First Time Pegging Stories

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Orientation
Length
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Infinite Scroll

Weekend Away Ch. 01

by jlassa on Sep 14, 2017
Exhibitionist & Voyeur

Since we first became a couple and began a sexual relationship, Stan had always fantasized about sharing me or seeing me with another man. Over the years, we have used this fantasy in our lovemaking as much as any other fantasy, maybe more so. For most of our marriage, this has been agreed to be a fantasy-only fantasy, meaning that we both agreed to never...

The Mark of Jane

by xtcnymphette on Sep 1, 2017
Group Sex

A young women returns to her hometown and uses her erotic charms to wreak revenge on her ex boyfriend and best friend the week of their impending wedding. I emerged from the shower with the moisture still trickling over my body, naked except for the fluffy white towel wrapped around my bust line. I had been planning this weekend for a long time; I wanted e...

Og's Blog Pt. 09

by oggbashan on Jul 13, 2020
Reviews & Essays

Og's Blog Pt 09 Og becomes a civil servant. Part 05 Starting in Devonport. Author's Note: Because of the Official Secrets Act, this has to be regarded as a fictionalised account and names will be omitted or changed. Any names given will not be the names of real people. Please note that Parts 01 and 02 of Og's blog are transcripts of posts made on the Auth...

Saturday Night Fever - The Sequel

by watchdwag on Sep 19, 2017
Group Sex

As the weekend approached, I became more and more anxious about what I had agreed to do. My name is Chris and last fall I was seduced by a hot blonde in her early thirties named Terry, who took me back to her apartment where her boyfriend Jim and another man introduced me to gay sex. While I did have sex with Terry as well, she encouraged me to give her boyf...

The Casting Couch

by chezshirecat on Sep 19, 2017
Interracial Love

For as long as Allison could remember, she'd wanted to get into acting. But coming from a strict, religious family, she was discouraged from pursuing it as a career. When she was 21, she married her high school sweetheart, who wrote part-time at the local newspaper and freelanced for magazines. She worked at a temp agency and made a good living. They were h...

Canada-I-O

by Isis_1 on Sep 13, 2017
Romance

Julie looked out the window of the airplane and felt both giddy and nauseous. "Am I insane?" she wondered for the fiftieth time that day. "What if he hates me? What if throws me off his verandah? What if he's indifferent, and doesn't even care that I've come?" Julie posed one absurd question after another, partly to draw out her unspoken fears, and partly to...

Next Step to Nirvana

by Lia Monde on Sep 13, 2017
Transsexuals & Crossdressers

As I sat on the bench at the mall, I tried to calm myself. I thought I had prepared myself and planned everything. But my breathing was fast, my hands were sweaty and my nerves were wired. I was home for holiday break from college and had decided to take the next step in cross-dressing. Up until now, most of my dressing had been secretly taking my older sis...

The Gynecomastia Kid Ch. 01

by Johnboy9 on Sep 14, 2017
Transsexuals & Crossdressers

This story will be told in first person narrative but this first part is written in third person narrative because the first person, or main character, is unaware of the events unfolding in this scene. ***** Inside the kitchen of her boyfriend's house Crystal makes a last ditch effort, calling his stepmom, Dr. Burns, for help: "Crystal, you're saying all...

The Lone Spring

by Native Alien on Sep 13, 2017
Erotic Couplings

Standing outside, in the cold air, looking up at the stars. Not moving, just listening to the sounds of the night. Nothing is stirring. The air is cold on my skin where the blanket that I am wrapped in doesn’t cover me. Nothing on but a pair of moccasins. The stars are bright in the night sky and the moonlight is bright. I think of the hot springs just behi...

Spring of '39

by alexcarr on Sep 16, 2017
Romance

In the Spring of 1929, Ivan Jones had regained his self esteem when, after a year of unemployment, he was taken on in a new Government incentive to find jobs for unemployed South Wales miners. It meant leaving his beloved home, his mother and father for the first time but it made a lot of sense and also gave him the opportunity for leave the nest and fend g...