Losing my V-card

How do I reveal my inexperience without scaring off a potential partner?

I’m a 23-year-old gay guy. I’ve been talking to a nice guy who will possibly become my first boyfriend. The little quibble I’m having is … I’m a virgin. It’s not that big a deal to me — it just hasn’t happened yet — but I was wondering if I should mention it to this guy. He made an aside about virginity (unprompted by me) during one of our chats: “No, I’m not a virgin, that’s nothing that you should worry about with me.” That was probably my opportunity to tell him, but I didn’t. Should I have told him? What if I tell him during sex? Could that make it hot?

Thank you for what you do. I found the courage to come out because of you.

Ready And Willing

If you found the courage to come out to family and friends about being gay — which you found inside yourself, RAW, but thanks for the nice compliment — you can come out to this boy about being a virgin.

Don’t tell him during sex, RAW, and don’t tell him in a way that makes this relevant information about your sexual history — you don’t have one — seem like a character flaw, a cancer diagnosis, or a request for an open marriage six years after you began an adulterous affair with a congressional staffer. You’re just a 23-year-old virgin, RAW, there’s nothing wrong with you; it’s not like you’re one of Elizabeth Santorum’s idiotic gay friends or a cast member of The A-List: Dallas. The next time you see this boy, initiate a casual, low-stakes, getting-to-know-you make-out session at a time when you can’t transition to full-on, no-holes-barred gay sex. Relax, kiss the boy, be chill. Then pause and inform him that you’re not very sexually experienced. Reassure him that you’re not a duckling — you’re not going to imprint on the first dick you see — but that you wanted him to know.

Have boyfriend. Several months. Love sex. First time we sixty-nine, I notice he has a little turtlehead sticking out. You get me? Second time, he has bits of toilet paper stuck in that area. CAN I ADDRESS THIS? And how do I do it without giving him a permanently flaccid penis? I love this man to pieces and know this is a humiliating topic. Please help!

Mired In The Mud

Got you. Wish didn’t. But did.

If you don’t have the nerve to speak up when someone is grinding shitbuds and dingleberries in the vicinity of your nostrils, MITM, I’m not sure there’s anything I can say that’s gonna help. But for what it’s worth…


When someone pushes your face into a dirty asscrack — or allows you to place your face in the general vicinity of a dirty asscrack — you say something along the lines of “What the fuck, dude, go take a dump and jump in the shower! Christ!” His ego, to say nothing of his future erections, should be your least concern at a moment like that. So you say it without hesitation, without concern for his feelings, and you say it as you leap out of bed and reach for your shirt, pants, car keys and phone. You don’t just lie there pretending that his buttrasta isn’t dangling over your nose. Even if he’s never able to get another erection with you, MITM, he’ll know to spot-check for cleanliness — are there no washcloths in Gilead? — before he crawls on top of anyone else.

How are you supposed to react to the discovery — entirely accidental — that your youngest brother has a “femdom” relationship with his wife? I stumbled over my brother’s “anonymous” sex blog. It goes into detail about the “domestic discipline” she subjects him to: humiliation, spanking, “ruined orgasms” (whatever that is!), cuckolding. There are no names, but there are pictures. Their faces are blurred out, but I recognize their living room, their bedroom, my brother’s chin and hair. If I recognized them, other family members might. What do I say?

Biggest Big Bro

Besides “Hey, bro, I’m kinky, too!”? (You “stumbled over” your brother’s kinky sex blog? How’d that happen? Did he leave it sitting in your driveway?) If you can’t bring yourself to say that, BBB, you say nothing and trust that more-distant, less-kinky family members are unlikely to “stumble over” your brother’s anonymous femdom blog anytime soon. And even if they do, they’re probably not familiar enough with your brother and sister-in-law’s home, jewelry, chins, etc., to recognize him.

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