The Usual Disclaimer: This is a work of fantasy. All characters featured in sexual situations are over 18. The characters in these stories are fictional. Any resemblance to actual persons living, dead or undead is purely coincidental. Do not try this at home.
*****
I felt genuinely bad about what I had done. I felt like I was an awful person, an awful son. I had taken advantage of my own mother, and wished that I could somehow take it back. I lay in my bed and thought back over the events of the past three weeks, before going further back in time. In my mind, I was trying to pinpoint that one moment when I had stepped over the line. There had to have been a point in time, I reasoned, that this could have been stopped before it went too far.
Through the thin walls of our apartment, I could hear my mother sobbing in her own room, and that just made me feel worse. Mom was my life! How could I have done such a thing?
* * *
My name is Tommy. My parents got divorced when I was five years old. Dad remarried a couple of years later, and I have three younger half-sisters from that marriage. However, Dad and Clarissa (his new wife) moved away when I was seven, and I have barely seen them since. For the past fifteen years, it has just been me and Mom.
Oh, she dated other guys after the divorce, particularly for the first five or six years. Two of those guys, Gary and Paul, were particularly memorable because they actually lived with us for several months each. Eventually, they moved on. I never thought to ask why. Whenever my mother broke up with the guy she had been dating, she would spend a lot more time with me.
When she was with me, my mother never moped or cried about the relationship that had ended. Instead, she just seemed happy to spend more time with her son. At that young age, I just liked having all of that undivided attention. I had no clue about sex whatsoever. I certainly didn't think of my mom as a sexually active or attractive woman.
She dated less frequently as I got older. By the time I graduated high school, I could not recall the last time she had gone out on a real date with a man. She and I went out at least once a month, dressing up and going to a restaurant and sometimes to a movie. We got into a bowling league when I was a junior in high school. The two of us became fairly good bowlers and we made some friendships that have lasted ever since.
It was sometime during one of our weekend bowling matches that I became aware that my mother was an attractive woman. She had always just been 'Mom' in my mind, in a completely different part of my brain than where I kept 'hot women.' On that evening, she was wearing a pair of slacks under her league shirt that were a bit more snug than usual. My mother went up to get her bowling ball, and when she bent over her ass was pointed right at those of us seated behind her.
Honestly, I had not been paying attention to her until Greg, the guy sitting next to me, let out an excited breath. Now, Greg was a guy in his mid-twenties who was a bit of a hound when it came to women. He was constantly making little inappropriate comments about any attractive woman who caught his eye. Usually, he was quiet enough about it that only those of us near him could hear it. I had learned to follow his gaze whenever Greg had one of his outbursts, though, because there was usually a very attractive woman in a provocative pose at the receiving end of those lustful looks.
In this case, I found my eyes following Greg's gaze to a very attractive woman's bottom in tight blue slacks. When she stood up, I was shocked to see that it was my own mother. I had started to get hard before she stood up, and was embarrassed that my arousal did not go away even when I knew who it was.
It felt like I had somehow crossed some wires inside my brain—the part that was perpetually turned on by a sexy woman had somehow gotten locked onto my mother as a sex object.
From that point on, it only got worse. I began to notice other little things about Mom that had never stood out to me before, but all of them only made her sexier. I had to wonder how I had lived under the same roof for so long without taking note that she never wore a bra around the house. She had the most mouth-watering, thick nipples I have ever seen, and they were practically on display all the time.
Mom worked as a secretary, and her work outfits were definitely sexy. She wore nylons and skirts every day, and she took care of her feet and toes so that they looked delectable in her open-toed heels and pumps. The blouses she wore emphasized the gentle curve of her breasts. I had to imagine that guys were always coming on to her at work, and I had just never realized it.
My mother also had a very rich, sexy voice. Her throaty laugh was undeniably arousing, once I became aware of it. I started telling her more jokes my senior year of high school—even some that seemed terribly inappropriate. As long as I told the joke well, I was rewarded with one of her boner-inspiring laughs.
