The Babysitter Beta 06
Added 2025-01-08 13:07:01 +0000 UTCIt took five seconds for the panic to set in on Saturday morning. My phone read 6:04 AM. I had three missed messages.
Penny: I hope your date is going well!
Penny: I haven't heard from you, so I assume your date went well!
Penny: It's nearly one in the morning, so I'm guessing wherever you are, you're spending the night. I'm set up in the guest room. Have a great night, Mister C!
I had not planned to spend the night. My battery percentage was at 5%, and I had a naked woman on either side of me. Anne, on my left, lay naked between me and the door. Lana, on my right, also nude, wrapped her arms around my bicep and trapped my hand between her thighs. Both women were still asleep despite my movement.
They proved heavy sleepers as I stole from the bed, slipping my arm out of Lana’s grasp as carefully as possible. Anne grunted in protest as the mattress moved when I shifted my weight to climb over her, but she rolled into the warm, vacant spot, a sanctuary from the air conditioning in the house. I pulled the blanket over them and left a hastily written note on one of Anne’s post-it notes.
‘Sorry, I had to leave without saying goodbye. I have to get back to my kid - Julio.’
I wasn’t sure if Lana had found the note I left her in her room, but either way, I found my clothes, pulled them on, and left the house. I locked the doorknob behind me. Once in the car, I plugged my phone in to charge and texted Penny, hoping she’d sleep through it.
Mister C: I am so sorry! I didn’t mean to fall asleep! I’m on my way home now. If Abby freaks out because I’m not there when she wakes up, tell her I’m on my way home. Maybe lie to her and tell her I’m sleeping upstairs?
I didn’t like the idea of lying to my kid, but I hadn’t spent a night away from home since Charlie died. For all of Abby’s remembered life, I’d been there when she woke up every morning. This was the first time Penny would be beside her bed instead of me. Guilt settled into my bones at the thought of abandoning my responsibilities as a parent for the fleeting pleasures of sex with not one but two beautiful women.
I drove faster than was strictly legal and pulled into my driveway at 6:42 AM. The lack of traffic on the twilight roads made for easy passage. I considered myself lucky there weren’t any cops out that early in the morning in suburbia. Cops liked to sleep in on Saturdays, too.
I unlocked the door as quietly as I could and paused. I didn’t hear crying. That was a good sign, right? I left my keys on their hook and closed and locked the door behind me out of habit. I crept quietly through the house and climbed the stairs, peeking into Abby’s bedroom. She was still asleep. She must have had a late night last night, which was not a surprise since I wasn’t here for bedtime like I’d hoped to be.
I descended to the guest bedroom downstairs. The door was open, which surprised me, and Penny was asleep under the blankets, looking peaceful and gorgeous with her hair fanned out behind her on the pillow. I breathed a deep sigh of relief and went into the living room. I sat in the armchair and caught my breath as the panic in my chest ebbed.
“Mister Castillo?” Penny’s voice was nearly a whisper.
I looked up to see her stepping toward me, a sheet wrapped around her and the spaghetti straps of a tank top loose among the long brown hair flowing over her shoulders.
“Hey!” I said, whispering back as I jumped to my feet. “I’m so sorry about not keeping in touch last night and staying out all night. I really didn’t mean to, I–”
“It’s okay, Mister Castillo.” Penny said, holding up her hand. “I didn’t mind spending the night. I trust you and Lana hit it off?”
I nodded, a bashful smile creeping across my face as I looked away. Talking to Penny about it felt strange, considering our relationship as… friends(?) with benefits. I still didn’t know how to describe it.
“Did Abby go down okay?” I asked.
“She was a bit of a handful.” Penny admitted. “She really didn’t like me reading the stories instead of you and fussed a bit.”
“I’m so sorry.” I said again.
“It’s okay.” Penny assured me. “That’s the job.” She smiled. “I got her down eventually, but she might sleep in a bit this morning.”
I nodded. That made sense. Abby was a heavy sleeper, and I was fortunate for that, but any deviation in schedule had the potential for disaster when it came to toddlers. If we were lucky, later to bed would mean late to rise, and we could relax for a little while before the day started.
“I’ll pay extra for the overnight, of course.” I said.
Penny smirked. “Give me the details of your date night and the usual rate, and we’ll call it even.”
I almost laughed. “You want the details?” I asked, surprised. “You want to hear all about me and some other woman? Are you sure?”
Penny bit her lip and nodded. “I want to hear every sexy detail.” She dropped the sheet she’d wrapped around her, revealing her luscious body in all its glory. The white camisole tank top she wore stretched over her tits, making the material transparent near her large nipples, which peaked over the ridiculously low neckline and poked through the cotton. A wide strip of flesh lay between the bottom of the short cami and the waistband of her faded white and pink floral-patterned panties.
I glanced behind her, but Abby was still asleep, so I couldn’t protest too loudly. I was more confused than anything. My body reacted of my own accord and moved to stand, but she gestured for me to stay put. She moved between my legs and dropped into a crouch with such force her body jiggled with the motion, which made my body react again. I hardened in my slacks, and Penny worked to uncover me as I gripped the arms of the chair.
“Tell me all about your date, Mister Castillo.” Penny said, keeping her voice low and husky. “Every sexy detail. Don’t leave anything out.”
I nodded and started relaying the story.
Penny started stroking me as soon as she had me free from my slacks. I did my best to describe the bar, the brief coworker reunion, and the conversations. I described the bookstore date, and Penny sucked the tip of my cock, pumped, and kept eye contact, listening.
