Punishing the Sitter

Just as she was about to orgasm, I got off the couch and knelt down, pressing my cunt right on her mouth. Jenny's tongue snaked out and she collected the juices that had leaked out of me. Just then, she screamed into my pussy as she came, her whole body trembling. I leaned down, moving her hand out of the way and began to feast on her sopping wet pussy.

Damn, Jenny was delicious! I ran my tongue up and down her lips, exploring every fold of her little puss. Sucking her engorged clitty into my mouth, I whipped my tongue back and forth while gently biting down. I could hear a muffled squeal from her as her muscles tightened again, another orgasm coursing through her.

It was too much for me and my thighs tightened around her head like a vice. Jenny was trapped there, trying her best not to drown as I flooded her face with my orgasmic fluids. I collapsed, spent, and rolled off of her.

We both laid there for a while, collecting our breaths. I pulled myself up onto the couch, grabbed Jenny's dirty panties and wiped myself clean. I smiled as I looked at her. Jenny had the most serene expression on her face.

"Okay Jenny, kneel in front of me." She rolled over onto her stomach and pushed herself to a kneeling position. I used my foot to spread her legs apart. "This is how you kneel; hands on your thighs, legs spread wide. Understand?" Jenny nodded and assumed the correct position. "Good girl," I said, smiling. "Now, please pick up the vibrator, turn it off and lick it clean of all your naughty cum." She quickly complied, practically deep-throating the plastic toy.

When she finished, I tossed the panties down at her knees and took the toy from her hand. "Put them on. While you are here, these are the only things that you will wear." Jenny rose up and donned the panties, still damp from my juices. "Now, I want you to spend the night here. Do you want that, too?" She nodded, a little smile on her pretty face.

"Okay, then call your mother and let her know that you are going to be spending the night." I was curious to hear what lie she was going to tell her mom.

It was fun. It was fun to see Jenny back down on her knees in front of me as she took a deep breath and called her mother. It was fun listening to her stammer out a lie that I was going to be out late tonight and had asked if little Jenny could just spend the night. It was fun to hear Jenny tell her mother that she knew it meant that she was going to miss church the next day. And it was really fun to see her try to have her conversation the whole time I was rubbing her dirty cunny with my big toe. As soon as she hung up, my phone rang.

I let it go to voice mail, knowing it was Denise, Jenny's mom. Instead, I reached out and grabbed my little toy by one of her pony tails, scooched down on the couch, and pulled her tight against my pussy. Jenny closed her eyes, moaning in pain and arousal, as I began to grind my cunt hard against her face. After enjoying Jenny's tongue for a minute or two, I called her mother back. "Hey Denise, what's up?" I said, pretending I was a little tipsy.

"Hey Rachel, sorry to bother you but did you ask Jenny if she could spend the night babysitting?" Denise asked. "Because she does have church tomorrow."

"Yeah, I did. Sorry 'bout that," I replied, almost laughing out loud. "This date is going very well, if you know what I mean."

"Oh...um, of course." I swear I could hear Denise blushing over the phone. "Well, I suppose it will be okay if it's just for this weekend."

"Of course. Your daughter is a perfectly fine young woman, Denise." Jenny licked and sucked on my clit, causing my breath to catch. "You've obviously done a fine job raising her. I can only hope to do as good a job with Kim."

"Why thank you, Rachel," Denise replied, obviously happy with my compliment. "I hope you have fun tonight."

I scrunched my eyes shut as a little tremor coursed through my pussy. "Oh, I'm sure I will," I said as my hips bucked. "Talk to you later." I almost threw my phone across the room as an orgasm coursed through me right then, coating Jenny's face with my fluids.

I let go of Jenny's hair, gazing at her though half-lidded eyes as I did my best to catch my breath. My juices glistened in the dying sunlight as she knelt in front of me, smiling. "Pretty good job. You're going to get a lot of practice pleasing me," I said as I trailed my toe across her breasts. "Do you have a dildo at home, Jenny?"

Jenny was shocked at my question and stammered out a no. "Really?" I said in mock surprise. "I thought a naughty, little girl like you would have a whole drawer full of fake dicks to play with." She blushed furiously at my comment, looking down at the floor. "Well, we'll have to remedy that. But first, we need a shower."

