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r/JackOffToPlayboy

52,290 subscribers

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

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to r/JackOffToPlayboy by Both_Possibility_601
3 months ago
Preview thumbnail for Three cheers for Hiromi! image
Three cheers for Hiromi!
to r/JackOffToPlayboy by pleasure_wak42
1 month ago
Preview thumbnail for Julie McCullough’s acting career was threatened when Kirk Cameron was born again image
Julie McCullough’s acting career was threatened when Kirk Cameron was born again
to r/JackOffToPlayboy by pleasure_wak42
3 months ago
Preview thumbnail for Looking back at some girls who became Playmate of the Month. Anyone here make you wanna have a second look? I wonder if today’s era will ever eclipse yesteryear. Is the only way to have an hourglass shape to see the surgeon? Does Playboy Plus stand for plus sized? image
Looking back at some girls who became Playmate of the Month. Anyone here make you wanna have a second look? I wonder if today’s era will ever eclipse yesteryear. Is the only way to have an hourglass shape to see the surgeon? Does Playboy Plus stand for plus sized?
to r/JackOffToPlayboy by TailorSpecialist5938
3 months ago
Preview thumbnail for I realized that I've been using the term "ball drainer" whenever I jerk off so I told myself to use it less often. But damn it, Shanna Marie McLaughlin is a certified ball drainer. Every inch of her body just oozes pleasure image
I realized that I've been using the term "ball drainer" whenever I jerk off so I told myself to use it less often. But damn it, Shanna Marie McLaughlin is a certified ball drainer. Every inch of her body just oozes pleasure
to r/JackOffToPlayboy by Sf52016
3 months ago
Preview thumbnail for I still remember my jaw dropping when I saw this picture of the Torrie Wilson playboy issue. It was so hot to see her in this position fully nude. So much fun that night image
I still remember my jaw dropping when I saw this picture of the Torrie Wilson playboy issue. It was so hot to see her in this position fully nude. So much fun that night
to r/JackOffToPlayboy by CrazyMiguel119
3 months ago
Preview thumbnail for Another sexy lady from the year 2000, Shannon Stewart. She is crush worthy on many levels image
Another sexy lady from the year 2000, Shannon Stewart. She is crush worthy on many levels
to r/JackOffToPlayboy by Mrandres21
1 month ago
Preview thumbnail for Enjoying these signed prints I got from the lovely playboy Germany editions Anja Little. image
Enjoying these signed prints I got from the lovely playboy Germany editions Anja Little.
in Germany
to r/JackOffToPlayboy by AnjaLittle
1 month ago
Preview thumbnail for Sorry it’s been so long. How are my Playboy Connoisseurs? image
Sorry it’s been so long. How are my Playboy Connoisseurs?
to r/JackOffToPlayboy by xbxbxxx
2 months ago
Preview thumbnail for Maria Checa - August 94 has my cock throbbing. Underrated fav. image
Maria Checa - August 94 has my cock throbbing. Underrated fav.
to r/JackOffToPlayboy by jcs782056
7 months ago
Preview thumbnail for Cooper dawn image
Cooper dawn
to r/JackOffToPlayboy by jcs782056
7 months ago
Preview thumbnail for Nibette faith image
Nibette faith
to r/JackOffToPlayboy by AnjaLittle
1 month ago
Preview thumbnail for Finally got a chance to sit down with my coffee and read the new German Playboy issue image
Finally got a chance to sit down with my coffee and read the new German Playboy issue
to r/JackOffToPlayboy by KaleidoscopeSure5890
8 months ago
Preview thumbnail for Christi Shake and her outie lips image
Christi Shake and her outie lips
to r/JackOffToPlayboy by KaleidoscopeSure5890
8 months ago
Preview thumbnail for Jacqueline from LSU in the SEC co-ed special edition - those lips down there are perfect image
Jacqueline from LSU in the SEC co-ed special edition - those lips down there are perfect
in Colorado
to r/JackOffToPlayboy by AnjaLittle
1 month ago
Preview thumbnail for I got my new Playboy (Germany)… April 2024. I just “read” the articles if anyone from Reddit asks 😉 image
I got my new Playboy (Germany)… April 2024. I just “read” the articles if anyone from Reddit asks 😉
in Germany
to r/JackOffToPlayboy by DJ_Gold42
8 months ago
18, never grew up with playboy but very interested in all things vintage porn
to r/JackOffToPlayboy by AnjaLittle
1 month ago
Preview thumbnail for Since you’ve been so nice to me here, I took a couple of special pics for you boys with a sign & the latest PB Germany issue (I’m not in it).. and some answers to your questions image
Since you’ve been so nice to me here, I took a couple of special pics for you boys with a sign & the latest PB Germany issue (I’m not in it).. and some answers to your questions
in Germany
to r/JackOffToPlayboy by AnjaLittle
1 month ago
Preview thumbnail for I hope it’s ok to post here. It’s ok to jackoff to me 😂 image
I hope it’s ok to post here. It’s ok to jackoff to me 😂
to r/JackOffToPlayboy by just-athena69
1 month ago
Preview thumbnail for Wondering if anyone has ever jacked off to this photo of mine 😋 (OC Posting - Ashley Kirk) image
Wondering if anyone has ever jacked off to this photo of mine 😋 (OC Posting - Ashley Kirk)
to r/JackOffToPlayboy by Goose_Fur
9 months ago
Preview thumbnail for Jacking my morning wood off to Erica Campbell. Feels so good today it was difficult for me to stop long enough to make this post. image
Jacking my morning wood off to Erica Campbell. Feels so good today it was difficult for me to stop long enough to make this post.
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for On German News Stands Now… just the smell of opening a new Playboy magazine gets me excited and rock hard today as it did way back in my youth image
On German News Stands Now… just the smell of opening a new Playboy magazine gets me excited and rock hard today as it did way back in my youth
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for German PB model Anja Little can hold on while I lick her image
German PB model Anja Little can hold on while I lick her
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for Miss Feb from Germany looks so hot in the wall. It’s hard to WFH when all I can think about is tasting her delicious pussy image
Miss Feb from Germany looks so hot in the wall. It’s hard to WFH when all I can think about is tasting her delicious pussy
in Germany
to r/JackOffToPlayboy by OpenHouseXXX
4 months ago
Preview thumbnail for Stephanie Adams was the 1st PMOM that came to my new step-dad in the mail. Shot my first load to this centerfold image
Stephanie Adams was the 1st PMOM that came to my new step-dad in the mail. Shot my first load to this centerfold
to r/JackOffToPlayboy by Ok-Coyote-9321
11 months ago
Question about a playmate that I'm having trouble finding.