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Scenes

PerformersJessie Montgomery Remove filter Clear all
75 results Newest first
Scenes19:43
Touch
Noah White, Jessie Montgomery Helix Studios Scenes
Scenes29:20
Slumber Party 3 Way
Grayson Lange, Brad Chase, Jessie Montgomery Helix Studios Scenes
Scenes22:28
Excellent Service
Elliott Grey, Jessie Montgomery Helix Studios Scenes
Scenes19:41
Spoiler Alert: Jessie Fucks Jackson
Jackson Clark, Jessie Montgomery Helix Studios Scenes
Scenes23:59
In the Flesh
Jessie Montgomery, Lukas Grande Helix Studios Scenes
Scenes20:43
Running Through My Mind
Jessie Montgomery, Kaleb Marshall Helix Studios Scenes
Scenes23:31
Destined to Fuck
Jessie Montgomery, Justin Owen Helix Studios Scenes
Scenes20:54
Cum Here Often?
Jessie Montgomery, Aiden Garcia Helix Studios Scenes
Scenes22:55
Better Laid Than Never
Grayson Lange, Jessie Montgomery Helix Studios Scenes
Scenes24:34
Wardrobe Strange
Jessie Montgomery, Logan Cross Helix Studios Scenes
Scenes17:23
Start Me Up
Evan Parker, Jessie Montgomery Helix Studios Scenes
Scenes22:18
Daydream with Cream
Jessie Montgomery, Tyler Hill Helix Studios Scenes
Scenes21:02
Jessie's Boy
Brad Chase, Jessie Montgomery Helix Studios Scenes
Scenes34:23
#helix: Jessie Montgomery and Greco Rai
Jessie Montgomery, Greco Rai Helix Studios Scenes
Scenes31:45
Jessie Montgomery & Matthew James
Matthew James, Jessie Montgomery Downlow Boys Scenes
Scenes21:17
Rock Out with Your Cock Out
Jessie Montgomery, Jasper Robinson Helix Studios Scenes
Scenes27:20
Bareback Flip Fuck
Max Carter, Jessie Montgomery Helix Studios Scenes
Scenes1:54:59
Big Dick Bareback (2015)
Kyle Mason, Max Carter, Davey Brooks, Dustin Gold, Jacob Dixon, Jessie Montgomery +4 others Helix Studios Scenes
Scenes20:29
Blonds by the Bay
Jessie Montgomery, Cooper Steel Helix Studios Scenes
Scenes34:28
Jessie, Luke & Deepdicc
Jessie Montgomery, Luke Allen, Deepdicc Downlow Boys Scenes
Scenes20:54
Banging Blonds
Jessie Montgomery, Matt Klein Helix Studios Scenes
Scenes25:17
What About Your Roommate?
Kody Knight, Jessie Montgomery, Tyler Hill Helix Studios Scenes
Scenes18:12
Eager To Fuck
Blake Mitchell, Jessie Montgomery Helix Studios Scenes
Scenes19:26
Cum With Me
Jessie Montgomery, Troy Ryan Helix Studios Scenes
Scenes23:01
Horny Hikers
Jessie Montgomery, Elijah West Helix Studios Scenes
Scenes17:07
Spank Bank
Jessie Montgomery, Dalton Briggs Helix Studios Scenes
Scenes17:08
Spooked
Jessie Montgomery, Corbin Webber Helix Studios Scenes
Scenes20:31
Yoga Thunder
Zac Stevens, Jessie Montgomery Helix Studios Scenes
Scenes22:36
Bareback Twink Laundry Day
Jessie Montgomery, Luke Allen Helix Studios Scenes
Scenes12:48
Man on Twink | The Waiting Room
Jessie Montgomery, Landon Conrad Helix Studios Scenes
Scenes14:04
Phoenix Heat for Three
Andy Taylor, Kody Knight, Jessie Montgomery Helix Studios Scenes
Scenes15:14
Rooftop Hotties
Jessie Montgomery, Travis Walker Helix Studios Scenes
Scenes28:19
Real Cam: Jessie and Alex Bareback
Jessie Montgomery, Alex Jordan Helix Studios Scenes
Scenes15:45
Swapping Selfies
Jessie Montgomery, Alex Jordan Helix Studios Scenes
Scenes25:04
Jessie and Sage
Jessie Montgomery, Sage Porter Helix Studios Scenes
Scenes46:10
Real Cam: Jessie Montgomery and Jamie Sanders
Jessie Montgomery, Jamie Sanders Helix Studios Scenes
Scenes26:45
Scandal at Helix Academy: Chapter III
Evan Parker, Jessie Montgomery, Ryker Madison, Zayne Donovan Helix Studios Scenes
Scenes28:36
Tub for Two
Andy Taylor, Jessie Montgomery Helix Studios Scenes
Scenes34:48
Study Group
Matthew Keading, Aiden Summers, Jacob Dixon, Jessie Montgomery, Mitch Hudson Helix Studios Scenes
Scenes23:36
VELO | Part Five: The Boyfriend
Matthew Keading, Jessie Montgomery Helix Studios Scenes
Scenes22:22
Luke and Jessie's Twinkmas
Jessie Montgomery, Luke Allen Helix Studios Scenes
Scenes7:01
Helix Collections - Bareback Banging Vol 1
Jessie Montgomery, Damon Archer, Jamie Sanders, Daniel Bishop Helix Studios Scenes
Scenes28:47
Coming Home
Jacob Dixon, Jessie Montgomery Helix Studios Scenes
Scenes21:53
Puppy Lovin'
Jessie Montgomery, Dylan Hall Helix Studios Scenes
Scenes3:07
Helix Collections - Boys Kissing Volume 1
Andy Taylor, Matthew Keading, Roman Daniels, Scotty Clarke, Jessie Montgomery, Damon Archer Helix Studios Scenes
Scenes13:04
Jessie's Photo Shoot
Evan Parker, Jessie Montgomery Helix Studios Scenes
Scenes8:03
Helix Academy Behind the Scenes
Victor Hoff, Anderson Lovell, Chase Young, Evan Parker, Jessie Montgomery, Kellan Parker +1 others 8teenBoy Scenes
Scenes14:23
Helix Academy 2 | Episode 8: Looking Back
Jessie Montgomery, Jamie Sanders Helix Studios Scenes