I stepped up to the nice-looking car parked in the same spot as last week. The car door opened for me, and I sat inside. I saw Hilda looking nervous in an oversized brown trench coat that covered her body. The window between the back and the front was strongly tinted in our favor, and I raised an eyebrow without saying anything.
I closed the door, and I turned to her, "I am out of condoms," I told her, "We will go to a sex shop and pick some things up," I continued, "I think it is time to get some toys that I will use on your moving forward." I looked at her up and down, seeing the blush on her face and a little nod. "What do you say when Mistress gives an order?" I asked her with a disapproving expression.
"Yes, Mistress," Hilda said and opened the window to the driver. "To an adult toy store. Make it a good one, and do not disturb us until we are there and you will only knock and wait." Hilda said, and I heard a male voice acknowledge before Hilda closed the window and turned to me. "I missed you, Mistress," Hilda said, softening her expression. "It took an entire morning for me to walk after last week," Hilda said, her face dark red blush on her face. "I was looking forward to this all last week, and I also found my work went way better. I found myself thinking about you a lot this week, too, Mistress,"
"Well, If you missed me so much, why don't you show me tonight properly now and when we get back to your place." I told her, "For now, show me what is under that jacket that has you worked up, Little Star."
Hilda blushed hard and nodded, and I saw her strip the jacket. My eyebrows rose as I watched the jacket drop, just as the car started to move. I looked her up and down, seeing Hilda wearing a black bra with little white stars dotted around the breasts. Her panties were matching with a little bright star just above a small patch of blonde pubic hair that was clean. I could see her doubling down on the small nickname I gave her, which was cute. I smiled and quickly pulled her over to me, finding she wasn't wearing a seat belt.
We now sat side by side, and my hands slipped up her thigh towards her pussy. "You going to be a good little slut for Mistress tonight?" I asked her.
Hilda nodded enthusiastically, and I smiled. "I want to be such a good slut for Mistress tonight," Hilda replied after a moment, and I grinned.
I lifted my skirt and pushed aside my panties, "You have till we get to the store to get me off and swallow every drop. Otherwise, I will punish you a little tonight before we have more fun." I told her, grabbed her by the hair, and pulled her face down to my lap forcefully. "Get sucking slut."
I felt her face against my flaccid cock, but her lips pressed against the base of my cock. Hilda didn't complain and began to lick as I slowly leaned back and stroked her hair as she got to work. It didn't take long for her to get me, at least at half-mast. "God, Mistress, your cock is so big," Hilda moaned a little, "I can't believe I can even get it in my mouth," She stated before opening up those wonderful cougar lips and drooling a little on my head before taking my entire head in her mouth.
I moaned as she began to lick around the head of my cock, and I reached down to her exposed panties. My fingers found her little asshole, and I felt her lips tighten and her teeth lightly brushed against my cock as I touched her asshole.
I stopped all movement and said very slowly, "Did I feel teeth just now?" I asked her as Hilda began to speed up and strengthen the suction on my cock while moving her head.
My question was left ignored, and I asked, my voice much more threatening than before, as I pressed my finger against her ass. "I asked a question Slut," I said, making my voice sterner with every word. "I believe I felt teeth, SLUT," I let the statement hand, "Did you let your teeth touch my cock without permission?" I asked her, knowing the answer.
Hilda paused and looked up at me with those beautiful eyes. "No?" She said, unsure of herself.
"So I didn't feel hard teeth against my sensitive cock?" I asked.
I could see Hilda start to question herself, and she nodded, "Sorry, Mistress, I may have by accident," She said, her voice apologetic, and I sneered at her.
"So first you didn't, and now you may have by accident," I said while sneering at her, and I grabbed her by the hair, "You are lucky, your beautiful, Slut. Get back to work," I said, shoving her mouth towards my cock again roughly, "Punishment tonight. I will make sure this time it will be more than just a morning that you cannot walk." I finished.
"Yes, Mistress," Little Star replied, and I wondered if she knew that she would be punished no matter what tonight. I would have found something at some point and used it against her. I bit back a moan and continued to tease her asshole again. I twirled my finger around her sphincter, making her moan as she continued to pleasure me.
