Gay Anal With Condom Sex Story Stories

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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. **************...

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,...

Freddie Gives Gayle Anal

by BOSTONFICTIONWRITER on Sep 14, 2017
Anal

"Hi, Freddie." "Oh, hi Vinnie." "What's wrong? You look down in the dumps." "I'm stuck writing a story." "You? Stuck? Are you kidding me? You've written a million stories already. You've written so many stories that I can't keep up with you. It makes my head hurt to read that much. Besides, I had to take a break because my finger is blistered from going...

The Crap Shoot

by tango0919 on Sep 1, 2017
Humor & Satire

I was 26 years old the first time I had anal sex. I was dating V, a conservative, deliberate man with Howdy Doody good looks. V and I were doomed from the start, being polar opposites; but the sex was amazing because...um...we were polar opposites. Life can be so unfair sometimes. One night, V shocked the hell out of me by asking if I wanted to get fucked...

I Met s Lady Buying Cigarettes

by Mysteria27 on Sep 16, 2017
Anal

What a night! I was having flashbacks from the night I had just had. I felt like I had been to hell and back. I was hung over and not feeling good at all. I wasn't sure if I had a dream or if what had just happened really did. My body felt like it wasn't a dream. My heart told me it wasn't a dream. I was hanging out with my buddies at our favorite watering...

Pretending to Be Gay to Trick Girls

by jimbo32 on Sep 13, 2017
Erotic Couplings

My name is Paul and I know that it is hard to believe but I came up with a great way to get women to fuck me. I trick them! I first had the idea when I was in high school and some of the hot girls from my school were talking about how they were looking for other girls to be roommates for college because they would never trust a guy and their parents wouldn'...

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...

A Soldier's Wish is Granted

by FountainPen26 on Jan 22, 2020
Anal

This story Falls between The Cowgirls of Baghdad and The Corporal as it follows the main protagonist. ******************** January 2006 As the 747-jet taxied down the runway at Logan airport in Boston, I couldn't wait to get off. I had just spent three days traveling from Iraq to Kuwait to Atlanta and then on to Boston. As I looked out of the airplane win...

The Perils of Young Guys

by Etaindarcy on Aug 7, 2019
Transgender & Crossdressers

Young guys are pretty; but not always so fun. I've only been with one guy younger than me, so maybe I don't know what I'm taking about - but here it is. If you've read my previous stories then you know about my first time with Jack and Kyle and about my special friend Missy and her teenage brother Caleb. If not, let me catch you up. I met Jack and Kyle in...

Haitian Pride Chronicles Ch. 03

by Samuelx on Sep 1, 2017
Group Sex

The name is Teejay Volmar. A big and tall young Black man of Haitian descent living in the Meadowlands area of Ottawa in the province of Ontario, Canada. I'm a third-year student at Carleton University, majoring in Criminal Justice. I recently moved to Canada from the U.S. I spent the past ten years in Brockton, Massachusetts. The City of Champions. I miss m...