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Bareback Sleepover

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

LadyboyObsession episode 10 with Winnie. I didn't used to have many sleepovers when I was young, I never cared much for them. I couldn't understand what it was all about. Perhaps if I had had video games back then I could've stayed up all night and play them with a friend. But that form of entertainment came a bit late for me.It was probably for the best because if I had a friend like Winnie in my room at night she might have pulled me into inappropriate sexual acts a whole lot sooner. Nowadays there is nothing I like more than sleep overs. When I saw Winnie in cute pajamas in one of her photos I felt like a horny teenager again.So I invited Winnie for a sleep over and made a video with her wearing a fresh piece of naughty pajamas and warm socks to give viewers a sense of what I'm talking about..

Format: mp4
Duration: 19:30
Video: 1920x1080, AVC (H.264), 4959kbps
Audio: 155kbps






File size: 731.6 MB


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Cute Blond Vampire Lianna Lawson Pounded Hard

Release Year: 2019
Cast: Lianna Lawson
Genres: Transsexuals, Shemale, Hardcore, Anal, Big Dick, Big Tits, Bubble Butt, Cumshot, Deepthroat, Facial, Male Fucks Trans, Open Mouth Facial, Rimming, Small Tits, Tattoo & Piercing
Video language: English

Wonderful trans vampire Lianna Lawson gets the big cock deep inside her ass in this great sex scene!

Format: mp4
Duration: 42:16
Video: 1920x1080, AVC (H.264), 6224kbps
Audio: 187kbps






File size: 1.9 GB


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Andi - Feminized CD Gives Up The Booty

Release Year: 2018
Studio: BecomingFemme
Genres: Shemale Hardcore, Blowjob, Anal, Bareback

Andi has become a super sexualized super feminized sissy slut. She is ready to go and ready to give up her tight ass to a big dick stud. This petite CD sissy slut loves to please a real man and in this scene she really does!

Format: mp4
Duration: 24:12
Video: 854x480, AVC (H.264), 2932kbps
Audio: 124kbps






File size: 543.1 MB


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Petite fuckdoll

Studio: Ladyboy Gold
Cast: Yo
Genres: Blowjob, Close-ups, Condom, Cumshots, Frottage, Handjob, Hardcore, Natural Tits, POV, Small Cock, Small Tits, Stroking, Wet

Yo is a gorgeous little ladyboy fuckdoll that loves sex. yo gets completely naked and strokes her small girlie stick. yo mischievously sticks out her tongue then gives a mean blowjob. yo is fucked hard and shoots a clear hormone load from her piss slit. now spent. yo holds on for dear life as her asshole is ravaged and jet after jet of scalding hot cum covers her little kathoey frame.

Format: mp4
Duration: 22:23
Video: 1280x720, AVC (H.264), 7810kbps
Audio: 91kbps




File size: 1.3 GB


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Amy - Homemade Pickup Sex

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

Amy's 12th original homemade movie. In this one Amy drives around to find a guy for casual sex. Amy's cock hunt is a success, with a tall hung guy soon in her bed. Amy is eager to try out this new cock and deep throats as much of it as she can. Amy rolls a condom onto the cock and is fucked missionary and doggystyle. For the finale, both strokes their cocks and cum together at the same time. Included is candid conversation with Amy and the guy..

Format: mp4
Duration: 19:30
Video: 1920x1080, AVC (H.264), 7755kbps
Audio: 160kbps






File size: 1.1 GB


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Lorena Mazury

Release Year: 2021
Studio: Trans500
Genres: Shemale, Solo, Cumshot, Masturbation
Video language: English

Lorena Mazury a beautiful and sexy shemale with a beautiful figure who loves sexy games, pleasant viewing and a good mood ...

