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My Boss is a Weirdo

weirdo boss massage

My boss is a weirdo. So here’s the story:

My rat of a husband left me with two kids and no money. I needed a job right away. I always thought I’d be a traditional mother, so I’m not trained for much of anything. Oh, I did well in high school, but then I went to beauty school. I found out that cosmetology is really hard to break into. It takes years to build a clientele. I had my kids instead. Then Kyle left, and there I was with nothing, and two kids who needed to be fed.

It got really bad. I had to sell things, even my car. I was looking at Craigslist every day. Then, the last thing left that I could sell was the computer. I went to the library to use their computer when the kids were in school.

A job popped up that I felt qualified for. It was personal assistant / maid. I called, and a phone interview with the guy went well enough. Then he said that part of the job would be massages. I was a bit taken aback, thinking, “Oh geez, this doesn’t sound right.” I told him I’m not a certified massage practitioner. He was OK with that. Under ordinary circumstances, there’s no way in hell that I’d have consider such a thing, but what choice did I have?

I took a bus to an interview and had to walk four blocks from the bus stop. On the walk, I practically convinced myself that either I wouldn’t get the job, or this was going to be one of those incidents you hear about out, where someone responds to a Craigslist ad, and gets killed. Oh, my poor kids.

I arrived to discover the guy had a really huge house. A woman about 50 years old let me in with a nice smile. After a moment, a very nice and fit-looking man, maybe about 50 years old, beckoned me into his library. Yes, a library. An office with floor to ceiling books on three walls, like you see in the old movies.

We talked a bit, the whole time, me waiting for the weirdness to come out. At least I knew I wasn’t going to get killed. Not today. He was quite a gentleman. Friendly, inquisitive of my life, but not prying. I told him about my lousy husband leaving, and my kids. It took a while for the conversation to turn to the job.

He literally wanted a personal assistant / maid / masseuse combination. The first two parts, I could handle. The last, I was kind of geeked out about. He explained that his current “PA,” as he called her, the woman who greeted me at the door, was moving to California.

Suddenly he yelled, and I practically jumped out of my chair. “FRANNIE.”

She came into the office. “Would you tell this young lady your honest opinion of your work here?”

I figured it could be a setup. She might say anything he wants her to say.

“George has been great. Let me tell you, you want this job!”

She then turned to George, and said, quietly, “Can I tell her about the massage part?”

“Oh, yes, please do.”

“Well…” and she hesitated.

“It’s not really a massage. Um…”

“Go ahead,” he beckoned.

“George has a thing about his, um… testicles. He likes a testicle massage.”

Fuck! I knew it. The guy was a weirdo. Damn, damn, damn! This job was a dead end, too. Now what? There was nothing left to sell. I had applied for welfare, and food stamps, but that wasn’t going to kick in for another month. I started to get up out of the chair. Then I sat back down. I couldn’t just turn this job down. But I was feeling angry, and cynical. Why me? Why did all this have to happen to me? Was God teasing me with shit like this? Like, a guy who wants his stupid balls massaged?

I just blurted out, ‘Yeah, and what else?”

Frannie turned to me, and said, “I know it’s strange. I felt just like you when he told me. But let me tell you something, and I understand that you may not believe it: Testicle massage is all it is. Really and truly.”

Thinking it over rapidly, I knew I was trapped. I had to, absolutely had to take this job. I mean, if he even accepted me. He had yet to tell me I had the job.

“I’d like to meet your kids.”

I was very reluctant. I didn’t know how weird this guy was. Plus, getting them on the bus and all, that would cost money, and time that I could be looking for another job. I was just about to explain my financial situation in more detail but he interrupted me.

“How are you getting home?”

“The bus.”

“Can I give you a lift? Your kids will be home from school soon, right?”

I didn’t like the idea of having him over to my place. Mostly because it was such a small, crappy apartment. But, saving the bus fare, and getting home quickly was appealing. I hate taking the bus.

“OK, thank you,” I found myself saying.

We went out back, and got in his very nice Mercedes van. The thing was some sort of small motorhome vehicle. I guessed it probably was worth well over $100,000.

We got there. I offered him a soda, which he declined. We talked a bit. I was starting to warm up to him. At first the picture in my mind of him naked, and Frannie massaging his balls sickened me. Now, the mental picture was changing. It started to amuse me. It almost made me laugh. I still hadn’t quite made the mental connection that if I got this job, I’d be doing that.

He met the kids. He seemed to like them. They liked him. They all related quite nicely. After only a few minutes, he said he had to leave. He didn’t say whether I’d get the job or not. I was afraid to ask. As he was going out the door, he turned around, like to shake my hand. Instead, he handed me two $100 bills, saying, “For the kids. Pay it forward.”