Hilda was a good cocksucker and enthusiastic as she continued to do her best. Her tongue swirled around my cock while she tried to suck the semen out of me. I could hear the suction and her lips smack against my cock. I barely bit back a moan as she hit that spot on the head of my cock as she tried to take me deep. I let myself relax as Hilda did her best to please me. My hand came down on her ass hard, making her jump, but I felt no teeth this time as she had learned her lesson earlier. My finger went back and pushed aside the little black and white started panties, and I found her asshole and let a finger slip into it.
Hilda jumped a little again as she felt my finger push into her, but I only probed the sphincter. This made her moan even more, and she moaned after taking a breath of air. Her tongue reached out and began to lick up the length of my cock, nearly making me moan again. A great blow job, and I couldn't help but relax as Hilda did her best to please me. In return, my finger slipped deeper into her ass, making her tighten up, and I used my other hand to push her head down on my cock. Hilda and I trusted up and down her throat.
"Better, Little Star. Maybe you are worthy of my attention tonight," I stated and moaned. The car suddenly stopped, and I heard a couple of taps on the window. I looked down, "Looks like you didn't make me cum quickly enough, Little Star. It seems I have two punishments to give you tonight."
My statement made her start to fuck her throat even harder with my cock, and I moaned, and I no longer held back. I let my eyes roll back a little, and as my Little Star did her best, I released a rope of semen directly down while digging a single finger deeper into her ass. Little Star moaned and took my cock a little deeper, letting my eyes roll a little in pleasure.
A couple of moments rolled by, and I felt her swallow as I released a little more semen into her mouth. I pulled her head back but kept my cock in her mouth, letting her suck out the remaining semen. "Leave whatever semen is left in your mouth, Little Star. You will keep it in your mouth while we are shopping. Put on your jacket now, and we can go in."
Little Star slowly pulled her hair up, and I smoothed it back down, although it was still a little tousled. I didn't care and used a single finger to make her open her mouth. Inside I could see the white semen mixed with saliva bubbling a little as she took a breath. "Good, Now get dressed," I told her and watched her put on the jacket. With a little finesse, she finally covered herself back up, and we got out of the car together after I stuffed my cock back into my panties. It wasn't comfortable, but I was starting to get used to it lately.
I stepped out of the car, and Hilda got out a moment later with her mouth firmly shut. Looking toward the store, I smiled as we were at a boutique with blacked-out windows, and I began to walk toward it with Hilda in tow. We walked into the store, and it was nice. There was clothing meant to be worn during sex and toys on the walls. It looked classy, and there were curtains along the roof.
I walked in with Hilda and waited to wrap an arm around her as we came in. A woman was at the counter right next to the door, and I could tell the reason was that they needed to ID. I wasn't about to care about that, though, and walked in with my arm wrapped around my Little Star, looking around.
We walked in deeper, and I looked around with Hilda, and I found a lot of dildos quickly. I thought about it and quickly decided against them. I didn't want to double penetrate her or anything, and my cock was large enough. No need to go overboard.
I quickly found the condoms and picked up a twelve-pack of thin-ribbed condoms that I had never tried before. It was a quick pick-up, and I walked to the clothing immediately. Hilda didn't say anything, and I looked her up and down. "Go find a toy that you want, Little Star. It must deal with pain but may also make you feel pleasure. It will be used in one of your punishments. I will make double one of your other punishments if you don't. Now go," I ordered, and Little Star nodded.
I watched her go with a slight blush on her face and turned to the clothing. All of them were lingerie, but nothing spoke out to me. I wished there was a little more selection, but this place wasn't for that. It was a high-end toy shop, and I looked around some more until I found something I liked. I picked one out and frowned when I realized the bust size would be too small. I put it back and continued looking until I found something slutty that I wouldn't mind wearing. It wouldn't hide a single thing, and it was mostly straps. The best part was that I wouldn't have to care about the bust size since there was nothing covering the breasts to be seen.
