/sissy/

Any sissies on Jow Forums?

I'm going to meet up with a man in a hotel room on wednesday. He's going to dress me like a girl wig a wig, make up, lingerie, dress and heels. Then he's going to fuck my brains out. Never did any crossdressing before, let alone anything sexual with a man.

Kind of nervous but also excited. Please share your sissy stories how you became a whore for real men.

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>Never did any crossdressing before, let alone anything sexual with a man
>He's going to dress me like a girl wig a wig, make up, lingerie, dress and heels. Then he's going to fuck my brains out
That's quite a leap you're taking there

>tfw no qt sissy bf who i can put on hrt and turn into my girlfriend
ree

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I've always had that fantasy but never had the chance to dress up because there are always people around me. Posted an ad on cl and got to know a married man who loves sissies and will provide all the stuff I need. Still can't believe I'm actually doing it.

Good for you, kind of jelly actually
I fantasize about something like that too, but clothes cost money, make up is hard and what if there's poop

>Please share your sissy stories how you became a whore for real men.

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I wish I would have been able to be a sissy. Now my only hope is to find a smol sissy to take out my anger on.

>I fantasize about something like that too, but clothes cost money

Yeah that's why I'm so happy he will provide everything I need and I don't need to pay anything or hide it afterwards.

>make up is hard

I know, kind of worried because of that one. I'm most likely going to fuck it up, there is no way you can do make up right on your first time.

>I wish I would have been able to be a sissy.

It's extremely easy to be a sissy, that's what makes it so attractive. You can use all the tricks roasties use in order to be pretty and sexy, then you just relax and let the real man take over.

Not easy to be one that's worthwhile.
I was too tall and masculine. Now I'm too old as well.