First Pegging Stories

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Orientation
Length
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After Party Truth or Dare

by 4EyesDawn on Sep 17, 2014
Group Sex

You and your friends just spent the last couple hours at a party that turned out to be pretty lame. It's a Friday night and you've all had a couple drinks and want to have a good time so you all head back to the house several of you share to keep the party going.What's next? Male Female What's next? Male Female...

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Put That On!

by johnson69 on Sep 16, 2017
BDSM

It was a confused response when I first told her I was bi. We had only been together for a short while, yet as the affair escalated, I wanted to be certain she knew who I was, what was my past. I had already told her about the large baggage I had to check, so to speak, but this was my carry-on bag, which would certainly be important to know about as intimacy...

Thirsty For Somali Girls

by Samuelx on Sep 12, 2017
Erotic Couplings

Every man who has ever lived has a weakness. The man who disagrees is a bold faced liar. My name is Samuel Chambers and I was born in the City of Montreal, Quebec, to a Haitian immigrant father and a white Canadian mother. I consider myself as Canadian as anyone. I got a story to share with you, ladies and gentlemen. I want to tell you about how I met my wif...

Ness "Does" Judo

by PB2019 on Nov 12, 2019
Group Sex

Ness had made sure the sports bra she had on didn't have any padding in it. She knew this would allow her nipples to show through if they got hard, which they normally did in class. She also knew Jack might notice if her nipples got hard, the thought of it made her quiver. As she got to the gym she only saw another 2 cars outside. "Must be a quiet night...

Pegged

by ndeavour on Sep 25, 2018
Erotic Couplings

I was home alone in my office. One of the benefits of working from home is being able to dress as I please. Since I had a video call to deal with, from the waist up I had on a dress shirt and tie. But from the waist down it was a pair of board shorts. My wife Alison had gone out earlier for lunch with her girlfriend, Geri. Alison is a real knock out, and I a...

My Shy Neighbour

by Ozgal on Sep 14, 2017
BDSM

Marty was such a sweet guy, but so painfully shy. He’d moved in next-door 3 months ago and in all that time had uttered no more than a couple of words and only when I spoke to him first. He had this cute little way of dipping his head into his shoulder and never making eye contact. Marty was quite a handsome man. He was about 6’ tall, with dark blonde hair...

The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

Create a Shemale

by wsauthor on Sep 29, 2018
Science Fiction

*Author’s note: This story is Public, if you have an idea, start writing!* Robots, science and chemistry have all advanced further than the public is aware of. Due to patents and trade secrets, nobody knew it was even possible to create a sex bot. They can have gravity defying shapes and sizes. They can even alter their owner with chemical cocktails. Cockbot...

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My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

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...