https://www.429men.com/tags/crossdresser/ Mon 12 Oct 2026 21:54:38 +0200 https://www.429men.com/videos/486180/raw-desire-an-ugly-crossdresser-s-unfiltered-experience/
The crossdresser isn't exactly a looker; you could almost say he's rather ugly. But his gay friend doesn't seem to care at all, because all he cares about is being able to fuck his hairy asshole without a condom. The Sissi slut is obviously having fun too, because while he's wearing a blonde wig and a feather boa around his neck, he spreads his legs to let her fuck his partially shaved asshole during gay sex. ]]> Thu 01 Oct 2026 13:36:11 +0200 https://www.429men.com/videos/486180/raw-desire-an-ugly-crossdresser-s-unfiltered-experience/ https://www.429men.com/videos/477837/red-wigged-crossdresser-faces-a-fiery-f-cking/
The crossdresser is a gay man wearing a red wig. His outfit is completed with women's underwear and a feather boa around his neck. The slightly chubby man clearly enjoys dressing like a woman in order to enjoy gay sex. Naturally, the two gay men forgo condoms, as a crossdresser's anus must be felt bare. The man in women's underwear obviously enjoys playing the role of Sissi and then receiving a cumshot in his mouth. ]]> Tue 29 Sep 2026 00:35:30 +0200 https://www.429men.com/videos/477837/red-wigged-crossdresser-faces-a-fiery-f-cking/ https://www.429men.com/videos/482043/crossdresser-delivers-unforgettable-pleasure-to-a-hairy-gay-lover/
The gay crossdresser in a blond wig gets a good fucking from his boyfriend and then receives a cumshot in his mouth. The guy obviously enjoys getting the semen in his mouth and trying to swallow it. So it happens that the two gay men fuck exclusively without a condom and then both ejaculate. That's what happens when you fuck a crossdresser who also happens to be gay. ]]> Sat 19 Sep 2026 02:32:49 +0200 https://www.429men.com/videos/482043/crossdresser-delivers-unforgettable-pleasure-to-a-hairy-gay-lover/ https://www.429men.com/videos/483473/daring-gay-dwt-experiences-intense-pleasure-in-a-hot-session/
The two gay men, of course, only have sex without a condom. But one of them is wearing women's underwear and a wig. The other gay man finds this quite appealing and has sex with the man in the women's underwear without a condom, which the other gay man obviously enjoys very much. So it happens that the two gay friends have sex and enjoy it without a condom. When the man can't hold back any longer, he ejaculates all his semen into his friend's mouth. ]]> Wed 16 Sep 2026 09:22:22 +0200 https://www.429men.com/videos/483473/daring-gay-dwt-experiences-intense-pleasure-in-a-hot-session/ https://www.429men.com/videos/481868/wigged-out-a-gay-man-s-wild-bedroom-escapade/
The two gay men are having sex. However, for one of them, it must feel like he's having sex with a woman. The slim gay man is wearing a red wig and women's lingerie, including a bra and high heels. He's a real crossdresser and loves wearing his wig and women's lingerie during sex. The "Sissi Bitch" lets him have sex with her without a condom and then gets a cumshot in her mouth from her gay boyfriend, which the gay man, of course, swallows. ]]> Sun 13 Sep 2026 20:34:20 +0200 https://www.429men.com/videos/481868/wigged-out-a-gay-man-s-wild-bedroom-escapade/ https://www.429men.com/videos/380378/femboy-from-outaspace-is-very-horny-suck-and-fuck-on-earth/
Femboy from outaspace is very horny suck and fuck on earth ]]> Fri 27 Feb 2026 17:59:19 +0200 https://www.429men.com/videos/380378/femboy-from-outaspace-is-very-horny-suck-and-fuck-on-earth/ https://www.429men.com/videos/328931/worship-my-shemale-gf-balls/
]]> Wed 25 Feb 2026 04:02:57 +0200 https://www.429men.com/videos/328931/worship-my-shemale-gf-balls/ https://www.429men.com/videos/228301/sissy-bimbo-training/
]]> Tue 24 Feb 2026 16:01:15 +0200 https://www.429men.com/videos/228301/sissy-bimbo-training/ https://www.429men.com/videos/343643/blonde-transgender-pumps-her-dick-in-ebony-stockings/
]]> Mon 23 Feb 2026 04:31:54 +0200 https://www.429men.com/videos/343643/blonde-transgender-pumps-her-dick-in-ebony-stockings/ https://www.429men.com/videos/388796/young-tranny-masturbates-in-ebony-stockings/
]]> Sun 15 Feb 2026 09:07:18 +0200 https://www.429men.com/videos/388796/young-tranny-masturbates-in-ebony-stockings/ https://www.429men.com/videos/373774/crossdresser-fucked-by-hung-tranny-gracie-jane/
Gorgeous blonde Gracie Jane is tired of her roommate Tony Orlando acting like her being a woman means she owes him something. Commanding the room in black leather and mesh, Gracie is having none of Tony's bullshit. She decides that it's time for him to walk a mile in her high heels by dressing him up in some lingerie and sissifying him into her pretty and perfect sex toy. Gracie rides Tony all over the bedroom, drilling him deep until he's really internalized all of her lessons about girl power in this fiery feminization domination scene. ]]> Wed 11 Feb 2026 22:48:03 +0200 https://www.429men.com/videos/373774/crossdresser-fucked-by-hung-tranny-gracie-jane/ https://www.429men.com/videos/242837/crossdresser-denny-leon-playing-with-her-ass-meat/
]]> Thu 05 Feb 2026 12:31:37 +0200 https://www.429men.com/videos/242837/crossdresser-denny-leon-playing-with-her-ass-meat/