Katherine Ch. 18

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Sandy agrees to be punished for past misdeeds
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Part 19 of the 19 part series

Updated 10/31/2022
Created 09/29/2003
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quimmaster
quimmaster
1,611 Followers

This is one of a series. I suggest you read them in order.

CHAPTER 18 Sandy asks to be punished

On our way back from dropping Katherine at the airport Sandy and I talked in the car. She asked me if I planned to punish her for her misdeeds in are earlier relationship. I told her I had a few things in mind. She seemed excited.

"Like what?" she asked as she slid her hand down between my thighs as we drove. Her talented fingers felt wonderful as she stroked my cock.

"Well, that may depend on what you think you can take," I said as I put my arm around her shoulder and let my hand slide down into her open top and caress her magnificent breast.

"I hope that I don't get Katherine in trouble but you know she's told me everything about what you've done together." She confided.

"Anything in particular catch your interest?" I asked. I felt her nipple harden under my palm as I caressed her firm breast. There was a long silence.

"Actually, what Katherine told me about S and how you punished her breasts sounded very...exciting." Sandy confessed.

"Would you like to have your breasts punished?" I asked as I pinched her taut nipple and she gasped.

"Well, you know that I like things rough..." she confessed.

"Have you ever had your breasts punished?" I asked as I continued to pinch and pull on her very aroused nipple.

"Actually, I've had my breasts pinched and bitten pretty hard and to be honest, it really turned me on," Sandy confided.

"Mmm," I moaned thoughtfully as I moved my hand to her other breast and began to pinch her other nipple. Sandy's stroking of my cock became more animated. I remained quiet for awhile as I pinched and pulled on her taut nipples and she stroked my cock as we drove.

"You realize that if I punish you, I will be the one to decide what I will do to your body and for how long." I said. "You will have no say in the matter."

"Yes," she said softly.

"You would agree to having your breasts punished?" I asked. Sandy nodded. "That would mean bound and beaten." I continued.

"Yes," she said softly as she squeezed my cock in her hand.

How about if I want to punish you ass and your pussy?" I suggested as I continued to toy with her magnificent breasts.

"Yes," she said softly, her voice choking a bit as she tried to utter the word.

I kissed her on the forehead as I eased my grip on her taut nipple.

"May I make a request?" she whispered softly.

"What?" I asked.

"Can I request that whatever you do to me that it leave no permanent marks?" she asked.

"Agreed," I said as I pinched her nipple gently.

"Agreed," she said as she slid away from me on the seat and then turning her body she opened my zipper and leaning over, sucked my cock into her warm and talented mouth.

That was earlier. Now it was time to put my plan into play.

While she was in the showers, I checked to see that the party was over and that most of the guests had left the building. Sandy returned from the locker room wearing a towel around her luscious body.

"Come stand over here," I instructed as the almost naked beauty came to stand where I indicated. "You asked me earlier today about punishment. It is now time," I said. I watched as she paled. "Put your hands behind your head," I instructed and Sandy raised her arms and placed them behind her head. As she did so, the towel pulled higher on her body and now it barely covered her naked pussy. I walked up to her and kissed the top of her magnificent breast. I felt her body shudder.

"Do you know what 'blue balls' are?" I asked as I lifted my face from her deep cleavage.

"I've heard of them, but don't really know what they are," she confessed.

"Then let me tell you. When a man gets sexually excited by a woman, especially when touching her body and anticipating having sex with her, his penis becomes erect and his balls begin to amass semen and the pressure in his balls becomes very powerful. When he ejaculates the pressure is relieved and the pleasure is exquisite. But if, for some reason, he is not able to climax then the pressure remains and the experience is exceedingly painful," I explained. "Guys usually call the condition 'blue balls'."

Sandy quickly realized just what I was talking about. She knew that this described her entire relationship with me. She would get me excited and then rub her pussy against my sheathed cock until she climaxed and then back off, leaving me with a severe case of 'blue balls' each time.

I started to walk around the trembling beauty as she stood before me. Her head turned to follow me as I surveyed her magnificent body. She was tall, with an inspiring figure. Her breasts were a bit large for her body, her waist slender, her hips flared nicely and her legs were long and shapely. She had shoulder length, dark hair that now was a wiry blonde and a truly beautiful face. She watched me closely, hoping for some clue as to what awaited her.