I rose up off the couch and commanded Jenny to follow me, which she did, walking behind me like an obedient puppy. I started the shower, adjusting the water to my liking, and stepped in, motioning her to come in also. "I want you to wash me, Jenny. If you do a good job, I might wash you too."

Jenny knelt in front of me and after getting her hands nice and soapy, took my leg in her hand, gently washing my foot and caressing my calf and thigh. When she finished the right leg, she sensuously cleaned the left before moving to the cleft between my legs. I almost orgasmed again as Jenny thoroughly soaped my cunt, making sure I was nice and clean. Instead, I turned around so she could soap my backside, including my asshole.

I stood there, enjoying the hot water cascading down my body as my little toy cleaned my body. After she massaged my tits with her soapy hands and washed each arm, I let the water flow over my body, rinsing the soap off before turning off the water and stepping out. "I don't think you've earned the right to clean your naughty cunny yet," I said as Jenny looked at me with a puzzled look. I knew that my dried juices hadn't washed off her face yet.

"Now, get out and dry yourself off. Don't wash your face or I'll spank your ass with my hairbrush," I said after drying my body and handing her the used towel. Picking up the dirty panties she'd been wearing, I watched her quickly rub herself dry, only stopping her as she reached between her legs.

"Hurry up and dress yourself. We're going to out." Taking the panties with me, I went to my room to dress as Jenny scampered to the living room where her clothes were. After donning a nice summer dress, I walked to the living room to find Jenny kneeling at the foot of the couch with her clothes on. Smiling at the sight, I ordered her to stand and tuck her shirt in, then snapped my fingers and exited the house, not even bothering to turn around to see if she was behind me.

We drove to the nearest McDonalds. I had the air conditioning on full blast and by the time I pulled into the parking lot, Jenny's nipples were poking out nice and firm. Instead of going through the drive through, I handed her a twenty and told her my order, making her go in and purchase the items. While she was inside ordering the food, a half-full bottle of water I had in the car gave me a wicked idea.

Jenny practically ran to the car, carrying our food, her braless tits bouncing nicely under her shirt. I took the food and drinks from her, putting them in the backseat, then ordered Jenny to sit on her hands after she buckled herself in.

She did as I ordered, looked at me quizzically as I took a sip of water as I started the car. Then her eyes got big and a shocked look came over her face when I quickly poured the remaining water right onto her chest. "Your hands better not move or I'll pull the car over and spank you right here," I said as she started moving her arms. "Understand?" Jenny nodded, tears in her eyes, as I pulled out of the parking lot and drove to our next destination.

The trip only took about ten minutes and I almost wrecked a couple of times glancing at Jenny's soaked shirt and rock-hard nipples. Pulling into the parking lot, I was pleased to see it was empty except for the employee's car. The store itself was non-descript; yellow, stucco walls, no windows and only one door. We exited the car and I opened the door for Jenny, motioning her inside.

Marge was working tonight and we nodded greetings at each other and Jenny and I approached the counter. "Hey Rach. Whassup?" Marge said in her deep, sexy voice. Even though she was in her forties, Marge was still a very desirable lady with huge breasts barely concealed under her flannel shirt.

"Hey Marge, it's a special night," I said, smiling and winking at her conspiratorially. I'd told Marge about Jenny a week ago and it was she who suggested bringing the teen to her store.

"Oh, in that case, let me lock up really quick," Marge said as she walked to the front door, locked it and flipped the open sign to closed. "Now, what's so special?"

"Well, we're here to buy Jenny her first dildo and I think she needs your expertise in selecting it." Jenny was mortified, her face beet red and looking ashamed at the floor.

"Now that is special," Marge said, a predator's smile on her face. "There's something about your first real toy. Let me see..." Marge's voice trailed off as she studied Jenny's body. "She's pretty small so nothing too big," Marge said, her hand stroking her chin. "You ever been fucked before, girl?" Jenny shook her head no, still blushing. "Speak up. Can't hear you." Marge demanded, her voice getting louder.

"No," Jenny mumbled. I swatted her on her ass, causing her to let out a squeak.

"Be respectful, Jenny, and answer Marge so she can hear you, okay?" I said, gently but firmly. "Or do I need to pull your shorts down right here and discipline you? I'm sure Marge will let me borrow a paddle."

Jenny looked like she was about to burst from shame but she answered Marge's question in a clear voice. "No, ma'am. I've never been...fucked before."

