I am a gay man, and there is a guy I have slept with a few times, but I am not seeing him seriously (nor am I seeing anyone else). I top. I find him very attractive, and we have very good chemistry. The first time we were together, I was about to use a condom, and he asked me to just play around his anus with my penis before I put on the condom, and before you know it, we were having unprotected sex. The next time, I insisted on a condom; he agreed, but then, as I tried to penetrate, he said he had difficulty taking someone my size with a condom on. We made a few more bumbling attempts with the condom, and I lost my erection. I finally said "fuck it," and fucked him without a condom. The next time, I bought ultra thin condoms, but, in the heat of the moment, we did it without one. I was tested twice since I slept with him. Both tests covered the periods since I'd last slept with him, and I was negative. We're about to see each other again after over two months apart. (I have not been with anyone else in that time.) I'd rather not deal with the comedy of errors of the condom again. I'm wondering whether I'm playing with fire by going without.

Risky Business

My response after the jump...

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You are playing with fire—or gambling with your health. Not your life, not anymore (not in the West), but definitely with your health. Contracting HIV may not be a death sentence anymore, RB, but it's still a major life complicator. That said, it's much harder for HIV to pass from the bottom to the top during anal sex. It can happen, but the chances of it happening are much, much lower. Still, RB, there is risk.

But looking on the bright side: If this guy is poz and he's being treated and he's taking his meds correctly and his viral load is undetectable, he's not going to infect you with HIV. (Peter Staley: "Undetectable = Uninfectious.") Another bright side: You're a perfect candidate for PrEP:

Pre-exposure prophylaxis, or PrEP, is a way for people who do not have HIV but who are at substantial risk of getting it to prevent HIV infection by taking a pill every day. The pill (brand name Truvada) contains two medicines (tenofovir and emtricitabine) that are used in combination with other medicines to treat HIV. When someone is exposed to HIV through sex or injection drug use, these medicines can work to keep the virus from establishing a permanent infection. When taken consistently, PrEP has been shown to reduce the risk of HIV infection in people who are at high risk by up to 92%. PrEP is much less effective if it is not taken consistently.

If you have a hard time using condoms correctly and consistently during anal intercourse, RB, you absolutely, positively need to get on PrEP. Like Mark Joseph Stern said at Slate:

Those who slam Truvada tend, in the same breath, to praise condoms like it’s 1986. But condoms—despite being a favored solution of the gay old guard—present serious problems of their own. Only 1 in 6 gay men use condoms unfailingly, and sporadic use provides minimal defense against HIV infection. Even more troublingly, condoms don’t work as well during anal sex: With perfect use, they’re only 86 percent effective against HIV during anal intercourse. (With perfect use during vaginal intercourse, they’re 98 percent effective.) Add to this the fact that unprotected bareback sex just feels better, and you’ve got a strong case for combining Truvada with condom usage as an extra protection against infection...

Gay men in the 1980s fought for their lives to get the government to expand access to and education about condoms. It was a noble struggle, but also an insufficient one. Today’s AIDS landscape reveals that an unyielding devotion to condom usage isn’t enough to halt the spread of HIV. It takes a variety of safe-sex practices to shield gay men from infection, and Truvada should be a linchpin of that strategy. Given the seemingly unstoppable drop in condom usage among gay men, this is no time for ideological disputes or intergenerational conflict. Every gay man with multiple sex partners should take Truvada, and AIDS activists should do everything they can to get the drug in the hands of those who want it.

Get on PrEP, RB. There are other STIs to worry about besides HIV, of course. PrEP doesn't provide protection against syphilis, gonorrhea, chlamydia, etc. But the disease you're clearly worried about—the one you have the most cause to worry about—is one you can worry about a whole lot less once you're on PrEP.