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How to get your street hustle on



Q: I’m a 20-year-old bi guy with a girlfriend of seven months and a few male friends-with-benefits (FWBs). I’m happy, but I have a kink and I’m wondering how I could safely explore it. I want to try hustling. A random guy picking me up on the street and paying me for sex is an elusive turn-on, one that I can’t derive in my relationships. I know hustling is ridiculously unsafe, unglamorous and there are freaky guys out there. How can I do this safely? I don’t want to get every STD in the book or end up the victim of some gay Gary Ridgway spin-off. What do I do? —Tempting Rent-A-Date Erotics

A: This advice I’m about to give you is inoperative, TRADE, if your girlfriend doesn’t know what’s going down. (That would be you.) If you’re honest with her about your sexuality and the benefits your friends are currently enjoying, and if you’re taking all reasonable precautions to protect her emotional and physical safety, then I’m happy to help you realize this fantasy. If you’re not being honest with her, kiddo, God will punish you in this life and the next.

Now honesty is hard, I realize, particularly for some bi guys. But the only way to safely realize this fantasy, TRADE, is by sharing it with your most adventurous FWB and enlisting his help. After you tell all, ask your FWB if he would be willing to facilitate the realization of this sexual fantasy. In other words, ask him to pimp your ass out. It would be his job to find and recruit a guy you don’t know, a guy who’s trustworthy and safe but just a little freaky, a guy that he knows you would find attractive. Then your FWB/pimp tells you what corner you need to stand on what night and you wait there until your prescreened, preselected john drives up and rolls down his window. Be his ho, be safe (the real pros all use condoms), get paid, and run home to your pimp and hand the money over to him. Everybody wins.


Q: So, Dan, I read
your column, buy your books, enjoy your op-eds in The New York Times, respect what you do. But I must say, up until now I’ve read your advice to laugh at the freaks, as I had never encountered any kink beyond the “normal” realm of sexual creativity. But my boyfriend just suggested, in the kindest way, that he wants me to wear diapers for him. Diapers, Dan. Diapers. I want to be a GGG gal but realistically, how do I suck up my inner monologue that says this is absolutely ridiculous? And how can I continue to respect my statuesque boyfriend, especially without psychoanalyzing his need to baby me like this? He says he doesn’t want me to, you know, “go boom-boom” in them. I think it’s pre-sex wear, like thongs and garters, only more absorbent. —Going Ga-Ga

A: Most people with a diaper fetish want to wear them, GGG, not put them on another person. That makes your boyfriend a freak among freaks. I’ve always regarded diapers as a “fetish too far,” meaning a kink that even the most GGG partner has a right to balk at. But seeing as how you’re already emotionally invested in this guy, and seeing as how your boyfriend is statuesque, and seeing as how no “boom-boom” is involved … you might want to go there with him, GGG. Who knows? If you can suppress the giggles long enough to get through one or two diaper sessions, maybe — just maybe — you’ll find that you enjoy that baggy-assed feeling more than you thought you would. Or, more likely, you will take enough delight in his enjoyment of it to make it bearable, and eventually you will achieve a Zen indifference to his kink, neither repulsed nor turned on, but willing to indulge him.


Q: I’m an 18-year-old male in my first serious relationship. Recently I convinced my girlfriend to start giving me hand jobs. They’re great. Now for the bad news: When I was going through the worst of puberty, I had no access to information about masturbation. Needless to say, for the past five years I’ve been doing it too hard, too much. The other night, my girlfriend was going at it for a good 20 minutes and I never came. Needless to say, I was so embarrassed I wanted to die. I have read in your column to vary routines and styles when masturbating, and since reading that, I have. But I may have started too late. My question is if there is any way to work back to the sensitivity I once enjoyed? I’ve cut down masturbation to once a week, and I’m varying my routine when I do masturbate. Apart from those steps, is there anything else I can do? Or will those steps even work at all? Am I just shit out of luck? —Long Time Coming

A: The steps you’re taking will help, LTC, but only if you’re ruthless. Keep using that lighter touch and vary those routines, but if you don’t come during your retooled jack-off sessions, grasshopper, then you don’t get to come. The worst thing you could do is start out using that lighter touch and then, when it’s not working and you’re desperate to come, revert to the ol’ death grip. Here’s the message you have to get across to your dick: You can learn to come from subtler sensations or you’re not going to come at all.

And while I want you to be hard on your dick, LTC, I don’t want you to be hard on yourself. Sometimes it takes a while to come, and taking more time is preferable to coming too quickly. What’s more, some men, like some women, simply require focused, intense (a light touch can be intense), prolonged stimulation in order to come. You may be one of those guys.


Q: Love the column, just wanted to pass along this link to CORPSE and any other zombie fetishists out there: It’s a spoof on the movie Re-Animator as zombie porn. Zombie-porn fetishists will be thrilled. —Smitty

Q: CORPSE may be interested in The Stink of Flesh (Scott Phillips, 2004) — “How can you lead an alternative lifestyle when everybody is dead?” — a movie that has zombie sex (rape, actually), complete with bloody zombie revenge for said rape. Not to be missed if one has zombie-related sexual fantasies. Definitely to be missed if one does not. —Nuts-Eating Cadavers Regurgitate Often

A: People helping people — that’s what this column is all about. Of course, sometimes that means people are helping people who fantasize about people being eaten by zombies, but what are you going do? Thanks for sharing, Smitty and NECRO.


Q: When are you gonna put in your advice for 15-year-old girls? I’ve had a huge crush on this guy for six months! But I can’t tell if he likes me at all! I’m 15 and have no experience with this stuff! I really need advice! Please save me from the hell that is crushdom! —Have Crush, Will Suffer

A: Oh my God! I totally spaced that column! Again! Last week it was the pope! This week it was the pot! I promise that next week’s column will be packed with advice for 15-year-old girls! But I don’t think you’ll like some of it! Heart ya mass!

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