I, Jack the Whipper

Chapter One: I Choose My Next Target

I sat on my couch watching the evening news. It was a Friday evening, and I wondered how I would spend my weekend. I realized that I wasn’t even paying attention to most of the news items being presented. But then there was a news flash, with the title “Jack the Whipper”. I sat up.

“This is just in from the police. Several women have reported that their houses were broken into at night while they were all alone. The intruder wore a mask, and no information exists about his facial features. However, he is described by the women as being a man perhaps in his early thirties. This mysterious intruder, upon entering the houses of the women, then proceeded to overpower them, tie them up, and then torture them through the night. The police have revealed that none of the women complained of sexual assault, and subsequent forensic tests have confirmed this fact. However, the women report being tied up, and then beaten with canes, and an assortment of whips, leading to this masked sadist being dubbed “Jack the Whipper”. Some of the women also reported other torture instruments that they could not recognize, but whose effect was also very intense. We now go live to Catherine Drummond, one of the women who had to face the Whipper a few days back.”

I stared glued to the television. The picture changed to that of an attractive woman, possibly in her late thirties. She looked shaken up, but there were no signs of physical injury on her body. A friend, also in her thirties, sat next to the woman with her arms around her as she spoke.

“I-I don’t know how he got in. I didn’t hear anything. I just turned around, and there he was. I was about to scream, but he jabbed me with a stick or something that gave me a big electric shock, and I probably passed out. When I woke up, I found myself naked and my hands were tied above my head to a hoop in the ceiling. Then he approached me. He had a-a whip in his hand…and…and he raised it…and…oh God!...”

The woman put her hands across her bosom and began to sob, as her friend hugged her close and motioned the cameras away. The picture returned to the news station, and the presenter continued.

“Police are currently hunting for clues or information regarding the identity and the motives of the Whipper. In the meantime, the police chief has issued a request to all women living alone to securely latch their doors and windows after evening, till the Whipper is apprehended. That’s all for now. We’ll bring you the latest information as it comes in. And now, it’s time for the weather report.”

I hit the ‘mute’ button on the remote, and sat back. I was half-amused at what I had seen and heard. Suddenly, I thought of my Aunt Rita. She lived all alone in her house. And it was a big house too. Was there something I could do? I thought for a moment. Yes. I would go and visit her, for the night, or maybe a couple of nights, until this whole Jack the Whipper business cooled down a bit. I got up to pack my bag. I put into it everything I would need for my trip, and with the bag over my shoulder, I picked up my car keys.

Aunt Rita was a single woman, her one and only marriage had ended many years ago. She was in her mid-forties, but had looked after herself very well. She had a pretty face, one that hid her age quite well. She was always very happy to see me, though I had been too busy of late to get the time to visit her. I was sure she would be delighted to see me again. And I was sure that I too would be delighted to see her again.

Chapter Two: I Come Face to Face With Aunt Rita

It was a thirty minute drive to Aunt Rita’s house. I looked at my bag sitting on the passenger’s seat of my car. I thought of all its contents and smiled. I had the entire kit with me tonight. It sure was going to be a lot of fun torturing Aunt Rita. Jack the Whipper, I thought with a chuckle, was on the move again.

I pulled up a few blocks away from her house, and looked all around me as I got out of the car. It was about 11 pm. Her neighborhood was silent, and I set off at a casual pace towards her house. I looked all around me when I reached it. All clear. I walked up to the front door. Another quick look around me, and I reached in my bag and took out the lock-picker. It didn’t take long for me to open her front door, and with another glance over my shoulder, I stepped into her house, closing the door gently behind me. I made sure that all the curtains were drawn, and then I made my way to her bedroom. When I was outside it, I pulled my mask out of my bag and donned it. It covered my face completely, except my eyes, and my lips. Masked and ready, I took the cattle-prod out of my bag, the ‘stick’ which the young woman on TV remembered so vividly. I gently pushed open Aunt Rita’s bedroom door and walked inside.

