Sissy Pimp Stories

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Orientation
Length
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Infinite Scroll

My Mistress Ch. 03

by Kandy5647 on Sep 12, 2017
BDSM

Hello Peoples of Literotica! It's Drew Nelson again! And I'm back in full force! This time I'm here to not only tell you about my stunningly gorgeous Mistress Tameka. But! I'm here to tell you about my new Master Quentin Devonté Sterling as well. My God what a man he is! Wait! What am I saying?! He's a pure bred God! He's this 6'6, 210lbs, dark brown eyed,...

The Road From Ojai Ch. 03

by Angelscuck on Sep 15, 2017
BDSM

Angel quickly opened one of the packages and unwrapped a strange device which looked like a small penis- garter and placed it around my dick. Then she put another attachment around my balls and up my ass. She handed the remote control to Michelle, who then handed it back and said, "Show him what happens if he should hesitate performing any of our demands....

Adult Arcade Sissy

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

Dwayne started hanging out with us when I was 18. He was older than us - 28 - but he came across as someone our age. Because he was older a lot of us guys sort of hero- worshipped him - me included. So naturally I was flattered when he began to spend a lot of attention on me in particular. The guys I hung out with were a little wary of Dwayne, because he w...

Hazardous Waste Ch. 02

by NOIRTRASH on Sep 16, 2017
Loving Wives

All characters are adults. When I got outta the air force I needed a job but didn't wanna slave for a dollar forty minimum wage, so I got some business cards printed, and tacked them to bulletin boards around town. I got outta the air force with most of my mechanics tools, bought more, and bought an old Chevy pickup. I became a handyman. Calls came in alm...

Futanari Academy Ch. 14

by TheOrcKing on Jun 10, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Halloween Special, 2018 Danielle walked up the steps to her friend Maddie's house, still wearing her Westbrook school uniform which now consisted...

Mistress Red Fox Becoming a Devotee

by His_fag_wife on Sep 24, 2019
BDSM

A story of what might have been a dream. Names have been changed. *** One evening I was looking through profiles on a BDSM website and came across one for a local Mistress, she was developing a new dungeon and she was asking for suitable subs for her to try it out on. Someone to test the new equipment and layout on. I read the ad over and over again, this...

Sissy Whore Ch. 01

by DebbieDublin on Mar 7, 2018
Transsexuals & Crossdressers

I suppose it started as a game really. Born out of the frustration and boredom of countless meaningless encounters with nameless men from chatrooms who would call to my house late at night. Although each proclaimed themselves to be dominant, still none seemed to live up to my own expectations, leaving me drenched in their seed but ultimately unsatisfied. It...

Young Master Ch. 04

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"I can explain..." I was standing in a French Maid outfit, with a sissy's cum still dripping from my chin because as usual she missed a spot, and I had just been caught bent over a desk getting pounded from behind...all I needed to make it the perfect shit storm was for Dale to notice my cock was stick disturbingly hard in my panties for some mind boggling r...

His Breeding Cow

by SWGirl on Sep 12, 2017
Interracial Love

(DISCLAIMER: If you're not a fan of interracial sissy cuckolding, go no further. Don't bother with the righteous indignation or the crude comments. Celebrate why you're here in the first place and move on.) "He said he wants me off the pill, he's going to breed me Tony!" "What!" I said. "Jenna, he can't do that.... You can't do that. You're my wife." I w...

The Perfect Age Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It wasn't long after I became his lover that he had me seeing other men. The first time was at a party he took me to several months after I started seeing him. He had me go down on a friend of his while he watched. Assured me all was okay, it would be 'safe'. 'Just do it, you'll do that for me, baby, right?'...I did. I actually enjoyed it. I found out early...