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Jessie Montgomery (627)

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Jessie Got That Big Booty Jessie Rogers, Trey
68%
4:59

Jessie Got That Big Booty Jessie Rogers, Trey

11 months ago ft. Jessie Rogers

Jessie Rogers Hardcore Gangbang
71%
52:52

Jessie Rogers Hardcore Gangbang

1 year ago ft. Jessie Rogers

BLACKED Naughty Cheater Jessie Rogers Wants A Taste Of His BBC
73%
12:26

BLACKED Naughty Cheater Jessie Rogers Wants A Taste Of His BBC

1 year ago ft. Jessie Rogers

Montgomery gator balls
90%
0:26

Montgomery gator balls

1 year ago

BANGBROS - Watch Jessie Rogers's Bubble Butt Get Pounded By Her Stepbrother's Thick Dick
70%
10:01

BANGBROS - Watch Jessie Rogers's Bubble Butt Get Pounded By Her Stepbrother's Thick Dick

1 year ago ft. Jessie Rogers

TUSHY Curvy Beauty Jessie Rogers Has Intense Anal With Her Boss
71%
12:27

TUSHY Curvy Beauty Jessie Rogers Has Intense Anal With Her Boss

9 months ago ft. Jessie Rogers

BLACKED Naughty Cheater Jessie Rogers wants a Taste of his BBC
91%
15:26

BLACKED Naughty Cheater Jessie Rogers wants a Taste of his BBC

1 year ago ft. Jessie Rogers

JESSIE ROGERS DOUBLE PENETRATION 3-WAY
78%
6:08

JESSIE ROGERS DOUBLE PENETRATION 3-WAY

2 years ago ft. Jessie Rogers

GF CHEATED so I Fucked her Friend with the BIGGEST BOOTY - Jessie Rogers
91%
14:33

GF CHEATED so I Fucked her Friend with the BIGGEST BOOTY - Jessie Rogers

1 year ago ft. Jessie Rogers

Busty Jessie Rogers Hooks Up With Big Dick Guy
77%
6:31

Busty Jessie Rogers Hooks Up With Big Dick Guy

7 months ago ft. Jessie Rogers

Jessie Rogers gets a visit from the BBC police
72%
15:55

Jessie Rogers gets a visit from the BBC police

1 year ago ft. Jessie Rogers

Montgomery having sex with Vanny
86%
0:20

Montgomery having sex with Vanny

2 years ago

Mae Montgomery & Her 38J-cups
99%
10:01

Mae Montgomery & Her 38J-cups

1 year ago

Jessie (Pokémon) Compilation
79%
4:13

Jessie (Pokémon) Compilation

2 years ago

Jessie loves it hard from behind
65%
10:44

Jessie loves it hard from behind

1 year ago ft. Jessie Rogers

TRUE ANAL Catastrophe: Jessie Rogers
88%
12:00

TRUE ANAL Catastrophe: Jessie Rogers

10 months ago

Ersties - Jessie's Sexual Fantasy Ep 1 of 2 - Jessie Wishes for a Hot Threesome for her Birthday
91%
30:22

Ersties - Jessie's Sexual Fantasy Ep 1 of 2 - Jessie Wishes for a Hot Threesome for her Birthday

1 year ago

BLACKEDRAW Jessie goes Airtight in Crazy 4-BBC Gangbang
91%
12:00

BLACKEDRAW Jessie goes Airtight in Crazy 4-BBC Gangbang

2 years ago ft. Jessie Rogers

OMG My BIG Cocked Stepson Clapped My Cheeks For St.Patty's Day - Jessie Rogers - MyPervyFamily
100%
32:30

OMG My BIG Cocked Stepson Clapped My Cheeks For St.Patty's Day - Jessie Rogers - MyPervyFamily

1 year ago ft. Jessie Rogers

GIRLSWAY - MILF Jessie Rogers Catches stepbae Kimmy Kimm Squirting On Her Petite Friends' Face
70%
16:05

GIRLSWAY - MILF Jessie Rogers Catches stepbae Kimmy Kimm Squirting On Her Petite Friends' Face

7 months ago ft. Coco Lovelock

MILFY BBC-Hungry Beauty Jessie Shows Off New Lingerie
71%
12:26

MILFY BBC-Hungry Beauty Jessie Shows Off New Lingerie

2 years ago ft. Jessie Rogers

Booty Legend Jessie Rogers Pussy Dripping Wet
80%
7:25

Booty Legend Jessie Rogers Pussy Dripping Wet

7 months ago ft. Jessie Rogers

GF CHEATED so I fucked her friend with the BIGGEST BOOTY - Jessie Rogers
80%
14:30

