Latest DatingMyStepson Videos

My Stepmom Is the Perfect Date
10K • Apr 16
My Stepmom Is the Perfect Date
Sophia Locke, Arin Jones DatingMyStepson
She Wants Coffee and My Cream
9.3K • Apr 1
She Wants Coffee and My Cream
Diana Grace, Gunnar Bishop DatingMyStepson
Show Me That Youre Good Enough
13K • Feb 10
Show Me That Youre Good Enough
Talia Mint, Sam Bourne DatingMyStepson
I Have to Have Her
10.1K • Jan 6
I Have to Have Her
Sharon White, Sam Bourne DatingMyStepson
I Didnt See This Cumming
19.1K • Oct 15, 2025
I Didnt See This Cumming
Shalina Devine, Nikki Nutz DatingMyStepson
Country Milf Is Too Much to Handle
13.1K • May 29, 2025
Country Milf Is Too Much to Handle
Silvia Saige, Sage Roux DatingMyStepson
Her Moms Traditional Technique
11.2K • Jan 29, 2025
Her Moms Traditional Technique
Millie Morgan, Parker Ambrose DatingMyStepson
Showing Her Mom My Best Moves
16.9K • Jan 17, 2025
Showing Her Mom My Best Moves
Bunny Madison, Parker Ambrose DatingMyStepson
Her Mom Took Me for a Test Drive
12.1K • Jan 8, 2025
Her Mom Took Me for a Test Drive
Cherry Kiss, Parker Ambrose DatingMyStepson
There Is No Resisting Her Mom
15.5K • Nov 20, 2024
There Is No Resisting Her Mom
Texas Patti, Alex Charger DatingMyStepson
Manifesting A Great Fuck
19.5K • Nov 1, 2024
Manifesting A Great Fuck
Veronica Leal, Alex Charger DatingMyStepson
Dropping My Balls In Her Moms Pocket
17.8K • Oct 18, 2024
Dropping My Balls In Her Moms Pocket
Rebecca Volpetti, Alex Charger DatingMyStepson
A Game Of Dare Always Spices Things Up
16.9K • Oct 3, 2024
A Game Of Dare Always Spices Things Up
Shalina Devine, Alex Charger DatingMyStepson
Putting In The Effort
18.4K • May 29, 2024
Putting In The Effort
Cassie Del Isla, Juan El Caballo Loco DatingMyStepson
Learning Some New Moves
32.4K • May 16, 2024
Learning Some New Moves
Crystal Rush, Rion King DatingMyStepson
Playing My Cards Right
16.7K • May 3, 2024
Playing My Cards Right
Pristine Edge, Jayden Marcos DatingMyStepson
Coming Clean
19.8K • Mar 29, 2024
Coming Clean
Micky Muffin, Sam Bourne DatingMyStepson
All In
13.7K • Mar 20, 2024
All In
Kira Queen, Matthew Meier DatingMyStepson
Candlelit Romance
21.3K • Mar 7, 2024
Candlelit Romance
Shalina Devine, Alex Charger DatingMyStepson
Filled Up Before Dinner
17.5K • Feb 28, 2024
Filled Up Before Dinner
Shalina Devine, Sam Bourne DatingMyStepson
Pleasure By The Pool
20.8K • Feb 16, 2024
Pleasure By The Pool
Micky Muffin, Shalina Devine, Matthew Meier DatingMyStepson
It Started In The Jacuzzi
20.3K • Feb 7, 2024
It Started In The Jacuzzi
Micky Muffin, Matthew Meier DatingMyStepson
I Aced Her Hole
24.5K • Jan 25, 2024
I Aced Her Hole
Micky Muffin, Alex Charger DatingMyStepson
Going Overboard On Her Pussy
23.7K • Jan 12, 2024
Going Overboard On Her Pussy
Kira Queen, Sam Bourne DatingMyStepson
Massage Queen
23.7K • Jan 3, 2024
Massage Queen
Kira Queen, Alex Charger DatingMyStepson
Stepmoms Secret Confession
23.7K • Sep 28, 2023
Stepmoms Secret Confession
Pristine Edge, Jimmy Michaels DatingMyStepson
Riding More Than Bicycles
18.2K • Sep 27, 2023
Riding More Than Bicycles
Crystal Clark, Jimmy Michaels DatingMyStepson
Turning Up The Heat
24.2K • Sep 26, 2023
Turning Up The Heat
Cassie Del Isla, Jimmy Michaels DatingMyStepson
The Milf Youd Want To Marry
21.2K • Sep 25, 2023
The Milf Youd Want To Marry
Bunny Madison, Jimmy Michaels DatingMyStepson
Massage And More
27.1K • Sep 16, 2023
Massage And More
Sarah Taylor DatingMyStepson