PEARSON: Paying for it

In the Craigslist m4m section, there was a guy who looks to be about 50, but he said that he specialized in being “generous to college-aged guys who are straight or straight-acting.” This makes sense, and I fit this demographic, but what does ‘generous’ mean? Is he big? Fat? Is he a safe guy to meet up with? What would you do? M 4 Generous M

What would I do? Oh boy . . . This is quite a question. But, since you took the time to ask an honest question, I’ll do my best to answer honestly. Lets start with a short disclaimer: There is absolutely nothing wrong with looking for a casual encounter online. Now, having said this, there is a huge difference between a random hook-up, and getting paid for sex.

Yes, M4GM, you are being offered money to have sex with this silver fox. A “generous” partner, a man who is offering “roses” or “chocolates,” is actually offering to pay you cash money to meet up with him. So, the real question is: How do you feel about being paid for sex?

Well, you asked what I would do, so I’ll tell you the truth: Freshman Luke got around. He has since grown up, and no longer trolls Craigslist looking for dudes, thank goodness, but Freshman Luke usually became Drunk Luke. Seeing as my usual booty call was out of town one weekend, I booted up my computer and headed online. I received a very similar email to the one you quoted, M4GM, and I replied that I was interested. So, after a few awkward emails about how he “does this all the time LOL,” and how I “should invite all my friends too, OMG,” he drove over and picked me up. (The strangest part of all of this was how he kept using emoticons, and wrote emails like a 14-year-old girl).

I’ll skip to the long and short of it, he was short, I was long. The old man was even older than the pictures he had sent over, and had put on about thirty pounds since the photo was taken. The entire experience lasted about ten minutes.

Just as he was about to get started, I slipped a condom on. This, dear reader, is the most important part of the story. No matter what you decide to do when a strange old man offers you $50 to fellate you, make sure you use protection. Yes, my risks here were minor, but even so, I could only assume the number of other strange men who had been with this creeper.

So, to wrap up, M4GM, whatever you choose to do with your generous older lover, keep this in mind: Technically, any payment for sex is grounds for a prostitution charge. (This is something that Freshman Luke never thought about). Is $50 really worth a 3 a.m. call from the police?

Luke Pearson is a weekly columnist for The Daily Free Press. He can be reached at lpsexquestions@gmail.com