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Jessie Montgomery & Noah White

Jul 28, 2016 - Touch: In a teenage boys bedroom filled with pillows and bunkbeds we f...

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Jessie Montgomery, Brad Chase & Grayson Lange

Jun 12, 2016 - Slumber Party 3 Way: It was just past the stroke of midnight on a dark...

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Jessie Montgomery & Elliott Grey

Apr 3, 2016 - Excellent Service: Dealing via telephone with a company's customer rel...

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Jessie Montgomery & Jackson Clark

Mar 22, 2016 - Spoiler Alert: Jessie Fucks Jackson: It can be nearly impossible to co...

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Jessie Montgomery & Lukas Grande

Mar 8, 2016 - In the Flesh: In a rare & raw instance of catfishing gone so very righ...

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Jessie Montgomery & Kaleb Marshall

Feb 9, 2016 - Running Through My Mind: Moving to a new city can sometimes be a lonel...

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Jessie Montgomery Photoshoot

Feb 1, 2016 - Jessie Montgomery Photoshoot...

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Jessie Montgomery & Justin Owen

Jan 7, 2016 - Destined to Fuck: We've all experienced it/ We all know the story. You...

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Jessie Montgomery & Aiden Garcia

Dec 15, 2015 - Cum Here Often? Party boys Aiden Garcia & Jessie Montgomery meet up at...

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Jessie Montgomery & Grayson Lange

Dec 1, 2015 - Better Laid Than Never: It's almost midnight on the streets of Hillcre...

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Jessie Montgomery & Logan Cross

Nov 15, 2015 - Wardrobe Strange: It's in the backstage dressing area before shagtime ...

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Jessie Montgomery & Evan Parker

Nov 3, 2015 - Start Me Up: Morning... The time of day when young lords sprout the wi...

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Jessie Montgomery & Tyler Hill

Sep 2, 2015 - Daydream with Cream: Running into the office crush can be awkward, ins...

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Jessie Montgomery & Greco Rai

Aug 16, 2015 - #helix: Jessie Montgomery and Greco Rai. This time on #helix, Jessie M...

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Jessie Montgomery & Max Carter

Jul 6, 2015 - What would LA Pride be without beautiful boys? So naturally, the Boys ...

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Jessie Montgomery & Cooper Steel

May 17, 2015 - Blonds by the Bay: Blond boy Jessie and a newly-blond Cooper are enjoy...

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Jessie Montgomery & Matt Klein

May 6, 2015 - Banging Blonds: Matt is telling Jessie about a recent experience hooki...

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Jessie Montgomery, Kody Knight & Tyler Hill

Apr 19, 2015 - What About Your Roommate? If you live with a roommate, you've probably...

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Jessie Montgomery & Blake Mitchell

Mar 15, 2015 - Eager To Fuck: Jessie and Blake can't wait to get behind closed doors ...

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Jessie Montgomery & Troy Ryan

Feb 1, 2015 - What is there to do after a sweaty baseball game but cool down with th...

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Jessie Montgomery & Elijah West

Jan 18, 2015 - Horny Hikers: The feeling of reaching the top of a mountain is hard to...

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Jessie Montgomery & Dalton Briggs

Jan 7, 2015 - Dalton enters his private room at the sperm bank, ready to whip out hi...

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Jessie Montgomery & Corbin Webber

Oct 29, 2014 - Spooked: Fear, excitement, and lust. Our most primal emotions are more...

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Jessie Montgomery & Zac Stevens

Oct 26, 2014 - Yoga Thunder: Finding your center takes on a whole new meaning when Za...

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Luke Allen & Jessie Montgomery

Sep 10, 2014 - Bareback Twink Laundry Day: It's laundry day for Luke Allen and Jessie...

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Jessie Montgomery & Landon Conrad

Jul 16, 2014 - Man On Twink: The Waiting Room: Landon Conrad brings his man meat to H...

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Man On Twink

Jul 3, 2014 - Featuring: Andy Taylor, Jessie Montgomery, Kody Knight, Kyle Ross, Lan...

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Andy Taylor, Kody Knight & Jessie Montgomery

May 10, 2014 - Phoenix Heat for Three: The Helix Boys descend on Phoenix Pride to put...

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Travis Walker & Jessie Montgomery

Apr 29, 2014 - Rooftop Hotties: Jessie Montgomery and new friend Travis Walker are ta...

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Jessie Montgomery & Alex Jordan

Apr 9, 2014 - Real Cam: Jessie and Alex Bareback: Jessie Montgomery and Alex Jordan ...

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Alex Jordan & Jessie Montgomery

Apr 1, 2014 - Swapping Selfies: Alex Jordan makes his Helix Studios debut when Jessi...

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Jessie Montgomery & Sage Porter

Mar 23, 2014 - Jessie Montgomery and Sage Porter give a lesson in love by reciprocati...

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Jamie Sanders & Jessie Montgomery

Feb 26, 2014 - Real Cam: Jessie Montgomery and Jamie Sanders. Boyfriends Jessie Montg...

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Evan Parker, Jessie Montgomery & Zayne Donovan

Feb 22, 2014 - Scandal at Helix Academy: Chapter III: Evan Parker is joined by Jessie...

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Jessie Montgomery & Andy Taylor

Jan 4, 2014 - Tub for Two: Jessie Montgomery and Andy Taylor's New Year's Resolution...

