Punishing the Sitter


I certainly didn’t expect to see my babysitter playing with herself while watching lesbian porn on my computer when I came home early. I mean, I wasn’t upset at the sight of a nearly naked eighteen-year-old squeezing her titties and fingering her pussy as she watched a video of an older woman spanking a much younger lady but it did catch me by surprise, that’s all.

Jenny came from a conservative, church-going family. Her father was a town leader and her mother was active in the PTA. All of my friends recommended her as a babysitter and I took them at their word. This was the first time since the divorce that I let anyone besides family watch my little girl. Unfortunately, the date I was on was cut short due to a medical emergency so I had come home early.

The look on Jenny’s face was priceless. She blushed furiously, trying to cover her body with her hands, tears forming in her eyes, as she stammered apologies when I opened the door. I had to try really hard not to burst out laughing, instead putting on a stern face.

“What the hell is going on, young lady?” I asked. I had been expecting to get laid tonight and was still horny. The sight of Jenny’s body worked me up even higher.

“Please, Miss Reynolds, I’m so sorry!” Jenny said, starting to cry.

“I am so ashamed of you! I’m going to have to tell your parents about this.” I said, trying to sound stern. Jenny’s eyes got really big at that and she shook her head no, silently pleading with me. “Unless…”

“What? I’ll do anything. Please don’t tell!”

I put my purse down and walked over to the couch, sitting down. “Come here, Jenny.” I said. She walked over and stood in front of me, her hands never leaving her body. “Hands down!” I exclaimed and she complied. Jenny’s little nipples were still hard from where she’d been teasing them and her pussy was obviously slick with her juices. I had to squeeze my thighs together as a tremble went through my body. I kind of felt bad at how upset she was. At her age, I was doing the same thing. Hell, I was only about eight years older than her but, at this moment, I felt like her mother.

“Jenny, do you want me to tell your parents about this?” I asked, my tone gentle but firm. She shook her head no, her eyes downcast. “Do you agree that you were being naughty?” Jenny let out a sob as she nodded. “You know you have to be punished for your bad behavior, right?” Again, Jenny nodded. “So, what do you think I should do?” In her rush to cover up at my surprise entrance, the porn on the computer had continued playing. A very feminine squeal of pleasure emanated from the speakers.

“Um, I…I don’t know.” Jenny stammered out. “Maybe you could spank me?” She spoke the last statement barely above a whisper.

“What was that? I didn’t hear what you said, dear.” I replied, smiling to myself.

“Um, maybe you could spank me.” Jenny said again, a little louder this time.

Another shiver coursed through my body right then. I could feel myself getting moist.

“Well, I’ll tell you what. If I spank you, none of what happens here tonight will leave this house, okay?” Jenny blushed again and nodded once more. I sat there for a moment, letting the tension build as she shifted nervously from one foot to the other.

Finally, I reached out and took Jenny by the hand, pulling her across my lap. I could feel her trembling in anticipation of what was about to happen. “I’m going to spank you now, Jenny. Please tell me why.”

“Because I was looking at naughty pictures,” came her reply.


“I was touching myself.” Another squeal from the woman on the computer.

“Yes. You were supposed to be watching my little girl, not getting yourself off, right?” Jenny nodded; her head hung in shame. At that moment, I brought my hand down hard on her tight, little ass.

Jenny let out a squeak of pain and clenched her butt as a nice pink handprint appeared on her skin. I realized that I didn’t want to wake my daughter so I leaned down and picked up Jenny’s discarded panties from the floor. They were silky and lacy with a damp spot in the crotch. I brought them to my nose and inhaled deeply, enjoying the womanly scent. “Open your mouth, Jenny,” I commanded.

She complied as I wadded the panties up and shoved them in her mouth. “If your panties come out of your mouth, you’ll get another ten spankings, understand?” I informed her. She nodded and relaxed her ass cheeks. That’s when I spanked her again.

Another squeak, nicely muffled this time, filled the air as I began to spank Jenny in earnest. I established a rhythm, alternating between her right and left side. If she clenched up, I would wait until she relaxed before delivering another blow. After the twentieth smack landed, I started rubbing her beautifully reddened backside gently and I could feel the heat emanating from her skin.

It took Jenny a moment to realize her punishment was over. She had started crying about the tenth spank, around the same time her right leg had dropped off my lap, affording me a wonderful view of her pretty pussy. Glancing down, I saw the wetness had intensified. Moving my fingers down, I gently Beylikdüzü escort pried her pussy lips apart and inserted one, then another, finger into her.

