Q I lost my virginity last night. I'm a straight male in my early 30s, so it was about time. It wasn't awkward, and we had a good time. However, I didn't climax during sex, which is a result of years of death-grip masturbation. (Thanks for the warning, Dan, I'm sorry I didn't heed it.) She took it personally but seemed satisfied when I said it was only nerves.
I am left this morning with more confusion and trepidation about my relationship with my new girlfriend than I had going in. I suppose this is normal, but I don't see last night as some victory or a "bonding moment," and I am afraid that is a bad sign. I also find myself being extra critical of my partner's performance, which, as a virgin, I am not in a good position to judge. She has never been a particularly good kisser and her blowjob technique was less than spectacular. Although it was a pleasant experience, I feel like it lacked passion or a spark, which is probably just normal for a first time, but I am concerned.
Is there something wrong with me and/or am I an asshole? --One Potential Asshole
A There could be something wrong with you, OPA, and you could be an asshole. I can't rule either possibility out after quickly reading one email. It's possible that your girlfriend is a bad kisser/blower. Just because you're a virgin---or were a virgin---doesn't mean you're going to automatically click with the first woman who volunteered to put your dick in her mouth. It's possible that, however much you like this girl, you're just not sexually and/or chemically compatible. But sex is a skill that takes time and practice to acquire. It may take a little time and some experimentation for you to discover what works for you. And if you give her some time, you may find that she works for you.
If she didn't know you were a virgin, OPA, tell her. And tell her that it wasn't nerves that prevented you from getting off, but the unfamiliarity of the sensations you were experiencing and, perhaps, a masturbatory style that desensitized your dick. Tell her it might take you a little while to get there, but with her help and patience---and mouth and pussy---you're sure you can get there. And then try to relax, experiment and enjoy.
And no more death grip---period. When you masturbate, use your non-dominant hand, a lighter grip and perhaps a Fleshlight.
Q I'm herpes-free, but I found out today that my roommate has contracted it. He has a sore but won't see a doctor about it because he says he's embarrassed. We share the same bathroom, so I knew I would have to be diligent about that. But now I am freaking out: Not long after he shared this information, my seven-month-old puppy runs into his room and proceeds to cover my roommate's face in kisses. I've called the vet and my medical provider, and while they both agree that my pup cannot contract the STD, they cannot rule out the pup passing the infection on to me. Please advise. I would like to know how to best handle this situation. --Scared To Death
A Wouldn't it be great if being paranoid about contracting herpes was the only way to contract herpes?
Look, STD, lots of people self-diagnose themselves with herpes when all they have is an innocuous little cut or sore near their mouth or genitals. People who are too embarrassed/ridiculous to go see their doctors are highly likely to arrive at a herpes misdiagnosis. So calm the fuck down.
Even if your roommate does have herpes, STD, you're not going to get it from sharing a toilet. And you're not going to get it from your damn dog. For his own sake, your roommate shouldn't allow your dog to lick his open sores (who does he think he is? Job?), herpes-related or not, and if you're really freaking out about your promiscuously affectionate new dog, well, you can make up your mind to refrain from kissing any animal that drinks out of toilets, licks its own ass and laps up vomit.
Q I have a new girlfriend. She likes me to eat her cream pie after we have sex. She does get off again and squirts most of the time when I do it. No one has ever asked me to do this. Is she crazy? Am I? --Not A Cream Pie Lover Yet
A Why does someone have to be crazy? A cream pie isn't my preferred post-orgasm snack---I much prefer a Creamsicle---but if it turns your girlfriend on and gets her off, and if doing this for her doesn't leave you curled up on the bathroom floor in the fetal position, then you're not crazy and neither is she. She's kinky, you're GGG and you're both enjoying some kickass, boundary-pushing sex. Enjoy.
Q I'm a 28-year-old straight guy. I'm also five foot six and 124 pounds. I know, I know---I'm hardly microscopic. But I always feel like I'm a lost kid when I'm at a bar or club, with people my age or younger towering over me. So that, right away, is a confidence killer when trying to meet women. But here's the real kicker: I like tall women. In fact, I prefer somewhat butch women---Hilary Swank in Boys Don't Cry, Geena Davis in A League of Their Own---and this leads to the ancillary problem that many of the women I'm attracted to are lesbians and thus are not interested in me. But even the tall, butchy straight/bi girls tend to go for guys who are taller than them. Most women I talk to about why they fall for tall guys have a common theme: They are looking for someone who makes them feel secure.
That's what I want! Is it so damn wrong to want a woman to be protective of ME? I want to be held by a strong pair of lady arms! No, I'm not into super-muscle women, nor am I into hardcore dom/sub stuff. Why is my vanilla kink such an obstacle? What am I to do? --Below Their League
A Most women prefer taller men---not tall men, just men who are taller than they are. It's a sad, unavoidable fact, BTL, one you'll have to accept (just as I had to accept that most men prefer women), and you'll have to search longer and harder for the lady/lady arms of your dreams. Not much else you can do about it.
I've got some space to kill, so FYI: My recently announced celebrity crush---Stefon on SNL as portrayed by Bill Hader---is no longer operative. My new celebrity crush is Branden Hayward, the actor who plays the cute-but-dim young husband in those Rhapsody commercials. Sigh.