The Playboy Advisor

The Playboy Advisor: Porn, Technology, and Fake Proposals

February 20

The Playboy Advisor: JB Smoove

February 13

Dear Playboy Advisor: Roleplay Alarm

January 30

Dear Playboy Advisor: Dry Wife, Dry Life

January 9

Dear Playboy Advisor: My Partner Is Terrible at Roleplay

December 19

Dear Playboy Advisor: I Love Small Dick Humiliation

December 12

Dear Playboy Advisor: My Friends Think My Kink Is Weird

December 5

Dear Playboy Advisor: My Girlfriend Wants Too Much Sex

November 28

Playboy Advisor: How to Give an Amazing Blowjob

November 21

Dear Playboy Advisor: I’m Too Ashamed of My Body to Have Sex

October 31

Dear Playboy Advisor: How Do I Bring Up Pegging?

October 24

The Playboy Advisor: Is the Missionary Position Boring?

September 26

Dear Playboy Advisor: Can I Keep My Exes’ Erotic Photos?

September 19

Dear Playboy Advisor: Is There a Cure for Premature Ejaculation?

September 12

Dear Playboy Advisor: How Do I Achieve My Dildo Dreams?

September 5

Dear Playboy Advisor: My Partner Makes More Money Than Me, and It Bothers Me

August 29

Dear Playboy Advisor: Can Weed Help Me Revive My Sex Life?

August 8

Dear Playboy Advisor: How Do I Unlock the Pleasure of the Prostate?

October 15

Dear Playboy Advisor: Is It Normal to Think About Sex 24/7?

April 22
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