She was asleep on her bed. It was a hot summer’s night, and she lay without any covers on the bed, wearing a white nightgown. I stood near the side of her bed. I pushed the ‘charge’ button on my prod, but somehow I didn’t feel like shocking her senseless like I had done for the other women. They were a lot younger than her, and could take a lot more pain. Perhaps I should be a bit more gentle with my aunt, I thought. I touched the tip of the prod to the tip of her left nipple, and it firmed up under her nightgown at the touch. Aunt Rita moaned softly in her sleep. I drew closer to her, and in my firmest voice, whispered, “Get up!”

She was a relatively light sleeper, and she woke up hearing my voice. But I knew that she would not recognize it, because under my mask I wore a digital scrambler that made my voice sound like a distorted, menacing hiss.

Aunt Rita opened her eyes, and gasped as she saw my masked face. She tried to get up, but I pushed the tip of the prod further into her left breast, and she whimpered.

“Stay still!” I commanded. The deep hiss of my voice had its effect on her too, just like all the other women.

“Do you know who I am?” I asked.

She was gasping, and trying to swallow. I pushed the tip of the prod a bit more into her bosom. She moaned.

“Yes…yes, I know. God! You’re Jack the Whipper!”

I chuckled inside. The women would from now refer to me by this name, I thought. Jack the Whipper. Did have a ring to it!

I moved the tip of the prod over her breast, gently stroking it, and then ran it over her neck, touching it below her trembling double chin.

“Did you watch the news tonight?” I asked.

“Y-yes, I did.” She stammered.

“Then I’m sure you know what I’ll do to you if you try anything silly. Hmm?” I thrust the tip into the soft, moist skin of her double chin. She grunted.

“Yes. I know. Please, please don’t. Don’t hurt me, please.”

“On your feet!” I hissed. She obeyed without any delay. In a moment, my aunt was on her feet, standing ramrod straight as I probed her back with the tip of the prod. Her nipples were erect with excitement, and made two bumps on her white nightgown.

“Good!” I said, walking around in front of her, tracing the outlines of her nipples with my fingers, “Now go to the bathroom and wash your face. I want you looking fresh. Remember, don’t try anything funny!”

I pinched one of her nipples as I said this. She squirmed, and from the look on her face, I knew she took me seriously. I followed her into the bathroom, where she splashed water on her face. Then I guided her into her living room.

“What-what’re you going to do to me?” she asked nervously.

“Haven’t you been watching the news? What did I do to all the other women?”

She looked aghast.

“You’re going to…torture me?”

“Quite right. Now what’s your name?”, I asked, pretending I didn’t know.

“Rita.”

“Okay, Rita. Take off that nightgown.”

“No, please don’t torture me. Please.”

“I said take off your nightgown!”

“No, no please. I beg you. Don’t torture me, please…please.”

I touched my cattle-prod to the top of her left breast and pressed the button. There was a jolt of electricity, and Aunt Rita jumped at the touch.

“Aaaaahhhh!!!! That hurts!!”

“Off with your nightgown, or you’ll feel plenty more of that. And this is just the lowest setting.”

Terrified, she started to remove her nightgown, and soon let it fall to the floor. It was quite hot, and she wasn’t wearing a bra, so her full breasts bounced free. I traced their curves with the tip of the prod, and she nervously looked at my finger on the button, almost anticipating another shock to her nipples or areolas. She had lovely breasts, with dark brown nipples standing out proudly from her light brown areolas. The flesh was smooth and supple, and dotted here and there with small black moles. Her bosom heaved as she breathed rapidly, looking into my eyes with fright. I let her keep her panties on, for now, but I could make out that they were getting soaked with her juices already.

Chapter Three: Aunt Rita’s Torture Begins

“You have lovely breasts, Rita.” I said.

“Thank you, um..”

