Scouting Rounds a Guy Out - Cover

Scouting Rounds a Guy Out

Copyright© 2021 by elevated_subways

Chapter 8: Hank and Arlene

Coming of Age Sex Story: Chapter 8: Hank and Arlene - 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  

In the previous chapter, Hank had set up a date with Arlene, a girl at his new school, who he has only known for five days. This is in September 1969.

Classes let out at 3:00 PM, so I had more than two hours before I was due to meet Arlene. I decided to walk part of the way over to Pelham Parkway. After an hour, I had reached Fordham Road at Third Avenue, which was about half the distance I needed to go. I decided to sit on a bench at a nearby park for a while.

Why does this girl need all this time before she meets me? Maybe she’s eating dinner with her family and she only wants a soda or something. Perhaps I should have asked her, but that had never occurred to me.

With a combination of sitting, more walking, and finally getting on the bus, I was over to White Plains Road about fifteen minutes early. Now I had to decide whether to meet her early, be right on time, or be a little late. I had no experience to guide me in such social situations. I settled on being about five minutes late.

Arlene was already standing in front of the diner and as soon as I saw her I got an idea of why she needed the extra time. She had changed her clothes for one thing. Now she had a short-sleeved blouse, a skirt, and chunky sandals on. And the shirt – it was a bit on the short side. She had no stockings, and I looked at her bare calves and part of her thighs.

In addition, she had made some effort to get her hair into order.

She did all this for me? So what I’m I supposed to say to her? Molly had not prepared me for every contingency. I was suddenly concerned that Arlene would be miffed if I didn’t comment on her appearance at all. If I had been older I probably would have known that it was best not to mention it, or at least wait to be asked about her looks.

I went with, “Hi Arlene. Have you had dinner yet, I mean with your family?”

“No, I intended to eat here with you.” Then she grabbed her skirt and swished it around. “So, what do you think? You know what I mean.”

“You certainly look different.”

She was slightly amused by that. “Oh yeah, I’m different all right.”

Then I saw a slight “tell,” I guess that would be the correct term for it. I don’t think she intended to do it, but I saw her briefly lick her lips.

I tried to deal with the thoughts flooding my head. Is this Arlene coming on to me? It certainly seemed like she was. Then I flashed to Molly. Oh man, the sweet fucking I’ve done with her.

Then Arlene came back into focus. I didn’t even know her yet, but I could see myself putting my hands under her skirt and yanking her panties off. Yeah, baby, I know just how to make you come. And I wouldn’t even have to use my cock; I could do it with my mouth. You’d like that, wouldn’t you?

It only took a couple of seconds to think all of that, and I was rattled by my own imagination. We’re both way too young to even consider doing such things. With Molly, it was different somehow; she was an adult, and I instinctively trusted her no matter what she did with me.

I gestured towards the door. “So, let’s go in already.”

As I scanned a menu, I decided on something easy to chew – tuna salad. When I glanced up, I saw Arlene looking at me, assessing me perhaps. She wasn’t smiling, however. I thought, I really would like to go up to Alpine and see Molly this weekend.

For about three minutes Arlene and I talked about school topics. We hadn’t attended the place long enough to have much to say. Then, as if reading my mind, she asked, “So when are you seeing this Molly girl again?”

I tried to be casual but I was having trouble with that. “I’m not sure. Didn’t I say it was hard to get together with her?”

“But you’d like to be with her, I bet.”

“So you do believe me, I see.” Immediately I thought that was the wrong thing to say.

Arlene said, “Maybe; I’m still trying to figure out how much is true and how much you simply made up.”

I was feeling uncomfortable with her; I wasn’t sure if I could trust her. Then I remembered, just act like it doesn’t matter. Let it roll off your back. In a moment, I found myself reconsidering my own advice to myself. She said, “So, Hank, what did you think when you saw me in a skirt?”

I was used to being polite to people, especially ones I didn’t know very well. Then I decided, don’t be too extreme, but be provocative and see what happens. I glanced at the menu again and I said, “Oh, I was wondering what kind of panties you’re wearing.”

She laughed at that. “You’re such a dirty boy, you know that?”

“And you’re a pretty dirty girl yourself.” Did I really say that?

“Yeah, and you’ll find out how much, I think. I’ll show them to you – I mean my panties later.”

“You don’t mean here?” Wow, that was a dumb thing to say.

