TS Playground Collection

Part 4 · Sep 25, 2013

TS Playground 4

Anal explorer Jay Sin continues his journey into an exotic, hidden sexual world in his new lady-boy adventure, TS Playground 4. Jays signature style of sexy costume play and fantastic butthole antics perfectly suit the kinky, feminine transsexuals he's selected for this outrageous she-male showcase. The movie is a sultry mix of tease and solo self-pleasure alongside scenes of intense, hard-core dicksucking and ass fucking that match transgender temptresses and their cock-struck boyfriends. And as the tagline says, "These girls are hung!"

Part 5 · Oct 7, 2013

TS Playground 5

Creatively twisted, butthole-obsessed pornographer Jay Sin has a keen eye and a perverse passion for gorgeously feminine she-males. His new, double-disc "TS Playground 5" showcases the director's unique mix of high glamour, kinky fun and hard-core anal debauchery. In six scenes of tranny seduction and lust, Jay's luscious lady-boys just can't get enough ass play!

Part 6 · Nov 25, 2013

TS Playground 6

Kinky porn pioneer Jay Sin has won ass-obsessed hearts through an amazing career of documenting extreme rectal perversity with the most anally acrobatic ladies in the game. His explosive she-male series has proved just as creative and intense, maintaining the high standards of asshole fetishism Jay is known for. His TS Playground 6 is front-loaded with stunning she-creatures performing nasty deeds with boys, girls and, occasionally, one another.

Part 7 · Jan 27, 2014

TS Playground 7: Ebony Edition

Jay Sin, porn's anal adventurer, likes taking his direction in different directions, and one perverse pleasure he explores is transgender attraction. His TS Playground 7, subtitled, "Ebony Edition," stars a bevy of black T-girl temptresses and dark-skinned Latinas - all exuding the smoldering eroticism to seduce aficionados of exotic she-male allure. TS Playground 7 contains three solo masturbation scenes and three hard-core fuckfests with trans-loving boy-toys.

Part 8 · Feb 24, 2014

TS Playground 8

With the obsessive, hard-core eroticism and unique camerawork that make his straight movies hits with anal fanatics, director Jay Sin presents "TS Playground 8," featuring sultry, ultra-feminine she-males from the other side of the tracks. Among six scenes, there's a variety of intimate solo transgender action as well as hard-core fun with both boys and girls — but Jay's gorgeous T-girls all share a common trait: They sport exceptionally large packages!

Part 9 · Mar 19, 2014

TS Playground 9: TS Gape Lovers

In TS Playground 9, transsexual aficionado Jay Sin presents she-male shenanigans in five lusty varieties.

Part 10 · Apr 23, 2014

TS Playground 10

Imaginatively nasty Jay Sin presents six diverse scenes of she-male lust in “TS Playground 10.”

Part 11 · May 19, 2014

TS Playground 11

Dirty-minded director Jay Sin’s “TS Playground 11” delivers exotic she-male shenanigans in various scenarios and combinations.

Part 12 · Jul 23, 2014

TS Playground 12

"TS Playground 12" continues creative pornographer Jay Sin's wildly successful series with sexy, offbeat trans-girl scenario.

Part 13 · Nov 10, 2014

TS Playground 13

Feminine, functional, well-hung she-males get off with hard, horny men (and in one case, a hot genetic girl) in director Jay Sin's TS Playground 13.

Part 14 · Dec 17, 2014

TS Playground 14

When director Jay Sin merges his infamous style of anal porn with the naked eroticism of beautiful, gender-bending she-creatures, the results are explosively nasty! TS Playground 14 features an insatiable cast of luscious, well-hung, ultra-feminine ladyboys indulging in intimate sessions of unrestrained cock worship and ass fucking ... with other she-males, as well as a couple of lucky boys and girls!

Part 15 · Jan 19, 2015

TS Playground 15

Ass-obsessed director Jay Sin is a legend among devotees of extreme anal antics. He brings that nasty yet fun sensibility to his she-male porn as well. Jay's latest, “TS Playground 15: Ladyboy Edition,” is one hardcore walk on the wild side, with a bevy of delectable Asian and Latina ladyboys enjoying intense, one-on-one assfucking pleasure!

