Written on March 22, 2010
You know this is not the first time that this sissy boy has had sex with other men, but it is the first time he has gone out in public dressed like a woman to find them. He has crossdressed at home hundreds of time, but tonight, he finally worked up the courage to go out in public dressed in from head to toe as a woman. Just that was a turn on for him, meeting a boy to take home made it even better.
The lucky guy the sissy boy had picked up has never had sex with another man before. Luckily our sissy boy is more than willing to be his teacher to the pleasures of gay sex. The sissy is soon stripping his friend out of his clothes and going to work on the lucky guys hard cock. The real fun cums when the crossdresser pulls up his skirt and invites the boy to come fuck his ass. He takes one look at the puckered fuck hole and pushes his throbbing cock in with the sissy boy laying on her side. The sissy wants to be fucked really hare so he gets up on her knees so that the boy can take her doggy style. He fucks the sissy like this until he can feel the jism well up in the tip of his cock. Then he pulls out and shoots his cum into the sissy’s open mouth.