Any Crossdressers here?

Scott8361

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I have a married guy I service through a glory hole I set up for him. He looks at hetero porn on his phone as I suck him to climax.

I often thought about cross dressing in a sexy outfit with stockings, heels, wig, etc. to be able to forgo the glory hole. I haven't brought up the idea to him yet.

But maybe it could lead to more than me just blowing him. I would like to bend over and have him rub his hard cock between my ass cheeks while wearing a thong and stockings... maybe get him to actually slide it in, grab my hips, and fuck me! Shooting his load into me!

I have a wish list created on Amazon of sexy things to wear, wigs, even prosthetic breasts, to see if I could pull of a decent look! But I haven't made the move to actually purchase them yet!

I think I have the legs and ass to possibly pull it off. Tell me what you think?
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Mister2101

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I have a married guy I service through a glory hole I set up for him. He looks at hetero porn on his phone as I suck him to climax.

I often thought about cross dressing in a sexy outfit with stockings, heels, wig, etc. to be able to forgo the glory hole. I haven't brought up the idea to him yet.

But maybe it could lead to more than me just blowing him. I would like to bend over and have him rub his hard cock between my ass cheeks while wearing a thong and stockings... maybe get him to actually slide it in, grab my hips, and fuck me! Shooting his load into me!

I have a wish list created on Amazon of sexy things to wear, wigs, even prosthetic breasts, to see if I could pull of a decent look! But I haven't made the move to actually purchase them yet!

I think I have the legs and ass to possibly pull it off. Tell me what you think?
View attachment 15551011
View attachment 15551031
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I have a married guy I service through a glory hole I set up for him. He looks at hetero porn on his phone as I suck him to climax.

I often thought about cross dressing in a sexy outfit with stockings, heels, wig, etc. to be able to forgo the glory hole. I haven't brought up the idea to him yet.

But maybe it could lead to more than me just blowing him. I would like to bend over and have him rub his hard cock between my ass cheeks while wearing a thong and stockings... maybe get him to actually slide it in, grab my hips, and fuck me! Shooting his load into me!

I have a wish list created on Amazon of sexy things to wear, wigs, even prosthetic breasts, to see if I could pull of a decent look! But I haven't made the move to actually purchase them yet!

I think I have the legs and ass to possibly pull it off. Tell me what you think?
View attachment 15551011
View attachment 15551031
You have a very sexy body my friend. I would love to see you in a pair of yellow silky, lacy women's sting bikini panties.....
 

Swordmonkey

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How did she feel about it?

Well it was her idea, she'd asked a few times before. I don't think she noticed how hard I was though. :p

I do want her to do my full face one time, but I don't know if that would freak her out too much or not.
 
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Capers

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Cool, next time ask her if she likes it, if she does tell her to do whatever she wants as far as putting more on. Play hard to get and tell her she only has one chance and your not going to let her do it again. When she's done you could initiate some sexual action, even if it is just making out with her, and see how she reacts. Good luck!
 

Swordmonkey

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Cool, next time ask her if she likes it, if she does tell her to do whatever she wants as far as putting more on. Play hard to get and tell her she only has one chance and your not going to let her do it again. When she's done you could initiate some sexual action, even if it is just making out with her, and see how she reacts. Good luck!

That's actually a great idea, I'll try it. :D
 
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