Sissy Pimp Stories

9,288 results
Orientation
Length
Source
Infinite Scroll

He Looks Like His Father

by RainStevens on Sep 13, 2017
Interracial Love

WARNING! This fictional story isn't for everyone. It involves cuckolds, male feminization, submission, interracial sex and breeding. If you're not interested, go find another story. * I am a white fifty something year old married cuckold and a proud member of the W.B.A. My wife is twenty years younger than I and we have four children (with one on the way),...

From Business Owner to Prostitute

by Kellycumslut on Dec 2, 2019
Transgender & Crossdressers

How things have changed. From respected business owner to insatiable street prostitute. For a long time I ran a very successful business in London employing 14 staff and loving my work. I worked six days a week and on Sunday I did the paperwork, wages and stock checks. I had no time for social life, I was working for a successful future and in the evenings...

Tonight, You Will

by trixie_leigh on Mar 3, 2020
Transgender & Crossdressers

Yes, you should be on your knees for this. Definitely. That's what you like isn't? To serve me? To submit? To be my little bitch? You look awful cute in that chemise, although it does keep falling down your left shoulder doesn't it? Too bad you don't have actual tits to hold it up. That's okay, we can pretend. I mean, I know you pretend all the time. But I...

Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...

Afro Stress Relief Ch. 06

by llts1970 on Dec 12, 2018
Transgender & Crossdressers

I was running a bit late after I'd overslept my alarm clock, my shift at Missy Bee's and the hard riding I got from Leroy must have tired me out more than I thought. I managed to get into work just on time, once there I rang Sarah. "Oh hi Johnny, sorry I mean Tina, wow it's early," Sarah lazily answered. "Hi Sarah, is Marci OK? I can pick her up this eveni...

Satan's Sissy

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Oh you stupid little faggot! You just had to go and get married to a woman! Why?? Why fuck up some poor girl's life like that? Was it because you crave humiliation, and subconsciously you knew it would be just a matter of time before you got caught, and you would be outed publicly? Outed as a pole smoking homosexual who was more at home in frilly skirts and...

Professor to Sissy Slut

by sdbottomslut on Sep 14, 2017
Transsexuals & Crossdressers

I had just turned thirty-four and I was miserable. My wife of twelve years had left me for another man and was living with him. We were not yet in the process of filing for divorce and I was hoping she would have a change of heart. I was still in love with her but I understood why she had left. We had grown distant over the previous few years and we rarely h...

Sissy for Satan!

by nancyvasquez on Jan 14, 2018
Transsexuals & Crossdressers

Oh you stupid little faggot! You just had to go and get married to a woman! Why?? Why fuck up some poor girl's life like that? Was it because you crave humiliation, and subconsciously you knew it would be just a matter of time before you got caught - and you would be outed publicly? Outed as a pole smoking homosexual who was more at home in frilly skirts and...

Unknown Waifish Model Ch. 01

by Couture on Sep 12, 2017
Transsexuals & Crossdressers

We lay curled up to one another in the hotel bed, Sandra and I. I looked forward to the day we'd no longer have to make do with hotel beds and the occasional foray to my apartment. Yes, one day soon, she would leave her bastard of a husband and move in with me. God, she was beautiful. Her blonde hair was mussed up, as she lay on the pillow. Her face had th...