My First Time Gay Anal Stories

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Wife Admits to an Unusual Fantasy

by david_f on Oct 9, 2018
Loving Wives

This story has bi male sex in it so if that offends you stop reading now. It's in the Loving Wives category because that is where my Loving Wife took us. This is a true story that actually happened one night. If you are curious about how this happened after nearly twenty years of a strictly heterosexual marriage then continue reading. It's not a homosexual s...

Anal Sex 201: Male Penetration

by jsragmanus on Sep 11, 2017
How To

INTRODUCTION Male anal penetration is a sex act that carries many stigmas with it, yet done right it can be amazingly pleasurable. I've written this HowTo as a guide for heterosexual couples who want to introduce male penetration using strap-ons into their sexual repertoire. Many men are interested in anal play but are either uncomfortable approaching thei...

Anal, Again!

by Olive Hizklosoff on Sep 12, 2017
How To

Let's talk seriously about anal stimulation and anal play. The truth is that the anus is one of the most significant erogenous zones of the body. You can talk about sucking on nipples or earlobes or clits or penises but none of them have the eroticism of the asshole. It's the "dirty" place that seems so popular at the moment. Sure, the anus is the receptacle...

Freddie Decides to Finally Try Anal

by BOSTONFICTIONWRITER on Sep 16, 2017
Anal

I've been doing some research about anal sex. For those who require background in my reticence to try anal sex, please read my story, Anal Sex What Is the Big Deal. I hid in the men's room at the Logan Airport waiting for a couple gay guys to come in and, you know, and have anal sex. No one came in and finally, I was asked to leave by Mass Port Security. Bo...

Tantric Massage Pt. 01

by eroticwriter00 on Sep 16, 2017
Anal

My name is Evan. I'm 5' 11" with blonde hair that curls just below my collar. My tummy has ten extra pounds that I'm trying to lose, my shoulders are broad and I have chest hair that is trimmed on a regular basis. I've been married for thirty years and never cheated once. My son and daughter are married and I recently became a grandfather. My wife is wonde...

Junior Year Abroad Pt. 04

by JBEdwards on Mar 30, 2020
First Time

This is Part 4 of the Survivor Revival Challenge, organized by Tara Cox. This is the story of Jim & Marybeth, and eventually others, of course. You can expect daily installments. Special Note: This story describes both Jim and Marybeth having anal sex for the first time. As such, it's a 'First Time' story, as well as an 'Anal Sex' story. **************...

All Women are Bitches Ch. 20

by Samuelx on Sep 14, 2017
Anal

Come on, Men. Get in my booty! I'm on my hands and knees, my plump butt cheeks spread wide open. My pussy is wet and dripping with anticipation. My name is Talisa Rodgers and I am the kind of girl your mama probably warned you about. The chick from the hood. The gangsta bitch who loves dick. And cannot get enough of it. I crave the cock. The bigger the bette...

Exit Only? Taking a Drive Down...

by LaceySheets on Sep 16, 2017
How To

Exit Only? Taking a Drive Down the Hershey Highway A Beginner's Guide To Anal Sex Is your partner an 'ass man?' In my research I've found that males are either ass men or breast men, with leg men ranking a distant third. I've also found that even an ass man can be repulsed by the idea of anal sex. Of all the third-grade humour names for anal intercourse,...

Anal Sex with Stranger on a Train 05

by SusanJillParker on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 5 Peter finally meets Roberta again, the love of his life. In just a few minutes, Robert returned to the room dressed as Roberta. Giving him a sexy cross dressing show, by her feminine antics and charms, she obviously enjoyed being watched by Peter. With a shake of her head and with a flourish, as if releasing her sword in Zorro, the gay blade, sh...

Believe It Or Not!

by jessy19 on Sep 12, 2017
Reviews & Essays

Believe it or not, some women actually do like gay porn. I must admit I am one of them. Now it's been known for sometime that this trend is getting more popular. I first felt ashamed about it. I always knew that men loved lesbian porn and yet I never heard any female admit she liked seeing two guys making love. It was as if watching two sexy women go at it w...