It became a constant source of embarrassment to me, how often I was completely aroused around my mother. I had my own car, and I began to spend more time away from home just so that Mom would not catch me staring at her with a rampant erection in my pants. As a result, I often spent hours just hanging out at the local mall. Eventually, that led to my first job.
There was a massage booth under the escalators. I use the term 'booth,' but that isn't really accurate. There were four massage chairs, designed so that you would sit in them basically backwards. Your face would be at this hole where the headrest of a normal chair would be, and your back would be facing outward so that the masseuse could work on you. The area was partially shielded by a pair of curtains from passersby.
I had started hanging out around that area because there was a cute girl who worked there. She was in my school, and I had flirted with her a bit. The guy who ran the business was a legitimate masseur named Don. He was in his early thirties, and looked really buff. Danni, the girl I had been flirting with, was shy and not very talkative. Don, on the other hand, was very outgoing and he started talking with me. He offered to train me and offered me a job if I was any good. I was caught off-guard when he leaned in and whispered to me.
"Tommy," he said, looking around, "if you learn to give a decent massage, women will be lining up to ask you out."
I had seen some of the gorgeous women who regularly came in for massages, so I readily agreed. It turned out that I had a knack for it. Both Don and Danni said I had "good hands" and was "a natural" at finding and relieving knotted muscles and pinched nerves. I spent three weeks of intensive training with Don, coming in after school every day and spending another ten to twelve hours each weekend. Halfway through the third week, Don had me practicing on customers who came in while he supervised.
I was delighted to get my first paycheck. My mother was happy for me, but she was troubled and I could tell.
"What's wrong, Mom?" I asked.
"Oh, it's nothing," she answered with a shake of her head, "it's just that I had no idea you were doing this, Tommy. I feel like I got left out of a major part of your life this past month. Really, though, congratulations! I am very happy for you."
She gave me a big hug and sighed into my ear. I had to hold my hips back from her so that I didn't poke her with my hard dick.
* * *
Now, I'm not going to pretend that every one of the customers I gave a massage was some hot chick, because that was definitely not the case. There were a lot more women than men who stopped in for a massage, but I got comfortable with giving guys a massage when they requested me. Most of them wanted Danni to put her hands on them, of course. Still, I did have some regular male customers just because I gave a very good massage.
There were a lot of regular customers who were middle-aged housewives. Some of them were very attractive, and flirted with me and Don whenever they came in. Naively, I thought that it was just innocent flirting. I was there for five or six months before I caught on that Don was having sex with a lot of these women.
By that time, I had graduated high school and the part-time job at the mall had become full time. Don often left me in charge of the mall massage business while he left to provide a customer with a massage in their home. He very delicately explained how that part of the business worked. Mostly, he was filling me in on how the billing was different and how to manage my tips and pay taxes on those if I ever gave a customer a home massage.
It went completely over my head at that time that he was explaining how to charge and pay taxes if I ever had sex with a customer for money.
I gave three home massages—legitimate, just plain massages—before Don took me aside and explained that at least one of those women had been disappointed with the service I provided.
"What did I do wrong?" I asked naively.
"It was what you didn't do that had her disappointed," he said. Seeing the look on my face, he let out a sigh. "This isn't a discussion we can have here. Can you come to my apartment after work?"
"Sure," I said.
That evening, I got an eye-opening education on how Don really made his money. Oh, he was an excellent masseuse, but most of his income came from sexually satisfying dozens of frustrated older women around town. Now, at that point I was no virgin, but I wasn't some stud either.
"I don't know if I can do that," I told him honestly. "It's not like I have been with a lot of women. I know I can give a really good massage, but I'm pretty sure I would just disappoint these women if they expect me to give them some amazing sexual experience. I'm not built like you are, Don."
That was true; I was just an average guy in every respect. I had strong hands, and my forearms were muscular from all the massages I had given, but I wasn't otherwise remarkable.
"Well, we'll have to fix that," Don said.
Over the next three months, I practically lived with the guy. He had Danni hold down the fort at work, and he took me with him to several 'home massage' sessions with a handful of his regular customers. These women really got off on having me watch while Don serviced them. He kept up a running dialogue while he pleasured them, pointing out dozens of helpful tips to make me better at pleasing women.