"Keep your eyes forward," I snapped and she quickly turned her head back to face the office. I continued to circle her trembling body and then reached up and ripped the towel from around her body. Sandy gasped as she stood naked before me.

I want you to understand what is going to happen now," I began. "I am going to punish you, physically, emotionally and sexually." Sandy paled. "I am going to take my pleasure in your beautiful body and I am going to try and make it as non-pleasurable as possible for you; in fact, as painful as possible." Sandy swallowed hard. “You can still back out if you like,” I said softly.

“No,” she said softly, the words choking in her throat. Perhaps it was a combination of the pain she craved and the guilt of so many nights of pain that she’d caused me with ‘blue balls’.

“You’re sure?” I asked. Sandy nodded.

"Getting back to 'blue balls', you should know that the pain remains for hours after the experience. So now, I am going to try to make this experience not only a painful one and a humiliating one, but also one where the pain and discomfort will linger for hours if not days. I remember my promise not to leave any permanent marks on your body.

"Do you agree to the punishment I have in mind?" I asked. Sandy swallowed hard and then nodded.

"I want to hear your answer," I said.

"Yes," she whispered, barely able to get the word out.

"Now you will follow my instructions explicitly and without hesitation because if you don't, I will only add to your punishment in some very exotic ways." I explained.

"Do you work out?" I asked.

"Sometimes," she responded, her voice betraying her fear.

"Good, then let's start with some nice stretches. I want your beautiful body limber and flexible,” I suggested. I sat down and watched as the naked beauty put herself through a series of stretches that accentuated the fullness of her amazing body. I felt my cock begin to stir as I watched her move. I was going to enjoy every moment of this and Sandy was, hopefully going to enjoy at least part of it.

“Do you feel loose?” I asked as I watched her move into a wide split on the gym mat.

“Yes,” she answered.

“Good, how about some jumping jacks," I said. Sandy paled slightly as she realized what she would look like as she did the jumping jacks naked. "Well?" I said and the naked beauty began to perform the exercise.

As her body began to move, her huge breasts began to bounce wildly on her chest. She now realized the importance of an exercise bra as never before. I pulled up a stool and sat down a few feet in front of her bouncing body.

"Keep going," I encouraged her as her massive breasts continued to bounce wildly and began to hurt. She tried to reach down to protect her huge breasts but I just glared at her and she went back to the exercise. I could see the pain in her face as she bounced before me and her breasts moved wildly on her chest.

"How does it feel?" I asked as the naked beauty continued to exercise before me.

"It hurts," she gasped between bounces.

"Good, it will probably hurt for hours," I said with a smile as I walked around her body as she continued to do the painful exercises.

"Can I stop, please?" she begged as I came around in front of her once again.

"Not just yet," I said softly and she continued to grimace in pain as her huge breasts bounced wildly every time her feet touched the floor. Tears were forming in her eyes as she continued to do her exercise for my pleasure. I waited a bit longer until the tears began to run down over her smooth cheek and then I said, "OK, enough for now."

Sandy sighed with relief as she stopped and reached up to her pain-wracked breasts. As she caressed them, she thought about what I'd just said. The 'for now' part of the statement worried her.

"Do they hurt?" I asked as she cradled her breasts.

"Yes," she replied, her voice showing her pain.

"Good, I hope that they will hurt for a few hours at least," I said as I reached up and pulled her hands from her tortured breasts. Pressing her hands behind her back, her shoulders were drawn back and her huge, panting breasts were thrust forward. I pulled her body close to mine and she stepped between my legs as I leaned against the stool.

“Had enough?” I asked. Sandy shook her head. “Are you sure?” I asked.

“Yes,” she whispered.

“Hands behind your head,” I ordered and the naked beauty lifted her arms and interlocked her fingers behind her head. Her magnificent breasts were raised up as she stood before me. Bending my head forward, I bit her erect nipple and sucked it into my mouth. Sandy gasped as she felt my mouth tease her aching breast. She wanted to break away from me but knew that doing so would only lead her to more and more painful punishments. Holding her body close to mine, I sucked her taut nipple into my mouth and began to bite and tease her tender nubbin. I could feel her body shudder as I teased her nipple. I then released it and went after her other nipple. Moving back and forth, I bit and sucked her tender nubbins and felt her body quiver in my arms.

