Gay Sissy Fag Stories

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Infinite Scroll

The Head Boy's Fag Ch. 01

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

THE HEADBOY'S FAG - 1 THE FAG'S FIRST DAY AT OLLERTON COLLEGE A Homoerotic Story This is a short story concerning the the Head Boy's fag at an English public school called Ollerton College, located in a small county in the south west of England. The time is the early twentieth century, before the Great War, which changed so many things in England. But at...

Dr. James and His New Treatment

by Suferdude on Jul 11, 2018
Gay Male

James was a tall dark handsome man who worked as a part time Doctor within a rehab facility in San Francisco. He was 6 feet tall and had a gentle beard and soft brown eyes, people often thought him to be a gentle and kind-hearted person. And people would, for the most part be right. However, like everyone, Dr James had a darker side and his work at the expe...

Improper Advances Ch. 04

by bjmichaels on Sep 19, 2017
Gay Male

I became lost in the sucking. Every time I went faster, he would slow down the pace. I gently stroked his shaft and caressed his balls. My own balls were so painful I knew I wouldn't last much longer. This time when I furiously bobbed my head faster-and-faster he didn't slow me down. I was so consumed with the rigid pole of flesh inside my mouth I though...

Panties, Panties, Panties

by bjmichaels on Apr 3, 2019
Gay Male

Don't Call Me Pantyboy I couldn't believe my ears. I shouted at my roommate: "What are you saying? Are you accusing me of wearing women's panties? Are you saying I LIKE wearing women's panties? I wear MEN'S briefs -- and they're COTTON!!" He smirks and says, "You know, John, teenage girls wear red cotton panties too!" I am apoplectic. My face as red as...

"You Go First," Samantha Said

by donaldelliott11 on Jan 21, 2020
Gay Male

[Most authors love feedback. Please let me know how I did.] This is the third story in this series. You will want to have read the other two. https://www.literotica.com/s/you-go-first-01-jake-said https://www.literotica.com/s/you-go-first-02-john-said + + + + + + + + Jake phoned me Tuesday morning and told me to come visit him that afternoon. His paren...

My First (but not last) Cock

by DixeenormousToo on Sep 16, 2017
Gay Male

I started late in life on my journey to being a cocksucker, a year or so after my 50th birthday. I had spent years and years of fantasizing about being on my knees, a big, throbbing, boner down my throat and being rewarded with a hot, thick load of man cream. But I should slow down, my dick is already stiffening just typing those words and I need to get this...

The Sponsors

by analvirgin4older24 on Aug 18, 2017
Gay Male

Back when I was just an 18-year-old high school senior. I was an Olympic caliber swimmer. After an All-American senior swim season, I decided to compete in state, regional, and national competitions. To do this I had to seek sponsors for expenses such as training and lodging at each competition. Luckily my dad knew this guy Ralph who owned a construction,...

Rince and Spit

by Compliant1 on Aug 18, 2017
Gay Male

"How's that Dave, does it still pinch the gum?" "It feels much better, Jim. Thanks for seeing me today. I don't think I could have made it until Monday." "Don't worry about it. My softball game was rained out. I'm going to take your plates out to polish them. Open just a little wider. I wish all of my patients were as easy to work on as you. I wish I had a...

Greek Delight Ch. 02

by S_Queen on Sep 25, 2017
Gay Male

When I woke it was morning and I was erect. The sun was up, and I could tell it was hot. Looking over, I saw a slender, feminine body lying naked on its front, face away from me. The back curved into the most delicious ass, round and peachy. I reached out and touched the bottom, the soft skin like marble to my fingertips. I gently squeezed the firm buttocks...

Sissy Bottom Has a Nite Out Ch. 02

by lostsoul1974 on Sep 14, 2017
Gay Male

Last night, my friend Eric and I had some really hot sex down at the Adult Theatre. Eric had me wear a pair of my wife's panties and I was a sissy fuck-boy for a whole theatre full of horny men. My wife is out of town for the weekend, so we are gonna be as lecherous as two bisexual fuck-buddies can be. This morning, I awoke to the sensation of Eric's hand s...