Literotica: Sissy Boyfriend Takes Dick Stories

194,409 results
Orientation
Length
Source
Infinite Scroll

Me & Mary-Kate Olsen

by sex_master on Sep 17, 2017
Celebrities & Fan Fiction

One sunny day I am out for a walk in the park by my house. I come upon this couple that seem to be having an argument. I sit down and listen to them for a few minutes. The girl starts to hit the guy. The guy hits back. I walk up to him and say to him that he should not be hitting ladies and knock him out cold. I then realize that the girl was Mary-Kate Olsen...

Daydream Whore

by maya449 on Sep 14, 2017
Loving Wives

When I was a young girl my recurring daydream was that my boyfriend comes by my home late in the night and drives me to a party. After walking from room to room and outdoors, I suddenly know I am the only girl there. My boyfriend holds my hand and pulls me to the grass next to a pool. The backyard lights are bright. He places his hands softly around my neck...

I'll Show Him

by curious_shape on Sep 13, 2017
Erotic Couplings

For an hour or so the same email was open on her screen. No matter how many times she read it the message hadn't changed. Her best friend had sent her soon to be ex boyfriend an email saying 'I missed you last night. I can't wait until you're inside me again. And again. And again!' The email had been sent to her and not her boyfriend and the more she tho...

June's Essay

by Heironymous on Sep 14, 2017
Group Sex

I teach night school at our local Community College for extra income. One of my students, June, is very intelligent, but has had a very difficult life so far. I took a special interest in June, and in an attempt to assist her in realizing her potential, I asked her to write a story about something important that has happened in her life and has contributed t...

Aretha - English Version

by Scorpio58 on Sep 14, 2017
Erotic Couplings

WARNING: English is NOT my first language - I have learned it in school and practiced it a lot in trading, but this is (even though pornographic) supposed to be literature. So please bear with me, or, if not, just read something else. I also need to mention that the story is true, depicting my personal memory. All the names and/or places may have been cha...

Jillian's Sexual Awakening

by Edge248124 on Aug 22, 2018
First Time

"Ughh!" Jillian tosses her phone to the side of the bed in frustration. With a discontented sigh, she stands and walks to her mirror. "I'm just over this." She grumbles to herself as she fiddles with her hair. Her boyfriend crosses her mind, and she feels a pang of contempt towards him. She just wasn't happy these days ... Jillian was attracted to him at fi...

Aretha

by Scorpio58 on May 7, 2019
Erotic Couplings

WARNING: English is NOT my first language - I have learned it in school and practiced it a lot in trading, but this is (even though pornographic) supposed to be literature. So please bear with me, or, if not, just read something else. ***** I'm on the verge of kicking some ass... It's a summer day, at noon, when most people are either at work, either at...

Familiarity Breeds Interest Ch. 02

by orie on Sep 12, 2017
Exhibitionist & Voyeur

Anne Marie, Becky and I were excited to go to Rita's birthday part. The girls kept teasing me about Anne Marie exposing me to Linda earlier. Becky asks if I will be embarrassed to be around her tonight. I said I could handle it. None of us mentioned the blow job Becky gave me in front of Anne Marie, but I also didn't pick any awkward vibes and so I was not g...

How my boyfriend became a stallion's slut

by User1100 on Apr 22, 2025

My boyfriend and me are live together on a ghorse ranch and take care of several types of horses; young ones, old ones, jumping horses, draft horses and so on. They are high intelligence horses, who can express themselves though facial expressions and gesture. It‘s a special language, which my boyfriend and I learned to unterstand and interpret. Thereby we c...

Open in Reader

My Sexuality Ch. 04

by TheOriginalAnonymous on Sep 13, 2017
Reviews & Essays

A blend of what I want in a relationship, my relatively unique brand of cuckolding - and the motivation behind why I want it that way - and how I wish there were more stories in erotica and in porn like that. It seems to me as if the cuckolding genre tends to be so narrow, the elements of it terribly lacking in creativity. Now, some people like the cliched...