Scouting Rounds a Guy Out - Cover

Scouting Rounds a Guy Out

Copyright© 2021 by elevated_subways

Chapter 3: Hank Becomes a Man

Coming of Age Sex Story: Chapter 3: Hank Becomes a Man - 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  

The relationship between young Hank and thirty-nine-year-old Molly reaches its inevitable peak. This is in July 1969.

Over the next week, I went to Molly’s house for five of the seven days. Usually, we’d have some sex play first using our hands and mouths on each other. Then we’d hang out for a while and listen to albums, and twice we saw movies on TV. She would sit pressed up against me and put an arm around me. I loved how affectionate she was.

I began to get adjusted to our unusual affair. Having no previous experience with girls my own age, I let her take charge of the relationship. Yet I was subtly changing too although I didn’t realize the full extent of it yet.

Her tastes in film and music surprised me. Instead of a chick flick, one of the movies we saw was Hell in the Pacific, with Lee Marvin and Tishiro Mifune. It was about an American soldier and a Japanese one who are stranded on a Pacific island together, and how they make compromises to survive together even though they had been enemies.

When it was over, Molly said, “I usually teach history at the school, and I’m always struck by how the kids there don’t give a damn about anything before they can remember it personally, and even there not so much. Some of them are not that keen on any subject.”

I said, “You must remember World War II then. I admit, to me, it seems like a long time ago.”

“Sure, I was eleven when Pearl Harbor happened. I was going to say, both Lee Marvin and Tishiro Mifune actually were in their respective militaries during the war.”

“Really? I didn’t know that.”

“It’s kind of hard to imagine it now, with Vietnam, but back then every male of the right age wanted to be in the service, or at least in the Merchant Marine, which was pretty dangerous in its own right.”

“Oh right, because of the U-boats.”

“And anybody older, if they didn’t have some other job, worked in defense plants. My own dad, who was forty-three at the time, was an engineer at Curtiss-Wright in Wood-Ridge.”

I wondered if he was still alive. He’d only be in this late sixties and what he would think of his daughter seducing a guy more than two decades her junior? But if she didn’t bring up that topic, then I certainly wasn’t going to ask.

Her musical offerings were unusal too. The first album she played was Cream’s Wheels of Fire, and the first song on that was “White Room.” It sounded vaguely familiar to me, but before that day I couldn’t have placed where it came from.

Molly said, “My students say, ‘Mrs. Jacobson, you listen to this stuff, but you’re so old!’”

“My parents listen to some rock.”

“Yes, I think people in, maybe their early forties, are about the oldest cohort to be able to appreciate any of it.”

“It would be incomprehensible to my grandparents, I think.”

“Except some of those old blues singers, they went back pretty far. They were really among the precursors of rock music if you listen to them carefully.”


One day I arrived there and she offered me a glass of wine, the second time she had ever done that, and she had one for herself. She was wearing one of her usual warm weather combinations of a blouse, skirt, and sandals.

“I know I shouldn’t be giving you wine. I could be accused of contributing to the delinquency of a minor.”

That seemed pretty funny, but I couldn’t think of a suitable retort, so I just smiled at her. I remembered how she said once that she could get into a lot of trouble if she was caught with me. She soon went to get more wine for herself but none for me.

After a few minutes, she said something else to me. Her voice seemed tight, so I knew she was a bit nervous. She put one of her hands on my arm.

“Hank, I think this is the day we make a full man out of you.”

“What does that mean?”

“Well, to be crude about it, I’m going to bust your cherry today. You do know what that means?”

I certainly did, but I didn’t want to admit it. “I think I’ve heard it, but I’m not sure what it means.”

“You’re blushing again, so I’m sure you do know.”

“My face always gives me away.”

“Don’t worry, it’s all right that you have a sense of...” She didn’t complete her sentence, but I think she meant to say a sense of shame. “All right, of course I meant you’ve going to lose your virginity, to me, obviously. It’s not like there are any other females around here.”

“But I don’t have any rubbers.”

“That’s okay, I had my tubes tied a long time ago. I didn’t tell you I have a daughter, did I?”

I hadn’t expected that. “No, I’ve never heard about her before.”

“Her name is Veronica, and she’s seventeen.”

I think we then talked about Veronica for a bit so that we could avoid the main issue at hand.

“Where is she now?”

“At her father’s house in South Jersey. She’s not coming back here until later in the month.”

“So I guess I’m not going to be meeting her?”

“I’m sorry, it would be kind of awkward for all of us, as you probably can guess.” Then she thought of something. “It’s ironic, but I wish she would meet a man as good as you are. Of course, you’re much too young for her.”

“Well, I’m not too young for you.” Maybe I was hinting at the legal implications of what Molly was doing.

“I know you’re joshing with me. We’re in an entirely different kind of situation!” I had heard about but hadn’t yet seen the movie The Graduate, and I was briefly reminded of it. Of course, Benjamin Bratton had a good eight years on me, so he was well above the age of consent.

For a moment I considered asking to see a photo of Veronica, but then I thought better of it.

Molly said, “Let’s stop digressing. Look, do you feel nervous about this?”

I admitted the truth, “Well, yeah, a little bit. But Molly, I should admit that I already sort of know how this is all going to go.”

