Gay Agony Uncle: Buddy with Serious Benefits…

So far, I have not posted any of my private correspondence with the guys asking for help or advice if I knew them personally. Theo, my ex-buddy, who lives in Munich, Germany wrote about this, and asked for advice saying that he would appreciate as much help as he can get.

Here is some background that Theo did not mention both because he is a very down-to-earth guy and because he knows that I know all of that.

He is 24, gorgeous German, blond, 6”3’, big guy in every sense, if you are catching my drift. He also sports a genuine six-pack which I once used as a washboard to wash his T-shirt because he had lost a bet and had to take the tickling. He has a very light geeky streak about him which simply makes him even more desirable. He is a country guy who is trying to make it in the big town, and he takes his career and everything about his life very seriously. He is out and about to the people who need to know this but is miles away from being the heart-of-the(circuit) party dude. Theo is into successful guys who have good lives. He goes by the rule, “if you want to top me, you’d better be bigger than me, in every sense”. I’d also say that he is a bit of a loner, minding his own business first.

Give it a shot or two. Thanks.

Dear Cloud:

Thanks for remembering my graduation and for sending your present. No one else really bothered, so your parcel made my day, or more, like a week.

I got the job which I really wanted even couple of months before the finals, so as you knew, I was all totally happy about this. At first, it looked like that all that sweat with the exams, the finals and the “summa cum laude” made itself paid in the end.

Our CEO/the owner of the company I work for now, has assigned me to the project group that he is heading himself. As you may imagine, this is the toughest, most interesting and most rewarding project we are involved with at this time. This is very fine with me. I do not mind putting extra work for all that extra reward and benefits I have been getting since December 1, 2009. So, you would say, “Life is good”, wouldn’t you?

You have been always teasing me about the total absence of my gaydar if you still remember our times together during my freshman year in Munich. Well, even I have noticed that my boss was actually flirting very heavily with me. This was pretty obvious, and though no one said anything, I knew that people must have been talking about it behind our backs. For some reason, I went into my sympathy fuck mode, thinking that if I let him suck me off, he’d let go, and we’ll be all back to normal. I absolutely had no interest in Max, my boss. Just the opposite is true.

He has a huge beer gut, bloated and blotched skin. Add an aggressive, “I-know-everything-better” manner to all of that sad appearance… As you know, definitely, not my type of guy.

Well, I accepted his; I think 20th invitation to come over to his place for some “good red wine”. I think, I was really trying to save his face, as they say. He surprised me by opening a really great bottle of red, pretty much just like you used to. No doubt, I knew what was coming, and just wanted to get done and over with. I thought, once he got what he wanted, he’d move on to someone else and let go.

Max had other plans, though. He amazed me by dropping his pants and showing a tool that would look good on a bull, back home. The usual office talk like “Max has got a very big dick and huge balls to take it on that guy” or whatever, suddenly got a completely new meaning.

From then on, this was all his game. I must have fainted out of sheer pain as he penetrated me, and do not remember all that was taking place in his flat. But I knew that he did manage to split me open using mere force. He also managed to have me shoot my load in sync with his thrusts. In the middle of my ejaculation he stopped fucking me, and I was unable to unload all I had. I felt totally powerless. He was in absolute control. He mercifully resumed his shafting, so in the end, I got my rocks off, in an ocean of excruciating pain. I was not able to stop tearing up, so I took a taxi cab ride back home. Something I have never done in my life before. But I recovered.

Two days letter, he texted me to come over to his flat for some fun after work. By that time, I knew what was coming my way but decided to go anyway. I was simply unable to believe that this was really happening to me. And a part of me wanted some of that experience again.

If anything, my wish was fulfilled. Max saved the wine bit this time around, opened the door of his flat completely naked, and told me to take off my clothes and hit the bedroom. I managed to stay conscious this time mostly because I knew what kind of pain I was to expect. Again, he had me shoot my load without touching myself at all. I managed to stumble out of his flat, pick up the bus and then the subway, and suffer the looks of the people around me who all must have thought that I was totally drunk, high or something.

On my way out, Max told me, “Hey, we’ll be seeing each other pretty often, so here is something little for you!” I barely registered this because the only thought I had at that time was to get back home, take couple of painkillers and sit in a warm bath for this terrible pain to abate. I managed not to tear up this time around.

Next morning, I remembered what Max told me on my way out. I opened the envelope and found five crisp, new EUR 100 notes in it. I did not feel anything at that time. It actually felt as if my mind stalled. I really did not want to think about this at all.