“Call me Whipper.” I said, giving her a gentle teasing kiss on the cheek to arouse her further. She breathed in deeply and closed her eyes.

“Let’s get you warmed up, Rita.” I continued. I walked over to my bag, and brought out a long piece of wood with metal studs sticking out of them. I laid this on the dining table. “Okay, come here, and place your breasts on these.”

“But-they’ll hurt…” she began to protest. I began to toy with my prod suggestively, and hesitantly, she walked over to the table. I stood behind her and helped her bend down till her nipples were just inches off the studs. They were not sharp enough to draw blood, but they were good enough to give her a good stinging sensation. I pushed her down by the neck the last few inches until I heard her gasp, and looking down saw that her nipples had settled onto the studs.

“There we go.” I said, alternately increasing and decreasing my pressure on her back, “That’ll get your tits warmed up for more in no time. Now then Rita, let’s talk. Are you scared right now that you’re going to be tortured soon?”

“Y-yes. Oohh!” she said, as the studs bit into her tender nipples.

“Are you going to call the police and tell them about me tomorrow like those other girls did?”

She remained silent and I continued.

“Well, that was very stupid of them, because I’m going to have to visit them again now, you know. To punish them more…severely.” I hissed into her ear. She shuddered.

“I-I promise I won’t tell anyone, but please have mercy on me, Whipper.”

“Oh I will. I’ll make sure you’re not hurt too bad by the torture, Rita. Come on, get up. Up against that wall.”

While she moved slowly towards the wall, I searched in my bag for a pair of handcuffs. They were specially made stick-on type handcuffs, useful when one does not know whether there are convenient places to tie one’s subjects. I clapped the cuffs over her wrists, and then stuck the handcuffs to the wall, so that her hands were in a wide V above her head. I stepped backed and observed her, and could not help smiling under my mask. Here I had my Aunt Rita, naked, perspiring, frightened, tied to the wall, her full breasts trembling, her long nipples protruding enticingly.

I reached inside my bag and took out my pliers, and held one of them in each hand as I walked towards her. She stiffened as she saw me approach, and was trying desperately to make out what their purpose was. For all the other women I had tortured, I had remained more or less silent throughout the proceedings. But for Aunt Rita, I felt that I had to be a bit more tender and understanding. I had her naked and was going to torture her through the night, but she was my Aunt after all, and I thought I should be a bit…gentler…

“Do you know what these are, Rita?”

She remained silent, and looked alternately at the pliers and my masked face.

“Well, you’ll soon find out. You see, Rita, before I begin to torture my subjects, I try to find out what their tolerance limit to pain is. And these pliers here,” I snapped the jaws a few times, and she whimpered, “These pliers, they help me gain that understanding.”

I touched the jaws to her breasts and traced circles around her nipples. She stiffened and began to sob softly.

“You do realize what I’m going to do now, Rita, don’t you? I want to hear you say it.”

“Yes….you’re going to…you’re going to squeeze my nipples with those things to see how much pain I can bear…”

“Very good. Here are the rules. You have to take the pain all the way to the point where you simply can’t bear it any more. You’re not allowed to scream before that. If you do, well…it won’t be nice. And remember, don’t think you can scream before it really really hurts, because I can tell simply by looking into a woman’s face whether she’s faking pain. Take my word for that, okay Rita?”

I slid her nipples in between the jaws and pressed them slightly. She breathed in sharply and closed her eyes.

“You feel that, Rita?”

“Yes.”

“Does it hurt?”

“A bit.”

I tightened my hold. She gasped, and tried to hold back a scream.

“Does that hurt more?”

“Yes, it does!”

I squeezed even harder. She threw her head back against the wall, and bit her lip to stifle the scream that welled up within her. Her breathing was short and rapid. She was sweating profusely.

“Does it hurt even more now?”

“Oh…Ouch!!...Yes!! It hurts a lot.”

