Punishing the Sitter

I smiled, reached out and buckled the leather collar around her neck, making sure it was snug but not too tight. Jenny shuddered as the symbol of her submission was secured. "Alright," I said when I finished. "I now control you. Do you agree?" Jenny nodded, her eyes moistening with tears. "No baby girl, I want to hear you say it."

"Yes Miss Reynolds, you control me," Jenny said, her voice soft but with resolve.

I smiled at her reply, my hand caressing her cheek. "Okay, so I expect a few things. First, you will keep your naughty cunny bare for me and also clean. So too with your ass. I expect both of them cleaned regularly inside and out. Understand?" Jenny nodded. "Secondly, you will tell the truth, no matter what I ask. If I find out you have lied to me, your punishment will be most severe." Again, Jenny nodded. "Good, now stand and bend over at the waist, facing away from me. Use your hands to spread your ass cheeks as wide as you can."

Jenny complied, her little rosebud coming into view. I could see the moistness of her pussy. It was obvious that this was exciting her. Picking up the anal plug, I coated it with lube. "This doesn't leave your ass unless it's to clean yourself out or use the bathroom," I said as I inserted it. "This even means when you are at your home, at school, sitting in the pew at church, it doesn't matter."

I directed Jenny to kneel as I picked up the paddle. "I will be adding more rules later on but there is one rule left for now," I said, looking down at her. I wanted to make sure that Jenny's grades didn't suffer so I came up with a simple solution. "You will bring me a copy of your report card and progress report as long as you're in school. Any grade below a B will earn you five spankings with the paddle. So, if you have two Ds, that is twenty spankings, is that clear?" Jenny nodded one last time.

"Good," I said as I played with the paddle. "Now, I am going to show you how the paddle feels. You did a wonderful job with Marge but you told me you were a good girl when you arrived today. This is obviously a lie because good girls don't lick stranger's pussies. Good girls don't get fucked in the back room of a porno shops."

Jenny looked down at the floor as I said this, ashamed. Commanding her to stand, I rose off the bed and maneuvered her down so that her tits were flat on the blanket, her arms were outstretched wide. "Now Jenny, you aren't to move until I say so." Not even waiting for a reply, I brought the paddle down across her ass.

Jenny gasped and almost reflexively moved her hands but caught herself in the nick of time. Again, I spanked her with the paddle, enjoying the sight of the bright red mark it left on her fair skin. I didn't want to hurt her too much so I didn't use my full strength. Eight strokes later and Jenny was sobbing. I knelt behind her and began to run my tongue up and down her slit. It was dripping with her juices and I licked her clean, then inserted two of my fingers deep inside her, fucking her until she orgasms. I wanted to condition my little pet to associate pain with pleasure.

After she came, I ran to the bathroom, retrieved a bottle of cream and gently applied it to her bruised backside. Jenny alternated between moans of pleasure and sobs of pain and after I was finished, I undressed and climbed onto bed, pulling the girl next to me.

I held Jenny's trembling body close until she finally calmed down and snuggled closer. "I know that was hard, Jenny," I whispered as I stroked her hair. "But you know that you deserved it for being so naughty." Jenny nodded, her hand resting on my tit. "Do you still agree to be my little pet?" I asked. Jenny paused for a second, then nodded again.

"Yes, Miss Reynolds," Jenny softly said. "I am still yours."

"Good girl." It had been a long day and I knew Jenny was exhausted but I was so worked up and hadn't orgasmed in several hours. "Now, get between my legs and show me that you're still my pet."

Jenny moved her body gingerly down and knelt between my legs, her sore ass sticking up in the air. Jenny may have just started pleasing women with her tongue but she definitely was a quick learner. In no time, I coated her pretty face with my fluids as I ground my pussy against her mouth. Then, Jenny surprised me as she inserted her two fingers into my cunt and fucked me to another orgasm.

I was seeing stars as I laid there. It took all my willpower to reach down and grasp Jenny by one of her pony tails, pulling her next to me. Holding her tightly against me, we both drifted off to sleep.

When I awoke in the morning, Jenny's arm was draped over my stomach and our legs were entwined. It felt really good to be waking up to another in my bed. I didn't realize how much I missed the feeling. It was made even better that the person I was waking up with was soft and feminine, with delicate curves and a delicious pussy.

