reader, first-time mailer.
A long while ago, you wrote an incredible piece of general
advice for teenage boys. The advice was so excellent that
I clipped it out to keep in case I ever had a son. Well, years
later, I have a son. But I have since moved a gazillion times
and across several continents, 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 genetically- modified-wheat farmers,
and passing the afternoons on the porch sipping gin from a
teacup while terrorizing the local boys with a Super Soaker.
I digress: Any chance you could reprint your advice for teenage
boys? I know that I, my partner, and my son will all appreciate
Lady Lover And Mama
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.”)
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—just
chatting, not meeting up—with guys who found my online crossdressing
profiles. I know I could try to get a gal to use a strap-on
on me, but that doesn’t really appeal to me. I like flesh-and-blood
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 figure since I have no desire to date
men and can’t see myself with a guy long-term, I must be bi.
What are your thoughts?
If This Question Is A Little Scatterbrained
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.
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.
People, if you’re going to cheat on your partner, please use
protection. It’s quite literally the least you can do.
2. Fuck other people—lots of other people. But if you were
the one who dumped her, with cause, after she cheated, and
she wants to get back together, well, sometimes forgiving
someone for cheating is easier than getting over them. Only
you know if this is one of those times.
CONFIDENTIAL TO CALIFORNIA: Congratulations!
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