The Babysitter Beta 02

((Behold, the extra nobody asked for! I realize this isn’t Harem House or Luther’s Pride, but I had the idea for a sexy little scene and I wrote it out for the fun of it and to get it out of my head. I hope you enjoy it!))

A few days after our poolside rendezvous, Penny hadn’t said anything about what we’d done. The most she’d done was wink at me occasionally when we were alone. With me working from home and her taking care of my daughter, there wasn’t a lot of alone time, but it happened a few times a day for several days. 

On the fourth day, a Thursday, I was eating a late lunch in the kitchen when Penny walked in. She wore a cropped t-shirt, a cloth over her shoulder, and a pair of khaki shorts that stretched over her round ass. 

She stared at me as she entered and smiled a toothy-white grin. She opened the cabinet, showing me her shorts dipped in the back, a notch forced by the gap of her waistband. They showed off the start of her cleft and the two dimples on her lower back. Her cropped t-shirt bared most of her stomach from her low waistband to an inch beneath her breasts. Less when she reached for a plate.

“Enjoying your lunch, Mister Castillo?” Penny asked. She turned to face me. 

“Yes.” I said, glancing nervously behind her. 

“Abby’s down for her nap, but she… puked all over me.” She said. She gestured to her shoulder covered by the stained cloth. “Do you mind if I use your laundry machine?” 

“Go right ahead.” I said, gesturing to the kitchen door. The laundry closet was down the hall. “I just did laundry yesterday, so the machines are free.” 

“Perfect.” Penny said, smiling. “Then can I eat lunch with you? I fed Abby but haven’t had a chance to grab anything myself.” 

“That’s fine.” I said, nodding. To my shame, I watched her walk away. The khaki hiking shorts hugged the curves of her ass and stretched with the sway she put into her hips when she spotted me watching. I blushed and returned my attention to my food. The chicken salad was a much safer dish to look at. 

“So, what are your plans for this afternoon?” Penny asked when she re-entered the kitchen a few minutes later. The dull whirr of the washing machine droned from the hallway. “Going to lounge by the pool and soak up some sun while you work?” 

I looked up and sucked in a breath. Penny had removed her shirt to wash it, which I expected, but she hadn’t replaced the clothing. Instead, she wore her bra brazenly as if it were a top. Three-quarter cups of black mesh held back pounds of rounded flesh and barely obscured her two large nipples poking through the material. She also removed the shorts to show the matching mesh panties showing off her hairless pubic region and her wide, round ass now hanging out of her panties. 

“Are you okay, Mister Castillo? You said I could wash my clothes, right?” Penny asked. The smile on her face proved she knew exactly why my fork had stopped halfway to my mouth and why my eyes might fly out of my head like a cartoon wolf. 

“Yeah… don’t you have any spare clothes you can wear?” I asked. 

“Do you not like my outfit?” She asked as she twisted to show it off. “I figured it’s not that different from a bikini, and you’ve seen me in less.” 

My lap threatened to take over my brain. “That’s lingerie.” I said. 

“I know.” Penny said. She stopped at the fridge, opened the door, and bent over. Her panties seemed to disappear into the cleft of her cheeks. When she stood, several intense seconds later, she carried her lunch tupperware in her hands and walked to the table. She took a seat across from me. 

“You can borrow one of my T-shirts if you want.” I offered. 

“Can I wear one of your button-downs?” Penny asked. “I like that look. A long oversized button-down shirt, and nothing else. Guys go crazy for that, right?” 

I swallowed. 

“Penny…” I started, but she held her hand up to stop me. 

“Don’t make an excuse and run out of the room this time. You’ve been avoiding me all week.” Penny said. 

“What we did–” I started. 

“Was a blast.” Penny finished my sentence in a way I didn’t intend. 

“It can’t happen again.” I said. It was what I was supposed to say, and I was determined to say it, even if the determination in my voice had all the strength of a particularly feeble mouse. 

“Did you get married this week?” Penny asked. 

The non sequitur startled me, and I looked up at her face for the first time since she’d sat down. She smiled and winked at me. 

“I told you, we’re two consenting adults having fun together. That’s all. There’s nothing wrong with that.” Penny said. 

“You’re nineteen.” I said. 

“Which is old enough to fuck, and young enough to rock your world.” Penny said, smiling. 

