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.

Benny

Hi Cloud:

Les and I went to school together. We played in the same lacrosse team. We double-dated a lot, and compared notes. I won’t bother you with more details. We became the best of friends.

He and I got jobs if only shitty ones in this economy. We are now rooming together in his flat. (His folks gave him a condo.) For the record, I am paying my dues, tho the rent we agreed upon is like, favorable for me.

Les never gave me any reason to believe that he was interested in the guys. Like I said, we have been rooming together for three years now. I would have noticed something, I guess.

Les got dumped by his last GF in the beginning of February. He was cheating. Well, we have been both cheating ever since the freshman year. I hope you won’t judge us… Jock dudes have a reputation to uphold.

For the first time, Les got really upset about being dumped. I was like, Dude, let’s get going, and you’ll score again. No biggie. He said, he could not care less. We ordered pizzas, opened a few cans, and went on bullshitting. Been there before.

He punched me lightly over some stupid remark. So, I punched him back. We started wrestling. I know think, more like horsing around. The horsing bit was a bit new. One thing led to another. I was stunned when he French-kissed me. He also grabbed my dick and went south. Talk about the firsts that night…

Long story short, he gave me the best BJ I have ever had, despite the ongoing scoreboard game he and I have been playing from the day one at college.

I soon found myself on my back, with my feet up in the air, returning the favor. I guess, I was too drunk to really care, and I owed him anyway. I felt like all those girls I heard screaming from his bedroom. Les is a very big guy.

Call me stupid, but I was sure that this was one off. I thought, we were just going to forget about this whole sex thing between the two us, and never even mention this. The next morning, we did our usual routine. Not a word was spoken about what took place the night before. I was determined not to go there anymore.

We got back from work, and it all looked perfectly normal. The usual bull… We went to gym and got back home. He closed the door behind him, grabbed me and started kissing like the night before. I was stunned again. That one-off thing played itself again. This time around, there was no alcohol involved. Again, some awkward silence afterwards with the usual banter to follow.

Fast forward, we had been at it daily for some five weeks before I gathered the courage to break the silence, and tell him that I was really not into this. I was honest. I told him that I enjoyed his BJs like hardly anything sexual I have ever experienced. I also told him that I did not feel like being his bitch. He was very silent at first. Then, he said, we had a deal going on. Something stupid, like I owned his mouth and he owned my ass. It was all good. He started all over kissing me, and I did not resist or say anything. We got into our usual loop.

I know that I simply do not have the guts to end this on my own. I also know that I cannot go on like this forever. I am still dating, taking chicks back to my bedroom and all. He seems to be fine with this. He has totally stopped dating, and spends his sexual energy on me.

I gave talk another chance last week. He looked me straight in the eye, and said, Dude, your hole is my goal. I have never heard him speak with such determination.

I do not want to move out, and stop being friends with Les. I also do not want to have sex with him anymore. I fear that there is really no way of doing this.

Alan

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Guys, your thoughts and comments on this are welcome!

SC