The Babysitter Beta

((This is something from the archives that I polished up a bit for posting here. It's a fairly typical trope-ish short smut story about a wi

((This is something from the archives that I polished up a bit for posting here. It's a fairly typical trope-ish short smut story about a widower and his babysitter, which I'd initially intended to write a whole series about. I never wrote more than this introduction story, but might continue it if you all enjoy it. The reason I didn't is that there are about a million of these on Literotica already, and there wasn't anything really special about this to make it stand out. Not that typical is bad! I just didn't think it was worth posting. So I took the idea of a sex-positive cuckquean, applied it to a different character wrapped up in a different story idea, and wrote a different series that you know and love. You might see some similar themes to Harem House, but hopefully you don't mind and enjoy this anyway!))

June was my favorite month of the year. Gone were the last chilly days of Spring; here were the hot days of summer. I know what most people say: They hate the heat and would rather freeze and layer their clothes, but I’ve always been the opposite. Give me a patch of shade on a hot summer day and a glass of ice-cold lemonade, and I’m in heaven. 

That kind of day arrived in the middle of my work day, and I made my decision. 

It was too lovely a day to spend inside, so I took my laptop and moved outside, by the pool. I was sun-lotioned up, with a bit of shade from the overhang on the patio. The pool motor was a dull hum. The bugs in my backyard kept to the grass with all the scented candles and repellents warding them off the cool gray stone. The faint odor of Chlorine was perfumed by the pollinating flowers of my garden. 

I dutifully took my laptop with me, typing away as I messaged my coworkers and sent them the spreadsheets I’d worked on. I was one of the lucky ones. My office gave up their lease rather than mandate everyone return for no sensible reason when the plague was over. Now, I worked from home and lived the dream, even if certain aspects of that dream differed from how I’d imagined them.

The sliding door to my kitchen let me know Penny was approaching, and I turned to see her stepping out of the house in a scandalously tiny blue bikini, a baby monitor in one hand and a towel in the other. 

“I see we had similar ideas.” I smiled, letting her know I didn’t disapprove. “Any trouble putting Abby down for her nap?” 

“No, she’s down for hopefully the next hour or two.” Penny said. She returned my smile as she spoke, and her eyes flicked from me to the pool. I could tell she wanted to take a dip but didn’t want to seem irresponsible. 

“Go on. Hand me the monitor, and I’ll let you know if she starts calling for you.” I said. 

“Well, actually, I was thinking about working on my tan,” she said, showing off her arms as though they proved her need for one. Penny wasn’t ghostly pale, but she was lighter-skinned than I was. Her parents were some kind of Midwestern Nordic, if I had to guess. Her pale white skin and light brunette hair were typical of the area and her family. My Latin parents would have spoken in nothing but Spanish around them to make them uncomfortable. 

“Oh,” I said, surprised. I gestured to the second lounge chair, still sitting in the sun but continuously unoccupied. I only used this one since I preferred the shade. “Well, there’s another chair if you want it. Are you okay if I stay out here?” 

“Of course.” Penny said quickly. “It’s your house after all.” She giggled. 

I nodded and did my best not to look at her as she laid her towel on the chair, her back to me as she bent over and flattened the ripples. My laptop was not terribly interesting compared to the college girl’s pale ass on display, her round cheeks emphasized by the wedged bottoms. She worked out regularly enough to make her body a beautiful work of art. Artwork I knew better than to admire. 

“And thanks for letting me spend my break tanning,” Penny said with a smirk. She looked over her shoulder, but I was looking at my laptop as she laid out on her towel. 

“Well, thank you for taking such good care of Abby,” I answered and kept working. 

“You should take a break, Mister Castillo,” Penny said, admonishment clear in her voice that reminded me of Charlie. Though ‘Mister Castillo’ reminded me this was my neighbor’s daughter. She was home for the break from college, but at nineteen, she was twenty years younger than me, and I felt old despite keeping my body in shape with the weights in the basement. 

