A few years ago, I was living in a van. Dropping out of college had not been a good choice, and now that my parents have passed, taking their good cosigning ability with them, I pretty much couldn’t get back into the university. I worked odd jobs, had a $15,000 credit card debt, and less than $1,000 in the bank. There’s no way I could rent anything, so I traded my funky old Volvo for an even funkier Ford van to have a place to sleep.
Naturally, I was jealous of my old high school friend Paul. As I understand it, his father had helped him buy a duplex when he was still in high school. Since then, he has leveraged that into more than a thousand rental units.
I only heard about him through old friends. Hadn’t actually seen him in years. When we met up, I was ashamed of my position compared to his, but he treated me as an equal. We got to talking by phone every now and then. He knew about my plight, but didn’t do anything about it, not that I was expecting any help. Hell, I didn’t need help. I just needed to come up with some way to make more money than minimum-wage jobs.
I thought of Paul as a billionaire, but came to find out later, his net worth is way less than that. Still in the multiple millions, however.
So, one day, Paul called me up on my cell phone with its cracked screen, and asked me if I knew of anyone who could be a butler. He was going to retire, At age 42! He was planning to make that retirement really ‘special’ in his words. He was going to dedicate every waking moment to philanthropy, and that’s why he needed a butler. He could get more done if he didn’t have to prepare his own meals, do his laundry, etc.
I couldn’t resist at that point, so I asked why he wasn’t married. I mean, couldn’t a wife run a household? I mean, especially if she was married to a billionaire.
He laughed, saying every woman he dated was after his money, so he finally gave up. He actually came right out and said, “I take matters into my own hands.”
It took me a moment to understand that statement, then I laughed, kind of sheepishly, because it was really too much information. I’ve always been kind of shy about sexual matters. I liked to tell myself the reason I didn’t have a girlfriend was due to living in a fucking car, but I suppose the real reason was my generally low sense of self-worth.
Oh, I’ve had a number of sexual encounters with girls, but nothing ever developed into a relationship.
So, it really turns out Paul had been thinking of me. He wasn’t really asking whether I knew of anyone who could be his butler, he was asking whether I would be his butler. I’m no idiot. I suggested that I could do that. He acted like I was doing him a big favor.
The next day, I moved out of my rusty, smelly old van, and into Paul’s guest cottage, and went to work. Paul didn’t give me much direction, just saying, “Help me save time in any way you can.”
It was a bit awkward for the first couple of weeks. More than once I embarrassed myself or did the wrong thing. I think I was trying to be too ‘butlery,’ trying to do what I assumed a butler would do, like you see in old movies. Paul just kept telling me to relax, and follow my instincts. I thought about quitting. I thought if I didn’t, surely Paul would fire me.
Instead, he gave me a raise. I was now making $25 an hour, along with free housing in his cottage, which seemed, well, just great! I got the screen on my phone replaced. I was starting to pay off some of that debt.
Over the course of months, we settled into a routine. I took care of his laundry, I arranged meals, even cooking some of them myself. I arranged his airplane tickets, and even went on the trips with him. I answered his home phone, warding off salespeople and others who wanted things. I sorted his mail. I was even writing checks to pay his bills. Imagine handling a checking account in which the balance never falls below $100.000!
Paul seldom complained about anything, so it was a surprise when one day in a hotel in Atlanta he said that the massage he had received was just awful. I asked about it, and he said the woman just didn’t have the touch. He went on to say when he tried to guide her in what he wanted, she got huffy.
I was there when she left, and had no idea. He was very friendly to her in saying goodbye, and gave her a generous tip. That’s Paul, a good guy through and through.
I’m kind of geeked out about touching people, but for some reason, I just said, “Hey Paul, let me give you your next massage.” I regretted it instantly. What did I know about massage? Plus, that would be way too, um, personal, right? But then again, I was his butler, and always looking for ways to do my job. I felt a little guilty because I had a lot of free time on the job, and it was really quite easy.
“You know, it would save time, compared to waiting for the masseuse to show up and explaining things, and all that. Really Miguel, if you don’t mind, sure, I’d like that.”
A week or so later, I had forgotten all about the massage offer when suddenly Paul asked me to do it. I felt immediately weird. Like a stone in the pit of my stomach.