“And I’m thirty-nine.” I said, gesturing to myself. 

“Which is young enough to fuck, and old enough to rock my world.” Penny said, biting her lip after she said it and lowering her eyes as if she could see my hard-as-stone dick through the table and my slacks. “Come on, Julio. You want to bend me over the table or the counter?” She asked, gesturing to each. “Or should I get on my knees and crawl under the table while you finish your lunch so I can use your cum for salad dressing?” 

My eyes flared of their own accord, and I swallowed thickly without anything in my mouth, gulping at her imagination. 

“You’re on the clock.” I said, finally. “And I have to get back to work.” 

“We’re on our lunch break.” Penny said. “If Abby cries, I’ll take care of it. If you get a work call, answer it.” She gestured to my work cell on the table beside me. 

I shook my head. 

“Well, then update your Tinder profile.” Penny said, almost accusatory, as she opened her lunch. “You could make a girl think you’re saving yourself for her if you refuse to use the photos she took of you for their purpose.” 

I frowned, feeling slightly more comfortable with this topic but not wanting to admit she was right to be annoyed. She’d put a lot of effort into taking those pictures, and I hadn’t updated my profile with them like she told me to. Penny speared her tuna salad with her fork but kept her eyes on me as I ate my chicken salad.

“You’re ready.” Penny said. “You should put yourself out there, and you need to get laid. You’re too wound up and anxious.” 

“I know, I just… things are complicated enough with Abby, right? I’m a single dad, working full time. I’ve got a toddler and my baggage as a widower on top of that. Then there’s…” I hesitated, looking up into Penny’s brown eyes flecked with green as she stared back at me. 

“I’m not a complication.” Penny said. “I won’t get in your way.” 

“Okay.” I said, frowning. 

“You need to get laid, Julio.” Penny said. “Seriously. I hate seeing you so unhappy. You’re a great guy, and you deserve a girlfriend you love.” 

I sighed, unsure how to disagree with her but feeling like I should. 

“And it can’t be me.” Penny said, saying what we were both thinking. “I don’t mind fucking you, giving you some release, and using you for mine, but my parents would freak if they thought we were a serious long-term item.” 

An understatement. I’d seen her father’s gun collection. His jokes about cleaning them when Penny brought boys over had proven completely serious. He and I laughed about it together, but here was Penny, sitting at my kitchen table in nothing but lingerie, talking about using my dick for her pleasure, and my dick wanted her to. 

I took a deep breath. 

“You enjoyed what we did, right?” Penny asked. 

I nodded. 

“And you want to do it again?” Penny asked, looking down at her salad. 

I nodded again, unable to deny the truth but unwilling to voice my shame. Penny was hot, and more than that, she was good at sex. She enjoyed me being inside her almost as much as I did. I wanted to do it again, and seeing her the way she was now, my instinct was to stand up, tear her lingerie off, drag her to the bedroom upstairs, and make her scream loud enough for her parents next door to hear her. 

Not that I had time for that. I had to get back to work, and I couldn’t precisely attend a meeting on Zoom while balls-deep in Penny. 

I resolved to end things before they got started this time, but the words never left my mouth. 

“How about we make a deal?” Penny asked. 

I raised my eyebrow, listening despite myself. 

“If I can make you cum by the end of the day, you update your Tinder profile and go on a date.” Penny said. “If I can’t, I’ll stop pressuring you to go on a date.” 

I frowned. If given the opportunity, she’d certainly make me cum by the end of the day. It wasn’t as if that was terribly difficult to do. Then again, we wouldn’t have time to be together that way. I only had a few minutes remaining in my lunch break, then I had work and she had to watch Abby. Besides that, despite her aggressive seduction methods, I could always prevent her from touching me. If I wanted to avoid dates in the future, I could. If I wanted to let her make me cum and use losing the bet as an excuse to follow through with going on a date, I could. 

“I pick who the date is with.” I said, offering some kind of stipulation as if I were considering the wager. 

“Of course.” Penny said. “But you have to go on at least one date by the end of the month.” 

I frowned, considering my options. “And if I don’t?” 

“Then I pick your date for you.” Penny said, clearly prepared for the question. “Whoever I choose, you have to go on a date with them.” 

I hesitated, wondering if she had someone in mind already. “Do you have someone in mind already?” 