Jenny’s response was purely instinctive. She began to moan into her panties as I explored her pussy in depth, moving my fingers in and out, twisting my hand, scraping her spongy inner wall with my manicured nails. In no time, I could feel Jenny’s body tremble, then tense, as she clenched down on my fingers in orgasmic bliss.

I continued fingering Jenny through her orgasm, only stopping when she slid off of my lap onto the floor where she laid there, her body twitching. I smiled down at her, then stood up. It was my turn for a little pleasure.

Undoing my skirt, I let it fall to the floor and kicked it across the room. Reaching down, I felt the crotch of my panties. Little strands of my juices clung to my fingers when I pulled them away. The urge to finish myself off was almost overwhelming but I fought it, instead yanking my panties off and tossing them over to where my skirt had landed.

Bending over, I grabbed Jenny by one of her pigtails and pulled her up. Her eyes got really big when she opened them and saw the state of my undress. I pulled her panties out of her mouth, tossing them over to where my clothes were. “Are you a good girl now, Jenny?” I asked. She nodded; her eyes red with tears. “Good. Now, I want something in return. Do you know what that is?” Again, she nodded.

I sat down on the couch and spread my legs wide. The fur covering my pussy was matted with my juices. Pulling Jenny up to a kneeling position by her hair, I directed the teen between my legs. Gripping her other pigtail, I looked her in her eyes. “Get started,” was all I said.

I pulled Jenny tightly against me and she dutifully affixed her mouth on my cunt. She was tentative at first, hesitantly exploring the folds of my pussy with her tongue. I closed my eyes and let out a contented sigh which must have emboldened her because she began to lick me in earnest right then.

I could tell that Jenny had never done this before but, to be honest, I was so worked up at that point, even her untrained tongue brought me to the brink quickly. The thought that mine was the first vagina that she’d ever tasted ran through my mind as I pulled her in tighter, grinding my pussy against her face. I could feel the stirrings of an orgasm building as her tongue brushed against my clit. Glancing down, I could see Jenny’s eyes were closed and her cute face was shiny with my juices. That’s when she wrapped her lips around my clit and flicked it with her tongue.

I held my breath, trying not to scream out, as my juices flooded the poor girl’s face. She drank deeply, trying not to drown I guess, as my grip tightened on her hair. After what seemed like a blissful eternity, I let go of Jenny’s pigtails and shoved her away from my cunt.

After I calmed down a bit, I opened my eyes and let out a little giggle. Jenny was on her knees, trying to lick her face clean of my fluids. I reached out and pulled the young woman beside me on the couch. Tilting her face up, I leaned down and kissed her deeply, our tongues wrestling. When we broke the kiss, she snuggled up next to me and rested her head on my chest.

“Are you going to be a good girl now?” I asked.

“Yes, Miss Reynolds,” Jenny replied. “I’m sorry that I was naughty.”

“Hmmmm…” I said. “I don’t know. You might need a little more correcting before I’m convinced.” Jenny let out a giggle. “Now go and bring your panties and my purse to me.” I ordered. She quickly rose up off the couch and complied. I took the offered items from her hands. “These are mine now, understand?” I asked as I held her panties up. She nodded and blushed. Then I reached into my purse and retrieved three twenty-dollar bills. “This is for tonight.”

Jenny smiled and took the money from my hand. Quickly dressing, sans panties, we shared a kiss before she left to go home. “Yep,” I thought to myself. “A lot more correcting.”

I waited a couple of weeks before calling Jenny and asking if she was available to babysit again this coming Saturday. I had to let out a little giggle at the speed in which she agreed. I knew letting the little seed of sexual pleasure that I had planted in her soul blossom for a bit would drive her crazy. Then I called my ex mother-in-law and asked if she would like some time with her granddaughter to which she readily agreed. I actually liked my ex-husband’s mother. It was just his cheating ass that I couldn’t stand.

That night, I retrieved my biggest dildo and Jenny’s panties, stripped naked, and pleasured myself to a couple of great orgasms while rubbing my clitty with the silky material. I then used the panties to clean up the juices that had leaked out of my pussy. I wanted to make sure that the fabric was basically saturated with my cum as this was going to be the only thing Jenny would be wearing.

Saturday came and I answered the door at five o’clock. My young lover was obviously anxious to get started. I was dressed conservatively, as I’d been the last time. Psychologically, I wanted to establish that I was Beylikdüzü escort the adult. Jenny didn’t disappoint either. The tight, pink tee shirt she was wearing made it obvious she wasn’t wearing a bra and the cut-offs, probably the skimpiest shorts she owned, gave me an excellent view of her toned and tanned legs.