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Matthew Keading & Jessie Montgomery

Dec 21, 2013 - VELO: Part Five: The Boyfriend. After a long day on the bike Matthew K...

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Jessie Montgomery & Luke Allen

Dec 11, 2013 - Luke and Jessie's Twinkmas: Let Luke Allen & Jessie Montgomery help yo...

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Ty Roderick & Matthew Keading

Nov 23, 2013 - VELO: Part One: The Architect our hero Matthew Keading is forced to pa...

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Jacob Dixon & Jessie Montgomery

Oct 9, 2013 - Coming Home: Jessie Montgomery is bound for his hometown after being k...

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Dylan Hall & Jessie Montgomery

Sep 30, 2013 - Puppy Lovin' Pet owners are devoted to their pets. Dylan Hall and Jess...

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Jessie Montgomery - Photo Set Solo

Sep 10, 2013 - Helix heart-throb Jessie Montgomery gives us a candid peek into his tu...

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Helix Academy

Sep 9, 2013 - Get an inside look at the the Helix Academy twinks goofing around on s...

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Jamie Sanders, Jessie Montgomery & Evan Parker

Sep 8, 2013 - Helix Academy 8: Looking Back: Recovering from his problems at home, J...

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Jessie Montgomery & Scotty Clarke

Sep 1, 2013 - Helix Academy 7: Secret Crush: It's after hours at the Academy and alt...

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Jessie Montgomery - Shows off his sexy body

Aug 27, 2013 - Smooth blond hottie Jessie Montgomery is the next twink to model his H...

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Jessie Montgomery & Damon Archer

Aug 16, 2013 - Bareback Pool Party. What better way to spend a hot summer afternoon t...

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Helix Academy Bloopers

Aug 12, 2013 - Relive all the excitement of Helix Academy with the official Helix Aca...

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Jessie Montgomery & Daniel Bishop

Aug 4, 2013 - Cute new model Daniel Bishop and beautiful blond boy Jessie Montgomery...

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Anderson Lovell & Jessie Montgomery

Jun 4, 2013 - Sensual twinks flip fuck and suck like there is no tomorrow. It's time...

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Casey Tanner, Kellan Parker & Jessie Montgomery

May 28, 2013 - Big veiny cock splits our cock slut in half. The boarding school boys ...

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Evan Parker, Luke Allen, Jessie Montgomery & Father Glenn

May 21, 2013 - The New Kid. The first installment of Helix Academy is finally here an...

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Connor Maguire & Jessie Montgomery - Sweet tender asshole

May 18, 2013 - After forgetting his wallet at home, Connor Maguire returns to find hi...

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The Helix Academy

May 15, 2013 - Directed by Alex & Casey Roman, The Helix Academy features the hottest...

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Blade Woods & Jessie Montgomery

May 9, 2013 - Following their 5 Star fuckfest in "Bareback Massage", hot blond twink...

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Jessie Montgomery & Blade Woods

May 7, 2013 - Super hot blond twink Jessie Montgomery is in the middle of giving sex...

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Jessie Montgomery & Austin Ried

Apr 6, 2013 - Blond bombshell Jessie Montgomery spots hot jock Austin Ried playing b...

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Jordan Thomas & Jessie Montgomery

Mar 26, 2013 - Dancer boy's Jordan Thomas and Jessie Montgomery are bumpin boy bootie...

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Jessie Montgomery & Dominic Jones

Mar 26, 2013 - A Live Show Recap with Jessie Montgomery and Dominic Jones. Dominic en...

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Casey Tanner, Gabriel West & Jessie Montgomery

Mar 19, 2013 - Gabriel West is having a nice hot soak and he's about to play with his...

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Hayden Clark & Jessie Montgomery

Mar 14, 2013 - An Art Show downtown inspires Jessie Montgomery and hung stud Hayden C...

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Max Carter & Jessie Montgomery

Mar 7, 2013 - Watch this blond 18 year old's arousing performance on the stripper po...

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Evan Parker & Jessie Montgomery

Feb 5, 2013 - Jessie Montgomery and Evan Parker decide to get to know one another be...

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Christian Collins, Jessie Montgomery & Max Carter

Jan 22, 2013 - Oh to be a fly on the wall during a Helix Studios get together. Here i...

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Christian Collins & Jessie Montgomery

Dec 24, 2012 - As the lights twinkle, Christian Collins is noticing the twinkle in Je...

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Jessie Montgomery & Chase Young

Dec 11, 2012 - Chase Young and Jessie Montgomery pair up for what some may call the b...

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Jessie Montgomery

Dec 11, 2012 - Jessie Montgomery's fantasy involves him exploring himself while you w...

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Jessie Montgomery & Jasper Robinson

Nov 27, 2012 - Jasper Robinson and Jessie Montgomery are fresh off the costume party ...

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Aiden Summers & Jessie Montgomery

Nov 20, 2012 - Jessie Montgomery talks about his first time. When daddy is away the h...

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Ian Levine, Kyle Ross & Jessie Montgomery

Nov 13, 2012 - Ian Levine and Jessie Montgomery are the new kids on the block invited...

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About Jessie Montgomery

Jessie Montgomery

Name Jessie Montgomery
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Last scene with Jessie Montgomery

Jessie Montgomery & Noah White

Label: Helix Studios

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