https://www.429men.com/tags/sissi/ Mon 02 Nov 2026 04:38:14 +0200 https://www.429men.com/videos/477766/hairy-ass-action-a-crossdresser-s-f-cking-session/
Imagine you've always wanted to try a man's anus, but you don't want to be seen as gay. What do you do? The best thing to do is like this guy pleasuring his gay friend, who's wearing women's underwear and a wig. He's trying to impersonate a woman, but it doesn't quite work because his anus isn't shaved, and the man is generally quite hairy. Still, it's entertaining to watch the crossdresser being pleasured by his friend without a condom. ]]> Wed 21 Oct 2026 07:07:41 +0200 https://www.429men.com/videos/477766/hairy-ass-action-a-crossdresser-s-f-cking-session/ https://www.429men.com/videos/483492/delicate-crossdresser-chooses-unprotected-pleasure/
The delicate man has dressed up as a woman. He's wearing women's underwear and a red wig; he's a real crossdresser. His boyfriend will like it, because he likes very feminine men. But without the women's underwear, he'd probably be very feminine too, because he really is very delicate. During sex, however, he knows how to get a bit more kinky and a bit wilder, which is why he also leaves out the condom. His boyfriend likes that, and he fucks the young man without a condom until he finally ejaculates in his mouth. ]]> Sun 18 Oct 2026 00:11:55 +0200 https://www.429men.com/videos/483492/delicate-crossdresser-chooses-unprotected-pleasure/ 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/483970/daring-gay-crossdresser-gets-fucked-while-wearing-just-his-bra/
The two gay men enjoy having fun, and sometimes the hairy, slim man dresses up as a woman. So it happens that the gay crossdresser wears not only a bra during sex, but also his blonde wig. His gay buddy likes this, but obviously, and without a condom, he fucks his friend's hairy asshole before finally ejaculating all his sperm into the slim gay man's mouth. ]]> Wed 16 Sep 2026 20:17:36 +0200 https://www.429men.com/videos/483970/daring-gay-crossdresser-gets-fucked-while-wearing-just-his-bra/ 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/