Chapter 3

Given the real-life events shared in Part One of this series, I really do think I was in a state of shock to find myself in the current situation that I was in.

Here I was, a grown-ass man standing like a silly schoolboy before my nearly sixty-year-old neighbor, Victoria. My hands were locked on my head and my goofy white underwear was at my knees. Did I mention I was still wearing my freaking socks?

With her left fingers pinching the helmet of my cock, Miss Victoria's other hand was pulled back, about to deliver a nasty swat of a wooden ruler directly on my fully erect manhood.

I think the primary thought in my head was WTF! How in the HELL did I get into this situation?

Yet, at the same time, if I am completely honest, a small tingle of anticipation was coursing through me. This was the most weirdly erotic situation that I had ever found myself in. By far!

Now, don't get me wrong. Being dominated and spanked by an older woman, hell, any woman, had never occurred or been a fantasy of mine at any point in my life. Yes, I had engaged in some slight bondage and spanking with previous partners, but it was never anything very serious. And, I was always in nominal charge.

It was quite clear at the moment that I was most definitely NOT in charge.

Suddenly I felt the full impact of the ruler on my cock.

"OH SHIT," I yelled, starting to take my hands off my head and jump back.

But Victoria held the tip of my cock firmly in her hands and didn't let go.

After a few seconds, I calmed down.

Sternly gazing up into my eyes, she asked, "Is there something you are supposed to say?"

Returning her gaze, I hesitantly replied, "Thank you, Miss Victoria."

I know that it sounded more like a question than a statement but it was the best I could do under the somewhat confusing and painful circumstances.

Reflecting for a moment on my confusion, she said, "Do you know why you are having to go through this unpleasant experience, Tommy?"

I replied quicker and with more force, "Honestly, I have no idea."

"It is because you disrespected me tonight and that infuriates me after the kindness I have shown you. We haven't been speaking long but I refuse to be disrespected and I refuse to accept tonight's behavior. I have been around you long enough to know that somebody at some time taught you some manners. I would also venture a strong guess that when you were taught those manners, discipline was used. Am I wrong?" she inquired.

I wanted to yell, "Are you fucking crazy, Old Woman?" but thankfully I bit my tongue and replied, "You are not wrong Miss Victoria, but I have no idea why you keep saying that I was rude to you? I sincerely don't think I was."

"You don't think trying to run out the door when my back was turned, without even saying goodbye or thanking me for the fucking that I just gifted you, was extremely rude behavior?" she dangerously asked.

I was now at a crossroads.

If I responded like I wanted, I knew that the situation could only get worse. However, it is one of the Commandments of Life that bravery quickly dissipates when your cock is firmly in somebody else's hands and that person is upset with you.

So I caved. I may be dumb but I'm not a fucking idiot.

"When you state it like that, Miss Victoria, I guess I was rude to you. I am very sorry," I tried to say in a believable way.

For a few quiet moments, she continued to hold my gaze.

"I am not sure that you are, but you will be before we are done," and with that, she raised the ruler and gave me another swat.

I am not going to act macho and say that this was an enjoyable experience. It was not. But somehow, my cock never softened.

After every blow and a little hopping, I would dutifully say, "Thank you, Miss Victoria," before she would deliver the next.

By the time she delivered her 10th swat, I was quite honestly a quivering, shaking mess. If you have never had your erect cock swatted with a heavy ruler, you might not understand what I am talking about. But I was now a believer. Any sense of ego was long gone. At this point, I was willing to do whatever she wanted.

But even I was not expecting what she said next.

"I know I promised you ten swats on your penis before attacking your backside, but I am not exactly happy with how you took your initial punishment. Too much whining and hopping about," she calmly stated.

My terror index started to raise. This was not going to be good.

Continuing, she said, "I now want you to hold the tip of your penis and pull it straight up while I deliver one final swat to your balls."

Fuck! Fuck! Fuck!

As anyone who has played sports, getting hit in the balls is fucking agony and not something that I would EVER consider erotic. But what was I to do? Disobeying at this point was not an option.

So, grasping my penis, I closed my eyes and dutifully tugged it upwards as she swung the ruler.

Needless to say, I dropped like a rock to the floor. I am not too proud to say I started to cry.

"Now I think I have your attention, young man. Perhaps we are making progress," she said, with a sudden twinkle in her eye.

Of course, I didn't see that twinkle as I was busy rolling around the floor at her feet.

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Chapter 4

After giving me about ten minutes to recover, Victoria told me to quit behaving like a spoiled child and stand up.

