Originally a custom video, but no names are used.
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Your Girlfriend's Step-Mom Has One Rule
#Cougar
#First Time
#Girlfriend
#MILF
#Older Woman / Younger Man
#POV
#Stepmom
#Stepmommy
#Taboo
#Virtual Sex
$20.00
$16.00
Jun 06, 2026
•
31:21
2K
Jun 11, 2026
•
Stream and Download
•
6.85 GB
•
31:21
2K
Tonight, you're going on your first official date with your new girlfriend. Both of you are nervous, inexperienced, and determined to make a good first impression. You arrive a little early, and your girlfriend is still getting ready upstairs. Mrs. Wood warmly greets you and ushers you inside. You find her intimidating, but try your best not to let it show. After what feels uncomfortably like a formal interview, she bluntly asks you what your intentions with her "step-daughter" are. She knows boys your age are slaves to their sexual urges, and needs your assurance that you'll be on your best behavior. You shyly explain you're a virgin and have no lustful intentions. She commends you for saving yourself, but even good boys can slip up around pretty women—it's in their nature. The only way she can be certain you'll behave is if she takes the edge off and sexually satisfies you herself. She assures you that your girlfriend is aware of the house rule regarding dating, and has long understood that Mrs. Wood is the only one permitted to have sex with the boys she brings home. It's in your girlfriend's best interest, after all—an act of love. How else could "Step-Mommy" keep her safe?
Jun 11, 2026
•
Stream and Download
•
6.85 GB
•
31:21
2K
Tonight, you're going on your first official date with your new girlfriend. Both of you are nervous, inexperienced, and determined to make a good first impression. You arrive a little early, and your girlfriend is still getting ready upstairs. Mrs. Wood warmly greets you and ushers you inside. You...
Tonight, you're going on your first official date with your new girlfriend. Both of you are nervous, inexperienced, and determined to make a good first impression. You arrive a little early, and your girlfriend is still getting ready upstairs. Mrs. Wood warmly greets you and ushers you inside. You find her intimidating, but try your best not to let it show. After what feels uncomfortably like a formal interview, she bluntly asks you what your intentions with her "step-daughter" are. She knows boys your age are slaves to their sexual urges, and needs your assurance that you'll be on your best behavior. You shyly explain you're a virgin and have no lustful intentions. She commends you for saving yourself, but even good boys can slip up around pretty women—it's in their nature. The only way she can be certain you'll behave is if she takes the edge off and sexually satisfies you herself. She assures you that your girlfriend is aware of the house rule regarding dating, and has long understood that Mrs. Wood is the only one permitted to have sex with the boys she brings home. It's in your girlfriend's best interest, after all—an act of love. How else could "Step-Mommy" keep her safe?
Originally a custom video, but no names are used.
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