“A girl I go to school with.” Penny said, smiling at my reaction. “She’s older than me, so relax.” Penny rolled her eyes. “Or, used to go to school with.” She corrected herself. “She graduated last year, but she’s planning on going back this fall.” 

“What for?” I asked, curious. 

“I’ll let her tell you if you go on a date and if she wants to.” Penny said. “Do you have someone in mind already if you go on a date?” 

“No.” I answered honestly. “I don’t even know any women my age. It’d have to be through the app.” 

“You don’t?” Penny asked, curious. “No one at work or from the bar or wherever you old people hang out these days?” 

I frowned. I appreciated Penny's attempt at humor, but not the crack at my age. Our age difference already bothered me, given the nature of the physical activities we engaged in once and what she was proposing we do today. 

“The women I work with are all taken, I think.” I said, shrugging. I could only think of one who might be single, but I didn’t know for sure. “I don’t go to the bars or clubs or whatever kids are calling it these days.” 

“You should.” Penny said, finishing her salad. “You’d clean up.” 

I rolled my eyes. We’d had this conversation before, and I didn’t believe myself to be quite the catch that Penny did, but I knew better than to argue. 

“So we have a deal?” Penny asked, reaching across the table for a handshake. 

I sighed and shook her hand. “Deal.” 

“Great.” Penny said and slid from her seat to kneel on the floor. I stood from the table, pushing my chair back, and walked toward the counter away from her. “What the fuck?” 

“I have to get back to work.” I told Penny with a smile. “So I can’t do any of that right now.”

“You can wait a few minutes, right?” Penny asked, standing up and presenting her curves with mouth-watering intent. “I’m ready to go, and Abby is down for at least an hour.” 

“Sorry.” I said, checking the clock on the stove. “I have a meeting.” 

“You’re presenting?” Penny asked. 

“No, but I need to be in attendance.” I said. “I’m helping a coworker fine-tune her presentation for our boss.” 

“Cameras on?” Penny asked. She sounded so hopeful I almost hated to dash her hopes. 

“Cameras on.” I said, confirming her fears. 

“So I can’t exactly ride you while you watch.” Penny said, frowning. 

“Sorry.” I winked at her. “Looks like I’ll win this bet easier than I thought.” 

Penny laughed. “We’ll see. Go on, get to your meeting. I’ll take care of the dishes while Abby is asleep.” 

“Thanks.” I said, leaving my dishes in the sink. 

Penny smiled and watched me leave this time. My slacks didn’t do as good a job of showing off my ass as her shorts did hers, but she still seemed to appreciate the show. 

I took a breath and tiptoed upstairs for my meeting, carefully moving to not wake Abby, sleeping in her room down the hall from my home office.

My home office was a repurposed bedroom, but the router was on the built-in counter and cabinets beneath the window. My bookshelves appeared studious, but I'd filled them with fantasy, science fiction, adventure, and romance novels. Some books were mine, and some were Charlie’s, but they looked fancy enough with their hardcovers and jackets removed. 

My desk was a repurposed kitchen table from Ikea. It lacked drawers, but the extra space was perfect for having my computer set up with a place for calculating by hand. I didn’t have much in the way of knick-knacks, but I had plenty of picture frames surrounding my desk. Photographs that captured my life from college, through marriage, through Abby’s birth, and Charlie’s funeral. Abby and I played with her toys on the floor in the most recent picture. Penny had taken that picture and sent it to me weeks ago. The same Penny I’d left in her lingerie in the kitchen. 

I sighed and woke my computer, preparing for the incoming Teams call. I had a few minutes to finish things, and the call came through. I put on my headset and answered. 

“Hey, Svetlana, good afternoon.” I said, smiling as my camera clicked on. 

“Hello, Julio!” Svetlana’s camera showed the dark-haired Russian woman sitting before a blank wall with a landscape picture in its frame behind and above her. “And I told you before, you can call me Lana.” 

“Okay.” I said, nodding. “Lana.” 

She smiled and nodded. “Are you going to the Happy Hour tomorrow?” 

The non-sequitur confused me momentarily, and it must have shown on my face. She frowned, and I shook my head. “I’m sorry, I didn’t know there was one.” 

“Bill was organizing it.” Lana said. “We’re going to O’Grady’s. That’s in your neck of the woods, isn’t it?” 

