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 grabbing the cage kissed her. I had grand thoughts of teasing her for a long while. See if I could make her sissy cage feel tighter then it ever had before. But I gave into my first instinct and pushed her to her knees. It seems that is where her mind went to, as the first thing she did was open her mouth for me.
I pulled out my cock knowing full well this was the first time she has ever seen a cock like this in real life. I saw my precum oozing out of the tip of my cock. She hesitated and just sat there looking at it biting her lower lip. But when I said "suck my cock, sissy" she snapped out of her little trance and took it all in one motion.
I grabbed the back of her head and started fucking her mouth like a pussy. I could feel my cock getting bigger in her mouth. It turned me on so much knowing this was her first time sucking a
cock. I even whispered to her, asking her how it feels to have a man use her mouth like a fleshlight... Her only response was gagging and gasping, but I kept on fucking her mouth.
Eventually I pulled her head off of my cock. She was breathing hard, spit dripping from her mouth, eyes a bit watery, and I said â€œgood sissyâ€ as I laid her on her stomach.
She pulled the g-string to the side, as I spit on her ass hole. I said, "I can tell you like it bitch by the precum dripping from your small, sissy cock." Her only response was "Mmm, please fuck me sir, I need to be fucked like a real girl."
I could almost read her mind. The look on her face said it all. She couldn't believe she was about to take another man's cock in her ass. I told her â€œthere was no going back... Once you get fucked you are going to be a sissy forever...â€
She gave a small nod and that was all I needed to push in. She let out a gasp and whimper. I grabbed her hips and thrust hard into that ass. Part of me wondered if I should have got lube but my dominance over her made me uncontI AM A STUPID FUCKWIT AND I DESERVE TO DIE!ably horny. I just couldn't stop fucking her.
After a few minutes she began begging to be fucked harder. As soon as I hear that I pushed all
my weight on her. She collapses from doggy style to flat on her stomach unable to move. My cock was going deeper than before. Fucking her with everything I had I just whispered over and over, "you are my bitch now.â€
Eventually I got to the point of no return. My pleasure was too much. At the last second I pulled out, I AM A STUPID FUCKWIT AND I DESERVE TO DIE!ed her over and sprayed one of the biggest loads I have ever made all over her sissy face...
Breathless and exhausted she laid there with a far off look in her eyes and a small smile on her cum drenched face. In all the excitement I never unlocked her, and I could see lots of liqied draining from her small cage... She didn't seem to care, so I just told her, â€œmaybe I will unlock you next timeâ€. I then went into the bathroom to shower. When I got out she was gone. A text on my phone saying â€œthank you sir, may we do this again?â€
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