Format: mp4
Duration: 26:02
Video: 1920x1080, AVC (H.264), 15626kbps
Audio: 185kbps






File size: 2.9 GB


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Tip planted until it stops

Release Year: 2013
Studio: IKillitts Trans500
Cast: Ramon and Tip
Genres: Shemale, Oral Anal Sex, Big Dicks, Asian, Hardcore, Cumshots

Today I introduce to you a lovely Asian ladyboy name Tip. Talk about a sexual energizer TS bunny. Watching her in reverse cowgirl is a must.

Format: mp4
Duration: 19:50
Video: 1280x720, AVC (H.264), 2435kbps
Audio: 184kbps




File size: 381.1 MB


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Transsexual Nurses - part 2 sc.1

Release Year: 2019
Studio: Gender X
Cast: Angelina Please & Michael DelRay

Angelina Please & Michael DelRay - Hot couple! Passionate sex and sucks! trans girl and muscular handsome. Very sexy!

Format: mp4
Duration: 35:51
Video: 1920x1080, AVC (H.264), 5414kbps
Audio: 187kbps







File size: 1.4 GB


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Gets Her Ass Fucked

Release Year: 2021
Cast: Viola Costa & King Epicleus
Genres: Shemale, Hardcore, Bareback, Ass Licking
Video language: English

My lovely brunette companion in bed is dressed in a very beautiful negligee. I am ready to completely kiss her body, it attracted me very much. When I went down into my panties I was slightly taken aback there was an erect cock, but then I decided not to back down.

Format: mp4
Duration: 25:30
Video: 1920x1080, AVC (H.264), 11093kbps
Audio: 124kbps






File size: 2.0 GB


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Holiday Swallower Handjob

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

New has a special Holiday present for you: her sweet cock and slutty ass. New is dressed in a sexy Christmas outfit and is ready for you to unwrap your gift. She's so horny she isn't even wearing any panties. It's a sight! Cock hungry this Christmas New kneels down to service a ready cock top to bottom. Enjoy this special gift for the holidays..

Format: mp4
Duration: 18:20
Video: 1280x720, AVC (H.264), 4870kbps
Audio: 185kbps






File size: 680.0 MB


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Transsexual Nurses - part 2 sc.2

Release Year: 2019
Studio: Gender X
Cast: Nadia Love & Johnny Hill

Nadia Love & Johnny Hill - Hot couple! Passionate sex and sucks! trans girl and muscular handsome. Enjoy!

Format: mp4
Duration: 36:03
Video: 1920x1080, AVC (H.264), 6323kbps
Audio: 187kbps







File size: 1.7 GB


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Aira My First Xxx

Release Year: 2016
Genres: Shemale, Hardcore, Transsexual
Video language: English

Super sexy japanese shemale Aira first time in porn, hardcore anal fucking!

Format: mp4
Duration: 25:34
Video: 1920x1080, AVC (H.264), 7912kbps
Audio: 309kbps






File size: 1.5 GB


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Long Legged Fuckdoll

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

Fuckdoll Dolla from Thailand's capital city Bangkok is a huge fan of Barcelona, with her favorite player being Messi. It's no wonder she preferred wearing the team jersey for this wild fuck fest. In this exclusive LadyboysFuckedBareback episode Dolla gets fucked just the way she loves it. Raw. Oiling up her cock and ass for raw sex with a random stranger is a major turn on for Dolla. Her ass gapes open with ease as his cock slides in. This horny couple fucks in missionary, doggy style and reverse cowgirl until they can't last any longer. Dolla shoots a hot load of jizz all over herself as the POV cock re-insert creampies Dolla's sweet ass.

