Sex & the Cigar

10/16/08 - Dear Sex and the Cigar,My socially awkward roommate has taken up a habit of pleasuring himself when he thinks I am asleep. I would try to get him a girlfriend, but it is questionable as to whether he even likes girls or not. What should I do?

- Seen Too Much



Dear Seen Too Much,

Oh boy. Not this guy! I know just the guy you're talking about. He's nice but doesn't really know proper etiquette around people? I bet he has really strange hobbies because he thinks they're cool and might strike up a conversation.

He's the guy who doesn't even watch normal porn while wanking in front of you. He's probably into something weird like bestiality or anime. Am I right?

Well the truth is, as socially awkward as your roommate is, he knows what he is doing is rude and completely inappropriate. But he doesn't care.

From what you told me, he obviously isn't getting laid, so this is what he needs to do to level himself out. I heard it's also good for the prostate so maybe this is a medical thing. But probably not.

I hope you gave him a clear sign that you were awake. I would never sit there and allow that to happen. Too bad if he has a case of blue balls, you have class the next morning.

The next thing I'd do is tell him you know what he was doing and that it makes you uncomfortable.

I know it might not be the manliest conversation to have, but I think you'd want to deal with this. Tell him you don't appreciate looking over and seeing him do that. Tell him he should go to the bathroom if it's absolutely necessary. Hell, print out the anime for him if you must.

There are a couple more options you could try in this situation. However, they're a bit ballsy. You seem like a heterosexual man based on your thought to get him a girlfriend, so this next scenario might not be the one for you.

Next time you catch your roommate "spanking his monkey," offer him a helping hand. He'll either stop what he's doing out of complete shock or take you up on your offer. If he does in fact like girls, you're in luck. You have successfully creeped out your roommate and gotten him to stop.

However, your sexuality is now in question, though I think he'll know you were joking. But if he takes you up on your offer, help if that's what you're into, or tell him you were just joking to try to get him to stop. Either way, I think he'll stop.

Now if that approach isn't the one for you, you could always creep your roommate out in other ways. For example, giving him a taste of his own medicine. When it's late but you know he's awake, sit up and enjoy yourself. He'll soon see how awkward it is to be the other person.

If all of the above options fail, you're in luck because prostitution is legal in Rhode Island so long as you don't promote yourself on the street. Yes, it's true. In Providence prostitution is completely legal behind closed doors.

So, jump onto craigslist.com, scroll down to services, click 'erotic' and choose your roommate's preference. There are all sorts of interesting, sometimes desperate (which is preferable in your case) people looking to fulfill their fantasies with complete strangers.

I'm sure you could raise the money to treat your roommate for an hour or so. One way to raise the money would be to meet up with one of the many older men and women who offer to give you money for college in exchange for ... favors. Or, just send your roommate to one of them. It's a win-win situation - you get to sleep and your roommate gets lucky and a few extra bucks!