https://www.thepornstar.com/tags/pain-anal2/ Mon 18 May 2026 08:39:39 +0200 https://www.thepornstar.com/videos/102435/redhead-keisha-grey-wants-her-face-painted-with-jizz-after-anal-sex/
Curly redhead pornstar Keisha Grey does what she does best: Riding a cock, getting her asshole stretched and begging for cum on her face. ]]> Sat 21 Jun 2025 17:36:39 +0200 https://www.thepornstar.com/videos/102435/redhead-keisha-grey-wants-her-face-painted-with-jizz-after-anal-sex/ https://www.thepornstar.com/videos/137230/stuffing-her-asshole-in-the-kitchen/
They talked about it, they wanted it and now they are finally doing it. These horny teens try anal sex for the very first time and they are so excited about it they don't even make it to the bedroom. Just getting naked and fucking right in the kitchen makes the whole experience even more unusual and satisfying on every level. Alice never felt so good and even some pain during the first anal penetration felt like something she could turn into pleasure to make her orgasm even more powerful. ]]> Sun 08 Jun 2025 10:15:55 +0200 https://www.thepornstar.com/videos/137230/stuffing-her-asshole-in-the-kitchen/ https://www.thepornstar.com/videos/101867/sweet-teen-iza-loves-some-sensual-ass-fucking-in-the-afternoon/
Russian teen Iza and her boyfriend Nikolas are a passionate young couple that loves experimenting and so far they have found out that anal is neither taboo, nor painful as people think it is. In fact Iza loves Nik's dick up her tight little asshole, because she knows that gives him extra pleasure! Of course for a devoted girlfriend like her the best reward at the end of a fuck session is a hot sticky load on her face! ]]> Thu 05 Jun 2025 17:16:25 +0200 https://www.thepornstar.com/videos/101867/sweet-teen-iza-loves-some-sensual-ass-fucking-in-the-afternoon/ https://www.thepornstar.com/videos/342337/bad-girl-have-anal-sex/
You've always heard that bad girls are the ones willing to have anal sex. Yes, they love painful anal fuck. ]]> Thu 15 May 2025 22:23:59 +0200 https://www.thepornstar.com/videos/342337/bad-girl-have-anal-sex/ https://www.thepornstar.com/videos/46657/bianca-s-painful-interracial-debut/
Yep, that's not a scream of pure sexual euphoria, thats also a bit of massive cock-induced anal trauma that you can hear in some of her moans. Not that that would stop Bianca, she's a warrior through and through! ]]> Sun 04 May 2025 15:44:46 +0200 https://www.thepornstar.com/videos/46657/bianca-s-painful-interracial-debut/ https://www.thepornstar.com/videos/62878/obedient-teen-crams-an-entire-cock-into-her-gaping-anus/
She thought taking cock in the ass would be really painful, but look at her now! She does some nasty ass-riding with a happy smile on her face and takes some more anal drilling in other cool positions. You go girl! ]]> Mon 28 Apr 2025 19:21:33 +0200 https://www.thepornstar.com/videos/62878/obedient-teen-crams-an-entire-cock-into-her-gaping-anus/ https://www.thepornstar.com/videos/142028/petite-nerd-sasha-sparrow-is-a-secret-anal-slut/
Stepsisters are a pain but yours is beautiful but she's a real nerd! You want in on that pussy! Innocent and pretty Sasha Sparrow ditches her book and lets you touch her fresh little cunt and strip off her clothes. ]]> Sat 05 Apr 2025 11:30:44 +0200 https://www.thepornstar.com/videos/142028/petite-nerd-sasha-sparrow-is-a-secret-anal-slut/ https://www.thepornstar.com/videos/31518/marta-26-years-old-a-hardcore-sex-fan/
All smiles in the car, Marta, 26, returns for a new spicy adventure! A philosophy professor in Madrid, Spain, this young woman with a captivating smile clearly displays her preference for hardcore practices, which she experiments with regularly. Endowed with undeniable physical assets, such as her generous natural breasts and her plump buttocks, she joins the two stallions who accompany her today, ready to give free rein to her fantasies. Under the spell of Emmanuel and Klem, she lets herself be carried away in a terribly intense session, with the dose of anal she wanted... ]]> Sat 11 Jan 2025 11:22:20 +0200 https://www.thepornstar.com/videos/31518/marta-26-years-old-a-hardcore-sex-fan/ https://www.thepornstar.com/videos/84056/ts-prostitute-juliette-stray-getting-assfucked-painfully-but-she-loves-it/