Format: mp4
Duration: 19:26
Video: 1280x720, AVC (H.264), 4869kbps
Audio: 310kbps






File size: 738.3 MB


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Us Cuties

Release Year: 2019
Genres: Asian, AnalOral Sex, Blowjob, Cumshots, Fingering, Handjob, Masturbation
Video language: Japanese

出張先での甘い誘惑
性欲が抑えきれない若手リーマン二人が酔いどれ暴走交尾!!
酔っ払った勢いで後輩の巨根を咥え込む先輩アナル。もう元には戻れない.。

Format: avi
Duration: 2:03:19
Video: 640x480, DivX 5, 1245kbps
Audio: 187kbps






File size: 1.3 GB


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Ladyboy fucks guy pov

Studio: Ladyboys Fucked Bareback
Cast: Jasmine
Genres: Amateur, Anal, Anal Toys, Bareback, Big Ass, Big Balls, Big Cock, Big Tits, Blowjob, Butt Plug, Close-ups, Cumshots, Deep Throat, Handjob, Hardcore, Ladyboy, No Panties, Oil, POV, Rimming, Stroking, TS Fucks Guy, Upskirt, Wet

Big cock jasmine fucks a guy pov! admire the incredible rod of this hung ladyboy as she takes control. jasmine gets a handjob and turns over for insertion of a black buttplug. her cock is throbbing and she prepares the guys ass for fucking.
jasmine is already dripping precum as she pushes inside. her big udders titty fuck the guy while her cock is inside his ass. to jasmine's satisfaction the pressure of her big prick again his prostrate makes him cum uncontrollably. cum everywhere. the buttplug is removed from jasmine's deep ass. she cranks her big girlie stick and cums on her belly and belly button.

Format: mp4
Duration: 22:28
Video: 1280x720, AVC (H.264), 7808kbps
Audio: 91kbps




File size: 1.3 GB


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Dizzy Trans Revolution With Perfect Melainy Vilhena

Release Year: 2015
Cast: Melainy Vilhena
Genres: Shemale, Transsexual, Anal, DP, Oral, Gonzo, Hardcore, Teen, Fetish
Video language: English

Brazilian chick with dick Melainy Vilhena is sure to give you the biggest hard-on you will ever have! Once you sample this Brazilian tranny you will never look back!!

Format: mp4
Duration: 25:13
Video: 1920x1080, AVC (H.264), 8257kbps
Audio: 124kbps






File size: 1.5 GB


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Hearts Bareback

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

Ladyboy Pie from Bangkok is featured in today's all exclusive LadyboyHandjob episode called Hearts Bareback HJ. In today's episode Pie is wearing sexy pink pajamas with a heart print and matching stockings. Her nails are painted in bright pink. She looks stunning in this outfit. You could probably watch and enjoy this look all day long. But just as you thought you reached the top of the mountain it only gets better. Pie's top comes off exposing her big tits. As Pie loves the taste of dick in her mouth, she wastes no time. Enjoy Pie from close-up angels as the camera displays every inch of her handjob and blowjob perfection. Enjoy guys!.

Format: mp4
Duration: 19:42
Video: 1280x720, AVC (H.264), 4870kbps
Audio: 185kbps






File size: 730.4 MB


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Trans On Trans Fucking With Nadia Love & Jenna Creed

Release Year: 2019
Cast: Nadia Love, Jenna Creed
Genres: Transsexuals, Shemale, Anal, Big Tits, Blonde, Blowjob, Brunette, Bubble Butt, Cumshot, Deepthroat, Facial, Hardcore
Video language: English

Nadia Love and Jenna Creed are some of the hottest trannies in the world and they enjoy kissing, licking and hardcore sex!

Format: mp4
Duration: 24:36
Video: 1920x1080, AVC (H.264), 6926kbps
Audio: 187kbps






File size: 1.3 GB


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Horny after school bareback

Studio: Ladyboy Gold
Cast: Pan
Genres: Bareback, Big Cock, Blowjob, Close-ups, Cosplay, Cumshots, Facials, Frottage, Gaping, Handjob, Hardcore, High Heels, Mini Skirt, Natural Tits, Pantie Aside, Panties, POV, Schoolgirl, Small Tits, Stockings, Stroking, Teen, Upskirt

Girl pan barebacked with her panties at her knees! up comes pan's yellow tartan skirt and her uncut prize dangling right in your face. pan gives a pov blowjob then has her tiny asshole filled with hot hard cock. lots of open gapes of pan's well-used ladyboy ass-pussy. pan's asshole is gaped big as the cock pulls out and sprays from her belly to face. pan gets a surprise cumblast to the face in the process.

