Sissy Pimp Stories

9,288 results
Orientation
Length
Source
Infinite Scroll

Casual Kink - Jennifer Ch. 05

by ShortStoryteller on May 4, 2020
Fetish

"You'll just have to swallow it?" "No way...fuck you! I'm not doing that!" I say looking up at Sam as I continue to stroke him in slow rhythmic motion. My thumb nudging underneath his head every time my wrist slides up causing him to twitch in excitement. I also make sure to caress his balls every time I slide my wrist towards the base of his pretty cock. T...

Abducted and Turned Out Ch. 04

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

I let the landlord in and he immediately pushed me over the arm of my sofa and yanked my skirt up and pulled my panties down. I moaned and purred while he plunged his cock in and out of my pussy, fucking me furiously for about 5 minutes until he filled me with a nice hot creamy load. Then, without a word, he zipped up and left. I stayed there for a couple o...

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

Oh Crap!

by Zeb_Carter on Sep 12, 2017
Humor & Satire

This is a repost of a story I submitted as zeb1094. It has been edited slightly from the original and is being reposted under my new screen name. This is an original work by Zeb_Carter and is protected under copyright by U.S. copyright law. It is only submitted at Literotica.Com and any submission to any other site has not been authorized by the Author. I...

Afro Stress Relief Ch. 08

by llts1970 on Nov 11, 2019
Transgender & Crossdressers

It was Monday evening, again, and I hurried home from work to get ready for my shift at 'Babes With Asstitude' (BWA). My new Afro-boyfriend, Drake, rang to chat about our new venture as soon-to-be Brothel-keepers and tell me not to work 'too hard' on my shift as a whore at Drake's uncle, Leroy's, place, BWAs! Drake wanted to come over but I said I wouldn't b...

Jailhouse Faggot

by nancyvasquez on Oct 14, 2017
Anal

Before I got sent to the joint I spent over 6 months in county jail. The jail was old and they had old fashioned cells with bars. The cells were small, 4 bunks in each cell. I had never been in jail before and I was scared and it showed. I was young, slightly built, and timid as hell. The cellblock I was housed in was on the 4th floor. There were two sides...

Sissy Whore Ch. 03

by DebbieDublin on Mar 12, 2018
Transsexuals & Crossdressers

I woke to the sound of my cell phone vibrating in the other room. I had no idea how long I'd been asleep there on the bathroom floor. It was still daylight but I felt colder. Jumping up from the floor and running into my bedroom to reach the phone before it stopped ringing, I caught a glimpse of my ruined face in the mirror which was still stained with strea...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Afro Stress Relief Ch. 11

by llts1970 on Oct 5, 2020
Transgender & Crossdressers

At work on Monday, things were once again running as usual, no one mentioned the Beer Bust, well almost no one, Mary cornered me when I was getting a coffee. "Would you like to know what I did this weekend?" Mary asked coyly. "Er...yes sure," I answered, trying to sound completely uninterested. "Well, I was recruited by a black pimp! I'm a real prostitute...

Bambii's New World

by mikhaylacumme on Sep 12, 2017
Transsexuals & Crossdressers

My mind was racing the whole time. I couldn't believe where I ended up. But the sensations were running through my body. A 9-inch cock was ramming my boy pussy as hard as it could. Another cock, at least 10 inches, was being forced down my throat as his hands wrapped around my head, forcing me to deep-throat his amazing piece of man meat. Once he allowed...