O’Grady’s wasn’t too far from my house, a ten-minute drive. Though, it was farther for Svetlana. Based on where I knew she lived, it was a half hour for her. 

“Yeah, it’s not too far from me.” I said. 

“Bill said he invited everyone…” Lana frowned. 

“He might have left me off the list because I never go.” I said, assuring her it was okay. “I’ve got Abby, and I can’t really go out drinking with her home alone.” 

“I guess it’s not reasonable to tell you to find a sitter for a night.” Lana said, frowning. 

“Eh.” I shrugged. Penny would do it in a heartbeat, but it would cost me, and paying for a babysitter on top of the overpriced drinks at the bar didn’t sound like a fun time for me. 

“I was hoping to meet you in person, finally.” Lana said. 

“What do you mean finally?” I laughed. “You’ve only been working here a month.” 

“True.” She said, shrugging. “But you’ve been the one helping me out the most. We’re practically friends, and I barely know anybody else on the team.” 

“Fair enough.” I said, nodding. “I’ll see what I can do but can’t make any promises.” 

Lana smiled. “Text me if you’re coming, and I’ll go. Otherwise, it’ll be awkward. I don’t really know anybody.” 

“Happy hours are the time to get to know our coworkers.” I said, laughing. “I used to go all the time. It can be a lot of fun. Some people bring their partners or spouses too.” 

“Oh, I don’t have anyone like that.” Lana said, shaking her head. “I’m on my own out here.” 

The information surprised me, but I did my best not to let it show. I hadn’t been confident about Svetlana’s relationship status, but I thought it reasonable to assume she was taken. 

Lana was a cute young woman. I’d never asked her age, but I’d say she was between twenty-five and thirty if I had to guess. Her mop of curly black hair was cut short, and her large brown eyes gave her a doe-like appearance. Her effortless smile with matching dimples and a sharp, pointed chin were cute, and while she wasn’t as busty as Penny, she knew how to accentuate her assets. Her button-up blouses were always undone at the top, showing a stretch of cleavage while remaining appropriate office wear. I had yet to see her from the waist down, though. 

“What about you?” Lana asked. “I know your wife passed… have you gotten a girlfriend?” 

“No.” I shook my head. 

“Still not ready to date again?” She asked. 

“No, I mean, I am, I just… haven’t really had the time or energy to meet people. You know?” I said, looking up as Penny stepped through my office door and closed it behind her. She still wore nothing but her lingerie, and she stood by the door, staring at me as I continued. “I have friends trying to encourage me to get out there, though.” 

“Then come to happy hour.” Lana suggested. “You might meet someone you like at the bar!” 

I smiled and nodded. She had a point. 

“I’ve been trying the apps, but they’re terrible.” Lana said. 

“Me too.” I said. “It’s probably a different kind of terrible for me, though.” 

“Yeah.” Lana agreed. “You don’t get random dick pics, I’m assuming.” 

“No, but I don’t get many matches either.” I shrugged. “Ah, well. Can you hold on a second?” 

“Oh, sure.” Lana said, frowning. 

I muted my mic and looked over my computer monitor at Penny, who smiled. “Is everything okay?” I asked. 

“Yeah.” Penny said. “I just had a question about the dishwasher. It’s okay to run at the same time as the laundry machine, right?” 

“Oh, uh, yeah.” I said, thinking. My hot water heater wasn’t an infinite source of hot water, but they should be fine as long as no one was also taking a scalding hot shower. 

“Okay, good.” Penny said. “You go ahead and have your meeting. Are you okay if I hang out here and read until Abby wakes up?” 

I shrugged. “Yeah, that’s fine. Just be quiet.” I pointed to my headphones. Penny nodded, and I went back to work. “Okay, Lana, where were we?” 

“Everything okay?” Lana asked, the concern in her voice enough to push me to assure her. 

“Yeah. My daughter’s nanny just needed to ask me a question.” I answered. 

“Oh, okay.” Lana said, straightening up a bit. 

“Now, you wanted me to critique your presentation before you submit it to Mike?” I asked, getting to business rather than our previous conversation. 

“Right.” Lana said, frowning slightly. “Let me pull it up and share my screen.” 

She shared her screen first, either by mistake or misclick. Her desktop background surprised me. Instead of a PowerPoint presentation, I was treated to a picture of her and two friends at a beach, their bikinis small and the drinks in their hands large. It was only there for an instant, but enough to show me she had a body worth seeing in person. 

