Scouting Rounds a Guy Out - Cover

Scouting Rounds a Guy Out

Copyright© 2021 by elevated_subways

Chapter 11: Hank and Molly’s Hilltop Date

Coming of Age Sex Story: Chapter 11: Hank and Molly’s Hilltop Date - Near a New Jersey camp in the summer of 1969, a young guy meets an older lady who is just as kinky and horny as he is.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   Consensual   Romantic   Heterosexual   Fiction   School   MaleDom   FemaleDom   Spanking   Masturbation   Oral Sex   Petting   Slow  

During my first weeks in high school, I spoke to Molly several times. To avoid having my parents note the name of Alpine on the phone bill – who would I be calling there? – I called her collect from one of the booths in a pharmacy about a block from my building.

She seemed to understand that I wasn’t able to see her as frequently as I had before the school year had started. In fact, I was able to go up to Alpine only once in that period. Maybe I was taking her too much for granted to give her any priority. Perhaps she understood that but she wouldn’t directly admit to it.

In one of my calls she said, “I suppose they’re giving you a lot of homework, I mean compared to a regular school. That’s what I’ve heard, anyway.”

I didn’t find it that onerous, but I exaggerated a bit for the effect. “Oh, yeah, that’s the way those specialized places are.” Actually, Arlene was taking up more of my time, but I wanted to keep that a secret and I needed a way to placate Molly.

Besides, I had always been in the upper classes of the “tracking system” that most New York public schools had back then. Thus, I was already used to doing more than an average amount of homework.

I asked her, “So how are things going at your school this year?” She taught English and history at Northvale High, a town in upper Bergen County. It was a fairly small and upscale community, so she didn’t have to deal with the blackboard jungles that prevailed in the larger, poorer cities.

At one point she said, “I did bring up Woodstock in classes like I said I would.” The festival had taken place a few weeks earlier. “As I had predicted, most of my kids were amazed that I knew so much about it. One of them said, ‘Wow, Mrs. Jacobson, you actually like The Who?’ “ The Who had appeared at the end of the second day and had done more than twice as many songs as any other band or individual.

She continued, “I was pleased, yet it also made me feel kind of old. I’ll be forty in November.” Then she surprised me by saying, “I still don’t know if I’ve done the right or wrong thing, Hank, but having you around makes me feel...”

I knew she was going to say young again, but she didn’t. Instead, after a pause, she said, “Well, it makes me feel like Grace Slick,” which seemed like an amusing way to put it.

I gave her a bit of info that I hoped would make her feel better. “She’s not as young as you might think. She’s going to be thirty at the end of October.”

She chuckled and then she said, “Hank, you would know a detail like that. I certainly didn’t know it! One thing for is for sure, I was never as slender as she is.”

I was too young to know how to be “cool” with a woman, so I reassured her again. “Molly, it doesn’t matter. I know how sexy you really are.”

“Oh, Hank, that is very sweet of you.”

“I must admit, I did notice those photos of girls skinny-dipping in a pond or whatever it was.”

Molly was skeptical. “You mentioned them once before. And as I said, how many of them were there? Like fifteen or so? And 200,000 guys who would have liked to get with them?”

“Maybe I did miss something after all, but I was a bit too young to go.”

“The whole thing was so over-hyped by the media. Like by Walther Cronkite, of all people. A half-million people, and they managed not to attack each other. Not that they knew how to get there efficiently either.”

I joshed, “Molly, you’re becoming cynical in your later years.”

“Perhaps, but America doesn’t just go to the poorhouse in an automobile, it goes to the Revolution in them too.”

“So what should they have used? Bicycles?”

“That would have worked if they were so concerned about nature. But how many people over the age of sixteen even owns one?”

A bit later she said, “I’d really like you to come up here soon. I haven’t seen you much since the school year started.”

“All right, we’ll have to figure out a time that will work for us.” What I meant was it would have to be something that would work for me. I’d have to get up there and back in a single day, and I usually only had the two days of a weekend as options.

I added, “You know that my family is moving to the North Bronx at the end of October.”

Molly was aware that the trip over to the bus station in Washington Heights was going to be much longer and more complicated than it had been. It would require taking two long and slow rides on city buses to accomplish. Then I still had to take the Red and Tan line up Route 9W to her house.

“Okay, then call me when you think you’re ready.” She sounded neutral about the issue, and I didn’t find anything suspicious about her statement. I was too inexperienced to realize that bringing up the travel problems was a mistake that no woman would want to hear about.

After we hung up, a thought about something else struck me that I had trouble acknowledging: I was cheating on her by becoming involved with Arlene. I’ve been acting like a real cad.