After wiping my eyes and gingerly climbing to my feet, I once again stood before her with a tear-stained, completely subservient expression. I have no problem saying that my cock had long since deflated. Getting hit in the balls tends to do that, at least in my experience.

Ever the lofty lady, Victoria said, "Now that I finally have your attention, we will proceed with the second part of your punishment. I am going to give you a minimum of twenty-five slaps on your backside. Go ahead and take off your socks and underwear and position yourself across my legs."

What choice did I have? I pulled off my socks and underwear and placed them on the couch, under her watchful eye. With as much care as possible, I spread myself across her lap. My soft penis went between her legs, which she clamped tightly together.

The only positive part of this experience was that just before I lay across her lap, she pulled up her dress so that I was laying directly on her bare legs. They felt nice.

But what happened next wasn't so nice.

Without further warning, she proceeded to swat the hell out of my ass with that heavy wooden ruler.

It was a rainstorm of painful blows, one after another, as hard as she could swing. I felt like a piece of Jiffy Pop popcorn bouncing on the stove. So much for being a big, grown-ass man. I was now a mewling child at the mercy of his Disciplinarian Goddess.

Although it felt like I received the entire twenty-five blows at once, I think in actuality it was only about ten, because Victoria soon stopped and let me gather my breath. I reached back to try to rub my ass but she quickly put a stop to that with an angry word and a shove in my back.

As soon as my breathing regulated. Victoria coldly asked, "Is there anything you want to say to me right now?"

"Yes, I softly replied, nearly upside down, "I want to express how sorry I am for disrespecting you. It will never happen again."

"Interesting," she said, "But if it does, what do you think is going to happen?"

"I fully expect you to whip both my ass and my cock without hesitation!" I blurted out.

"Exactly. I am glad that we have an understanding. Now stand up."

I fell off her lap onto the floor and used the coffee table to get back to my feet. I was starting to feel a rush of euphoria because I thought we were done and I was going to be allowed to head home. No such luck!

"You were getting heavy on my lap, so for your last fifteen strokes, I am going to have you bend over this armchair. Now fetch your leather belt for me!" she demanded.

As I walked over to my pants, I internally berated myself for not wearing my light canvas belt. This fucking leather belt was gonna hurt!

As I returned and handed the belt to her, she told me to put both hands on the chair arm, spread my feet wide, and stick my ass straight out. I did everything she asked without hesitation. After all, wasn't that the point?

"Now," she calmly stated, "We are going to finish your punishment. I am going to go slow and emphasize every stroke. After every blow I want you to count the number of the stroke and say, 'Thank You.' And don't forget to push your bottom back out after every stroke or you will get extra strokes. Do you understand?"

"Yes, Ma'am."

"Ok, let us proceed," and with that she whistled my belt through the air like a professional Tiger Tamer, laying it across both my cheeks.

"Yeowwww," I screeched, before remembering to add, "One, Thank You."

"Two, Thank You."

"Three, thank You."

Again and again, she repeated the process and I made sure to stick my ass out so I wouldn't get extra strokes.

Again and again, I also made sure to count the stroke and thank her. It wasn't easy, but I managed to not miss a stroke.

Around number seven or eight, I noticed my cock hardening again and I had no idea why. I didn't feel like I was having fun. She evidently noticed it too because she suddenly reached around and roughly squeezed it. That only made it get harder.

"Hmmmm...I'm not sure how happy I am with that right now," pointing to my cock with the belt.

I felt sudden terror as I thought she was about to start using the belt on my cock. I'm not sure that I could take that.

"But, let's finish these strokes and then decide what to do about it," she continued, to my evident relief.

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Chapter 5

After finishing the fifteenth stroke, Victoria told me to stand before her with my hands on my head, as she rather heavily sat back down in the large armchair.

Unfortunately, my penis was still sticking straight out.

She eyeballed it and me for a few minutes before starting to speak.

"We need to get rid of that thing," pointing at my erection, "before we can finish the night."

I didn't like the sound of that.

"Have you ever tasted your cum?" she asked.

Horrified, I blurted, "NO!"

Raising an eyebrow, she said, "Why are you sounding so scared? I bet you expect all those bimbos I see coming and going from your cabin to suck and swallow your cum. Do you think you are better than them?"

Oh no, another one of those questions that I didn't dare to honestly answer.

"Of course not. I never force them to. They just do it," I stated, realizing even as I said it how pitiful it sounded.

Very unladylike, Victoria snorted.

