Q: I am a 15-year-old boy and I’ve never had a girlfriend and I wanted to ask you personally, how do you get girls? Like, the best way to get them, so they think I am interesting. I await your orders. —Teenager Going To Waste
A: There’s nothing I enjoy more than ordering around the odd teenage boy, TGTW, which I’ve been doing in this space since you were packin’ diapers. In fact, a couple of years back I issued some orders to a 15-year-old boy who asked pretty much the same question: How do I get girls? A lot of people wrote in to tell me they thought my response was terrific — that kid should be about 18 now, and if he was wise enough to take my advice he should be up to his eyebrows in pussy — so I’m going to give you the same advice I gave him. …
You’re having a hard time getting girls. That sucks. I remember what it was like when I was 15 and wanted boys and couldn’t get any. It sucked. But the sad fact is that most 15-year-old boys are repulsive — that is, most 15-year-old boys are awkward, half-formed works-in-progress. I certainly was. The fact that girls physically mature more quickly than boys makes it even harder, TGTW. Most girls your age already look like young women and they’re attracted to older boys — and there you are, aching for your first girlfriend, but still looking like a short, hairless chimp.
But don’t despair, TGTW. Your awkward/repulsive stage will pass. In the meantime here’s what you need to do: Worry less about getting your 15-year-old self laid and start thinking about getting your 18- or 20-year-old self laid. Join a gym and get yourself a body that girls will find irresistible; read so that you’ll have something to say to girls (the best way to make girls think you’re interesting is to actually be interesting); and get out of the house and do shit — political shit, sporty shit, arty shit — so that you’ll meet different kinds of girls in different kinds of settings and become comfortable talking with them.
Some more orders: Get a decent haircut and use deodorant and floss your teeth and take regular showers and wear clean clothes. Go online and read all about birth control and STDs, and learn enough about female anatomy that you’ll be able to find a clitoris in the dark. Masturbate in moderation — no more than 10 times a day — and vary your masturbatory routine. I can’t emphasize this last point enough. A vagina does not feel like a clenched fist, TGTW, nor does a mouth, an anus, tit fucking, dry humping or e-stim. If you don’t want to be sending me another pathetic letter in five years complaining about your inability to come unless you’re beating your own meat, TGTW, you will vary your routine now so that you’ll be able to respond to different kinds of sexual stimulation once you do start getting the girls. Good luck, kiddo.
Q: I’m an 18-year-old girl whose 19-year-old boyfriend gets off on domination. One night we told his best friend and then I had two hot studs kissing my feet, wearing my panties and getting spanked. It was rad! The best part of all is that we don’t have a question for you. No one weirded out! And we owe it to you! Reading your column we learned not to fear our crazy desires and to talk things over before, during and after. I didn’t want to have intercourse with or in front of my boyfriend’s friend, and I said so before we got started. My boyfriend didn’t want me to make him and his friend kiss, and he said so. Everyone had fun, no one got more than they bargained for, and we all had a blast! We’re going to do it again! We just wanted to say thanks! —Grateful Goddess Girl
A: Thanks for the mad props, GGG, as you kids like to say.
Q: I met this guy on a gay chat line. I’m 21, he’s 42, a big, hairy daddy type. I’ve had a daddy fetish forever but never acted on it. He’s sweet on the phone, and we have explosive phone sex. My friends would be weirded out by this. Should I meet him? Can affairs with such a large age gap work out? —Desires Affectionate Daddy
A: It depends on how you define “work out,” DAD. If by “work out” you mean, “We will fall hopelessly in love and be together forever,” then the answer is no, it’s unlikely to “work out.” But if by “work out” you mean, “I’ll meet a good guy, have some great sex, and even if we don’t wind up together I’ll do my best to make sure we wind up friends,” then the answer is yes, it could work out.
As for your friends, I don’t see how their feelings factor in — not unless you’re planning to ask them to watch.
Q: I’m 19 and closeted. I’ve been chatting with a guy on the Internet for six months and now he wants to meet. I’m convinced that he’s too good for me. Aside from looks, he’s out and older and I don’t know why he’d want to be with someone like me. My other online friends — they’re the only people I’m out to — think we should meet. I’m effing scared. I’m not going to ask you to compare our pics, but is there a concrete checklist to verify if someone is out of your league? —Insecure In Internetland
A: The good news: If you meet this boy and he’s into you, III, then you’re in his league. That’s because each and every one of us gets to decide who plays in our own personal league. If he invites you to play, you’re in.
Now the bad news: There’s lots of scum floating around on the Internet — this applies to you too, DAD — and you have to be careful. While this may simply be a case of your own insecurities preventing you from recognizing whatever it is about you that this other guy finds attractive, something more sinister could be going on. You say you don’t know why someone better looking, older and more experienced would want to meet you. Unfortunately in some cases it’s because younger, closeted and insecure guys are easier to manipulate. So this guy is either honestly into you or he’s an asshole looking to take advantage of your youth and inexperience. If you decide to meet him, III, meet in a public place, tell someone where you’re going and watch out for red flags. Does he pressure you? Does he try to get you to do things, sexual or otherwise, that make you uncomfortable? If so, run like effing hell.
Q: Two guys or two girls or a combo kneel on either side of a guy with an erect penis. The standing guy then thrusts his penis back and forth between their two sets of lips until he pops. What the hell is that called? Do you know? Does anyone know? It needs a name! —Nasty And Memorable Evening
A: Hmm … so far as I know the sex act you describe lacks a name. Any ideas, dear readers? My suggestion box is open.Send letters to firstname.lastname@example.org