I laughed. “I will. I just need to finish this first.” 

Penny didn’t say anything but closed her eyes and took a deep breath as she enjoyed the sun's warmth on her front side. 

I knew I shouldn’t, but I looked at her to see the front of her bikini bottoms had bunched up a little, creating a gap between the front of her waistband and her skin. I couldn’t tell if it was a shadow or the fuzz of a landing strip that matched her brunette hair peeking out. I closed my eyes and returned to my laptop. 

Penny shifted, and I glanced over. I noticed her bikini top was the same color as the scrunched material as her bottoms. Her nipples tented the tiny triangles of fabric, hardening under the warm embrace of the sun. I watched as they grew from small pokes to thicker, taller points at the end of her large breasts spilling out to either side of her torso. Her breasts were too large for her skinny frame and far too enticing. I turned my attention to my laptop and took a deep breath. 

“If I fall asleep, roll me over in about fifteen minutes,” Penny said. 

I laughed. “Sure. Charlie always fell asleep when she tried to tan.” I said it without thinking, but suddenly, I couldn’t think of anything else. 

Penny was quiet. “You miss her?” 

I laughed. “Yeah, but it’s okay.” 

Penny opened her eyes and sat up to look at me. She glanced at my hand. She could see the faint line where my wedding ring used to be, but if she’d noticed it was missing before, she hadn’t said anything. 

“You took your ring off?” Penny asked. 

I nodded. “My brother thinks I should start dating again. He set me up with a woman from his office, but… I’m pretty sure I screwed that date up big time.” 

Penny raised an eyebrow at me, and I continued. 

“I talked about Abigail the entire time,” I explained. 

“Awww.” Penny cooed. “That’s adorable, though. You’re a proud single dad. Women love that.” 

“Maybe.” I shrugged. “But showing her all of Abigail’s photos on my phone might have been too much.” 

Penny laughed. “Maybe.” She shrugged. “Her loss. You’ve got the whole good dad thing, plus a bit of a wounded duck as a widower, no offense. You should be turning women away. You’re a catch.” 

“Thanks.” I laughed. “I’ll be sure to put that on my Tinder profile: My kid’s nanny thinks I’m a catch.” 

Penny laughed. “You’re on Tinder?” 

I rolled my eyes. The interest in her voice was too keen for my liking. I knew where this was going, and I didn’t feel like having a college kid tear apart my dating profile. Then again, she might know enough to help me with it. I learned not to include fishing pictures, but that was easy since I didn’t go fishing. I’d gone as a kid, sure, but not since. 

“Come on.” Penny pleaded. “Let me see it?” 

I shook my head. 

Penny picked up her phone instead. “Fine. I’ll find you.” 

“You’re on Tinder?” I asked, surprised. 

“Yeah.” Penny shrugged. “But I use it to scope girls. The guys on these apps are…” She realized who she was talking to and smiled. “Well, there are a few worth the time, but most just want to pretend they’re players. Or they are players and treat women like crap. Bumble and Hinge are a little better, but it’s a shit show out there.” 

I nodded, discouraged by that commentary on my prospects, and returned to work while she skimmed the app. It wasn’t long before Penny broke the silence.

“Found you!” Penny said in triumph. She held up the phone and showed me my profile picture. Me, with my hands on my hips, the grill behind me, and a “Kiss the Cook” apron covering my shorts and t-shirt look. It was the best, and only good, picture of me in a single-person photo. The others were me at the bar with friends or at a work outing with coworkers. 

Things were quiet as she evaluated, and I returned my attention to work. 

“You need sexier photos.” Penny declared. 

“Like what?” I asked. 

“Like…” She gestured to me. “What you’re in now?” 

“My swim trunks?” I asked. 

“Yeah. Lie back.” Penny said. 

I rolled my eyes. “Let me finish this first.” 

“Okay.” Penny said. “But I’m taking better photos of you before Abby wakes up. You deserve to catch a sexy lady, and if you don’t mind me saying, you need to get laid.” 

