The Babysitter Beta 03

On a typical day, I finished work around four o’clock, took a few minutes to browse socials, made dinner, and traded off with Penny to take care of Abby. Penny left for her parent’s house, and Abby and I would go about our evening routine. It was pretty typical. We’d spend some time together doing whatever, and she’d tell me about her day with Penny in the roundabout way only a rambling three-year-old could. Then it was clean-up, bath, reading, and bedtime. 

Wrangling a three-year-old through that routine could be a chaotic run through hell some nights and less demanding on others. It was never easy, but Abby was a good kid. Unfortunately, even good kids resented bedtime. 

Tonight, Penny hung back to help. She had dinner with us, which hadn’t happened before. Abby loved it, and while she demanded I pay attention to her instead of Penny by interrupting whenever I tried to talk to her babysitter, she also demanded Penny’s attention. Clean-up time was much easier with an extra pair of hands, and Abby wanted Penny for bath time, so I let them do their thing while I did the dishes. 

Reading time, however, was my territory. Penny didn’t perform the voices correctly, according to her audience, and Abby held strong opinions about the characterizations given to her Bedtime stories. Penny stood leaning on the door, watching as I sat in my chair beside Abby’s crib, reading the third story of the night. 

Despite her excitement at Penny's presence, sleep eventually took Abby into its habitual embrace. I closed the fourth book and set it down, silently rising from my chair and gesturing for Abby to move into the hallway. I followed her out and shut the door behind me, the monitor in my hand. 

We didn’t speak until we made it to the living room, and both of us gave a tentative pause to exhale in relief that Abby was down for the night. For a moment, I almost felt like I had a co-parent, and the pleasure of Penny’s presence was swiftly followed by guilt. Charlie would be here if she could, but my late wife passed years ago, and it’d been rough without her. 

Penny’s hand on my arm told me she could read my thoughts as they played across my face, and I gave her a soft smile. 

“Sit.” Penny said, pushing me toward the sofa. 

I sat, sitting in my customary corner spot on the sofa. Penny took the monitor from me and put it on the end table beside me. Then she left. I turned my head and followed her as she disappeared into the hallway. Then I turned my attention to the TV and picked up the remote. I turned the TV on, keeping the volume low, and opened Netflix to continue the next episode of whatever I’d been watching. 

Penny set a glass of water on the end table beside me and curled beside me. 

I froze as she leaned against me, but she was soft, comfortable, and warm. Slowly, I relaxed and put my arm on the back of the sofa. Penny reached up and pulled my arm around her, leaving my forearm across her stomach with her shoulder against my ribs and her head against my chest. 

It felt strange but comfortable. This was the first time I’d been like this with someone since Charlie passed. The intimacy was so casual it felt euphoric and alien at the same time. I couldn’t process it, and my mind wanted to tear itself apart at the contradictions. 

“Relax.” Penny said, patting my thigh. “Don’t think about it too much. Just relax, and let me help you feel better.” 

I scoffed. “I thought the whole point of you staying late tonight was so that I could make you feel better. You know, make up for… for what you did for me earlier?” 

“The blowjob?” Penny asked, smiling at my reluctance to be crude. The memory of her on her knees beneath my desk, while I had a meeting with Svetlana, was only a few hours old. The newest addition to my spank bank was still fresh, and she smelled even better now in her freshly laundered clothes. The short shorts and cropped T-shirt were good summer clothes, but Penny made them look scandalous with her figure. 

“That was for both of us.” She said. “I wanted to suck your cock, so I did.” She shrugged, nudging my ribs a bit. “But I’m not opposed to you rewarding me for it. I’m horny as fuck right now.” 

I twitched in surprise. “You are?” I knew she thought I was sexy, but I didn’t think the shorts and t-shirt I’d changed into were that sexy. They were comfortable, though.  

“Oh, yeah.” Penny turned to look up at me from her place on my chest, her hand on my stomach. “Watching you be a good dad? The way you are with Abby? I can’t explain it. It warms my heart. Maybe it’s something biological. I’m attracted to guys that would make good dads, and you’re fucking hot, Mister Castillo. I want to climb you like a tree right now.” 

I blushed, shaking my head as though she was pulling my chain, but her unblinking gaze didn’t let me get away with brushing her off. 

“So what’s the plan tonight?” Penny asked. “Netflix and chill?” She gestured to the TV screen. “Fucking on the sofa? Moving this to the guest room? Your room?” 

