Gay Agony Uncle: Houseboy Dilemma

Hi Cloud:

I am out to all of my friends but not to my family. I am GAM, 20, in-shape, student at one of the Bay Area universities.

My folks live overseas, and are no longer in position to help me pay my tuition and other expenses. I have a side job which is a real drag-on. Nonetheless, I am barely making ends meet. I know that few people are having a ball in this economy.

My options are very few: drop out or get some serious support and graduate in time.

A few months ago, I met a guy in San Francisco who was way over my age limit but who charmed me into a NSA ONS. (I might have been a bit too desperate, and having a worst case of blue balls did not help either.)

It turned out that he was a successful PacHeights guy living alone in a big Victorian. Putting it plainly, he is rich.

We exchanged phone numbers, and kept in touch. He’d take me out to a fancy dinner and spend more on a bottle of wine than I can afford for my food for a fortnight. We always ended up at his place for some fun afterwards. I am not complaining or anything.

I told him that I was going through a very rough patch because I needed to vent. He was sympathetic but reserved in his Cal-WASPish way. Frankly, I did not expect any offer of help coming from him. The truth of the matter was that he was buying dinners, and I was providing some post-dinner entertainment.

I know that this sounds cheap. A friend of mine told me that I was whoring around for a fancy dinner and couple of glasses of wine. I am both too stressed and too unsettled to start looking for a BF while saving on the basic food and heating. So, dinner and sex sounded better than anonymous sex and no dinner. This dude may not be the man of my dreams but who is there to say that the guys I would pick up on the Craig’s would be any better?

A week ago, we met over the dinner, and he commented that he was happy to say that this became a regular, weekly affair. I never thought about it, but, yeah, he was right. It sure looked like one. The part I liked was that it was all totally a NSA affair. I kept my mouth shut on that one, tho.

Out of the blue, he said, he was thinking about my problems, and had a suggestion to make. He needed a housekeeper for a few hours every day. The house was big enough for six people to live in, anyway. He was splurging a lot of dough on his part-time housekeeper, and was not too happy with her anyway. He would be happy to provide free housing, free food, and a decent pay for my work.

I have never lived in with anyone except with my family and a nerdy roomie during the freshman year. I asked him for some time to consider his offer, and we went on shooting the usual breeze.

Judging by the way he has put it, this would be a win-win situation. I would be out of my troubles, and he would be having his home taken care of. I have no doubt that my duties would include sharing his bed, too. After all, we have been having sex from the very first day we met.

I was OK with a NSA relationship. Moving in, accepting the free food and lodging, plus a pay for my work would be a different game altogether.

So, you could say, I am between the rock and the hard place. I am not emotionally attached to him in any way. He is a nice guy. Sex is OK. But I do not feel like making a binding arrangement out of this. On the other hand, beggars can’t be choosers.

Should I take a plunge here?

Thanks a million for taking your time over this.


~ by silverrrcloud on March 30, 2012.

2 Responses to “Gay Agony Uncle: Houseboy Dilemma”

  1. Just make sure you don’t catch anything from him.

  2. I would go for it if I were in your shoes.

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