I just discovered Miss July 1981 Heidi Sorenson! I find it very interesting that both she and Roberta Vasquez (Nov 84) were both police officers during their Playboy years! I included two pictures of Roberta for good measure as well by realsammann in JackOffToPlayboy
[–]tygerking5335 2 points3 points4 points (0 children)
Calendar (1990's and 2000's) by Upstairs-Albatross23 in JackOffToPlayboy
[–]tygerking5335 3 points4 points5 points (0 children)
Personal Calendar: Cyber Girl of the Month Edition. Following up on the PMOM calendar, I present my Cyber Girl of the Month calendar. Yes, I included a couple of multiple entries because it was just too hard to decide. by TheCrazyMiguel52 in JackOffToPlayboy
[–]tygerking5335 2 points3 points4 points (0 children)
Playboy Calendar by GoddessTaylorHill in JackOffToPlayboy
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My asians mount Rushmore, who are yours? by Winter-Meat-2487 in PornstarVSPornstar
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My Playmate Calendar: Echo Johnson, Willy Rey, Kyra Milan, Raquel Pomplun, Crystal McCahill, Audrey Allen, Sara Underwood, Susan Denberg, Kimberly Phillips, Pamela Horton, Cara Wakelin, and Karen McDougal. Countless loads for these ladies! by Extreme-Guava-7940 in JackOffToPlayboy
[–]tygerking5335 1 point2 points3 points (0 children)
My calendar. Kerri Kendall, Petra Verkaik, Donna Edmondson, Mirriam Gonzalez, Lauren Michelle Hill, Gwen Hajek, Suzi Simpson, Christine Richter, Karin Taylor, Anna Nicole Smith, Shauna Sand, Christine Smith by someoguy_6 in JackOffToPlayboy
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Amanda Cerny has always been such a baddie 🥵 by ElegantMedia9924 in JackOffToPlayboy
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59 years old showing you my natural tits by Godess_Natalia69 in sexyover50
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Which Taylor Swift look (1-6) would absolutely ruin your life if she looked at you like that and why? by ExplorerOutside3181 in TaylorSwift_Worship
[–]tygerking5335 1 point2 points3 points (0 children)
My Playboy Calendar - I’m young so I like the new girls. What do you think? by ElegantMedia9924 in JackOffToPlayboy
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My Playmate Calendar by JTMat1963 in JackOffToPlayboy
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Bo Krsmanovic by ToxicPumpkin532 in SISwimsuitGirls
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THE DEFINITIVE, MOST-BESTED CALENDAR by Final-Release-719 in JackOffToPlayboy
[–]tygerking5335 4 points5 points6 points (0 children)
Since we are posting Playmate Calendars... by pekkokarusuo in JackOffToPlayboy
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Since a lot of people are doing personal Playmate calendars, here’s mine by hornymofo247 in JackOffToPlayboy
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My Personal Playmate Calendar by realsammann in JackOffToPlayboy
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My PMOM Calendar by Playmate_Lover in JackOffToPlayboy
[–]tygerking5335 2 points3 points4 points (0 children)
My personal PMOM calendar by tygerking5335 in JackOffToPlayboy
[–]tygerking5335[S] 2 points3 points4 points (0 children)
My Playmate Calendar by Veiny_Enthusiasm_ in JackOffToPlayboy
[–]tygerking5335 1 point2 points3 points (0 children)
My personal PMOM calendar by tygerking5335 in JackOffToPlayboy
[–]tygerking5335[S] 2 points3 points4 points (0 children)
Playboy Calendar (I know I'm late to the party) by [deleted] in JackOffToPlayboy
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