Gay Sex

Searching for the Baby-Sitting Hideout

Kara begins her babysitting job and finds something unexpected.

Spankmasters
May 17, 2024
16 min read
Babysitting - Finding the Stashmasturbation
Babysitting - Finding the Stash
Babysitting - Finding the Stash

Searching for the Baby-Sitting Hideout

In high school, I was a computer geek who was also part of the theater. I didn't start to develop until my junior year. With my petite stature and flexibility, a friend suggested I try out as a flyer for the cheer squad. This was when I started getting attention from boys. By this time, I had my sights set on college and maintaining good grades.

I managed to get accepted into college, and with the holiday season approaching, I decided it was time to start earning money. After working at a waitressing job, I was eyeing a bartender position. I was saving every penny, looking for more opportunities to make money.

One day, my mom informed me that a new couple in the neighborhood was looking for a babysitter. I used to babysit for them, but the kids had grown up, so I had passed the position on to other sitters. Now that I was free on Friday nights, I approached them about giving it a shot again.

The Wassermans lived a short distance away, about a fifteen-minute jog from my parents' house. Their kids were a young two-year-old and a six-month-old. I thought babysitting would be an easy way to earn some extra cash.

When I arrived, Mrs. Wasserman greeted me, and we played with the children while she got ready. We chatted about school and different plays we had been in. She asked why I was so focused on work and college and not socializing. I explained my relationship history and priorities. She praised my ambitions and it led to discussions of college. She reminisced her college days and predicted I'd enjoy it as well. Our laughter echoed in the living room.

Before Mrs. Wasserman left, she left me with the kids in the living room.

While playing with the two-year-old, Mr. Wasserman entered the room. I couldn't believe how good-looking he was. He was dressed in a black suit, a blue tie, with dark blue eyes and short brown hair. Tall and well-built, he dwarfed me.

"Are you okay?" he asked when he saw me coughing. I had been trying to hide my surprise.

"I'm fine, must have inhaled something," I forced myself to laugh. He extended a hand to help me up, which left me feeling unbalanced.

"Sorry," he said, "I don't always know my own strength."

"It's not a problem," I chuckled, "I'm just lighter than I look."

"Trust me, you appear to be the exact weight you should be. You look fit and healthy." His eyes roamed up and down my body, making me stand up straighter. I was wearing a T-shirt, shorts, and a sports bra. It was a pleasant feeling to be appreciated for my appearance after years of being with an unappreciative boyfriend.

"I like to run and work out," I told him.

"Then you should keep it up. You have a nice body. I could see how toned you are. You shouldn't let anyone make you feel inferior, no matter how they treated you before."

"You're kind of right," I agreed.

"Do you like to use weights?" Victor asked.

"No, but if you have any, I could definitely use them," I said, still shocked by his thoughtfulness and generosity.

"I do. My garage is set up as a gym. You're welcome to use it when the kids are in bed."

"Thank you for your offer."

"Did your wife show you the house?"

"No, I was just keeping an eye on the kids."

Mr. Wasserman picked up the youngest by the legs and held him. "Joey, why don't you take Kara around the house?" he asked. The baby stretched his arms out, accepting my hand. We made our way through the Wasserman home.

The house was incredible. It featured a basement with a modern entertainment center, a personal movie theater, and a room with a pool table. Additionally, there was a gym set up. The house was equipped with advanced voice-activated lights. Every aspect of this place was premium. I was briefed on the entertainment system, explained how it was linked to his computers. "We have a large collection of movies ranging from popular ones to those for the kids on my PC's hard drive. You can access any of them from any computer connected to Wi-Fi. Do you have much experience with computers?"

"I'm planning to study them in college. I'm somewhat of a computer geek."

"Wow, I don't know anything about computers. Do you ever play online games?"

"Yes, I do. But I'm more into programming and networking aspects of it."

"Oh, that's awesome. I'd love for you to take a look at my system before the children grow up. I'm certain it has many vulnerabilities."

"Sure, I can do that, if you want me to."

"Absolutely. I need your assistance. My brother set up the computer system, and I have no clue how it works. I just know I can watch whatever movie I love on TV."

"In your free time, I'll check it out and inform you."

"Great, I'll compensate you for your troubles."

"Oh, no need; I enjoy taking care of the children and solving technical issues."

