Sometimes Crime Does Pay - Cover

Sometimes Crime Does Pay

Copyright© 2007 by TheDarkKnight

Chapter 2: Serving My Time

Erotica Sex Story: Chapter 2: Serving My Time - In 1960 I was a sex-obsessed fifteen-year-old, with an addiction to the glossy pinup magazines of those pre-internet days. I turned to shoplifting as a way of meeting my needs. When I got caught, the owner of the store, a recently widowed lady in her thirties, didn't know what to do with me. Eventually she came up with a unique way for me to pay for my crimes. At the same time she found a way to fulfill the needs of a horny teenaged boy and a young widow with an overactive libido.

Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa   Teenagers   Consensual   Heterosexual   First   Oral Sex   Masturbation   Petting  

Saturday morning I showed up fifteen minutes early. If Mrs. Martin was giving me a break, I wanted to take full advantage of it. I would have replaced the roof on her house if she had asked. Instead, she led me to the garage and pointed me to the lawn mower. It was just a push mower; power mowers were still rare in those days, so it took me an hour or so to cut the grass. She then asked me to trim some shrubbery in the back yard. By the time I finished it was almost eleven.

When I finished, Mrs. Martin was waiting at the back door. She opened it and invited me into the kitchen. I was surprised to see that she had fixed me a lunch. I had no idea why she was being nice to me, but I was kind of hungry. She cleaned up the kitchen while I sat at the kitchen table, eating the bologna sandwich and chips she had fixed for me. She was wearing shorts and an oversized T-shirt, and with her blonde hair in a ponytail could almost have passed for a college coed. Miss November came to mind.

After I finished, I thanked her and started to leave. "Next Saturday, same time OK, Mrs. Martin?" I asked.

"Sure, Kevin," she said, smiling at me. "I have a lot more stuff for you to do. And it's going to take you quite a while to work off your debt. But you did good work today, so I think this will work out well for both of us."

"Yes ma'am," I smiled back at her, and reached out to shake her hand. It seemed like a business-like, grown-up thing to do. "I enjoyed helping you. It didn't feel like punishment at all."

"Why don't you call me Judy? Mrs. Martin makes me feel like an old lady." She held my hand in hers, and I felt a fingernail lightly stroking my palm. I had no idea how stimulating that one small gesture could be. It tickled, but in a very good way. I wasn't sure if it had been an accident, or if she had meant to do it, but when I glanced at her face I knew it had been intentional.

I had never had a woman, or girl for that matter, look at me with so much interest. Today, I would say she was looking at me with bedroom eyes, but at fifteen all I knew was that something very interesting was happening. Part of me wanted to run off, like a little boy. But I had made up my mind to face my punishment like a man, so I stayed, staring back at my new friend Judy as she continued to hold my hand and tickle my palm.

When she finally released my hand, it was like breaking a spell. I nervously started shuffling toward the door. I was halfway across the kitchen when I heard her say, "Kevin." She said it kind of slow, and drawn out, and I read a lot into that one word.

"Yes ma'am?"

"Don't run off. There's something I'd like to talk to you about. Do you have a few minutes?"

"Sure." I tried to give her my most sophisticated, leading-man smile. I was aiming for the look of a young Cary Grant, but from the way my latest school picture looked, I probably came across more like Howdy Doody.

"Sit down, Kevin," she invited as she scooted one of the kitchen chairs out from under the table. She slid it so that it was in the middle of the floor, not close to the table or anything else. I thought that was kind of weird, but I sat down as instructed. She stood in front of me, arms folded under her breasts, almost as if to bring them to my attention. From her posture it looked like I was going to get a lecture on my bad behavior. She had one of those I-am-really-upset-with-you looks on her face. But as I braced for a tongue-lashing, she suddenly asked "Kevin, how often do you masturbate?"

That was not a question I was expecting. I remembered how uninhibited she had been in her office, but I was still shocked that she would ask me that. I felt my face turning bright red again. My eyes were focused on the floor in front of me, looking for a hole I could crawl into, but I could sense that she was still staring at me, waiting for an answer. "Maybe three or four times a week," I finally managed to stammer, deciding once again that honesty was the best policy.

"Do you always use the girlie books you steal?"

"No ma'am. Sometimes I think about girls from school." Where had that admission come from? I knew I should just answer her questions as directly as I could, but my urge to confess was bubbling up again. I felt like telling her everything.

"What about grown women? Do you ever fantasize about any of them?"

"Yeah, sometimes. Ones I've seen on TV mostly."

"What about real women? Someone you actually know, for instance. Like me."

"No!" I protested. It just seemed wrong.

"You don't think I'm attractive?"

"No ma'am... I mean yes, you are very attractive."

"Kevin, do you sometimes get erections just from looking at pretty girls?"

I had given up staring at the floor, and dared making eye contact now. "Sure, that's just natural, isn't it?"

"Of course it is, Kevin. And it's good that you know that. Am I attractive enough to make you hard?" As she said that, Judy stripped off her shirt. She was wearing a bra, but even the sight of her tightly secured breasts had the effect she was looking for. I felt my cock starting to fill. She paused for a second, almost as if she were unsure if she were doing the right thing, then reached around and unclasped her bra.

Then there they were, two feet away from me, the first set of real tits I had laid my eyes on. Not some glossy picture, but real flesh and blood. They weren't as big as most of the ones I had seen in Playboy, and I could still see the red marks from where the brassiere had been, but to my fifteen-year-old eyes, they were magic. Her nipples were small, but inviting. I didn't know if she wanted me to reach out and touch them, so I just sat there, staring. By now there was no doubt, I was in a state of full arousal. And Judy knew it. "Let me see your penis, Kevin," she said in a soft voice that was more of a plea than an order.

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