I grabbed it and held onto it, walking over to the toy section. I didn't want to be here a long time and would rather be out as quickly as possible. I felt like I should have gone to my girlfriend's store, but I also didn't know if I should do that either, as I believed her store was on the wrong side of town from Hilda's place.
I started to smile as I looked through what the store must have called the pain aisle. Little Star looked troubled but did not open her mouth as she held the nipple torturers. Those were fantastic ideas, and I smiled as she put them back with a red face. It was amazing how good it felt making an older woman blush like a little freshmen schoolgirl having talked about sex for the first time. I wanted to make her blush all the time, and I moved around. I quickly found a leather paddle, one side fluffy while the other was studded.
I looked down at it and thought that I would much rather have a custom paddle made by someone who knew what they were doing than mass-produced stuff, but I picked it up. I felt like I needed a cart, so I picked up some treated rope. I hoped it was already treated as I didn't have time to burn the extra threads off. I continued to pick things up and smiled as I got a little pile in my arms as picked up toys and vibrators. Soon Little Star came up to me, and I grinned as she showed me the nipple torturers.
"Good job, Little Star," I told her, "I am sure that you will be enjoying them tonight," I told her and brought my face close to her ear and whispered, "In fact, I believe that you will be enjoying them all night long because of how naughty you have been Little Star," I told her my words a guarantee and I took everything to the counter.
I set them down, and the woman smiled as she began slowly ringing them. I watched as the bill went up a lot quicker than I was expecting, but Little Star pulled out her card and had it ready for when the woman was finished. Soon we were leaving with no other events from the toy store and had five bags of goodies from the place in solid black bags to hide the contents.
We walked up to the car, and Hilda opened the door, and I got in and moved over into the center. Hilda came in beside me, and I looked at her, "Open your mouth," I ordered, and Hilda opened her mouth. The smell of semen left her mouth, and I saw the semen mixed in still with the saliva, "How did it taste, Little Star? Did you enjoy Mistress's cum?"
"Yes, Mistress, I loved it," Little Star admitted, "Only you can make me feel like this," She told me, and I smirked.
"Good," I replied and pointed to the window. "Tell the driver to take us back to your place. Then we shall get you ready for tonight. I am sure that I will enjoy it immensely."
Hilda swallowed, and I turned to her, "Did I tell you to swallow the cum?" I asked as she was about to reach for the window opener. "Such a naughty girl," I said, shaking my head, "Go ahead and tell him. Punishment will be tonight."
Hilda looked at me, and I could see the anticipation of a slut in her eyes as she pressed the button, and the window to the driver opened. "Home," Little Star said, her voice stern, before closing the window again.
As soon as it finished closing, I turned my head to her and grinned, "Lose the jacket again," I told her and grabbed a bag looking into it. I opened it up, and a pack of batteries and some vibrators came out. I ripped open that hard plastic wrap with little trouble, as it was meant to be opened easily. Soon I was placing batteries in some wired vibrating eggs that I loved. I grabbed somebody tape and had it ready as I pulled out the nipple torturers.
I turned to look at Little Star, who was showing herself to me in only her underwear. I grinned, reached out, and pulled down her bra, showing me her little nipples. I grinned as I took out two clamps with little spikes on them that were dulled but still would send pain to her nipples every moment she moved with them on. On the clamps was a regulator that I could twist to close the clamps onto her sensitive nipples slowly, and I couldn't help the large grin on my face as I brought them to her now hard nipples.
"MMM," Hilda groaned in pain as I pressed the nipple torturers to her nipple. Then I slowly twist and close the nipple torturers to her nipples. Hilda bit her lip as I slowly finished pressing the dull spikes to her hard nipples.
I stroked her cheek, and I looked into her eyes, "Such a naughty Little Star," I said, "I wish you didn't have to make me do this," I said to her, and I smiled, "That was one, and we are not done with you, Be good."
"Yes, Mistress," Little Star replied, and I began to attach the next one to her other nipple. "MMMM!" She moaned with the pain hitting her other nipple as I tightened it, sending shivers of pain through her breasts. "It hurts, Mistress," Little Star complained.