"Okay, so we don't want this monster," Marge said as she walked over to the wall of dildoes and selected a twelve incher. Its girth was about a big as Jenny's wrist. I laughed out loud at the look on Jenny's face when she saw the prick Marge was holding.

"Well, let me look around this wonderful store while you let Marge help you," I said, pushing Jenny towards the older woman. I walked around, picking up items that I was going to use on my toy; an anal plug with a jeweled heart, adjustable nipple clamps, a leather collar, and a nice leather paddle along with a bottle of strawberry lube. By the time I returned to the two, Jenny was holding a dildo in each hand, trying to decide.

"Good choice," Marge said as Jenny handed her back the one she didn't want. "I have that exact one at home."

"Well, that's wonderful," I said, smiling. "See, that wasn't so hard, was it?" Jenny let out a sheepish smile and shook her head no. "So, Marge, what's the damage?"

"Well, you owe me one-forty for the shit you want, but I'll tell ya what. Since this is Jenny's first toy, I'll let her have it for free." Jenny's eyes lit up at that. "On one condition." Marge added as I handed her my credit card. I grabbed the bag of goodies and followed Marge to the back room, Jenny between us, still carrying her dildo.

"The only way you walk out of this store with that toy for free is if it's shoved up your snatch," Marge said, her arms folded across her ample chest. Jenny's eyes got big again and she looked like a captured fawn as she stood there, dumbfounded.

"That seems fair," I said. "I mean, it's the least you could do for Marge giving you such a nice gift, right?" I placed my hands gently on Jenny's shoulders, then moved my arms slowly down her body until I reached the front of her shorts. She was trembling as I undid the button and unzipped the fly, letting them fall down her legs and pool at her feet. Then, grasping the bottom of Jenny's shirt, I pulled it up off of her and threw it aside.

Marge let out a whistle of appreciation at the sight of Jenny's naked body. "Damn Rachel," she said as she licked her lips. "This little cunt is fucking amazing. She any good at eating pussy?"

"Well, she's okay for a beginner but she could definitely use practice," I replied.

"Heh," Marge said, smiling. "Practice does make perfect." She pulled her shirt out and unbuttoned it, her wonderful tits coming into view. Marge's bra surprised me. It was a dark, satiny red and when she kicked off her shoes and undid her pants, the panties matched. Unclipping the bra, Marge let her mouth-watering tits swing free. Her nipples were nice and thick.

Jenny stood there, mesmerized, watching this complete stranger disrobe. Marge's bush was matted with her juices when she took off her panties and sat down on her desk chair, spreading her legs wide.

I led Jenny over to where Marge was sitting and gently guided her onto her knees, then pushed her head forward right into Marge's splayed pussy.

Marge put her hand on the back of Jenny's head and held her in place as I reached out, tweaking the older woman's nipples and fondling her pendulous breasts. Marge and I kissed, our tongues wrestling and swapping spit before I broke the kiss, opened the bag with my purchases, pulled out the lube and took Jenny's dildo from her.

After thoroughly coating the dildo, I pried open Jenny's pussy, positioned the tip right against her hole and began to work the toy in. Leaning close to Jenny's ear, I whispered loud enough for Marge to hear "You said you were a good girl, Jenny. Do good girls eat stranger's pussies while getting fucked by a dildo, Jenny?" She whimpered in reply as her mouth was full with Marge's cunt. I moved the dildo in and out faster, with each pass pushing it in a little more. "I think I should paddle your ass right now. I brought one just for that you know." Again, Jenny let out a whining whimper. Marge was starting to breath heavy and I knew she wouldn't last much longer.

Finally, I reached Jenny's hymen. Waiting for the right moment, I slowly withdrew the cream covered toy. Right when Marge let out a scream of release and clenched down, I shoved the dildo hard into Jenny's cunny, popping her cherry as her face was covered in cum.

Jenny let out a muffled scream as her hymen was ripped open, causing Marge to clench down again. I shoved the dick quickly in and out with full strokes while I diddled Jenny's clit. Marge never let go of Jenny's head as I fucked the young woman into orgasmic pleasure, her fluids reddish with the blood from her cunt.

Finally, it was over. Marge let go of Jenny and the poor girl collapsed on the floor, her ass in the air and her head on the hard-concrete floor. She was gasping for air but I wasn't quite finished. Leaving the toy buried deep inside her, I reached in the bag, pulled out the jeweled butt plug, greased it up good with lube and some of Jenny's blood and pussy juices and slowly pushed the plug into her ass.