I laughed. “I…” Well, it was hard to argue with that. Charlie and I had a reasonably active sex life before she passed, and it’d been one hell of a dry spell. 

“What kind of women are you into?” Penny asked. 

I coughed and did a spit take despite not drinking anything. 

Penny gave me a wicked smile and winked. She walked up to the side table and swiped my phone. “I thought I’d help you by swiping on a few.” 

“Give me that,” I said and held out my hand. 

Penny laughed and returned my phone, which I put away. She returned her focus to tanning by relaxing on her chair and raising one leg, so her foot was by her knee. The motion caught my eye, and I turned my head slightly before returning my focus to my laptop. I didn’t need to see how narrow her baggy bikini bottoms were between her legs. 

She was my daughter’s babysitter. Though, the term 'nanny' was probably more apt. She’d started as Abby’s babysitter, helping me out so I could work and survive. It had been a once-in-a-while event until I offered her a more full-time arrangement for the summer after her parents mentioned she was home and looking for work. She’d been fantastic and was still cheaper than daycare. I worried, though, about what would happen at the end of the summer. Having her was a lifesaver, and I’d need to start looking now if I wanted someone to take over when she went back to college. 

“Are you into older women or younger women?” Penny asked. 

I glared at her. 

“Are you looking for a serious, get-married relationship or casual fun?” Penny asked, continuing her inquisition. 

I sighed. “I don't know.” 

I missed my wife, the companionship, the friendship, and the kind of personal bond that came with years of love between two people. I knew I wouldn't find that on an app in the next few weeks. I would have to start casual, regardless of my end goals. “Casual, I guess.”

Penny grinned. “What kind of looks do you prefer? Big tits?” Penny hefted hers. 

I turned away and focused on my laptop.

“Alright, alright.” Penny raised her hands. “But if you wanted a sugar baby, I’m sure you could get one.” 

I laughed. I knew the term, of course, but the idea was still ridiculous. I was not wealthy enough to afford a sugar baby. I had a decent job, savings, a 401K, and an investment portfolio. My house and car were my only noteworthy assets; both were firmly middle-class suburban. However, the house was paid off, thanks to my late wife's life insurance. Still, I didn't have the dough to be a sugar daddy. Sugar daddies were people who lived in mansions and had acronyms for job titles. 

“What?” Penny asked. “Seriously. I know a few girls at college who’d jump at the chance for a guy like you.” 

“By all means, send them my way,” I said, shaking my head. I poured more sarcasm and disbelief than I meant to into it. 

Penny looked at me for a moment, sighed, but nodded. “Okay. I will.” She didn’t say the words ‘challenge accepted,’ but the tone was unmistakable. 

I shrugged and went on with my work. I didn’t think anything more about it. I'd try again on the apps later.

Penny rolled onto her front, and I finished my work. When Penny was finished tanning, she checked the monitor, but Abby was still asleep, so she looked at me, relaxing and drinking my lemonade. “Ready for your close-up, Mister Castillo?” 

“Isn’t it weird to call me Mister Castillo?” I asked. “You can just call me Julio.” 

“Okay, Julio,” Penny said. “What about Mister Julio?” 

“Is the Mister really necessary? You make me feel like I’m a hundred.” 

“You’re not that old.” Penny protested. “Okay, you’re closer to my parents' age than mine, but you're not even forty. You’re practically a youth.” Penny cracked a smile. “Besides, some girls like older guys.” 

I rolled my eyes. “Pretty sure that’s a myth spread by horny older guys.” 

Penny giggled. “I heard it’s biological. We’re predisposed to find stability and emotional maturity attractive, and you’re predisposed to find youth and fertility attractive. It’s just genetics.” She sat up and shrugged. Come on. No more delay or Abby will wake up, and we’ll never get these photos taken.” 

“Okay.” I sighed. “How should I pose?” 