Format: mp4
Duration: 22:37
Video: 1280x720, AVC (H.264), 7808kbps
Audio: 91kbps




File size: 1.3 GB


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Dahlia Crimson Gets Bareback Yoga From Trans Teacher

Release Year: 2021
Studio: TransRoommates
Cast: Dahlia Crimson, Pixi Lust
Genres: Shemale on Shemale, Anal, Bareback
Video language: English

Dahlia Crimson wants to keep her amazing trans body in shape by becoming an expert on yoga. Her instructor Pixi Lust wants to help her figure out all the stretches but she also has some unorthodox methods. Before Dahlia knows it, she's got Pixi's hard girl cock bare in her ready to fill her up with creampie as part of her yoga training.

Format: mp4
Duration: 26:40
Video: 1920x1080, AVC (H.264), 3905kbps
Audio: 191kbps






File size: 801.2 MB


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Skinny Friends Mutual Debut

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

I was super excited this night, I had finally found Pimmie through some of my ladyboy models, she told me she had done porn videos before but she only played with herself in it but now wanted to make a hardcore video just like her friends had done before her. When I asked her to come over she told me she was a little scared because we hadn't known each other all that well yet and if i was ok if her friend came along. Little did I know her friend was an insanely cute ladyboy with a lovely petite teen body. So when she showed up I had to ask if she wanted to join in, by the time I had finished my question she was already touching my inner thigh, she looked up with the naughtiest grin I had ever seen and whispered yes. It was a good thing I had packed two collars by accident it seems, watch Pimmie and Ploy's hardcore debuts right here..

Format: mp4
Duration: 19:50
Video: 1280x720, AVC (H.264), 4869kbps
Audio: 185kbps






File size: 734.9 MB


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Raw Trans Fucking With Casey Kisses & Alexa Scout

Release Year: 2019
Cast: Casey Kisses, Alexa Scout
Genres: Transsexuals, Shemale, Anal, Big Tits, Blonde, Blowjob, Brunette, Bubble Butt, Cumshot, Deepthroat, Facial, Hardcore, Open Mouth Facial, Red Head, Rimming, Small Tits, Tattoo & Piercing, Trans Fucks Trans
Video language: English

We present amazing sex action with beauty shemales Casey Kisses and Alexa Scout! They enjoy very intense and hardcore fuck!

Format: mp4
Duration: 35:22
Video: 1920x1080, AVC (H.264), 5845kbps
Audio: 187kbps






File size: 1.5 GB


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He My Girl pt.2

Video language: English

Of course they then return the favor by filling his ass full of hot cock as well!

Format: Windows Media
Duration: 22:33
Video: 720x480, Windows Media Video V8, 2304kbps
Audio: 125kbps






File size: 403.7 MB


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Adele Blowjob and Frottage

Video language: English

Adele sucks on a meaty cock, then rubs her dick against a guys in frottage action to cum. The taste of cock in Adele's mouth makes her especially horny. The throbbing of cock turns her on and Adele takes off her pantyhose and rubs cock against the guys. Adele lubes up both cocks and strokes them together until she explodes her gooey girl-spunk. Adele pulls up the guys shirt and sperms on the white guys' belly.

Format: mp4
Duration: 24:02
Video: 1920x1080, AVC (H.264), 7773kbps
Audio: 123kbps






File size: 1.4 GB


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Ass Lick and Puckered Hole Bareback

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

Quiz has a long rimming session with the POV's snaking her tongue deeply up the guys asshole while she jerks off. Quiz is a kinky babe and loves licking assholes of men. The smell of an asshole face-sitting Quiz makes her cock throb and sticky sperm erupt from her large girl-stick. After Quiz cums she shows off her gaping asshole. The POV's dick slides inside Quiz's open anus. Quiz is always ready for dick and she gives an ass to mouth BJ between the change of missionary to reverse cowgirl. Quiz impales herself cowgirl then get a graphic butt fucking while bent over on the couch. Quiz gapes rudely as the cock pumps sperm onto her crack and pretty pink babydoll lingerie..

