Dear Sasha,

I'm a 50-year-old (male) virgin. I have identified since my early 30s as gay, but even as a gay male, I've never been in a serious intimate relationship, because I've never sufficiently worked through my fears about being sexually intimate with a woman. While I assume all (or almost all) gay men have no sexual interest in women, I do have the interest to explore, but have been too scared to do so all my life.

Dear Sasha,

I am a middle-aged, divorced environment writer with an affectionate eye on a much younger woman.

My friends consider me polite, outspokenly critical and a fit, reasonably good-looking man. My potential love interest, who is unattached, appreciates and even sought my mature attention to her singular life and talents as yoga teacher and videographer.

We met in a coffee shop, and superficially we have much in common. Acting, instinctively, I crave caring and sharing, and even intimacy, were her mood ever to become affirmative. I cannot yet intuit whether or not to pursue closeness with this tantalizing creature across a complex age gap.

Dear Sasha,

I was wondering if you have any information on sex dolls. I am a person with no time at all for a serious relationship. I want to know about the sensation. I mean, how different could it be? We're talking like, a $200 doll. I need to know if it's a good buy.

Mr. Need To Know

I'm going to suggest you visit jackinworld.com, which offers intriguing tips on a variety of masturbation techniques and has message boards where you can ask others about their experiences with sex dolls and/or genital stimulators/simulators.

Dear Sasha,

I was in a relationship with the first girl I slept with for years, so even though I've had a pretty active sex life, I never had to wear a condom.

Since being dumped, I've had close to no sex, and the only time I did, even though it was pretty fun for everyone (she was great, I was great, it was great), I realized how different, not as fulfilling, it is with a condom on. I felt little down there, felt disconnected and handicapped in my ability to provide pleasure, as I can now only feel what I'm doing well or not with/to her by sight and sound. I have this image of a massage therapist working with anesthetized hands.

Dear Sasha,

I'm a guy in his mid-20s who has never gotten laid, and never seriously pursued it either.

I had romantic notions about how it should go down -- and was a bit naive about my bi tendencies, which threw me -- and just kept putting it off. I wanted to "invest" in a real moment with someone special. That's still true, but I'm also eager to finally just get down with someone. After all this time, I think I'd be going in with a lot of expectations. Even if I just had a random fling, I'd risk walking away feeling stupid, having built it up for so long...or having given up on the idea that I deserved to be with someone I knew was really "invested" in me.

Dear Sasha,

I'm a male in his 40s who's told he's a good lover by his partners. I know I am, but there is one thing that I sorely lack in the female pleasuring department: I can't seem to make women squirt. I've tried numerous times, and the only thing I do is give them a burning and peeing sensation and myself a numb arm and wrist. I would like you to point me in the direction of books or videos that teach exactly how to do this properly. I sure don't want to learn it from a porn flick that doesn't show much anyway.

I Squirt You Not

Dear Sasha,

Supposing I were to call an escort and have her come down to my apartment for sex, my question for you is this: after giving her $100 to $300 of my hard-earned money, if that's what it costs, how on earth am I supposed to now achieve an erection?

And don't say she'll give me one. Now that my mind knows I've just lost all that money, it ain't happening. How do other men do this?

Cheap Sex Freak

Dear Sasha,

I recently invested in a toy (the Fun Factory Share) that I'm extremely pleased with except for one thing -- the head is really pronounced and quite a bit larger than the shaft.

Now, I personally quite like this for myself, but I bought it mainly for fucking a particular guy who, while well acquainted with his ass, is finding the head quite a challenge.

So what I'm wondering is this: is it possible to modify the head, pare it down maybe (yikes!), without ruining the toy? I'm loving the experience of having a cock that's actually connected to me, and we've had a lot of very hot play with it, but I really, really wanna fuck his ass.

AJ

Dear Sasha,

I was masturbating on the toilet the other day and, when I reached down to get some natural lubrication, I was a little shocked to find that I could feel my cervix was only about an inch or less away from the opening of my vagina.

Is this normal?

Do I have a short vagina? Am I not doing enough Kegels? I'm only 37, and I'm worried that I'll turn inside out before I'm 60.

Sara

Vaginas, vulvas, clitorises, uteri and cervixes come in all shapes and sizes. Kegels won't have any impact on the length of your vagina. They will simply help keep your pubococcygeus muscle strong.