Gabriel D'Alessandro Movies

  • 2013
    TS Playground 4

    TS Playground 4

    TS Playground 4

    02013HD

    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 o...

    TS Playground 4
  • 2014
    TS Playground 8

    TS Playground 8

    TS Playground 8

    02014HD

    With the obsessive, hard-core eroticism and unique camerawork that make his straight movies hits with anal fanatics, director Jay Sin presents "TS Pla...

    TS Playground 8
  • 2012
    TS Playground 2

    TS Playground 2

    TS Playground 2

    102012HD

    With his sphincter-stretching hetero porn, director Jay Sin is an infamous pioneer of nasty-yet-playful anal extremes. The king of the colon explores...

    TS Playground 2
  • 2014
    TS Playground 7: Ebony Edition

    TS Playground 7: Ebony Edition

    TS Playground 7: Ebony Edition

    02014HD

    Jay Sin, porn's anal adventurer, likes taking his direction in different directions, and one perverse pleasure he explores is transgender attraction....

    TS Playground 7: Ebony Edition
  • 2017
    Fetish Findr

    Fetish Findr

    Fetish Findr

    02017HD

    In ‘Fetish Findr’, two doms and three subs are on an online mission to find their ultimate fetish turn on. Find out what makes masters and slaves tick...

    Fetish Findr
  • 2017
    Cum Dump Pumping

    Cum Dump Pumping

    Cum Dump Pumping

    02017HD

    Piggy CUM DUMPs and their ass PUMPING tops, fuck their brains out in five filthy scenes! Don't miss these major rounds of hardcore sucking, rimming, a...

    Cum Dump Pumping
  • 2009
    Cuckolded on My Wedding Day 1

    Cuckolded on My Wedding Day 1

    Cuckolded on My Wedding Day 1

    02009HD

    It was supposed to be a wonderful day and a beginning of a new life with my blushing bride. But no sooner did we get done with the ceremony and my wif...

    Cuckolded on My Wedding Day 1
  • 2012
    Jessica Drake's Guide To Wicked Sex: Anal Play for Men

    Jessica Drake's Guide To Wicked Sex: Anal Play for Men

    Jessica Drake's Guide To Wicked Sex: Anal Play for Men

    02012HD

    Every man wants to know...but few are brave enough to ask. If you are curious about anal play for men, but don't know where to start, this movie is fo...

    Jessica Drake's Guide To Wicked Sex: Anal Play for Men
  • 2018
    Watching My Husband Bang a TS

    Watching My Husband Bang a TS

    Watching My Husband Bang a TS

    02018HD

    Gender X is back with another hot movie. I love watching my husband bang! But once you get a T.S. involved, that's when it gets really spicy! These ba...

    Watching My Husband Bang a TS
  • 2011
    Strap Attack 15

    Strap Attack 15

    Strap Attack 15

    02011HD

    Director Joey Silvera reignites the perverse passions behind his popular girl-on-man pegging series: “Strap Attack 15” is chock-full of gorgeous, youn...

    Strap Attack 15
  • 2018
    My TS Stepmom

    My TS Stepmom

    My TS Stepmom

    02018HD

    After the sudden death of his estranged father, Gabriel returns home for the funeral and to talk to his father's attorney about his last will and test...

    My TS Stepmom
  • 2024
    Fluid: Men Redefining Sexuality

    Fluid: Men Redefining Sexuality

    Fluid: Men Redefining Sexuality

    02024HD

    Part documentary, part pornography, this film from award-winning director Madison Young is more than the sum of its parts. These men are deconstructin...

    Fluid: Men Redefining Sexuality
  • 2022
    Trans-Starz! 7

    Trans-Starz! 7

    Trans-Starz! 7

    102022HD

    From the archives of filmmaker Joey Silvera comes "Trans-Starz! 7," a bulging compilation of versatile TS debauchery. In two scenes, pretty T-girls se...

    Trans-Starz! 7
  • 2011
    DILF Adventures 4

    DILF Adventures 4

    DILF Adventures 4

    02011HD

    On an orange couch against a yellow wall, Matheus Axell (bald, tanned, tattooed, glasses) sucks Mauricio (tall, slim, pale); Matheus tops Mauricio; Ma...

    DILF Adventures 4
  • 2019
    My TGirl Stepsister

    My TGirl Stepsister

    My TGirl Stepsister

    02019HD

    My new step sister is so cute and so hot... I wonder if she has a nice cock? Well, guess what? My step-sister is trans and she wants to fuck with her...

    My TGirl Stepsister
  • 2018
    Angels in Public

    Angels in Public

    Angels in Public

    02018HD

    Aubrey Kate is out jogging and decides to help a man with engine problems. After a shaky start Aubrey and her unfortunate motorist climb into the fron...

    Angels in Public
  • 2018
    My TS Stepsister

    My TS Stepsister

    My TS Stepsister

    02018HD

    Watch as gorgeous TS stepsisters Casey Kisses & Chanel Santini seduce their stepbrothers quickly falling into a forbidden love affair. Nothing is more...

    My TS Stepsister
  • 2017
    I Love a Trans in Uniform

    I Love a Trans in Uniform

    I Love a Trans in Uniform

    02017HD

    Admirals and officers and firefighters, oh my. Nothing is hotter than these gorgeous transgender women as they take control of some sticky situations....

    I Love a Trans in Uniform
  • 2010
    Ass Fucked by a DILF 2

    Ass Fucked by a DILF 2

    Ass Fucked by a DILF 2

    02010HD

    There's nothing like the experience of being Ass Fucked by A DILF in bed to really get you off! They know exactly how you like your cock stroked and t...

    Ass Fucked by a DILF 2
  • 2018
    Trans Prison

    Trans Prison

    Trans Prison

    02018HD

    Shocking true prison stories! Inmate Aubrey Kate was scared and shy, but before long this little t-girl gets snapped up quick by a hard con who offer...

    Trans Prison