The idea of taking her upstairs to my bedroom was… terrible. I thought the image would be hot, but the opposite happened, and my brain started sending alarm bells left and right. That wasn’t Penny’s space. That was Charlie’s space. Even though it wasn’t anymore. 

I sighed. 

“Not your room.” Penny said, smiling softly. “That’s okay.” She slid her hand to my thigh and didn’t say anything more. “Let’s just chill here and play it by ear. Okay?” 

I nodded. 

Penny passed me the remote, and I flipped through the suggestions Netflix made. 

“Oh, Baywatch.” Penny said, pointing to the screen where the 2017 film was nestled in the Top Ten in the US. 

It made sense. It was June, and hot actors and actresses bouncing across the screen made for high ratings. Though, from what I remembered of the TV series, I didn’t have high expectations for a good movie. If the idea was just to chill and have some mindless fun, though, it might be perfect. 

“I heard it’s supposed to be good.” Penny said. 

I shrugged but obliged her. I turned on the movie and settled into the couch with a deep breath that made her head rise and fall. 

“Do you have a blanket?” Penny asked. 

I pointed to the armchair with a folded fleece over the back. Penny pushed off me and retrieved it, throwing it over her shoulders like a cape as she returned. I smiled, and she giggled. 

“I’m super-Penny!” Penny said, laughing. “Nearby air conditioning vents are my only weakness.” 

I chuckled slightly, and she returned to the sofa, kicking off her shoes and curling her legs under the blanket. She put my arm back around her and pulled the blanket over both her and it. Then she squirmed a bit, making me shift so I was more reclined. I reached over and pulled the switch, activating the footrest. 

“This a recliner couch?” Penny asked, surprised.

“Yeah. There are buttons on each side.” I said, pointing to the other end. She didn’t move for it but smiled. 

“I learn something new every day.” She said, settling in against my chest again. 

We watched the movie for about fifteen minutes before she became restless, shifting around beneath the blanket. 

“You okay?” I asked. 

“Yeah, just a little warm.” Penny said. “You’re practically a furnace.” 

I laughed. “Well, the fleece traps all the heat. You can toss it on the floor, if you want.” 

“No, the fleece stays. Hold on, I know how I can cool off.” Penny said, and she wiggled for a moment, moving her arms in a motion that looked suspiciously like taking off her shorts, which was precisely what she’d done. She tossed them across the room. They landed on the armchair. “Much better.” 

I raised my eyebrows, but the thought of her sitting beside me with nothing but her thong and ankle socks below her waist made me stiffen. I had seen her naked before and in her lingerie, so my imagination could fill in the blanks without overtaxing itself. 

She settled against me again, her hand resting casually on my thigh, which did not help the tightening in my shorts. 

Another fifteen minutes passed, and she sat up again. I glanced over and saw her peel off the blanket, revealing her body in profile. Her large bust beneath her cropped T-shirt, her bared flat stomach, her curvy hip, and her bare thigh were marred only by a thin floss-like strap of her thong pulled high over her hip. 

Before I could ask what she was doing, she whisked her shirt off, tossing it to join her shorts. She turned her back toward me, sitting straight. “Give me a hand with this?” She asked. 

I stared at her back, dumbstruck for a moment, but eventually, my slowly churning brain caught up to what she was asking me. I clumsily tugged at her bra’s hooks and managed to get one of the three unhooked. 

“You have to really pull it.” Penny said, laughing at me. “The downside of huge jugs? Industrial strength locks on the bra.” 

I laughed, using both hands to push the bra together and remove the pressure pulling the sides of the latches. Unhooking it was easy after that, and she let the bra fall to the floor without a second thought. Pulling the blanket after her, she reclined on me again, her breast against my side and my forearm pressing against the underside of her breasts as she held my hand beneath the blanket. 

Her skin was electric and warm, even warmer than before, and somehow, knowing that her large eraser-tipped nipples were bared beneath the blanket made my hand’s proximity to them more sensual. 

“Is this okay?” Penny asked, and the nervousness in her voice made me consider her question. 

“Yeah.” I said, relaxing. “This is… nice.” 

Penny smiled. “If you think this is nice, you should see what I’m going to do to you when the movie is over.” 

I gulped, and she laughed. 

“Don’t worry, you’ll like it.” She winked and nestled into me again, watching the film as it played out on the screen. 

The movie was funnier than I expected, and playing it as a comedy was the right choice. It was much better than anticipated, even with all the distractions. 

