I was a promiscuous young man (read: straight college boy),
I had lots of casual sex. I particularly loved anal sex. And
I very particularly loved rough, unlubricated anal sex with
those wonderful women who enjoyed the same. I swore that I
would never be with a woman who didn’t love anal.
But I am now dating a woman whom I love intensely and who
is open to anal sex, but we just can’t make it happen. Toys,
fingering, eating ass, fucking—it all hurts her. She is a
ballerina and, therefore, small with a tight frame. I know
that you probably don’t have some super-secret gay-guy ass-sex
trick, but is there a best plan of action here? She wants
to do it, but obviously neither of us wants to see her hurt.
Please help. This is important to me.
Wants Anal Action
if they’re too big and ineptly employed, can hurt. Fingers,
with their bony knuckles and sharp nails, can hurt. Fucking
can hurt. But eating ass never hurt anyone. I mean, tongues
and sparkling-clean buttholes go together like rama-lama-lama-ke-ding-a-de-dinga-a-dong.
So unless you’re wearing a diamond-encrusted grill or you
studied eating ass under Jeffrey Dahmer, there are only three
plausible explanations for this baffling assertion, listed
here in ascending order of plausibility: 1. Your tongue is
four feet long and it irritates her esophagus when you rim
her. 2. She’s got a very serious medical condition—chronic
fissures? terminal hemorrhoids? suppurating gunshot wound?—that
she hasn’t told you about because she doesn’t want or need
your damn pity. 3. She doesn’t like anal and never will, but
she’s telling you what you want to hear.
But, hey, let’s take her at her word: She wants it. So what
can you do to make it happen? First, forget those women you
met at college who liked their anal rough and unlubricated.
(Where the fuck did you go to college? The University of North
Carolina at Bloody Stool?) Most people—sober people, male
and female people, people who want to live to get fucked another
day—require tons of foreplay and gallons of lube before buttfucking.
The foreplay can include rimming, fingers, vibrators, and
the slow, sensuous application of lube—lots and lots of lube.
Then, once everyone is nice and relaxed, you slowly penetrate
your partner, giving his or her anal sphincters plenty of
time to relax.
If you’ve been doing all this and it hasn’t worked, well,
then dating this dancer means going without anal.
My boyfriend and I have a problem with anal sex. We’re
gay, I’m a top, he’s a bottom. He says my dick is too thick
and that it makes him come too quickly. As soon as he comes
he tenses up and we have to stop. I’m a loving guy, and although
it sucks, I can deal with it—but what is causing it? Am I
doing something wrong?
your cock were “too thick,” BIG, your boyfriend wouldn’t be
able to come when it was in his ass. He’d just lie there shrieking,
“Get it out of me! Get it out of me!” That you can get it
in, and that you can fuck him until he comes, is proof that
you’re not too big or too thick. You’re just right.
The issue, it seems, is that your dick quickly pushes your
boyfriend over the edge; perhaps, thanks to your girth, your
dick slams his prostate in a way no other has. So what can
you do? The next time you fuck, stay inside him after he comes—with
his prior, written consent, of course—but cease all movement.
He should breathe deeply, riding out his orgasm, and allowing
his sphincters, which tensed up as he came, to begin to relax.
Once his orgasm subsides and his ass calms down, you should
be able to start fucking him again—but very slowly, just like
you would at the start.
I think my 13-year-old brother is gay.
I came home from school this past Christmas to visit my family.
One night I turned on my MacBook to check e-mail and there
was no battery left. I plugged it in and once it was on I
was shocked. There were pages of gay porn displayed on my
screen. Hoping it was some freakish virus, I downloaded HistoryHound
and sought out every webpage accessed on my computer. The
results showed other similar entries every time I came home
for a holiday.
Only one person might have gone down to the basement to use
my computer: my brother. I didn’t say anything to our parents,
and I didn’t talk to him about it either, because I didn’t
know what to say. If it were straight porn, I would probably
have just told him that he shouldn’t be looking at material
like that, and it would be done. But the deeper I looked,
the more disturbed I became. On the sites he accessed, I found
violent porn with themes of rape and domination.
I know this kid has a good heart and shows a lot of love to
everyone he knows, but how do I talk to him about this without
him feeling ashamed? Moreover, how do I address the violent
porn? And finally, what should I do as his brother?
Older Brother In Kansas
you’re young enough to remember what you were like at 13,
COBIK, halfway past puberty already, masturbating furiously,
and checking out online porn regularly. Your brother, like
many boys his age, is curious about everything that’s out
there, which could explain the more extreme stuff. Or maybe
your brother is gay and kinky, in which case you need to tell
him that he can ethically indulge his more extreme fantasies
with other consenting adults—when he’s an adult.
A few other things you can tell him: Eventually he’ll want
to come out to the whole family, but in the meantime he needs
to be more cautious about his computer usage. Any adult gay
men he meets online are not his “gay brothers,” but sexual
predators. And since most gay teenagers aren’t out, he won’t
get to date much in high school—particularly in Kansas—but
you can reassure him that he’ll make out like a bandit once
he gets to college.
Finally, COBIK, you ask what you can do as his brother. Gay
teenagers often get into trouble because they’re isolated—they
have no one to talk to, no one to confide in, no one to turn
to when they have romantic problems. Be his older, wiser,
supportive sibling, COBIK, the person he can turn to for advice.
What’s the biggest difference between a gay and a straight
Boy Wants To Know
only really significant difference, SBWTK, is the likelihood
of any given husband hearing these 11 magic words: “Honey,
it’s been way too long since we had a three-way.”
Some readers had issues with my advice last week for Unlucky
In Cuckoldry and Slaveboy’s Husband Has Hesitations. Read
their letters — and my responses — at www.thestranger.com/
new Savage Love podcast is available for download every Tuesday