Sissy Pimped Stories

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Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

Pimped Out White Sissy!

by nancyvasquez on Sep 16, 2017
Anal

Hi everyone! I haven't posted in a while, but I definitely have been having a lot of experiences. Best news is that I found a new adult bookstore to hang out in! I found out about if from a guy who I gave a blow job to in SECRETS in Jack London Square in Oakland. He asked me if I'd ever been there, and I told him I'd never even heard of it. It's a place call...

Making of a Sissy Whore Ch. 03

by SecretAgentFun on Oct 21, 2019
Loving Wives

Pimped Out If you haven't read the first 2 chapters, it might be a good idea so that this makes more sense. Your call, and I hope you enjoy either way! *** Jeff stepped off the bus feeling defeated as he walked the five blocks back to Brad and Kayla's place. He couldn't even think of it as home now, since Kayla was sure to kick him out tomorrow. He was jo...

White Gurl Pimped in the Hood

by Stephisissycd on Sep 11, 2017
Group Sex

After Black Mike made me his bitch, showing up at motels all over town dressed like a street hooker, he sent me a text one day. "Hey bitch. I need you to dress really slutty, get smooth and totally clean, and meet me at the motel at 6th and Los Angeles st." I knew where that was, right by skid row. My pussy started to throb thinking about what black mike h...

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...

Wife Turns Slut For Husband Ch. 02

by Dirty Slut on Sep 26, 2017
Group Sex

The Worm Turns Intro: As you remember in the last saga my husband had begged me to turn him into a cuckold. As things turned out I found out that he wanted to see me fucking other men, and not just any men, but black men with big black cocks. It was a torturous decision for me, but as I loved Billy so much I finally made contact with a black man on Billy’s...

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,...

After Bar 69

by Nudemodel on Sep 2, 2017
Interracial Love

"After Bar 69" is the second story in a series of four. It is drawn from experiences of a white American male nude art model, Tom, from Cleveland. He becomes a dirty naked sex-model publicly engaging in sex and rimming a naked black Jamaican female, Angela, in an open-to-the-public live-sex-peepshow on the Reeperbahn in Hamburg, Germany. Characters and place...

A Mistress to Obey Ch. 02

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm and gay play. Not your thing, move on. * I can't stop thinking about what happened last Saturday. It was so much more than I expected, and frankly, I did things I never thought I would do. I had fantasized about forced fem but still was surprised how different I felt when in panties. It's just hard to feel very masculine when in a...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...