Cross Dressing

Wigs, eyeliner, pantyhose and heels! They're not just for women anymore and they haven't been for a while. Cross dressing is taboo, it's fun, it's controversial, it's erotic and it's a hidden gem among thousands of internet porn sites. We really wish there were more to enjoy, especially when there's so much to get excited about. As one of the most versatile porn genres out there, the sites in our Cross Dressing category offer so much to any fan of men in women's clothing. Watch hard bodied hunks strip down to nothing but a pair of lacy women's panties and jerk off, watch pretty boys in stilettos seduce straight men, or watch sissy guys lift up that short skirt and take a big, thick cock. On these websites, you can indulge in all of your hottest and most forbidden fantasies, from lingerie to lipstick and anything in between.

All Cross Dressing Sites

5 sites

My Humble Sissy

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Men in Pantyhose

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Gay Sissies

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Gay Like Girl

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Big Dick Girls

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Cross Dressing Free Galleries

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325 galleries

Gallery	Site	Date
Wearing a black see-thru dress with a string of pearl...	My Humble Sissy, My Humble Sissy	10/18/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	10/18/10
Dena crawls to her boy-lover dressed in her fav strip...	My Humble Sissy, My Humble Sissy	10/17/10
Patrick keeps pushing off his pesky sissy lover who h...	My Humble Sissy, My Humble Sissy	10/17/10
Coming back after a weekly business trip, Keith surpr...	My Humble Sissy, My Humble Sissy	10/17/10
Dena crawls to her boy-lover dressed in her fav strip...	My Humble Sissy, My Humble Sissy	10/17/10
Always hungry for a cock sissy Stephanie was ready to...	My Humble Sissy, My Humble Sissy	10/15/10
Sissy Monica prepares a big surprise for her boyfrien...	My Humble Sissy, My Humble Sissy	10/15/10
Tall and slim sissy Veronica dresses up for her boyfr...	My Humble Sissy, My Humble Sissy	10/14/10
Hilary puts on her fav blonde wig, thong and suspende...	My Humble Sissy, My Humble Sissy	10/13/10
Kinky Melissa indulges her cross-dressing kinks with ...	My Humble Sissy, My Humble Sissy	10/12/10
Hilary puts on her fav blonde wig, thong and suspende...	My Humble Sissy, My Humble Sissy	10/12/10
Naughty Dena wakes up her sleeping boyfriend eager to...	My Humble Sissy, My Humble Sissy	10/11/10
Melissa went on the prowl wearing her smashing red bl...	My Humble Sissy, My Humble Sissy	10/09/10
Wearing a black see-thru dress with a string of pearl...	My Humble Sissy, My Humble Sissy	10/07/10
Patrick feels like going for role play with his sissy...	My Humble Sissy, My Humble Sissy	10/02/10
Caught applying make-up and dressed up like a girl, t...	My Humble Sissy, My Humble Sissy	09/30/10
This sissy has a strong penchant for dresses, panties...	My Humble Sissy, My Humble Sissy	09/29/10
Dressed like Daphne from the popular movie	My Humble Sissy, My Humble Sissy	09/27/10
Unable to choose what to wear, sissified Dennis was l...	My Humble Sissy, My Humble Sissy	09/26/10
Hilary puts on her fav blonde wig, thong and suspende...	My Humble Sissy, My Humble Sissy	09/26/10
Grant treats crossdressed Veronica like his obedient ...	My Humble Sissy, My Humble Sissy	09/25/10
Wearing a black see-thru dress with a string of pearl...	My Humble Sissy, My Humble Sissy	09/24/10
Patrick feels like going for role play with his sissy...	My Humble Sissy, My Humble Sissy	09/23/10
