Gay Sissy Crossdresser Stories

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Abused by a BBC

by Experimental901 on Oct 24, 2018
Gay Male

Thank you so much for reading my first written submission! I've wanted to write erotica for years now but I've never really had the courage or the time to get started, until now! I realize I may have some work to do and I would gladly accept any advice or future story requests that you may have! * I had always considered myself straight. I'd had a few girl...

First Time Anal

by iamcontent on Sep 14, 2017
Gay Male

I have always known I was bisexual since I was a kid. I have topped but never bottomed, I have attempted bottoming a few times. First time I was in my teens and my friend and I tried, we didn't have lube and I wasn't stretched out properly. A few months ago I bought a butt plug which is 4 inches long and a 8 inch dildo. I lube every night and put the plug in...

My First Guy in the Park

by Tonisshy on Aug 18, 2017
Gay Male

Briefly this is me, I'm 24, 5'5" and 126lbs. My hair is long dark brown and my complexion is natural tan from my native heritage. I've been a crossdresser ever since I was born. Period. Now that I live on my own I have all sorts of outfits, makeups, shoes, breast forms and toys. I just have one thing I have never done. I've never been with a man. I've fa...

Julian entdeckt Julia

on Jun 16, 2018
Gay

Mein Name ist Julian und ich bin 19 Jahre alt, schlank, sportlich. Vor ein paar Monaten bin ich nach meinem Abitur von Zuhause ausgezogen um zu studieren. Schon kurz vor meinem Abitur entdeckte ich beim, fast schon alltäglichen, Pornodurchstöbern mein Interesse für Crossdresser Pornos und Videos, in denen süße Twinks von reifen Männern vernascht werden. Nach...

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I was Hard on Nude Beach

by LucyFrance11 on Mar 6, 2018
Gay Male

I live in a naturist complex in Leucate in the South of France and whenever possible when I go on holiday I look to stay in places that have nude beaches. I get so aroused being naked and showing off my shaven body to anyone who likes to look. I am in my 40s, 6ft tall and slim as I exercise a lot. I am also gay and a crossdresser but more of that in later st...

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...

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. 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. 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...

My Gay Crossdressing Vacation Ch. 02

by Flame666 on Apr 21, 2020
Gay Male

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some e...