https://www.freepornflix.com/categories/crossdresser/ Sun, 19 Apr 2026 14:21:42 UTC https://www.freepornflix.com/video/849552/wilbur-manly-man-who-secretly-likes-dress-like-a-women-sfw/
Wilbur is a man’s kind of man. he enjoys drinking after a hard day at work. he hangs out with his buddies on the weekends and bbq’s while watching some football or mma fights. he drives a big 4x4 truck and gets all the looks from the ladies. he enjoys the attention he gets from the girls but deep down he admires them as well. what makes wilbur not your ordinary man’s man is that when he is home alone at night, he likes pulling on women’s clothes and make up. it makes him feel really sexy and vulnerable in a way that makes him feel feminine. this is a sfw video as there is no nudity just him changing his clothes and putting on makeup. tags: blake blaze studios, bbs, wilbur, twink, crossdresser, gay, 18-21 yr old, blonde, long hair, homemade, amateur porn, fetish, non nude, sfw, softcore porn, vintage, vintage porn, classic porn ]]> Fri, 10 Apr 2026 10:55:00 UTC https://www.freepornflix.com/video/849552/wilbur-manly-man-who-secretly-likes-dress-like-a-women-sfw/ https://www.freepornflix.com/video/841676/sandra-jayde-09-03-26-j-ai-envie-de-me-faire-biffler-les-fesses/
Une vidéo au format smartphone, 1080x1920 idéale pour visionnage sur smartphone et tablette, pratique pour en faire un wallpaper animé sur le smartphone etc. mon gros cul en collant noir ultra brillant. le bénéfice de la vente de cette vidéo va me permettre de financer une paire de mules à plateforme vertigineuse, transparente, semelle, plateforme et bride en vinyle transparent... la paire ultime pour faire de la vidéo bien pute ! ]]> Mon, 16 Mar 2026 13:28:09 UTC https://www.freepornflix.com/video/841676/sandra-jayde-09-03-26-j-ai-envie-de-me-faire-biffler-les-fesses/ https://www.freepornflix.com/video/838954/sandra-jayde-09-03-26-tgirl-salope-qui-montre-son-gros-cul-en-collant-brillant/
Une vidéo au format smartphone, 1080x1920 idéale pour visionnage sur smartphone et tablette, pratique pour en faire un wallpaper animé sur le smartphone etc. mon gros cul en collant noir ultra brillant. le bénéfice de la vente de cette vidéo va me permettre de financer une paire de mules à plateforme vertigineuse, transparente, semelle, plateforme et bride en vinyle transparent... la paire ultime pour faire de la vidéo bien pute ! ]]> Sun, 15 Mar 2026 13:39:34 UTC https://www.freepornflix.com/video/838954/sandra-jayde-09-03-26-tgirl-salope-qui-montre-son-gros-cul-en-collant-brillant/ https://www.freepornflix.com/video/802456/privat-humiliation-269/
Feminized pink blow whore of the pink punk fetish slut!   this depraved pink punk fetish slut enjoys publicly humiliating her boyfriend as a feminized blow whore. she absolutely loves to make men gay and demasculine them through feminization in combination with fetish. this is the only way this depraved chick can get her orgasms.   (this video is part of the film "kinky pink couple's fetish heaven") ]]> Fri, 27 Feb 2026 11:26:29 UTC https://www.freepornflix.com/video/802456/privat-humiliation-269/ https://www.freepornflix.com/video/799910/dress-up-and-get-fucked/
I’ve got the perfect assignment for a pretty cocksucker like you: get dressed up like the cheap, slutty whore you are and get fucked. squeeze into skimpy clothes, roll those fishnets up your legs, shove your feet into fuck-me heels, and slap on the sluttiest, brightest lipstick so every man knows those lips were made for sucking dick. then crawl out and find a real man with a thick alpha cock. spread those legs and beg him to split your greedy sissy hole wide open. let him pound you raw, breed you deep, turn you into a leaking, trembling mess. get railed until you can’t think straight, then hurry back and confess every filthy second to me. i want to know how perfectly you took it. now move, whore. go get fucked. ]]> Thu, 26 Feb 2026 11:50:26 UTC https://www.freepornflix.com/video/799910/dress-up-and-get-fucked/ https://www.freepornflix.com/video/779793/crossdressing-shoeplay-dangling-and-dipping-with-female-flip-flops/
Today i went out with female flip-flops.i don't care if people look at me and judge me.so i start shoeplaying and dropping and in the end i remain barefoot on the ground.oggi sono uscito di casa con delle infradito da donna.non mi interessa se la gente mi guarda e mi giudica.allora inizio a giocare con le infradito e a lasciarle cadere e alla fine rimango a piedi nudi per terra. ]]> Wed, 18 Feb 2026 10:49:23 UTC https://www.freepornflix.com/video/779793/crossdressing-shoeplay-dangling-and-dipping-with-female-flip-flops/ https://www.freepornflix.com/video/776020/chastity-slut-electrical-torment-720p/