"Almost done," I told her reassuringly and finished with a final twist, letting the clamp fall with her breast jiggling as the metal clamp handle fell against her white skin. She bit her lip again, holding back a cry of pain. "Good Girl," I told her with a smile as I leaned back and grabbed the body tape. "Now, Some pleasure to go along with that pain Little Star."
I grabbed the vibrators that I had just finished putting in new batteries for, and I placed the controller for the vibrators against her thigh. I smiled as Little Star looked down, unsure of what I was doing, as I wrapped the controllers against her skin. The body tape wrapped around her thigh, leaving only the dial for the intensity of the vibrators in reach. I put all four controllers on her thighs and taped them in place. The wires were now in my lap, and I grinned at her.
"I am really hungry now," I told her and watched her reaction as I asked, "So I wonder what is for dinner when we get to your place?"
Little Star shivered, and I leaned forward and kissed her lips as my hand brought those vibrators toward her and pushed aside her panties. I kissed her deeply, invading her mouth with my tongue as my fingers pushed a vibrator into her dripping-wet pussy. I loved how turned on she was, and my one hand reached down to the clams on her nipples. I pulled them lightly, and her tongue paused, and she groaned as the pain in her nipples assaulted her. My other hand slipped a second vibrator into her pussy, and she moaned this time as the object invaded her pussy.
I pressed my body against her more as I grabbed another vibrator from my lap and went lower this time. It was difficult, and so I pushed her back now, my breasts pressed against the nipple clamps making her groan in pain as I pressed a vibrator against the sphincter of her asshole. I felt her asshole tense, and I waited it out, kissing her more and teasing her with her tongue till she relaxed, pressed my advantage, and invaded her asshole. She groaned and moaned as I did so as I pushed a little on her naked, clamped breasts sending shivers of pain through her.
I loved doing this teasing, and I pressed deeper as I grabbed the last vibrator that I put batteries in for and brought it against her ass again. I continued to tease her tongue with my own and lightly nibbled on her lips, making Little Star moan as I pressed the second vibrator into her. This time I didn't need to wait as long as she relaxed quicker, allowing me to push it into her without problems.
Kissing her a little longer before I finally broke the kiss, I sat back, no longer teasing her nipples. "These will be your dinner guests, Little Star, while we eat." I told her, "Then we can have some more fun and finish your punishment."
"Mistress," She said and looked down just as my fingers reached the first remote.
"Care to guess which vibrator this one turns on, Little Star?" I asked.
Little Star opened her mouth and closed it, and I smirked, "My pussy?" She replied unsurely. I looked at the wire leading to her ass and turned it to the max. Little Star's eyes widened, and I watched her shiver as the pleasure sent chills through her body.
"Miss the next one; the rest will be on max, little Star. Get it right, and you will get half-strength on the rest. Fun game, isn't it, Little Star?" I asked
My hand found the next remote leading to her ass, and I smiled, looking at her, "Which one do you think this leads to, Little Star?" I asked again, and Little Star trembled as she looked at me. I could see her start to look down, and I reached out with my other hand to stop her. "No cheating, Little Star, Guess," I told her and saw her cute pout.
"My Pussy?" Little Star guessed, and I smirked.
I turned it to the max, and you could hear the two hitting each other inside of her. "Wrong, Little Star. I wonder how many times you will cum by the time we finish dinner?" I couldn't help but ask and reached the next remote, and I heard her moan loudly as I cranked it to the max.
"Mistress!" Little Star cried out, and I didn't stop with just one as I reached out and turned the last vibrator to the max, and all four were rumbling inside of her lower body. I grinned wickedly and her body shivered as I reached out this time to her nipples and pulled on the clamps. "AH!" She screamed as I introduced pain to the mix as her pussy rumbled.
I couldn't help but get hard as I looked at her, melting in pleasure with a little drool on her lips. I pulled away, and I pulled her by the legs, and Little Star fell back as the car continued to move under us. I leaned forward, and I situated myself along the seat. "You look delicious, Little Star," I said and pressed my cock against her leg. "I can't help but be hard thinking about dinner," I told her, leaned down, and kissed her.
