I had an e-mail from a reader the other day…

My name is Jack. I am an avid reader of your blog and I wanted to ask you a question. I am an HIV negative bottom and I crave raw dick and cum in my ass. But, to date, I haven’t taken any raw dick, except from guys I have dated regularly and trusted. I want to branch out and try the occasional raw hookup, but I don’t know how to approach it. Obviously, this is a hard choice to make.

I am considering hiring an escort I know who does bareback occasionally. He claims he is neg and DDF, but I have no way of knowing for sure. He only barebacks for double fee, but I really want to have his cum in my ass.

Based on your estimates, what do you think my risk factor is?

Let’s just say I’m glad I’m not a bottom… It’s not easy making decisions like the one Jack’s making…

There’s a lot he didn’t say in his e-mail… How old is he? Though the fact that he’s thinking of hiring a hooker makes me think he’s not a twink. What are his priorities in life? How comfortable is he with risk in other areas of his life? Someone who drives like a maniac, goes skydiving, or backpacking through war zones is probably more comfortable with barebacking than an accountant who dreams of having the perfect heterosexual-style wedding and settling down in the country with his partner, two dogs and a kid…

I guess what it boils down to is that I think some guys should use condoms since it’s consistent with how they live the rest of their lives, while I think other guys should just give up and get into the mindset that they will become poz… The question is what should those of us who aren’t at one of those two extremes do?

For starters, make your own decisions and don’t second guess yourself after the fact. If you really need cum in your ass and in the moment you’re OK with doing that with a particular guy – don’t beat yourself up after the fact even if you became poz as a result. Bad things happen to people who think negatively… Don’t go there.

Or put another way, realistically think about your limits ahead of time, live by them, and if you don’t wind up living by them re-examine them since you may not have been realistic about things when you were just being theoretical. That’s not to say you shouldn’t learn from your experiences and do things differently in the future (I’m wondering whether the last two hookups were worth it)… Just don’t freak out about things after the fact…

Obviously Jack has thought about things and recognizes his need to get cum in his ass – and not just from whoever he’s dating… If he has that need then it’s good to be realistic about it and deal with it. Suppressing it isn’t a good long term strategy on many levels. So it’s good that Jack acknowledges it and is trying to find ways to scratch his itch…

At the same time he seems really concerned about risk. That’s an understandable step at the point he’s at, but he needs to be realistic about that too in that nothing is guaranteed. All he can do is play the odds and pick tops his gut tells him are neg. But even then he might wind up with poz cum in his ass… He needs to know that might happen and accept it the same way he accepts that when he drives his car on the highway he might get hit by a truck and be maimed for life.

But most importantly, Jack should avoid being consumed by fear. It’s easy for people like him to over think things and get let worry rule their lives. Sex is no different than any other aspect of his life in that to live an interesting life means there’s a certain level of risk. I love NY and find it invigorating to live here. But it’s also tends to be popular with terrorists. I love getting my cum in a guy’s ass, but that can put me at increased risk for HIV. Is there really that much difference between choosing to live in NY and choosing to bareback?

What would be sad (from my perspective) is 10 years from now for Jack to feel like he missed out…