I hadn’t showered since my activities with Lana and Anne, but if she tasted anything strange on me she didn’t mention it. She kept sucking, taking more of me into her mouth as the story went on. Occasionally she’d pull me from her mouth and circle my cockhead with her tongue before sucking on me again. I closed my eyes, enjoying the sensations and letting her distract me from retelling the story.
“Keep going.” Penny said, stroking me.
“Are you sure you want to hear about this?” I asked, uncertain.
“Please?” Penny asked. “I… I’m getting really turned on right now. Like… really turned on.”
“Me too.” I said, though she could tell how stiff I was in her hand.
“Do you want me to ride you while you tell me the story?” Penny asked.
“I’m… not sure I can tell the story and have sex at the same time.” I said. “That’s a bit like patting my head and rubbing my stomach. I’ve never been good at it.”
Penny giggled, then sucked on me, and pulled free again after a long stroke with her tongue. “Tell me the story then. Do you mind if I keep doing what I’m doing?”
“No!” I said quickly. “I don’t mind.”
Penny smiled and shifted to her knees between my legs. She spread her legs slightly and dipped her hand between them, rubbing herself while she listened and sucked my cock. Her ability to multi-task surpassed my own. It was difficult for me to recount the details aloud already, but with a gorgeous girl like Penny keeping eye contact with me while she wrapped her lips around my cock and dimpled her cheeks with suction? Fuck.
I defy any man to concentrate on storytelling with a beautiful woman’s face pleasuring his cock while he works.
My retelling was more summary than anything. I didn’t do the voices but kept in the sexy details. Penny’s dedication to sucking me while I told the story made my arousal overwhelm my sense of shame. She rubbed herself furiously between the legs as I described Lana’s orgasm, and her eyes widened as I retold my introduction to Anne. I described making the video with her, and Penny moaned onto my cock, making me explode in her mouth. She drank everything I gave her, swallowing every last drop with my cock still in her mouth.
She came when I finished the story, fingering, rubbing, and groping herself as she finally released my cock to breathe. She fell forward and rested her head on my thigh, nuzzling my cock with her nose and smiling.
“That uh…” I hesitated, not wanting to break the spell of post-orgasmic bliss that hung between us. “That really got you going, huh?”
Penny blushed. I felt the heat in her cheeks warm the inside of my thigh.
“I can’t explain it.” She said. “But yeah. It really does it for me. The thought of you being with them? The reason I was up until one in the morning was I was fingering myself silly, imagining you and Lana fucking each other at some hotel or the bar bathroom.”
“You don’t imagine yourself instead?” I asked, surprised. The idea of Penny with another man drove me crazy in the entirely opposite direction. I didn’t think it was sexy at all. The mental image infuriated me. It shouldn’t. I had no claim over Penny, and I knew that. I couldn’t. Yet…
“Sometimes.” Penny answered honestly. “But… I don’t know. I loved hearing about your conquests last night. It turns me on knowing you have that kind of game, and… I don’t know… My fantasies started picturing you and…”
She dropped off, not finishing her sentence.
I waited, unsure what she would say until my mind pieced the puzzle together for me. Her earliest fantasies had been of me and my late wife, whom she didn’t want to mention for fear it might make me sad. It didn’t, but honestly, it was hard to feel anything other than satisfaction with her head against my thigh and my balls spent.
I ran my hand through her hair, brushing her scalp with my fingers.
“Do you have to get home right away?” I asked.
Penny smiled softly. “No. I let my mother know I’d be staying the night last night because you had too much to drink at your work thing and might need help this morning. So, if she comes over, act hungover.”
I chuckled. “Good to know I have such a dedicated babysitter.” I sighed. “I don’t deserve you.”
“Yes, you do.” Penny said. She climbed upward until she was sitting in my lap, hugging me, and I hugged her to me, wrapping my arms around her.
“Thanks for telling me the story, by the way.” Penny said. “Was any of that true about the threesome, or were you just saying it to get me off?”
“Oh, it all happened.” I said, surprised myself at the reality.
“Do you know the girl’s performer name?” Penny asked. “I want to see that video as soon as it comes out.” She bit her lip. “You’re so fuckin’ hot, Mister Castillo.”
I sighed, laughing at the pang of annoyance that came with the formal name spoken with breath that smelled like my cock. My love life was complicated to the point I no longer understood it.
Anne was the simplest. A performer at heart, she wanted me for a video we’d made together. Cool. I might never see her or sleep with her again. I had no idea what the future had in store, but it wasn’t like I was looking to make a career change to a porn star, so a relationship with her was out of the question.
Penny was a bag of mysteries. Young at nineteen, she clearly had a schoolgirl crush on me, her neighbor. She worked for me, which complicated things, and her casual sex arrangement kept leading to less casual intimate moments like this one. Where we were cuddling in the armchair together, holding each other close, and breathing so softly, we might fall asleep together. She enjoyed fucking me and apparently enjoyed hearing about me fucking other women.
Somehow, I was annoyed that she wasn’t jealous. I chose not to analyze that too deeply.
Then there was Lana. She should have been simple but was only slightly less complicated than Penny. Lana was my coworker, who seemed open to the possibility of a romantic relationship but was far from traditional. She was sexually liberated and proud of it. She’d claimed sex was an essential factor to her in a relationship, and from what I understood, I’d passed her test.
Should I call her? Should I wait for her to call me?
It was tough to worry about it with how drained and satisfied I felt and how comfortable and warm Penny felt against me, but I did my best until I fell asleep.
