Tricked Into Sissy Stories

348,985 results
Orientation
Length
Source
Infinite Scroll

A Sissy's Tale

by kurrginatorX on Feb 25, 2019
Transgender & Crossdressers

There were two full armloads of stuff remaining, but he thought if he could position everything just right then he should be able to take it up in one final trip. He was successful in loading it, but now he couldn't shut the back hatch. Just then, a voice called out from behind him. "Hey. Hold on there, friend. Let me give you a hand." The mystery man took t...

Female Erotic Police Squad Pt. 07

by mattpantyhose on Feb 13, 2018
Fetish

I would like to thank Georgia Alice for all the help she offered. Most of the characters and places got their names thanks to you. Your assistance with the English language allowed me to move forward with the work, when I could not find the proper word. And above all, being my most faithful reader, you mobilized me to continue the writing. This story would h...

Thirty Days to Jenny Ch. 2

by monika ikon on Sep 12, 2017
Transsexuals & Crossdressers

day eleven Well, Alison, thought, Jeff had been listening to the 30 Days to Jenny tape for ten days already and the changes in his character were dramatic. He was sweeter, more helpful around the apartment, and even more satisfying in bed. He'd started a diet, been exercising, and had taken a renewed interest in his appearance. If the changes stopped there,...

A Harmless Favor

by SissyJon on Oct 3, 2017
Transsexuals & Crossdressers

It began as a harmless favor; I had no idea that it would change all of our lives. My wife's college roommate and her husband had moved into our community and were soon dominating our social life. We were just three years out of college, but both couples had done quite well - so well that we had bought a nice suburban home in the southwestern city last yea...

Double Wedding

by Tomsparty on Sep 18, 2017
Transsexuals & Crossdressers

I was about to marry my childhood sweetheart Paula Rother. I loved her and she loved me but it hadn't been straightforward. After school she went to Manchester University while I went to work at a local accountants as a lowly paid junior clerk. She said we where inseparable but during the two years she was away she met Graham. I was heart broken and knew I w...

Topped from the Bottom

by cutebabysadie on Sep 14, 2017
Loving Wives

I have always been a stud. It was nothing new to me, it was just who I was. I remember, when I was little I ran the playground. In middle school, I was the only one dating a girl in High School. And in High School, I dated the prom queen and was a star in 3 different sports. I got a full ride to college and beat out a senior college quarterback to become the...

A Busy Day Pt. 01: An Oral Surprise

by nadia603000 on Oct 6, 2020
BDSM

Author's Note: Mistress Pepper and Sophie are "anonymized" versions of me and my slave-girl. The real me. All of my stories are (or should I say will be) my memories of a session with a sub. Thus, they are true stories. Only in this version details have been changed to protect the sub. I do live in Mobile about 10 months of the year (the remaining two I spe...

Fantasy Ch. 01

by necromonkey84 on Sep 16, 2017
Novels and Novellas

So, one day my wife, Kathi, asked me to write her an erotic story. I have always been good with words and have many sexual fantasies; however it is sometimes difficult for me to put these fantasies down on paper. The truth is, the reason I have such detailed fantasies is because other than my wife, I don't have much experience with sex at all. We have an ope...

Bi Cuckold Humiliated and Fucked Ch. 03

by DaveLoveAss on Dec 16, 2019
Fetish

Part 3. If you haven't read the first one you should do that and learn how the cuckolding began. People keep asking for more so here it is, the second night... * Work that day was long and painful. Every step was a gentle reminder of the pounding Abe had given me the previous night. Every time I sat down was excruciating as my ass never seemed to fully clo...

Sailor Moon Ch. 03

by embarrassednakedmale on Apr 21, 2020
Transgender & Crossdressers

[In "Sailor Moon: Ch 2", Scott took a few faltering steps down the path to being a sissy at the hands of the Master. Having barely held his nerve to beat another aspiring sissy - Robert - in a test of daring, Scott has now been named "Serena" by Master, who has left Scott at the deserted rest stop by the motorway dressed in his red Sailor Moon outfit. While...