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Archive for 'Cum Filled Mouth'

Female Clothed Sissy Boy gets his Ass Fucked

December 19, 2012

Sissy Boy Silvester looks like a nerdy girl on her first day, what with his glasses, pretty dress, black nylons and spike heels. After a few cocktails he and Jacob get drunk and ready to get dirty, and they start it off with mouth-to-mouth kisses. Then Jacob gets bolder and starts feeling up his sissy [...]

Maurice Gets Some Awesome Cross Dresser Sex

October 18, 2010

Maurice always fantasied that he had pounded that transvestite ass of Ralph’s. They both knew what to do with a hard thick cock and when one of the sissy boys put on a dress and wig the action got hot. That tight crossdresser ass hole was rimmed wide open as he started fucking the [...]

Sissy Crossdresser Seduces Straight Male Freind

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 [...]

Crossdressing Sissy Boy gets a Cum Facial

June 9, 2009

In this scene from The Crossdressers when this gay boy named Carl came home, he found his boyfriend Steve waiting for him, but this time he was all dressed up just like a smutty babe. He was wearing a wig, skirt, bra and panties. He had to admit that seeing Steve like that really turned [...]

Sexy Tranny Finds a Sissy Boy Trying on Her Frock

March 7, 2009

This horny shemale named Jo found this sissy boy outside her house trying on her clean pink panties! Well you can be sure that she knew exactly what to do with him. She snatched the thong panties that he had sliped on and gave them a pull! This caused a deep wedgie. Jo then sat [...]

Horny Crossdressing Slut Takes On Two Lucky Guys

February 23, 2009

In this scorching scene from The Cross dressers this horny sissy boy has been secretly dressing up as a woman in the safety of his own house for years. He has ventured out to the mailbox a few times in the middle of the night, even walked the dog around the block in a tight [...]

Cory the Horny CrossDresser gets Fucked In The Ass

November 6, 2008

It is Halloween again but this is not some costume that this sissy boy Cory put on just because of the holiday. Cory likes to go out to gay bars all year round dressed up as a woman. Tonight, he was out at one of his favorite places, a place where there is always horny [...]

Sissy Boy Sucked by Two Cross Dressers

August 29, 2008

This sissy boy had no idea what he was getting into when he knocked on this door last night. He was answering an ad in the local newspaper and after talking to the ‘girl’ on the phone he decided to head over. Her voice sounded a little weird on the phone and in person her [...]

Sissy Cross Dresser gets picked up at a party

August 22, 2008

Over at The Cross Dressers the other night these party boys two came across this cross dressing charming sissy boy at a club. Even before he took the whig off, they knew that she was really a he. But that’s alright, that’s exactly what they were looking for. They were looking for someone to use [...]