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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, 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.

 I'm open to the possibility of a threesome, but my boyfriend isn't. I've never hidden the fact that I've never reached orgasm, and he's never created any macho drama about that. But 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 want to keep him in my life, as he is my most important source of emotional support.

Have My Cake

 

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 and/or girlfriend and perhaps discover that orgasms are easier to come by when you're with someone who: (1) turns you on; (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, particularly at your age. And if you don't want to find yourself boyfriendless and best-friendless ever again, in the future keep those roles separate.

 

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. 

This Question Again

 

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 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 as somehow deficient. The more you can both relax and enjoy the orgasms she's self-inducing, the sooner she'll be able to transition to orgasms induced by someone else/someone else's dick.

 

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 possessing 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

 

Stop faking, BOOB, and start incorporating your vibrator and your fantasies into the sex you're having. Your boyfriend needs to talk a boob-esteem-building blue streak while you fuck -- he needs to tell you how hot your breasts are -- 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. You just have to risk sharing it with the love of your life.

 

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'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 experience?

Teen With A Tech

 

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 to your vibrator. Dicks are just big clits, TWAT, and vibrators can work wonders on dicks, too.

 

I am in college and in a super-fantastic relationship. 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. 

I have a tiny mouth and tiny hands -- could that be the problem? HOW DO I SOLVE THIS PROBLEM? Is our sex life condemned to just vaginal intercourse?

Barely Licking Over Wide Junk Of Boyfriend

 

What's the opposite of macho drama? Vulvo drama?

Look, BLOWJOB, if you're 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 to get off. If there are 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 TO SOLVE.

 

Find the Savage Lovecast (my weekly podcast) every Tuesday at thestranger.com/savage.

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