“But I feel you can take more. Let’s see now…”

I squeezed the handles some more, and pulled the pliers upwards slightly. She instinctively stood up on her toes, trying to ease the tug on her nipples as much as she could. Her face was contorted with pain, and she fought desperately to prevent herself from screaming.

“How does that feel?”

“God…Oh!!!...Oh God!!!....Hurts!!!...Please…no more…!!” she pleaded between gasps.

“You’re not at your limit yet, Rita. I can tell”

I increased the pressure one last time. I now had a firm grip on the pliers handles, and the jaws at the other end had by now flattened her nipples with their bite. Aunt Rita let out a long gasp, threw her head from side to side, fought violently against my grip on her nipples, and finally, unable to control herself, let out the scream that had been trying to escape from her for a long time.

“AaaaaaahhhhhhHH!!!!! OoooooohhhhhhH!!!!!!” she screamed as I held the pressure and twisted her nipples with the pliers.  I looked at her facial expression, and realized that there was no chance she was faking the pain. This was my Aunt Rita’s tolerance limit, and I was impressed by how well she had held out this far. I released my grip on her tits, and as the blood rushed back into her tortured buds, she sobbed and let out a long-drawn wail.

“Good girl!” I said, rolling her throbbing nipples between my fingers.

“Mmmph!!! Mmphh!!!” she yelped, as my massage drew out the last bits of pain from her already sore nipples.

“You were very strong there, Rita. Now let’s start with the real torture.”

I reached into my bag and brought out a whip. It was made of leather, with a thin strap about two feet long. It was designed to deliver sharp, stinging blows without lacerating the skin. I had used it to great effect on the other women, and Catherine, the woman they showed on television, actually had an orgasm after a prolonged whipping session.

“Surely you know what this is, Rita?”

“A whip. You’re going to whip me while I’m naked?”

“Well, it’s a waste whipping someone who’s clothed, right Rita?” I said, and took pleasure from her whimper.

I uncoiled the strap and drew closer to her, the whip dangling from my hands.

“So, Rita. Have you ever seen torture scenes in movies where women get whipped?”

She remained silent, and I prodded her stomach with the handle of the whip. She shifted uncomfortably.

“Yes...I can’t remember the names of the movies though…”

“Okay, what happened in them?”

“I remember one where Antonella Lualdi got whipped by another woman. There was another where Brigitte Bardot got whipped after a card game. I also remember another one movie set in Arabia where a woman gets tied to a post and whipped.”

“Good. Now in these scenes, on what part of their bodies were the women whipped?”

“On their backs.”

“Interesting. Why not on their breasts?”

She was about to say something, and then she realized what I was getting at. Her face immediately showed the anticipation of the pain that she would have.

“Please, Whipper. Don’t whip my breasts. I won’t be able to take it.”

“You’ll have to Rita. Stand straight please.”

With a whimper, Aunt Rita obeyed. I brushed the whip against her nipples until they were almost shooting out of their goosebumped areolas. Then I stepped back to take up position. She stiffened and closed her eyes. I raised my hand and swung the whip.

Crack!!!

The lash caught Aunt Rita at the junction between the underside of her breasts and her torso, a particularly painful first stroke. She jumped at the stroke, and the sting shot through her bouncing breasts. She clenched her teeth, and threw her head back in pain.

“Aaaaahhhhhhhh!!!! God!!!!”

“Count the strokes, Rita!”

“One! Oh God! No!”

Crack!!!

The second stroke slashed across the top of her breasts, across her chest, about six inches above her nipples, kissing the underside of her arms as it went. She yelped as the pain shot all over her feminine body.

“Oooooooohhhhhh!!!!! Two!”

“Good girl! Keep counting!”

Crack!!! Diagonally across her left breast, kissing the nipple.

“AaaaiiiiiihhhhhhH!!! Three! Oh God!!!”

Crack!!! A similar backhanded stroke across her right breast.