Naughty Dena wakes up her sleeping boyfriend eager to...	My Humble Sissy, My Humble Sissy	09/22/10
Naughty Dena wakes up her sleeping boyfriend eager to...	My Humble Sissy, My Humble Sissy	09/21/10
Wearing just a little apron and a bra, this sissy was...	My Humble Sissy, My Humble Sissy	09/20/10
Sissy Veronica dresses up as a maid, with a little re...	My Humble Sissy, My Humble Sissy	09/20/10
Richmond finds his sissy lover dressed as a girl and ...	My Humble Sissy, My Humble Sissy	09/20/10
Dressed like Daphne from the popular movie	My Humble Sissy, My Humble Sissy	09/19/10
Wearing a long-haired wig with female pants and a blo...	My Humble Sissy, My Humble Sissy	09/19/10
Lying in his pajama on the bed Felix was upset and an...	My Humble Sissy, My Humble Sissy	09/18/10
Melissa asks Felix to bring her a report, surprising ...	My Humble Sissy, My Humble Sissy	09/16/10
Hilary puts on her fav blonde wig, thong and suspende...	My Humble Sissy, My Humble Sissy	09/14/10
Patrick doesn�t like Dena�s dress and hairdo, ang...	My Humble Sissy, My Humble Sissy	09/12/10
Naughty Dena wakes up her sleeping boyfriend eager to...	My Humble Sissy, My Humble Sissy	09/10/10
Richmond finds his sissy lover dressed as a girl and ...	My Humble Sissy, My Humble Sissy	09/09/10
Unable to choose what to wear, sissified Dennis was l...	My Humble Sissy, My Humble Sissy	09/06/10
Taking this sissified guy for a girl, Kadeem stopped ...	My Humble Sissy, My Humble Sissy	09/05/10
Coming back after a weekly business trip, Keith surpr...	My Humble Sissy, My Humble Sissy	09/04/10
Wearing a black see-thru dress with a string of pearl...	My Humble Sissy, My Humble Sissy	09/04/10
Anna would let Richmond wipe his boots on her provide...	My Humble Sissy, My Humble Sissy	09/04/10
Dressed up in a classy French maid's outfit topped wi...	My Humble Sissy, My Humble Sissy	09/02/10
Dressed like Daphne from the popular movie	My Humble Sissy, My Humble Sissy	09/01/10
Felix was still in his pajamas when dolled-up sissy J...	My Humble Sissy, My Humble Sissy	08/31/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	08/31/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	08/29/10
Wearing just a little apron and a bra, this sissy was...	My Humble Sissy, My Humble Sissy	08/29/10
Keith believes that some M2F role playing can spice u...	My Humble Sissy, My Humble Sissy	08/28/10
Wearing a long-haired wig with female pants and a blo...	My Humble Sissy, My Humble Sissy	08/27/10
Sissy Veronica dresses up as a maid, with a little re...	My Humble Sissy, My Humble Sissy	08/26/10
Taking this sissified guy for a girl, Kadeem stopped ...	My Humble Sissy, My Humble Sissy	08/25/10
Tall and slim sissy Veronica dresses up for her boyfr...	My Humble Sissy, My Humble Sissy	08/23/10
Wearing a long-haired wig with female pants and a blo...	My Humble Sissy, My Humble Sissy	08/20/10
Kinky Melissa indulges her cross-dressing kinks with ...	My Humble Sissy, My Humble Sissy	08/19/10
Kinky Melissa indulges her cross-dressing kinks with ...	My Humble Sissy, My Humble Sissy	08/18/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	08/18/10
Kadeem couldn't understand why his boyfriend should w...	My Humble Sissy, My Humble Sissy	08/18/10
A wigged sissy in a bright red dress comes downstairs...	My Humble Sissy, My Humble Sissy	08/15/10
Wearing a long-haired wig with female pants and a blo...	My Humble Sissy, My Humble Sissy	08/15/10
Pissed off with his friend�s slutty looks, Richmond...	My Humble Sissy, My Humble Sissy	08/15/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	08/12/10
Dressed up in a classy French maid's outfit topped wi...	My Humble Sissy, My Humble Sissy	08/06/10
