Gay Sissy Femboy Stories

766 results
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Infinite Scroll

Under the Gaze of the Sirens 03: Who Knew?

by jakladd on May 12, 2020
Gay Male

Your girlfriend treated you like shit. Always in charge, always aloof, always flirting with other guys in front of you, rubbing your face in it. Even your roommate, she flirted with him. You dated for two months and she only gave it up once. She was drunk that night she screwed you. She told herself you would never get lucky with her again. It was such a dis...

Sex Mercenary Ch. 02

by KittyAshleyy on Mar 12, 2019
Gay Male

After accepting the Underworlds job offer I packed all of my belongings in a medium case and dressed in a white crop top, ripped skinny jeans on top of newer fishnet tights (all of the holes the right size), my black leather jacket and my boots. "How do I look?" I asked the Underworlder in the suit. He simply nodded and we left my room. Outside was a blac...

Feeling Normal Ch. 03

by Ty3958 on Jan 30, 2018
Gay Male

Before you read the story, I just wanted to apologize for the long wait for part 3. I finished the semester and went a little crazy with my new found freedom, lol. Anyway, I hope you enjoy part 3 and hope that it's worth the wait. ***** It had been a month since I had spoken to Ethan and it's been a depressing month. We had a great connection, but my fear...

Feeling Normal Ch. 01

by Ty3958 on Dec 9, 2017
Gay Male

It had only been a little over a year since I had been diagnosed with HIV. I had been completely devastated by the diagnosis; I had never slept with anyone and I felt that I never would now. I'm still perplexed as to how none of the doctors I had ever been to saw it in 22 years. My mother, whom I got my HIV from through birth, had been dealing with her diagn...

Controlled Chaos

by Blammer on Jan 8, 2017
Gay

Aslan was an amazing and vibrant world. Long ago it was forged, like a weapon, by the gods. Life was littered across it shortly after. From the littlest bug to the biggest gigantes. Goblins, orcs, elves, dragons, etc. The world was sometimes a little crazy and war was a possibility. You thought you were below all that, a tiny flea in the grand scheme of thin...

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A Dark Ride

by SecondCircle on Sep 14, 2017
Gay Male

I was trying to make the best of it. There just wasn't enough alcohol at the bar to make me forget I was a fish out of water. It wouldn't hurt to try though. "Can I get a vodka and cranberry?" I called to the bartender. The gruff looking guy shot me a look that should have been enough of an answer. "Look, man, we got beer and whiskey!" He shouted ove...

You are a Sissy Pt. 03: Body

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello. Hello, sissy. You have come back. You have come back again for another session. Welcome back, faggot. My sexy sissy faggot bitch. I am so glad you have come back. But you have no choice, do you, sissy? You have to come back. You need to come back. You need to hear my voice. It is the voice of truth. The voice that tells you what you are. What you tr...

You are a Sissy Pt. 02: Public

by Roland15Rollin on Dec 24, 2019
Gay Male

Welcome back, sissy. Welcome back, my little sissy bitch. We came so far in our first session. You came so far. You once thought you were a man but now you know better. You are not a man. You have never been a man. You are a sissy bitch. And that makes you so happy. So fulfilled. You love being a sissy bitch. A faggot. A gay little toy for real men to use...

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....

You are a Sissy Pt. 06: Slave

by Roland15Rollin on Dec 25, 2019
Gay Male

Hello again, princess. Welcome back. Welcome back yet again to our journey through your mind. Our journey through your feminine girlie mind. We are almost there, princess. We are almost to the end of our journey together. I know that makes you sad but it's okay. It's okay, my sweet sissy. It's okay because we have more to cover and I will always be with you...