Math Tutor

I was 20 years old, in my third year of an undergraduate math major at a small college. I was 5'11", average looking, light brown hair, brown eyes, with pretty bad acne. The name "Glenn" suited me since it was sort of nerdy with a dated style. There were very early signs of my hairline starting to recede, which I was really embarrassed about. I liked to stay in shape by riding my bike a lot, and working out in the gym, but despite my best efforts I was skinny and was never able to put on much muscle. So I never had good self-esteem about my looks. I always wanted a girlfriend, but could never work up the nerve to even talk to a girl at all, much less ask someone out. I was cripplingly shy, but I never had the insight to actually work on my social skills. So I was lonely and tended to wallow in it rather than do much about it.

That year I decided to do a little bit of math tutoring, to earn a few dollars and to try something new, maybe to bolster up my CV.

My first client was a woman named Cathy, who was a 4th year arts student taking an intro calculus course, to get her mandatory science credit before she graduated.

Our first meeting was at the college cafeteria, off to the side during a quieter part of day. She showed up exactly on time. I was a little nervous and awkward, saying hello and shaking her hand. She was in her early 30s, average height, short curly light brown hair. This was not my favourite look-- this style reminded me of one of my aunts -- I'm much more a fan of long, silky straight hair. She was slim and seemed fit but not athletic, with an average figure. She had feminine, small, soft hands and short nails, which I did like. I often associate short, healthy fingernails with sensitivity, humility, intelligence, and sensuality--for example a musician or a masseuse needs to have short nails, and a good student would have a hard time writing or typing fast with the long nails that so many girls like. I thought long nails were also a sign of vanity and superficiality. Cathy had a bit of downy hair on her forearms which I didn't much like, and her skin was a little bit freckly or pasty, also not my favourite. The one and only outstanding feature about her appearance was big blue eyes, all the more special because she didn't need glasses. A bright, rich blue, almost violet. Her eyes looked sensitive and intelligent and calm and observant, even more noticeable because the rest of her face and body were so ordinary otherwise. Her teeth were healthy and straight, and she had a nice gentle natural calm smile, but her lips were thin, a little bit freckly, pale, and not very sensual.

So overall I never had any kind of sexual thought about Cathy, since she seemed plain-looking except for her strikingly beautiful eyes, and there was a 15 year age gap. At the time I really was attracted only to girls around my age. When I found out that she had two young children, I totally saw her more like I would see an aunt rather than a friend or potential romantic partner.

While she was an arts student, with no background in math, I thought her math skills were very good. She was careful and neat and diligent with her work, always did all her homework on time, even doing extra problems. She wanted a tutor because she was worried about her grades, after she did poorly on her first exam.

We had a nice rapport, and she was polite and grateful for our tutoring sessions at the cafeteria. I learned that lived in a small house with her two young children, ages 3 and 5. Her neighbourhood was very close to the rough area of town, with inexpensive very small homes typically owned by hard-working blue collar families. I thought maybe she inherited the house, or maybe she had a husband who helped buy it, since she hadn't been working regularly over the past years. She was finishing a degree at the college to help her find a better job. Near the end of the term, she said "Glenn, as part of thanking you for your help, I'd like to invite you for dinner this Friday." I was surprised by this offer, and a little nervous since it was a little bit different from the professional norms I'd had with other tutoring students. But it was probably going to be the last I saw of Cathy, since she was finishing her course, and she had been a really good student, putting in great work. She was poised to get an A in the course, and by this point she didn't really need tutoring anymore. I think she continued because she enjoyed the sessions. Also I knew she didn't have much money, raising two kids with limited income, so I felt a little badly about taking my tutoring fee from her.

I still lived in the basement of my parents' house at the time. Before I left for my dinner my mom seemed anxious, as though it was inappropriate for me to have dinner at a client's house. I reassured her as I climbed into my parents' car which I was borrowing for the evening.