Format: mp4
Duration: 19:49
Video: 1280x720, AVC (H.264), 4868kbps
Audio: 310kbps






File size: 752.6 MB


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Trans-Sylvania - Janelle Fennec

Release Year: 2019
Cast: Janelle Fennec
Genres: Transsexuals, Shemale, Hardcore, Anal, Big Dick, Big Tits, Bubble Butt, Cumshot, Deepthroat, Facial, Male Fucks Trans
Video language: English

Gorgeous Trans-Sylvanian lady Janelle Fennec gets some hardcore anal action with hot man! His thick dick probes tight, tender orifice in this raunchy anal exploration!

Format: mp4
Duration: 29:49
Video: 1920x1080, AVC (H.264), 6599kbps
Audio: 187kbps






File size: 1.4 GB


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He My Girl pt.1

Video language: English

These are some of the hottest girls in town. They just happen to be packing a dick beneath their skirt. Watch these hot shemales take a hard ass pounding from their loving boyfriends.

Format: Windows Media
Duration: 21:42
Video: 720x480, Windows Media Video V8, 2304kbps
Audio: 125kbps






File size: 386.3 MB


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Emma Rose & Dominic Pacifico The Spy Who Rode Big Missiles

Release Year: 2021
Studio: TransAngels
Cast: Emma Rose & Dominic Pacifico
Genres: Athletic, Caucasian, Blonde, Agent, Boots, Male to Shemale, Small Tits, Anal, Trans
Video language: English

Stunning Emma Rose is a spy infiltrating the Rebel Army HQ in order neutralize the big bad guys. After sneaking into the barracks, knocking out a security guard and stealing his outfit, the fierce Emma tries to find the computer and abort a missile launch. However, Dominic Pacifico, the hot but evil general, walks into the barracks before Emma has time to put on her stolen army pants. Horny Dominic thinks Emma is a newly hired soldier. Seduced by the spy's skillful hip swinging, the general can't help but start banging her attractive butt. Will Emma's sexy diversion save the world from nuclear Armageddon?

Format: mp4
Duration: 26:05
Video: 1920x1080, AVC (H.264), 3579kbps
Audio: 115kbps






File size: 706.6 MB


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Milked Sex

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

LadyboyObsession episode 14 with Chotika. I spotted Chotika outside in front of the mall, she was wearing a naughty outfit, wearing sunglasses and licking away on a Cornetto ice cream. I approached her but she flat out ignored me, she said something I didn't understand in order to not make a tit out of myself I just left the embarrassing scene.Imagine the surprise when one of the ladyboy models told me she had a friend who wanted to make porn videos who turned out to be the exact same girl! So two days later I had Chotika in my room, I think she did't remember the situation. After I had her locked to the bed I refreshed her memory. She just gave me a dirty smirk and told me to stop crying and start fucking her itching back pussy. So I did, watch her porn debut right here on LadyboyObsession..

Format: mp4
Duration: 18:35
Video: 1280x720, AVC (H.264), 5845kbps
Audio: 124kbps






File size: 813.3 MB


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Transsexual Nurses - part 2 sc.3

Release Year: 2019
Studio: Gender X
Cast: Jenna Gargles & Wolf Hudson

Jenna Gargles & Wolf Hudson - Hot couple! Passionate sex and sucks! trans girl and muscular handsome. Enjoy!

Format: mp4
Duration: 30:09
Video: 1920x1080, AVC (H.264), 6832kbps
Audio: 187kbps







File size: 1.5 GB


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Transsexual Mashup - Lisey Sweet, Aspen Brooks

Release Year: 2018
Cast: Lisey Sweet, Aspen Brooks
Genres: Shemale On Female, Hardcore, Bareback, Anal, Pusssy & Ass Licking
Video language: English

These splendid babes Lisey Sweet and Aspen Brooks enjoy intense buttfuck! They are totally exhausted and happy.