GF CHEATED so I fucked her friend with the BIGGEST BOOTY - Jessie Rogers

1 year ago ft. Jessie Rogers

Juicy Pussy Jessie Rogers, Tony
80%
8:00

Juicy Pussy Jessie Rogers, Tony

11 months ago ft. Tony

OhMyHoles - Jessie Ames - Threesome Sex Stream
91%
10:45

OhMyHoles - Jessie Ames - Threesome Sex Stream

1 year ago

Valentine Pussy Feast with Jane Wilde, Jessie Saint, and Mackenzie Moss
91%
36:10

Valentine Pussy Feast with Jane Wilde, Jessie Saint, and Mackenzie Moss

1 year ago ft. Jane Wilde

Come here and Fuck me, Old Man! Sweet Jessie Ames for OldHans
71%
5:16

Come here and Fuck me, Old Man! Sweet Jessie Ames for OldHans

4 months ago ft. Jessie Ames

BLACKEDRAW Jessie Goes Airtight In Crazy 4-BBC Gangbang
63%
12:26

BLACKEDRAW Jessie Goes Airtight In Crazy 4-BBC Gangbang

2 years ago ft. Jessie Rogers

HUNT4K. Best Worst Mistake. Hot sex with Jessie Clark
99%
14:11

HUNT4K. Best Worst Mistake. Hot sex with Jessie Clark

1 year ago ft. Charlie Dean

TLoU - Jessie fucks and cumshots Ellie - 3D Animation
99%
2:58

TLoU - Jessie fucks and cumshots Ellie - 3D Animation

1 year ago

TAKING TURNS ON JESSIE - they Fucked her all NIght
91%
7:10

TAKING TURNS ON JESSIE - they Fucked her all NIght

1 year ago ft. Tiktok Sluts

Love Watching My Wife's Booty Clap Back on a Monster Cock - Jessie Rogers
72%
11:12

Love Watching My Wife's Booty Clap Back on a Monster Cock - Jessie Rogers

1 year ago ft. Jessie Rogers

Stunning Big Booty Brazilian Jessie Rogers Hardcore Anal Fucking
67%
12:10

Stunning Big Booty Brazilian Jessie Rogers Hardcore Anal Fucking

2 years ago ft. Jessie Rogers

Jessie Rogers is riding Bruce Venture outdoors
87%
3:03

Jessie Rogers is riding Bruce Venture outdoors

2 years ago ft. Jessie Rogers

Jessie Rogers gets DP'ed by BBC'S
86%
6:08

Jessie Rogers gets DP'ed by BBC'S

2 years ago

BANGBROS - Jessie Rogers Flashes her Ass to her Stepbrother and Lets him Bury his Face in it
91%
15:30

BANGBROS - Jessie Rogers Flashes her Ass to her Stepbrother and Lets him Bury his Face in it

1 year ago ft. Jessie Rogers

BRAZZERS - Jessie Rogers Seduces Her Husband's Friend Bruce Venture, Then Gets All Her Holes Pounded
62%
10:30

BRAZZERS - Jessie Rogers Seduces Her Husband's Friend Bruce Venture, Then Gets All Her Holes Pounded

1 year ago ft. Jessie Rogers

From Chores to Whores, Jessie Soars - Ziggy Star, Jessie Rogers | FreeuseMa
73%
8:00

From Chores to Whores, Jessie Soars - Ziggy Star, Jessie Rogers | FreeuseMa

1 year ago ft. Jessie Rogers

TUSHYRAW Curvaceous Cutie Jessie Gapes Wide Open for you
91%
12:00

TUSHYRAW Curvaceous Cutie Jessie Gapes Wide Open for you

2 years ago ft. Jessie Rogers

Wife lana seduces babysitter Jessie
77%
30:28

Wife lana seduces babysitter Jessie

2 years ago ft. Jessie Andrews

Jessie Montgomery, born on August 28, 1993, in Estherville, Iowa, USA, is a Caucasian American gay adult film performer. Standing 5 feet 8 inches tall and weighing 129 pounds, with blond hair and blue eyes, he launched his career in 2012 at age 19, specializing in the twink genre for Helix Studios. Active until 2016, he starred in over 50 titles, demonstrating versatility as a top, bottom, and in group scenes, often featuring bareback action. Key films include 'Helix Academy' (2013), 'Out in the Open 1' (2013), and 'Bareback Night and Day' (2013).

He earned multiple 2014 Grabby Award nominations, such as Best Actor, Best Duo, Best Group Sex Scene, Hottest Bottom, and Best Newcomer. Later, he appeared in interracial scenes for Dogfart Network. Now retired, he embraces life as a 'porn zaddy,' thrift store model, and self-proclaimed sexier twin from Iowa Lakes.