Pegging Boy Stories

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Paul & Liz Ch. 02

by Metropolman on Sep 14, 2017
Fetish

'I need to go shopping today; will you come to the Mall with me?' Liz asked. Today was Tuesday and Liz had the day off, as I work from home and set my own hours, we were both free. At first we drifted aimlessly around the Mall, mostly window shopping although Liz did buy a new pair of jeans for herself. We took an hour off for a pizza lunch and I suggested w...

Anal 101: How To Get Pegged

by Tigger_Lilly on Apr 3, 2019
Anal

[Bonus Turn On Trick: If you are dying to have a woman peg you, you may want to start very, very slow. Even a kinky woman may resist anal. Sharing a story like this can be a great way to start talking about your fetish.] Anal 101: How To Get Pegged I'm not sure where the desire came from. Maybe porn? Maybe. The idea of having my butt penetrated seemed to...

My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...

Kinky Tales: I Pegged my Husband

by silkstockingslover on Sep 16, 2017
Anal

Summary: Wife's discovery of husband's anal toys changes everything. Note 1: This is a Halloween 2015 Contest Story. Note 2: This is one of two different versions of this story; you can read the husband's much shorter version called Kinky Tales: I'm Pegged By My Wife. Note 3: This is dedicated to: The real Chris and Dani who this fantasy is written abo...

Jason's Secrets Exposed Ch. 10

by jlenil on Sep 13, 2017
BDSM

I would appreciate if readers would rate and comment on this chapter. ***** Lillie and I had had a wonderful time, and I was enthusiastic about what a great pupil of perversion she had turned out to be. After Jason served us our breakfast, Lillie and I had our cigars on the patio and, afterward, she got ready to leave. She had a wicked glimmer in her eyes,...

Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

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Who's the Boss

by Shady_Lady on Sep 15, 2017
Fetish

Have had many chats over the past few weeks and femdom seems to be a popular theme with many guys. My thanks goes to so many of you for your ideas but in particular to Master Kink who helped a lot with the plot development. ***** "Andy I'm home" said Jenny from the front door as she dumped her heavy briefcase on the sofa before throwing the jacket from h...

Cumming of Age Pt. 04

by Mikehawk2187 on Feb 10, 2020
Group Sex

NOTE: (This story contains guy on girl sex as well as guy on guy sex. if you aren't into that sort of thing then you should probably not read this story) * Ever since my pegging experience with Liz, her and Terry have been keen on playing with my ass a lot. Every time Terry sucks me off now she likes to put a finger in my ass. Of course I don't mind this,...

A Second First Time

by Mysterious_D on Sep 12, 2017
Anal

"I'm ready!" I exclaim, strutting out of the bathroom. I'm nearly naked, save for the mystery item I have just adorned. I appear as a silhouette in the doorway, and you admire my slender feminine figure, tracing the shape of my hips with your lustful eyes. Slowly, I turn to the side, showing you the outline of my pert breasts, my flat stomach, and my little...

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...