I decided to let my little pet sleep in so I gently disentangled myself from Jenny's body and walked quickly to the bathroom to relieve myself. After I finished, I enjoyed a nice breakfast and sipped a couple of cups of coffee as I thought about what I would do to Jenny before sending her home to her nice, conservative family. I laughed to myself at the thought of Denise finding out that I'd wrecked her baby girl; corrupting her and turning her into a lesbian love slave.

I could hear Jenny stirring from the bedroom so I walked in and just stood at the doorway, watching her stretch sensuously. Her hand went to her ass and rubbed the bruises, then her eyes got big when she saw me. Immediately, Jenny rolled out of bed and knelt down in the submissive position. I was impressed but didn't say anything.

Instead, I walked over, patted Jenny on the head and commanded her to rise. Reaching out, I placed my hand on the back of her head and kissed her hard, shoving my tongue into her mouth. Breaking the kiss, I looked into her eyes as I unbuckled the collar and removed the plug from her ass. "You have ten minutes to use the bathroom, shower and make yourself presentable for me. Every minute over ten earns you five spankings on your already sore ass, understand?"

Jenny's nodded and she scampered off to the bathroom as I started the stopwatch app on my phone. I headed back to the living room, carrying Jenny's collar and plug, sat down and enjoyed the rest of my coffee.

It was nine and a half minutes later when Jenny ran out of the bathroom and knelt in front of me, panting. I could have lied and gave her a nice early morning spanking but decided against it. If this was going to work, I had to play by the rules that I'd set as well. Instead, I told her how proud I was that she made it in time. Her smile at my compliment was truly pussy melting. She looked at me with adoration in her eyes as I grabbed the collar and buckled it around her neck.

After instructing her to stand, I inspected Jenny closely, making sure that she had in fact cleaned herself. Well, to be fair, it was mainly an excuse to rub my hands all over her body. The added touch of humiliation of my "inspection" was a bonus. I made sure to insert little compliments and critiques along the way. Then, as she was facing away from me, I had Jenny bend over, grabbing her ankles. Her puckered anus came into view and I gently inserted the anal plug as I had forgotten to bring the lube. It took some pushing but, soon, it popped in. Jenny gasp at the intrusion but didn't move.

With the symbols of her submissiveness firmly in place, I let her go to the kitchen to get some breakfast. While she was sitting at the dining room table eating, I went back to the bedroom to retrieve the dildo, lube and nipple clamps, then poured myself one more cup of coffee and waited for Jenny to finish.

Upon completing her meal, Jenny was back in front of me, kneeling on the floor. Now, it was time to introduce some more pain. I reached out and began fondling Jenny's breasts. Her tits were well-formed and decent sized; her nipples nice and thick. She began to moan as they hardened under my ministrations, arching her back as I gently pinched and rolled them between my fingers.

When I felt that they were hard enough, I grabbed the clamps sitting next to me. They were adjustable; the more I tightened the screw, the more pressure applied. Running the connecting chain through the ring on her collar, I applied the first clamp to Jenny's right nipple, tightening the screw until a look of pain crossed her face. I had to pull the chain so that I could capture the left nipple between the jaws of the clamp. When I was finished, both of her nipples were turning a nice shade of red and her tits were pulled up. Running my index fingers along the tips of her nipples caused Jenny to moan loudly.

I sat back, just enjoying the look of pain on my little pet's face as I sipped my coffee for a few minutes. After finishing my coffee, I picked up the lube and dildo, liberally coating the plastic prick with the strawberry scented cream. At my command, Jenny stood up, her legs spread wide and her fingers locked behind her head, which had the effect of pulling her breasts up even more. Even well lubed, it took some work pushing the full eight inches inside her virgin-tight pussy.

"Okay Jenny, we are going to play a little game this morning," I said as I wiped my hands clean on her stomach. "I want you to do ten deep-knee bends. Keep your legs spread wide and your hands behind your head." Another look of pain crossed her face as her nipples began to throb. "Now, if you can make it to ten without the dildo falling out, I will remove it and those nipple clamps. However," I added as she started to bend her knees. "every time it falls out, you will receive five hand spankings and have to start over, understand?" Jenny nodded, the expression on her face a combination of pain and determination. "Okay, start."