The car continued to reach the outskirts of town, and I teased her nipples with my hands on the clamps while I heard the vibrators rumbling inside of her. I began to kiss her and tease her making her a moaning mess as I pinned her to the seat. My cock was hard and throbbing, but I suppressed the desire to take her in the car.
Little Star moaned and cried as I sent a constant shiver of pleasure and pain till I watched her squirt all over the back seat of her car. At this moment, the car tilted, and the driver tapped on the window. "I'm surprised, Little Star," I told her, "I only made you cum once before we got here. Now get ready," I told her, reaching down and grabbing her trench coat and tossing it on her. "Put it back on."
I got off her, and Little Star slowly put on the jacket. I could see her blushing face, and she opened the window once she was done. Once the window was open, Hilda spoke, "Done for the night. Go home, and you saw nothing tonight. See you tomorrow." We opened the doors, grabbed the black bags of stuff we purchased along with my backpack, and got out, leaving the car, which began to drive off out of the garage a moment later once we reached the elevator.
Hilda opened pressed the button to open the elevator, and we both got in together. Up until this moment, she looked completely normal from the outside. Nothing told me that there were four vibrators moving around inside her up until we got in the elevator and she pressed a button. The doors of the elevator closed, and she loudly moaned, and her body trembled. "I'm Cumming Mistress," Little Star cutely said, and I grinned, reaching out to her and grabbing her breast with the trench coat, stopping me from directly grabbing them. I could feel the nipple torturer under it, and I made her groan as I massaged her breast.
"Now, Little Star. You will tell me each time you cum, and you will proclaim it. You will shout it every time, and I will punish you tonight if you fail to. I cannot wait to see what a mess you will be once we finish dinner." I said, and I felt her face in the palm of my hand, now stoking it with my thumb while the other held her breast, massaging it slowly. "Thinking on it, I believe you no longer need the coat. Strip and walk with me, Little Star."
The elevator doors opened, and I looked at her as she opened the trench coat and slipped her arms out of it, allowing it to drop to the floor in a puddle. I smiled as I saw her in those blood-red panties that covered nothing. The nipple clamps continued to torture those nipples, and four wires moved up from her thighs that were dripping with liquids from her pussy where two of those pink wires disappeared into. The blood-red panties were soaked, and two more pink wires disappeared into the depths of her ass. The sound of vibrators clashing together inside of her was barely perceptible and my fingers touching her clit made her shudder.
"Mistress!" Little Star cried out, pleading. My fingers continued to tease it, and a second later, Little Star cried out loudly, "CUMMING MISTRESS!" Fluids sprayed out, and I grinned, stepping back as she wet the trench coat and my fingers.
I slowly brought those fingers up to my lips and sucked off the sweet and acidic liquid from my fingers. "Tasty," I said, "I wonder how it will taste on dinner?" I asked, and I saw Little Star trembling from the orgasm.
"Please, Enjoy, Mistress," Little Star said, huffing harshly, "I believe dinner should be ready for us once we enter, although it might be a little cold."
"That is fine," I told her, continuing my previous comment, "I can always warm it up with your pussy juices," I told her, and I stepped back and finally out of the elevator, leaving my backpack behind in the elevator.
I found myself back in her house, which I had seen a week ago, but there were some light changes. The dining table was no longer as large and was set with two silver platters on either side. I smiled as we would be inches away from each other, and I walked over with Little Star following me as I reached the table.
I quickly moved things and ensured that Little Star would be closer to me. I moved the plates to reach down to her pussy and stuck my finger into it. I grinned as I turned to Little Star and motioned to the chairs. "Let us eat together," I said and sat down and lifted the cover off the food.
A large plate of food appeared before me, and I turned to Little Star as she moved slowly around the table. I saw each step for her was difficult as the constant buzz of vibrators sounded in the room. I grinned and lifted her lid to see a much more modest-sized portion than my own. "Well," I said as I watched her sit very slowly.
