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 to 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 from my relationships. I know hustling is ridiculously unglamorous and unsafe, and that there are some freaky guys out there. So 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 Green River Killer. What do I do? –Tempting Rent-a-Date Erotics
Best of Chicago voting is live now. Vote for your favorites »
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 your desires. 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 he knows you would find attractive. Then your FWB-pimp tells you what corner you need to stand on and 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, then run home to your pimp and hand the money over to him. Everybody wins.
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 that up until now I’ve read your advice just to laugh at the freaks, as I’d never encountered any kinks beyond the “normal” realm of sexual creativity. Now, however, my boyfriend has 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 stifle the 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. –Going Ga-Ga
But 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 longer 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.
People helping people–that’s what this column is all about. Of course, sometimes that means people helping people who fantasize about people being eaten by zombies, but what are you going to do? Thanks for sharing, Smitty and NECRO.