Kinky Melissa indulges her cross-dressing kinks with ...	My Humble Sissy, My Humble Sissy	08/06/10
Keith believes that some M2F role playing can spice u...	My Humble Sissy, My Humble Sissy	08/04/10
Wearing his yellow blouse with an ultra mini and foot...	My Humble Sissy, My Humble Sissy	08/04/10
This sissy has a strong penchant for dresses, panties...	My Humble Sissy, My Humble Sissy	08/03/10
This sissy has a strong penchant for dresses, panties...	My Humble Sissy, My Humble Sissy	08/02/10
Patrick keeps pushing off his pesky sissy lover who h...	My Humble Sissy, My Humble Sissy	08/02/10
Melissa really startles cute boy Felix with her girli...	My Humble Sissy, My Humble Sissy	08/01/10
Kinky Melissa indulges her cross-dressing kinks with ...	My Humble Sissy, My Humble Sissy	07/29/10
Melissa asks Felix to bring her a report, surprising ...	My Humble Sissy, My Humble Sissy	07/29/10
Shocked with his lover's girly looks, Clive starts sh...	My Humble Sissy, My Humble Sissy	07/29/10
Unable to choose what to wear, sissified Dennis was l...	My Humble Sissy, My Humble Sissy	07/26/10
Wearing a long-haired wig with female pants and a blo...	My Humble Sissy, My Humble Sissy	07/25/10
Richmond finds his sissy lover dressed as a girl and ...	My Humble Sissy, My Humble Sissy	07/24/10
Melissa asks Felix to bring her a report, surprising ...	My Humble Sissy, My Humble Sissy	07/23/10
Unable to choose what to wear, sissified Dennis was l...	My Humble Sissy, My Humble Sissy	07/23/10
On seeing this sissy wearing hair-curlers and a night...	My Humble Sissy, My Humble Sissy	07/21/10
Surprised with his boyfriend's new looks Kevin begins...	My Humble Sissy, My Humble Sissy	07/19/10
Dena crawls to her boy-lover dressed in her fav strip...	My Humble Sissy, My Humble Sissy	07/17/10
Patrick feels like going for role play with his sissy...	My Humble Sissy, My Humble Sissy	07/17/10
Wearing just a little apron and a bra, this sissy was...	My Humble Sissy, My Humble Sissy	07/17/10
Wearing a long-haired wig with female pants and a blo...	My Humble Sissy, My Humble Sissy	07/16/10
Grant treats crossdressed Veronica like his obedient ...	My Humble Sissy, My Humble Sissy	07/16/10
Hilary puts on her fav blonde wig, thong and suspende...	My Humble Sissy, My Humble Sissy	07/14/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	07/14/10
Unable to choose what to wear, sissified Dennis was l...	My Humble Sissy, My Humble Sissy	07/12/10
Wearing his yellow blouse with an ultra mini and foot...	My Humble Sissy, My Humble Sissy	07/08/10
Anna would let Richmond wipe his boots on her provide...	My Humble Sissy, My Humble Sissy	07/08/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	07/07/10
Sissy Monica prepares a big surprise for her boyfrien...	My Humble Sissy, My Humble Sissy	07/07/10
Sissified housemaker Joan was jerking off in the bath...	My Humble Sissy, My Humble Sissy	07/06/10
A wigged sissy in a bright red dress comes downstairs...	My Humble Sissy, My Humble Sissy	07/03/10
Naughty Dena wakes up her sleeping boyfriend eager to...	My Humble Sissy, My Humble Sissy	07/03/10
Strutting before Kadeem in this glamorous female outf...	My Humble Sissy, My Humble Sissy	06/30/10
Kinky Melissa indulges her cross-dressing kinks with ...	My Humble Sissy, My Humble Sissy	06/28/10
Dressed up like an office girl in a white blouse and ...	My Humble Sissy, My Humble Sissy	06/28/10
Grant treats crossdressed Veronica like his obedient ...	My Humble Sissy, My Humble Sissy	06/27/10
This sissy has a strong penchant for dresses, panties...	My Humble Sissy, My Humble Sissy	06/27/10

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