Arlene had known about Molly since that first Friday I had a conversation with her. She never seemed to mind. If anything, the experience I had in New Jersey increased my appeal to her. Of course, she assumed that my Alpine partner was another teenager, not a mature woman. Thus, I had been lying to Arlene too.

After the first couple of days, I decided not to mention Molly again, and Arlene had not inquired about her. It seemed advisable to never even mention my camping story in New Jersey.

I was dealing with some very adult-level complications and yet I had little idea of how to handle the situation. Events seemed to be taking on a momentum of their own. I had tried to rationalize it by thinking that any young guy would have done the same as I had if offered that much sexual opportunity. Yet I couldn’t shake the idea that I was treating both women unfairly.

Perhaps I had been too sexually successful before I could handle it emotionally. Both Molly and Arlene had been what my parents would have called “fast” or “hot numbers” back in the late 1940’s and early ‘50’s. Actually, I’m sure that they would have been dismayed by what Molly had done with me and blamed her, and they probably would have blamed me for being “reckless” with Arlene.

Of course, I wasn’t going to do what my parents thought I should. But I didn’t even grasp how naïve I was, and I just grabbed what I thought was my share of what everybody else seemed to be doing.

Molly had her own distinctive set of charms, and I missed her plump body and her experienced way of handling me sexually. Yet I procrastinated about calling her and looking for an invitation from her. There seemed to be no rush. Scouting was in the past now, and I became distracted by my new school, new girlfriend, and getting ready to move to my new neighborhood.

I had ignored the fact that I hadn’t seen Molly in person since the first school weekend in September. However, I had called her just to keep her in the loop.


Molly didn’t ignore me, however. Thus it was surprising when called me one Thursday in October. I had forgotten that I had given her my home phone number at some point; I assumed that it was just something that she should have available for some undefined contingency. She contacted me after four in the afternoon when she knew I’d likely be home from school.

Of course, one of my parents, my mother, answered it. She said a Mrs. Jacobson, a guidance counselor from my school, wanted to speak to me. On the face of it, that didn’t make much sense. Why couldn’t she just have me come to her office during regular hours? Also, why would I need guidance just a few weeks into my freshmen year?

People I guess are generally trusting – or maybe just gullible – when hearing such a request from an authority figure. Molly had long experience working in schools, and she probably could fake an official-sounding phone voice.

I knew I’d have to be careful about being overhead on my end of the conversation. To start with, I said, “Hello, Mrs. Jacobson; this is Hank.”

“Hank, I need to talk to you in person.” She sounded like her usual self, and I couldn’t detect any hint about what she wanted. Yet the unusual nature and timing of the call confused me and I got the first sense that something was wrong.

“When would you like me to come in?” I knew that I would also be told where to go, namely Alpine. For a moment, I hoped that Molly was going to resolve the situation by finally bringing me to her house, but I was wrong about that.

She said, “To make it easier for you, I’ll come into the city – I mean Washington Heights – to meet you. There’s this diner called the Hilltop Restaurant at 181st and Fort Washington.” That was only about two blocks from the bridge exit. “How does Saturday afternoon sound?”

I made up a time that would be within school hours on a regular day. “I can do two P.M. if that works for you.”

“That’s fine. I’ll meet you outside the place and then we’ll talk over a light meal of some kind.”

It was very tempting to ask, What exactly is this about? but I knew it was not the best moment to say that. I hoped my mother would probably forget that a Mrs. Jacobson had ever briefly called me, or I could make up a plausible cover story if necessary.

I was inexperienced with women which made me uneasy, but I tried not to dwell on it. My intuition told me that Molly was going to mention my lack of any recent interest in her. However, what she might do about it eluded me. All I knew was that my situation didn’t seem so idyllic now.


By that time it was mid-October and I had been dating or fooling around with or whatever you want to call it with Arlene for about six weeks. By coincidence, we had agreed to meet to go downtown on that Sunday. By then I would know what Molly was concerned about.

The Hilltop diner was on the first floor of an old apartment building, a common set-up in city neighborhoods. I arrived early because I knew it was on a street corner and that there would be no place for us to sit. Molly was there a few minutes later, and she was wearing slacks and a jacket. Because of our usual caution, we didn’t hug each other. It was notable that she didn’t smile at me, but she simply said, “Let’s go inside and get a booth.”

Once in there, we quickly ordered and then I gave Molly the first word. It’s her “date,” let her reveal the point behind it. She didn’t waste any time. “Let me get right to it. So, Hank, you must have met a girl at your school, I assume.”

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