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r/JackOffToPlayboy

57,052 subscribers
If you love jacking to Playboy babes, this is your group. Show us the girl that gets your dick hard. Talk about how hard she's making you. Keep it chill and respectful.

Moderators

Updated May 9, 2024
u/Firely2002JA Active
Added 4 years ago

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 Junior_Reputation120
2 days ago
Preview thumbnail for Per request, the Legendary Cindy Crawford in her October 1998 Playboy shoot! Added some 1993 and other hot photos of her as well image
Per request, the Legendary Cindy Crawford in her October 1998 Playboy shoot! Added some 1993 and other hot photos of her as well
to r/JackOffToPlayboy by TeddyWestCyanide
1 month ago
Preview thumbnail for Shelly Jamison was a busty newswomen... I remember busting to her over and over. image
Shelly Jamison was a busty newswomen... I remember busting to her over and over.
to r/JackOffToPlayboy by BJ-Stroker
1 month ago
Preview thumbnail for Who is more likely to make you break out the lube? Cynthia Myers or Candy Loving? image
Who is more likely to make you break out the lube? Cynthia Myers or Candy Loving?
to r/JackOffToPlayboy by sweetgumtea
1 month ago
Preview thumbnail for Jeana Tomosino image
Jeana Tomosino
to r/JackOffToPlayboy by Imaginary_Builder652
1 month ago
Preview thumbnail for Hope you're having a wonderful Saturday. Mine's would be spent jacking off to Leanna Decker's perfect body. image
Hope you're having a wonderful Saturday. Mine's would be spent jacking off to Leanna Decker's perfect body.
to r/JackOffToPlayboy by BJ-Stroker
2 months ago
Preview thumbnail for Nowadays, I prefer natural, but when I was 18 and saw Nadine Chanz’s perfect tits, I dropped my pants immediately image
Nowadays, I prefer natural, but when I was 18 and saw Nadine Chanz’s perfect tits, I dropped my pants immediately
to r/JackOffToPlayboy by BJ-Stroker
2 months ago
Preview thumbnail for If you had to choose one playmate whom you consider “Lube Worthy”, who would you choose? Janet Lupo, especially as a milf, is mine. image
If you had to choose one playmate whom you consider “Lube Worthy”, who would you choose? Janet Lupo, especially as a milf, is mine.
to r/JackOffToPlayboy by Imaginary_Builder652
1 month ago
Preview thumbnail for Ashleigh Rae pushed me to the edge this Christmas image
Ashleigh Rae pushed me to the edge this Christmas
to r/JackOffToPlayboy by Imaginary_Builder652
1 month ago
Preview thumbnail for One of my favourite pic to jack off to. Alejandra Guilmant. image
One of my favourite pic to jack off to. Alejandra Guilmant.
to r/JackOffToPlayboy by DanWhackersReturns
2 months ago
Preview thumbnail for I need a maid like SJU image
I need a maid like SJU
to r/JackOffToPlayboy by Logical-Sir-6471
2 months ago
Watching PB Vids With Other Fans
to r/JackOffToPlayboy by BJ-Stroker
2 months ago
Preview thumbnail for I’m not usually a fan of enhanced tits, but when I found my brother’s Playboy with Julianna Young, I jerked off to her over 10 times in 3 days image
I’m not usually a fan of enhanced tits, but when I found my brother’s Playboy with Julianna Young, I jerked off to her over 10 times in 3 days
to r/JackOffToPlayboy by BJ-Stroker
2 months ago
Preview thumbnail for Janet Lupo’s massive tits make me feel much more perverted when I wank image
Janet Lupo’s massive tits make me feel much more perverted when I wank
to r/JackOffToPlayboy by BJ-Stroker
3 months ago
Preview thumbnail for Nothing gets my juices flowing like vintage big tits like those of Elaine Reynolds image
Nothing gets my juices flowing like vintage big tits like those of Elaine Reynolds
to r/JackOffToPlayboy by BJ-Stroker
3 months ago
Preview thumbnail for Do Patricia Farinelli’s beautiful big tits make anyone else want to start stroking immediately? image
Do Patricia Farinelli’s beautiful big tits make anyone else want to start stroking immediately?
to r/JackOffToPlayboy by jeanlucverge
3 months ago
Preview thumbnail for Bush love. SO luxurious image
Bush love. SO luxurious
to r/JackOffToPlayboy by jeanlucverge
3 months ago
Preview thumbnail for Seeking Michigan JO partner to appreciate Carmen Berg. image
Seeking Michigan JO partner to appreciate Carmen Berg.
in Michigan
to r/JackOffToPlayboy by jeanlucverge
3 months ago
Preview thumbnail for Luann Lee has the prettiest bush and puffy nipples image
Luann Lee has the prettiest bush and puffy nipples
to r/JackOffToPlayboy by jeanlucverge
3 months ago
Luann Lee had the prettiest bush and puffy nipples. Stroke my cock to her still today.
to r/JackOffToPlayboy by jeanlucverge
3 months ago
Preview thumbnail for Is this the hottest playmate pic ever? image
Is this the hottest playmate pic ever?
to r/JackOffToPlayboy by BJ-Stroker
3 months ago
Preview thumbnail for Janet Lupo’s massive tits always make me want to break out the lube and have a sloppy jerk image
Janet Lupo’s massive tits always make me want to break out the lube and have a sloppy jerk
to r/JackOffToPlayboy by AnjaLittle
2 months ago
Preview thumbnail for Yes I copied Pam Anderson… so what??? 🤣 image
Yes I copied Pam Anderson… so what??? 🤣
to r/JackOffToPlayboy by Hentai_Zaibatsu
4 months ago
Preview thumbnail for Take a good look at Roberta Vasquez! What's your favorite pose of her? My cock can never get enough! image
Take a good look at Roberta Vasquez! What's your favorite pose of her? My cock can never get enough!
to r/JackOffToPlayboy by daviddeclerq
4 months ago
Preview thumbnail for Jennifer Walcott’s wet, round assets just look so great and huge here, I am obsessed image
Jennifer Walcott’s wet, round assets just look so great and huge here, I am obsessed
to r/JackOffToPlayboy by Both_Possibility_601
4 months ago
Who was your first playmate?