He stopped and turned to me, seriously stating, "Kara, never undervalue your skills and time. If someone is willing to pay for your services, never offer them for free. I am a businessman. I don't give away money."

I was at a loss for words, "Well..."

"Listen, my dear, people often fail to realize their potential and undervalue their worth, charging far too little for their abilities. Always accept payment when someone offers you cash for your talent. Give your time away only for charity in specific instances. I generate a significant income. I am not a charity. I'll pay you for your time and work."

"Okay."

He gave me a tour of the house. The backyard had an indoor pool, a hot tub, a pool house, and a large workshop. He referred to it as his mancave. We proceeded upstairs to the children's rooms. He described how to set up a monitoring system for the baby. Then, Joey's room had a monitor that would enable us to hear him. His wife had an office upstairs, and there was a spare bedroom. He pointed to the master bedroom. Joey ran off, maneuvering the door open.

Mrs. Wasserman was standing in front of a vanity, only sporting her underwear, drying her hair with a towel. I hadn't realized that she had a well-sculpted body. She had been dressed in sweatpants and a loose top. However, right now, her toned, athletic legs, and exposed, voluptuous buttocks in those skimpy G-string panties were now in plain view. Her 34D assets in the mirror caught my attention.

"Mommy!" Joey announced. She turned and squatted, picking him up. Aware of my presence, she adjusted the towel, covering herself.

"Sorry, darling. I was just showing Kara the house," he said.

She walked towards the door adjusting her towel as she went, "I'm certain Kara has seen people without clothes on in locker rooms and such." She handed Joey to him. "Go down the stairs and entertain the little ones. I'll be down soon to dress up. I only need a few minutes to get ready."

"Sounds good, darling. But honestly, I find you equally stunning with or without clothes." They exchanged a passionate kiss.

"Well, maybe I'll be the star attraction at your office party wearing this towel and minimal clothing." She slipped back into the bedroom.

We descended and continued playing. Victor showed me the kitchen with all the premium appliances. He discussed the children's routine, their snacks, meals, etc. "The baby usually falls asleep around 8 PM. Joey follows about 30 minutes later. While asleep, he prefers a show on television. So, by 8:30-9 PM, you will be lazing about, merely listening if there are any issues. Feel free to rent a movie or connect your computer to the system to unwind. The password is located on a piece of paper on the fridge."

"I'll examine the system after the kids go to bed and share my opinion."

"I'll pay you extra from when they fall asleep to the finish of your shift. Agree?"

"It sounds fair."

Mrs. Wasserman made her appearance. She looked stunning. She wore a skintight, blue gown with heels. The dress showed ample cleavage. The back dipped low, almost reaching her rear. Her tanned skin complemented the hue of the dress. I wished I could rock a dress like that. I couldn't believe this was the mother of a six-month-old and definitely not of two.

"Wow, baby. You still take my breath away," Victor remarked, blowing a whistle. "Everyone's eyes will be on you tonight. People will want to snap pictures with you. So they have a picture of the hottest woman in the scene." He walked towards her and kissed her. They made quite a couple — him a Greek god, and her his goddess.

"You look astonishing in that dress, Mrs. Wasserman," Kara said. "The both of you look fantastic together."

"You can call me Jennifer, Kara. Mrs. Wasserman reminds me that I'm nearly forty," she replied.

"Oh, you seem much younger than that, Jennifer. I'd definitely card you if I served you dinner at your table," Kara smiled.

"Thank you, Kara."

"That makes my forty-six-year-old self an old man with my young, sexy partner."

"No, sweetie. I would've thought you were in your late twenties."

They said their goodbyes to the kids and left. I held the infant while Joey stood next to me as they walked to the car. I couldn't stop staring at Victor's derriere. Everything about him was so appealing.

I looked after them, then put the kids to bed. I went to the media room and sat in a cozy armchair. I hooked up the monitors to the speakers and listened to the kids snoring peacefully. I opened my laptop and logged into the system.

I went to town, tweaking a few settings and securing a few things here and there. I jotted down my suggestions and notes. I also improved the Wi-Fi, since it was broadcasting to the outside world. Overall, I spent nearly two hours tinkering with the system. I recorded it all in my work file.