I woke up nearly an hour later to the sound of Abby crying. It wasn’t her hurt cry or even her angry cry. It was her ‘I’m awake and would like attention now, please’ cry. I spoke fluent toddler.
Penny flew off my lap as she woke. I didn’t remember falling asleep, and she hadn’t intended to either, but she flung the blanket around herself.
“I’ll take care of Abby.” I said, calmly rising and fixing my trousers. “You go get dressed.”
Penny smiled at me and ran into the hallway. I heard her shut the guest room door a few seconds later as I made my way upstairs to Abby’s bedroom.
The morning was more or less the weekend routine, but an hour later than its usual start. Additionally, there was an extra pair of hands to help with breakfast, and Penny played with Abby while I took my morning shower. The difference an extra pair of hands made amazed me. I had a decent handle on breakfast and always took care of Abby by myself on the weekends, but having a second adult there made everything easier.
After my quick shower, I took over for Penny and sent her home, which caused Abby to throw a fit. She wanted Penny to stay and play with her, but I didn’t want to monopolize Penny’s time. Penny stayed anyway, deciding she could spend the day, but she had plans that night she wanted to keep. She went home after we put Abby down for her nap. Abby didn’t notice her absence when she woke up, happy to have my full attention. We played, as usual, and eventually, Abby and I settled into our nightly routine.
I put Abby to bed on time that night and took a beer out to the pool with the monitor, just in case. It’d been a fun day, but I was tired and wanted to relax by the pool before the sun vanished. I enjoyed the red tint on the blue sky’s edge with an hour or so left of summer sunlight. I listened to my audiobook with an earphone in one ear as I lay on my back patio. I closed my eyes, and what seemed like a moment later, I heard the gate.
I expected it to be Penny, who must have come over for a swim. She and her parents had access to my pool whenever they wanted it, and I was in no position to protest. To my surprise, when I opened my eyes, I saw that it wasn’t Penny, but her mother, Amanda, who approached. She dressed for a swim with a white cover-up wrap over her shoulders and around her waist, covering a red swimsuit beneath.
“Oh, I’m sorry.” She said. “I didn’t realize you were out here.” She pushed a flyaway hair strand behind her ear.
“That’s okay.” I said, raising my beer. “I’m just relaxing. Abby’s down for the night, and I was thinking of doing some laps myself. Or, more realistically, staring at the pool until I convince myself it’s too late to swim, too inconvenient to change into my trunks, and I should go to bed.”
Amanda laughed at my procrastination joke. It wasn’t that funny, but I didn’t mind if she humored me. It was my pool, after all.
“Hair of the dog, eh?” She asked, pointing to my bottle.
Confusion flickered across my face, but I remembered that Penny told her mom I needed help in the morning because of being hungover. I laughed. “Yeah, I guess so.” I shrugged.
“You haven’t been drinking often, have you?” Amanda asked. “This is the first time Penny’s mentioned your drinking, and I’ve never known you to be a heavy drinker like Tim.”
I shook my head. “No, I’m mostly a social drinker, or I’ll have a beer or a glass of whiskey on a night like this to relax and unwind.”
“I’m that way with weed.” She said. “I never went in for beer.”
Weed was legal in our state, but it still surprised me. Amanda always struck me as a typical suburban mom. It was hard to picture her as the party type. She had brown hair, like Penny’s, though she sometimes dyed it blonde, red, or raven black that one time. She experimented with style, too. Tonight, it was up in a bun with her natural chestnut color. Stray locks whipped about in the breeze.
She was younger than Tim, her husband, by about six years, which put her about five years older than me. Tim had thrown her a massive party for her 40th birthday, but she’d kept her birthdays quiet in the five years since. Tim’s fiftieth was just a few months ago. At forty-four, she was the definition of MILF to a lot of young men in the neighborhood and was probably a dozen years away from cougar status.
I couldn’t help but compare her to her daughter. She was smaller up top than Penny, with flatter, rounder breasts but bore wider hips and a butt that was roughly the same size. Her stomach wasn’t as toned or flat as her daughter’s, but she was in good shape. Similar but different body shapes, and Penny was obviously younger and in better shape. Not that Amanda was in bad shape, just… older. I couldn’t criticize. That much was for sure. I did my best to exercise and stay fit but was far from a twenty-something gym rat.
“Do you mind if I do a few laps?” She asked. “I know you said we can use it whenever, but–”
“That’s absolutely fine.” I said, nodding. “Do you mind if I stay out here a while? I was hoping to enjoy the warm weather.”
“Of course! It’s your pool!” Amanda said as she set her things on a chair two seats over from mine. “I just find swimming so meditative and peaceful, but it’s hard sometimes to make time for it.”
“Tim doesn’t swim?” I asked, curious.
“Not if there’s a game on, a commentary about a game on, a guy’s night to be had with his buddies, or any other excuse, no matter how flimsy.” She rolled her eyes. “And Penny sometimes joins me, but she’s out with her friends.”
“Oh?” I asked.
“Some of her friends from high school.” Amanda shrugged and opened her towel, laying it over the chair. “Do you swim a lot? Or do you tend not to since it’s your pool and you’re so used to it?”
“I swim sometimes.” I said. “Not as much as I’d like, I suppose.”
“Well, feel free to join me.” Amanda said. “Have you had dinner yet? I was thinking of ordering some pizza.”
“I ate earlier.” I admitted. “But thanks. If you’re hungry, I have some leftovers in the fridge or–”
“Oh, no. I’m not about to take food out of your fridge. That’s for you and Abby. Penny probably eats her share, too.”