We arranged that it would happen right after dinner at 6pm. I went to the ‘massage room’ one of the four bedrooms in his main house, unfolded the table, and covered it with a sheet. Paul came in wearing a fluffy white bathrobe, the kind only wealthy people have. He threw it off onto a chair. He was fully nude. Somehow, I hadn’t expected that, and almost choked on my own saliva. He was good looking, but it wasn’t that. It was that my old friend from high school, and now boss, was stark naked. This was just so fucking personal! I was surprised he wasn’t embarrassed being seen nude like that. But I figured we are guys after all. It wasn’t really different than showers at the YMCA, which I’m so glad I no longer had to do to stay clean.
He got on the table and I went to work, massaging his shoulders like I figured it should be done. After all I knew nothing about massages. I asked him to tell me exactly what he wanted. To guide me. At first he was mostly silent, but after a while he was doing a good job of telling me exactly what he wanted. I pressed harder here, rubbed firmly there, and so on. My wrists were starting to hurt, but I wasn’t going to tell him that.
After a fairly long while, he announced that it was time to roll over, so I backed off, letting him flip over on the table. I went back to work on him, starting on his forehead which he seemed to really like, working down to his cheeks, then his neck, his shoulders and upper body. I couldn’t help glancing at his cock from time to time. The hair was trimmed close. Whenever I see that, I always think that marks a man, or woman, as one who is sexually active, or at least has a high libido. Elsewise, they wouldn’t bother, right? I filed that thought away as I worked on his forearms and then his hands.
While I was massaging his hands, another thing which he seemed to especially like, I noticed a side effect. His cock had started to swell, and was now lifted a half inch off his belly at the tip, and pulsing slightly with his heartbeat. I didn’t say anything. I understood that under the circumstances, this might be typical. I had never had a massage, but figured I’d probably spring a boner, too.
I must have been staring at it because Paul said, “Oh, sorry.”
For being caught staring, I felt that familiar old embarrassment feeling again and looked away immediately. All I could think of to say was, “Paul, I think it’s natural under the circumstances.”
“Yes, it is. I don’t know about other guys, but I usually get wood when I’m getting a massage.”
The massage went on, mostly in silence. His erection stayed hard all the way to the end. When he finally got up off the table and put his robe back on, there was a moment when he was standing, facing sideways to me, and his cock was sticking straight out. I hadn’t realized how horny I had become until that moment. That little picture stuck in my mind, and later that evening I jerked off big time just remembering it.
A few days later he wanted another massage, and I gave it to him. The same thing happened with his cock. But this time, toward the end of his massage, he started putting his hand on that hard dick of his while I worked on his feet and lower legs. He wasn’t quite masturbating, but he was definitely touching himself in an erotic way.
“Do you want a little help with that?” That was me. I couldn’t believe I said that. What was I going to do, jerk him off or something? Geez!
“Uh, um, no, that’s OK Miguel.”
I was relieved and disappointed at the same time. Somehow, I really, really wanted to touch that cock of his.
Then, after a moment, he quietly and hesitantly said, “But what I would like is a bit of a testicle massage, I mean, if you wouldn’t mind.”
I didn’t say a word. I just reached over and started manipulating his sack. He let go of his penis, letting his arms fall to his sides on the table. His boner was harder than ever. He instructed me on the right amount of pressure, and the exact way to hold his balls, one in each hand between thumb and first two fingers, and kind of roll the testicles back and forth in my fingertips. I could see by his super-relaxed expression that he was in heaven.
This went on for quite a while when suddenly his body tensed all up, and cum started squirting out of his cock. Instinctually, I wrapped my fingers around his cock, stroking firmly up and down, finishing his orgasm properly.
Again, immediate embarrassment. Surely, I had gone too far. What was Paul going to say?
“Oh, thank you Miguel. That was spectacular!”
These past few years the tradition has continued. Every few days Paul gets a massage with a happy ending. We’ve settled in and are the best of friends, discussing everything. He even has me helping manage his ever-growing philanthropic organization. I think some of his financial managers resent my closeness to Paul.
I wouldn’t say we are gay lovers or anything like that. Our sexuality hasn’t gone beyond the massages. And, he has never massaged me or even seen me naked. It’s not that he hasn’t offered. He has. But to me, it seems more appropriate since he’s now paying me $125,000 a year, to keep it ‘professional.’ However, most of the time after the massages, I return to my cottage and bring myself to a nice orgasm. I don’t know, maybe someday I’ll take him up on his offer. It’s hard to maintain my resolve. If he offers it for a birthday present or something… oh, man!
I’ve been dating Judy for a year. She stays overnight in the cottage quite often, likes Paul, and knows about the massages. He lends us his massage table so she and I can play with it from time to time. One of her favorite pastimes besides ordinary sex has been been asking me for blow-by-blow descriptions after one of Paul’s massages, while she does the same thing to me that I’m describing.