Not that I could afford to think that way. She was my coworker, and the last thing I needed was to get fired for hitting on her. I glanced at Penny while Lana opened her presentation. She stretched to the top shelf of my bookshelf, her backside to me. My slacks tightened as she went onto her toes and fell back to her bare heels. I returned my eyes to the screen, ignoring whatever book Penny had picked. 

Lana began her presentation, and I did my best to give her my full attention. Penny didn’t make that an easy task. Her motion caught my eyes, and I saw her holding her bra high in one hand. She released it, and the mesh fell past her, but my eyes lingered on her massive breasts, now bared. 

I clenched my fist beneath my disk, trying to maintain a neutral expression for Lana’s sake. My camera was still on, but with her sharing her screen, my window was miniscule. Lana’s voice in my ears was sweet, and she transitioned into her presentation as if she were delivering it directly to our boss instead. 

My eyes returned to the screen as she changed slides to present a flow diagram. The changes she suggested to processes would take some time to implement, but they would improve efficiency while requiring minimal retraining. Sometimes, it took a newcomer’s eye to see what those accustomed to the process couldn’t. Lana had good ideas, she just needed help selling them to management. 

Penny’s gentle hand touched my knee, and I lifted my eyes to see she was no longer standing on the other side of my desk. She was under the table, on her knees. There was a hiss, and my chair lowered slightly, jostling me. If Lana noticed, she didn’t draw attention to it. I moved to push Penny’s hand away, but she pressed my knees apart. I adjusted my feet, and she crawled between them. My eyes remained on the screen, taking in Penny’s breasts in their lower peripheral as I tried to maintain eye contact with Lana on the screen. 

Penny’s hands slid from my knees to the inside of my thighs. Her thumbs dragged along as her hands moved closer and closer to her goal, and I swallowed to maintain my composure. She reached my crotch and kept going, bracing her hands against my waistband. I heard my slack’s zipper as Penny dragged it between her teeth. Her nose brushed against me, and I gripped the arms of my office chair. 

“Does that make sense?” Lana asked as she completed an awkward phrase in her presentation. 

“Yeah.” I said, causing Penny to go rigid. “That makes sense. You might want to consider rephrasing it, though, to make it clearer.” 

“Like this?” Lana asked, deleted the phrase, and then retyped the slide. 

I tried to reread the words, but my vision blurred as Penny’s tongue slid and curled against the underside of my cock. Her hot breath on its tip flooded my body with heat. The only muscle in my body that would respond to anything right now was in Penny’s mouth. I grew and hardened in seconds, harder than usual against the soft, slick cavern of her mouth. 

“Are you okay?” Lana asked, squinting at my expression on camera.

I fixed my face and nodded. “Yeah, sorry.” I said, tilting the camera slightly so it moved up, just in case. My background and face were in the shot, but nothing below my shoulders. The last thing I needed was for Lana to see the back of Penny’s head. It was probably bad enough that she saw me glaring at the back of Penny’s head. 

“That looks better.” I said, reading the retyped sentence quickly. “Much more to the point.” 

Lana smiled and resumed her presentation. 

Penny resumed her sucking. She started slow and soft, holding me in her mouth and stroking the underside of my length with her tongue. Delight shuddered through me when she sealed her lips over the mushroom head and curled her tongue against me in slow strokes. 

My toes stretched then curled in my shoes. I watched Lana’s presentation but focused more on the woman’s face. She was closer to my age than Penny’s but still young. She was friendly and had a great smile. Lana wasn’t wearing or doing anything particularly erotic. Still, every hand gesture, shoulder shrug, dimple-revealing smile, or adjustment of her neckline was sexy when paired with Penny’s blow job taking place off-screen. 

Lana’s blouse slid as she shifted, and I would have sworn I saw the white lace of a bra beneath her robin’s egg blue top. I stiffened in Penny’s mouth, and she took the signal as encouragement. She slid her lips further along my cock, taking half of it into her mouth, then withdrew until she nearly released me. She repeated the bobbing, fucking her face with my cock in a languorous rhythm. 

Penny’s tongue did most of the work, truth be told, and I sat back in my chair and enjoyed every moment. 

“So, what do you think?” Lana asked. 