Another few minutes passed, and Penny moved my hand, placing my palm on her nipple. She squeezed my fingers closed, groping herself with my fingers. I took the hint and groped her, moving between breasts every few minutes. She squeezed my thigh but didn’t make a move to take me out of my shorts. 

After some pleasant groping and touching, she moved my hand again, holding my pinky in one hand and my thumb in the other. She lifted my fingers to her mouth and sucked my middle finger. Her hot, wet tongue swirled around, and she closed her lips around the base of my finger. She sucked and moved my finger back and forth. She slobbered over it, soaking my finger and some of my hand in her saliva as though it were my dick. 

It might as well have been, given the effects she had on my dick. I tented my shorts almost as soon as she started. I closed my eyes and breathed heavily as she moved on to my index finger, then my ring finger, and back to my middle finger. 

When she’d thoroughly slobbered on my hand, she moved it beneath the blanket again. She split her legs open, one knee pointing at the TV, the other at the ceiling. She dragged my fingers across her skin, trailing her saliva between her breasts, across her stomach, to the hot, damp patch between her legs. 

“Are you going to make me beg, Julio?” Penny asked. “Or are you going to use those fingers of yours to fuck me?” 

She pulled her thong aside and pressed my middle finger against her pussy lips. She was soft, hot, and much wetter than I expected as I tentatively curled my finger across her slit. 

“Mmm.” Penny hummed. “That’s it. God, your fingers feel so good down there.” 

I smiled, encouraged by this news. Penny was the first woman I’d been with since Charlie, but she was entirely different. She enjoyed and preferred things Charlie would have hated, and it was hard not to think about my late wife and her preferences as I played with Penny’s body. That wasn’t fair to Penny, though. She deserved my full attention, and I was determined to give it to her. 

I moved my other hand, reaching under her head to grope her breast beneath the blanket while I fingered her. 

Penny moaned, leaning her head against my ribs. She rolled her hips, lifting them toward my hand. My palm pressed against her clit as I held my hand steady, and her eyes shuddered shut. “Mmm.” 

I circled the top of my palm against her clit, moving it in low-pressure circles as my fingers explored her folds, stroking and getting a sense of the lay of the land between her legs. My tactile senses were enough to give me a rough map of her pussy beneath the blanket, and I smiled but needed relief from the pressure building in my shorts. 

I unzipped my fly and undid the button, sliding them down so that I was able to pop free of the elastic band of my underwear. 

“Oh, Mister Castillo.” Penny gasped. “Are you turned on right now?” 

It was a rhetorical question. My erection was in plain view from where her cheek rested against my ribs. 

“Do you like playing with my pussy that much?” She asked. 

My dick twitched in response to the lewd question, and I hoped that was answer enough. I knew I shouldn’t, but God help me, I enjoyed playing with more than her pussy. Her entire body was a delight, between her large breasts, her pointed nipples, her curvy hips, her spankable ass, and especially her hot, wet pussy. I didn’t know if I could tell her that, though. To think it? Fine. To admit it aloud felt like a transgression. She was my daughter’s babysitter. My employee, of sorts. I was taking advantage. 

Sure, she was the one in charge, leading me through this time together, but I was thirty-nine, and she was nineteen. This was wrong, but when the scent of her arousal filled my nostrils at my inhale, I no longer cared. I hooked my middle finger into her pussy, and she grabbed my wrist, holding it in place and pulling my hand firmly against her clit. 

“I love when you play with my pussy.” Penny moaned. “And I love your cock.” 

I almost scoffed, but I was distracted by the way she rolled her hips against my hand. I stroked my finger in her pussy, plunging in and out of her as she met my finger thrusts with a high-pitched “Ah!” that gripped my cock with an invisible hand. 

“Can I…” Penny gasped. “Can I suck it, Mister Castillo?” 

I groaned. On the one hand, I hated when Penny called me Mister Castillo when we played like this. On the other hand, hearing that formal title and name in her panting, gasping, sexy-time voice was pure cocaine. The instinct to push her head onto my cock surged in me, but I settled for groping her breast, then releasing it so she could slide down my torso. 

“Suck it.” I said, my voice far huskier than I’d intended. 

The gravel in my voice seemed to have the same effect on Penny as her voice had on me. She dropped her face to my cock as though I’d shoved her onto it. She took me into her mouth and sucked, slurping in loud noises that nearly drowned out the movie. 