Jenny let out a moan of pain as it finally popped in, her anus closing around the intrusion. Reaching down, I pulled Jenny up to a kneeling position, her hands automatically resting on her thighs. "I think you should say thank you to Marge for such a wonderful gift, Jenny," I said as I tweaked her nipples.

"Thank you, Marge for the gift," Jenny said in a soft tone. Marge smiled and nodded. We shared a kiss as Jenny put her shirt and shorts back on and then Marge kissed Jenny hard on the mouth before we left, letting the older woman bask in post-orgasmic bliss.

Jenny and I left the store and got into my car. Again, I made her sit on her hands. "Hmmmm...you did very well, Jenny." She couldn't help it; a little smile appeared on her face. "But you know you were naughty. I think another spanking with our new paddle is in store when we get home." Jenny nodded, the smile disappearing. She sat in dread at the thought of the pain to come as my house drew nearer and nearer.

By the time we arrived at my house, Jenny was almost in tears. I ordered her to grab the food as I took ahold of the bag of toys and walked inside, enjoying the view of my little pet walking gingerly with a dildo shoved up her snatch and a plug in her ass.

After reheating the food in the microwave, Jenny and I sat down at the table and enjoyed our meal. I felt a little bad for her as I saw the look on her face. To say Jenny looked apprehensive about her forthcoming paddling would be an understatement so I decided to treat her a little for being a good girl and following my instructions. I figured that rewarding good behavior was just as important as punishing her for being naughty.

When we finished the meal, I directed Jenny to go to the bathroom and take her clothes off, then wait for me in the proper position. I took my time cleaning up dinner and taking the bag of toys to my bedroom, carefully laying out the collar, nipple clamps, paddle and bottle of lube on the bed. Walking into the bathroom, I saw that Jenny had followed my instructions to a tee, kneeling on the floor, unclothed, her legs spread wide and her hands on her thighs, the dildo still protruding from her dirty cunt.

I ordered Jenny to stand up and lean over with her hands on the side of the tub. After taking some pictures of the dildo and jeweled plug still inside her, I carefully removed both of them, then handed them to her, instructing her to clean them off and put them on my bed. As she did as I had ordered, I ran the bathtub water.

The look on Jenny's face was priceless when she returned. Obviously, the implements on my bed had caused her discomfort. She probably thought that I really wasn't going to paddle her or at least tried to put it out of her mind. I helped her into the tub and began to gently run a washcloth over her body, concentrating on her sore pussy and ass. Jenny relaxed, closing her eyes and smiling at my ministrations.

"You did wonderful today, baby," I said as I ran my hands over her body. "They say there is a special bond that is created between a woman and the one who took her virginity. Do you agree?"

"Yes, Miss Reynolds, I agree," Jenny said as she smiled beatifically at me, her eyes still closed.

"That's wonderful, Jenny," I replied, rubbing her clitty with increased pressure. She began to moan, biting her lower lip as I teased her. "I feel it, too. No matter what happens with the rest of your life, I will always be your first lover."

I continued to rub her, running the terry-cloth wash rag up and down her slit. Jenny raised her hips, trying to increase the pressure but I didn't grant her the release she craved. Instead, after another minute, I removed my hand and ordered her out of the tub. Jenny complied, standing still as I patted her dry, then took her by the hand to my bedroom.

I sat down on the bed and had Jenny kneel on the floor in front of me. Picking up the collar, I held it in my hand, enjoying the smooth feeling of the leather for a moment before I spoke. "Okay baby, this is where you make a very important decision. I want you to really think about what I am about to offer," I said, looking her straight in the eyes. "This collar represents your obedience to me. If you accept it, this and your panties will be all that you wear when you come over here, understand?" Jenny swallowed hard and nodded. "This means that you will be my toy, my pet while you are here. I promise that I will not permanently harm you or make you harm yourself." Again, Jenny nodded. "But, if you accept this, you will follow my orders. Anytime I think you are being naughty; I will punish you. This also means that if I call you or text you with instructions, you will follow them."

Jenny's eyes widened when I said that. The realization that I would send her commands to follow when she wasn't over here obviously scared her. "So, as I said, think about this very carefully," I reiterated, fondling the collar in my hand. Jenny closed her eyes, in deep thought. Then, after a minute, she bowed her head in submission.