Gay Sissies Stories

124 results
Orientation
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Infinite Scroll

Discovering my Talent Pt. 01

by DRobbie06 on Aug 24, 2020
Gay Male

I had just turned 18 a few days earlier. I was over a friends house (Brian) playing cards with several guys including my friend's dad and one of his coworkers. Over about 3 or 4 hours, one by one, guys would leave when they were out of cash. With only myself, Brian, his dad (Nick), and his dad's coworker (John) left we decided to call it a night. I didn't h...

You are a Sissy Pt. 07: Cuckold

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, princess. Hello again. I see you are back. That pleases me, sissy. It pleases me that you have come back for more of what only I can give you. The truth only I can give you. And we have come so far together, princess. We have come so far exploring the depths of your sissy feminine mind. And your mind is feminine. Make no mistake about it, princess....

What Being a Sissy Wife Means to Me

by SissyWife on Aug 18, 2017
Gay Male

I am a sissy wife. I hate clichés as much as the next girl, but sometimes they make for the most apt of descriptions. I have a job, friends, and a life. I go out, I go out for movies and drinks. I enjoy long walks and drives, and I love travelling to new places and locations. And yet, there was something missing. There was something that was needed. I found...

Breaking In Pt. 02

by Iamkrazy4 on Dec 24, 2019
Gay Male

After laying on the ground for a few more minutes, I got up, grabbed my phone and headed to my bedroom. I quickly unlocked my phone and watched the video of what had just transpired. My dick immediately got hard, but instead of taking care of it, I slipped two fingers into my still lubed ass and fingered myself hard for the duration of the video. I spent a...

Virgin Asian Dominated

by primalenergies on May 12, 2020
Gay Male

Disclaimer: I might not be the best storyteller, but I'll try at least. This story also involves racism, cheating and a top putting his bottom in panties, so if that's not your thing you shouldn't read. To understand this story, you need to know I've always been a bit gay, though I've tried to hide it and I've been insecure over the effeminate behaviour tha...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

My Inner Slut

by SlutAlexR on Oct 9, 2018
Gay Male

So lets start from the beginning: I've been married for 12 years. Don't get me wrong: i love Bridget. We have our ups and downs, like every couple. But I do love her. However, sex life isn't what it used to be. And for about a year now, I have been having these recurring cravings to be with men. I don't know where this comes from, or if it will go away. But...

Compassion is a Way of Being

by bawdybloke on Jan 8, 2019
Gay Male

I never knew his name; our hosts never told us. Neither did I know where they found him. He wasn't the first young man which the posse of imperious dominants had provided for the entertainment and he wouldn't be the last. The submissive character and accommodating nature of the sluts which brightened these parties always entranced me. They loved to serve; t...

67 Cocks

by yvetteinpanties on May 15, 2019
Gay Male

I became a cocksucker at age 55. I started slow, responding to internet ads every six months or so. Afraid of disease, afraid of being seen by someone I knew, afraid of being myself. As the urges grew, so did the frequency of my encounters. Sometimes I was a sissy in lingerie, sometimes I was just naked, but I was always a bottom. When I retired, I moved to...

Just a Little Curious

by eviltwin52 on Aug 18, 2017
Gay Male

Who would have thought? I'm 40ish, living alone in my own home with extra money to burn. Extra money...? Never thought I'd get to this place. Being an avid reader and horny, my web surfing brought me to Literotica. Forced Bi and cuckold stories resonate in me and I actively seek a Dom couple. After contacting several couples I get the response I was lookin...