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The matcher pulled 238 scenes with strong tag overlap on Misty Caitlin takes a personal interest in her student’s progress by delivering a private, hands-on lesson he’ll never forget. What ties these together: my first sex teacher, professor, and sexy milf. Scroll for the rest of the matches.

Professor Richelle Ryan rewards her eager student with her MILF pussy
Professor Richelle Ryan rewards her eager student with her MILF pussy
Naughty America VR43m
Jun 13, 2024
Professor Bridgette B. needs a ride home but first needs a ride on some dick
Professor Bridgette B. needs a ride home but first needs a ride on some dick
Naughty America VR51m
May 16, 2024
Professor Elizabeth Skylar gets in touch with the campus gigolo
Professor Elizabeth Skylar gets in touch with the campus gigolo
Naughty America VR43m
Apr 25, 2024
Anna Claire Clouds & Jazmin Luv get dirty in detention, but the real lesson begins when the professor catches them—and decides to join the double-team
Anna Claire Clouds & Jazmin Luv get dirty in detention, but the real lesson begins when the professor catches them—and decides to join the double-team
Naughty America VR1h 10m
May 27, 2026
Two hot coeds and a hot MILFy professor share your hard cock and big load
Two hot coeds and a hot MILFy professor share your hard cock and big load
Naughty America VR1h 7m
May 6, 2026
Sexy college professor Ivy LeBelle gives you a hands on sex education
Sexy college professor Ivy LeBelle gives you a hands on sex education
Naughty America VR46m
Nov 18, 2025
Vacationing professors Brittany Andrews, Ryder Skye, and Claudia Valentine invite a stud to their beach house
Vacationing professors Brittany Andrews, Ryder Skye, and Claudia Valentine invite a stud to their beach house
Naughty America VR49m
Jul 22, 2025
Professors Diamond Kitty, Nina Elle, and Tia Cyrus have no choice but to test your virility
Professors Diamond Kitty, Nina Elle, and Tia Cyrus have no choice but to test your virility
Naughty America VR44m
Mar 4, 2025
Professors Ariella Ferrera, Eva Long, and Richelle Ryan have bone to pick with you
Professors Ariella Ferrera, Eva Long, and Richelle Ryan have bone to pick with you
Naughty America VR44m
Feb 25, 2025
Sexy teacher Danae Mari gives her student a naughty farewell gift
Sexy teacher Danae Mari gives her student a naughty farewell gift
Naughty America VR53m
Sep 5, 2024
Busty Professor gives hard working student what he's been dreaming about
Busty Professor gives hard working student what he's been dreaming about
Naughty America VR41m
Mar 28, 2024
Professor Valentina Nappi breaks off her fling with her student but not before one last ride
Professor Valentina Nappi breaks off her fling with her student but not before one last ride
Naughty America VR45m
Feb 15, 2024
Professor Suttin has the urge to fuck you in her classroom
Professor Suttin has the urge to fuck you in her classroom
Naughty America VR47m
Jan 25, 2024
Professor Sara Jay is on the prowl for a teacher's assistant with a big cock
Professor Sara Jay is on the prowl for a teacher's assistant with a big cock
Naughty America VR40m
Jan 2, 2024
Professor McKenzie Lee has noticed your hard cock and wants you to spray your load all over her big tits
Professor McKenzie Lee has noticed your hard cock and wants you to spray your load all over her big tits
Naughty America VR44m
Aug 31, 2023
Professor Romi Rain gives you a naughty one-on-one sex education lesson
Professor Romi Rain gives you a naughty one-on-one sex education lesson
Naughty America VR36m
Aug 15, 2023
Karma Rx give YOU a hands on lesson on how to fuck a porn star
Karma Rx give YOU a hands on lesson on how to fuck a porn star
Naughty America VR33m
May 23, 2023
Your sexy teacher, Pristine Edge, gives you hands-on instructions on how to please the ladies
Your sexy teacher, Pristine Edge, gives you hands-on instructions on how to please the ladies
Naughty America VR47m
May 21, 2023
Professor Naomi Foxxx gets hot and horny for her big dick student when everyone leaves the classroom
Professor Naomi Foxxx gets hot and horny for her big dick student when everyone leaves the classroom
Naughty America VR44m
Apr 23, 2023
Bombshell pornstar Dana DeArmond will give you a 1 on 1 class on hard fucking anal!
Bombshell pornstar Dana DeArmond will give you a 1 on 1 class on hard fucking anal!
Naughty America VR41m
Apr 4, 2023
College athlete bangs his hot ass professors, Athena Anderson, Kenzie Love, and Odette Fox, between classes for extra credit
College athlete bangs his hot ass professors, Athena Anderson, Kenzie Love, and Odette Fox, between classes for extra credit
Naughty America VR1h 4m
Mar 2, 2023
Professor Sarah Jessie gets super horny with your knowledge of human anatomy and she wants you to explore all the erogenous points
Professor Sarah Jessie gets super horny with your knowledge of human anatomy and she wants you to explore all the erogenous points
Naughty America VR48m
Feb 5, 2023
Sexy professor Julia Ann shows her student Jillian Janson how to fuck a BIG dick
Sexy professor Julia Ann shows her student Jillian Janson how to fuck a BIG dick
Naughty America VR25m
Nov 14, 2022
The gorgeous Miss Brooklyn Chase teaches you how to properly fuck like a pornstar
The gorgeous Miss Brooklyn Chase teaches you how to properly fuck like a pornstar
Naughty America VR36m
Oct 17, 2022