Luke Allen & Jessie Montgomery in Luke and Jessie's Twinkmas - HelixStudios

Jessie Montgomery & Lukas Grande in In the Flesh - HelixStudios

Kyle Ross & Jessie Montgomery & Ian Levine in A Twilight Bareback DP - HelixStudios

Jessie Montgomery & Jamie Sanders & Daniel in Helix Collections - Bareback Banging Vol 1 - HelixStudios

Luke Allen & Jessie Montgomery & Evan Parker in Helix Academy 1 - Episode 1: The New Kid - HelixStudios

Blade Woods & Jessie Montgomery in Bareback Massage - HelixStudios

Jessie Montgomery in First There Was Light - HelixStudios

Jessie Montgomery & Elliott Grey in Excellent Service - HelixStudios

Jessie Montgomery & Greco Rai in #helix: Jessie Montgomery and Greco Rai - HelixStudios

Jessie Montgomery & Matthew Keading & Ty in VELO - Part One: The Architect - HelixStudios

Jessie Montgomery & Brad Chase in Jessie's Boy - HelixStudios

Jessie Montgomery & Matthew Keading in VELO - Part Five: The Boyfriend - HelixStudios

Jessie Montgomery & Jamie Sanders in Helix Academy 2 - Episode 8: Looking Back - HelixStudios

Jessie Montgomery & Jamie Sanders in Real Cam: Jessie Montgomery and Jamie Sanders - HelixStudios

Jessie Montgomery & Scotty Clarke in Helix Academy 2 - Episode 7: Secret Crush - HelixStudios

Jessie Montgomery & Sage Porter in Jessie and Sage - HelixStudios

Max Carter & Jessie Montgomery in Bareback Flip Fuck - HelixStudios

Jessie Montgomery & Alex Jordan in Real Cam: Jessie and Alex Bareback - HelixStudios

Max Carter & Kyle Ross & Jessie Montgomery & Andy in Man On Twink Trailer - HelixStudios

Luke Allen & Jessie Montgomery in Bareback Twink Laundry Day - HelixStudios

Jessie Montgomery & Blake Mitchell in Eager To Fuck - HelixStudios

Jessie Montgomery & Logan Cross in Wardrobe Strange - HelixStudios

Jessie Montgomery & Matthew Keading in VELO - Teaser - HelixStudios

Jessie Montgomery & Daniel Bishop in Morning Bareback - HelixStudios

Jessie Montgomery & Austin Ried in Austin Dribbles Jessie's Balls - HelixStudios

Jessie Montgomery & Dalton Briggs in Spank Bank - HelixStudios

Jasper Robinson & Jessie Montgomery in Rock Out with Your Cock Out - HelixStudios

Jessie Montgomery & Casey Tanner & Gabriel West in From the Bath to the Bed - HelixStudios

Jessie Montgomery & Dominic Jones in Jessie's Boy Hole Pounded Live - HelixStudios

Jessie Montgomery & Cooper Steel in Blonds by the Bay - HelixStudios

Jessie Montgomery & Corbin Webber in Spooked - HelixStudios

Jessie Montgomery & Evan Parker & Casey Tanner in Scandal at Helix Academy Teaser - HelixStudios

Christian Collins & Jessie Montgomery in Christmas Cums Early - HelixStudios

Jessie Montgomery & Kaleb Marshall in Running Through My Mind - HelixStudios

Jessie Montgomery & Aiden Summers in A First time Remembered - HelixStudios

Jessie Montgomery & Justin Owen in Destined to Fuck - HelixStudios

Jessie Montgomery & Damon Archer in Bareback Pool Party - HelixStudios

Jessie Montgomery & Matt Klein in Banging Blonds - HelixStudios

Jessie Montgomery & Dylan Hall in Puppy Lovin' - HelixStudios

Jessie Montgomery & Evan Parker in Start Me Up - HelixStudios

Jessie Montgomery & Grayson Lange in Better Laid Than Never - HelixStudios

Jasper Robinson & Jessie Montgomery in Jessie and Jasper - HelixStudios

Jessie Montgomery & Alex Jordan in Swapping Selfies - HelixStudios

Jessie Montgomery & Brad Chase & Grayson Lange in Slumber Party 3 Way - HelixStudios

Jessie Montgomery & Jackson Clark in Spoiler Alert: Jessie Fucks Jackson - HelixStudios

Jessie Montgomery & Evan Parker & Ryker Madison in Scandal at Helix Academy: Chapter III - HelixStudios

Jessie Montgomery & Evan Parker in Jessie's Flirty Fuck - HelixStudios

Jessie Montgomery & Zac Stevens in Yoga Thunder - HelixStudios

Jessie Montgomery & Aiden Summers & Matthew in Study Group - HelixStudios

Jessie Montgomery & Jacob Dixon in Coming Home - HelixStudios

Jessie Montgomery & Noah White in Touch - HelixStudios

Jessie Montgomery & Tyler Hill in Daydream with Cream - HelixStudios

Jessie Montgomery & Kody Knight & Tyler Hill in What About Your Roommate? - HelixStudios

Chase Young & Jessie Montgomery in The Great Outdoor Banging - HelixStudios

Anderson Lovell & Jessie Montgomery in Helix Academy 1 - Episode 3: Detention - HelixStudios

Jessie Montgomery & Aiden Garcia in Cum Here Often? - HelixStudios

Jessie Montgomery & Connor Maguire in Blond Boy's Ass Abused - HelixStudios

Jessie Montgomery & Casey Tanner & Kellan Parker in Helix Academy 1 - Episode 2: Peeping Through - HelixStudios

Jessie Montgomery & Ian Levine & Andy Taylor in Phoenix Heat for Three - HelixStudios

Jessie Montgomery & Evan Parker in Jessie's Photo Shoot - HelixStudios