Chapter 1: Meeting Molly

I believe that “Scouting Rounds a Guy Out” was the Boy Scout advertising slogan at the end of my time in the organization, which was the summer of 1969 when I was fourteen.

Two things were going on then. One was that my troop was in decline because of demographic changes in The Bronx. The second was that I was going to enter high school in the fall and Scouting was beginning to seem very uncool. I wasn’t sure it was worth transferring to another troop further from my home. My troop, what was left of it, was going to be merged into that one.

But, yes, I certainly did get rounded out that summer in a way that was not part of the official Scouting program.

The previous year we had gone for two weeks of summer camp at Ten Mile River. That was up in Sullivan County, New York, on the banks of the Delaware River. The next year the remnants of Troop 213 went to Camp Alpine in Northern New Jersey, which was much closer to the city.

By coincidence up there in Sullivan, the Woodstock Festival was going to be held in the county in August of ‘69. The Yasgur’s Farm site was very close to the border with the Ten Mile River camp. Later, I would look at the famous photos of the skinny-dipping girls in whatever ponds or lakes existed up there.

Of course, 99% of the males at the festival probably didn’t get any poontang from the few chicks who doffed their clothes and splashed around in the water. That didn’t bother me, because by then I had something much more serious – sexually, I mean - to be concerned about.

Our troop was rather disorganized by that point, and we all had several hours of free time to deal with each day. I just walked around the camp, which was pretty big but nowhere near the huge acreage up at the Ten Mile River site.

My summer scouting uniform consisted of a short-sleeved shirt, shorts, khaki knee socks (held up with some kind of garters around the knees, if one can picture that), and hiking boots. Sometimes I wore a green cap I had picked up at a Jamboree the year before. Of course, around my neck was the red scarf or neckerchief or whatever that thing was called. One can understand why I was reluctant to walk around Bronx streets with that get-up on.

Alpine, NJ, however, was a pretty upscale place although it did have some more modest houses just beyond the southern border. One day, after about three days, I wandered out onto the street on that side and I was walking past the wood-frame houses on those blocks.

I walked by somebody, a woman who was just standing there leaning on her wooden fence in front of a house. To my teenage eyes she seemed – well, not quite old, but certainly mature. She could have been one of my teachers, I suppose. She was actually thirty-nine, but I had no idea at that time about how to judge her age.

My idea was just to walk past her, but she said something to me just as I was passing her. “So, how is the Scouting thing going over there?”

It seemed best to just reply, “Pretty good, I guess,” and then keep walking. But something made me slow almost to a stop. Perhaps it would have been rude just to keep going. Or maybe I subconsciously got some hint about her personality and what she would want from me. Some instinct told me that she was looking for more than mere conversation.

She must have noticed my confusion because she laughed and said, “Why don’t you sit with me on the porch? We can chat a bit. Would you like some coffee?”

“Ah, I don’t drink coffee.”

“All right, have some soda then.” I was still rooted to my spot, so she crooked a finger at me. “Come on, don’t be shy.” I was getting a sense of friendliness about her, or maybe something more than that, so I went up and sat on a bench on the porch. She went inside and came back with sodas for both of us. Then she plotzed down right next to me.

“I’m Molly Jacobson. I teach high school in Northvale, but of course, I have the summer off.”

I tried to be as polite as possible, and I introduced myself, “Well, I’m Henry D’Amato or just Hank.” I found it necessary to add, “I’ve been in the Scouts for two years now.”

“You’re not in a hurry to get anywhere, are you? Hang out with me for a while.” She added, “By the way, there is no Mister Jacobson around. I’ve been divorced for a couple of years now.”

I assessed who I was dealing with. I wasn’t used to having conversations with females of any age, beyond my own relatives. This Molly person would have gone unnoticed by me had I passed her on a street in the city. She wasn’t beautiful, but neither was she homely. Now, however, she was right next to me and I was very aware of her, well, femaleness.

Had it been a male trying to talk to me, I would have said a quick goodbye and kept going. Or had I been older and more experienced, I would have recognized that she was trying some pick-up lines on me.

She was of middling height. Her dark hair was cut on the short side, and she had glasses with black frames. There was something appealing about her face even if she wasn’t young and gorgeous.

Her body was on the chunky side, but her thickness was not excessive. She was wearing a pullover blouse with an intricate design, a lot of boxes and lines that were mostly tan, black, red, and white. The sleeves came down just below her elbows, and I could glimpse half of a small tattoo on her left arm.