I popped in on the kids again. I wandered around the house checking out their photos. They both looked smoking hot. There was a picture of them at the beach in bathing suits. Victor had chiseled abs, while Jennifer's bikini barely covered anything.

My libido was raging. To distract myself, I decided to watch a movie. I searched for .MP4's. Loads of files popped up. Many kids' movies. I started examining folders. The titles were everywhere. I made a note to suggest a more organized system. I clicked on the movie "Vacation" and entered its main directory.

A slew of titles sprang up. I didn't recognize the names. I clicked on a file called "vacay 16 01." The movie unfolded, showcasing a hotel bed with Jennifer lying naked. The pillows provided support for her upper body. Her face expressed elation as she palpated her genital area. "I wish this were your thick cock massaging my wet cunt. Please don't get up after soaking my pussy. I'll inform you when I'm ready for you. Just stay there and take pleasure in your erect dick," she uttered into the camera. She cupped her breasts and played with her pussy. She had no pubic hair. She effortlessly caressed her lips, moving from rubbing her clit to stroking her labia. One hand squeezed her breasts while the other rubbed her pussy. Her gaze fixated on the camera.

I was fascinated. I was anxious to watch this intimate video. But, I had never seen a genuine woman play with herself before. Once, a friend and I shared sexual acts, yet we merely stroked our clits until we climaxed. This was a woman I had just met. It was a deeper invasion of her privacy. I felt overwhelmed by it. My arousal was escalating by the minute. I watched her bring herself to orgasm. My body quivered, witnessing it. Then, slowly, she settled back and became still. She raised her fingers to her mouth and sucked them. Then she called out, "Bring that massive cock here and fuck me right now."

Out of nowhere, Victor appeared in the camera's view. He repositioned her on the bed and slid his solid dick into her. She moaned and yelled as he fucked her.

Suddenly, Kara was standing at the door. "Uh...are you okay, Jennifer? Your loud moaning and screaming are a bit concerning."

"Oh, my god! I'm so sorry, Kara," she said, blushing. "Victor and I are just...watching a movie. I guess I got a little too loud."

"Oh," Kara laughed, "I'm going to head out. Have a good time!" she said as she left.

Catching a glimpse of his nudity left me aroused. I quickly slipped out of my running shorts, spreading my legs wide. I Friedman my fingers along my pussy while watching the erotic display playing out before me. The vision of Victor fucking Jennifer on the screen filled my mind, causing me to imagine him inside me. His thrusts around her sent Jennifer into ecstasy as she encouragingly moaned, "Push it deeper, Victor. Fuck my pussy hard, baby." I emulated her words, pinching my lips and running my fingertips along the exterior. I widened my pussy, feeling my wetness soak through my fingers. I alternated between rubbing my clit and stroking my inner lips, creating a tantalizing sync between the two actions. A desire swelled up within me.

I inserted two fingers into my vagina, matching Jennifer's own actions. The sensation felt incredible while my pussy adjusted and opened up to accept them. I bit my lip momentarily, holding back a moan. "'Fuck my pussy,' I exclaimed, feeling the still-intensifying pleasure coursing through me. 'Yes, Victor, fuck me harder!" I screamed as waves of ecstasy emanated from my depths. I was leaning back, rubbing my clit with one hand and shoving my fingers inside myself with the other. Each motion sent a surge of satisfaction coursing through my body. I orgasmed with more intensity than ever before, yelling out Victor's name as my body shook and released deeply enough to saturate my fingers. My body grew limp and collapsed back into my seat, watching Victor continue his penetration.

Jennifer's body arched as she experienced yet another orgasm. Her breasts shook as he began to approach his own climax, "Fuck me deeper! Harder!" she yelled. His entire ass became exposed while his hips rocked, thrusting deep into Jennifer. After a brief moment of lying on top of her, they shared a passionate kiss. Still, words seemed distant past their passionate embraces. Eventually, he peeled off, and Jennifer asked that he stand in front of the camera for her to savor his post-coital splendor. Victor's dick was proud and shiny before he obliged Jennifer's request by turning toward the camera. "Oh my god, the taste of mixed orgasms drives me wild," she shared.

"Just watching these videos will far out way any pool boy," I murmured.

"Let's capture some content where you're skillfully unemployed," Jennifer proposed. "In the next video, you'll film yourself masturbating for me," she suggested.