The first attempt, Jenny made it to five before the dildo fell out of her pussy with a loud thunk onto the floor. I had to keep reminding her to keep her head up the whole time as she kept trying to scrunch her arms and shoulders forward to relieve the pressure on her tits. I shook my head in disappointment, reached out and pulled Jenny across my lap, delivering five quick, hard slaps on her ass. Then, after retrieving the dildo from the floor, Jenny was instructed to lick it clean of her juices, the lube and dirt from the floor.

When I was satisfied of the job Jenny did cleaning the dildo, I reapplied the lube, had her stand the proper way with her legs spread and shoved it none to gently back into her cunt. This time, she made it to eight. She started to cry a little as the dildo slipped from her pussy as she was rising back up. I sighed in mock exasperation and again reached out, pulling her across my knees. After another five spankings, to which she really started crying, I again made Jenny clean the dildo with her mouth, shoving it between her lips and fucking her face with it. She gagged a few times as I pushed it down her throat but soon, it was clean again.

Once more, I coated the plastic toy with lube and inserted it deep inside Jenny's pussy. I was proud of her as she finally did the ten knee-bends, taking them slowly, gripping the dildo tightly with her cunt muscles.

On completion of the tenth one, I smiled and reached out, slowly withdrawing the prick from her juicy snatch. It was coated with a mixture of lube and cunt cream and I couldn't help myself as I inserted and withdrew it a few more times. Jenny gasped, her hips reflexively starting to buck as I slowly fucked her. But finally, I withdrew it, placed it on the end table and undid the clamps.

Jenny stifled a moan as blood rushed back into her abused nipples. "Okay Jenny," I said as I reclined back onto the sofa. "You can move your arms again." Immediately, one hand went to her nipples and the other went to her backside as she tried to massage the pain out of both areas. She started whimpering as her hand movements turned her on even more.

I gave her a minute or two, then I tossed a pillow onto the floor. "Jenny, for doing the ten knee-bends, I will allow you to orgasm." Picking up the dildo by the base, I handed it to her. She grasped it by the shaft, coating her fingers with the cream and her cum still coating the toy.

Laying down, Jenny started rubbing the tip of the dildo up and down her slit a few times before gingerly pushing it into her hole. She started fucking herself with short strokes, increasing the pace and depth each time she pulled it out.

After getting it about half way in, Jenny started rubbing her clitty. Her hips bucked immediately at the added stimulation and her mouth was formed into an "O", her eyes screwed shut in concentration.

I watched Jenny please herself for a few minutes before I couldn't take it any longer. I started rubbing my pussy with one hand while fondling my breast with the other. The sound of Jenny's panting moans, then whimpering cry as she finally orgasmed pushed me over the edge. I sprayed my hand with my cum as Jenny coated the toy buried deep inside her with her own juices.

We laid there, each coming down from our orgasm. After a few moments, I could speak again and told Jenny to clean the dildo off with her mouth, which she did with much relish. I could tell that she was really starting to enjoy the taste of womanly juices. Smiling at the show she put on, I ordered her to stand and hand the toy to me. Then I told her to get my purse.

"Okay Jenny, it's almost eleven," I said as I took my purse from her hand. "Church should just be getting out by the time you get home." Standing up, I removed her collar. "This stays here. But remember what I said about the plug up your naughty ass. That remains in unless...what?"

"It remains in unless I am going to the bathroom or cleaning myself out," Jenny replied. She smiled as I handed her a hundred-dollar bill. I also handed her the dildo.

"You have my permission to fuck yourself with this as much as you want. In fact, I expect you to," I said as her eyes opened wide and a huge smile appeared on her face. "Because, the next time you come over, I expect you will be able to do ten knee-bends without it dropping once, understand?" Jenny nodded, still smiling.

We kissed passionately, then Jenny got dressed and ran to her car, carrying the dildo in her hand. I watched her drive away, wishing she could stay but I knew that she would be back soon. Sighing, I put away the toys and took a nice, relaxing bubble bath, enjoying the silence. After soaking, I got dressed. I missed Kimmy very much and couldn't wait to see my daughter again.