“She’s welcome to it.” I assured her. “She’s been an absolute godsend with how she and Abby get along.”
Amanda smiled. “Penelope’s always been good with children.” She chuckled. “She’ll be a much better mother one day than I was.”
I smiled, not quite willing to laugh at the self-deprecation or the mental image of Penny as a mother. She was still so young, even if she was legally old enough. Amanda had been twenty-three or twenty-four when Penny was born, not much older than Penny was now. It was weird to contemplate.
“You didn’t do such a bad job.” I assured her. “She’s already like a mother to Abby, the poor girl. I promise not to work her so hard next week.”
“Oh, she doesn’t mind.” Amanda assured me as she sat on her chair, facing me. “Penny loves coming over here, and she loves Abby. She’d probably move in and be your live-in Nanny if you wanted.”
I laughed.
“Which may not be a bad idea if we sell the house.” Amanda added.
“You’re… you’re thinking of selling?” I asked, confused.
“Penny didn’t tell you?” Amanda asked.
I shook my head and sat up, pulling my earphone out of my ear and giving Amanda my full attention as I put it away in its pod charger.
Amanda rolled her eyes as if Penny should have told me this already. “Tim got a job in Indiana. He’s moving there at the end of the month.”
Tim was moving? “But not you?” I asked.
“No.” She said. “I was thinking about getting my own place. Maybe a condo in the city or moving in with my sister.”
“Are…” I started to ask but stopped myself. It wasn’t my place.
“Penny didn’t tell you we got divorced?” She asked.
I shook my head. I’d been about to ask if they were okay, but her question answered that for me. Not only were they not okay, but they weren’t getting divorced; they already were. “No, she uh… never mentioned it.”
Amanda rolled her eyes. “That girl.” She tsked. “I think she’s still in denial. She loves her dad, but Tim is…” She looked like she was trying to think of a nice way to say it. “Not my problem anymore.” She giggled. “I dumped him, his mistress dumped him, and he’s found a job in another city.”
“Are you and Penny going to be okay?” I asked.
“Us? Oh, we’re fine. This has been months in the process. I make most of the money, but it’s an at-fault divorce, so he’s getting bupkis from me. I get the house but between the mortgage and the taxes…” She sighed. “It’d be tight to keep it. It might be better to sell.”
I wasn’t in a position to give advice, but I felt I had to say something. “I’d hate to lose you guys as neighbors.”
“Well, you’re losing Tim. So get your goodbyes in if you want to.” Amanda said, staring at the water. She shifted from her seat and sat at the edge of the pool with her back to me as I sat at her eight o’clock. “Penny and I will stick around for a while, I think. Rent is crazy right now, and the prices for everything… plus my sister is talking about moving across the country, so if that happens, I’ll be stuck in that house forever.”
I nodded, realizing she couldn’t see me as she watched the ripples her legs made in the pool. She kicked them lazily, giving her body some motion to vent her frustration. I couldn’t imagine finding out my spouse was cheating on me.
“Are you okay?” I asked. “Not like… financially. I mean emotionally.”
“When Charlie died, and I brought over all those casseroles, every time I dropped one off, I asked you if you were okay. Do you remember what you answered?” Amanda asked.
I smiled slightly. I remembered being bombarded by the question after Charlie died and hating every inquiry. The answer was obvious, yet too many people asked. I knew why. They hoped I was okay. They wanted me to be okay. The question was their flawed expression of that. On the receiving end, it sucked. It was a constant prod and reminder that I wasn’t okay and didn’t know when I would be again. But it wasn’t polite to say, ‘fuck off, no, I’m not,’ so I had to answer something along the lines of ‘Yeah, I’m doing the best I can’ or some similar lie.
Until poor Amanda Rogers showed up at my door weeks after the funeral with another mac and cheese casserole in hand. She’d seen my frazzled state with food stains on my shirt and a screaming toddler in my arms, chuckled, and asked me if I was okay. Was I okay on a day when Abby wouldn’t stop crying and begging for her mother? To my shame, I lost my temper. Amanda hadn’t held it against me. She let herself inside and got Abby to settle so I could heat up and eat dinner.
“Yeah.” I answered. “I remember.”
Amanda looked over her shoulder at me and smiled a soft, tender smile. “I’ve had a few months to adjust to the idea of my ex-husband being a cheating asshole, but it still hurts.” She said. “It makes me feel like shit.”
I frowned. Not sure what I could do or say to help.
“I shouldn’t order pizza.” She said. “I should eat a salad or something.”
I laughed.
Amanda looked hurt by the laughter.
“Maybe if you eat a pizza every day for the next six months, you might start to look bad, but having a few slices tonight isn’t going to make you unattractive to anybody.” The very idea seemed silly to me. Amanda Rogers was a very attractive woman, not just for someone her age, but period. Granted, she was older and a mother, but she wasn’t gross, obese, or even unkempt. Her makeup was always spot on, and she dressed professionally for her job. Even her casual wear, the cover wrap she wore right now, looked attractive. It hung loose and baggy on her, revealing patches of lightly tanned skin on her arms, legs, and shoulders.
“You said Tim cheated?” I asked.
She nodded.
“I think that has more to do with Tim than with you.” I assured her. “Whoever he cheated with, I don’t think he cheated because he found you unattractive.”
“Do you find me attractive?” She asked, not looking at me but looking at her knees in the water.
“Of course.” I answered right away. “I almost took Tim up on that swinging offer, which I now realize might have been a red flag.”
Amanda laughed. “He never could keep his eyes to himself, that’s for sure. But I never thought he’d go further than that.”