Sandy couldn't believe the pain in her chest as my teeth bit into her tender flesh. She’d forgotten what it felt like to have someone really chew on her nipples. She liked the pain but it was greater than she remembered from her previous encounters with nipple chewers. The outer pain on her skin and the inner pain from the jumping jacks combined to make her feel very aroused while in a lot of pain.

Suddenly, I slid my mouth over her hard nubbin and sucking it gently into my mouth, licked the top with my tongue and then kissed her nipple. A deep shudder ran through her naked body. I released my grip on her wrists and then kissed her other nipple.

"Turn around," I instructed and Sandy turned her body away from me. My hands came up to her arms and then slid to her wrists, gently pulling her arms behind her. I picked up a set of handcuffs and closed them snugly around her slender wrists. Now she was really terrified. She knew that now she was really helpless as she stood naked before me.

"Kneel," I said and the naked beauty bent her knee and tried to kneel without falling over. I watched as her beautiful body descended before me. Leaning forward on the stool, I slid my fingers under her thick, blonde hair and pulled her hair back off of her shoulders. Then separating it into three strands, I began to braid her hair. Sandy knelt nervously as I played with her hair. I then reached over and picked up a thick rubber band and closed it around the end of her braid. Then taking a long leather strand, I slid the end through the weave of her braid. Sandy was trying to figure out just what I was doing.

Placing my hands on her soft shoulders, I could feel her body trembling. My hands slid down over the tops of her breasts and then I pinched her taut nipples between my fingers. I gently squeezed and twisted her hard nubbins as her body squirmed before me. Her nipples were unbelievably hard as I teased them.

"Time to punish you," I said as I released her nipples and stood up. Sandy knelt nervously as I walked around her kneeling body. I picked up a leather lash with several wide leather strips and shook it out. "This is going to hurt but it won't leave any permanent marks," I said as I raised the whip and brought it down across her protruding breasts. Sandy screamed as much in surprise as pain as the leather strips landed on her naked breasts. Her body bucked as angry red stripes cut across the creamy whiteness of her magnificent breasts.

"Sit back up," I barked as Sandy tried to straighten her body with her hands bound behind her. I waited as she struggled to control her movements and once again knelt before me. Raising the lash once again, I brought it down across the tops of her naked tits. Again she screamed as the lash cut across her tender flesh.

Walking around her kneeling body, I swung the whip in a wide arc and brought it down across the fronts of her huge tits and her aching nipples. Sandy screamed as she felt the leather cut into her tortured flesh. Her body buckled at the waist as her ass lowered onto her ankles and she bent her body forward.

"Sit up," I barked and the naked beauty slowly returned to the position I wanted her in. I looked down at her body as her huge tits were a deep shade of pink and rose quickly with each deep breath.

"Only a few more for now," I said softly as I brought the whip back across her naked breasts once again. Sandy clenched all of her muscles in an effort to not collapse as the leather once again cut into her naked breasts. Moving in front of her, I swung the lash backhanded and again hit her hard across her breasts. Before she could recuperate from the last hit, I swung the lash once more and hit her right across her nipples. Sandy screamed as her body buckled once again.

I walked to the side of her body and grabbing hold of her braid, pulled her body up straight once again. I looked down at her creamy white breasts and the angry, red marks that covered them. I pulled her braid back until her head lay across the seat of the stool. Her beaten breasts were thrust forward as her back arched gracefully. I leaned over her and with the lash wrapped around my wrist and dangling over her body, I leaned forward sucked her beaten nipple into my mouth. As I sucked on her aching nipple, I could feel her body shaking as the ends of the lash dangled down the front of her body and tickled the soft fur that adorned her drenched pussy.

Stepping to the side of her bound body, my hands came down and one arm slid under her back and lifted her body up onto the stool. Her head dropped back as her beaten tits rode on top of her chest. Her ass hung free in the air as her long legs splayed out before me. Her bound arms lowered slightly on either side of the stool, holding her body in place. Her pendulous breasts were drawn in the direction of her face as her head hung back, revealing the soft undersides of her massive tits. Raising the lash again, I brought it down across her stretched abdomen. Sandy screamed as her head thrust upward. I hit her across her tits once again, hitting hard against the tender flesh of her lower breasts and then systematically went to work on her bound body.

