Pegging Punishment Stories

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Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

The Gentlemen's Panty Club Pt. 05 - Final

by joefelton on Aug 22, 2018
Fetish

Authors note: This is the fifth and final part of my story, and I believe I have saved the best for last. Thank you to those of you who've read the first four parts. For those readers who are new to The Gentlemen's Panty Club, I have included a short cheat sheet in this note, listing the major characters and a few significant details about them, that should...

1st Meeting with Mistress Pandora

by FiguringItOut23 on Jul 10, 2018
Loving Wives

***I am over 18, as is everyone in this story. I'm actually 23*** *** I felt it before I ever met Christina. The overwhelming desire to serve, to drop to my knees and submit to someone's will. The impulse to sacrifice or delay my own needs to satisfy another's. It was a powerful urge, and when I saw her across the bar it was immediate and it was viceral....

Black On Black Pegging Rules!

by Samuelx on Sep 11, 2017
Group Sex

Happily I slid my eight-inch strap-on dildo into Saul Jean-Pierre's tight asshole. The big and tall young Black man groaned as I penetrated him. Lying on his back completely naked on my big bed, he took it like a bitch. Bound legs hanging in the air and eyes filled with lust and shock. His hands are also bound for good effect. I wonder if he knew what he was...

Would You?

by Dragonologist on Mar 13, 2018
Toys & Masturbation

Would you? This question is being asked because, a week ago, we received a message on Facebook saying we should check our email for instructions because our lives were about to change. Normally, I simply dismiss random messages, like this, from an online person who I don't know, but the name that showed up was Mistress Trudy. It's the same name my wife use...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Made to Obey Ch. 07

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Lisa: My Ass is in for a Long Night

by TrazO on Jul 6, 2020
Anal

A week ago Lisa had hung me from a hook and more or less savaged me, leaving bruises, hickies, bite and lash marks all over my torso, and my muscles fatigued and sore. The third day after, while I was trying to find a position in bed that wasn't painful, she came in naked, with sad eyes. She pulled the covers back and looked at my marked body. The bruises we...

Black on Black Pegging: Muslim

by Samuelx on Sep 11, 2017
Fetish

The root of all problems in the Black community isn't the White man. Black people have got to stop playing victim and accept responsibility for their actions. My name is Christina Xavier. A tall young Black woman living in the City of Ottawa, Province of Ontario. I hold a Journalism degree from the University of Toronto, and presently, I'm doing an investiga...

Black on Black Pegging : Toronto

by Samuelx on Sep 11, 2017
Erotic Couplings

A lot of Black guys have this image thing where they act tough and talk even tougher. For a lot of them, it's their way of dealing with a world that's hostile to them. As a Black woman living in the City of Toronto, Ontario, I can definitely relate. Canada isn't always friendly to minorities, especially those of us who happen to be of African descent. I was...