Q: Along while ago, you wrote an incredible piece of general advice for teenage boys. The advice was so excellent that I clipped it in case I ever had a son. Well, years later, I have a son. But I have moved a gazillion times, and I no longer have that precious piece of paper. My son is only 9 months old, but I am worried that by the time he is a teenager, you will have retired to some fancy ranch where you will spend your days raising organic cattle, being nasty to the local farmers and passing the afternoons on the porch terrorizing the local boys with a Super Soaker. Any chance you could reprint your advice for teenage boys? I know that I, my partner, and my son will all appreciate it.
GGG Lady Lover And Mama
A: Congrats on the birth of your son, GGGLLAM, and here, at your request, is my advice for the hard-up teenage boy:
You’re having a hard time getting girls. That sucks. I remember what it was like when I was a young teenager and wanted boys and couldn’t get any. It sucked. But the sad fact is that most young teenage boys are repulsive—that is, they are half-formed works in progress. Girls mature physically more quickly than boys, which means most girls your age already look like young women and they’re generally attracted to (slightly) older boys—and there you are, aching for your first girlfriend, but still looking like a short, hairless chimp.
But don’t despair, HUTB. Your awkward/repulsive stage will pass. In the meantime, here’s what you need to do: Worry less about getting your young teenage 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—read books—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 about birth control and STIs, 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, HUTB, nor does a mouth, an anus, titty 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, HUTB, 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.
(The above advice was for a straight teenage boy. Gay teenage boys should read “boys” where I said “girls,” “anus” where I said “vagina,” “prostate” where I said “clitoris,” and “fist” where I said “fist.”)
Q: I am a 27-year-old male, identify as bisexual, and enjoy crossdressing—although I have only crossdressed with guys I meet online. I have no real desire to meet guys unless I’m dressed up. And when I do get together with a guy, once I cum, I’m ready to leave. I can’t see myself in a relationship with a guy. With females, I can see myself getting married and having kids, etc., and when I have sex with a woman, I’m not in a cum-and-go mentality. But when I’m dating a girl, after about a month, I start to float back to jerking off while chatting with guys who found my online crossdressing profiles. I know I could try to get a gal to use a strap-on, but I like flesh-and-blood cock. So I guess my question is this: Do I hold out for a gal who is open to me having the odd bisexual encounter or do I learn to use my imagination a bit more during strap-on play? I only fantasize about cock when I’m already horny, and I lose all interest in it once I’ve cum. I thought in the past that I might be gay, but I have no desire to date men and can’t see myself with a guy long-term.
Sorry If This Question Is A Little Scatterbrained
A: First, SITQIALS, I’m sorry if my response is a little scatterbrained. I’m on vacation and currently in something of an impaired-state holding pattern over the Pacific Ocean. I didn’t read all of today’s Savage Love mail—yours was the first letter I pulled from the stack—because the shit that’s impairing me is forcing me to take it easy. How easy am I taking it? So easy that I’m not going to change “cum” to “come” in your letter.
Anyway, yeah, it sure sounds like you’re into women, SITQIALS, even your fetish screams “into chicks.” Your crossdressing and role-playing fantasies are all about your bone for women and feminity. You dig women so much, you want to play the role of the woman—you want to look like a woman, be treated like a woman, get fucked like a woman. But in your fantasy scenarios, SITQIALS, men aren’t human beings and sex partners, men aren’t people with whom you could potentially have relationships, they’re props, the finishing touch that completes your ensemble.
And once you blow your load, once the game is over (once you COME), you’re done, you don’t need that prop anymore, and you just want to scram.
So what do you do? Well, I think your fetish makes you pretty damn near incapable of monogamy, and you’ve already discovered that strap-ons don’t meet your particular needs. So, yeah, I think you should hold out for a woman who’s into your fetish and turned on by the idea of sharing your ass—when it’s wearing panties—with a few good men. It’ll mean a longer search for the right woman, which you should be willing to do, because you’re worth it.
You might want to Google “autogynephilia.” Not saying that’s where you’re at or headed, don’t know enough about it to endorse it, but … it seemed relevant, food for thought, the more you know, etc.
Q: I have two things to ask/say: 1. Could you remind people that if they’re going to cheat on their partner, to use protection? 2. Could you give me advice on getting over my ex-girlfriend? She ended things pretty terribly (see question 1), yet I’m still having a hard time letting go.