Sandy felt the lash move across her body as it ran from her beaten breasts down to the tops of her open thighs. She was terrified that I would begin to beat her pussy but I purposely only hit her across her hips for the moment.

Laying the lash across her body, I let the ends dangle down between her barely open thighs. I stepped up to her body and rubbed the front of my pants across her soft, tear-stained cheeks. She could feel the hardness of my cock as my hands came down to her beaten breasts.

"Time for a little pleasure," I teased as I let go of her breast and opened the front of my pants. I pulled my ramrod out and rubbed the tip across her soft cheek. Sandy had never consented to suck on my cock back during the time we dated. The precum that oozed from the tip smeared across the softness of her skin. Sandy's eyes were riveted to the tip of my cock as the tip slid softly across the fullness of her soft lips. Sandy eagerly opened her mouth and I slid the tip of my cock into her warm, wet mouth. As Sandy felt my hands on her beaten tits, she sucked my cock into her mouth. Straddling her head, I began to slide my cock deep into her throat as my hands squeezed and twisted her beaten titflesh. The last thing Sandy wanted to do was disappoint me. She sucked me deep into her talented mouth as her tongue pleasured my cock. She was an amazing cocksucker.

Holding her beaten tits firmly in my hands, I pulled on them as I thrust my ramrod deep into her mouth. I could feel the head move past her tonsils and actually see her throat expand as my cock moved into her throat. The bound beauty sucked hard as I skull-fucked her bound body. Her breasts ached as my hands squeezed her beaten flesh and pulled on her pained titflesh. It didn't take long for me to feel my load begin to boil as I thrust deep into her throat. Sandy could feel my body tense as she prepared to swallow what she anticipated would be a gigantic load of sperm. She wouldn't be disappointed.

My grip on her beaten titflesh tightened as I thrust deep into her mouth and with a loud grunt, my cock exploded in her talented mouth. Sandy could feel the power of my load as what felt like gallons of cum filled her mouth. She gulped and swallowed as she tried to swallow all of my cum. I watched as her huge tits rose and fell and her throat muscles contracted as she tried to keep from drowning in cum. What a sight.

When my cock finished unloading in her mouth, I leaned forward, forcing the full length of my cock into her throat. I reached down to her panting titflesh and pinching her beaten nipples, I pulled up on them, stretching her aching tits to the limit. Moving my hands in wide circles, I stretched her tits and shook them violently, banging them together as the bound woman whimpered in pain. Then suddenly, I dropped her tits and slid my cock out of her mouth and tucked it back into my pants. Sandy lay silently across the stool as she tried to recuperate from my punishment of her body.

I picked up the whip and walked around her body. I traced my fingers across the tautness of her abdomen and then let my fingers slide down through the soft curls of her pubic thatch. Sandy's thighs opened slightly as I teased her dripping pussy. I could see her erect clitoris standing up between her engorged pussy lips and teased around it with my fingers. Her body shuddered as I teased her. Bending over her body, I sucked her beaten nipple into my mouth as she gasped. Sucking hard on her nipple, I let my hand wander down across her taut abdomen and slide down between her open thighs. Sandy spread her legs wider apart as my fingers slid between her drenched labia and probed deep into her gushing pussy. I could not believe how wet she was, her juices oozing out of her drenched pussy and dripping down her thigh. Biting down on her tortured nipple, I sucked hard as my fingers began to explore the wetness of her pussy. I could feel her body squirm under me as my mouth tortured her beaten nipple and my hand began to abuse her oozing quim.

Switching to her other nipple, I continued to abuse her magnificent chest. I moved my mouth back and forth between her beaten nipples as I sucked and chewed on her aching nubbins. As her body squirmed beneath me, my fingers thrust in and out of her dripping pussy. I could hear her squealing in pain as I abused her beautiful, bound body.

Biting her nipple one last time, I released her breast and stood up over the tortured beauty. Stepping in front of her body, I reached down to her massive tits and wrapping my fingers around them, I pulled her body forward until she screamed and the stool tipped forward. Her body slid back down onto her knees and I pulled on her titflesh until her body was erect once again.

quimmaster
quimmaster
1,611 Followers
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