"Yes, your Highness."

"Mmm, comes to lick it off properly. I don't want any of it to go to waste," she requested.

Victor strutted over to face Jennifer. Her lips flicked his member, tasting every drop left by their previous episode. He expressed his appreciation. "Your cum tastes heavenly, dear Jennifer. Lucky me to have a wife as passionate and driven as you," he praised her.

"You're the best. This pool boy isn't comparable to my most treasured servant," she boasted while visibly proud and content.

"It did cross my mind. Perhaps we should train a pool boy for when you're in need of an assistant,"

"I have you at home. That pool boy would just be a distraction," Jennifer reasoned, satisfied with the status quo.

The video played, and Victor turned off the camera before disappearing from the scene. My eyes glued to the screen, desperately hoping to catch a glance at his member. It was one of the most fascinating highlights. I shook my head, momentarily lost and tongue-tied. The image flickered to the previously viewed scene from "Vacay 16 02." A hardening Victor lay in bed as his hand gripped his member. "Get yourself hard, she urged from the camera. His chest and abs shined, showcasing his toned and masculine appearance. He smiled, an aura of self-confidence enveloping him. I couldn't absorb the lustful sight enough. With my index finger and thumb, I pinched my lips. Considered yet another starring role in this amateur pornography, he gently stroked his thick look at my hand digitally, feeling his accumulated hardness. I could not peel my eyes from his glistening, growing member. What a image.

I just couldn't contain myself. My digits delved into my vagina without a second thought. I had never engaged in self-pleasure twice in a row before, but that man stroking his dick sent me over the edge. My fingers circles around my folds as his hand went up and down. I rubbed myself, and squeezed my heaving breasts. His dick started to become engorged. A glossy sheen covered it. The head of my love button was incredibly sensitive. I had to carry on. He was thrusting his member. Jennifer egged him on, "Yes, long strokes. Go all the way up and down. Set the other hand in there and run it along your balls. Rub more oil onto yourself."

He gripped the bottle. Oil drizzled onto his shaft. He manipulated it onto himself with his hands. "That feels great," he said. The camera zoomed in and just showed his abs, his body, and his cock. He started thrusting his hand faster. "I'm about to climax." He said.

"I've changed my mind," I said. "I want to watch you ejaculate in the air."

"Yes, my love," he agreed.

My hand massaged my vagina faster. Two digits slid deep into my pussy this time. I watched his hand move up and down, my fingers in and out, trying to mimic his speed. I salivated onto my hand and stimulated my little button. His hand sped up. His groans echoed. "Yes, fuck my pussy, Victor. Faster," I urged. He picked up the pace, rubbing his balls. "Oh, fuck yes, Victor. Oh, I am so very wet for you."

I pushed my hand faster, rubbing my clitoris, feeling my body strain. I held my breath. I watched his cock blasting off. My love button was throbbing. I screamed, losing control and convulsing. I felt my body tense up. "Oh my god, oh my god, oh my god, yes, yes, yes, yes, Victor."

My body shook from the strongest orgasm I've experienced in my life. My nerve endings tingled. I could barely maintain my focus on his blankly staring cock spurting out stream after stream of cum. His male equipment quivered, almost in slow motion, as my ecstasy rode an unyielding ridge and I relaxed. I took a deep breath. I released my hand from my soaked pussy and observed the mess on the leather chair. My shirt was pushed off my breasts, leaving me naked, sprawled on the chair. I watched Jennifer lick his cum from her fingers off-screen.

"God, you look so sexy licking those fingers mixed with our juices," he told Jennifer.

"You're right. Your cum tastes phenomenal," Jennifer stated.

I brought my fingers to my lips and licked them. It was the first time I'd ever tasted my womanly juice. The sexiness hit me hard. I imagined Victor watching my every move and mimicked Jennifer's every motion.

Just as I sat up, a cry was heard on one of the speakers. My entire body stiffened; a baby. I sprung into action and rushed upstairs to the room where the children were located. After trying to soothe the baby, it thankfully started to calm again. I headed back down to the media room, picturing someone holding a cock while breathing heavily. The screen displayed Victor's erection and Jennifer licking his semen from her fingers. I paused it, deciding to clean up. I cleaned the chair and returned everything to its former state. I concluded by closing the folders, opening my laptop, and booting up the computer.

