https://www.playboy.com/read/entertainment-culture/dear-playboy-advisor-my-friends-think-my-kink-is-weird/
Dec 5, 2024 - Kink is not the easiest thing to talk about with other people. Playboy Advisor columnist Cate Osborn shares some tips on the topic.
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https://www.playboy.com/read/entertainment-culture/the-playboy-advisor-porn-technology-and-fake-proposals/
Feb 20, 2025 - Editor’s note: These Playboy Advisor questions originally appeared in the spring 2019 issue of PLAYBOY Magazine. Q: How many women watch porn and...
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https://www.playboy.com/read/playboy-advisor-how-to-give-an-amazing-blowjob/
Nov 21, 2024 - Editor’s note: This question about blowjobs comes from the inbox of Cate Osborn, frequent Playboy contributor and Playboy Club creator. Q: I’m just...
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https://www.playboy.com/read/entertainment-culture/jb-smoove-playboy-advisor/
Feb 13, 2025 - "Def Comedy Jam" alum and "Curb Your Enthusiasm" star JB Smoove has an answer for everything in the latest Playboy Advisor.
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https://www.playboy.com/read/entertainment-culture/dear-playboy-advisor-roleplay-alarm/
Jan 30, 2025 - Editor’s note: This question about a discussing kink comes from the inbox of Cate Osborn, frequent Playboy contributor and Playboy Club creator. We...
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https://www.playboy.com/read/sex-relationships/playboy-advisor-prostate
Dec 13, 2024 - Curious and adventurous lovers ask The Playboy Advisor tips and tricks to unlocking the pleasures found in the prostate.
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https://www.playboy.com/read/entertainment-culture/the-playboy-advisor-dry-wife-dry-life/
Jan 27, 2025 - Editor’s note: This question about a discussing kink comes from the inbox of Cate Osborn, frequent Playboy contributor and Playboy Club creator. We...
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https://www.playboy.com/read/entertainment-culture/playboy-advisor-shan-boodram/
Aug 29, 2024 - Playboy Advisor Shan Boodram, clinical sexologist, YouTube star and author, offers advice to those who think about sex 24/7.
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https://www.playboy.com/read/entertainment-culture/dear-playboy-advisor-how-do-i-bring-up-pegging/
Oct 24, 2024 - In today's Dear Playboy Advisor, sex expert Cate Osborn digs into the question of how to bring up pegging with your signifiant other.
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https://www.playboy.com/read/entertainment-culture/dear-playboy-advisor-this-gift-exchange-got-weird-fast/
Jan 2, 2025 - Editor’s note: This question about a holiday gift turned awkward comes from the inbox of Cate Osborn, frequent Playboy contributor and Playboy Club...
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https://www.playboy.com/read/dear-playboy-advisor-my-girlfriend-wants-too-much-sex/
Nov 28, 2024 - Editor’s note: This question about a sexual appetite conundrum comes from the inbox of Cate Osborn, frequent Playboy contributor and Playboy Club...
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https://www.playboy.com/read/dear-playboy-advisor-how-do-i-talk-about-kink/
Mar 6, 2025 - Editor’s note: Maria Orrego is a Sex Therapist & Registered Psychotherapist. She is also the founder of Sex Off the Pedestal and co-host of the...
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https://www.playboy.com/read/entertainment-culture/dear-playboy-advisor-how-do-i-achieve-my-dildo-dreams/
Dec 13, 2024 - Q: I’m 27 years old, and I’m training my body for anal sex with a partner. I wanted to practice with dildos or butt plugs first so I could move at...
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