When I arrived I was sort of looking forward to meeting Cathy's kids, but when I got inside, they were nowhere to be found. Cathy was dressed up a little bit, in an elegant outfit that was unusual for her. When I asked about her kids she seemed to frown a bit, as though she didn't like my question, before telling me that they had gone upstairs with her good friend, Maria, who was babysitting. The kids were already asleep. She explained that her friend was a 35 year-old woman from the Philippines, and was probably asleep already herself--Maria had been exhausted lately, getting ready for her wedding, which was coming up in just 2 weeks. It was Maria's first marriage; she apparently had a lot of trouble finding a man because she was very shy and not very good-looking, and also wanted to focus on school and work. Cathy added that we would have to be careful not to make too much noise and wake them up.

She seated me at a small dining room table while she finished up in the kitchen. It smelled wonderful in there. She had made-herb seasoned chicken breast with a nice salad and vegetables. I have to admit that it was absolutely delicious, and I even asked for another helping of chicken. She laughed, and commented about men's big appetites.

After dinner, she poured us both small glasses of wine. I was a little uncomfortable with this, since I was a non-drinker, and also I was driving home. But I knew it would be just a small glass, and I didn't want to seem impolite. She gestured for us to move over to her small living room, where there was a couch and coffee table. Once I sat down, she excused herself to the washroom for a couple of minutes.

On the side table next to the couch I noticed some formal-looking papers. I could tell they were probably legal documents, and there were signatures or initials at the bottom of each page. The font size was quite large, so it was easy to read from a few feet away. I didn't want to pry into her private stuff, but I couldn't help but notice that the papers were a formal confirmation of a divorce. Cathy was officially divorced, and the date of the signatures was just a week ago. I wondered why she had left these important papers exposed in her living room with a guest over. I had a little wave of anxiety that she might have left those papers there deliberately for me to see, to signal that she was "available," but I swept away that thought as being ridiculous. I was just her tutor--she obviously liked me and was thankful for my help, but she was 15 years older with 2 kids, and I was barely past being a pimply teenager, so there was no way she had any other thoughts about me.

Next to the legal documents there was another paper with a medical symbol on the top, also dated from a few days ago. It was from a medical lab. As a math guy I'm always attracted to a sheet of data, so I couldn't help but glance down at her lab results. There wasn't much there in terms of a blood cell count or anything like that, but it showed results of an STI screen -- all negative. I thought it was super weird that she would have such a private document exposed in her living room.

When she got back, we talked for a couple of minutes, then she asked me, "so, would you like to watch a movie?"

I was a little bit surprised...I thought this was just a dinner. I said "well, I've got to be getting back home...I have to study and then I have an early start tomorrow too." This was true, but I was also wanting to get out of there because despite the awesome meal I was feeling anxious that Cathy might have the wrong idea about me.

She looked quite disappointed. "Well, let's just have some dessert before you go...it's time to get it out of the oven...".

It was a delicious apple crumble, one of my favourite things. And she had some ice cream with it. After we munched on our dessert together, she reached over to take my plate, but while leaning over the coffee table she seemed oddly clumsy and her torso knocked over the bottle of wine that she left open. It poured all over me...it was red wine, and my shirt and pants had huge stains. A little bit got on her clothes too as she rushed to clean up. We were both embarrassed, and she apologied over and over. A little corner of my mind wondered whether she had deliberately spilled the wine.

I knew my mom would have big questions for me if I came home with wine-stained clothes, when she was already worried about this dinner.

Cathy said: "Glenn, I can quickly wash and dry your clothes while you're here...it'll take just about an hour and a half...but we should get the first load going right away, before those wine stains set."

I reluctantly agreed. "Laundry is just upstairs" she said. "But we have to be really quiet...the kids and Maria are asleep" she whispered.

Upstairs, she ushered me into a little dimly-lit room that had some tables and a long rectangular table with what seemed to be a hole in one end, and some linens covering it. There was a shelf with what looked like heavy blankets. There was an alcove in the room, just off to the side, with a small cot on which someone was softly sleeping. I assumed this was Maria, Cathy's friend who was babysitting. There was a small Japanese screen dividing the alcove from the rest of the room, allowing a little bit of privacy but still having some gaps so you could see and hear what was happening on the other side.

