Gay White Sissy Stories

10,754 results
Orientation
Length
Source
Infinite Scroll

First Time Fucked

by tinywhiteboi on Aug 18, 2017
Gay Male

It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends. Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serv...

The Backpacking Trip Ch. 01

by lockedinsteel on Nov 21, 2017
Gay Male

"It's what I want for you baby," said Jamie. Her husband, Daniel, was still a little uneasy with the idea. "I know you've wanted to explore that for years and I think that if you get the opportunity you should. In fact, I'm giving you an order. Do it if you get the chance. Promise me!" she told him. "Okay, Okay I get it. I promise, my love," he replied....

Beauty and the Beast Pt. 03

by Suzzique on Jun 3, 2019
Gay Male

"Well, well!" said Daddy in a tone of mock surprise, "Your Uncle Ted has made it here after all. And for once he's timed it just right." "You promised," I cried out, on the edge of tears again. "I lied, you dumb sissy. I lied." He laughed. "Cut the jokes, Jack. Give me the bitch. I've come a long way to get my cock up the little slut. I want her now." "...

Hallowiener Pt. 03

by forummj on Jun 18, 2018
Gay Male

I yanked my cap down tightly and bowed my head. Hunching my shoulders forward I pulled my rucksack tight to my back and made a dart for the front doors. All my fellow students made their lazy way to class as the bell rang. I felt like they all knew what had happened last night, and I didn't just mean the party. I was nervous, almost scared that they knew. "I...

Was I Raped? Ch. 04

by eviltwin52 on Sep 14, 2017
Gay Male

"What the fuck did you say to me bitch?" Uh oh. I'd pissed Daddy off. I'd been whoring for Daddy for three weeks now. I can't remember the number of black gentlemen who have enjoyed what I have to offer them. Still using my hotel room, every penny I earned went to Daddy. But that was a problem. The hotel wanted their room paid for and my credit cards have...

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...

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...

You are a Sissy Pt. 01: Awakening

by Roland15Rollin on Dec 24, 2019
Gay Male

Are you ready? Are you ready, princess? It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long. You've been ready for your whole life princess. It's time to drop the mask and be who you are. Who you really are. What you really are. No more l...

Cum on Panties

by jakladd on Aug 30, 2017
Gay Male

Cum on Panties - Our phone sex is always so hot, you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings & high heels, telling me how perfectl...

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...