I ran into the bedroom, closing the door behind me, fell on the bed, and burst into tears, trying to keep it quiet so as not to alarm the kids. I can’t really tell you what I was feeling. The afternoon had been so overwhelming. I think it was mostly relief to have a couple hundred bucks for some food.

Frannie called me the next day, “I’m so sorry, George picked someone else. But he really liked you.”

I was back on my bed crying again.

An hour later the phone rang again. It was Frannie. “The other one didn’t work out. You’ve got the job, if you want it.”

I was back on the bed, crying yet again. This time, it was tears of relief and joy. A few minutes later, I ran down to the landlord, giving him one of the $100 bills, taking some of the pressure off me for the rest of the rent. The landlord had been good about my tardiness.

An hour after that, there was a knock on the door. A stranger was standing there. A young man. “George sent me,” and he handed me a set of keys. “He said you’ll need a way to get to work,” and he pointed at that Mercedes van out at the curb.

I got the kids off to school the next morning with butterflies in my stomach. Yes, I felt relief, but I kept thinking about the job. The personal assisting didn’t bother me. I’m intelligent. I can figure things out. Being a maid didn’t bother me, although the house was huge. But, the massage thing, that was weighing heavily on my mind. What would it be like? How would it go?

I had never driven such a large vehicle. In fact, I had never driven such a nice vehicle. One in which all the windows and the air conditioning actually worked. It was a bit nerve wracking, but fun, too.

Frannie showed me what to do. Where the vacuum cleaners were. What rooms he wanted cleaned, and how he wanted things done. There wasn’t as much involved as I thought. It turns out that George has a real maid come in and do major house cleaning once a week.

She showed me her desk, and the personal assisting things. That too, was going to be simple enough.

I wanted to ask her about the massage thing, but just couldn’t bring myself to bring it up, and she wasn’t volunteering.

Around 10am George got up, shuffled into the kitchen. I had assumed that he might like some coffee, and had warmed some things from the fridge noticing that everything in the kitchen was natural and organic. I was a bit jealous, I’d feed my kids that way, if I could afford it. He was immediately appreciative.

He announced he’d like his first massage in an hour. He must have seen the deer in the headlights look on my face, and said, “Oh, don’t worry, it’ll be fine.”

Oddly, I believed him. For the next hour, I dusted his library, and tried my best to keep my mind from spinning out of control. At one point Frannie appeared, wished me well, and left – forever.

At the appointed time, I went to his exercise room. He was already there, standing in a bathrobe, next to a massage table, and doing something on his phone. My heart was in my throat. I just didn’t know what to expect.

He smiled pleasantly at me, then took his bathrobe off, revealing nothing underneath. He was stark naked. I had expected something like that, yet I hadn’t quite pictured it.

George wasn’t horrible looking. In fact, quite handsome for an older guy. There was not an ounce of fat on him. I was momentarily shocked to see that he was hairless in his genital region.

He got on the table, face down. I gingerly approached, and asked about massage oil.

“Oh, I don’t need that.”

Not knowing exactly what to do, I touched his shoulders, then started kneading them.

He went “Ahh” in a way that let me know I was doing the right thing.

As a few minutes ticked by, I worked my way down his arms, figured I should massage his hands a bit, which he seemed to appreciate. Then I did his back, skipping over his butt, to his thighs, then his lower legs, and his feet.

Somehow knowing I had to, I returned to his back, and this time, I worked my way down to his feet again, but not skipping over his butt. It felt rather nice massaging him, and I rather liked touching a man’s butt. George was fitter than Kyle, and better looking too, even though he was like twice Kyle’s age.

Then it was time for him to roll over. He had an erection right away. Was I expecting anything different? He didn’t apologize for it. In fact, he didn’t say anything.

Feeling somehow stupid, I massaged his forehead, the sides of his neck, his shoulders, his arms, and hands again. Then I went for the torso, and worked my way to his feet, skipping over the genital region. He stayed erect the whole time. We both seemed to be ignoring it.

Now, I knew that the real deal was testicle massage. That’s what he had so clearly stated, through Frannie, that he wanted. I felt like I’d lose points if he had to ask me, so I just reached in and went to work.

Making it a point not to touch his penis, I very lightly stroked his scrotum with the fingers of both hands, being rewarded with another “Ahhh” from him.

I did it for quite a while, slowly evolving into firmer action. Pretty soon, I was kind of squishing his balls between my fingers and thumbs, one testicle in each hand.

For the first time in a while, he spoke, “That’s wonderful! Keep going, but no firmer please. That’s just right.”

