Gay Crossdressing Sissy Stories

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My Gay Crossdressing Vacation Ch. 05

by Flame666 on May 12, 2020
Gay Male

As I was falling asleep, I realized that the egg and the plug were still inside me. Terri must have put the plug back in after fucking me. I wonder where the remote for the egg is. Oh well off to sleep. I was dreaming, I could feel soft hands on my back and running over my panty clad backside. Then I realized that it was not a dream. A pair of delicate hands...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

Blowjob in a Housemaid dress

by DavidHeart on Jul 10, 2020
Gay

There you are. In the bathroom of the hotelroom you took to explore your kinky side. You always wanted to know what its like to suck a cock and take a load. Something about Dicks seems to mesmerize you. Because of that you decided to take a hotelroom over a weekend and see if you find a seizable cock to blow the night. To top if of you even bought a housemai...

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How Did I Get Here

by bart_allen on Oct 15, 2017
Gay Male

I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lip...

Waking up gay

by Honeybunni on Sep 16, 2019
Gay

You stretch and open your eyes. Sun is shining, birds are singing. What a wonderful sleep! Ever since your girlfriend left you, the bed has always felt empty, but that was phenomenal! Finally moving on from that bitch and ready to move on. You brush off your covers, letting the air hit your naked body. Sleeping naked is healthier for you; or so that one Face...

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Transported to Homo-World

by jmce on Sep 26, 2017
Gay

My name is Dick and this is the story of when I ended up in Homo-World, the adventures I had there and how it ended. It started a normal enough day, I woke up, took a shower, brush teeth etc. It was Sunday and I had nothing planned when Love called and asked "Hey, you have anything planned?" "Honey, it's Sunday. The only thing anyone ever plan...

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Complete Control

by vicw1392 on Apr 27, 2014
Gay

James had read, and seen, porn about men who could change the world, and that's what he'd been doing last night. After a quick, and mostly unsatisfying, wank, he'd fallen asleep wishing that there was more of this type of porn for gay men; where was the fun in reading about unlimited possibilities if all the characters do is make everyone's tits bigger? Then...

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My Gay Crossdressing Vacation Ch. 06

by Flame666 on Jun 9, 2020
Gay Male

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night. I remember...

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...