Boys First Time Stories

351,345 results
Orientation
Length
Source
Infinite Scroll

Obedience Training Pt. 02

by zuluking72 on Sep 16, 2017
Interracial Love

She had her orders. At exactly 5:00 pm she was to be at the given address with fried chicken, cold beer and a good attitude. At 3:00 she made up her face carefully and dressed as directed: short skirt, red thong panties, white blouse, no bra. Looking at herself in the mirror as she applied make-up and brushed her long, wavy locks, she smiled in satisfactio...

Milked

by scorpio1111 on Jun 15, 2020
Toys & Masturbation

***ALL CHARACTERS OVER AGE 18*** I led my hands up his jeans - tight, with a sliver of skin starting to show at his waistband. He waited patiently, not nearly as pathetic as some of the boys I'd known, grabbed my hand and led it closer towards him. "Is this what you want?" I asked, fingertips gripped around his waistband, against the soft give of his smoo...

My Name is Raquel Ch. 01

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

Chapter 1 All characters in this story, involved in sexual situations, are 18 or older and are fictional. ******** My name is Raquel and I'm a crossdresser. I didn't become Raquel until later, but this is where I came from. At this point my interests lied only in panties. I wore them as often as I could get away with, as long as I could change out of the...

An Afternoon in the Pool

by amee086 on Sep 12, 2017
First Time

My name is Amee. I am 24 years old and I am currently working as a volunteer in a remote community educational project in Southeast Asia. The conditions are very Spartan and the nights are long, my only enjoyment being my thoughts, fantasies and fingers. Like many girls I suppose, I remember every delicious second of my first sexual encounter with a boy. I...

Teacher Rita Gives Private Sex Education

by fantasyboy on Sep 12, 2017
Erotic Couplings

Rita had been happily settled in her job for the past 18 months. It had given her the opportunity to escape from the problems that had blighted her life in the past. She was now living in a large house just north of London and working there as a private tutor and governess to Robert whose parents were continually working abroad and travelling around Europe....

The Garden Club Ch. 03

by MsMarg on Sep 17, 2017
BDSM

I wake early, stretching, I smile. It's just after 4:00 am. Will he arrive on time? I am sure he will be here. He can't stay away. I am anxious for him to be here, this is new. With Robb I am anticipatory, scared, and nervous; excited, angry and aggressive with the subs. But, this is different, I can't wait to see him, I moisten at the thought of him, not wh...

My Wife's Black Master Ch. 03

by q-tip on Sep 13, 2017
BDSM

I was sniffing the milk carton, trying to determine if it was still good, when Jane walked by me the next morning. She had a slight smile on her face and she was shaking her head, she thinks its funny when I do things like sniff the milk. Of course, she was completely dressed, covered from head to toe so that I couldn’t see the magic marker writing on her bo...

Seduction or Betrayal? Ch. 05

by Touch_type on Aug 14, 2018
Novels and Novellas

This is part five of a seven-part novella; it should stand alone, but beginning at the beginning is the recommended pattern. I'm posting all the chapters at the same time so you shouldn't have to wait long for the rest. A Literotica Box Set for the summer. The original idea for this work came following a discussion at the authors' hangout about frustrations...

The Business Deal

by Womenlovemonsters on Sep 11, 2017
Interracial Love

DISCLAIMER: This story involves big black cock and a cheating white wife. Yes, those are stereotypes, and if you don't like them, don't read this. No I don't believe that black men all have huge cocks, nor do I believe that women can actually take a cock as big as the one in the story. It's erotic fantasy. I write it because I find it hot, not because I beli...

Not Going To Do It

by Just Plain Bob on Dec 1, 2017
Loving Wives

It was a dismal April day and word was spreading through the camp that Bob Lee was going to throw in the towel. I don't know how the other boys felt about it, but I hadn't been fighting those damned Federals for four years just to walk in front of them and lay my Enfield down. Bob Lee could give it up at Appomattox, but I wasn't by God going to do it. They c...