I did as instructed. I must have been doing that for twenty minutes, just wondering what was going to come next. Would he ask me to disrobe? I was half-expecting that. Was he going to want a handjob? I was fully expecting at least that.

Suddenly, he sat up, saying, “That was wonderful.” He sprang off the table, and put his robe back on.

I did a load of laundry, and various things around the house. I didn’t see much of George. He spent most of the time in his office. Around 3pm, he announced my day was over. I had only worked from nine to three. He said, “Take the Mercedes and get home to your kids,” handing me another $100 bill.

You may find it strange that we never talked about wages. I just figured it would be around minimum wage, and was happy for whatever it might be. But, only six hours, at minimum wage, wouldn’t go far. The $100 was certainly a wonderful surprise.

The next day was quite similar. Mostly housework. At 11am, once again I massaged him. He instructed me that I should skip the general massage. He mostly wanted to get right to the testicle massage. He was erect the whole time. After twenty minutes, he got up, thanking me, and left the room.

A month went by. A busy, head-spinning month. George said the Mercedes was mine to use as I saw fit. He’d rather drive his Chevy pickup truck. It was a new, top of the line truck, of course. I found out more about George. He had never married. He said he wasn’t interested in women, or men, either. It turns out he was a professor of economics who really enjoyed imparting on youngsters how to succeed financially, which he had obviously done handily. He owned 170 rental units throughout the city. In fact, much of my personal assistance tasks were actually handled by his management staff.

Oh, and here’s the biggest thing: He insisted that the kids and I move into his three-bedroom guest house out by the pool. So, I was getting free housing, free food, organic food, I should mention, and he was paying me $80,000 per year. I was so delighted! When I kept expressing the delight, he’d say one of two things each time, “It’s for the kids.” and “I’ve got plenty of money. I need to spread it around.”

He loved the kids, and they loved him. They started calling him “Grandpa” and he seemed to enjoy that very much.

They daily ‘massages’ continued. He was always erect. Not at the start, but after a couple of minutes, I’d see his penis slowly get hard, and then it would stay that way during the whole session. Sometimes, the testicle massages would last as long as an hour. He said it was like meditation for him, but better. More beneficial. I certainly believed him.

He never once ejaculated.

One day, I came into his office for something, where he often worked just in his bathrobe, and sometimes stark naked. I was fine with that. I hoped the kids never saw him that way, and as far as I know, they didn’t. However, sometimes he’d swim naked in the pool. There’s no way they didn’t see that, but I was reasonably OK with it. It was natural. George was very natural. I started taking to swimming in the pool, sometimes even with George and the kids. He’d be naked, we’d be in swim suits. My swim suit evolved from a modest one-piece to a bikini, then a very skimpy bikini. I couldn’t quite bring myself to swim naked with the kids. Part of me wanted to. Part of me wanted the kids to feel OK swimming naked, but I wasn’t about to push the matter.

So, one day I came in to his office to find him naked, but also masturbating. I thought he’d jump in fright from being discovered. Kyle certainly would have. But no, he just kept right on going, as I set the some papers to be signed on his desk. I didn’t say anything either.

That’s happened a few times now. Once I was in there as he ejaculated. It was surprisingly glorious. He arched his back, moaned, and a good few spurts of semen squirted out of him, which he caught cleanly in a paper towel. He then sat the wadded up towel on his desk. Without a word, I picked it up, and trashed it in the kitchen. Everyone seemed fine with everything.

And that’s where we are now, about a year later. I don’t dare say we are a family, but it certainly feels like it. It feels very good to me. George has never once raised his voice in anger at me or the kids, yet he has been firmly instructive to them a time or two. I have a feeling this is going to go on for many years. Even when I have enough money to quit working, I probably won’t. I’ve come to really enjoy everything about my job, especially the massages.

You see, I’ll be able to quit soon if I want to. I’ve learned a lot from George. I now own three houses, all of which I keep rented out. The kids and I still live in the guest house, George and I would not have it any other way.

Oh, yes, sometimes, when the kids aren’t around, I’ll bring myself to fantastic orgasms while picturing George’s massages. One of these days, I think I might try giving George a handjob after the testicle massage. He’s never asked for it. I wonder why? Is it because he’d think it’s inappropriate in some way? Does he think I’d mind? I wonder how he’ll react to that?

In my fantasies, he and I are married and we fuck our heads off daily. I mean, he’s really only eight years older than me. Somehow I think that fantasy is going to come true.

1 thought on “My Boss is a Weirdo

  1. What a great work relationship, CFNM is one of my fantasies. Great story hope there is chapter two

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