"You can change in here," Cathy said. "Just leave your clothes outside the door...then you can hide under those blankets on my massage table." She smiled meekly; "maybe I can give you a short therapeutic massage while we wait. I took classes to become an RMT last year, but I never did go further with it...too busy with the kids. Usually you're supposed to lie on your front, but right now you have to lie on your back, because that donut thing on the massage table is broken right now, and you can't lie face-down until I get it fixed."

The room smelled nice. I never had a therapeutic massage before. I was a little nervous about Cathy's motives, but she was so nice...and also there was another adult sleeping right next to us, with sleeping kids in the next room, so there wouldn't be any risk of anything inappropriate.

When Cathy returned, I was already underneath the massage table blanket, which was very heavy. It was scented with some kind of massage oil which made me feel relaxed and a little bit more comfortable. My clothes were in the washing machine. I was a little bit sleepy, and I was getting into the idea of resting for an hour or two before heading home.

Cathy was wearing a silk robe, having changed out of her own wine-stained clothes. She had bare feet which made a delicate feminine patter on the floor as she walked. She dimmed the lights a little bit and explained how she would use a little bit of massage oil. She would only be able to massage my arms and legs, because I was lying on my back. I didn't have any clothes on, but she sensed my anxiety about this and reassured me that I would be covered up completely except for the arm or leg that she would be massaging.

She brought several more heavy scented blankets, explaining that the weight and the pressure was a calming part of the massage experience, which had been used in other areas of health care such as helping autistic kids settle down. The blankets were so heavy that I couldn't really move my limbs or torso. Yet I was comfortable, feeling safe and snug and warm.

I really enjoyed the massage. Cathy squirted oil onto her hands, using a special pump, every minute or so, as she slowly moved around the table to get to different areas of my limbs. I especially liked my hands getting massaged. I felt more and more relaxed.

Cathy had placed a soft, warm towel over my face, so that I couldn't see clearly. As she was massaging my limbs I could hear the soft sounds of her hands on my skin, and of her soft footsteps and clothes rustling against the floor and the table. When she finished all four limbs there was a pause.

I heard a slight swishing or rustling sound and a very slight muffled thud on the floor. I thought maybe she had dropped one of the towels.

She removed the towel from my head so that I could see more clearly. What I saw made me gasp with sudden fear, and I tried to get up off the massage table. But the weighted blankets were too heavy, and I was pinned down.

Cathy was naked. She had dropped her robe onto the floor. She had full breasts, which were only slightly droopy. The areolas were large and had a deep pigment, a sign of a woman who had breast fed her babies. The nipples were unusually prominent, like soft erasers poking out about a centimeter from the areola. She was slim. Skin a bit freckly and pale but very feminine and silky soft. Downy pale blonde hair in a few spots on her trunk and her forearms. But legs totally hairless. Her belly was slim but soft and protruding a little bit, typical of a woman who's had a few pregnancies. Her deep blue eyes peered into mine, and seemed an even deeper blue than before. I had never seen a woman's body up close.

In a soft, gentle, matter-of-fact voice she said "We're going to fuck now. I've wanted this ever since I first met you."

I was very anxious...now full of dread and nearing panic since I felt trapped under the blankets on the table. I didn't want sex. I hadn't thought of her sexually. She was too old. I wasn't ready for sex. I wanted a girlfriend my age. I was a virgin. And I was scared of sex...I wanted to wait until I met someone special, and probably to wait until marriage, just like my mom wanted for me. I knew my mom would be horrified to know what was going on here. And it was risky too.

She pulled aside and folded the weighted blankets so that they restrained my arms and legs, with most of the blankets' contact area around my elbows and knees, leaving the rest of my body exposed. I was trembling with anxiety. She climbed on top of me and supported herself on her hands and knees, so that our bodies were not yet touching. I could feel the warmth radiating from her body, including from her dangling breasts. Her breasts gently rocked back and forth; even though I didn't know much about a woman's body, I could tell that her breasts had been sucked on a lot over the past few years--I couldn't help referring to biology class, that this was the purpose and destiny of all female mammals, an evolved trait that first appeared 180 million years ago. These breasts had a lineage that represented care and success for our species since before the age of the dinosaurs. The heat from her groin warmed the corresponding area of my body underneath.

