Gay Sissy Anal Stories

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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...

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...

The Making of an Army Slut

by raylene on Jun 25, 2019
Gay Male

My name is Kevin and this is my story. I was raised by my mother. My dad died in a car accident when I was four. My mother done her best. She never remarried and focused her time on providing for her little boy. I was finishing high school. The small town in southwest Georgia didn't have much to offer. I had the grades but not the funds to go to community...

Enticed and Humiliated Ch. 04

by FantasizeAndRealize on Sep 14, 2017
Gay Male

Part 4 - Learning about my Latent Desires Since it was Saturday Sandy said the she was going to go shopping, after we finished breakfast. I told her to have fun, and that I was going to go over to a friend. I called Glen and told him that I could be over in about an hour. He told me that I was welcome. When I arrived at Glen's Apartment I told him about m...

My Time in the Monastery

by brownmonkk on Aug 18, 2017
Gay Male

Brother / Sister/Slave, ("TML") November 1970 "Good loving & Good Scourging" The story of a MASTER and his slave! 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 always imagined having my "first time" with a sexy gal, but nonetheless my first sex was great! I often fantasize and...

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...

You are a Sissy Pt. 08: Future

by Roland15Rollin on Dec 30, 2019
Gay Male

Hello, sissy. Well, we have come to the end of our journey together, princess. We have explored every corner of your gay sissy mind and now we have come to the end. And what a journey that was. We learned so much, sissy. We learned about who and what you are. We learned about what you want. We learned about what you need. And we finally got rid of all of...