I lost my virginity last night.

I'm a straight male in my early thirties, 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 Hooksexups.

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.

I feel like an asshole for even having these thoughts. Is there something wrong with me and/or am I an asshole?

— One Potential Asshole

P.S. I have attached some photos in hopes that you will respond.

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 ran into his room and proceeded 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 best to handle this situation. — Scared To Death

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 before her. Is she crazy? Or am I for doing it?— Not A Cream Pie Lover Yet

I'm a twenty-eight-year-old straight guy. I'm also five feet 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