Beyond that, she had a denim skirt that came down just above her knees and dark sandals. The longer I was with her, the more I got the impression that she seemed like an ordinary woman on the surface but that was misleading. For one thing, I noticed her intelligence.

She was easy to talk to, and we sat there for a little while discussing our lives. I was surprised that she knew at least a bit about my neighborhood in The Bronx, Morris Heights. My experiences in Scouting also came up as a topic.

During this conversation, she got up to get some wine for herself. When she came back, she didn’t have a wine glass, but a water tumbler filled with white wine. My impression was that she was uneasy about something and she needed the alcohol to get her nerve up for it.

I found that out what it was soon enough. She had gone through about half of the glass when she said, “Hank, do you mind if I ask you a personal question – a very personal question?” If she hadn’t been a woman, I would have simply refused to answer. But I was suddenly thinking that some interesting things were about to happen, although I didn’t know what those might be yet.

She hesitated; I could see that she was nervous. “This is a little hard to say, but what the hell – I’m going to do it anyway.” There was another pause, and then I heard, “Hank, you’re a young guy; do you masturbate a lot?”

That got my attention immediately. I could feel my face getting warm and I knew I was blushing. My first thought was, this old dame wants to talk dirty with me. The whole topic was so taboo that I was shocked. And yet I was also excited by her boldness. The only references to sex I had ever heard before were from guys my own age.

“I’m sorry, I didn’t mean to make you feel uncomfortable.” Well, she was making me uncomfortable but I was unexpectedly excited too.

The odd thing was that my Boy Scout handbook, the 1965 edition, managed to mention masturbation without ever using the word. For a moment, to give myself a moment to think, I remembered what was in it. In the last section at the back, The Scouting Trail to Citizenship, there were a few paragraphs under the heading, “From Boy to Man.” In that, there was a brief discussion of nocturnal emissions, or “wet dreams.”

There are boys who do not let nature have its own way with them but cause emissions themselves. This may do no physical harm but it may cause them to worry. Any real boy knows that anything that causes him to worry should be avoided or overcome.

Well, I definitely caused emissions myself. I still thought I was a “real boy,” however that was defined. Yet, based on that passage, I had given up beating off for about four days. Then I thought, this is ridiculous. I don’t have to do what that book tells me to do. I went back to masturbating so much that I didn’t even have wet dreams. I certainly wasn’t going to tell my parents, physician, or spiritual advisor about it. Hey doc, I’ve been whacking off a lot. Is that normal?

As young as I was, I knew Molly hadn’t asked that question out of mere curiosity. I grasped that her query was likely going to lead to further actions between us. Has this lady ever been laid since her divorce? What I underestimated was how extensive her plans for me would be.

She was looking at me with s very serious expression. I imagined that she was thinking, did I overdo that? Is he just going to leave?

As for myself, I didn’t want to miss whatever opportunities she was going to offer me. Older ladies had to have an ulterior motive for asking young guys about their sexual habits. I pulled together an attitude of manly indifference. I answered, “Sure, I do it a lot, like every night if I can.” I almost added, what did you expect?

She must have thought through all of the steps, even though she was tense about it. “Well, I know it’s hard.” (Pun intended?) “But you’re been a very bad boy and you deserve to be punished, by me I mean.”

“And when is that going to happen?”

“Right now, inside my living room. I’m going take you over my knees and give you a good hard spanking on your bare behind.”

Even at the age of fourteen, I didn’t take that at face value. I understood a couple of things. The first was that she was going to do it to satisfy her own kinky needs. The second was that it would likely be followed by something more sexual, obviously involving me.

I admit that it was exciting to imagine that lady looking at my uncovered behind while her hand beat my bare flesh. Somewhere deep inside my mind, I had my own kinky desires I rarely talked about. Well, the previous spring some dirty magazines had been surreptitiously passed around by my fellow Scouts.

A few of these publications were English spanking magazines, some of which showed dominant women – displeased teachers, bosses, aunts, and others - whacking away at the naughty asses of their male students and such. I was fascinated to see those pictures, although I tried to remain a bit aloof when commenting on the photos or line drawings.