I nodded, thinking back on when Tim had commented about my wife, actresses, women in general, or even some of Penny’s friends. I frowned. Now that I thought about it, he reminded me a lot of Bill from work, and the comparison soured my opinion of Tim.
“Thanks.” She said. “You okay if I get that pizza delivered here?”
I nodded. “Go for it. If you put ‘back door’ in the instructions, they’ll usually bring it around, and we can see them from the pool.”
“Thanks.” Amanda said. She stood up and retrieved her phone, dripping water from the pool as it slid along her thighs and calves to the poolside stones. She picked her phone off the chair, put in the order, and then shed her swimsuit cover.
Beneath the wrap was a red swimsuit that surprised me with its cut. The backless suit was tied in a knot behind her neck with a halter-style top. She turned to walk backward to the pool, showing me the deep V-neck in the front and the high curve of the bottom over her thighs and hips. I missed the view of her large butt and a quarter of each cheek peeking out from beneath it, but the view from the front wasn’t bad either.
I raised my eyebrows, showing my surprise, which made Amanda laugh.
“Care to join me for a swim?” She asked, dipping her toe into the water again by pointing her foot and bending one leg, stirring the water.
“Uh…” I glanced at my beer. How many had I had? I was getting that feeling again as if this wasn’t happening. “Just let me get my suit.”
“Oh, I don’t mind if you skinny dip. It’s your pool.” Amanda smiled.
I stuttered something in response, and she laughed, shooing me toward the house. I laughed with her and headed inside. Was… Was Penny’s mom coming onto me? Was she really divorced? Had I been that self-absorbed, I wouldn’t have noticed the signs of her and Tim’s marriage falling apart? Why hadn’t Penny told me? Maybe she didn’t want to think about it while she was over here? But still…
I went to my room and changed into my swim trunks. By the time I returned to the pool, Amanda was swimming in slow laps, face down in the water as she swam. I dipped my toe in, enjoying the refreshingly cool water in the summer dusk.
“Not going to take me up on skinny dipping, eh?” Amanda asked. “Pity.” She pouted as she trod water in the deep end.
“I’m not in college anymore.” I laughed. “My skinny dipping days are over.”
Amanda smiled. “I’ll do it if you will.”
I hesitated. Was Amanda Rogers coming onto me? I checked for the cameras, but there were none. Did Penny put her up to this? No. There was no way. Penny had been adamant her parents not know about us, a stipulation I fully endorsed. Tim would kill me. Amanda would kill me. There was no way she’d be coming onto me if she knew I’d… oh god. I’d fucked her daughter.
“I don’t think that’s a good idea.” I said, sitting on the edge of the pool.
“Tim won’t be upset.” Amanda said. Her eyes dipped to the hickey on my chest, indistinguishable from a bruise. She lifted her eyes to mine again with a shrug. “Or he might be, but A, he doesn’t have to know, and B, he has no right to be upset after what I’ve seen him doing in certain photographs with someone twice his age.”
That last bit took me by surprise. Twice Tim’s age? So… a hundred? Were granny kinks a thing? Oh god. Ew. I tried not to judge people beyond, y’know, the regular judgment someone deserved for cheating on their spouse. That crossed the line. I shook my head as if trying to dislodge the image from my mind or water from my ear, and Amanda laughed.
“Yeah.” She said. “But you didn’t hear it from me…” She glanced around. “So…”
I slipped into the water, and Amanda frowned but splashed me a second later, giggling as she did it.
I laughed as well and sent a wave in her direction. We swam a few strokes, and I felt my old bones remember their familiar movements in the water, relaxing me and making the time enjoyable as Amanda and I caught up on the drudgery of life and work.
“So… my daughter tells me you’re dating again?” Amanda asked as if bringing the subject matter up casually. “She mentioned helping you with your Tinder profile because you’re hopeless with technology?”
I laughed. “Yeah, I guess my ‘Kiss the Cook’ apron profile photo wasn’t too impressive.” I blushed at the memory of Penny taking the photos to help my profile and our first intimate time together. A time her mother could never learn about.
“You’ll have to give me some tips on how to snag the hotties.” She said, swimming closer to me.
“I think we fish in different pools.” I said, and she laughed. “But you’ll do just fine. A casual picture of you in your regular clothes, maybe one in that swimsuit? You’ll have guys lined up around the block to marry you.”
She laughed again, this time derisive and churlish. “Spare me. I have no desire to get married again.” She shook her head. “I want some of that casual sex Penny and her friends talk about. My Samantha era.”
“Samantha?” I asked.
“Sex and the City.” Amanda answered. “Don’t judge me.”
I laughed. “I’m not judging. Charlie used to love that show.”
“I know we–” Amanda cut herself off. “Sorry.”
“It’s okay.” I said. “You can talk about her. Sometimes it’s good to remember the fun and good stuff.”
Amanda smiled. “Fun and good stuff. That’s what I want now that I’m free.”
I nodded. “Makes sense. Go crazy. Hit up the apps and meet some guys. Form a harem of men you can call up for sex any day of the week.”
“Ooh, I like the way you think.” Amanda smiled. “How do Saturdays work for you?”
I laughed and shook my head.
Her bold smile faded at my rejection. She took my head shake for a no, and the brash and confident facade before me shattered into a frail, vulnerable, and embarrassed woman. “I’m sorry. I shouldn’t have said that. I… you don’t have to respond to that. I just… um… I’m gonna get a drink. Do you want a drink?”
