Gay Sissy Strapon Stories

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Time for a Change

by tonyl65 on Sep 14, 2017
Gay Male

Here I am at 30 divorced and moving into my new house, in a new State, with a clean slate. Six months ago I came home from work early not feeling well. I walked into my bedroom and saw a big hairy ass moving a huge cock up and down and in and out of my wife's pussy. Her legs were dangling over his shoulders as she was screaming to be fucked harder. My wife a...

March Madness Ch. 07

by watchdwag on Sep 14, 2017
Gay Male

It felt really weird waking up beside another man in my bed. My ass was pressed against Larry's cock as I woke with his arm gently draped across my waist. It was a position to which I was accustomed with my girlfriend Sandy as she would often cuddle close to me in a spoon position in the bed. I looked over and Larry appeared to be dead to the world as I pull...

Somethin' U Wanna Know

by Kapricorn71 on Aug 18, 2017
Gay Male

Dear Mrs. Madson: I first encountered your husband online. He was in a chatroom for bi and gay men. His ID was 4dafunofit. I checked out his profile; and while he did list himself as married, there was a picture of his bare ass. I'm sure you know how sexy your husband's ass is, so it shouldn't shock you to know it turned me on. I initiated a conversation w...

A New Experience in Switzerland

by carl4use on Aug 18, 2017
Gay Male

I visited Switzerland just after my 20th birthday. I had taken several mature men's cocks in my mouth and ass but what I was going to experience in Nyon never crossed my mind. I was seated at my table at a café eating breakfast on a beautiful morning. I noticed the guy that sat at a table across me looking at me over the newspaper he was reading and smiling...

First Time Glory Hole Adult Store

by justaguy84 on Apr 23, 2019
Gay Male

Like many married men, I've become curious. I'm happily married, I love my wife, and I had never been with anyone since our marriage. But I began to fantasize about using toys, dildos, and ultimately being taken with a strapon. That was a huge turn-on for me but it was just fantasy. I began getting toys and began using them, and then I found cum eating instr...

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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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...