I smiled and invited her in, shutting the door, before grabbing her and kissing her hard on the lips. Jenny returned my kiss with enthusiasm; I could feel her trembling as I grabbed her ass and squeezed. When I broke the kiss, Jenny just stood there, her eyes cast downwards, unsure of what to do. Reaching out, I lightly caressed her breast, feeling the nipple harden under my touch.

“Well, I have some bad news,” I stated, trying to sound disappointed. “It seems that my mother-in-law wanted little Kimmy for the weekend and my date cancelled so it seems that I won’t be needing your services after all.” I had to stifle a giggle at Jenny’s crestfallen expression. “Unless…” Jenny looked up at me, hope in her eyes. “Unless you would perhaps like to stay for a while. I hate that you had to drive all this way for nothing and it gets so lonely with just me and my daughter.”

“Um, sure. I understand. Thank you, Miss Reynolds for inviting me to stay.” I smiled and ordered the young woman to sit on the couch to which she complied. Heading into the kitchen, I opened up a new bottle of red and retrieved two glasses. I took the wine and glasses to the living room and sat down right next to her so that our bodies were touching. I poured Jenny a glass and she accepted the drink a little hesitantly but still took a large gulp to which she sputtered. I let out a laugh as I took a sip of my own.

We talked a bit about her school and social life. I wanted to make Jenny comfortable with me, relax her a bit. I turned my body so that my tits were pressing against her shoulder and placed my hand on her thigh, gently rubbing the soft, smooth skin. I knew that I could have her anytime I wanted but I didn’t want to rush it. We had all night and, if my plan worked out, all day tomorrow, too.

I finished my glass of wine, put down the glass and gently leaned over so that my lips were a mere inch from Jenny’s ear. “Have you been a good girl, Jenny?” I asked in a sultry whisper. She nodded, unable to speak. I moved my hand higher up her thigh, touching the bottom of her shorts. “Hmmm…I don’t believe you, little girl. Let’s see if you are telling the truth.” Moving my fingers, I went under her shorts. Just as I thought, Jenny wasn’t wearing any panties. My tongue flicked out, licking her earlobe as my fingers continued their upward move.

“A good girl would want me to stop,” I said, my fingertips grazing her pussy lips. I was a bit surprised, pleasantly so, to feel no hair on her crotch. My little Jenny must have shaved her pussy bare. “Do you want me to stop, Jenny?” I asked. She let out a little mewling moan and shook her head no.

Jenny’s body shook, threatening to spill the little bit of wine left in her glass as I removed my hand and popped open the button on her shorts. I took the glass from her hand, put it on the end table and then unzipped the fly, slowly removing them from her body. Her freshly shorn crotch came into view and I ran my hand over the smooth skin. “Good girls don’t shave their precious little pussies. Only little sluts do that, don’t they Jenny?” I asked as I dipped my finger between the cleft of her legs. She was already soaking wet.

Jenny blushed furiously and nodded; her eyes closed. Leaning down, I pressed my lips against hers, flicking my tongue out as I continued to gently run my finger up and down her juicy snatch. I pushed my tongue past her lips just as I pressed my finger into her hole. Jenny moaned into my mouth, her tongue touching mine as I began to finger-fuck her, slowly at first, then picking up the pace.

With my other hand, I pushed up Jenny’s shirt, exposing her tits. Breaking the kiss, I trailed my lips down her neck, planting little kisses as I went. I resisted the strong urge to give her a hickey, marking her as mine. I didn’t want to jeopardize what I had going and wasn’t sure that Jenny could lie convincingly enough to her parents. Reaching her right nipple, I wrapped my lips around it, gently biting down and tickling it with my tongue.

Jenny held onto my head as I teased her tit with my mouth and fucked her with my finger. Just as she was about to crest, I pulled away, removing my hand from her pussy and my mouth from her breast. She let out a whining moan, a look of consternation on her pretty face.

“Not yet, Jenny,” I whispered. “Naughty little girls like you have to earn the right.” I brought my fingers, all shiny and sticky with her fluids, to her lips. “Now, clean my fingers of all your yummy cum.” I pushed my fingers past her lips and, just as I’d commanded, Jenny sucked and licked them clean.

“Mmmmmm…very naughty, Jenny,” I said after I removed my fingers and wiped them dry on her tee shirt. “I see that you still need a bit of corrective measures. Don’t you agree?” Jenny gave me a little nod. “Now, I want you to go to the kitchen and Escort Beylikdüzü bring me back my biggest wooden spoon.” I almost orgasmed right then as her big, blue eyes widened at my command. “I am going to spank you again.”

