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Butler With Benefits

I’ll admit I’m a wealthy man. It started with my great-grandfather, who was a cobbler during the great depression. It turns out that repair businesses did well while everyone else suffered. People couldn’t buy new shoes, so he had lots of customers. Then, World War II came along, and leather could not be spared to make new shoes, so he had even more customers.

He invested the money in buying the building he was in and charging rent to the other small retail businesses in his building. Then he bought more buildings. You can imagine that his children and their children, and finally my generation have followed his footsteps and all done very, very well in commercial real estate. For four generations, our family has also been heavily philanthropic. Don’t worry, we can afford it! It’s more than just philanthropy. It’s a love for all humans – and animals. I was taught to be polite, kind and caring to everyone since I was a baby.

So, here I am, otherwise a typical trust-fund baby. For instance, on my 18th birthday, I was given a hotel. A one-hundred-eleven room hotel at 111 Broadway. Really! I didn’t pay much attention to it. I have managers, lawyers and accountants to take care of all that.

I was also given something else on my 18th birthday. My ‘man,’ that’s what I call my butler, who has been with me for 8 years. Jonathan used to work directly for my father. He is a sort of combination chauffeur, personal assistant and dresser. He arranges my air travel, handles my email, and even selects my clothing in the morning. That way, I can spend more time on business. I mean, I could retire right now, and just live off my assets. But somehow, my family has got me so trained to stay focused on growing ‘the business’ as they call it, that I can’t imagine doing anything else. Well, I did go to college and get an MBA, but that was just part of focusing on the business. It’s all about philanthropy and I can do it better with even more money, right?

But anyway, back to my 18th birthday. So that evening, Jonathan comes in and says he has something he wants to tell me. I figured he was going to give me some cufflinks or something. And even though Jonathan and I have become close friends, I was thinking, OK, I’ll be polite and graciously accept whatever birthday gift he has for me.

But no! He tells me he used to perform a certain service for my father. He didn’t quite explain it at first. I was starting to imagine the worst. Like even though my father is a very morally correct and kind man, I was thinking, “What kind of service? Eviction agent? Supplier of drugs? Hit man?”

He slowly, and somewhat embarrassingly explained the service. He said that for a while before my father was married, he was so involved in business that he didn’t have time for dating. Plus, most of the women who came into his life were gold diggers. So Jonathan took care of my father’s sexual needs. I was thinking, ‘You mean, he procures prostitutes?’

But no, it was something more direct. Then I understood! Jonathan was satisfying my father’s needs directly! He was giving him handjobs! Geez! Some things you don’t want to hear. I was simultaneously, fascinated and grossed out. But something else too. I started to feel a certain rising feeling in my penis. My god, I was getting erect just hearing about Jonathan giving my dad handjobs.

Jonathan went on to explain that my dad continued to receive occasional hand jobs after he was married. And get this, sometimes Jonathan gave my mother clit jobs and even sucked her clit. He just came out and told me that.

In a way, I shouldn’t have been surprised. My parents have always been open and experimental about sex. Like, we went to nude beaches occasionally since before I can remember. And, I have accidentally seen my parents having sex, which didn’t seem to faze them. And they have caught me wanking. Which also didn’t seem to faze them. But Jonathan, that was shocking news!

So here’s the deal. Jonathan told me in no uncertain terms that if I’d like handjobs, that is part of the service he offers. (And all for $130,000/year. I should give him a raise).

For the first few weeks after I turned 18, I did not take him up on his offer. Then one evening, after flirting unsuccessfully with a beautiful Asian girl who is my mother’s secretary, I was all horned up, and Jonathan talked me into trying his ‘service.’ It was a bit awkward at first. In order to make me comfortable, as I stripped, so did he. This is Jonathan I’m talking about. I’ve never seen him without his tie, his immaculate jacket and pressed pants, and polished shoes. Turns out he is a great looking guy for a 50-year old. Slim, just a bit shorter than me at 5’7,” and with that beautiful African ancestry. I’m only half-African, approximately.

It’s not true what they say about all black men having big dicks. His is average size, or maybe even a bit less, pretty much like mine, although he is not circumcised and I am.

Anyway, he did give me a beautiful handjob that evening. Even though I didn’t touch his dick at all – he said he didn’t want reciprocation, he did get nicely erect, which I enjoyed seeing. Jonathan has wanked me a hundred times since. Somehow, he always brings something interesting to the table. In all the times he has jerked me off, no two have been the same. And, he seems to read my mood. Sometimes I like something kind of rough, like rubbing the palm of his hand over my glans to make me squirm. Sometimes he is so gentle, I can hardly tell if he is touching my frenulum or not – what a fantastic tickling sensation that is! Sometimes he massages my balls very light and lovingly. Sometimes he squishes the hell out of them, which I absolutely enjoy when I’m in the right mood. Sometimes, I jerk him off. That’s right, I enjoy giving as much as getting, and he really does like the reciprocation.

There have been a few women in my life. Jonathan’s service doesn’t interfere at all. In fact, I told my best friend (with benefits) Susan about Jonathan’s service, and she wanted to see it. So one evening after coming home from the office, there was Susan and Jonathan on the sofa, naked as the day they were born. She as white as vanilla ice cream, he as dark as the best chocolate. They were idly stroking each others genitals as I arrived, and the invitation was obvious. We all masturbated together in a great big pile of happiness.

Well, that’s enough rambling from me for now. Have fun, and I hope all your families can become as successful as mine has been.

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