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first date sex
23,126
matching results
Best Worst Dates: Episode 4
Blain O'Connor
•
Flynn Fenix
BY:
Cocky Boys
Aug 05, 2025
6.1k
75%
If You Want to Fuck on Your First Date, You Should Get Fucked First!
Adam Lancer
•
Adam Tyme
BY:
Say Uncle's Brother Crush
May 07, 2026
4.8k
80%
Dessert (Johnny Hands Tops Andy Taylor) (Bareback)
Andy Taylor
•
Johnny Hands
BY:
Helix Studios
Oct 07, 2019
10.5k
85%
Blind Date
Sam Ledger
•
Ander Wolfson
BY:
Helix Studios
Apr 17, 2022
6k
83%
Save The Date
Adam X Lee
•
Kai Carter
BY:
Chaos Men
Aug 28, 2026
3.5k
80%
Twinks Fuck On The First Date
Kenton Tore
•
Karol Gajda
BY:
Doggy Boys
Jul 14, 2020
3k
75%
Hot Stuff: First Date - Xavi Duran, Devian
Xavi Duran
•
Devian
BY:
Kristen Bjorn
Nov 02, 2019
8.5k
93%
Blind Date
Garrett Kinsley
•
Sam Ledger
BY:
Helix Studios
Mar 27, 2022
3.5k
100%
Beach Crush
Jay Tee
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Jake Waters
BY:
Next Door Studios
Apr 05, 2021
3.7k
80%
First Date Fuck (Johnny Rapid Fucks Jake Ashford)
Johnny Rapid
•
Jake Ashford
BY:
MEN.com
Oct 08, 2019
13k
59%
Pre-Date Fuck Lessons At Home
Dick Dawson
•
DevinBWC
BY:
Say Uncle's Family Dick
Oct 03, 2026
3.2k
50%
Stepbrother's Hot Date
Chanel Santini
•
Gabriel Dalessandro
BY:
Transsensual
Oct 19, 2019
5.3k
92%
Afternoon Play Date: Big C Fucks Zac Snow Preview
Jared Tyler
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Big C
•
Zac Snow
BY:
TheBigCMen
Apr 22, 2021
3.5k
100%
Trading Up
Max Mabry
•
Dieter Wolfe
BY:
Chaos Men
Apr 17, 2026
1.5k
0%
Blind Date, Deep Connection: Hunter & Roman Todd
Roman Todd
•
Hunter Graham
BY:
Cocky Boys
Jul 18, 2025
5.4k
79%
Movie Date
Jayden Marcos
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Omar Zayden
BY:
Next Door Studios
Jul 09, 2025
5.8k
64%
Strokin' Off
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Logan Aarons
BY:
MEN.com
Oct 16, 2023
6k
26%
Win A Date With A Pornstar
Roman Todd
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Ben Masters
BY:
Next Door Studios
Mar 02, 2023
6.2k
50%
My Neighbor's A Lesbo!? - Payton Preslee & Kuleana
BY:
Devil's Film
May 16, 2021
1.3k
0%
OnlyTrans - Cherry Mavrick & Janie Blade
Janie Blade
BY:
Devil's Film
Jan 13, 2022
1.4k
0%
Daddy Dearest
Khloe Kay
•
Draven Navarro
BY:
Transsensual
Jul 06, 2020
3.2k
0%
Daddy's Date Night
Pavel Sora
BY:
Bring Me A Boy!
Feb 14, 2020
3.3k
100%
Blind Date
Casey Kisses
•
Chad Diamond
BY:
Transsensual
Oct 19, 2019
7.8k
59%
Porn Date, Part 2
Damien Crosse
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Adam Wirthmore
BY:
MEN.com
Oct 10, 2019
9.5k
60%
Sauna Nights 1: First Date
Zak Bishop
•
Jessie Lee
BY:
Peter Fever
Jun 15, 2021
2.8k
0%
First Date Fuck (Brandon Jones and XL)
Brandon Jones
•
XL
BY:
Next Door Ebony
Oct 09, 2019
7.4k
84%
Sweet Talking
Pierce Paris
•
Casey Kisses
BY:
Transsensual
Oct 19, 2019
11.1k
88%
Tantric Sex Date
Chris Harder
•
Windom Gold
BY:
HIMEROS.tv
Nov 30, 2020
2.4k
100%
Step-Dad's Banana BJ
Ty Roderick
•
Benny Fox
BY:
ASG Max's Family Creep
Nov 28, 2025
4.9k
57%
SCREAM CREAM!
Michael Jackman
•
Evan Knoxx
BY:
Cocky Boys
Oct 26, 2023
4.6k
28%
It's Complicated, Scene 4
David Zayn
•
Reign
BY:
Falcon Studios
Nov 17, 2021
9k
60%
A Good Look
Jason Mack
•
Greyson Lane
BY:
Next Door Twink
Sep 28, 2019
2.8k
0%
Boy Date
Hunter Graham
•
Bryce Foster
BY:
Helix Studios
May 04, 2018
3.9k
100%
Porn Date, Part 1
Paddy O'Brian
•
Adam Wirthmore
BY:
MEN.com
May 03, 2014
17k
94%
Blind Date, Part 2
Jacob Hansen
•
Brett Daniels
BY:
Helix Studios
Apr 09, 2022
3.3k
100%
After The Sex: Rain Date
Dalton Riley
•
Beau Butler
BY:
Next Door Raw
Apr 10, 2021
4.4k
100%
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