Jenny’s eyes began to water at the thought of what was about to happen but she stood up and walked to the kitchen. I poured myself another glass of wine and took a few sips as I heard her rummaging through the drawer.

She walked back in carrying the wooden implement of her punishment and stood in front of me, her eyes downcast. I sat there, enjoying the view, drinking my wine for a minute or two, again to let the tension build.

After finishing my glass, I set it on the end table and took the wooden spoon from Jenny’s hand. It wasn’t the biggest one I owned but it was big enough so I didn’t press the issue. I grabbed her by the wrist and pulled her across my lap.

“You know why you have to be spanked, don’t you Jenny?” I asked as I ran my hand over her bottom.

“Because I’m still a naughty, little girl,” Jenny replied, her voice soft. She let out a little squeak of surprise as I spread her ass cheeks wide, enjoying the sight of her puckered anus.

“Yes. Yes, you are,” I said, tickling Jenny’s butthole with my finger. She let out a moan as I pressed my finger into her ass. “Good little girls wouldn’t get turned on by another woman fucking them in the butt. Good little girls wouldn’t shave their snatches bare. This is why I have to spank you again.”

Jenny nodded in resignation and then cried out as I quickly removed my finger and brought the wooden spoon down hard and fast on her right ass cheek. I proceeded to spank her for nineteen more strokes. By the time I was finished, Jenny’s ass was crimson and she was crying on my lap. But, at no time did she try to get up.

“Okay Jenny, I want you to go stand in the corner of the room next to the T.V. with your hands behind your head. You move from that position and I will give you another twenty spankings, understand?” Jenny nodded, rose off of my lap and did exactly as I’d commanded. I sat there for a while, enjoying another glass of wine, watching as she squirmed. I couldn’t help myself. Raising my ass off the couch, I lowered my skirt and panties and rubbed my pussy to a quick orgasm.

I rose up, removed the rest of my clothes, and, after putting away the wine and glasses, ran to the bathroom to relieve myself. Tiptoeing down the hall, I stood in the door frame, watching Jenny to see if she would touch her sore bottom but she didn’t move. Smiling, I walked to the bedroom, retrieving her old panties which I used to wipe myself dry of my cum and piss, and also grabbing a vibrator.

I tossed a couch pillow onto the floor when I entered the living room. Placing the panties and toy onto the coffee table, I walked up to Jenny, pressing my body against her back, the fur of my pussy tickling her red ass. I reached around, taking hold of her little titties, my fingers tweaking her nipples. “I am so proud of you, little girl,” I whispered into her ear. I began to rub my crotch against her ass and smiled as she ever so slightly arched her back to increase the pressure.

“Don’t move your hands,” I ordered. I moved my right hand down between Jenny’s legs and started rubbing her clit as I continued to fondle her breasts with my left hand. She was so wet and let out a gasp as I increased the friction on her clit. Again, just before she got off, I stopped.

“Okay, you can move now,” I said, stepping back. “Just don’t touch your naughty pussy.” Immediately her hands went to her ass and she turned around. Her cheeks were tear-stained and her big, blue eyes looked at me pleadingly. I knew how desperately she needed to orgasm right then. “Do you need to pee?” I asked. Jenny nodded but didn’t move. I stepped back and she scampered off.

Walking behind her, I stood in the doorway of the bathroom and watched as Jenny gingerly sat down on the toilet. Her eyes got big and she blushed all over when she realized I was standing there. I stopped her when she reached for toilet paper to wipe herself dry. “Naughty little girls like you can’t control themselves when touching their pussy,” I said, pulling her up by the arm.

I walked my little lover back to the living room, standing her in front of me as I sat back down on the couch. “You need to orgasm, don’t you Jenny?” I asked. Again, she blushed all over and nodded, unable to meet my gaze. “I want to hear you say it, honey.”

“Yes Miss Reynolds, I need to orgasm,” Jenny said, her voice low. I picked up the vibrator, turned it on low and held it out.

“Show me how you play with yourself, Jenny.” She let out a sob and took the toy from my hand. Laying down on the floor, her head on the pillow, Jenny began to rub the toy on her pussy. I sat there enjoying the show that she put on. “I bet I know what you’re thinking about,” I said as she dipped the tip into her pussy hole. “You’re thinking about the spanking you just received, aren’t you? You’re thinking about my naked body; my juicy pussy you want to taste, my tits you want to suck on.” Jenny nodded; her eyes closed. “You’re thinking that you are a naughty, little girl playing with yourself in front of another woman; a woman who just punished you, aren’t you?” Jenny nodded again; her hips raised in the air as she rubbed the vibrator up and down her slit.

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