Fattening Up The Sissy For Bull Captions Tumbex Imagefap Literotica Stories

369,658 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Wife's Exploration

by cpandy on Jul 5, 2009
Cheating Spouses

John sat in front of his PC trawling through Imagefap, his latest search for cuckold captions had uncovered a goldmine of unseen pics and his cock was stiff in his pants as he immersed himself in their delicious humiliation. He clicked quickly to those of a well built blond that paid a passing resemblance to his wife Doe. Stroking his cock through his pant...

Open in Reader

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...

Making a Sissy Jock Pt. 01

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

My life changed about a year after I was done college. I'm Mason, or I was and I used to be a football jock all through high school and played all through college and after all that I kind of just never got picked up. So...what do you do with a physical education degree? Most guys taught gym or coached some places. Me? I got a massage job at a spa. There...

A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

Open in Reader

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Finally a Real Sissy

by Parasissy on May 7, 2019
Transgender & Crossdressers

I have to tell you about the experience I had with my wife the other night. But first a little background for context. I have been married to my wife for over 10 years, I told her a little about my "adventurous" side before we got married, and I've slowly revealed more as time has passed. She tries to accommodate my Sissy desires, but truthfully she is not...

Crossing the divide

by reaper13 on Dec 3, 2016
Interracial

It’s all messed up. During the run for the white house tensions between races in the US have been escalating. Arabs are being profiled, Asians got accused of faking climate change, unarmed black men got shot by police, Mexicans have been called rapists and native Americans protesting in the freezing cold had water cannons used against them. What is this coun...

Open in Reader

Black Clover

by russellbeach on Apr 24, 2019
Fan Fiction

After a short trip John is walking inside the Magical Knights Colosseum towards the sound of people fighting. John has missed taking most of the Magical Knights Exam to help out a friend, as John entered the arena floor of the Colosseum he sees a man knocked out on the ground. in the stands above John a male voice starts speaking "If there is anyone who...

Open in Reader

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...