Penny considered it as she stood up and walked around my chair. I moved my laptop to the table beside me and waited. “Lay back,” Penny said finally. And put your hands behind your head like you’re lounging.” 

I followed her instructions as she took out her phone. She looked at me and then climbed onto the chair, her feet on either side of my thighs as she stood over me. I looked up at her, her face and front illuminated by the sun so her shadow fell behind her rather than across me. 

“Uh…” I started, but she didn’t seem to notice how my eyes flicked to the camel toe between her thighs, the narrow strings hitched over her round hips, or the poking nipples tenting her bikini top. 

She held out her phone and framed the shot. “Look up at me?” 

I raised my eyes to her face with tremendous effort.

“Smile, Julio.” She said. “But not a cheesy smile.” She said after I smiled. I did my best to fix it, and she shook her head, her long brunette hair shifting around her bare shoulders as she did so. “Give me a smolder.” 

“Okay…” I said, hesitantly. I tried my best, but it took a few attempts before she was satisfied. 

“Hmm…” She seemed indecisive about something. 

“What’s wrong?” 

“The angle is too wide. I need to get closer,” she said. “But the zoom loses definition. Hold on.” 

That was all the warning I had before she shifted her stance and dropped to her knees, placing her shapely calves on either side of my hips. The gap between her camel toe and my trunks was several inches of smooth, toned thighs, and my body stirred in response. It’d been a long dry spell, and my body was hungry for something Penny wasn’t offering. I inhaled deeply through my nose, taking in her lush perfume with a tang of something I couldn’t identify. Something that my body responded to without any conscious effort. I had to physically resist burying my face in her. 

“Ooh, that hurts my knees. Hold on.” Penny scooted forward, her knees on either side of my navel, then dropped back so she was sitting on my lap, her crotch against mine. “Is this okay?”

My body responded, all of my blood draining to one specific organ, which reared in response to her warm contact. 

“Oh, Mister Castillo.” Penny blushed. 

“I’m sorry,” I said. “It’s just…” 

“Don’t apologize.” Penny shook her head. “You have nothing to be embarrassed about.” Her dismissal took me by surprise, but I was too embarrassed to say anything more about my dick. 

She smiled, and I gave her an awkward smile in return. She took another photo. I did my best to lie back and calm myself. I was nearly settled when she shifted, sliding forward against my length and rubbing herself on me. My eyes flared, and Penny smiled. 

“Are you okay?” She asked. 

“Yeah, just… try not to move around too much,” I said, lying back. 

“Oh, I don’t know.” She rocked her hips forward again. “You seem to enjoy it when I move around.” 

My dick throbbed against her. I knew she could feel through our swimsuits, but she didn’t seem bothered by my arousal. If anything, she seemed to want to tease or please herself with me. I wasn’t sure how to process that, so I said nothing. 

“Try closing your eyes like you're relaxing,” Penny said. 

I closed my eyes, but relaxing was impossible. Penny was on top of me, her weight pressing her pussy onto my cock, and my dick wanted to tear through the thin layers separating them.

“Good. Now keep your eyes closed, but look smug.” 

I did my best, giving her a closed mouth half smile. Penny seemed to appreciate that look, and she snapped away as she started rocking against me again, driving her hips back and forth until I gripped her thigh. 

“I think that’s enough photos,” Penny said. 

I released her thigh, but she caught my hand and placed it where it was. Her bare skin was electrified with goose pimples under my touch. I stared up at her, and she sat straight. 

She turned her phone around and showed me the pictures, swiping past each one slowly and starring any I said I liked. She remained where she was the entire time, her bikini-clad crotch sitting on my trapped length, harder than the stone tile beneath the chairs. Her arm jostled her breasts with every swipe, and I was starting to think she was doing it intentionally. 

Then Penny reached the end of the photos she had taken of me but didn’t stop swiping. She grinned as she swiped to a picture of herself in bed, covered by only a sheet. 

The next showed the sheet lowered, revealing the top of her enormous breasts and her cleavage. The two spherical mounds beneath the sheet tented the material by her nipples. 

