Gay Sissies Stories

124 results
Orientation
Length
Source
Infinite Scroll

Winners and Losers Ch. 07

by bawdybloke on Sep 15, 2017
Gay Male

If you have missed the previous instalments the premise of the story is that after a football match, the losing team must provide sexual relief for the victorious players. Previous chapters for Winners and Losers are on Literotica. * * * * * There was no denying that the last minute loss to AFC Kerlon had dented confidence in the dressing room, but when...

You are a Sissy Pt. 04: Women

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello again, sissy. Hello, my sissy bitch. I am so happy that you are back yet again. You love coming back to continue our sessions, sissy. You love coming back because I am helping you. You need my help. You know you need my help, sissy. You need to come out of the closet and let the world know what a gay cocksucker you are. You need to let the world know...

Bio of a Bully Ch. 3: Big Brother Pt. 1

by ozeboi69 on Sep 14, 2017
Gay Male

I told you about how I broke into that chick Chrissie's house one night and taught her a thing or two about fucking with me. See, she really wanted me bad, but didn't want her friends to know it, right? So she was bad mouthing me and stuff with sarcasm. I went over there and let her have what she wanted, and I told her that if I heard her bad mouthing me aga...

I Sucked The Sheriff

by Web Dazell on Aug 18, 2017
Gay Male

"ADVENTURE (noun): an unusual and exciting, often hazardous, experience or activity." The New Oxford Dictionary of English Welcome to the second story in my new "Adventure" series. (The first is "Devil With A Blue Dress On" in the transgendered section.) My two previous stories "The Arrangement" and "Breaking The Arrangement" were autobiographical. Everythi...

His Sweet Boy Ch. 06

by Her11 on Sep 21, 2020
Gay Male

AU: I'm Back! I know i was a little slow to write but im working on it. P.S. to Crven_ban: do not read my mind it freaks me out. To everyone else, 40th comment on His Sweet Boy Ch.04 ********* Ben slammed the office door, then spotted the bathroom and shuffled awkwardly into it slamming that door for good measure. Fucking hell. Eric was going to be the...

Little Sex Toy Ch. 04

by keptsissy on Sep 26, 2017
Gay Male

I'm over a complete stranger's knee, butt way up high with his left hand and huge arm wrapped over my back and up under my stomach. He has the flat inside of his left palm pulling me up slightly off his knee. It hurts. I feel him push up into my stomach. He could pick me up like this, pick me up and hold me upside down if he wanted to, he's that strong. He's...

A Very Big Man!

by keptsissy on Aug 30, 2017
Gay Male

Of the men I see regularly he's the biggest. Not just height and weight, his cock is huge, close to 11". And his cock is thicker than any other man I've ever seen. My ex-boyfriend introduced me to him at a party. He told me to go to the bedroom with him and 'be a good girl'. It was one of 'those' parties, all of us girly girl sissies on full display and on t...

The Customer (Dexter's Saga) Ch. 06

by JoyStick56 on Sep 14, 2017
Gay Male

Disclaimer: This story may contain scenes of a graphical nature that may not be legal in your area. If you are under 18, or if material of this nature is illegal in your present location, please leave now. By reading on, you are confirming that it is legal for you to view the material in this story. This story is a work of pure fiction. Names, characters, p...

University Discoveries Ch. 04

by fantasyhunter2 on Sep 14, 2017
Gay Male

I am continuing this long dormant story of male discovery by request. Saturday morning I woke up early. The anticipation and resulting anxiety of that night's date had invaded my usual easy slumber. I sat on the edge of my bed trying to decide what to do. Greg was in his own bed snoring away. As had become our habit he was sleeping in the nude. Since the w...

Prison School Ch. 04

by o2byoung on Sep 14, 2017
Gay Male

Mike and Vern walked into Dorm 2 and noticed that most of the guys were in the rec. room. If anyone was aware that they came in together, nothing was mentioned. Most of the men were used to seeing the kitchen crew come in a little later anyway. They went to their lockers, got towels, soap, and clean boxers, and headed to the shower. Since most of the guys ha...