“Drinks sound good.” I agreed. “I have some wine?”
“Maybe something stronger.” Amanda said. “I really am sorry. I–”
“Amanda, it’s okay.” I said. “I’m sorry. You surprised me, is all. I wasn’t thinking of you like that.”
“Well… why the fuck not?” Amanda asked. “You said I’m attractive, right?”
I hesitated in my swim toward the pool’s edge. Would praying for someone to appear and save me from this situation be unkind? Probably. I prayed for it anyway.
“Or was that just to make me feel better?” Amanda asked, her voice brittle.
“You’re very–”
“Don’t answer!” Amanda said. “I’m sorry. I shouldn’t have asked you that. Just… go get the drinks. I’m going to swim to the bottom and stay there until the embarrassment fades.”
I laughed, trying to lighten the conversation, but it seemed like I was laughing at her, so I stopped as I pulled myself out of the water. “I’ll be right back with some drinks.”
I glanced behind me to see her swimming to the edge of the pool. Confident she wouldn’t drown from embarrassment, I padded to my bar and poured two whiskeys, each with an ice cube. I knew how she took hers after years of parties serving each other drinks. With the drinks in hand, I returned to see her drying off at lightning speed, her things gathered and bundled.
“Shit.” She said, straightening. She covered herself with the towel as I approached, hiding behind it like a blanket.
“Amanda.” I said. “You don’t have to be embarrassed. It’s perfectly natural to wonder how attractive someone of the other gender finds you. I just… you took me by surprise. I wasn’t expecting it.”
Amanda nodded. “I’m sorry.” She said. “I wasn’t trying to blindside you, honest. I thought Penny would have told you about the divorce by now, or Tim might have mentioned it, and I figured… if you’re dating again, and I’m dating again, maybe you’d be down for… oh-my-god-nevermind-it-was-a-dumb-idea.” She took the whiskey from me like a cobra darting from its hole and drank it in a gulp.
“Feel better?” I asked.
“Not really.” She said, her voice strained with the strangling tingle of the whiskey, which made her cough and both of us laugh. “Wow. That was the good stuff.”
“Nothing but the best for a celebration.” I said.
“What are we celebrating?” She asked, still laughing at her inhaling the whiskey and coughing to clear her throat.
“Your newfound sexual liberty? May you have many hot nights ahead of you.” I raised my glass to her, toasting.
She rallied at my toast and clinked her empty glass against my full one. I drank as she pretended to. Her smile as I killed my glass couldn’t stretch any wider. She killed hers afterward.
“Maybe I’ll fetch the bottle.” I said, smiling.
“Okay.” She said, offering me her glass. I gestured for her to keep it and set mine beside it on the small table. She watched me re-enter the house. I saw her preening from the kitchen as she fixed her chlorine-flattened hair. She perched on the lounge chair by the pool with a stature that made her seem bold and brazen. She carefully pinned her confident facade into place again, and I told myself I’d do as little as possible to disturb it while turning her down gently.
Not that she was following through with any of her flirtations, but… that couldn’t happen. I could not fuck Amanda Rogers, but worse than that, I couldn’t tell her the real reason why.
I wish I hadn’t left my phone by the pool, but it didn’t matter. Amanda wasn’t perching on the lounge chair when I returned from the house. For a moment, I’d thought she’d followed through and fled to her house, but no. She was at the gate, carrying a pizza box with a broad smile.
“I flashed the delivery guy!” She said, as if proud of herself.
I laughed. “Did he thank you for the tip?”
She smiled. “He blushed, said ‘thank you, ma’am,’ and walked away, but I did it! And he liked what he saw!”
“He must have other deliveries to make.” I said. I wondered how she knew he liked what he saw, but I realized any man’s appreciation for titty was easy to see. If not in their expression, then in their trousers.
Amanda set the pizza box on the picnic table by the grill and offered me a slice. I agreed and grabbed some paper plates from the kitchen. She dished out the pizza and handed me my slice.
“I know they say no swimming for half an hour after eating, but what about the hot tub?” Amanda asked.
“We can eat in the hot tub.” I said, shrugging.
“Perfect.” She led the way, putting extra sway into her hips that I did my best not to notice. “Bring the whiskey bottle.”
I suddenly wondered if that was a good idea, but I brought it. I plodded to the hot tub, raised slightly and overlooking the adjacent pool with its spillover feature. The water was true to its descriptive name, and I set the bubbles to start as we put our plates on the stone behind us and relaxed across from one another.
“Oh, this is nice.” Amanda said. “I always wanted a pool and a hot tub.”
“It’s a lot of maintenance and a lot of money.” I said. “But yeah… worth it if you use it. Or if you can share it with people who will.”
Amanda smiled, closing her eyes and releasing an exhale so long I didn’t realize she had it in her.
I followed her example and relaxed, letting the hot water and massage jets soothe away any anxiety trying to gnaw at my brain. This was Penny’s mother. I shouldn’t be sitting in the hot tub alone, with pizza and whiskey, with the mother of a nineteen-year-old girl I had sexual relations with as recently as that morning.
“Penny is out with friends, you said?” I asked, my mind thinking of her and my lips asking the question before I could stop them.
“Mmhmm.” Her mom said. “She’s sleeping over at a friend’s house, Rowan, I think the name was. They were going to a concert or show or something in the city.”
“Sounds like a date.” I said, laughing to hide my annoyance. I had no right to be annoyed. I knew that. But whoever this Rowan jerk was, I wanted to punch him in the face.
Her mother laughed. “I don’t think Rowan’s her type, but who knows? There are no rules when it comes to sex.”
