Jessie Montgomery

Jessie Montgomery

  • Title: Jessie Montgomery
  • Popularity: 1.889
  • Known For: Acting
  • Birthday:
  • Place of Birth:
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  • Also Known As:
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Jessie Montgomery Movies

  • 2021
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    Haunted Holes

    Haunted Holes

    10 2021 HD

    BIG things go bump, AND grind in the night, in these spooky good tales of terrified twink’s getting their tight tails taught lusty lessons. Get...

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  • 2013
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    Twink House Party

    Twink House Party

    1 2013 HD

    When the cat’s away the twinks will play. This is a party you don’t want to miss! Hot boys get together at Evan Parker’s house for...

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  • 2013
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    Helix Academy

    Helix Academy

    9.5 2013 HD

    The finest boys in America travel across the country to enroll at Helix Academy for it’s rich fraternal traditions, wholesome student body and...

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  • 2013
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    Out in the Open

    Out in the Open

    7 2013 HD

    Sometimes fucking is more fun out IN THE OPEN! Let your inner voyeur out to play because these young boys enjoy an audience. Evan Parker pulls over...

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  • 2013
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    Bareback Night & Day

    Bareback Night & Day

    1 2013 HD

    These boys love bareback any time of day! There’s definitely no room for a condom when Kyle Ross takes two twink cocks up his tender bareback...

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  • 2013
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    Morning Wood 2

    Morning Wood 2

    1 2013 HD

    Start your day off hot and horny with the thick dick twinks of MORNING WOOD 2. Andy Taylor’s cock has a mind of its own and when his throbbing...

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  • 2013
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    Twink Wet Dream

    Twink Wet Dream

    1 2013 HD

    Drift off into a sex charged dreamland where Fantasy Boys Evan Parker, Anderson Lovell, Casey Tanner and Jessie Montgomery act out your deepest...

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  • 2013
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    Out in the Open 2

    Out in the Open 2

    1 2013 HD

    There’s nothing like a good fuck outdoors! It’s a hot summer and these twinks love to let it all hang out...in public. After a dip in the...

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  • 2013
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    California Boys

    California Boys

    1 2013 HD

    The summer sunshine is here and that means it’s open season on fucking California’s hottest tanned twinks! There’s plenty of...

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  • 2013
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    Luke & Jessie's Twinkmas

    Luke & Jessie's Twinkmas

    1 2013 HD

    Boys love their toys and at this Twinkmas Party everyone gets to give and receive! Christian begins the festivities by loosening up Jessie’s...

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  • 2014
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    Scandal at Helix Academy

    Scandal at Helix Academy

    8.583 2014 HD

    The third installment of the Award-Winning twink schoolboy series adds another layer of drama and intrigue to the story of the All-American Boys...

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  • 2014
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    Twink Fap Solos

    Twink Fap Solos

    6 2014 HD

    Even after fucking all the beautiful boys at Helix Studios these horny twinks still need a good fap. Casey Tanner, Christian Collins and Jordan...

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  • 2014
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    Bareback Twink Tales

    Bareback Twink Tales

    1 2014 HD

    Twinks have a way of finding themselves in sexy serendipitous situations. Evan Parker’s lazy day turns into a booty call to his bottom boy...

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  • 2013
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    Working Stiff

    Working Stiff

    1 2013 HD

    All work and no play? That’s not the Helix Way! When sweaty working men need to relax their stiff dicks they employ the tightest twink assholes...

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  • 2014
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    Bareback Boys

    Bareback Boys

    1 2014 HD

    There’s plenty of new bareback boys to break in as Shane Hicks, Damon Archer, Adrian Rivers and Seth Andrews all make their Helix debuts. Join...

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  • 2014
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    Matthew Keading: Bareback

    Matthew Keading: Bareback

    1 2014 HD

    Dream boy Matthew Keading is a fan favorite for his insatiable sex drive and passionate performances in six of Helix’s Top Rated scenes ever!...

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  • 2014
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    Helix Academy 2

    Helix Academy 2

    10 2014 HD

    The drama at the All-American Boys Academy continues with star-crossed lovers Scotty Clarke and Jessie Montgomery navigating study hall threesomes,...

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  • 2014
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    Velo

    Velo

    1 2014 HD

    The Velo bike messenger boys work long hours navigating new relationships, overbearing bosses and upset customers in an unforgiving urban...

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  • 2015
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    Helix Real Cam: Bareback Boyfriends

    Helix Real Cam: Bareback Boyfriends

    7 2015 HD

    The GoPro cameras are back to capture more amateur Porn Star action with the Helix Real Cam™. Experience the love life of Max & Kyle as they...

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  • 2015
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    Horny Schoolboys

    Horny Schoolboys

    1 2015 HD

    Homework can be boring enough on its own, but it’s totally impossible to focus on solving math problems or memorize historical dates when...

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  • 2014
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    Bareback Boys 3

    Bareback Boys 3

    1 2014 HD

    Join us for the third, hottest-yet installment of Bareback Boys. This time around, we’re hitting you with even more ass-pounding encounters...

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  • 2014
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    Bang My Twink Hole

    Bang My Twink Hole

    1 2014 HD

    Jordan Thomas is the first twink to get his hole rocked as he loses his cherry on-screen bottoming for the adorable Evan Parker. Andy Taylor is next...

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  • 2015
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    Big Dick Bareback

    Big Dick Bareback

    1 2015 HD

    Calling all size queens, big dick worshipers, and hung-hungry pole-chasers! If you enjoy nothing more than colossal-sized cocks making raw, deep...

