Chapter 4: The Big Day At Last

Three weeks! It might as well have been three years, or three lifetimes. I couldn't wait that long to see Judy again. She meant everything to me now. She wasn't just Mrs. Martin, the business woman who had given me a break. She was more than a widow that I did chores for and who fixed me lunch. Now she was my sweet Judy, my first sex partner and teacher, and the first woman I had ever felt affection for. All I could think about was the things she had done to me, and what I hoped we would do in the future. By today's standards, those two simple sex acts might seem inconsequential, but to a shy young boy, growing up in the early 60's they were life-altering experiences.

And I was hoping that the best was yet to come. I still hadn't even seen her pussy (or any pussy for that matter), and I was pretty sure that I was going to get laid the next time we met. It might have been fun so far to just see my reactions, but from what she had told me about herself, I knew she was a highly-sexed woman who needed some sex in her life, and she had selected me to be her relief valve.

September 21. That was the Saturday I would see Judy again. I didn't just count the days, I counted the hours. As the day slowly grew closer I began to fret more and more about what might happen, and what I should do to prepare. Did Judy expect me to know what the correct positions were, and what to do, or would she show me everything? Was she expecting me to buy condoms? Did I have enough confidence to walk into a drugstore and do that, or would I have to rely on my shoplifting skills again? What if I came too fast? It hadn't taken her long to get me off with her hands and mouth. Could I possibly last longer than two minutes in a pussy for the first time? I decided that frequent masturbation would solve that problem, so I beat off almost every night for those three weeks. I stopped three days before the big day, just to make sure my dick wouldn't look too bad. I was putting the abuse in self-abuse.

Finally it was the 21^st. I gave up trying to sleep at 5:00 a.m., and just lay awake for the next three hours, trying to overcome my nervousness. I got to her house half-an-hour earlier than usual, and started pacing up and down on the sidewalk to burn up some of the time. I didn't want to knock on the door and seem like some desperate, overeager kid, even though that's what I was.

I must have looked like a soldier on guard duty, marching back and forth in front of her house. After I had been pacing for about ten minutes, Judy cracked open the door and stuck her head out. "Kevin," she almost shouted, "get in here before the neighbors call the cops. What's the matter with you? What are you doing here so early?"

"I'm sorry, Judy," I sputtered. "I've missed you so much that I just couldn't wait to see you." Damn, that came out all wrong. I sounded like the love-sick teenager I was trying not to be.

She grinned, and I knew I was OK. I followed her into the living room. If there had been any doubt about which 'Judy' would be there that morning, the fact that she was still wearing her nightgown seemed to answer that. IT didn't look like any chores were going to get done that day. It wasn't the kind of nightgown my mom might have worn; it was silky and pink and short, and as she swayed in front of me I wanted very much to run my hands up under it and caress her ass. One of the things I had decided during my three-week sabbatical was that I was going to be more aggressive in our relationship. I didn't want to just wait for her to lead me along like a little boy. Squeezing her butt might have been just such a move, but before I could work up the courage to try it, she walked into the kitchen and poured two cups of coffee. I don't know why we always seemed to end up in her kitchen. Even today, I sometimes get randy when my wife and I are in the kitchen together on a Saturday morning. I've never explained to her the reason for that.

We stood there, somewhat awkwardly, sipping the warm beverage. I didn't even like coffee in those days, but I wasn't about to tell her that. Adults drank coffee, and I didn't want to do anything that would make me seem young to her. I needed for her to see me as an equal, a lover, and not a young boy she would feel ashamed about being with. I let my eyes wander slowly over her body under the satiny wrap, wishing she would just untie the sash around her waist and put an end to the suspense. Or should I? Wasn't this what a confident, in-control lover would do?

"So you missed me, huh?" Her tone was almost mocking.

"Yes ma'am," I admitted, feeling myself blushing again. Damn, I hated that.

"Kevin, I think the time has come in our relationship for you to stop calling me ma'am. It just makes me feel old. You don't think of me as old, do you?"

"No, ma... no, Judy. I think of you as a very sexy woman, and the best thing that has ever happened to me." God, where was all this coming from? I couldn't seem to stop myself from babbling and saying ridiculous, childish things. But she had said we had a 'relationship'. Didn't that mean something?

She stopped smiling and got a very serious expression on her face. Had I gone too far, too fast? "Look, Kevin, don't get too wrapped up in yourself. This is just kind of a game to me, teaching a kid about sex. Don't take it too seriously."

"Judy, I think it's only fair that if you want me to stop calling you ma'am, you should stop calling me kid. OK?"