She shifted, sliding forward against my length before she swiped to the next pic and slid back.

The following picture showed her with the sheet lowered even further, exposing her entire torso and two rigid, eraser-tipped nipples. Her areolas were larger than I expected, but the two perfect circles were pink roses complimenting her pale breasts. Her stomach, beneath her large breasts, was bare, showing the lines of her abs and hips. The sheet corner rested over where her pussy lips must be, exposing every other piece of skin on the front of her body from head to knee. 

“Oh, you like that one.” Penny giggled. 

I was surprised my dick hadn't torn a hole through my trunks. It certainly wasn't for lack of trying. 

She swiped, rocking her hips against me again. This time she was naked, relaxing in bed with her hair over her shoulder, her breasts exposed, one hand raised above her head, and one hand covering her pussy. No, fingering herself. The following photo was the same, but from a lower angle, showing her knuckle-deep in her spread pink pussy lips. The light caught the moisture on her thighs, moisture I felt against me now. More than the pressure, she was like a furnace on top of me, and when I looked up into her eyes, I saw the fire there. 

My eyes went wide, and I forgot to breathe until my body started to panic at the lack of oxygen. The deep breath made my chest rise and fall noticeably, and Penny bit the corner of her mouth. 

Penny kept swiping, showing me picture after picture of her naked and displayed. Her gorgeous body was far too tantalizing while she was still on top of me. 

“Oh, you like those pics too, huh?” She asked, rocking her hips forward. She swiped, showing me a picture of herself arched on her bed, a dildo in her hand. The next couple of photos were her fucking herself with it, even as she ground against me, closing her eyes and tilting her head back. “Do you want to fuck me, Julio?” 

My brain knew the answer should be no, but even as my lips formed the words, the rest of my brain strangled them in my throat. 

“Just something casual. To give you some relief.” Penny said when I hadn't spoken. “A bit of fun between two horny neighbors.” 

I turned my head, looking at her house. Her parents’ house. Parents who had no idea what we were doing right now. Parents who trusted me. She was nineteen. A legal adult. Yet they probably didn’t know about this side of their little girl. Her parents would likely kill me. I couldn’t die. I had a daughter of my own to look after. 

“No one can see us. Your privacy fence is solid, and the only thing you can see from my second-story window is your second-story window since you're at the top of the hill,” Penny said. Believe me, I've tried to spy on you in your pool before.”

“You, what?” I asked, confused. 

“Don't worry about it.” Penny shook her head. “Just answer me. Don't keep a girl waiting like this…” She ground against me again. “Yes or no?” 

“I–” I should have protested. What she suggested could have gotten us into a lot of trouble. There was no sane reason to say yes other than biological necessity. My body physically wouldn’t let me say no. My lips refused to form the word. 

“Yes,” I said, quicker than I should have. 

Penny put her phone down and closed her eyes. She held herself upright with her balance alone, moving her hands behind her and untying her top. She let the fabric fall as her hands cupped her breasts. 

I lay there, stunned, watching, stupified as she teased and tugged her nipples. 

“Do you like my tits, Mister Castillo?” She asked. 

“Uh…” I did, but I cringed at the formal name again, and she noticed. 

“Sorry.” She said. “I've just called you Mister Castillo in my fantasies. I'll get used to Julio. I promise.” 

I nodded, then paused, propping myself up on my elbows. “Your fantasies?” 

She closed her eyes again and rocked her hips harder against me. “I've been thinking of you since I went away to college. I've regretted not flirting harder before I left. Remember my 18th? You let me and my girlfriends use your pool to throw a party?” 

I nodded. I'd given the girls their space because I figured they didn't want me hanging around at their teenage party. Her parents provided the food and soda, I provided the location, and Penny had fun with her friends while I spent the night inside. 

Penny and I had only spoken briefly that night in the kitchen. She'd been wearing an even more revealing swimsuit than the one she had half on now, showing off for her friends, reveling in turning eighteen, and being an ‘adult’ a few days before the party. 