I resumed my seat in the audacious living room, a television playing a meaningless show. Feeling inspired, I opened my laptop and found the movie folder. I found a separate picture folder also and even more frequented. There were myriads of pictures of Jennifer and Victor in seductive poses, adorned in costumes and completely nude. I chose them all. I copied them to a handy device. I did the same with the movies. I had discovered a wild treasure trove for my erotic pleasures.

Victor and Jennifer were returning home past midnight, him intoxicated. He reached the top step, panting. Jennifer declared that he had so many drinks with his coworkers that he went overboard tonight. She assured me that she would credit me with the money. She turned to me and asked if I could help her up.

As her dress hit the ground, her breasts displayed in skin-hued cups. She removed the cups from her breasts. "Oh wow," I said.

"Victor never realized what he was missing out on. No panties and wetter than a tropical winter, he's passed out," she chuckled.

"No, he hasn't. I'm sure he'll be agitated. I thought you were wearing a G-string earlier?" I cast my gaze over her body. I felt a tingling sensation as I imagined the movie playing in my head.

"He saw me in that. I had to shake things up. Keep them guessing. I should get a camera, my vibe from my bedside table, and record a video for him," she chuckled. "Or maybe have you record a video of me. That would definitely tease him by missing out."

I laughed nervously, "That would teach him."

"Goodnight, darling, thanks. Did you leave a note for Victor detailing what you did last night?" She seemed nonchalant about standing completely naked and talking to me.

"What did I do?" I asked nervously, my mind flashing to fingers frantically working on myself while my eyes tried to avoid her breasts and exposed vagina.

"The computer work so he could pay you?"

"Yes, yes, I did. I'll call tomorrow and inform him."

"Kara, thank you. She inspected me from head to toe. "You have a nice body, Kara. You should show it off more. We should go shopping and buy you some sexy outfits."

"That would be fun."

"Thanks for offering to stay over. I may take you up on that in the future. Victor travels often. When he does, I might have you over for a girls' night to keep me company. Since the move, I haven't had a chance to make many friends here."

My mind wondered whether she was looking for a pool girl to play with when he's gone. I smiled, "Sure, that sounds good."

"Goodnight; thank you for babysitting the kids."

"No problem, goodnight." I approached the door.

I ran home. As soon as I entered my room, I opened my laptop. I skimmed through the films. There were hundreds of them. A few hundred images. I caressed myself again that night, watching them fuck in their room. I witnessed Jennifer grab her vibrator from her nightstand and use it on herself. It was incredible.

The next day, Victor called me. He apologized for being drunk and not saying goodbye properly. I informed him that it was okay.

"I reviewed the security report and saw what you did the previous night."

My mind froze, "What do you mean by that?" How vague was he?

"The notes you left me regarding the security review of my system. The adjustments you made."

"Oh, that, indeed. I'm pleased you found it."

"You seem to have fully worked it out. Got everything figured out and executed it flawlessly."

Fuck, I did?? I thought, "Yes, it took me about two hours, maybe a tad more. I have a few more details and options that we can discuss specifically, though."

"That's great. We'll evaluate them before the wife and I go out on Tuesday. Can you come sit?"

"Tuesday, sure, no problem."

"See you then. By the way, I sent you $500 from my account via Venmo."

"Thanks," I hung up the phone. I checked my account. He paid me $500 just to set up his system. Fuck, no need for waitressing. Plus, the money Jennifer sent me. That was an incredible side gig.

Over the subsequent weeks, I watched nearly all the movies. I uploaded the files to my laptop. Each time I visited their house and saw Victor, my pussy tingled. Or Jennifer would be wearing something provocative, and I'd picture her naked. I'd look for clothes that had his scent and hug them.

Every encounter, I would watch a new movie on my laptop. I discovered the media room was soundproof. I screamed my head off, rubbing my pussy, begging for him to fuck me in there. I'd lie in the living room in the oversized chair, quietly stimulating my pussy. I found Jennifer's toy in the bedside table and used it a few times. I stretched out on the ottoman once. I sat in his office chair, swathed in a sweatshirt. I orgasmed more often than I ever had before. I loosened my pussy so much it was starting to burn. But the urge was always present when I was around either of them. I could've easily got them to babysit. It was like that house was a potent aphrodisiac.

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