Max fucks me now two or three times a week for the second month in row. Once a week, he hands me an old, usually used hotel envelope with five new, crisp EUR 100 notes in it. Neither he thanks me for the sex nor do I thank him for the sex or money or anything. We really do not talk in private at all. I know that I need to take my clothes off and lay on my stomach. He does the rest in silence. He sometimes says “Bye”. That’s all.

I do not need to tell you that I know that I have gotten myself into a huge mess here. I do not know what to do next, except to share some of my thoughts here with you, and ask for your advice.

I do not want to break up with Max. Despite the pain and obvious humiliation, I am still amazed at the sex I am having with him. I have also admitted to myself that more than EUR 2’000.00 a month actually means a lot to me. He also has a final say as to who gets promoted in his company. I cannot stop wondering, if this really makes me a male prostitute or not.

Max is married and has two kids only couple of years younger than I. I often think that I am actually cheating on his wife and their family. I know them only very superficially but I still feel very bad about this. I wish he had the balls big enough to stop this, since I am obviously lacking in this department.

How long will this go on? And how much more of this can I really take? Will this stop by itself? After all, I am not the only young guy around.

I am pretty sure that I know what you are going to say to all of this. I have known you for a while now. Is there any way I can put the square peg in a round hole and get away with it?



Hey Theo:

Putting a square peg in a round hole is what most people try to do most of the times. The spin docs and all the shamans alike call this “a challenge”. By that same merit, many people waste their lives wondering as to why they are facing that particular “challenge” and not the one they would be rather facing, if it were all up to them.

Loads of things out there are really not up to anyone of us in particular. They just happen. Both proverbially and virtually so…

Max seems to be calling all the shots here, and only he knows how long he will want to keep you around. You have admitted to being fully compliant with this arrangement for a multitude of reasons that clearly outweigh all the other reasons for you to break up with him. Max really calls all the shots not only because he knows how to do so, but just as much because you have agreed to go along with all of this.

I am sure that most people, if asked, would tell you to break up with Max now, and move on ASAP. You have indicated that this is NOT what you want to do. This really goes on to tell you that Max and you will stay in this together until at least one of you decides to move on.

I see your point in hoping that Max may bump into another young guy of his liking, and set you free again while not holding this against you (or more likely, against your professional career in his enterprise). No doubt, all the things eventually do come to an end, one way or the other. However, if you start viewing this whole little affair from his point of view, you’ll agree that he has hardly any reason to take both additional risk and expense in order to get someone else to replace you for as long as you are there where he wants you. Most of us with corporate careers know that even the top talent in any field can be replaced. It is only so, that by far most of us righty shy off the expense and effort involved with such replacements.

It is only really up to you decide if this arrangement really makes you a male prostitute or not. You have accepted his advances without any promise of payment of any kind in the first place. It was only Max who decided to use his money and power in order to make sure that you stay where he wants you to be. Would you be still accepting his invitations to come to his flat for “some fun”, as he puts it, if it were not for the financial and career benefits you have been enjoying so far? If the answer to this question is “No”, you know what this really means, don’t you?

I see no reason for you to share any of the moral responsibilities that Max may or may not have vs. his family. First, you really do not know what kind of arrangements Max has with his wife in the first place. There is obviously quite some money involved here, and it is quite conceivable that both he and his wife have opted for some sort of social co-habitation rather than for a possibly very expensive divorce. None of this is really any of your business, and there is no reason for you to act as his moral guardian in any way. If he is cheating on his wife and family, he alone will have to cope with this.

Overwhelming as this all may be to you, you still ought to look at the bigger picture here. First and foremost, you have got your life to live. All the benefits, material and immaterial alike notwithstanding, you ought to regain your life. If you lack the strength to break up with Max on your own, try to contain this relationship within its proper boundaries. You want to start meeting up other people, making friends and enjoying your life beyond the affair you are having with your boss. If you establish a meaningful relationship with someone you really like (and love) breaking up with Max may become a matter of necessity.

Last but not least, you have every reason to believe that you may come across a successful man who will treat you with love and respect that you deserve. You are quite an extraordinary guy, and it is really up to you connect with someone who will meet your expectations both in your bedroom and beyond.

Keep in touch,


~ by silverrrcloud on February 6, 2010.

5 Responses to “Gay Agony Uncle: Buddy with Serious Benefits…”

  1. SC — Wise words. I couldn’t agree more with your advice to Max!!! Can I ask who the gorgeous guy with the goatee is in the photograph you posted along with this advice column?

  2. Thanks, freddiehoney!

    I took all of the pix in this blog save for the illustration pix accompanying text entries… These are web finds.


  3. Your photography is wonderful. So I guess you don’t remember where you found the goatee guy pic? I’d love to see more photos or even the videos of him!

  4. Sorry… The web is just too wide…


  5. Indeed! No worries — if I find anything on him, I’ll let you know!

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