Gay Sissy Gloryhole Stories

915 results
Orientation
Length
Source
Infinite Scroll

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...

A Real Bathhouse Slut is Made

by Danmo1 on Sep 16, 2017
Gay Male

This true account of the activities of a mature 50'ish guy continues from my first time at a bathhouse entitled The Making of a Real Bathhouse Slut. As I drove home from the bathhouse the first week I had a hundred different things going through my head, one of which was guilt. I quickly realized that after years of no sex with my wife there was really noth...

My First Encounter With a Man

by Just_TM on Sep 14, 2017
Gay Male

I found myself there more by accident than on purpose. Or so I tell myself anyway. The fact of the matter is that I was yearning for this new experience for quite some time. There was just something enticing about man to me even though I was (and still am) quite the ladies man. For years I was "curious". My first true step was to buy a Bi video. The sight I...

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...

Lonely Traveler's Conversion

by joedoe22 on Jun 26, 2018
Gay Male

I had been traveling and working on what seemed to be a never ending project flying to different offices of our clients scattered throughout the country. It was impossible to meet a woman to date, let alone have any type of relationship when I was on the road a week or two at a time. I had recently moved to an apartment to be closer to the airport since I wa...

My First Gloryhole

by liquidbord on Aug 17, 2017
Gay Male

Let me set the scene for you. It was the end of my first semester sophomore year in college. I had been dating the same girl since mid-way through our freshman year. Things were going well, we were both happy. We were getting ready to head back home for winter break as the college emptied out. Our plan was that she was going to come stay with me for a couple...

Gloryhole Fun

by james_ga_us on Aug 28, 2017
Gay Male

I love going to the adult bookstore in Birmingham, Alabama to visit the glory holes! Just last week I went and paid to put some credits on my card and walked into the booth area to see only two guys hanging around. I immediately went into my favorite booth and started the video and was pleased when I heard the door open in the booth next door. As I was selec...