Juliette Stray arrives to her client's house dressed in sexy lingerie and stockings where Chris waiting for her. Christian makes it clear in the first moments that Juliette wasn't prepared for his size... ]]> Thu 26 Dec 2024 12:18:08 +0200 https://www.thepornstar.com/videos/84056/ts-prostitute-juliette-stray-getting-assfucked-painfully-but-she-loves-it/ https://www.thepornstar.com/videos/186008/brutal-screaming-ass-pumping/
After getting some preparation with a big toy, pretty Sasha stretched her ass for Toby's dick! ]]> Sun 22 Dec 2024 22:54:52 +0200 https://www.thepornstar.com/videos/186008/brutal-screaming-ass-pumping/ https://www.thepornstar.com/videos/87965/trans-women-aubrey-kate-and-chelsea-marie-fuck-pierce-paris/
Evil Angel focuses this hardcore/documentary hybrid on Trans superstar Aubrey Kate. A pansexual XXX threesome, backstage footage and deeply candid interviews reveal a real person coming to terms with her career and her life as porn and mainstream culture come to terms with transsexuality. Gorgeous, platinum blonde Aubrey appears to be a perfectly glamorous diva-in-control, but she speaks forthrightly about troubles and pain inherent to adult entertainment: stigmatization of performers, finding friends that aren't out to take advantage, and dating -- she describes the pitfalls of romance both within and ouTranside of the porn industry. Aubrey recounTrans serious depression and recalls her worst experiences (stomach issues while shooting sex, anal surgery) in unflinching language. But she says it's mostly good times on the set, and she approaches each day with an excited, open mind. Aubrey's humor comes through as she talks about learning to display her lust on camera after trying to hide it while growing up in a household crowded with grandparenTrans and aunTrans. She provides graphic detail about erections, taking cock up the ass, the arousing thrill of strangers, and how she geTrans off: 'I need a dick in my mouth or an ass in my face.' Producer Aiden Starr says that she and 'friendly, outgoing, personable' Aubrey connected right away. According to Aubrey, they've developed an unspoken communication on set, and Aiden looks out for her. Aiden notes that cisgender and transgender porn people haven't always mixed, but she's encouraged by a trend toward inclusiveness. Evil Angel made Aubrey the industry's first trans contract performer. Studio founder John Stagliano notes that as sales of Trans porn have increased, 'That freedom of not judging people and not expecting them to fit in little boxes was evolving in society.' He says, 'It's nice to have a big star in the trans business,' adding that Aubrey's qualities allow mainstream people to think differently: 'Being free to express what you get off on is a big deal for people and a big deal for porn.' Trans star Chelsea Marie and heavily hung stud Pierce Paris join Aubrey in a threesome directed by Aiden. 'I wanted it to be very trans-pride,' says Aubrey, so the colors of the trans flag are prominent in the scene: Aubrey and Chelsea tease and stretch on a pink-and-blue yoga mat, their long locks braided with those hues. Chelsea's big cock swings; she planTrans her face in Aubrey's hot ass for a rim job. Pierce wears a leather harness and bow tie, his hugely thick prick protruding from his trousers. The busty, tattooed girls shoot lube from dick-and-balls-shaped squirt toys! Limber Aubrey bends backward, taking a blowjob from Aubrey as she gives one to Pierce. Worshipful blowjobs make slobber flow all around. Pierce buttfucks whimpering Aubrey into the mat; Chelsea sodomizes Aubrey as Aubrey and Pierce share 69. Aubrey takes a double-anal reaming, impaling her sphincter on Pierce and Chelsea at once! Chelsea and Pierce's messy cum splashes Aubrey's tiTrans. With Pierce's prick in her mouth, Aubrey masturbates to climax, spraying she-semen. She shows off the 'SLUT' tattoo on her inner lip. ]]> Thu 19 Dec 2024 14:46:38 +0200 https://www.thepornstar.com/videos/87965/trans-women-aubrey-kate-and-chelsea-marie-fuck-pierce-paris/ https://www.thepornstar.com/videos/152973/assfucking-lover-lily-labeau-has-an-amazing-tight-anus/
Lily licks his nut sack and deep-throats his tool; he greases her backdoor and plunges his meat into her, fucking until Lily's rectum gapes widely. ]]> Thu 05 Dec 2024 14:34:04 +0200 https://www.thepornstar.com/videos/152973/assfucking-lover-lily-labeau-has-an-amazing-tight-anus/