Sissy Pimp Stories

9,288 results
Orientation
Length
Source
Infinite Scroll

Swagged Out with My Cock Out

by DickThePimp on Feb 12, 2019
Celebrities & Fan Fiction

Swagg Pimpin' Sex Parody On the patio outside my penthouse suite at the Beverly Hills Hotel. Lighting a blunt. Smoking, looking at the pool party downstairs. All nude and shit... swaggin'... hangin' 10 thick. Hands on the rail, smoke in the air. What's next Dick? What about those lame ass hoes that talk shit on Literotica? Who's gettin' swagg pimped next?...

Pimping Angel

by Angelscuck on Sep 16, 2017
First Time

"Oh, here's something interesting," my fiancée Angel said, browsing through the throw away paper calendar. "A local strip joint is having a Pimp 'N Ho Party Saturday night. Bikini dancers, good food, music and live entertainment and customers are encouraged to dress up as pimps and whores. Sounds like our kind of party, interested?" "Sure, why not?" I repli...

Review: Gun Shy

by velvetpie on Sep 16, 2017
Reviews & Essays

Women: Stories of Passion. Gun Shy. Starring Anneliza Scott (as Penny), Tony Ervolina (as Billy), James Black (as Cop), India Dupre (as Young Girl) and Elisa M. Rothstein (as the Interviewer). Lonely lady cop meets an attractive pimp. * * * * * Penny is sitting in her car, waiting for the Interviewer and when she shows, she invites her in. Penny asks if...

Ella's House of The Way Forward Ch. 12

by Sputnik57 on Sep 18, 2017
BDSM

Minter's cock bulged in its strange and tortured position, pulled between his legs and his bell-end teased by the foreskin rings as his gait was enforced to one which matched his feminine appearance. The three women taunted him mercilessly as he sat precariously on the cab seat, perched on the edge as each movement vibrated through his balls which he now hal...

Sexual Olympics 2010

by Bakeboss on Sep 1, 2017
Humor & Satire

"Good evening folks and welcome to the twenty-third Sexual Olympics. My name is Brice Carlson and we are here in beautiful downtown Bangkok. Allow me to introduce my partner Richard 'Tiny Dick' Johnson." "Brice it's wonderful to be back here in Bangkok, the place where it all started. I know I have many..." "Sure, that's great Tiny, well folks we have a w...

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...

Son of a Cuckold Ch. 01

by shem802 on Sep 13, 2017
Interracial Love

DISCLAIMER: This is a work of erotic fiction which features interracial sex, cuckolding, prostitution, son-mother voyeurism, humiliation, violence, and pimping. If any of these things are not to your taste please feel free to stop reading at this point. * I was 18 years old when I first became aware of my father's gambling problem. Throughout my childhood...

Kathy and Manny

by BJB69 on Jul 6, 2020
Erotic Couplings

Manny was always a good looking kid. His Mother had named him Manuel, but his classmates dubbed him Manny in the first grade. His Mother was second generation Mexican and his Dad was second generation Guatemalan. He was just under six feet tall and weighed 184 pounds. He wasn't muscular in a weightlifter body style, but more of a swimmer or soccer player bod...

The Reunion Ch. 02: Thai Massage

by Valtikka on Jul 15, 2020
Anal

"Krissy! Long time no see! It's so good to see you. You look great girl!" As soon as I get out of the Uber, Micky comes walking to me with wide open arms and gives me a big hug. "Come let me help you with your bags. You're the first one to arrive so you have first pick on the rooms. The rest of the gang will arrive tomorrow." Instead of the overalls I'm use...

The Receptionist and the Zombie

by SikFuk on Sep 13, 2017
Erotic Couplings

edited by Asylum Seeker Grant never was much of a partier. He was even worse with women, but Jane, the new receptionist, was different. Her gap-toothed smile, her corn-fed physique, her frumpy outfits gave her an air of approachability that bolstered his confidence to the point where he actually got up the nerve to ask her if she'd like to go to the office...