Coming soon - Get a detailed view of why an account is flagged as spam!
view details

r/JackOffToPlayboy

57,052 subscribers

Notice: This subreddit is not actively monitored, so the posts here are only a small subset of what exists on reddit.

New Top (24hr) Top (Week) Top (Month)
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for Carmella DeCesare got me through a military deployment image
Carmella DeCesare got me through a military deployment
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for You going with brunette or blonde Beth Williams? image
You going with brunette or blonde Beth Williams?
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for Blew my very first load to this one. Do you remember? image
Blew my very first load to this one. Do you remember?
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for While flipping through Playboy, you see your HS crush… what’s her first name? Featuring Pam Anderson, Jenny McCarthy, Anja Little, & Julia Schultz image
While flipping through Playboy, you see your HS crush… what’s her first name? Featuring Pam Anderson, Jenny McCarthy, Anja Little, & Julia Schultz
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for Miss December Playboy Germany Calendar girl image
Miss December Playboy Germany Calendar girl
in Germany
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for Just got my December issue here in Germany image
Just got my December issue here in Germany
in Germany
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for I don’t care how crazy Jenny McCarthy turned out… This Christmas issue is still epic image
I don’t care how crazy Jenny McCarthy turned out… This Christmas issue is still epic
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for I married my wife because she reminded me of Ciara Price image
I married my wife because she reminded me of Ciara Price
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for Katie Anderson has me rock hard again image
Katie Anderson has me rock hard again
to r/JackOffToPlayboy by ReasonablePie775
7 months ago
PlayboyTV - Canoga Park is missing episodes 5, 7, 9, 12
to r/JackOffToPlayboy by Mrandres21
1 year ago
Preview thumbnail for Misses December 2008, 22 years old. Jennifer and Natalie Campbell (Jennifer Has the butterfly tattoo) I wonder if any guy ever got lucky enough to have a threesome with these cuties. The rest of us can only fantasize. image
Misses December 2008, 22 years old. Jennifer and Natalie Campbell (Jennifer Has the butterfly tattoo) I wonder if any guy ever got lucky enough to have a threesome with these cuties. The rest of us can only fantasize.
to r/JackOffToPlayboy by CrazyMiguel50
10 months ago
Preview thumbnail for Ruthy Ross was sexy when she graced the pages of Playboy years ago. I can't help but still find her set sexy today. Love how she shows us so much and yet leaves some things up to our imagination. image
Ruthy Ross was sexy when she graced the pages of Playboy years ago. I can't help but still find her set sexy today. Love how she shows us so much and yet leaves some things up to our imagination.
to r/JackOffToPlayboy by CrazyMiguel50
6 months ago
Preview thumbnail for Never really watched Tonya Cooley on MTV. Perhaps if I'd known how cute she was and how her sets would fuel my fantasies, I might have watched a couple of shows that feature her. As it is, I have her set to look back on fondly. image
Never really watched Tonya Cooley on MTV. Perhaps if I'd known how cute she was and how her sets would fuel my fantasies, I might have watched a couple of shows that feature her. As it is, I have her set to look back on fondly.
to r/JackOffToPlayboy by daviddeclerq
6 months ago
Preview thumbnail for After a good Jennifer Walcott session, always fine to go back to Carmen Electra. image
After a good Jennifer Walcott session, always fine to go back to Carmen Electra.
to r/JackOffToPlayboy by CrazyMiguel50
6 months ago
Preview thumbnail for Playmate Jennifer Walcott has so many sexy photos in various Playboy publications. She was spectacular and such a tease. These are a few samples of her from various sets that really get me going image
Playmate Jennifer Walcott has so many sexy photos in various Playboy publications. She was spectacular and such a tease. These are a few samples of her from various sets that really get me going
to r/JackOffToPlayboy by DivineBladeBoy
1 year ago
Preview thumbnail for I’m gonna cum to Isabella Strangmüller tonight, the question is how many times. image
I’m gonna cum to Isabella Strangmüller tonight, the question is how many times.
to r/JackOffToPlayboy by Dick_Traci_Zords
5 months ago
Preview thumbnail for Jessica Zelinske: silicone and thigh-high boots in and on a Minnesotan never looked so fine... image
Jessica Zelinske: silicone and thigh-high boots in and on a Minnesotan never looked so fine...
in Minnesota