"Your right, of course," she laughed. "Even though you have the face of a twelve-year-old, your cock says you are a man, and I should treat you like one." As she said that, she made one of my dreams come true by untying the sash and letting her robe fall open.

Judy was nude beneath the silk, and I suspected it wasn't because she hadn't had time to dress because I had arrived so early. The gleam in her eye was a giveaway that she had been looking forward to this day as much as I had. My heart thudded as my eyes tried to take in every inch of her body at once. I had seen her breasts before, of course, but somehow I hadn't noticed the light sprinkling of freckles that started at her shoulders and cascaded down her chest, ending in a V between her smallish but intriguing tits. For the first time I was aware that her eraser-brow nipples stood out prominently from the surrounding areolas. Her left breast turned to the side instead of facing straight out, ruining the artistic ideal of symmetry, but lending a feeling of reality to her appearance. This was the way real people look, untouched by the tricks of photographic editing and lighting.

My gaze lowered to her belly, and I noticed that it was tight and trim, like a teenager. Somehow I had assumed that everyone over thirty had at least some extra body fat, but Judy had kept herself in fine shape. Her hips flared out, giving her a classic hourglass figure that was just as appealing as most of the fantasy images I usually masturbated to. My gaze finally fell to a surprisingly large patch of curly light-brown hair protecting her intimate parts. None of the magazines being published in those days dared show pubic hair, so that was a bit of a shock. But my unfulfilled curiosity about the feminine mystery hidden among those curls overcame any unease I may have had about touching the triangle of light curls that disappeared between her thighs like an arrow pointing the way to paradise.

After silently letting me just stare at her in admiration for a few moments, Judy finally broke the silence. "Kevin," she whispered, "would you like to make love to me?"

I stood there staring at her. I'm sure my expression must have been funny, but she was kind enough not to laugh. "Come on, baby," she said softly, "let Judy show you what you have been missing."

She took my hand and led me to the bedroom. OK, she was still leading me around like a little kid, but at that moment I didn't mind a bit. As we walked down the hall, all the doubts and uncertainties that had been troubling me over the last few weeks vanished. I just relaxed and let her lead the way. Any attempt at assertiveness could come later.

Judy dropped her robe on the floor and sat down on the bed. I stumbled around, trying to get my clothes off like they were on fire, almost forgetting to take my shoes off before my jeans. Once I managed to strip off my Jockey's, she reached out and grasped my dick, using it like a handle to pull me toward the bed. One last bit of uncertainty arose then; should I just get between her legs and... what? Start fucking? Or should we make out a little first? I knew I was ready, hard as a rock, with a few drops of precum already wetting her fingers, but I wasn't sure if she was ready. Relax, I told myself, your with an expert, let her show you the way.

I sat down next to her, and we kissed. This was my first real kiss. When her lips first pressed against mine, my mouth was tightly shut, like accepting a thank-you kiss from a maiden aunt. When Judy's tongue pushed against my lips, I opened my mouth and accepted her. The feeling of her tongue pushing against mine was interesting, if not particularly exciting. I pushed back, and felt her almost sucking my tongue into her mouth like she had sucked my cock before. That was more exciting.

Without thinking, my hand came up and cupped her breast. I let my fingers squeeze it a little bit, and she groaned. So that's a good thing when making out, I made a mental note. Her nipple was just as hard as it pressed against my palm as it looked, and I started playing with it. I tweaked it and pushed it and tickled it, and she didn't seem to mind any of that, from the way she continued to probe my mouth with her tongue and make soft noises, almost like a purring cat. I moved my hand to her other breast, the independent one that turned out, and continued my explorations. That one seemed to be just as sensitive, and felt just as good, as the other one.

A few seconds later, Judy lay back on the bed and pulled me down alongside her. Our mouths finally separated, and she pushed my head down toward her breasts. I took her hint and began sucking on one of those hard nipples. I slowly opened my mouth and gradually sucked almost all of her breast in between my lips, while I continued to tickle the tip with my tongue.

Judy took my hand and guided it between her legs. She didn't say anything, letting her hand show mine what to do by example. She pressed one of her fingers into her slit, and I let my index finger follow. We moved our fingers together, slowly stroking from top to bottom, just barely between her pussy lips. Her dampness there was another surprise. I had no experience with the natural process of female lubrication. At first I wanted to pull my hand away, not sure of what I was feeling, but Judy seemed to be enjoying what I was doing so I kept moving my finger in tandem with hers. The more we stroked, the wetter she got, and I realized that it was a natural reaction to what I was doing. She pulled her hand away, and I continued stimulating her on my own, having learned what she wanted.