"Mmmm," Little Star moaned as she sat down, and I picked up a fork with my left hand. I slowly dug into the food and moaned as the taste entered my mouth. "is it good, Mistress?" Little Star asked, and I nodded.
"Although I think I might need some more from your honeypot later to make it exquisite," I told her and watched her blush. "Now, Eat, Little Star; you will need the calories for what I have in store for you later."
Little Star blushed, and we ate together. After a couple of bites of food, without a word, I reached down to where she was sitting. My hand dove to her clit, and I pressed my index finger against it. "So this Friday," I began, "I will be talking to a lawyer. I will listen to some advice and have a company created for you to put the money into. I will then invest it for the future, Little Star. But with this visit, you know how much you owe me. But don't get me wrong," I said, turning to her and seeing a business look, and I pressed my finger against her clit and used my elbow to jostle the nipple clamp making her squirm and groan. "I do this because I enjoy it. Not because of the money. You could be paying me hundreds of thousands; if I didn't enjoy it, I wouldn't show." I told her.
The blush on Hilda's face turned very dark, and her pussy gushed fluids, and I could tell she was near the edge. My hand lifted up, and I slapped her clit with the tip of my hand. "Cumming," Little Star said with some drool coming from her mouth; her body shuddered, and I felt a small squirt drip down onto the chair.
"What a good slut for Mistress," I commented and took another bite of food, slowly retracting my hand as I finished chewing. I swallowed and opened my mouth before licking my fingers. "Delicious."
Little Star seemed to be having a problem eating. Time went slowly, and I continued to tease her from time to time until I finished my food with her a moment later. In total, I made her cum five times while we ate, and my cock throbbed. My skirt didn't cover that my cock was hard, and my breasts were now holding my cock between them. I smiled, looked around to see the black bags beside the elevator, and realized I had completely forgotten about them as I played with Little Star.
"Let's go upstairs," I said and stood, leaving the dirty kitchen. Little Star followed me on trembling legs, constantly looking down at my cock. I could see what she wanted and could tell it was a growing need to feel my cock inside her. She must have been thinking about it all week as I had left her trembling from my session last week.
I grabbed the bags in one hand and pressed the up button on the elevator. Little Star entered with me, and I grabbed a nipple clamp, and she cried out, "OW!"
I twisted it a little, and she groaned as the pain assaulted her. "You are so cute in pain," I told her, "I cannot wait to make you scream upstairs. Your punishment will be very enjoyable to me."
"Mistress, Please, forgive me," Little Star begged a little, and my cock throbbed. I felt a smile grow, and I looked down at her.
"No," I told her, "I want to punish you. Now, what do you want?" I asked her, "Knowing what I want," I clarified.
Little Star froze, looking up at me, and I smirked. My smile was sadistic, and Little Star trembled as she was reaching another peak. "Come on, tell me," I said, and I twisted the clamp on her nipple.
"MMMM!" Little Star complained with a closed mouth. It took her a couple of seconds, and she looked away, "I want you to punish me, Mistress," Little Star finally said.
"We are both in agreement then," I told her and reached into the bags and quickly found the skimpy outfit. I grinned, took it, and continued, "I am going to go freshen up in the bathroom and change," I said, "You will be ready inside the bedroom. You will have all the toys opened and ready except the condoms. Those will stay boxed and ready for me to open." I ordered her, and I stepped back, grabbed my backpack, and exited, "See you in a couple of minutes, Little Star." I told her as I walked away, "I look forward to playing with you tonight."
I walked into the small hallway and entered the center door out of the three knowing it was the entrance to the bathroom. As soon as I entered, I closed the door and grunted as I felt a throb in my cock. I had been hard for a long time without release. I had been teasing and playing with Little Star so much and her mature body that I had been able to distract myself. My cock was in need of serious relief, and I even floated the idea of jerking off for half a second, only to shove it out of my mind. I was almost there where I could release my lust and completely destroy that pussy that I had been tenderizing for the last couple of hours. It would be glorious once I pushed my cock into her pussy. Her body would be so moist and ready, and I wondered how much it would tighten on me.
