a 21-year-old woman with bi-curious tendencies who’s been
in a committed relationship for four years. He’s sweet and
kind. We share a lot of interests and get along very well.
Thing is, I don’t know if I’m meant to be in a committed relationship.
For the past year and a half, I’ve been thinking about what
things would be like with another man. I also frequently imagine
what it might be like to sleep with another girl. In fact,
whenever I’m masturbating, I get more excited by lesbian scenarios
than straight scenarios—although I’ve never been able to come.
I’ve never experienced an orgasm. But that’s another can of
The main problem is this: I find myself steadily losing interest
in my current partner. I find myself fantasizing about having
sex with other men and other women. I’m open to the possibility
of a threesome, but my boyfriend isn’t. He’s completely against
the idea. From the start, I’ve never hidden the fact that
I’ve never reached orgasm, and he’s never created any macho
drama about that.
I’ve slowly come to the realization that I’m no longer sexually
attracted to my boyfriend. I don’t have the motivation to
improve our sex life anymore. I just go through the motions.
At the same time, my boyfriend remains my best friend and
I’m not willing to give up my best friend over sex. I want
to keep him in my life, as he is my most important source
of emotional support.
If you, as an “impartial” observer, could help me out, I’d
really appreciate it.
can have your current boyfriend, HMC, at the price of a lousy
and uninspired sex life with a guy who doesn’t give a shit
about your pleasure—excuse me, a partner who hasn’t created
a lot of “macho drama” about the fact that you’ve never had
an orgasm and isn’t interested in helping you realize your
fantasies—or you can find a new boyfriend and/or girlfriend
and perhaps discover that orgasms are easier to come by when
you’re with someone who (1) turns you on and (2) gives a shit
about your pleasure and (3) hasn’t come to symbolize the death
of sexual possibility.
Giving up the current boyfriend means you’ll have to find
a new emotional tampon—excuse me, a new “source of emotional
support”—but that’s a price that you should be willing to
pay, HMC, particularly at your age.
And if you don’t want to find yourself boyfriendless and bestfriendless
ever again, HMC, in the future keep those roles separate.
a 26-year-old heterosexual male in a relationship with a 25-year-old
female. I’m her first boyfriend. She’s never had an orgasm
that wasn’t self-induced. I’ve asked her multiple times what
I can do to try to get her off, but she doesn’t really have
anything to tell me. There’s a lot of trial and error going
on. I feel like I’m kind of flying blind. Help please?
she can get herself off, TQA, then she should be able to get
herself off while you assist. Let her get herself off while
you watch, while you hold her, while you suck on her tits,
while she sits on your face. Gradually work your way up to
her getting herself off while you’re inside her.
Don’t make the “macho drama” mistake of viewing the orgasms
she self-induces while you’re there as somehow deficient or
dysfunctional. The more you can relax and enjoy the orgasms
she’s self-inducing now—the more you can both relax
and enjoy them—the sooner she’ll be able to relax, enjoy,
and, perhaps, transition to orgasms induced by someone else/someone
If you want that someone else/someone else’s dick to you be
you/yours, TQA, then don’t be an impatient, insecure, macho
drama queen about the way she’s capable of having orgasms
am a woman who is with the love of her life. I enjoy sex immensely
but have begun to fake orgasms because it hurts him that he
is not making me come. I believe the obstruction is psychological.
I am self-conscious about my body and can only come using
a vibrator while looking at pictures of women with nice boobs.
I fantasize that I am both the woman in possession of these
assets and the person lusting after her. I am certain of my
sexual orientation: I did quite a bit of experimenting with
beautiful women, but they did nothing for me. Any insights?
On Other Babes
faking, BOOB, and start incorporating your vibrator and
your fantasies into the sex you’re having with the boyfriend.
Your boyfriend needs to talk a boob-esteem-building blue streak
while you fuck—he needs to tell you how hot your breasts are,
how much they turn him on—and you need to use your vibrator
on yourself and fantasize aloud about the assets you’ve got
and the assets you lust after while you two are fucking.
You know what works for you, BOOB, you just have to risk sharing
it with the love of your life.
am an 18-year-old straight girl. I am also a virgin. After
my 18th birthday, I bought a small vibrator. I love it—it’s
completely changed masturbation and I reached orgasm for the
first time. However, I’m worried about developing a dependence
on it. Should I hold off on using it until I get some real
With A Tech
your vibrator, TWAT, and enjoy those orgasms—but mix it up.
Masturbate with your vibrator and without; see how worked
up you can get through fantasy alone; get yourself close to
the edge and finish yourself off with your hand; experiment
with nonvibrating, inanimate sex toys. And when you start
having sexual experiences with nonvibrating, animate sex toys
(boys), don’t be shy about introducing them—or their genitals—to
your vibrator. Dicks are just big clits, TWAT, and vibrators
can work wonders on dicks, too.
am in college and in a super-fantastic relationship. We have
fun together and we have great sex. However, he doesn’t orgasm
when I blow him or give him a handjob. He says he’s never
been able to come from blowjobs or handjobs. I don’t mind
going straight to vaginal intercourse after blowing him for
a bit, although I sometimes encourage him to finish himself
off and ejaculate in my mouth. It’s not like I’m offended;
I’d just like to get him there.
I have a tiny mouth and tiny hands—could that be the problem?
He says it doesn’t have anything to do with me. He just plateaus.
How do I solve this problem, Dan? Is our sex life condemned
to, God forbid, just vaginal intercourse?
Licking Over Wide Junk Of Boyfriend
the opposite of macho drama? Vulvo drama?
Look, BLOWJOB, if you’re both giving and receiving oral, and
giving and receiving handjobs, then you haven’t been “condemned”
to “just” vaginal intercourse. You’re having all kinds of
sex—it’s just that he requires something very specific in
order to get off. If there are times when you want to mess
around without being fucked, or times when you’re not up for
vaginal intercourse, just get him as close as you can and
let him finish himself off with his hand.
Your boyfriend is orgasmic, BLOWJOB—There’s no problem
here to solve.
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