“Fuck.” I gasped and matched her enthusiasm with my hand between her legs. 

“Mmm!” Penny exclaimed with her lips halfway down-my cock. As we were, she could still watch the movie, her head on my abs as she sucked my cock. I tilted my hips to make it more comfortable for both of us, and she hooked her leg over the back of the couch. I pressed my pinky and index fingers around her pussy, making an almost Spider-Man motion with my middle and ring finger pumping in and out of her. 

She had one hand on my thigh, the other groped her breasts, pulling her tits as if trying to milk them, squeezing her nipples between her thumb and index finger each time. 

I watched her, the blanket falling away as we moved, shuffled, and fucked without fucking. Her naked body was a delight as it came into view, and the sight of her naked breasts made my dick swell in her mouth. She wasn’t quiet about her enjoyment of my cock. She slurped and schlorped, making wet, moaning noises as she worked my shaft like she was trying to milk it with her face. 

“Oh, Penny.” I moaned, pushing my head into the sofa cushion behind me. “Fuck…” 

Penny moaned to match me, and she rolled her hips until she suddenly started moving. Alarmed, I froze, but she pulled off and kicked away her thong, scrambled, and shifted onto me without giving me a chance to move. 

“I’m so close.” Was all she said by way of explanation as she climbed onto me, straddling me and rubbing her pussy lips against my dick. “I need you, Julio. I need you inside me.” 

I grunted, groaning as my dick parted her lower lips. 

“Fuck me, Julio. Please?” 

She didn’t need to tell or ask me twice. I reached between us, angling my cock, and when I felt the tip press into her, I slammed home, driving her up and shoving her breasts against my chest as she gave a cry of “Ah!” and hugged me close. 

I took over, my hands wrapping over her hips to her backside, pumping her onto my cock as I pumped into her. She clung to me, her breath on my neck, her eyes barely open and rolling into the back of her head. 

“Ah! Ah! Ah!” Was all she could say, and I grinned at the moment of prowess that surged through me as I rocked her world. 

“I’m–” She tried to say. “I’m–!” 

I felt her orgasm as she clamped around my dick with such sudden force I had to stop pumping because I couldn’t pull out of her. Despite how wet and slick she was, despite how many juices spilled out of her and onto me, she’d trapped me inside her, and I rode out her spasming, clutching orgasm as long as I could before I felt the surge in me empty into her. 

“Penny!” I cried, and she echoed me with a sharp “Ah!” As I filled her body with her inevitable reward. 

My entire body seized with hers, and we clung to each other fiercely, our arms and hands clutching and grasping hard and rigid around the soft flesh between us. Her delightfully large breasts and soft curves pressed into me as she went limp, and I relaxed, unclenching as she released my cock from her inescapable vice grip. 

I panted, realizing my hair was sweaty against the sofa cushion, but I didn’t care. My entire body relaxed, and Penny settled on top of me, relaxing as our bodies melded together. I pushed the recliner back the rest of the way, and she laid on top of me, my dick sliding out of her but remaining between her thighs as she straightened them between my spread legs. 

“Mmm.” Penny nestled her nose into my neck, which should have tickled but somehow felt nice. “Thank you.” She kissed my cheek. “I needed that.” 

I rubbed her back and took a moment to catch my breath. 

When I woke it was to a loud buzzing noise coming from somewhere past my feet. I didn’t know what it could be, but the weight on top of me didn’t let me move. I blinked my eyes open to realize the movie had ended, and by the look of the room around us, it ended a while ago. There was still fading sunlight in the sky when Penny and I had fooled around, but even with the curtains closed, I could tell it was truly dark outside now. 

I shifted, and Penny grumbled before her eyes snapped open, and she practically leaped off me. 

“What time is it?” She asked, turning this way and that. 

I was too distracted by the busty, nineteen-year-old woman in only ankle socks bouncing and turning to hear anything she said. My brain was too busy directing all processing power to visual stimulation. 

The buzzing noise was Penny’s phone on the coffee table. The screen lit up with a picture of her and her mother at a restaurant I didn’t recognize. 

“Shit!” Penny said, grabbing her phone. “Hey, Mom.” 

I sat up immediately at that and started helping Penny find her clothes after I refastened my shorts. She started putting them on, hopping around while carrying on a somewhat sleepy, mostly panicked, conversation with her mother. 

“No, sorry! I fell asleep on the sofa. I didn’t mean to stay this late.” 