I shook my head and left my thoughts behind me. I needed to change and back into things; Little Star was waiting. I quickly took off my backpack, skirt, and panties before taking off my shirt. My bra left a couple of seconds later, along with my shoes and socks. I left them in a small pile, and I turned to put on the one-piece outfit. It was tight, and I grinned as I looked at the outfit in the mirror.
Up the center of my body was a black polyester fabric with thin strings around the back every couple of inches. With the size of my breasts, the stings had to go around and just made my breasts seem large as they couldn't go around them. I looked ready to play and up the center of the fabric. The only thing about it that could be called an outfit was my hard cock going up into the cleavage of my breasts, where they ran through. My cock throbbed, and I was hardly covered. I quickly took a picture of myself and sent it to Crystal before setting my phone aside with my clothing and backpack.
I stretched a little, then grinned viciously as I stepped toward the bedroom door and opened it.
Little Star was sitting on the bed, her breasts still with the painful clamps, and her face flushed red as I opened the door. Beside her, a vibrator, anal beads, anal plug, rope, lube, and a paddle lay. It was simple, and I grinned as the rest of the bags were tossed aside. I stepped forward and said, "Ready for your next punishment, Little Star?" I asked.
Little Star shook her head, and I grinned viciously, "That is too bad," I told her and grabbed the paddle, "I will increase the strikes by five to help you relieve your worry. For now, it will be twenty strikes to your ass and five with the studs mixed in for twenty-five strikes from the paddle." I told her as she looked distractedly at my cock.
Small tears welled in her eyes, but she nodded, "Yes, Mistress," Little Star said, her voice pained.
"If you are good Little Star," I said to reassure her, "You will be begging for this again next time. I assure you will only remember tonight with the fondest of memories thinking about what I will do to you tonight," I said as I closed in on her picking up the paddle.
Little Star nodded, and I cupped her face and leaned down to kiss her. I surprised her for a moment before she gave way to my advance and melted to my touch. When I broke the kiss, she looked so ready to be fucked, and a line of drool trailed from my mouth to hers, only to break and land on her breast as it broke. "You will stand up and lay your stomach across my lap, Little Star, for these strikes. Once I start, I will not stop until the strikes are finished. Do you understand?" I asked her.
Little Star nodded, and I turned and sat on the bed with my cock throbbing. I wouldn't be able to hold back much longer as it was starting to pain me how much I wanted to fuck that pussy. The Vibrators sounded in her pussy as they rumbled against each other, and she stood on shaky legs. She slowly brought herself down onto my lap and groaned as gravity moved those clamps down on her nipples. I could see her bit her lip, and I stroked her blonde hair with one hand while the other filled to the smooth side of the paddle.
"Ready?" I asked Little Star.
"Yes, Mistress," Little Star replied, although I could hear her nervousness as she said it.
My hand couldn't wait any longer, and the strike came down on her juicy mature ass. "AH!" Little Star screamed out, and I wasn't going to make her count this time. The Second stroke of the paddle came a second later, and she cried out as I counted in my head.
Three, her scream was so good as she cried out, and my cock throbbed.
Four, Five, flip it over for one of the studded side. The sudden increased pain made her squeal, and she tried to move away while my hand held her in place. Her shaky movements, along with the pleasure from the vibrators, made me witness a squirt from her juicy pussy. "Cumming?" She exclaimed as her pussy sprayed the side of the bed, and the paddle came down again on the smooth side for a sixth strike.
"Why did I cum?" Little Star begged to know as the vibrators rumbled inside her, and I answered her question with a seventh, eighth, and ninth strike to her ass, making it ripple in a way that was candy to my eyes.
"Because you are a Masochistic Slut," I replied to little Star and followed it up with the smooth side's tenth and eleventh strike. Her legs were trembling, and her ass beet red as I brought the paddle down for a twelfth stirk, followed by me flipping it and bringing down the studded side.