I snapped back to reality and read over the last slide. A Q&A image. Lana’s face took over my screen as she stopped sharing her screen. Her shirt was open to show four-finger widths of cleavage, and my eyes lingered too long as Penny seized my cock in her fist.

“I think you’ll do a great job.” I said, swallowing. “When you present this for real.” 

Lana laughed. “Thanks. Hopefully, this will streamline that process, and we can get the real work done.” 

“More time for happy hour.” I said, smiling slightly. I tried to keep my tone even, but Penny chose that moment to start fondling my balls with her fingers, stroking me with one hand and sucking on the tip of my cock. My voice hitched, turning the statement into a question. 

“The happy hour? Does that mean you’re going?” Lana asked, smiling. Those dimples looked up at the camera, and Lana looked up at me as Penny’s eyes lifted from between my legs. 

“I’m coming.” I said, holding in the laughter at the double entendre. 

Penny seemed to think I was talking to her. She redoubled her efforts, making me grip my chair so tight I thought I might tear the arm off. 

“Good!” Lana said, missing my sudden shift in demeanor. “I’ll see you there!” 

“See you there.” I repeated, nodding and reaching for my mouse. I don’t recall ever turning my camera off faster. The groan I released was almost as satisfying as cumming. 

Penny didn’t say anything; she pushed my chair back and started sucking me off with vigor. I could see her breasts bouncing, her naked body beneath me, and still mainly under the desk as she braced herself against my lap. 

I moved my hands to her head, meaning to slow her, but instead, I pulled her to me and thrust to meet her, stroking into her throat. Finally, she made some noise, salivating on my cock as I looked down at her and felt myself growing closer to the edge. I crept toward it with every thrust into her throat and every time her nose pressed against my bush. 

Penny’s hands moved, and she reached between her legs with one hand and groped her breast with the other. The sight of her swinging breasts, the sound of her gurgling on my cock, and the squeeze of her mouth, tongue, and throat on my cock was enough to milk my orgasm from me. 

I shuddered and exploded. Penny felt the pulse travel through me and pulled away, getting one inhale into her lungs before my release launched and splattered against her face. She smiled beneath the white curtains that fell against her eyes, nose, and cheeks. 

I twitched and slumped against my chair. My eyes wanted to close, but I held them open to enjoy the sight of Penny’s face covered in my cum. She licked her lips and pulled the ropes into her mouth, then pushed them with her fingers until her face was clean. Then she sucked on her fingers, getting every last drop. 

“Did you enjoy that?” Penny asked. 

I chuckled. “Obviously, yes.” I took a deep breath. 

“Good.” Penny said, standing up from beneath my desk and patting my thigh. “I’m glad.” 

“Shouldn’t I–” I said, gesturing to her. 

“No, no, no.” Penny shook her head. “This was for our bet, remember? Now you have to go out on a date.” She smiled. “Maybe when you’re done with work, you can take care of me. I’ll stay late tonight after Abby’s put to bed?” 

I nodded. That sounded like a terrible idea to me, but I couldn’t say no. Her parents would be okay with it. They’d think I just wanted a good night’s sleep for once. Though I doubted Penny’s suggestion would lead to a good night’s rest, I couldn't disagree. 

“Unless you have a date already?” Penny asked. 

“I kind of have one already set up, but not until tomorrow.” I gestured to the computer. “I don’t know if you overheard, but–” 

“The happy hour with your coworker?” Penny asked. She’d obviously overheard at least the last portion of the conversation. “Good. I’ll want to see some pictures of you two together, or if things go well, you can bring her back here, and I’ll stay out of your way. Unless she’s hot.” 

I laughed. “If she’s hot, you’ll send her packing?” 

Penny looked confused, then laughed as she pulled her bra into place and fastened it behind her. “No, you idiot.” She rolled her eyes. “If she’s hot, I’ll join you.” 

Stunned by this suggestion, I sat as Penny strode toward me, tucked me into my pants, zipped my fly, patted my lap twice, and left. My mind couldn’t process what she’d said. It was like I was piecing the words together, a puzzle that would reveal the final image when everything fell into place. I watched her leave and bit my lip when she lingered in the doorway with her hand on her ass. 

What she’d said and the implications finally fell into place as she closed the door behind her. 

“Wait… what?” I asked my now empty office.