One of my fellow troopers claimed to have direct experience in these matters, and he related how he always got an erection whenever his aunt spanked him for some misbehavior. Of course, he said he always got it on his bare behind. He further stated that his aunt took pity on him afterwards and she would then let him masturbate to orgasm as she watched.

I wasn’t sure I believed him. Having a bunch of horny young guys in one place could result in a lot of erotic tales, some of which might have an element of truth and others of which could be complete fantasies. Underneath our chaste-looking Scout uniforms, our male hormones were ruling our bodies.

I decided to play along with my new female acquaintance and I said, “All right, Molly, if you think it is for the best, then I will submit to your spanking.” I thought she’d mention something about her high school students, but she didn’t. She simply stood up and said, “Come with me.”

What would follow this punishment? I would soon find out.

In her living room, she sat on the sofa and she was quite abrupt as she said, “Just stand in front of me.” She unbuckled my shorts and removed them; then my underpants were next. Both garments were simply left on the floor. Being bottomless in front of a lady, even an older one, instantly gave me a huge erection.

Molly pretended not to notice, although she had to see it. She patted her lap and said, “Just put yourself over my knees. And keep your feet on the floor.”

When I was in position, it was delightful to have my bare crotch pushing against her lap. She put her left hand on my back and she lifted her right hand above me. “Are you ready to take your discipline?”

“Yes, Molly, I’m ready for it.”

She was a hard spanker, and she took her time with it. It hurt, but yet I was enjoying it too. I made noises and clenched my buttocks. My hips rolled on her lap. “I know it hurts a bit, but try to stay in position.”

At one point I looked back at her, and I saw her concentrating on the task at hand. She’s enjoying this too. Somehow having my shoes, socks, and garters still on added to the frisson of the experience. My erection rubbed against her denim skirt. I liked the feeling of her hands on my body, one holding me and the other hitting the exposed flesh of my buttocks.

Molly said a few things like, “Young man, I hope this teaches you a lesson about how to behave in the future. Unfortunately, I have to tan your behind but good.” When she was done, she rubbed my bare ass, which felt wonderful.

“Oh my, you’re so warm, I believe you actually enjoyed it, you naughty boy.”

Why deny it? “Yes, Molly, I did like it in a way.”

“Don’t be surprised, a lot of guys like to be spanked by a lady.” So she admitted the truth about what she was doing. “Now, there is one final step to this. Stand up and bend over the end of the couch.” When I was in place, she pulled out a wooden stick from behind the furniture. It was too thin to be a true cane. Nevertheless, I suspected that this was going to sting.

I asked, “Are you really going to use that thing on me?”

“Yes, Hank, I’m going to give you six of the best, as they say in England.” At that point in my life, I was unfamiliar with the supposed English predilection for corporal punishment. “Don’t worry too much, I’m not going to use full force, I’m just going to rap you with it. Now put your butt up and out and take your punishment.”

Her first whack caught me across both butt cheeks. It seemed like more than a mere “rap.” I stood up straight and yelled.

“Come on, Hank, it wasn’t that bad; take it like a man. Try to stay in place. You can grip the sofa tighter if you have to.”

“Molly, this a bit much, don’t you think?” Man, this lady seems a bit weird.

“Don’t worry, I’ll make it worth your while when I’m done.”

I wanted to know what that would be, but I hoped whatever it was would result in an orgasm on my part. Just being over her lap and getting spanked had brought me halfway there. As I stood there, I looked back at her and she winked at me. She had better come up with something good, or I’m out of here.

Even jerking myself off while she watched would have been good enough at that point. Anyway, I probably controlled myself a bit better with the next five strokes, but it wasn’t easy. Amazingly, my cock stayed upright even while I was being hit with the stick. I was learning how kinky I was.

After the six whacks were completed, Molly said. “Okay, we’re done. You may rub your backside; that should comfort you a bit.” I didn’t need any further encouragement to do that. “Now, stand against the wall with your hands on your head. I want to examine my handiwork.” She had brought her wine in and she sat in an armchair and looked at me.

I dared to turn a bit to see her. She seemed, frankly, a bit shaky. After a short while, she stood up and came over to me. Her hands went along the parts of my body that hadn’t been struck. She rubbed my back under my shirt, then she caressed my thighs.

When she was behind me, she softly said, “Young men have such taut, sweet backsides, plus such nice cocks. I know you’d like to put it deep into some chick, but I doubt you’ve done that yet. Now, I can indeed help you with your boner, but you have to do me first.”