Anal Dilation Stories

46,165 results
Orientation
Length
Source
Infinite Scroll

Departing Devotion Ch. 02

by smilde_clouds on Jun 9, 2020
Fetish

-Sep 27- What a strange life I now live. What a strange marriage. Hubby, such a wonderful man, meets all my needs. Emotional attentive, check. Intelligent listener, check. He is an amazing father and steady provider. Our house is peaceful, fun and always alive. He's a sweet lover, though he lacks some confidence. Yet, his confidence shows in the freed...

Cheating Helped Our Marriage

by Tepin on Jul 13, 2020
Erotic Couplings

I had a feeling my wife Carol was cheating on me but couldn't be sure. There wasn't anything big and no our sex life hadn't dropped - if anything she was hornier than ever which was a nice change from our usual 'once a week' sex. At first I thought it was great, she started wearing sexier clothes - thongs, skimpy bra's, sometimes no bra and sometimes she'd s...

Simon Says Revenge Ch. 02-04

by SevMax2 on Jul 14, 2020
Anal

Chapter 2 "Ah, Mr. Avanti. Nice to meet you. Sana said that you'd be coming," the attorney greeted me as I entered his main office after about twenty minutes or so of admiring the secretary. I tried not to be too obvious, but hey, blondes ... what could I say? "Sana?" I asked. "Dr. Habib. I'm Yuri Natansky and you're Simon Avanti, the man who was her pat...

Fourth of July Fest

by Ratamaquee on Jul 27, 2020
Erotic Couplings

It all started at the Jaycee Fourth of July Festival in a little town named Van Buren in Clark County in Southern Illinois, it was 1981. I'm Dave Hughes, and three years earlier I had graduated with a degree in Mechanical Engineering from the University of Illinois in Champaign. A bicycle manufacturer in Clark County recruited me to come to work for them, I...

Sweet and Wicked Ch. 04

by sweetandeasy on Oct 6, 2020
Loving Wives

Note: This series takes a lot of turns, and it's not always easy to pick a category. So be forewarned that there's male/male play in this chapter, along with a few other things. It's really just a romance with lots of wild sex. So it's probably good to just be prepared for anything. Lizzy and I were in bed in the dark, and for the third or fourth time this...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

Pegged Husband

by ilsop on Sep 25, 2017
Fetish

Two years ago, I was a single man with no anal sex experience. Two years ago, I met my future wife at my sister's wedding. Today, I am a pegged husband. Let me start at the beginning. My sister and I are twins. As children, we were always close. Before we went to school, she was my constant playmate. Sometimes, we played Star Wars, and sometimes we played h...

Trying It On For Size Ch. 02

by kelmag on Sep 25, 2017
Transsexuals & Crossdressers

[Just wanted to thank all of my readers who took the time to vote and made Chapter 1 of "Trying It On For Size" the number 1 Transsexual story on Literotica. Thanks for all the great feedback too - it seems there are a lot of would be Kellys out there. Enjoy chapter 2. - Kelmag] I looked up and saw the low slung scrotum swaying above my eyes, the long, th...

Anal At Last Ch. 11

by scottishmeat on Sep 19, 2017
Anal

[The story so far: I've recently divorced my wife, and am raising my son by myself. After a long abstinence, I've met a woman (Angela) and we've been indulging in anal sex, new to both of us. My babysitter (Samantha) was staying at my place one night, and caught me "doing a money shot" over Angela, and I saw her in the shadows of the stairs. Then Angela divu...

Erotic Lingerie Adds To Office Sex

by walterio on Aug 31, 2017
Erotic Couplings

PRELUDE Nannette was driving to work on Monday morning and she was going mad in her car. The new outfit that Joe had bought her was driving her wild. She was wearing the bra with the openings for her nipples and they were rubbing against the coarse material of her blouse. Her nipples were elongated, rock hard and achy from the constant stimulation. She was...