First Time Pegging Stories

351,034 results
Orientation
Length
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Infinite Scroll

The Night That Changed My Life

by Anyport on Aug 18, 2017
Fetish

Let's get one thing straight right from the start, I am absolutely devoted to Tina. In fact, if you'd asked me three months ago where I would most like to be in the future, I wouldn't have hesitated in answering, 'With Tina hopefully living together'. I would not, however, have included the fact that I would be.... But maybe I'd better start at the beginning...

Bye Bye Virginity

by Otazel on May 4, 2020
First Time

BYE BYE VIRGINITY. It had been eight weeks since Kyle had celebrated his eighteenth birthday and so it was eight weeks since he had promised himself that now was the time to get rid of his unwanted virginity. But in those eight weeks he had not made any progress in that direction other than managing to get a quick grope of a girl's breasts at his birthday p...

Nicholas and Linn Ch. 01

by WilloLinden on Sep 26, 2017
BDSM

This is a story about a couple in a D/s dynamic finding out who they are with growing elements of Ageplay, or specifically, a Daddy Dominant and Little dynamic. All characters are consenting adults. The main character is based on me; I started this story for a friend but was getting some great feedback from other friends who encouraged me to share. Construc...

Timeros: A Clash Of Gods Ch. 03

by TravellingWilly on Sep 15, 2017
Sci-Fi & Fantasy

House of Dianna, Mountain Of The Daemon's Once the gates had closed behind them, Cazadora let out a long sigh and her whole body sagged, her hands went immediately to her engorged stomach. "I thought that fool would never leave," she said through gritted teeth she reached out and two of her personal priestess' took her weight on either side. "Get me to my c...

More Oral After the Exam Ch. 01

by gradprof on Sep 13, 2017
Erotic Couplings

After a long hiatus, I decided to start a second part to my "Oral Exam" storyline. I just miss the dirty stories too much.... This one picks up one semester later. If you haven't read the first series, I'd suggest that you stop here and go back. Don't worry! It has naughty bits too. Thank you, thank you, THANK YOU to Mykittystar for editing. I deeply appreci...

Finding my Place

by Lost_Yonder on Sep 17, 2017
Mature

It was the late 1970s and my senior year of high school. Since moving to Denver three years earlier, I had lived the life of a monk, or more in tune with the times, a nerd. We moved to the city from a rural community in Kansas, a farming community. The population of the entire town was equal to the number of students in the Denver high school. There I was Mr...

Protecting Amanda Clarke

by MTL17 on Aug 31, 2017
Celebrities & Fan Fiction

Author's note: This story takes place during season 2. *** The woman who called herself Amanda Clarke stared dumbfounded at her TV screen, unable to believe what she was hearing. It was true it might mean this nightmare was finally over... or it was just beginning. It all depended whether Emily Thorne, a.k.a. the real Amanda Clarke had done this, and if s...

The Mysterious Mrs. Sang Beneficary

by SpencerAlanMacLeod on Sep 13, 2017
BDSM

The Mysterious Mrs. Sang – Beneficiary Forward This is the second in my Femdom series about "The Mysterious Mrs. Sang". I thank all of you who so enjoyed my first story featuring her. Thanks to you, at the time of this publishing, it is the most popular story I have written. This tale features the same protagonists as the first. I hope you are as aroused...

ABCD

by NormaJane on Sep 16, 2017
Transsexuals & Crossdressers

Obviously trans-women vary, like cis-woman, in psychology as much as in appearance, and my first four encounters with trans-women illustrate this. I have given them these names, because they are appropriate to their behaviour. I met them some years ago, through a free online dating site, which covered the English region I was living in. You posted a note abo...

Return

by Ts Jack on Sep 15, 2017
Non-Erotic

The world was simple and unchanging. There was the Pan, that endless expanse of hardpan and brush that surrounded everything. There was the Tribe. There was the Home. That was all. That was how it had always been. That was how it would always be. The men of the Tribe would hunt the Rach and Drom and Kett out on the dry Pan during the day and watch the sky at...