“Yeah. I remember.” I said. 

“I wanted to hit on you then, and I tried, but I didn't know what I was doing or how to broach it. And your wife–” Penny stopped herself.

My wife had passed away too close to that for me to have noticed anyone else, and I was too depressed and tired to do anything. However, with another year and a few months gone by, I'd decided to put myself out there again, and here I was. Most guys would have killed to take my place in this situation, and I wouldn't blame them.

I had a stacked college coed riding my lap, soaking my trunks through her bikini briefs, topless. Her flat stomach was toned, her waist tapered and narrow, her hips round, her ass and tits the kind of perfection you only saw on Instagram or Only Fans. I focused on that and found I was too horny to be sad at the memory of grief, so I let the moment pass. 

Penny changed the subject for me. “Just know you've been a fantasy of mine since that night. I've gotten off to the idea of what might have happened if I’d been braver more than once, and now… we're here.” 

I nodded. 

“So… Julio, are you going to fuck me?” Penny asked. 

“Yes,” I said. “As soon as you take off those bottoms.” 

Penny smiled and reached between us. She tugged my trunks, pulling them down my thighs. I pulled the drawstring, loosening the waistband. My cock sprang free as she lifted herself off, standing on her knees. She untied the sides of her bottoms with one extended pull from each hand. The fabric fell away, and she tossed her bottoms onto the patio beside us. 

Nude and wonderfully bare to my gaze, I scanned her body. She was fit, with all the beauty of youth. Her skin was flawless. She reached behind her head and pulled her hair back into a ponytail with a scrunchie from her wrist. Then she leaned forward, resting her hands on my chest and curling her fingers through my chest hair. 

She closed her eyes, moaned, and lowered herself against me. My shaft didn't enter her but pressed against her folds and slid against them, parting them. She was wet, and her pussy felt like a furnace hugging my cock.

“Come on, Mister Castillo.” She whined. “Fuck me.” 

“I don't have a condom on me,” I warned her. “They're inside.”

“Don't be stupid. I've got an IUD. Fuck me.” Penny said and ground against me.

I reached between us, angled my cock against her so the tip pushed her lips aside. I braced myself. This was the point of no return. There was no unfucking someone. I hesitated, but Penny didn’t. She felt the tip of my cock parting her lips and pushed back, taking several inches of me into her in one go.

I wasn't particularly well-hung, but I could at least claim to be above average in length. Not by much, but every inch counted. My girth was something Charlie had complimented more than once, so I took pride in that. Regardless, it seemed more than enough for Penny. Sliding into her was like pushing my cock through a too-small steel ring, but it was bliss with her natural lubrication and heat.

“Fuck.” I whispered as her insides gripped me from every direction. She rocked forward, and I made a noise, inhaling sharper than I had meant to. “Fuck.” I said again. 

Penny giggled. “Mmm. We’re going to,” she said. She rocked her hips, undulating her torso as she leaned back. She practically belly-danced on my lap, resting her hands behind her on my thighs just above my knees. “Oh, Mister Castillo.” 

I didn't care about the name anymore. So long as she said it in that same high-pitched, breathy voice, she could call me someone else’s name for all I cared. I closed my eyes and realized doing so prevented me from watching as she rode me. I opened them to see her groping her right breast with her right hand, watching my expression. 

“Help a girl out?” Penny asked. 

I felt guilty for not doing more to pleasure her. I was supposed to be the more experienced one, but something told me she'd been more adventurous in her short time of sexual exploration than I'd been. Charlotte and I were college sweethearts, and we'd met during freshman year. I had only ever been with her. I didn't know what Penny liked or didn't, so I'd done nothing. I'd laid back and let Penny do all the work. It was time to start putting in the effort. 

I planted my feet beside my chair, spreading my legs and hers. Then I thrust my hips up to meet her as she rocked her clit forward against me. That drove a delighted gasp out of her. 

