I just had sex with my first sissy and wanted to share the story.
Sorry in advance as i am by no means a professional story teller, but i hope the community likes it and shares their own stories of sex.
I met a closet sissy on Reddit about 6 months ago. We had chatted for quite some time off and on via kik. Mostly sexting, some role play, some pic exchanges, and light fantasy sharing... I am a very dominant male, but I had never been with a sissy before. And with her being very closeted, we really had no intentions of tmy being more then an internet thing.
But after about 3 months of cyerbering, I finally felt it was time to fuck her in person... But I knew she would need to get ready for it.
I began by giving her more rules. First it was â€œno masturbating unless dressed as a sissyâ€.
After a week or 2, I added the rule â€œno masturbating unless you eat every drop of cum when done.â€
Finally I talker her into locking her clitty and mailing me the key.
Then after about a month locked up I got tmy text message. â€œSir, as requested I have recently been dressing up daily. I have been masturbating my sissy ass/pussy till my clitty drips and licking every drop up. Maybe its time I know what a real man's cum tastes like? I know you want it. To take away any manhood I have left by putting your hard cock in me. I want to cum so bad to something other than a dildoâ€
I had arranged a meeting for us at a hotel. Surprisingly I was nervous but at the same time so aroused. I have fucked women before, tied them up, used them, but never taken away the manhood of a sissy before... The thought made my heart pound and cock hard!
I checked in, and texted the room number. She arrived fully dressed as instructed. I invited her in and guided her to the bed were I sat down. There I told her to stand in front of me and slowly turn around, I wanted to see the whole outfit. The poor thing was breathing hard and her hands were shaky. But she looked amazing. Pink high heals, a short black skirt, and a cute t-shirt with glitter that said â€œslutâ€ on it.
All I could feel is pure sexual arousal and I didn't bother to hide it. I motioned for her to come over to me and hike up her skirt. A small G-string barely covered her pink chastity cage. I smiled and leaned in graPost too long. Click here to view the full text.