Gay Bbc Sissy Chastity Stories

1,088 results
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Infinite Scroll

You are a Sissy Pt. 05: Master

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, sissy. Welcome back, princess. Welcome back to our journey through your sissy mind. You will always come back because I am what you want. I am what you need. You need my soothing voice. You need to hear my voice telling you what a fucking faggot you are. You need my voice telling you what a faggot you have always been. That makes you so happy. You...

What Do You Want Me to Do?

by Cyanlot on Oct 15, 2017
Gay Male

Dear Ted, I hope you're having a nice weekend with Wendy. No ... I don't, really. I just said that to sound nice. But I'm not feeling nice. So why should I try. Honestly, I don't know what more you want from me. If you wanted to end the whole thing because you thought it was wrong or because it threatened your sense of masculinity, at least I'd understan...

Versatility on the Court

by puzziboi on Mar 18, 2020
Gay Male

Matt Wenzel was awakened by the sound of his live-in girlfriend rustling through her drawer. "Babe," he yawned. "Just turn on the light." He rolled back over and pulled the covers over his head. He desperately wanted a couple more hours of sleep. The 32 year-old corporate budget analyst had stayed up later than he'd intended last night fucking the petite chi...

How I Became an African Man's Wife

by Secret_sex99 on Mar 2, 2020
Gay Male

I was straight my whole life. I was married to a beautiful woman for 8 years. We had 2 sons. We were divorced for about 2 years. I was never really athletic. I've always been chubby and more into reading books and eating food than sports. It got worse later on in my marriage as I was now in my early 40's and my metabolism has slowed down significantly. M...

A Femboy in the Wall

by Eastwood on Dec 15, 2019
Gay

DISCLAIMER: I am rewriting this story because I have now learned to use "link chapters". The other story was a mess, and now I'll be able to organize everything and keep writing. UPDATE: now we will have arts to represent certain scenes! Like this: (To clarify, I'm just taking art already made and drawing our protagonist over it and making some ch...

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The Highland Festival Ch. 06: The Walk

by BareBearsFan on Apr 10, 2019
Gay Male

Chapter 6 -- The Highland Festival -- Misbehaving ***Hello Readers Quick note, my stories tend to progress a bit slower, if you're looking for quick paced sex scenes try another story. This story contains nonconsensual sexual acts. Also, some past people nitpick about small consistency details in my stories. I'm not writing a classic novel, I'm not goi...

The Exploits of Cockslut Kelly 05

by CSK on Aug 29, 2017
Gay Male

WARNING!! THIS IS A GAY MALE STORY, BUT IT IS ALSO AN EXTREME BDSM STORY AS WELL. THIS STORY COULD EASILY BE PLACED INTO ANY OF THE FOLLOWING CATEGORIES DUE TO THE CONTENT: GAY MALE, BDSM or FETISH. I HAVE REQUESTED THIS FOR THE GAY MALE SECTION, BUT IT MAY END UP IN THE BDSM SECTION OR ANY OF THE OTHERS IF THE EDITORS OF LITEROTICA DECIDE TO RE-CATEGO...

PIXIE Sissy Stripper Ch. 02

by EROTICbearscribe on Dec 24, 2019
Gay Male

Sunlight played peekaboo through the blinds and woke Benji from the best sleep he'd ever known. He opened his eyes and breathed deeply. His eyes adjusted to the bright light and he looked around the strange bedroom he found himself in. He noticed a fuzzy pink sweater draped over the back of a chair in the corner of the room. There was also a pair of yello...

Brother/Sister/Slave

by brownmonkk on Aug 18, 2017
Gay Male

Brother / "Sister" " TML", November. 1970 A Monk's monk or two virgins in the monastery; "Good loving & Good Scourging "Sissy" does her magic. WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I was a 20-year-old virgin and had fantasized about lots of women. I distinctly remember...

Broken In Ch. 01

by ghostriter on Sep 14, 2017
Gay Male

Jarred woke up earlier than usually, naked and in a yawning stretch, he steps in front of his bedroom mirror. Tall, dark hair, built, and very handsome with chestnut brown eyes, high cheek bones, strong jaw, and thick plump lips. The perfectly soft, light dusting of body hair that covers his body is the icing on his cake. He's conceited, to be sure. He n...