Sometimes Crime Does Pay - Cover

Sometimes Crime Does Pay

Copyright© 2007 by TheDarkKnight

Chapter 5: All Good Things...

Erotica Sex Story: Chapter 5: All Good Things... - 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  

We developed a routine over the next few weeks. I would hurry over and do whatever little chores she had for me, then take a quick shower. When I emerged, sometimes with Pete's robe on, and sometimes nude, she would be waiting for me in the bedroom, and my education would continue.

She introduced me to several positions; doggy, spoon, standing with her bent over in front of me, and even once with her sitting on the kitchen counter. That one was a little tough because I wasn't quite tall enough, and it ended in laughter before we came to our senses and retreated to the bedroom.

She attempted to teach me how to orally please a woman, but I wasn't ready for anything that sophisticated. I went through the motions, but didn't really enjoy it, and when she realized my discomfort she gave up on the idea. A few years later I had a girlfriend who insisted that I go down on her before sex, and that's when I learned to enjoy cunnilingus, but with Judy it was a disaster.

I knew our time together couldn't last forever, but it still took me by surprise when she told me one day about three months after our affair started that she was moving away. "I've sold the store, and I'm going to put this house on the market. I'm going to go back home for awhile, until I can figure out what I want to do with the rest of my life."

I had no idea she had even been thinking about doing that. We really never talked much, other than sex talk. The idea that she could just leave like that hit me like a slap across the face. I couldn't help myself, I felt tears welling up in my eyes, and before I could stop them I felt the warm drops cascading down my cheeks. I hated crying in front of her, it made me feel like a kid again. But the way she had made her announcement, so suddenly and coldly, had hurt me. I felt like I was losing my first lover, not just my sex teacher.

She took me in my arms and tried to comfort me. "Kev, you're going to be fine. You're a good looking kid. You've got a nice cock, and thanks to me, now you know what to do with it. You know what women like, and how to please them. You're a patient and considerate lover, which means you better than ninety percent of the other guys out there. There's no need for you to be shy around girls anymore. Heck, you probably know more about sex now than any of your friends. So go on with the rest of your life with more self-confidence. Don't worry, getting girls will be easy now. We seem to have some kind of radar that helps us find the nice guys. And now that's you, Kevin."

She was right about that. My shyness around girls was completely gone. Heck, there wasn't anything mysterious or scary about them now. From then on I was able to have normal conversations with girls my age without blushing or having my underarms soaked with perspiration. It was still another year or so before I had sex again, but when it happened I was ready, and both I and my girlfriend enjoyed it, thanks to Judy's lessons.

She had one more surprise for me before she left. As I was leaving her house for the last time, she handed me a key and told me it was to a post office box that she had taken out in my name. She told me to check it regularly. I didn't know what was up with that, and for awhile I wondered if she would use it to send me love letters. I checked it every day, but nothing showed up. After a few weeks of disappointing emptiness, one day I found a large envelope stuffed in it. When I opened it, the latest edition of Playboy was inside. There was also an envelope from the publishers informing me that a "Mrs. Judy Martin" had purchased a two-year gift subscription in my name. I kept renewing that subscription for several years after that, and each time I thought about my beautiful, sexy, intriguing "older woman", Judy.

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