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  • 2013
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    Live Twink Orgy

    Live Twink Orgy

    1 2013 HD

    Are you ready for the hottest LIVE boy Sex Show in gay porn history? This all-star cast of boys ravage each other in a fuck and suckfest that will...

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  • 2015
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    Boy Stories 3: Bareback

    Boy Stories 3: Bareback

    1 2015 HD

    Welcum to our third installment of Boy Stories. In this collection of jizztastic twink "tails", we find that all different types of chemistry can...

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  • 2015
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    Dirty Blonds

    Dirty Blonds

    1 2015 HD

    Blonds come in all shades and sizes. This film highlights one particular variety: the young, hung, and full of cum. In the title scene, Lukas Grande...

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  • 2015
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    Boy Next Door

    Boy Next Door

    1 2015 HD

    The boy next door is the one you’ll always dream about. He gave you your first kiss, confided in you his deepest secrets, showed you...

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  • 2013
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    First Time Remembered 2

    First Time Remembered 2

    1 2013 HD

    Do you remember your first time? More of our hottest Helix Boys recall their first teenage escapades of cherry popping experiences including intimate...

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  • 2014
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    Boy Stories 2

    Boy Stories 2

    1 2014 HD

    What happens when ordinary everyday situations take a turn and lead to mind-blowing, ass-pounding sex? Join us for the second installment of Boy...

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  • 2015
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    Bubble Butts

    Bubble Butts

    1 2015 HD

    What’s round, juicy, and smooth all over? This is no riddle. It’s Bubble Butts, our big-ass compilation overstuffed with the bounciest...

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  • 2014
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    Man on Twink

    Man on Twink

    1 2014 HD

    Man on Twink brings together legendary Director Dominic Ford and his hung superhunks Tommy Defendi & Landon Conrad with Helix Studios own power...

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  • 2015
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    Pleasing the Boy

    Pleasing the Boy

    1 2015 HD

    There’s more than one way to please a boy. You can whisper dirty thoughts into his ear, slip your hand under his pants and grab his smooth,...

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  • 2015
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    Twink 3 Ways

    Twink 3 Ways

    1 2015 HD

    It’s been said that “two’s company, three’s a crowd”, but this collection of explosive twink 3 ways proves that when it...

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  • 2014
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    Young Lust

    Young Lust

    1 2014 HD

    Young Lust is a fiery and uncontrollable craving, an appetite to touch and devour every inch of smooth skin. With wild desires that demand to be...

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  • 2015
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    Hung & Horny

    Hung & Horny

    8 2015 HD

    Up for a challenge? Let’s see who can handle the most well-hung and horny Helix hunks as they bury their jumbo-sized boners into the tightest...

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  • 2016
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    Bareback Boys 4

    Bareback Boys 4

    1 2016 HD

    It's barely legal bareback at it's best in this all new, full-length & condom free fuck flick from Helix Studios! From super sexy boyfriends boning...

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  • 2016
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    California Boys 2

    California Boys 2

    8 2016 HD

    In this latest sizzling summertime release from Helix Studios, we return to sunny California and the wild wild boys of the wild wild west! From sexy...

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  • 2016
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    Bare Youth

    Bare Youth

    1 2016 HD

    They're young, hung and full of cum in an all new feature-length and condom free cock-buster from Helix Studios! From the classic teenage first time...

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  • 2016
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    Bareback Passion

    Bareback Passion

    1 2016 HD

    It's barely legal bareback at it's best in this all new feature-length & condom free fuck flick from Helix Studios! Whether it's a sizzling...

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  • 2016
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    Horny Heartthrobs

    Horny Heartthrobs

    9 2016 HD

    Watch as hunkzilla muscle bro Justin Owen takes on the fit and frisky jailbait juniors of Helix Studios in this sizzling hot, fap-tastic treasure...

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  • 2013
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    Raw Teen Love

    Raw Teen Love

    1 2013 HD

    These young lovers know how to loosen up a tight twink hole for some raw teen-on-teen riding. Cum loving boys know bareback is best for blowing their...

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  • 2016
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    Twink on Twink

    Twink on Twink

    1 2016 HD

    Those titans of twink-tainment are at it again and this time, the beautiful and barely legal bad boys of Helix Studios just might have outdone...

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  • 2016
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    Riding Raw

    Riding Raw

    1 2016 HD

    Helix has ASSembled 10 of their HOTTEST models for a 5 star bareback fuck-fest! With the exception of some sexy shirtless gymnastics, these boys cut...

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  • 2016
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    Bottoms Battle

    Bottoms Battle

    1 2016 HD

    Big dicked twink bottoms are some of the most captivating boys to watch. Being young and pretty is a currency these hand picked Helix boys ALL have....

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  • 2017
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    Triple Twink

    Triple Twink

    10 2017 HD

    Triple your pleasure in this tantalizingly tasty collection of twink treasures! Every scene is overflowing with THREE of the HOTTEST twinks on the...

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  • 2017
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    Twink Confessions 3

    Twink Confessions 3

    1 2017 HD

    Helix is back and exploding with ass AND answers! The boys take twitter questions and requests, answer and act out honestly and in full dirty detail!...

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  • 2020
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    Horny Harmony

    Horny Harmony

    1 2020 HD

    From tickling the ivories to tickling tonsils, from guitar hero, to hero hung hogs, these cock hungry composers, and dick destroying dancers put ALL...

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