“Aren’t there?” I asked, still annoyed and doing my darndest to not show it. I was so confused about where Penny and I stood with each other, and every word out of her mother’s mouth only made me more uncertain.
“Consent. That’s the only rule.” Amanda said, shrugging. “Whatever two consenting adults do together is between them, God, and the hot tub.”
“Heh. Yeah, I guess.” I said, not thinking too hard about what she said until my brain caught up to the third witness on her list. My eyes flared open, and I looked at her. She grinned like the cat who ate the canary.
“So…” She said, scooting over to sit beside me rather than across from me. “Let’s play a game.”
“A game?” I asked, swallowing my fear, which must have come across as nervousness.
“Have you ever played, never have I ever?” She asked.
I laughed. “Never have I ever played, never have I ever. Do I win?”
Amanda laughed, pushing my shoulder with her palm. “Come on, Julio. Let’s play a game or something.”
She uncapped the whiskey. “Whoever’s done the thing takes a sip.”
I glanced at the bottle. It was an expensive one, and I was really more of a beer guy, but… maybe I’d get lucky; she’d pass out, and I could carry her home, put her to bed, and escape while being able to look both her and Penny in the eyes tomorrow morning.
“Okay.” I said. “Never have I ever played, never have I ever.”
Amanda laughed and took a small sip from the bottle. She hadn’t even tried her pizza yet. I took a bite of my slice, enjoying the pull of the cheese as she thought up her turn.
“Never have I ever had sex in a hot tub.”
She shouted in victory as I took the bottle and took a swig. I wasn’t worried about germs from her lips being on it a second ago. The alcohol was certainly strong enough.
“Tell the story!” She insisted.
I shook my head. “Me and Charlie, nothing very storied about it… just… y’know. Hanging out, making out, leading to more.”
Amanda giggled. “So hot.” She fanned herself. “I always wanted to have sex in a hot tub.”
“Well, if you want to borrow for one of your dates, you can. Just clean it after.” I joked, and Amanda gave me a devilish smirk as she took the bottle from me. “But fair warning, underwater sex isn't great. By the hot tub is better than in it.”
“Good to know.” Amanda said.
“Never have I ever–” I started.
“Wait!” Amanda interrupted. “I have a better idea. Let’s play Would You Rather.”
“I… don’t know that one.” I answered honestly.
“Would you rather be tickled or edged?” Amanda asked as if it were the most normal question in the world.
“Uh…” I hesitated. “What’s edged?”
“Being aroused, teased, and pleasured but not allowed to cum.” Amanda explained, the blush in her face matching my own.
“Tickled.” I said immediately.
Amanda laughed. “Me too.”
“So… how does that lead to one of us drinking?” I asked.
Amanda took a sip from the bottle. “It doesn’t. We just drink.” She passed the bottle to me.
“Oh.” I said, taking a swig for courage. “Okay… would you rather kiss the pizza delivery guy or the Chinese food delivery guy?”
“Pizza delivery guy. He has a mustache.” Amanda answered without missing a beat.
“You like guys with mustaches?” I asked, hopeful because I was clean-shaven. Not that she wasn’t attractive, but because I was continually looking for a way to end this night without hurting her feelings or hurting Penny in some unforgivable sin. Even if she was out cajoling with some asshole named Rowan.
“No, but I’ve always been curious.” She said, reaching for the bottle. She took a swig and then asked her question. “Would you rather fuck me or Tim?”
I laughed. “You.” I said without hesitation. “Tim’s too old for me.”
Amanda laughed at that. “Me too, honestly. I think I’m into younger guys… how old are you again?”
“Thirty-nine.” I answered.
“Yeah, I’m into younger guys.” Amanda took another swig and then passed me the bottle.
I laughed. “I’m still not sure I understand this game. How do we know who wins?”
“Oh, trust me, you’ll know.” Amanda said, smiling. “Now, ask me the question.”
“Uh…” I hesitated, not sure what to ask. “Would you rather have a one-night stand or a long, meaningful relationship?”
“Pfft.” Amanda answered as I took a drink from the bottle. “One-night stand. Especially if it’s a guy who’s nice, sexy, clean, respectable, treats a woman right, and lives close enough to answer the latest of late-night booty calls.”
“You wouldn’t worry about sex ruining the friendship?” I asked, surprised.
“Do sprinkles ruin ice cream?” She asked as if the suggestion were absurd. “That’s why it has to be a friend you trust, obviously, and if they break that trust, well, that’s okay because they were just a friend anyway. It’s not like you married them, and then they ditched you!”
I frowned at that, but Amanda was too free to notice. She took another sip from the bottle and set it aside as she knelt on the bench and leaned closer to me. “Would you rather streak naked around the block or skinny dip with me?”
“Uh… skinny dip with you.” I answered, deciding I didn’t like the idea of anyone seeing me naked who wasn’t already planning to do so. Somehow, I got the feeling that Amanda was planning to see me naked either way.
“Then take off those trunks, Julio.” Amanda said.
“I…” I hesitated and tried to stall for a while.
“Here.” She said. “I’ll give you some encouragement.” She crossed her hands behind her head. I thought she was fixing her hair, but no. She rose out of the water slightly, revealing the press of her breasts in her skin-tight swimsuit with its deep v-neck several inches below the start of her breasts. She unfastened the knot behind her neck and let the suit fall, peeling it to just above her nipples where her hands clamped over her breasts to preserve her modesty.
“Would you rather see the left one or the right one?”
