CategoryAdvice

Thief of Hearts 

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Dear Walter, I am a 25-year-old lesbian who desperately needs your help. I just broke up with my girlfriend. She has been mad disrespectful lately. I broke up with her because I got sick and tired of the way she’s been treating me. And she had the nerve to cheat on me. It was then I decided, enough was enough.  A week later, my place was robbed. They stole my TV, phone, and clothes. I have a...

What It’s Really Like to Have a Threesome

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Dear Walter,  I’m a thirty-something gay man living in New York City. Lately, I have been experimenting with my sexuality. I never had a threesome but I really want to try it. What advice would you give me on having my first threesome? —Thirsty for a Threesome Dear Thirsty for a Threesome, Threesomes are awkward. Imagine being bent over while hungover with all openings stuffed like a turkey well...

The Darkest Blues Are Black

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Dear Walter: I’m new to the online gay dating scene and I’m wondering if you ever encountered a dangerous situation with an app?  I want to meet guys but I’ve heard horror stories online about guys getting raped, robbed, and even murdered.  So my question is have you ever met someone online and something bad happened? And how did you handle it? -Reluctant Online Dater Dear Reluctant Online Dater:...

What Happens When You Pay To Play, and He Doesn’t Show Up?

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Dear Walter,  What do you do when you send money for a guy to come to you? He gets the money but doesn’t show up? -Love Letdown Love Letdown, There is nothing worse than not getting what you paid for. Sounds like you have been set up. And judging from your question it sounds like a late night situation where money was used as the catalyst to get him to come to you — so you’ll cum later. We live...

How to Clean Your Ass Before Anal Sex

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Anal sex is an essential component in for the homosexual experience.  To avoid a shitty situation you need to learn how to clean back there before sex. There is nothing worse than shitting on 600-thread count Egyptian cotton sheet. I wrote about the dark side to douching in, To Douche, Or Not To Douche, That Is The Question. Thankfully, there is an illustrated guide written and designed...

Make Him Feel Like A Man Again

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Artwork by Anthony Gonzales  Dear Walter:  How can I make my boyfriend top? Please give me some advice? Helppppp!!!! Dear Hopeless Romantic, The last time I encountered a situation, when my boyfriend was really a bottom, masquerading as versatile. He had no idea how to use anything else but his mouth. I tried to train his penis, poor thing didn’t even know how to put a condom...

How Do You Know When Enough Is Enough?

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Dear Walter, I’m writing to ask when is enough [is] enough? I’ve been in a relationship with one person over 4 years and it seems to me instead of getting better it is the opposite. I’ve exhausted all think[ing] and compromising to save what we do have, which to me seems to only be the sexual part. I’ve asked for a professional opinion of the situation, but that...

Does It Matter That I Am Attracted to Black Guys?

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I Think My Boyfriend Has a Drinking Problem

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Friday night tested our relationship. Trust issues coupled with his binge drinking drained me. We agreed earlier that day to meet at a New York nightclub called Secrets at 11pm.  Photo by Max De Silver Day four of no phone and limited funds fucked up my week. I arrived at the club just before 2am. I rushed in looking for my man, hoping he would be forgiving, and not willing to cause a...

My Boyfriend Is Too Tired for Sex

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Dear Walter:  Is my boyfriend cheating if he’s a male prostitute? We have been dating for three months. He claims he’s only having sex with clients. He says that he doesn’t want to have sex with me because he’s too tired or has to work. He doesn’t want to treat me like a client.  -Dating A Prostitute Dear Dating a Prostitute: Your poor boyfriend engaging in the world’s...

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