“No, of course not. I meant in my building, in one of the stairwells.”

This girl is far too young to be so bold. I wondered if she still has stuffed animals in her bedroom. Molly hadn’t truly prepared me for this, although she had said that a lot had changed since her own girlhood. She taught high school, so she had seen much of it first-hand. What would Molly advise me about getting out of this situation?

Yet I was excited too. Arlene was going way beyond flirting. A little hand-holding and kissing would have been appropriate, but she seemed to be skipping that stage. Unless, perhaps, it was all a tease.

I tried directness again, although it came out sounding more like doubt. “Arlene, so what do you expect from me?”

“You’ll find out, soon enough. I admit I don’t know even know myself yet.”


Inside the lobby of her building, I wondered if she was going to take me to her apartment and introduce me to her family. Yet she had already suggested otherwise, although it wasn’t going to happen in a stairwell. “Let’s take the elevator to six and then we’ll go up on the roof.”

For some reason, I said, “Why, can you the Empire State Building from up there?”

She was amused by that, “Among other things, yes. ‘I see London, I see France, I see Arlene’s underpants.’ “ Am I imagining it, or is her laugh more like a cackle?

In those days, most rooftop doors in apartment buildings were not locked. Of course, it was an easy gateway for burglars using the roof to access the fire escape ladders along the back of the building. Yet the practice continued at many buildings for at least another a decade.

When we stepped out of the stairwell at the roof level, there was still full daylight left. I went to the wall at the front of the building and looked to the left. Even though there were other roofs on either side of me, I could see the New York skyline to the south as I had expected.

After a few moments, I realized that Arlene was not with me. I looked behind me; she was a few feet back. “You know why we’re up there; I already told you.” Then she raised her skirt and I could see her panties. They were fairly ordinary cotton ones, I guess, and they were blue with white polka dots.

She turned around and flashed the rear view for me. Just as she dropped her skirt, I heard, “So do you do like my pretty little panties?”

It seemed best to make light of it. “You’re quite a little tease, aren’t you?”

“Oh no, I’m not a tease. Come over here and you’ll find that out.”

It struck me that maybe she wasn’t completely aware of what she was doing. Don’t mess with me, baby, because you might get more than you bargained for.

But I was wrong about that too. She laughed and skipped towards the back of the building. I thought, she’s indeed playing a little game with me. Yet I followed her anyway.

I found her standing behind the motor room at the top of the elevator shaft. And I was sure why she had gone there. The view from the stairwell door was blocked if someone came through it. But then, we wouldn’t be able to see them either.

She wasn’t smiling, but she was giving me a strangely intense look. “I know what you want to do.”

“And what would that be?”

She raised her skirt again and said, “You want to touch me, that’s what.” Then she sneered, “But you don’t have the nerve for that, do you?”

Some conflicting thoughts were going through my mind. Don’t go near her; get off this roof. But I was getting an erection while looking at her, and I also thought, go head, she had started this when she talked to you in the classroom. And then she started asking about your sexual experiences. That had been only a few hours earlier.

I shouldn’t have bragged about those experiences, but I foolishly had done just that. Molly would have said that I had acted impulsively. On the roof, I said, “Oh, I have the nerve, for sure.” Without really thinking about it, I stepped right in front of her.

I tried to gauge her expression. Arlene’s mouth was open a bit and she was gazing directly into my eyes. But of course, the most noticeable aspect of her was that she was still holding her skirt up.

There is something very wrong with this girl. For a moment I wished we had simply gone to the school cafeteria a couple of times, started the whole affair at a much lower key.

Touch me could mean any number of things, so I improvised an action for myself. It was simple; I put my right hand through a leg opening in her panties, and I started rubbing, then squeezing her behind.

Arlene didn’t swat my arm or step back; she certainly could have done one of those things. Instead, she said, “oh;” then she put her hands on my shoulders and pressed her body against mine. When she looked down, she giggled and said, “I can see I’m quite an effect on you.”

“Well, of course you are.” She couldn’t have possibly ever done something like this before with another guy, right?

Then she softly said to me, “Go ahead, move your hand to the front, I want that.”

Probably I wouldn’t have tried that if she hadn’t given me explicit permission to do so. My hand went into the crotch of her panties and my fingers touched her pubic hair. Then I used one finger to gently rub her slit. Her genitals felt much like Molly’s did.

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