Crossdresser Goes On Grindr

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Permanently sissified.
757 words
4.31
29.5k
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For years I fought the desires to crossdress and have sex with men and pretended I was straight in public and in both my marriages. But the urges were so strong I would occasionally secretly crossdress whenever I could and even sneak out and have gay experiences. Now, that I am divorced again and single I have decided I will only ever have sex dressed as a slutty girl.

I bit the bullet one night and created a Grindr account and placed an ad. None of the responses excited me but then all of a sudden one came in that instantly made my sissy clit rockhard and my heart start beating really fast because I somehow immediately knew I was going to have sex with that person that very night!

I didn't care what the risks were anymore and after talking to him for a few minutes I said I was willing to let him come over and gave him my address. An hour later after dressing as slutty as I could I was nervously letting him into my apartment.

At first he was really nice. He told me to stand in front of him while he inspected me from head to toe and kept saying how sexy and cute I was and what a good girl I was. He kept touching me all over with his big hands and when he rougly grabbed my sissy clit and pulled me to him and started french kissing me I completely melted.

He made me kiss him for a really long time. I could not believe I was actually french kissing a man. He pushed his tongue deep into my mouth and I just blissfully sucked on it and swallowed his spit while my eyes rolled back in my head.

Next thing I knew, he became aggressive and threw me on the bed and pulled my skirt up and panties down and started spanking my ass really hard. He told me this is what happens to girls like me. While he was spanking my ass he told me to take his cock out and suck it and I immediately did. I wasn't going to argue with anything he was going to tell me to do because I was scared.

Once I got my mouth onto his cock he sat back and just thoroughly enjoyed it for like 15 minutes. He kept calling me such a good little sissy slut and telling me he was going to turn me into a cock-crazed whore. Then he pulled out poppers and put it under my nose and made me inhale deep and the next 30 minutes were an incredible blur of me getting totally used.

He roughly put me on my hands and knees and put some lotion on his bare cock and slowly slid it into my virgin ass and fucked me while spanking me. I loved the sounds he made while he fucked me and I could not help whimpering like a little sissy bitch. It was absolutely the happiest I ever felt.

Finally, he said he was going to cum and I told him I wanted it on my face and in my mouth and he grabbed me by the hair and shoved me on the ground and started jacking his cock right in my face. As he started to cum, I told him to turn me into a cocksucking whore for life and he said I wasn't the first sissy bitch he had done that to and that he's been turning bitches like me out since back in the day.

He laughed while he was cumming all over my face and in my mouth and he made me swallow every last drop and then he spit on my face, got dressed, and told me to fuck off when he left. I blissfully fell asleep with a cum-coated throat and his dried cum all over my face feeling like a completely used degraded sissy whore and when I got up the next morning and looked in the mirror my gay sissy tits were all bruised and sore to the touch and it made me so wildly horny again when I touched them.

I immediately knew that he had permanently turned me into a complete sissy whore and that I was now going to do anything for any man and would never be with a woman ever again. I now live in a constant state of horniness wishing he would contact me again and take complete control of my life.

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AnonymousAnonymous12 months ago

I absolutely love this story I just wish you would write more, it reminds me of my first time with my master I was on my knees sucking his beautiful cock in under twenty minutes of Meeting him then when he recovered he took my sissy pussy and I was his for life xxx sissy Lucy

AnonymousAnonymousabout 1 year ago

Great story you should continue it!

AnonymousAnonymousabout 1 year ago

I believe the other comment was to say brevity, to which I agree.

Simply cannot be bothered with much beyond a page, page of paper . . . Page boy, that's different.

madetoobeymadetoobeyabout 1 year ago

Full marks for bevity.

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