Cross-dressing phone sex

Cross-dressing phone sex humiliation

I have a caller who likes to do humiliation and cross-dressing phone sex calls with me. Now some cross-dressers are into “passing,” That is they try to look as much like a woman as possible. And some really do. I’ve seen some callers almost magically turn themselves into beautiful, feminine women.

cross-dressing phone sex caller dresses up like Tinkerbell

Mature MILF Mattie’s cross-dressing phone sex caller dresses up like Tinkerbell

Not so with this cross-dressing phone sex caller. He prefers to be as ludicrous as possible. And for good reason. The sillier he looks and acts, the more I humiliate and tease him.

You can not imagine how much I laughed and laughed at this. “Tinkerbell” was my little bitch faggot fairy as you can imagine. Even more amusing, he had two of his blowup dolls to fuck for me while we were on the phone.

And so I spent an hour and a half humiliating my little Tinkerbell. Why?  Because he’s short, and he has a pathetic useless tiny dick. Even his stepmother and stepsisters are taller than him, and they all look down on him. Literally. And the best he can do is to dress up in some ludicrous costume that makes him look even more pathetic. And call a MILF that will humiliate him.

There is also a very embarrassing story my little Tinkerbell confessed to me about not being able to get a loan because of charging his cross-dressing phone sex calls  to his business account. But that is another story. I want to make sure I go into as much humiliating depth for that one as possible 😉

Are you a little sissy cross-dressing phone sex caller that gets into feminization, phone sex humiliation and small penis humiliation? Then you should give me a call!

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2 Comments:

  1. I want to be totally feminized

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