I've dressed my slave in a very slutty outfit and i have him chained up to my fur wall. i'm going to tease and torment this slut relentlessly tonight. i also have him locked up in chastity so i start off fondling and flogging his balls. i tease him about his nip slip, asking him if he had a wardrobe malfunction,  i take out my violet wand and begin shocking his balls, arms, and nipples as i teasingly rub my body up against his. ]]> Tue, 17 Feb 2026 09:48:30 UTC https://www.freepornflix.com/video/776020/chastity-slut-electrical-torment-720p/ https://www.freepornflix.com/video/776019/chastity-slut-electrical-torment-1080p/
I've dressed my slave in a very slutty outfit and i have him chained up to my fur wall. i'm going to tease and torment this slut relentlessly tonight. i also have him locked up in chastity so i start off fondling and flogging his balls. i tease him about his nip slip, asking him if he had a wardrobe malfunction,  i take out my violet wand and begin shocking his balls, arms, and nipples as i teasingly rub my body up against his. ]]> Tue, 17 Feb 2026 09:48:27 UTC https://www.freepornflix.com/video/776019/chastity-slut-electrical-torment-1080p/ https://www.freepornflix.com/video/744348/oops-everyone-knows-you-re-a-sissy-now-wmv/
Your girlfriend is getting ready for date night, but she's having a really hard time deciding what to wear. specifically what lingerie to pair with her dress. so she enlists your help, it's really hard to tell what something is going to look like from the mirror. you putting it on and modeling it for her will give her a much better idea of what goes with the dress... you guys get a little bit carried away, you just look so amazing dressed like that. so good that she wants to commemorate the experience by having a photoshoot! no need to be shy, the pictures are just for the two of you. well they were supposed to be anyways, she accidentally sent all your slutty pictures to her entire contact list. which has your boss and your friends on it... don't be mad, but everyone saw you posing like a slut. i guess date night turned into girls night. ]]> Wed, 04 Feb 2026 10:14:46 UTC https://www.freepornflix.com/video/744348/oops-everyone-knows-you-re-a-sissy-now-wmv/ https://www.freepornflix.com/video/742409/cross-dressing-lingerie-lesson-mp4/
In this custom video, it's your lucky femmed out day! i know you have been desperately wanting to try on some sexy womens lingerie, perhaps it is even your first time doing something this gay... so get out your special ladies lingerie outfit and let me help your sissy ass through this special moment. cum watch as i take you step by step and demonstrate to you how to put on a garter, thong, stockings , front snap bralette and mary jane shoes. i also recommend that you tape your useless cock down to make sure you do not have any unsightly bulges showing in your cute little girly panties. if you pay close attention like a good little fem wanna-be , i will give you all the encouragement you need to get dressed up like a pretty little sissy bitch.       ]]> Mon, 02 Feb 2026 10:47:04 UTC https://www.freepornflix.com/video/742409/cross-dressing-lingerie-lesson-mp4/ https://www.freepornflix.com/video/618356/finally-alone-crossdresser-solo-dildo-copy/
Finally alone, coming home after a day of work and giving yourself a pleasure all alone. i like to feel like a big slut under your eyes, your horny whore who always wants to fuck. watch me enjoy while i play for you.. ]]> Mon, 08 Dec 2025 10:44:50 UTC https://www.freepornflix.com/video/618356/finally-alone-crossdresser-solo-dildo-copy/ https://www.freepornflix.com/video/559147/hex-and-agatha-break-their-new-femboy-toy-lua-1080p-eng-sub-crossdresser-femboy-cross-fucking-cross-blowjob-double-domination-anal-humiliation/
Hex and agatha are a ruthless pair, and tonight their attention is locked on a new femboy crossdresser toy: lua. from the very first command, lua knows his only role is to obey and serve. agatha sets the tone by shoving her strap deep into lua’s throat, face-fucking him until he’s drooling and gagging on her cock. but when hex watches, he realizes this game is better with a real cock involved. agatha orders their little slut to open hex’s pants, slaps lua across the face, and makes him down with a rough hand on the back of his head. now the femboy has no choice but to take both cocks, rubber and real, until his mouth is overflowing with spit and surrender. there’s no break. hex and agatha push lua past every limit, using both his mouth and his ass, trading holes with no mercy. every thrust leaves him weaker, silenced by the relentless pace of their fucking. and when hex finally cums, he fills the condom to the brim, marking lua as the new, dripping possession of this powerful couple. (eng-sub) crossdresser - femboy - cross fucking - cross blowjob - double domination - anal humiliation ]]> Thu, 13 Nov 2025 10:26:49 UTC https://www.freepornflix.com/video/559147/hex-and-agatha-break-their-new-femboy-toy-lua-1080p-eng-sub-crossdresser-femboy-cross-fucking-cross-blowjob-double-domination-anal-humiliation/