Q: I'm 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 worms.
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. —Have My Cake
A: You 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 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.
Q: I'm 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? —This Question Again
A: If 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 — or someone else's dick.
If you want that someone else (or someone else's dick) to be you (or yours), TQA, then don't be an impatient, insecure, macho drama queen about the way she's capable of having orgasms now.
Q: I 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? —Breasts On Other Babes
A: Stop 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.
Q: I 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 has 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 experience? —Teen With A Tech
A: Enjoy 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.
Q: I 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 hand job. He says he's never been able to come from blow jobs or hand jobs. 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? —Barely Licking Over Wide Junk Of Boyfriend
A: What's the opposite of macho drama? Vulvo drama?
Look, BLOWJOB, if you're both giving and receiving oral, and giving and receiving hand jobs, 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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