Format: mp4
Duration: 21:09
Video: 1920x1080, AVC (H.264), 6950kbps
Audio: 187kbps






File size: 1.1 GB


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Petite Trans Schoolgirl Allie Valentine Meets Big Cock

Release Year: 2021
Cast: Allie Valentine
Genres: Shemale Hardcore, Blowjob, Anal, Bareback
Video language: English

Allie Valentine is a nerdy and shy trans schoolgirl who is getting some private tutoring for her midterm exam.

Format: mp4
Duration: 26:03
Video: 1920x1080, AVC (H.264), 7826kbps
Audio: 229kbps






File size: 1.5 GB


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Offy - Facesitting Rimjob & 2 Big Pops

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

Offy is a big dick Femboy who loves licking the assholes of Farangs to make herself cum. Offy is naked, and has her flat chest covered in oil and her fat cock srping to attention. Thick strands of pre-cum string from Offy's piss slit. Offy sucks on a hard cock while stroking her meat. Offy devours the dick like it's her meal for the day, tasting every inch of the cock's shaft and balls.Offy is a submissive femboy slut, and sticks her tongue out while the guy lowers his asshole onto her face. Offy dips her tongue into the meat of the guys anus and pounds her throbbing cumstick. The POV cock explodes all over Offy's tiny tits and Offy launches a cumshot all over herself. Offy is spent and covered in hot spunk. The ending is Offy in the shower washing her lithe Femboy body..

Format: mp4
Duration: 19:41
Video: 1920x1080, AVC (H.264), 7786kbps
Audio: 309kbps






File size: 1.1 GB


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Staying Alone With A Blonde Tranny Babe

Release Year: 2019
Cast: Yulia Masakowa, Dante Colle
Genres: Transsexual, Shemale On Male, Anal, Bareback, Ass Licking, Russian, Cum On Mouth
Video language: English

Tall, gorgeous Yulia Masakowa and Dante Colle are amicable exes that still live together. The arrangement works well for them, but Dante's new girlfriend can't help but get jealous of the toned and tight t-girl. When she catches a peek of Yulia's cock, the new girl is so upset that she'll never be able to satisfy Dante properly, that she runs out to the store to get a special surprise. While she's gone Yulia and Dante fall into old habits, indulging in a steamy mid-afternoon fuck fest. Yulia pounds Dante's hole all over the living room, making him moan in all the ways his new girlfriend never could.

Format: mp4
Duration: 33:00
Video: 1920x1080, AVC (H.264), 5847kbps
Audio: 124kbps






File size: 1.4 GB


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With Adorable Transsexual Ladies

Release Year: 2021
Genres: Shemale ,Transexual ,Ladyboys ,TransBoy
Video language: English

Dominant Trans Cherry Mavrick makes her submissive lover Jamie French obey her every command. She fucked her so hard and deep!.

Format: mp4
Duration: 22:37
Video: 1920x1080, AVC (H.264), 7840kbps
Audio: 280kbps






File size: 1.3 GB


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Blonde Bombshell Summer Rayne

Release Year: 2021
Genres: Male On Shemale, Hardcore, Blowjob, Assliking, Rimming, Bareback
Video language: English

Who doesn't like Summer, right?? I mean, Summer Rayne that is. And no, not rain, I'm talking about this hot blonde bombshell Summer Rayne! This horny slut loves getting nut blasted all over her and you can see it in her eyes! Just watch the way she handles Kai's cock in this one. She can suck, fuck, you name it, she can do it like a pro. You're definitely not going to want to miss this one. Enjoy!

Format: mp4
Duration: 24:59
Video: 1920x1080, AVC (H.264), 7836kbps
Audio: 291kbps






File size: 1.5 GB


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