“Eeeeeeeehhhhhh!!! Four! Mercy!!!”

Crack!!! A rising stroke lashing the undersides of her breasts.

“Oooowwwwww!!!! Five! No, stop! Please!”

“I’ll tell you what, let’s play a game. You have to call out which part of your breasts you want me to hit. If I hit it, we continue with the whipping. If I miss, no more whipping. Go on!”

She remained silent. I raised the whip above my head.

“It’s the only chance you have, Rita. Better be smart and take it.”

She remained silent some more, and then said softly,

“Left nipple.”

“Okay, will do. Let’s see now…”

I extended my left hand forward, holding the handle of the whip, while with my right hand, I pulled the tip backwards, much like a bow. I lined up the lash with her left nipple, and released my right hand from the tip. The whip surged forward with a hiss.

Crack!!! The strap dug squarely into Aunt Rita’s tender left nipple, which tucked into her breast momentarily, before popping out, reddened and as erect as ever. Ripples spread across her breast, and her initial gasp now gave way to a more expressive holler.

“Aaaaaaghhhhhh!!!! OooohhhhhH!!!!!! Six!! Oh, God!”

“Sorry, Rita. I win, you lose. Stand up straight! Good! Let’s see if I can hit you other nipple now.”

Crack!!! The whip bit into its target, as Aunt Rita screamed helplessly once more.

“Aaa-aaa-aaaaahhh!!!! Seven! No more!!!”

“Now, how else can I test my aim? Ah! You’ve got some lovely beauty spots on your breasts, don’t you? Great! How about…” I looked over her bosom, “How about I try for that nice mole just above your right areola?”

She looked down to see what I was aiming for, and then closed her eyes once more.

Crack!!! The whip dug into her right breast. I moved forward and cupped the tortured mound in my hand. I tapped the mole, and traced out the red streak that the whip had caused over it. She moaned and sobbed softly. I looked up at her.

“Aren’t you forgetting something, Rita?”

“Eight!” she blurted out.

“Good girl!”

I then proceeded to target each of the moles that dotted her breast, and each time the whip found its mark with my practiced accuracy. Satisfied that I had not missed a single spot, I then settled into a nice forehand-backhand rhythm, lashing her breasts from both sides, while her painful screams and helpless counting continued.

Crack!!!

“AAAAHHH!!! Fifty!!”

I stopped. Fifty strokes already! How time flies when you’re watching a pretty woman’s breasts bouncing wildly from strokes of the whip. Aunt Rita’s breasts were now a uniform hue of reddishness, and bathed with sweat, as she moaned and sobbed.

“Okay, Rita. That’s enough whipping for now.”

“Thank you, Whipper. Thank you!” The relief was evident in her tone. I went up to her and undid her restraints, and she collapsed into my waiting grasp. Had she been anyone else, I would have left her cuffed to the wall for a couple of minutes and then started out on the next torture. But this was my own Aunt, and I had to be more…delicate.

She moaned as her lashed breasts pressed against my body, and I took her nipples between my fingers once again.

“Ouch!! Ouch!! Please don’t. They’re very sore!”

I leaned into her and kissed Aunt Rita on the lips. She was taken my surprise, and did nothing until I squeezed harder on her nipples, and she realized she was expected to kiss back. She returned a nervous peck on the cheek, and as her nipples suffered another agonizing tweak, relented and kissed me back on the lips.

“Good girl! You know, that’s just one of several whips I’ve brought along.”

She looked at me with terrified eyes. I laughed at her discomfort.

“Don’t worry, Rita. I won’t give you two whippings one after another. The night is still young, there’s plenty of time left.” I poked her nipples with my thumbs, eliciting another yelp of pain.

I was thoroughly enjoying this. I had my sexy middle-aged aunt in my power. I had set her breasts and nipples on fire already, and was running through my mind the list of tortures that I would put her through in the next couple of hours.