Her face came close to mine and she started kissing me, as I turned my face back and forth like a frightened animal straining to get away.

My cock was flaccid due to fear. Cathy squirted a different kind of massage oil on herself, letting it drip down her torso and her breasts, drizzling down her belly. Then she leaned forward and massaged my torso with hers, her nipples soft little fingers of flesh helping with the massage. She whispered close up to my face, and into my ear, "Glenn...it's ok...we don't have to do anything you don't want... we can just stop after cuddling for a few more minutes..." then she licked my face and my neck and continued softly rubbing her oily body on mine, with her legs and feet joining in to massage my legs and feet. Her breasts massaging me were like fleshy warm water balloons, with her nipples sticking out and rubbing me like tiny soft fingers. She would pause to rest her whole body weight on mine.

After about 10 minutes I began to relax. She was so gentle with me, with reassuring soothing words...and I felt that she would give up in a few minutes since my cock was still soft and flaccid...

All this time her body had not yet touched my cock. She had respected that at least. But as she kissed me on the lips and probed my mouth with her tongue, peering into my brown eyes with her deep blue eyes, as my initial fear and anxiety settled down, my cock started to harden. In about five minutes it was very very hard. We were both aware of this and it made me very anxious, about what might happen next.

She whispered in my ear, "it's time."

My eyes widened with anxiety and I shook my head...I tried to think of something to say to reason with her.

I spoke for the first time since this incident in the massage room began; my voice almost squeaked out, stuttering, tremulous and barely audible. I was also conscious of not wanting to wake up the kids in the next room, or Maria who was sleeping right next to us in the alcove. "Cathy...what about protection?...I want to be safe."

Cathy responded, "of course Greg... safety is very important to me...have you ever seen a condom before?"

I was relieved that she was bringing up condoms. But I had never actually used one. I was a virgin. I got in trouble at home for staining my sheets after masturbating last month, so I was thinking of trying to masturbate with a condom, but I hadn't actually tried one yet. In the meantime, I hadn't had an orgasm in about 3 weeks, and my balls were actually painfully sore and heavy...I just tried to shut out any kind of sexual thought.

Cathy reached over, and pulled out a condom that she had stored in a little box on the side table. "I've been hoping for this for the past few months, so I'm pretty well-prepared, Glenn.".

She kneeled back over my legs, and gently rolled the condom onto my very hard cock, explaining what she was doing at each step.

"This way we'll be safe" she said.

I didn't want to have sex but I was at least relieved that it would be safe, that I didn't have to worry about Cathy getting pregnant. Imagine a 20 year old virgin getting a 35 year old mother of two pregnant...it would ruin my life...and think of what my mother would say!

Cathy kneeled over me and gradually lowered herself onto my cock. The tip of my cock was pressing against her vaginal opening. It was warm and I imagined almost steaming with her fluids and secretions. I could smell massage oil mixed with sweat mixed with something completely new, that I had never smelled before, the secretions of an aroused woman.

Cathy took her time in this position, gently kissing me before moving any further.

Then she paused, and went back up on her knees. "I'm glad you know how to use a condom, Glenn...but we won't be using one today." She slowly rolled the condom back off my cock, and set the unrolled condom back onto the side table.

I was back to a sudden state of fear and panic...as she lowered her body onto mine, my cock sinking deep into her cunt.

The massage oil Cathy used on Glenn's limbs had a medicinal effect: it was absorbed directly through the skin, and interacted with receptors in the spinal cord to inhibit orgasm...it didn't affect arousal or stimulation, it just prevented orgasm. She had found this oil in a herbalist's shop in Indonesia, during a visit to see her former in-law's family. Once the oil was absorbed, it would prolong and intensify sex because of inhibiting orgasm, while still allowing sexual tension and the urge to cum to build and build. It was the perfect accompaniment for sex with inexperienced, anxious virgin guys, a group notorious for premature ejaculation--cumming five seconds ever entering a woman's vagina. The oil's effect would last about a half hour, and then gradually fade and disappear over the next few minutes.