Babysitting - the Little Red Monster

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Kara learns new ways to pleasure herself.
5.3k words
4.64
14.1k
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Part 2 of the 3 part series

Updated 06/17/2024
Created 05/17/2024
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I was walking from my house to the Wasserman's. It was the fifth or sixth time I sat for them. I had only met them two weeks before, but felt like I knew them intimately. In truth, I knew them more intimately than I knew them personally. I had been watching their sex videos since I accidentally found them the first time I babysat for them. I was able to transfer dozens of files and hundreds of pictures to my laptop. I watched videos from when they were married to one that seemed only a few weeks old.

I was geeky in school and had only really fooled around with boys for the past year or so. I had yet to go all the way. I was pretty naïve in sex knowledge, with the exception of the stuff on the internet, which was hit or miss. These videos were different. These were people I knew, people I talked to. Victor, Mr. Wasserman, was hot. Jennifer, Ms. Wasserman, was sexy.

Mr. Wasserman was so hot I got wet just seeing him. There was something beyond his movie star good looks. I cannot say what it was, but I was obsessed with him. One of the movies was him masturbating to climax. I had watched that so many times I had the timing down to I could almost cum with him. Then, watching Mrs. Wasserman, I learned different ways to please myself. Watching her and mimicking what she did brought me to new levels of ecstasy. I also learned what her hubby liked. I would rub myself and pretend he was fucking me. Screaming my head off, pretending his cock was in me. Doing things, he told her he liked.

My mind played the video of him in my head as I strolled to their house. I had gotten myself worked up as I dressed to see him. I decided on a knee-length dress and a tight sweater that would hug my breasts, making them look bigger. It was warm in late January. But the beach area of Virginia never really got too cold. Of course, I decided against underwear and felt the cool air ride right up my legs and against my bare privates. I had my backpack and laptop inside. I had a change of clothes in case something got spilled. I carried something to sleep in case they invited me to stay over. I imagined Mrs. Wasserman asking me to stay the night. Then, in the middle of the night, Mr. Wasserman takes me. As the movie played in my head, I could feel the wetness growing between my legs. I squeezed my thighs together as I walked and could feel a tingle between my legs. Wow, I didn't even get to the house, and I was soaked. I walked up to the front door. I knocked.

"Hello, Kara," I jumped and shifted as a hand touched my shoulder. The voice came from behind me. Mr. Wasserman startled me as he walked around from the back of the house. "Oh, I'm sorry. I did not mean to scare you."

"It's ok, Mr. Wasserman. I just expected someone to come from the door. I wasn't ready to be jumped from behind." Oh god, please jump me from behind and take me, I thought. My eyes looked up and down at him. Even in wearing sweatpants and sweatshirts, he was hot.

"Well, you need to work on your situational awareness. I could have had you restrained and in my control in seconds." Oh god, if only, I thought, feeling a tingle. "I called to you from the sideyard. I thought you heard me. Must be daydreaming."

Dreaming of you restraining me and controlling me now. "I guess. I was working on a computer problem in my head."

He opened the door. We walked in. "Speaking of computer stuff, take a look at my laptop in my office if you would. I've been having issues accessing different files. Not sure if it's networking or a connection problem."

"Will do, sir."

"As before, I'll pay you extra. And Kara, knock off the Mr. Wasserman and the Sir, shit. Call me Victor."

"I know it just takes some getting used to. Parents raised me to be polite."

"Well, they did a good job. But I insist." He turned to the upstairs. "Joey, where are you."

"He's up here with me, dear." Ms. Wasserman replied.

"Ok, Kara is here."

"Oh, she's early; send her up here."

"Her Majesty would like you to join her in the bedroom." He made an exaggerated gesture of pointing toward the stairs.

"Why thank you, kind sir," I said, bowing slightly.

I headed up the stairs to the master bedroom. I saw Joey, their son, sleeping on the big king-sized bed. The baby was in a bouncy chair on the floor. Ms. Wasserman was at a mirrored vanity table, wrapped in a towel.

"He fell asleep as I was running the hair dryer. Can you believe that? Loudest noise, and my son falls right to sleep. "She glanced in the mirror at me as I came in. "I swear males can fall asleep anywhere. Victor is the same way."

"Hi Mrs..." She glared at me. "Hi, Jennifer." I smiled.