My hands found her breasts, and I mirrored her motions with both hands supporting her pillowy mounds. I trapped her hard nipples in the slot between my thumb and forefinger and squeezed. 

Penny gave a sharp mewing sound and leaned forward, holding herself up on my chest and adding even more pressure to her breasts. 

“That feels so good, Mister Castillo. Oh, God. You feel so good.” Penny said in a whisper. 

I thrust further into her with my hips and started matching her rhythm, thrusting as she rocked to meet her. Her breathing turned into a steady panting as she increased her pace, and I realized she would outlast me.

It had been years, and with all of my responsibilities, I didn't have time to relieve myself properly on a regular basis. To be honest, I was surprised I lasted this long, but the chair wasn't the most comfortable for this kind of thing. 

“I'm going to…” I started but grunted and cut myself off as she rocked double time.

“Oh yes, Mister Castillo. Cum in me. Cum for me. Fill me.” 

Penny pressed herself low against me, pushing my hands with her body until her lips met mine. Her tongue plunged into my mouth, wrestling my breath away. She dragged her teeth across my bottom lip as she withdrew, pushing my shaft deeper into her as she clenched and milked my cock with her tight pussy.

I moaned and exploded inside of her, opening my mouth to gulp in relief, swallowing as much air as I could. Penny leaned back and rubbed herself, groping her breast again. I reached between us and used my middle finger to toy with her clit. 

She froze for a moment, holding onto me and squeezing me with her thighs. Then her orgasm broke as I thrust into her and gently pressed against her clit with my finger. She spasmed, and her entire body seized. Her insides wrang the last drop of cum from my still-hard cock, and she collapsed forward.

I caught her and lowered her with me until she lay with her head on my shoulder. Her heavy breasts were soft against my chest and stomach. She curled her fingers gently through my chest hair, making soft circles with her fingertips. 

We lay in silence as our breathing softened. My mind replayed the events, still disbelieving my reality. I just fucked my nineteen-year-old neighbor and nanny. I wasn't sure whether to feel proud or disgusted with myself, and the two options teetered the precipice between adulation and shame. Was I dating a nineteen-year-old now? 

At thirty-nine, society would not approve. Penny's parents would disapprove. I wouldn't have approved it if it had been someone else. This had been a moment of lust and weakness, and–

“Hey, stop panicking,” Penny said softly. I can feel your heartbeat, you know.” 

I looked over to see Penny watching my face, which I hadn't controlled as my mind imagined the ostracization I had coming and rightly deserved. 

“It's ok, I won't get pregnant,” Penny said. 

“I'm not worried about that,” I said. “I'm worried about everything else.” 

Penny smiled and ran her finger along my chest. “What do you possibly have to worry about?” She asked. “You should be on cloud nine right now and super relaxed. Did you fake your orgasm? I’ve got stuff leaking down there.” 

I laughed. “I didn’t fake it. I just meant… I’m worried about how people will react. You’re nineteen. I’m thirty-nine. They’re going to think I–” 

Penny shook her head, cutting me off. “I climbed on top of you and led the way every step of the way. This is my depraved fantasy, not yours.” 

“Well… I mean…” I didn’t like labeling the idea of us being together as ‘depraved,’ but she had a point. Society would certainly think this was depraved. And to say I wasn’t a participant in the fantasy would have been incorrect. I’d been thinking similar thoughts since she stepped onto the patio in her bikini. 

“Okay, both of our fantasies.” Penny kissed my cheek. “But don’t worry, and don’t panic on me.” 

I nodded and did my best to relax. Penny was a calming presence in that regard, warm and comfortable, like a weighted blanket on top of me. She ran her fingers in circles through my chest hair, and her breath warmed my chest in a soothing, rhythmic beat. 

“So… what now?” I asked. 

“I go to the bathroom and return to work, assuming Abby wakes up soon?” Penny asked. 

“No, I mean… between us. Are we dating now? Should we go to dinner?” I asked. “Who do I hire as a babysitter if I take you out on a date?” 

