Get naked

Q I’m a 34-year-old female who has had a hard-to-impossible time going down on guys because of my gag reflex. I read your response to a girl a few months ago about taking it slowly, and I tried that with a guy I dated this summer. I got better and was really proud, as I experienced less and less urge to gag the more I got to know him—and when I got him off one time I was especially pleased. But recently I had a one-night stand with a guy and I vomited on him after he came in my mouth. It was very embarrassing and seemed to nullify all my efforts to get comfortable. Are there certain people who have a harder time when they swallow? Or could it be that I may be better at going down on a guy I’ve gotten to know? I just want to avoid having the throw-up thing occur again!

A Yes, it is likely that you would be better at giving a blow job to a guy you’ve gotten to know, because (a) you can get used to the length and girth of his dick and learn how far you can get it into your mouth without things getting messy; and (b) he’s going to know your limitations and therefore not thrust his dick into vomit territory. But the main thing to remember with any guy is that you don’t need to take the entire penis into your mouth to achieve the best blow job results. If I were you, I wouldn’t allow the dick to get anywhere near the gagging point. Just keep your hand on it during the deed so you can maintain some control over its trajectory. And lastly, there are tons of people who can’t stand the idea of swallowing come. If it grosses you out, don’t do it. You can allow a guy to come in your mouth and then just let it dribble out. No, it won’t be the most attractive thing in the world, but who’s going to complain—the guy you just sucked off? I don’t think so. Or at least, he better not.

Q About three years ago on a Friday night, I connected in a gay chatroom with a guy who wanted a first-time gay experience. I am 58 years old now. When this guy showed up at my door, it turned out he was very tall, muscular, good-looking and assured me he was 18 years old. He stayed until Monday morning. Turns out he was only 17 and this was in fact his very first sexual experience. He came again the next weekend, and for the past three years he’s spent the weekends with me. He wants to move in permanently and get married. I know he loves me and I love him. My question is, would I be doing him a huge disservice to make this arrangement permanent rather than allowing him the opportunity to go out and explore the world? I am the only person he has ever had sex with. I have met his parents and large noisy Italian family and they are in favor. Your objective insight would be appreciated.

A Although it’s sweet of you to be thinking so selflessly, you’d be crazy to push him to explore other relationships if he hasn’t been expressing a desire to do so. While having sex with just one person may seem like deprivation to you, he might be psyched about avoiding all the sturm und drang of trying to find a good partner. Having said that, I do think that you should be prepared to have this issue come up again when he’s a little older. Yes, it will suck to have invested, say, six years in a relationship only to have him finally realize that he should go off and play around a bit more, but remember, it’s better to have loved and lost than never to have tapped that hot piece of young ass.

Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com.