"Thank you," she smiled. "Whenever you say Mrs. Wasserman, I feel another wrinkle appear somewhere. I'm glad you are here. Help me pick out an outfit." She led me over to the closet. She had two dresses hanging. She dropped the towel and stood naked in the closet. She started to sling one over her body. She was very comfortable with her body. This was not the first time she had casually stood in front of me naked. I took in her large breasts and hairless pussy. I couldn't wait for the kids to go to bed. I stared at her naked pussy for a moment debating my pubic hair as she struggled with the dress. Ever since I saw her, I debated whether to shave my hair. I had trimmed it back but still had a blond fuzz covering myself. My mind snapped. I reached out and helped her get the dress on. She looked amazing as she always did in dresses. This was a green strapless that showed her abundant cleavage. She looked at me and then at the mirror.

"Very nice," I said.

"Yeah, let's try the other one." She stripped the dress off in seconds. "It's always easier to get off than on. Of course, that goes for dresses," she laughed. She stood naked in front of the mirror and paused, looking at herself. Her eyes met mine in the mirror. That is a lovely sweater you are wearing. It accentuates your chest. I bet you turn all the boys' heads in that."

"A couple." I smiled.

"Any special boy in your life got your eye?" Your husband, I thought.

"No, I'm too busy for boys. I wanna make money so I can travel this summer."

"Ooooh, yes. Find yourself a good boy from some exotic location and fuck him like there is no tomorrow. I remember a boy I met once on vacation in Florida. I think I spent half the vacation fucking him." Her one hand casually rubbed her breast, and the other slid along her bare mons. Oh my, I thought she would put on a show for me right now. "You make sure to find a good one with a nice fat cock to please you." She smiled at me.

"Well, if I find the right one, I'll let him take my virginity."

"Oh my, a pretty young girl like you, a virgin. Well, you make sure it's the best-looking one then. And you make sure he treats you right. Get an older boy. When you are ready, tell him he better make it special. Make him spend some money on a hotel. Take your time, find a special boy, and enjoy it." She started putting on the second dress.

I found a special boy, and he's older, and he's got a nice fat cock. He's remarkable, just like your husband. I thought. Now, I just have to figure out how to make it happen.

"Yes," I replied, "I just haven't found someone I want to do it with. I was almost ready with the last boy I dated. But he couldn't wait and slept with another cheerleader."

"Well, you got lucky. He sounds like a jerk. What do you think?"

This dress was also perfect. The red color played well off her tanned skin and dark hair. "That is the one," I said. "It looks great with your skin and dark hair. Something about it pops."

"I agree. This is the one. Ok now, Panties or no panties?"

I felt my nakedness under my dress. "Well, he did not get to take advantage of your commando outfit last time. Maybe try again this time."

"That sounds exactly right," She said with a devious smile. Joey made a noise from the bed, and we saw him sitting up.

"Hello, sunshine," I said to him. I walked over and reached out to him. He jumped into my arms. I'll take him and the baby down and let you finish getting ready." I grabbed the baby and headed back downstairs.

Victor was doing exercises in the living room: push-ups, mountain climbers, and jumping jacks. Joey scrambled down and joined his daddy. I took a seat and watched, trying to contain my lust. After a few minutes, he finished and said he was headed to get ready. He was going up as Jennifer was coming down. I heard him say he was jumping in the shower. Oh goodness. How can I get up those stairs to watch him get ready?

Jennifer and I talked some more. She gave me advice about not rushing into anything. It will be more enjoyable to lose my virginity to someone I like. She spoke of the boy she had been with. I could see the joy in her eyes when she spoke. Twenty minutes later, Victor came down dressed to kill.

"It's not fair that it takes us hours and them minutes to look so good," Jennifer said.

"I disagree," Victor said, "You looked good before you started. I only look good after twenty minutes. If I went another twenty hours, I could never look as good as you did when you started."

"Flattery does not make it fair. But thank you," she smiled.

"Besides, I cut corners. My suit was already decided on; I only had a few pairs of shoes and skipped underwear, so I had an advantage." He smiled, winking at her.

"Well, that's cheating. But sexy, so I'll let it slide." She winked at me and then headed toward the door. He fell in behind her. They headed out.

The kids and I played for a couple of hours. The baby lay down. Joey wanted to stay up. He finally fell asleep while building with blocks. It was the cutest thing. I took a picture and sent it to Jennifer's cell. I carried him to the bedroom. I laid him down. I strolled to Victor's office once I was sure he was settled. I sat down at his desk chair.