The straps of her thong snapped against her as she released the elastic over her hips with too much pluck. She didn’t seem to mind the snap, or at least she paid no attention to it.

“Yeah, my plan was to stay late to help with bedtime so I could learn the ropes for Friday when he has that work thing.”  

I handed her the shorts she’d tossed, and she put them on. 

“No, he went to bed, but he said I could watch the new Baywatch movie since he had it on Netflix.” 

She put the bra on quicker than I’d removed it. 

“Yeah, I’m sorry. I didn’t mean to fall asleep. The movie was just really boring.” 

She pulled her crop top on. 

“Oh.”

She froze. “Are you sure?” She asked, pausing to look at me. I looked confused, not sure what she was asking with her silent expression. Whatever answer she was looking for on my face, she didn’t find it. 

“No, that’s okay.” She said, shaking her head. “I’ll be home in a few minutes. I just need to clean up and lock up.” 

I shook my head, letting her know that I would handle it. 

“Oh. Uh…” Penny paused as if trying to figure out how to tell her mother something, and I wondered what it was. “Okay.” She said. “I’ll see you in a few.” She ended the call. 

“Are you okay?” I asked. 

Penny nodded. “Yeah, yeah, I’m fine.” She said, grabbing her purse. “I’m sorry, but my mom waited up for me. I’ll… I’ll spend the night another time.” 

I looked surprised. Of course, Penny was welcome to spend the night if she wanted to, but I didn’t understand why she was apologizing for not doing so. My surprise, however, seemed to register as something else as her sheepish, apologetic smile fell into a genuine frown. 

“You don’t want me to spend the night?” She asked. 

“I… I don’t know. I don’t not want you to spend the night.” I said. “You’re welcome to crash here any time you want to, you know that.” 

“Right.” Penny said, still frowning. “I’m… I’m sorry. I just… I wasn’t planning to, and then we fell asleep, and I thought maybe I would, but then… I’ll just go home.” She said, looking around to make sure she had everything. 

“Penny.” I said, stepping toward her. 

She stopped, looking at me like I was offering her a lifeline. 

“I’m sorry. I didn’t mean to suggest that I don’t want you to spend the night here with me. I just… I was surprised. I didn’t think you’d want to. And I don’t want to pressure you to, either. I know we’re keeping this a secret and handling it as it comes, but… this is all new to me. I’m following your lead.” 

Penny laughed, sweeping her hair behind her ear in a motion that I couldn’t help but smile at. She made the move from the movies seem so natural. 

“I’m new to this too, Mister Castillo.” She said. “Julio. How many older guys do you think I throw myself at, exactly?” 

“That’s not…” I stopped, not wanting to dig my grave any deeper. “I didn’t mean it like that. I just mean… I don’t know what I did to start this, and I know we shouldn’t be doing it, but–” 

“We’ve been over that.” Penny said, getting defensive. 

“But!” I said, reiterating my conjunction. “But I don’t want to stop, either.” 

Penny’s defensive expression softened. The corner of her mouth ticked upward in a smile. “Well, good. Because after that? I don’t want to stop either.” She giggled, slight and girlish as she twisted her foot on the carpet. “You fucked me into a coma, Julio. I don’t think I would have woken up until morning if you hadn’t started moving.” 

I scoffed. “Yeah, well. You weren’t so bad yourself.” 

Penny smiled and shuffled forward. I could tell she was nervous, and if her heartbeat was anything like mine, we were both about to speed into dangerous cardiovascular territory. I stepped forward to meet her halfway, and she held onto my arms as we kissed. 

“Goodnight, Mister Castillo.” Penny said, pulling away. “Sweet dreams. I’ll see you in the morning.” 

“Sweet dreams.” I echoed and followed her to the door. I closed and locked it behind her, but not before she gave me one final look back at the end of the walk, and we waved goodbye. 

I sighed as I cleaned the dishes and took the monitor to my bedroom. Abby was still asleep. Now that she was out of the night-time feeding phases, she’d settled into deep nightly sleep, which I thanked God and all the saints for every single day. She was usually good for twelve hours, often on the dot, and I knew that in that respect, at least, I was the envy of many other parents. 

Imagine if they knew about Penny? 

I chuckled at the thought, tossed off my clothes, and climbed into bed. 

I sighed. “What the fuck am I going to do about this?” I asked my ceiling. 

It returned my inquiry with a flat expression.