Part 16 · Feb 25, 2015

TS Playground 16

The wild, no-limits approach to video that helped veteran director Jay Sin mastermind a revolution in anal porn has made him a beloved player in the transsexual arena. “TS Playground 16” showcases a stunning array of well-hung, ultra-feminine she-male beauties posing playfully and indulging in gender-bending hard-core pleasures with guys, girls ... and each other!

Part 17 · Apr 6, 2015

TS Playground 17

Gorgeous, ultra-feminine, super-functional she-males have a field day in director Jay Sin’s “TS Playground 17.”

Part 18 · May 18, 2015

TS Playground 18

In “TS Playground 18,” director Jay Sin showcases a multi-ethnic cast of beautiful ladyboys doing whatever cums naturally with their horny boyfriends. Four scenes of sensuous, explicit she-male-on-dude action plus one solo masturbation session give Jay’s ultra-feminine trans creatures plenty of throbbing meat to play with!

Part 19 · Jun 22, 2015

TS Playground 19: Ladyboy Edition

Perversion pioneer Jay Sin takes the single-minded obsession of his spectacular anal porn and applies it to the sensuous world of she-males. In TS Playground 19, Jay presents a bevy of stunning, new transsexual sweethearts from exotic Thailand that love taking on studly male partners, adventurous females ... or each other!

Part 20 · Jul 20, 2015

TS Playground 20

Director Jay Sin’s signature style — extreme anal perversions presented with an inviting sense of playful delight — is the perfect view into the sensuous world of hot T-girls. “TS Playground 20” delivers hard-core fun with these gorgeous, ultra-feminine she-males and their big, juicy, fully functional cocks!

Part 21 · Sep 28, 2015

TS Playground 21

Globetrotting thrill seeker Jay Sin’s recent adventures have uncovered gorgeous she-males that combine petite femininity with hard-charging erections to give “TS Playground 21” forbidden thrills.

Part 22 · Oct 19, 2015

TS Playground 22: Ladyboy Edition

Anally obsessed director Jay Sin and his adventurous cast explore the sensual pleasures of ultra-feminine, fully functional Thai T-girls in 'TS Playground 22,' the second 'Ladyboy Edition' to date for this playful and perverse series.

Part 23 · Jul 26, 2016

TS Playground 23

From the master of extreme anal erotica, director Jay Sin, comes a showcase of sultry, feminine starlets sporting huge, throbbing she-cocks! The luscious ladyboys of "TS Playground 23" get off on intimate, one-on-one sex with horny gentlemen, and there's even a nasty backdoor scene with a genetic female, bodacious French bombshell Eloa Lombard! On his first night in Brazil, stud Trent Dy and statuesque trans-girl Deborah Mastronelly share blow jobs and anal perversions, climaxing in messy cum explosions. Slender, girlish Kalliny Nomura offers oral pleasure and mutual ass fucking to her new boyfriend. Stylish blonde Bianca Hills uses her stiff, uncut she-prick to ream her man's tight bunghole...

Part 24 · Oct 29, 2016

TS Playground 24

In 'TS Playground 24,' distinctive director Jay Sin spotlights feminine, fully functional trans beauties in solo sessions and gender-bent trysts with adventurous, hung studs.

Part 25 · Jan 23, 2017

TS Playground 25

Director Jay Sin, the master of playfully nasty anal pornography, turns his camera toward the exotic world of glamorous T-girls and the kinky dudes that love them: TS Playground 25 presents a comely international cast in seductive solo scenes and dates with bold male studs in search of mutual blowjobbery and passionate, raw ass fucking.

Part 26 · Mar 10, 2017

TS Playground 26

In “TS Playground 26,” outrageous director Jay Sin combines gender-bending transsexual erotica with extreme anal perversion: Four femme, functional T-girls take on adventurous studs for butt fucking, and two more display their playful solo masturbation techniques.

Part 27 · May 1, 2017

TS Playground 27

Director Jay Sin spotlights the sexiest trans talent from Brazil and the U.S. in "TS Playground 27." Femme but very functional beauties tease the camera with their big knockers and fat, swinging she-cocks, and they enjoy lewd blow jobs and anal hookups with wild guys and girls.

Part 28 · Apr 3, 2019

TS Playground 28

Director Jay Sin indulges his infinite appetite for edgy, boundary-busting sex with the intriguing beauties of "TS Playground 28." These feminine T-girls live for pleasure, including solo masturbation, dirty dates with adventurous men, kinky threesomes and rendezvous with other sexy trans goddesses!