The leather smell wafted through my nostrils. I clenched my legs together as I felt a tingle. I booted up his computer. After a few minutes of messing around, I figured out the issue. It was a problem with the security software and the network. I made some changes and documented what I did. I rebooted the system and ensured that all worked correctly. It did--another successful computer fix.

I checked some other settings on the laptop. Then I had an idea. I did a video search. In a matter of moments, I discovered another folder of videos. This was the mother load. I ran downstairs and grabbed a couple of thumb drives. Back up in a flash. I copied a new stash of Wasserman porn.

While the files were copying, I walked to their bedroom. I looked around. I saw the sweatshirt Victor was wearing earlier. I grabbed it off the pile of laundry. My hand brought it to my nose and inhaled deeply. His scent filled my nostrils. The T-shirt he was wearing was lying on top. I grabbed it. It was covered with his sweet, musky scent. My legs went weak as I breathed in. The dampness between my legs was starting to trickle down my thighs. I looked around the room. My eyes stopped on the nightstand. A flicker from a video of Jennifer pulling a red vibrator from the drawer flashed through my mind. I walked over. My hand shakingly opened the drawer. There were several different adult toys in the drawer. I grabbed the red vibrator. I also grabbed a bottle of lube. I looked at their bed. I shook my head and headed downstairs. On the way, I grabbed two towels from the closet.

In the living room, they have an oversized ottoman. I put the towels down and stripped my clothes off. I put Victor's sweatshirt on and his shirt across my face. His aroma invaded my nostrils. My top sat on the couch next to me. I pulled up a file from my newly copied treasure. As Victor stripped Jennifer's clothes from her body on the video, my finger slid down my belly. I ran my fingers through my blond pubic hair. Jennifer's bare pussy was exposed on the screen. My mind again debated whether I should shave.

My finger slid down across my hood into the wetness below. I swirled it around, feeling the tacky mess that had grown over the last few hours. My pubes were slick with my juices. My finger felt so good as it slogged around my sticky folds. I slid my finger back up, glancing over my exposed clit, sending shivers dancing across my body. I brought my finger to my lips and stared at the image of Victor on the screen. I seductively licked my glistening-coated finger. I sucked on it like it was a cock. I was rewarded with the taste of my tangy juices.

I squirted some lube on my fingers and slid them back into my wetness. Goose bumps ran across my flesh as the cool gel touched my sensitive lips. The lube allowed my fingers to skate around my labia. The heightened sensation of the slippery gel started a tightening of muscles around my body. A warmth grew in my lower belly. Oh fuck. I was so close. Victor was pumping his sweet cock in and out of Jennifer. My fingers started pumping in and out of my tender vagina. With the lube, I could fit three fingers inside me. My muscles clenched and tightened on the

penetrating digits. More pleasure shot around my body. My other hand squeezed my breast and pinched my nipple, sending delight cascading around. I was so close. The tension inside me was growing. My fingers pumped in and out while my hand touched my button. I spread my flesh, exposing my swollen clit. Lubed fingers stroked while the other hand pressed deeper inside me.

The tensions peaked as I rubbed the lube on the raw flesh on my exposed button. My pulse quickened. My breath held. I exhaled sharply, "Fuck Yessssssss. Fuck me, Victor." My fingers barely circled my clit twice before the orgasm burst from my belly. Extasy raced through every vein in my body. My fingers desperately tried to stay on my swollen clit. My muscles clamped on the three fingers pushed inside me, adding to the intense orgasm I was having. I felt the wetness flood out of between my legs. "Fuck, Oh Fuck, Oh Fuck" I yelled. I breathed in, and Victor's odor heightened the experience. My mind pictured him inside me. His hand rubbing my clit. My body was shaking. All my muscles tensed and tightened.

The orgasm washed over my body again and again. I felt every nerve screaming in happiness. Then it echoed one or twice and then settled. My body jolted each time. The waves of pleasure lessened and then died off. My fingers were still jammed inside me. Fluids were leaking out of my dirty pussy. My breathing returned to normal. My body stabilized. The towel was wet. My hand was soaked and slick. I grabbed my breasts and squeezed as I tried to bring my mind back from the orgasm.