“Uh…” Fuck. I should stop this. I knew that much. I should get out and leave her here, but if I did that, it would not only hurt her, but it would also end our friendship. She didn’t deserve that, at least not without knowing why. “Amanda…”
“Mandy.” She corrected me. “Call me Mandy from now, okay?”
“Okay.” I said, confused by the non-sequitur.
“Only my work friends, teachers, or people I don’t know call me Amanda.” She said. “My friends call me Mandy. Especially those who’ve seen me naked.”
“But I haven’t–”
She pulled both straps down, revealing her breasts and raising them in her hands to me as if presenting them. My dick responded on its own, standing at attention to the sight of two groped, tear-shaped breasts moving toward me until the hardened nipple pressed against my lips, which worked to suckle at her breast as if remembering their ancient purpose.
“Oh, there you go.” She said, gasping as she straddled my lap. Her crotch stroked the underside of my cock, and I gulped, sucking on her nipple in my mouth as I did so. She ran her fingers through my hair, scraping my scalp. “Oh, Julio.” She panted. “Yes.”
She sounded as though she were in the midst of pornographic ecstasy, but we’d barely touched. I had some reason to think I was a decent lay, but I knew I wasn't good enough to make her moan like that just by having an erection she could grind on.
“It’s been years since I’ve felt a cock between my legs, Julio.” Mandy panted. “Come on.” She gripped the waistband of my shorts and lowered them over my hips. “Do a girl a favor and be the man I need, even if it's just for tonight.”
I gasped as she reached into shorts. I released her breast from my mouth and tried to speak. “Mandy, we shouldn’t!”
“Yes, we should.” Mandy said. “Come on, Julio. I’ve seen the way you look at me. Don’t deny it. Or better yet, tell me it’s all in my head. Tell me you don’t want me, and I’ll go.” Her eyes met mine, daring me to say it. I could see the water behind them. She was ready to cry if I said no. “No? Then shut up and kiss me.”
She was straddling me on the bench, her knees on either side of my legs, her suit lowered to her hips, floating between us. My suit encircled my thighs, revealing my cock to the water where her hand pumped my length toward her with her fingers curled around my shaft. I closed my eyes, trying to shut out the image so I could gather the strength to tell her to stop. I wanted this, to my shame, but I had to stop her, or we’d cross a line I could never uncross.
Her lips crashed into mine, and her tongue pushed into my mouth with a hungry force I couldn’t resist. I melted into her clawing embrace and returned the kiss, my tongue wrestling hers as she roughly gripped my scalp and took fistfuls of my hair. I ground upwards, sliding my cock against her.
She moaned into the kiss and ground against me. If we’d been on the lounge chairs with her natural lubrication spreading between her folds, I might have pushed in, but in the hot tub, her natural barriers deflected my length, turning the penetration into a grind. We weren't fucking so much as humping like teenagers, but from the noises she made, it was tough to tell the difference.
Amanda bit my lip, tugging on it. “Fuck me, Julio.” She panted into my ear. “Right here, and right now, like you goddamn mean it.”
I wanted to. I desperately wanted to. “Amanda…”
“Mandy.” She snapped.
“Mandy…” I tried again, but my protest came out a moan. “I want you to–”
She’d heard ‘I want you’ and silenced me with a kiss.
After that, she took over. She pulled me to my feet and spun me around. She kicked off her suit, sat on the edge, and rested on the concrete. She pulled me onto the bench by my hips and spread her legs for me.
I sank into her with a single push. She curled up and exhaled a ragged breath as I entered her, pushing inside her with no effort on my part. She was hotter than the tub and wetter inside. She groaned, straining, gripping my forearms and tensing as though the pleasure were overwhelming her.
“FUUUUUUUUCCCK!” She bellowed her pleasure to the sky in a long, low moan. “Oh, fuck me.” She panted, echoing herself.
I moved my hands to her hips and gave in. I fucked her. Moving my hips in time with her as she rolled her hips against me, throwing her entire body into the effort. I groped her breasts, one in each hand, and sucked on her nipple as we fucked. She moaned and did her best to breathe without summoning our other neighbors.
“Oh, god, I’m going to–” She cut herself off as she reached between us and rubbed herself, drawing out her orgasm with an intensity I felt flutter then grind against me within her.
She must have been primed and ready. I didn’t know when she’d last had sex, but if what she said about Tim was true, it might’ve been longer for her than for me.
Her orgasm rolled into the next one, and another as she rubbed her clit and spasmed against my cock. I gasped, and my balls emptied into her, pumping blow after blow into her. I went still as I fired off, and she slowed, then stopped as I did.
I stood there, looking down at her with my hands on her thighs.
She looked at me with her eyes shining. Her wet hair splayed behind her like a halo. “Oh, fuck, Julio. That was amazing.”
I caught my breath. “Yeah. You were… that was…” I couldn’t get the words out.
She smiled at me, impressed with herself, and genuinely happy in a way that broke my heart.
I staggered back, and stepped out of the hot tub to sit on its edge with my feet in the warm water.
“Be right back.” Amanda said as she withdrew from the tub. She grabbed her swimsuit and held it to her chest as she ran inside the house. She had scratches on her back from the rough concrete, but nothing that broke the skin.
I stared after her, watching the sliding glass door close before I collapsed in my seat. I let my head fall back and stared at the sky.
“Oh, fuck.” I groaned. “Oh, fuck.”
I just fucked Penny's Mom. Fuck.
Comments
I’m loving this series. Can’t wait to see what happens net
Ben J
2025-01-20 15:33:28 +0000 UTC