"Your ignorance befuddles me, young man. It looks like I need to teach you another lesson."

"Fuck me" suddenly flashed through my mind.

"I think I want you to stand there before me and masturbate into your hand," she calmly said.

I was anything but calm as "Fuck me" again flashed through my mind. I suspected that I knew where this was going and the thought of it completely grossed me out.

"It's not like you have a choice," she declared, "Quit wasting my time and start jerking."

Reluctantly, I did as she asked. I tugged and pulled for several minutes, but didn't seem to be getting anywhere fast. Secretly, I was very relieved.

With a heavy sigh, she sat up and pulled her sun dress over her head, and unclasped her bra. Once that was done, she sat back in the armchair and spread her legs. I couldn't believe what I was seeing. Her very full breasts were wrinkled and sagging but damn, they were still incredibly beautiful. Oh, how I wanted to touch them. And her bush, her hairy blonde bush, looked like a magical botanical flower.

"Begin again," she directed, as she closed her eyes and began circling one of her nipples with the fingers of one hand, while she played with her clitoris with the other.

I stood there transfixed.

When I thought this night couldn't get any crazier, it had once again. What was a boy to do? I did as I was instructed and started tugging on my cock harder than ever, gazing upon that thick, mature body spread out before me in all its classical feminine glory.

It wasn't terribly long before I heaved and spurted into my hand. I awkwardly stood there, ropes of cum hanging off my fingers, scared to death of what her next instruction would be.

Sensing my stillness, she slowly opened her eyes and met my gaze.

"Lick it," she commanded.

I could hear a voice screaming in my head, "Nooooooooo," but what could I do?

In hindsight, I should have turned, grabbed my clothes, and run the fuck out of there. It's not like she could have stopped me. But you know what they say about hindsight?

At any rate, I was caught like a fly in her web.

I slowly raised my hand to my lips and with great hesitation and a little gagging, started licking and slurping the slimy mess from my hand.

Again, I am not going to lie and say that I enjoyed it. It fucking sucked. Both the smell and taste made me keep gagging but fortunately, I didn't puke. I didn't even want to consider the consequences if that happened.

Finally, I was done.

"I am proud of you," she purred, from heavy-lidded eyes, "Now that you have tasted your own cum you will be a much better and understanding lover for all your girlfriends. Don't ever ask them to do something that you aren't willing to do."

I slowly nodded.

"Get on your knees."

I sank to my knees and waited for further instructions. I was hers to command. I had broken so many of my barriers this night, I'm not sure that there wasn't anything that I would do if she commanded.

"Now that the punishment and instruction phase of this night is over, I think the 'Thank You' part of the night should start," she uttered, speaking barely above a whisper.

"Crawl to me and properly thank me with your tongue for the discipline that I have taught you this night."

Mesmerized by the giant blonde bush before me, I crawled.

When reaching her, I gently began kissing and licking along her inner thighs until I reached her hairy mound.

With as much tenderness as I could muster, I started raining soft kisses upon her glorious cunt, before switching to slow, long licks along the edges. Soon I started massaging her clit with my tongue.

I could tell that she was enjoying it as her hips slowly started to grind and she started to moan very softly. Her hands slid down and pressed my head and tongue deeper.

As I continued working her clit with my tongue, I slowly inserted two, and then three fingers into her cunt. She began to moan louder so I started to slowly pump them in and out, making wet, squishy sounds.

Slowly, I speeded up. Her moans grew louder. It was easy to see that her orgasm was building.

When it came, it came loud and hard, with her whole body violently shaking.

I held on for the ride, with her juices smeared all over my face, and continued flicking her clit with my tongue until she said, "Stop."

We both stayed where we were for about five minutes, her in the chair and me on the floor between her knees. I didn't dare move without her permission.

Finally, she pulled herself slightly up in the chair and looked down upon me. For several moments she was quiet.

"You did well, although I think you could have done better," she stated.

I immediately lost my sense of calm, thinking that she was going to beat my ass or cock some more.

"However, we will explore more of that in the future. For now, go home. I tire of you and want to go to bed."

As her words sank in, I was strangely disappointed. I slowly climbed to my feet and started gathering my scattered clothes. After putting them on, I headed for the door.

As my hand grabbed the doorknob, I heard her say, "Stop," once again.

I froze in my tracks and glanced back, with a wee bit of anticipation.

"One more thing," she commanded, "Do not shower or wash your face until we talk tomorrow afternoon. Now go!"

I exited the door and gently closed it behind me.