despite being a buxom blond she didn't mind my less than average size member or my slight slim stature, we're almost the same size. We were taking a big step now that we'd graduated, we decided to move in together. My girlfriend, Katy's parents gave her their condo in the north side of Chicago. The place w...

Making Himself Useful

by EasilyConfused on Sep 16, 2017
Transsexuals & Crossdressers

Don closed his motel room behind him, threw his car keys onto the bed and slumped onto the room's saggy couch. He was exhausted. It was the end of another frustrating day. He walked into the bathroom and ran water into a glass. He drank it down in two gulps and looked at himself in the mirror. He shook his head and poured another glass which he took into the...

A Conversation with a Lady

by OpenMouth on Oct 15, 2017
Transsexuals & Crossdressers

This story was inspired by Gemsissy and her wonderful shopping trips... ***** A select lingerie shop in a small northern English market town. The shop front reads 'Cherie.' I walk in and I'm surrounded by wonderful things by Lejaby, Aubade, Lise Charmel. A stylish woman is behind the counter; she's mid-40s, slim, blonde, tall. She has tanned skin, expe...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Explore the Inner Woman In You

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

I fancied the arse off a girl at school called Sharon. The problem was most of my year did. She was beautiful with long blonde hair, willowy legs, a butt to die for and stunning pert tits. She was way out of my league but quite amazingly we did get on and began to make slow but steady headway. My dizzy ambition was to ask her to the end of year college dance...

Trust Ch. 03

by kellyhockey on Sep 16, 2017
Loving Wives

Chapter 3: The Accident Mike went to work on Monday. Around 9:30 am Mike got a call from Jamie. Mike's voice mail system recorded the whole call. "Hey dick head. I am going to fuck your wife tonight. That's right Marine boy. I am going to butt fuck and then cum in her mouth." Jamie went on for about twenty minutes when Mike figured out where he may be call...

Mistress Treva Wins Again

by justincbenedict on May 29, 2018
BDSM

Dr. Shepherdson Grangerford milled about at the fundraiser, his adoring wife, Treva by him, the ultimate arm candy even after all these years. A balding, chubby fellow came up, grabbing Shep's hand. "Dr. Grangerford, everyone is so pleased that you made the fundraiser, and that you'll be heading up the Ophthalmological Wing. We probably couldn't have gotten...

Sandra and Stevie Ch. 47

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-seventh installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-six episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I str...

Sex Change for Black Boyfriend

by watersoda on Sep 14, 2017
Transsexuals & Crossdressers

I have an interesting story. I am now 26 years old. I was born a male but at the age of 23 I had a full sex change at the request of my boyfriend. Here is how and why it happened. I knew I liked men from an early age. I was interested to talk with girls and be their friend but I wanted men. I looked at men in the street, at their muscles and their penile bu...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...