Originally posted August 15, 2012.
I'm a twentysomething professional snowboarder. I have a problem that I don't really have anybody to talk to about. When I jerk it, I have to put a finger in my asshole to finish. Plain and simple, that's the only way I can come. I've tried to learn to come without the finger, but I can never reach climax. I can't even come in a girl's pussy without sneaking a finger in my back door. I go to great lengths to hide it—push her head in a pillow, etc.—because I don't want them to think I'm gay. (I have no problem with other people being gay, just FYI. It's just that you do not want snowboard groupies thinking you're gay. Girls talk, and then you never get laid again and all of your bros find out you're sticking things up your butt.) This letter is actually time sensitive. I'm pretty distraught that last night one of my regular chicks saw me do it. Today she won't return my texts. I want to convince her I was scratching an itch or something. I'm worried it might already be out there that I'm "gay." How do I learn to come without prostate stimulation?
Butt-Using Manly Man Entirely Distressed
I get a dozen letters a week from girls whose boyfriends "can't come." These girls tell me that their boyfriends get hard and stay hard and seem to enjoy fucking them—and fucking 'em and fucking 'em—but no matter how long their boyfriends fuck 'em, their boyfriends never climax. Invariably, these girls ask me if their boyfriends are gay. Because otherwise they would come during straight sex, right?
Your letter made me wonder how many of these girls are dating guys like you, BUMMED. That is, guys who need a poke in the prostate in order to come but either haven't figured that out yet or know it but don't wanna risk it in front of their girlfriends because their girlfriends might think they were gay if they did that. But their girlfriends think they're gay anyway—because they're not poking and not coming.
So it looks like you're damned if you do, BUMMED, and damned if you don't. Stick a finger in your butt and come, and your girlfriend—excuse me, your groupiefriend—might think you're "gay." Don't stick a finger in your butt and don't come, and your groupiefriend might think you're "gay."
A few practical suggestions...
Get a butt plug. It's a butt toy that your sphincter muscles hold in place—picture a small lava lamp that fits in your ass—and once you get it in, BUMMED, it won't slip out. Provided your groupiefriends aren't touching your asshole or looking directly at it, they won't even know it's there. And a butt plug might help you break the strong mental association you've made between finger-in-hole and climaxing. A few dozen look-ma-no-finger-in-hole orgasms, courtesy of a butt plug, might help you transition to look-ma-nothing-in-hole orgasms.
Get a girlfriend. I'm not a noted proponent of monogamous coupling—go ahead and google me—so please don't dismiss this as standard-issue advice-professional moralizing. But you might benefit from opening up to one person, someone you can trust with your secret—that will require an investment of time and emotional energy, however. But the payoff could be huge. Imagine having sex with someone you didn't have to hide from, BUMMED, someone who you didn't have to worry about judging you because she understood.
Get over yourself. You're a heterosexual guy who needs to be on the receiving end of a little heterosexual anal play during heterosexual sex in order to get off heterosexually. There are lots of straight guys like you out there. Your sexuality isn't the problem; your need for prostate stimulation isn't the problem. The problem is your shame and your desperation to hide this aspect of your sexuality from your groupies and bros. You may not be gay, BUMMED, but you do need to come out.