Chapter 3: Another New Experience

I couldn't wait for the week to pass. I was desperately hoping that Judy was going to initiate me into all the mysteries of sex that I had been trying to decipher on my own. I thought about abstaining from masturbation that week, to preserve my strength. I also considered continuing to jack off as normal, so I wouldn't have such a hair-trigger. I compromised by limiting myself to just one time, Thursday night, just to take the edge off. I didn't need any of my pinup pals that night. My head was full of images of Judy.

I couldn't sleep Friday night, and I arrived at Judy's house early. I wanted to get whatever chores she had for me done as soon as I could, so we would have more play time. That week she wanted me to clean out the gutters, and help her clear out some of her husband's stuff from the garage. She was in a very businesslike mood, no smiles or greetings, as if what had happened last week had all been in my imagination. After I finished dragging the last of the trash from the garage out to the curb for pickup, she invited me in for lunch again.

I went in with a smile on my face, and ate the sandwich she had fixed as fast as I could, not that easy, since in was peanut butter and jelly. This time she didn't stay in the kitchen while I ate, so when I finished I called out to her. I guess I was kind of expecting her to come back in some slinky nightgown, or maybe even nude, and to lead me back to her bedroom, but instead she just yelled at me from wherever she was in the house that she would see me again next week.

Now I was really confused. What was going on? Had I really been dreaming last week? No, there was no doubt, the images were burned into my memory; she had exposed her breasts, and jacked me off. My seed had splashed on her linoleum, and she had licked my ejaculate from her hand. Had she lost control of herself that day, and now felt so bad that she didn't even want to see me? If that was true, why wouldn't she just tell me to quit showing up, that my debt was paid? It was obvious that females were still very mysterious to me.

The next week I showed up with low expectations. Just do your penance and go home, I had decided. But there was yet another side of Judy waiting for me that day. She met me at the door, smiling and acting like she was very glad to see me. It was time to cut the grass again, and trim the big hedges lining her backyard. She brought me a drink while I was chopping away at the shrubbery, and started asking me more questions while I worked. This time the questions were not about my sex life, but were more normal. 'What do your parents do?', 'Do you have any brothers or sisters?', that kind of thing.

By the time I finished the chores I was a mess, sweaty and dirty. Judy looked at me and said, "I've got a special lunch for you today, but you need to get cleaned up first. Come on in, young man, and go straight to the bathroom and take a shower." I followed her through the house to the bathroom, feeling very much like a twelve-year-old being cared for by a babysitter. "Here," she handed me a robe, "Throw your clothes out after you take them off. I'll rinse them out and run them through the dryer while you are eating. You don't want to put those stinky things back on after you shower do you?" Now she was beginning to sound like my mom, which kind of freaked me out.

I knew the robe had to be Sam's, and it felt kind of strange putting it on. He was a lot bigger than I was. I looked at myself in the mirror, the sleeves hung down to my fingertips, and the bottom almost dragged the floor, I felt even more like a little boy than I had before. I cinched up the belt as best I could over the overlapping folds of terrycloth and reluctantly walked back to the kitchen.

Judy hadn't been kidding when she had said she had a nice lunch. Grilled cheese, with sprinkles of powdered sugar, and what looked like home-made chocolate chip cookies. She had put some thought and effort into this lunch instead of just throwing some lunch meat between slices of bread. She sat across the table from me as I ate, and continued the inquisitive questioning she had begun in the yard. It seemed like she wanted to know everything about me. I asked if I could have a drink, and she got up to pour a glass of milk, apologizing that she had forgotten it before. When she brought it back to the table, she didn't sit back down. Instead she stood behind me and started massaging my shoulders and neck.

"You're growing up, Kevin, but in some ways you are still so young. Your shoulders are so narrow and your arms are so skinny. But I know one part of you that is developing quite nicely."

I just sat there, munching on a cookie. The body part she was referring to was beginning to swell, and I did a quick check to make sure that the robe was still secure. It was partially open, and without any underwear on, it would only take a small movement for it to fall open, revealing myself to her gaze. Is that what she wanted? Should I just let it fall open? Did she want to jack me off again, or did she have some other adventure in mind? I couldn't decide, so I just sat there, enjoying the pressure of her hands on my tight shoulders.

After a few moments of very relaxing treatment, she sat down again, this time on the side of the table, much closer to me. She crossed her legs, and as she rocked her raised foot, she started playing with the edge of the robe, teasingly, as if she were trying to decide whether to lift it up or not.

"Kevin," she asked suddenly, "how old do you think I am?"

Even at fifteen I knew what a dangerous question that was. I took a swig of milk to stall while I tried to think of a good answer. My mom was forty-four, and Judy looked to be much younger than that. But still, from the few times I had seen Sam, I judged him to be in his mid to late fifties, so how young could she be? In those days, it wasn't normal, or 'nice', for younger women to marry guys much older than they were. I decided that thirty would be a nice, safe guess, but at the last second I added a couple of years for reality.

"I don't know, maybe thirty-two?"

She smiled at me, and I felt immediate relief. "Not bad. You're being nice I know, but I'll accept that as an honest answer. Actually I'm thirty-six. So, am I younger than your mother?"

Talking about my mother with Judy, with me sitting there almost naked and semi-erect, was just one more uncomfortable moment that Judy seemed to delight in causing. "Oh, yes ma'am," I assured her.

"Am I prettier that she is?"

Now that was a totally unfair question. What scale of attractiveness could I use to compare my mom to this fascinating woman, eight years her junior, but who appeared much younger to me, and who had licked my semen off her fingers in this very kitchen.

She laughed at my obvious discomfort. "Never mind, Kev. We shouldn't even be talking about your mother right now. What I really want to talk about is you."

Over the next few minutes she asked me just about every possible question about my experience with girls and sex. I don't know what was more embarrassing, having her ask me those questions, or having to admit to almost no experience with girls, sexual or otherwise.

"Well, now I know why you jack off so much," she giggled, clearly enjoying my discomfort. "I don't know why guys like you are so shy around girls. If only you knew that girls your age are just waiting for guys to talk to them. Hell, when I was your age I was just as curious about sex as you are, and I jumped at the first chance I had to try out some things with my first boyfriend. I don't know if I qualified as a slut or not, but by the time I graduated high school I had had sex with six different guys, and not all of them were students. I guess my sex drive has always been a little on the high side."