Multiple things quickly happened, as I did. Little Star screamed, and her legs gave up, putting more of her weight on my lap as I held her in place. Her pussy then released a torrent of liquid as she squirted, followed up by a stream of yellow as she began to cry with fat tears as she released her bladder. I didn't even attempt to stop her pissing herself and followed up with the thirteenth, fourteenth, and fifteenth strike of the smooth side as she pissed herself.
Little Star screamed and tried to escape again but never shouted the safe word. I followed up with the sixteenth and flipped it over for two solid studded strikes.
"MISTRESS! MERCY!" Little Star cried out, and I quickly followed up with the last four smooth and the final studded, leaving Little Star dazed and maybe seeing stars.
On the other hand, My cock was throbbing in need to push her down and penetrate her as she breathed heavily. Her pussy was juicy and ready to be taken, and I reached down and pulled the vibrators out of her pussy. "You did such a good job, Little Star. Time for a reward," I told her and reached for the rope. I grabbed her arms, put them behind her back, and tied them together. Little Star was too busy reeling from the punishment even to notice, and I picked her up and placed her on the bed, completely forgetting about anything else.
My cock was hard, and I reached out and grabbed the box of condoms on the nightstand and ripped the box open in one move. I wasn't in a place to control myself anymore. I looked at the blonde Russian woman with nice breasts being tortured and the vibrators hitting the floor from her leg. Two remained in her ass, sending constant pleasure from the woman that had cummed more than ten times before I even got to cum for a second time tonight. My lust was at its peak, and I needed to release myself. The condom packed was torn, and I think I set a personal record for putting on a condom down the length of my cock.
Heavy looking fuck me eyes stared up at me, and I almost growled with impatience, even lining my cock up to her pussy and thrusting into her dripping wet cunt. Nervana greeted me, and her pussy tightened up while the vibrators made her almost seem like a cock sleeve as it sent a shiver of pleasure through me. Each fold was a moist wreak marinated in hours of juices meant to accept me, and my head blanked.
I pulled her legs up, pushed them off to the side in a giant V, and positioned myself above her. My hips began to move before I even told them to and her screams were the background noise to my grunts of need. I couldn't stop myself as she screamed out the pleasure she felt as her breasts bounced around as I pushed her into the mattress with my hips. She bounced back up, and my cock continued to fuck her brains out as I continued to thrust into her mindlessly.
I lost myself in the pleasure of her pussy, and her breasts bounced around, sending pain from the nipple tortures as she was assaulted with pleasure from my rough fucking. "MISTRESS! MISTRESS! CUMMING!" She Screamed. I felt her cunt tighten, and liquids hit my hips. I wasn't done, though, and I continued even as she came. I quickly reached the edge when Little Star screamed again, "CUMMING AGAIN, MERCY!"
Mercy for her pussy didn't come, but my cock continued to, and I reached my peak and cried out, "Take it, Little Star," I cried out without thinking, "Take Mistress's cum, you Slut!"
Rope after rope entered her womb with only the thinnest of latex, stopping it from impregnating her cougar pussy. Her cry of pleasure sounded throughout the room, and I rolled my eyes back as I continued to move my hips throughout the orgasm. Little Star was moaning under me as I continued moving my hips back and forth until I finished ejaculating, where I pulled back, and my mind returned to me. I pulled out and grabbed the condom pulling out a very full condom of my semen. I tied it up and smiled, putting it off to the side without thought or care at the moment for where it was.
"That was needed," I told the drooling woman under me and reached for another condom. "I don't care if you're ready for round two." I continued as I slipped on the condom. The sound of vibrators hitting the floor and inside her cunt was only joined by the low moan she was releasing. "I'm coming in for another," I said as I finished slipping the condom down the length of my cock.
I really enjoyed Hilda. I thought as I lined up my cock; she was really expressive in pleasure as she laid there, her mouth open, drool dripping out of it, her legs almost at the point of splits, ready for me to move again as I grabbed her by the hips this time and forced her pussy back onto my cock. I would never give this bitch up. Money or not, she was fun.
Her scream sounded the bell of round two, and the night was still pretty early, with many hours left.