“Okay, how is that?”

“I never told you this before, but in my troop we sometimes pass around these dirty magazines – I mean, they’re sometimes the explicit ones from Europe, not like Penthouse and so forth.”

She waved a finger at me. “Ah, Hank, you’ve been holding out on these details from me.”

Now that I had broached the topic, I felt more talkative. “I mean, they show, like, everything!

“I know, I’ve seen them, although I don’t have any around right now.” She faked a school teacher’s look and voice. “By everything, you of course mean activities like, let’s see – ejaculation, full penetration, even anal sex.”

I suddenly didn’t feel so worldly, and she laughed at my expression. “The one thing I don’t go for is when they show threesomes or even foursomes. I don’t think sex is a team sport.”

I tried to recover some initiative. “I’ve also seen some of those English spanking magazines.”

“Okay, so now I know why you weren’t so surprised when I pulled that off on you. Wow, you Scouts are truly prepared as their motto says, but I shouldn’t be surprised. Did you ever fantasize about having one of your teachers or aunts taking a bad boy like you over her knees?”

That was well beyond anything I had visualized yet. Somewhat sheepishly, I said, “Not really, I mean not yet.”

“But you have already lived it a couple of times, I mean with your friend and neighbor Molly here. I am indeed a teacher, and I know how to handle naughty boys like you.”

A question came to my mind. “Have you ever done that at your school?” That would be Northvale High.

“Oh no, I’d never get away with it, although there are still some states that permit paddling of students. However they have to keep their pants on, I think, which seems takes some of the fun out of it – for both participants.”

I was amazed at what she was talking about. She decided to move things along. “Anyway, we can talk about such matters at another time. Today I will help you so you don’t feel too uncomfortable.” She laughed, “I mean, you don’t have to fumble around with another teenaged virgin. You have an experienced woman here who will tell you exactly what to do.”

I almost said, thank you, but fortunately I held my tongue. She definitely seemed experienced, however.

“Hank, let me tell you the later part of this, the coming attractions as it were. Oh my, no pun was intended! I think, eventually, what’s going to work best is for you to sit on the couch. I’ll get on top, straddle you in other words, and sit on your cock. It’s called a cowgirl. Ever hear that term before?”

“Ah, no.”

Something about her tone of voice hinted that she was a bit anxious too. I supposed she had never been involved with someone as young as I was. But she kept her cool as she explained various facts. “I think it will be easier for you because I can control the motions. Not that you can’t move up while I’m moving down on you.”

I decided to reveal some of my budding expertise. “Oh yeah, I’ve seen that in those magazines, although I didn’t know what they were called.”

“There’s no rush. Come on, let’s make out for a while. I know you like that a lot.”

I was too inexperienced to avoid praising her, “Sure; you’re very affectionate, Molly.”

She seemed to take my naiveté into account and she praised me too. “Oh, that’s very sweet of you.”

She kissed me harder and put her hands on my body more than on previous occasions. At one point she said, “It’s hard not to make this sound clinical. Okay, before intercourse, the two participants have to engage in foreplay.” She giggled, “That did sound very clinical.”

“Maybe you could explain that a bit.” I already half-knew it, but I wanted to hear her explain it.

“What I mean is that the two people have to get each other aroused first. Now let me be blunt with you. Look, I know young guys like you are on a hair-trigger, let’s call it that. Before we have sex, you have to come first – I mean once outside of me. You know all about that from our hand and mouth games. Then for the second one, you’ll have the stamina to really please me.”

That was all news to me. My curiosity got to me, “How do you know about this?”

“Because your Molly here has been around the block a few times. The first boyfriend I ever had, we were both seventeen. He’d come about thirty seconds after going into me. He couldn’t help it. Premature ejaculation is the technical term.”

I was trying to imagine her at that age; it must have been in 1947. She went on, “After this had happened about three times and I wasn’t getting anything out of it, I said, ‘Look, I’ll beat you off first, then we’ll actually do the – ah, penetration.” I think she had been on the verge of saying screwing or even fucking. “And that worked great.”

I had an irrelevant question, “What were you like then?”

“Probably not that different from now. As I told you, I was never a slender girl. But that was okay; guys like girls who are straight with them. I was never a cocktease, in other words. I mean, I didn’t promise more than I intended to deliver.”

I wondered how many guys she had been with, but I didn’t ask that. Instead, I said, “So, if I may ask, how are you going to get me off?”

“Let’s keep it simple. I’ll use my hands on you. But first, hugging and kissing are part of foreplay too.”

This time when she held me, she put her hands under my shirt and rubbed my back. I started to put my hands near her breast.

“That’s it, there’s no one way to do this. You start undressing each other, then you fondle each other. You don’t have to be completely naked at the end, but you could be. It’s a matter of preferences. You’ve had some experience with fondling a lady, of course, namely me.”

She went on, “I can tell by the way you’re touching me that you’re more confident now. You know, I’ve been quite canny with you, bringing you along in stages. Just do what seems right; as I said, do whatever comes naturally.”

During our session, I put my hands under the back of her blouse and tried to undo her bra. I got hung up on the straps. Molly laughed and said, “Guys always have trouble with bras. Here, let me do it. By the way, feeling her boobs is an excellent way to get started.”

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