Gay Sissy Roommate Stories

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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. 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...

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. 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....

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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Demographics

by male_sharmota on Sep 16, 2017
Gay Male

I woke up a bit before sunrise and climbed down the ladder of my bunk bed. My roommate laid sleeping in the bottom bunk next to my wife. I looked at myself in the mirror on the wall. My middle-aged body was still in good shape. The legs, ass, and chest were well shaved to provide a clear view of my smooth white skin. So was my face. My neatly trimmed bush lo...

Submitting To My Roommate... Ch. 02

by chriscili on Aug 18, 2017
Gay Male

The next morning I woke up and got out of bed. Chris had already gone to the shower so I went to my mirror to see what I looked like. I really shouldn’t have been surprised when I saw that my face was covered with dried cum. I grabbed my shower towel off a hook on the back of our door, used it to dry rub the cum off my cheeks and lips and then wrapped...

Panties, Panties, Panties

by bjmichaels on Apr 3, 2019
Gay Male

Don't Call Me Pantyboy I couldn't believe my ears. I shouted at my roommate: "What are you saying? Are you accusing me of wearing women's panties? Are you saying I LIKE wearing women's panties? I wear MEN'S briefs -- and they're COTTON!!" He smirks and says, "You know, John, teenage girls wear red cotton panties too!" I am apoplectic. My face as red as...

University Discoveries Ch. 04

by fantasyhunter2 on Sep 14, 2017
Gay Male

I am continuing this long dormant story of male discovery by request. Saturday morning I woke up early. The anticipation and resulting anxiety of that night's date had invaded my usual easy slumber. I sat on the edge of my bed trying to decide what to do. Greg was in his own bed snoring away. As had become our habit he was sleeping in the nude. Since the w...

Roommate Turned Me Out

by ralphcollant on Nov 2, 2020
Gay Male

It was a typical Tuesday afternoon after my last class for the day. I walked into my dorm room and found my roommate, Mike, watching porn on his laptop. This was not unusual for either one of us. Some of this junk could be quite entertaining. He nodded and said "Hey Tim" as I walked in and then waved me over so I could see what he was viewing. It was some pr...