Penny laughed, then looked apologetic. I realized I hadn’t controlled my reaction to her laughter and must have looked upset. 

“We're not dating,” Penny told me. "We're just having fun. Don't overthink it.” 

“Just having fun?” I asked. 

“I'm nineteen, as you pointed out.” Penny booped me on the nose. “I’m not looking for anything serious, not in the market for a boyfriend, and I'm certainly not ready to be a wife or mother. Hell, even being a babysitter is too much sometimes.” 

I raised an eyebrow and looked at her. “It is?” 

“Don’t get me wrong. Abby is a great kid, but she’s three. She can be a nightmare.” Penny held up her hands in surrender. 

She was not wrong. 

“Are you still her nanny?” I asked. “Did I just… sleep with my employee? Am I going to jail?” 

Penny laughed again. “Technically, I’m an independent contractor. And no one goes to jail for consensually fucking their employee. And yes, I still want to be Abby’s nanny.” 

I nodded. Okay, that was something. However, the logistics of everything still bothered me. “What are we supposed to tell people? Your parents?” 

Penny shook her head. “It's none of their business.” 

“So we don’t tell anyone?” I asked. “We keep what just happened a secret?” 

“We don't need to tell anybody anything,” Penny said. “As far as anyone is concerned, I'm just helping you out, so let me help you.” 

“Help me?” I asked, raising both eyebrows now. 

“Yeah. I'll be your nanny and help you have fun.” She wiggled against my leg. “If you want.” 

“Why?” I asked. “Aren’t there guys you’d rather be with your age?” 

“Because that was amazing, and I want to fuck you again,” Penny said, stating the obvious. The ‘Duh’ was unspoken but very much understood. “Do you want to do that again?” 

“Yeah,” I said almost too quickly. 

“Then let's do that,” Penny said. She smiled and looked at me in a way I couldn’t discern. Part amusement, part something else. 

“So what are we to each other?” I asked. “Are you my girlfriend now?” 

“I'm your nanny and your friend that you sometimes fuck.” Penny shrugged. 

“Like friends with benefits?” I asked. 

“We use the term fuck buddy now, old man, but yeah.” Penny giggled and rolled off me, picking up her swimsuit pieces as she moved across the patio. 

“But we're not dating,” I said to clarify. 

“No.” Penny shook her head and pulled her bikini bottoms on, tying the sides one hip at a time. 

“Okay,” I said, watching her get dressed as my cock began to stir again. 

“Okay.” Penny echoed. “Are you okay?” She asked, and I realized I’d been watching her breasts as she dressed, frowning as she slipped her top on. 

“Yeah. I'm just... still processing all this,” I said, which was true. I was having a hard time wrapping my mind around what had just happened and what it meant for the future. Even the current conversation was boggling my mind. 

“Okay. I'm going to hit the bathroom before Abby wakes up. I'll send you those pictures for your app profiles,” Penny said as she tied her top behind her. 

“What?” I asked, confused at the non sequitur.

“Your dating profiles. Duh.” Penny said. She held her phone to me and mimed swiping as if on Tinder. 

I nodded. “Oh… Okay.” That made sense. She’d taken them for me, after all. Then again, that was before we'd done what we did. “Wait. You still want me to pursue other women?” 

“Of course!” Penny tucked her phone into her top. “Just one condition.” She said as she gathered her belongings. 

“What condition?” I asked, still in a haze. 

Penny walked away, stopping at the sliding door to my kitchen and looking over her shoulder at me. “If you fuck them, you have to tell me all the details the next time you fuck me.” 

I didn’t know how to respond to that. My cock did, but my brain short-circuited. I stared at her and realized my mouth was open. 

Penny giggled, laughing at me as she stepped through the door and closed it behind her. She pressed her ass against the glass, giving me another look at her. Then she walked away and disappeared into the house. 

I was quiet as I laid back in my chair and took several deep breaths. “What the fuck?”