Part 29 · May 1, 2019

TS Playground 29

Tempting trans performers show off their kinky sexuality, pretty bodies and big, up-front bonuses in daring director Jay Sin's "TS Playground 29." Four scenes feature super-sexy T-girl hotties indulging in salacious anal fucking, tasty ass-to-mouth blowjobs and creamy ejaculations; plus see a tantalizing solo masturbation exhibition.

Part 30 · Jul 1, 2019

TS Playground 30

Distinctive director Jay Sin's trademark has always been a cross between perverse fetish and lighthearted play. True to form, "TS Playground 30" infuses nasty anal action with a palpable sense of fun as pretty-but-hung trans models enjoy erotic recreation, from solo masturbation to sex with male studs to T-girl-on-T-girl dates.

Part 31 · Aug 1, 2019

TS Playground 31: Ladyboy Edition

Muscle stud Spencer Fox introduces slim, short haired TS Jenny. The cute, young Thai ladyboy strokes her she-dick as she gives Spencer a slobbery blowjob. She whimpers while riding his stiff prick. Spencer spanks Jenny as he reams her from behind, and the trans temptress masturbates to an explosive orgasm while Spencer slam-fucks her rectum. Intense anal reaming makes her butthole gape. Jenny sucks cock ass-to-mouth and takes messy cum facial.

Part 32 · Sep 12, 2019

TS Playground 32

Director Jay Sin is a world-famous porn expressionist whose skill with anal spectacle brings out the best in feminine, well-hung T-girls. In "TS Playground 32," his cast of dick-swinging cuties shares hardcore fun with horny guys as well as other trans bombshells, and don't miss an especially freaky solo exhibition.

Part 33 · Oct 16, 2019

TS Playground 33: Ladyboy Edition

Veteran pornographer Jay Sin spotlights a stellar array of feminine, well-endowed Asian trans babes in "TS Playground 33 Ladyboy Edition." Six perverse scenes include a variety of action: Flashy T-girls share gender-bending backdoor fun with bold studs; a transsexual shows off her huge cock in a solo jack-off performance; and a crazy threesome includes TS-on-TS fun!

Part 34 · Nov 7, 2019

TS Playground 34

Aspen, Kyaa and Spencer have a kinky threesome with all kinds of twisted, nasty positions. Cum-hungry Milli loves to have Spencer's big cock up her gaping butt. Super model TS Arianna Lexa is a bombshell babe with loads of cum for you. Introducing gorgeous Russian TS Lilu Mae to the playground. European TS dolls Sasha and Bailey love to fuck each other.

Part 35 · Dec 4, 2019

TS Playground 35: Ladyboy Edition

Outrageous porn pioneer Jay Sin spotlights tempting transsexual sweethearts from the exotic lands of southeast Asia in "TS Playground 35 Ladyboy Edition." The movie features five gender-bending babes in hardcore anal dates with bold, hung studs. Dominant T-girl Jasmine subjects Gabriel to serious backdoor pounding. He masturbates as Jasmine reams his rectum, and he gives a messy, ass-to-mouth blowjob. Asian trans babe Anna playfully flaunts her thick prick through a sassy tease. When muscle dude Spencer Fox fucks Anna's butt, her cock gushes cum over her fit tummy! Kai Bailey lubes up TS Laura Sky's sphincter for passionate sodomy. She whimpers through a buttfuck till Kai blows hot wads of sperm onto Anna's girl boner. Adorable Bangkok transsexual Mikki looks sweet in her tiny skirt. Gabe submits to her rowdy rump reaming, and Mikki rewards him with a cum facial. Leggy T-doll Paula Long rims Spencer, gives raunchy fellatio, and then bends him over and bangs his bunghole!

Part 36 · Jan 13, 2020

TS Playground 36

Director Jay Sin, the purveyor of fun-loving filth, spotlights alluring she-starlets and decadent delights in "TS Playground 36." Jay's keen, creative eye captures playful perversion — tempting T-girls indulge in torrid sodomy with hung dudes in three scenes, and two more adventures are graphic, trans-on-trans escapades.

Part 37 · Feb 10, 2020

TS Playground 37: Ladyboy Edition

Exotic Asian trans chicks seek adventure in outrageous director Jay Sin's "TS Playground 37 Ladyboy Edition. " The cute gender benders enjoy orgasmic masturbation, deep anal reaming and asshole gaping.