Sissy Pimp Stories

9,288 results
Orientation
Length
Source
Infinite Scroll

Maid to Surrender

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

When Mr Hastings first phoned me, I had no reason to think he was anything other than an ordinary client. I mean, so what if he asked me to turn up dressed as a chambermaid? That was one of the options mentioned on my business card. Transvestite maids have always been popular... My maid's outfit was the flimsiest kind; really just a cheap black mini-dress w...

Sissy's Sexy Strut

by nancyvasquez on Aug 28, 2018
Transsexuals & Crossdressers

Last night kicked off the Labor Day Weekend, so I decided to do something daring -AND, very sexy, too! I was looking at myself in the mirror yesterday afternoon & checking out the effects of the beating I got from Mike the other night. My eye is still pretty much closed, and now it's all purpled. My upper lip is still puffed out too, but I think it looks dam...

Groomed to Depravity Ch. 06

by ssamlee2000 on Sep 14, 2020
Transgender & Crossdressers

It was Mohamed's birthday today. In exchange for having "skipped on the job" on Saturday, I was to be the "entertainment" tonight for the party. I had my term exams this week, but I wasn't exactly in a position to say no. I'd already fallen so behind on the materials due to my weekend duties, I doubt one more night of studying would've helped me anyways. I...

Sandra and Stevie Ch. 52

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the fifty-second installment in a series entitled "Sandra and Stevie". If you have not read the previous fifty-one episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stro...

AliExpress and Sissy Downfall Pt. 10

by His_fag_wife on Jan 23, 2019
Transgender & Crossdressers

As Charlie with her head raised off the cushion admired her new sissy pussy, she felt a complete head rush. As she and Tim had discussed just one guiche piercing at such length, over and over, texts flying back and forth on the crest of a wave of horniness and a submissives deep desire to please, she had fixated on the idea of being pierced without her wife...

The Story of Babygirl Ch. 01

by nafyssis on Oct 15, 2018
Transgender & Crossdressers

I'm nervous. I have never been in a porno movie before, but today this is going to change. One of my clients hired me to be a star of his private movie. My pimp, Joe brought me to the place where the shooting will happen, in an old factory building outside of the town. A staff member led me into the dressing room, and ordered me to put on the things I will...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Steph and Giulia Ch. 01: The Betrayal

by BigHand32 on Sep 16, 2017
Fetish

Giulia was going to be at the party. Stephen still wanted to see her, even if she had betrayed him. Every day, he had given her a ride to school. Every day, he had been there for her. She laughed at his jokes. She smoked his weed. Now she had betrayed him, but when she invited him to the party, he couldn't help but go. A week ago, he had finally got her to...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...