The next video started with Jennifer's lips sucking on Victor's hard cock. I looked at my laptop and saw the vibrator sitting next to it. I stripped off the sweatshirt and put the shirt along my neck. I spread my legs wide and covered my hand with lube. I slid my fingers down and liberally slathered lube all over myself. As Jennifer sucked her husband's cock for the camera, my fingers pulled and tugged at my labia. I coated them with the cool gel. "I'm getting this pussy nice and wet for your fat cock Victor," I said to the image on the screen. My fingers rubbed and teased the swollen, sensitive lips. I slid the vibrator down and turned it on.

I had never used any toys before. I had messed with the shower head. It was ok. I humped a pillow. I got off on that, but no more than my fingers. That was just a pleasant sensation of something else between my legs. This was my first time using a vibrator.

Everything was swollen and excited and sensitive from my previous orgasmic bliss during the first video. Now lubed and teasing myself in my new excitement, shivers were already bouncing across my body. The residual energy from the previous ecstasy was recharged. The tingle began almost immediately. The moment the vibrator touched my clit, my pleasure increased tenfold. That buzzing little monster touched my button. Fireworks went off inside me. I quickly slid it into my folds and felt the energy zoom through everywhere. My hips bucked at once. I spread my legs wide and arched my back as the energy flowed through me. The pulses hit all the right spots. "Oh god, Oh fuck, Oh Victor." My body started shaking. The energy built in my tummy. I pulled it back up to my clit. I ran it in circles, pushing its way past the protective skin. I felt the hard plastic hit my button. Somehow, I accidentally hit something. The little monster sped up. Every muscle in my body tensed. I froze as the electricity peaked. The pulsating red plastic shook the raw nerve between my legs. Every muscle spasmed with joy.

"OOOOOOOOOOOOOOOOHHHHHHHHHHHHHHHHH FFFFFFFFFUUUUUUUCCCCCCCCCKKKKKKKKK!!!!!"

My body went into overdrive. The massive orgasm shook everything. I felt my pussy gush with fluids. My hand squeezed my breast tight. The pain was barely discernable over the pure ecstasy that I felt. My vision blurred. I stared at the video but could not tell what was happening. My hand held the hard red vibrate against me for what felt like hours. The earthquake of tremors hit every inch of my body. Somewhere in my mind, a distant part of my brain told my hand to move, and I slipped the vibrator between my legs. The tremors continued, and my body shook, but the intensity lessened. I lay there, legs splayed across the ottoman, body trembling with aftershocks of excitement for a few minutes. The buzzing beast was still in my hand but away from my wetness. My body recovered as the twitching subsided. I caught my breath. "Oh fuck." I mumbled. My mind slowly came back into clarity.

I began to collect myself. I closed my legs and sat up. I was dizzy. I brought the buzzing vibrator up before me and hit the button to turn it off. The vibration increased. It had five more levels before it turned off. Dear god, I was only on level two when I exploded. I stared in disbelief at the little red pleasure device. This was level-up excitement. It was coated in my cum and lube. I licked it and realized that lube tastes nasty. One towel was soaked, but fortunately, the second was only halfway through. I had gotten some on the floor. I dabbed at it with the towel to dry it up. Thank goodness there was no color to my mess. I was completely soaked. I pulled Victor's sweatshirt off. I walked upstairs to their bathroom. I dropped the sweatshirt and shirt in the basket. I wiped the red toy off, replaced it, and put the lube back into the drawer.

I went into their bathroom and turned the shower on. I washed myself up quickly. Part of me hoped that Victor would walk in while I was in the shower washing behind the glass door. But no such luck. I dried and redressed. I returned to the living room and sat in the oversized chair. I gathered my laptop and turned on the TV.

Victor and Jennifer got home late. It was past two thirty. Jennifer was pretty drunk. She entered the living room and sat on the ottoman facing me. She was going on about a bar they had been at and a game they had played. She was skipping points, and the story took a lot of work to follow. Victor, who was also pretty drunk, had gone upstairs when they first came home. He came down wearing the sweatshirt and a pair of gym shorts. I got excited seeing him in that sweatshirt. I know I had gotten my mess all over it. I imagined him smelling me. Jennifer asked me to please stay the night. She felt they were in no condition to care for the kids. I happily agreed. The vision of Victor joining me in bed danced through my head as she talked about something new. She took me upstairs and showed me the guest room. She was stripping off her dress as she spoke to me. She walked out half-naked toward the master bedroom. I changed into my sleepwear. I went downstairs for a glass of water. When I got to the kitchen, I saw Victor standing behind a counter, looking down.

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