Loving My Slutty Babysitter
By: Date: 2021.05.23. Categories: Sex Stories Tags: , , , ,

I don’t know how I ended up so lucky. Normally, I’m the most unfortunate son of a bitch you’d ever meet.

“Hey, how’s Eleanor?” I asked, coming in to find two people sitting in the living room of sardine can sized apartment, not including my daughter.

“She’s fine,” said Natalie, my babysitter. “We had boatloads of fun, didn’t we, sweetie?”

As Eleanor laughed, Natalie flashed her sparkling and soulful eyes at me, making me almost melt on the spot. However, I quickly swallowed my attraction, as her big brother got up off the couch.

“We should get home.”

“Why?” Natalie asked him.

“It’s getting late.”

“We live across the hall, not across town.”

“I’m sure Eddie doesn’t want us here.”

“I don’t mind,” I told him, but that only seemed to make Oliver more frustrated.

“Stop hovering over me and go home. Please.”

It took another few moments, but Oliver finally went to the door, though he did stop to flash a look of warning in my direction.

“Do you have any older brothers?”

“One,” I told her. “Plus a younger sister.”

“They’re a pain, aren’t they?”

“Younger sisters? You bet.”

She flashed me the same dirty look her brother just had, down to a T.

As Eleanor began to yawn, Natalie picked her up and whisked her off to her bedroom.

When she came out, I was sitting on the couch with my laptop and a glass of red wine.

“Aren’t you going to sleep?” she asked me.

“I don’t sleep, much.”

She looked at me, confused.

“I have a shift tomorrow at noon. I might grab a few hours before then, but I’ve got a lot of stuff to finish.”

She leaned over the couch, and closed the lid of my computer.

“That’s not healthy.”

“Well, there’s not much I can do about it. I have one more month before I finish my master’s degree, so I can’t afford to stop now.”

“You already work super hard. You should take a break and be normal. Get drunk, go on vacation, get a hot date or do something exciting.”

“I never have time to do any of that. Between Eleanor, school and working full time-”

“But that will only last for another month. You’ll get a better paying job after that, right?”

“Hopefully. I did well at the job fair, I think.”

“You see? You should do exciting stuff now, so you’re in practice.”

“I should practice getting drunk?”

“Totally. I’ll help you get started.”

Without a word of warning, Natalie grabbed my wine glass and downed the whole thing in a few chugs.

“See? Now you try it.”

Though she handed the glass back to me, I quickly turned it over in front of her, wondering exactly what I was supposed to drink.

“Go open a new bottle. We can…” She suddenly trailed off, before getting very excited. “We can kill two birds with one stone.”


“You can open a bottle of wine, put on some fancy clothes and we can give you a practice date. Then, we’ll get completely hammered.”

“A practice date?”

“Yeah, for a month from now, when you’re rolling in bitches.”

I laughed. “Has anyone ever told you that you’re insane?”

“Every day in the mirror,” she said, with a wink and a nod. “Now, go put on your best suit and open your best bottle of wine. I expect to be swept off my feet.”

She was gone less than thirty seconds later, leaving me alone and confused.

If there is one thing I’ll say about Natalie, it’s that she moves fast, no matter what she’s doing. It is, by far, the most annoying and endearing thing about her.

Before I started setting up for my practice date, I stopped to check in on Eleanor, wanting to make sure she was ok, before I did anything else. She looked completely at peace, as she slept like… well, she slept like a baby.

However, something about me dating made me uncomfortable, as I looked down at her. For the last year, I’d had the excuse that school or work kept me too busy for other people, but now that I was about to have the time again, it suddenly frightened me.

I spent the next half hour preparing for Natalie’s arrival, with a lump the size of a baseball in my throat, and it only got larger when I heard a soft knocking on my door.

“I had to sneak past my brother,” she told me, as soon as I could see her, but I was too distracted to respond.

“You look…”

“Not bad, right?” she said, twirling her new dress. “I haven’t had a chance to wear this yet.”

“So you wore it for my practice date?”

“Life is short. Better to take the opportunity, than let it gather dust.”

The room seemed to grow brighter as she walked inside, her infectious smile quickly spreading over to me.

“You did better than I expected,” Natalie told me, as she looked down at my kitchen table, and the leftovers served on fancy platters.

“I didn’t have time to actually cook.”

“Well, meatloaf and mac’n’cheese can be romantic, if we try hard enough.”

“Romantic? I thought this was just a practice date?”

Now it was her turn to get red and flustered. “Sure it is. Of course.”

The two of us sat down at opposite ends of the table, scooping out lumps of cold pasta and lukewarm meatloaf onto our plates.

“Ok, first piece of advice; when you take a girl out to eat, hot food is a must.”

“I’ll keep that in mind, but here’s some advice for you,” I told her. “When you want a guy to impress you, give him more than thirty minutes notice.”

“A real gentleman could have made it work,” she said, picking up the bottle of wine from the center of the table. “Luckily, I don’t know anything about wine, so you should be able to impress me there.”

Even after all of her complaining, Natalie still spent half of our conversation shoveling mac’n’cheese into her mouth, like she hadn’t eaten in days. I didn’t mind, though. To be honest, it was nice being able to be myself around someone.

“You know, you’re always unapologetic about who you are,” I told her. “I respect that.”

“Tell that to Oliver.”

“What do you mean?”

She shrugged, suddenly looking sad. “I’m the shithead of the family. Unlike Oliver, I never went to college, and now I’m sleeping on his couch. That’s why he always looks down on me.”

“He doesn’t look down on you. He’s just protective.”

“Maybe, but it doesn’t feel that way.” She poured a glass of wine for herself, but it was gone in seconds. “I know that I’d be making more money if I had gone to college right away, just like I know there are a lot of decisions I could have made that would help me make more money and have a big house and a husband and ten babies and a church to attend every Sunday, but I don’t want that. I’m not going to school until I know what I want to do, and I’m not going to go unless I want to. I know it’ll hurt me, long term, but it’s my decision and I’ll face the consequences, not my mom, not my dad and certainly not Oliver.”


“Yeah,” she said, pouring two glasses and handing one to me. “Sorry, Eddie. That was a lot to dump on you.”

“No, it wasn’t. Like I said, I respect you for being yourself, warts and all,” I told her, as we clinked our glasses in a toast.

“So, what’s your baggage?”

“Excuse me?”

“What’s your baggage?” Natalie asked me, again. “Come on. I unloaded on you. Now, it’s your turn.”

“I don’t have any baggage.”

“You a single dad. You don’t sleep. You haven’t been on a date in years.”

“I know,” I said, before she could continue. “I have a lot of stuff to work through, but Eleanor comes first. I have to worry about her first.”

Natalie’s had slid across the table, resting on top of mine. “Eleanor is going to grow up to be smart and beautiful. You don’t have to worry about her.”

“It’s not that. I know she’ll be pretty. She’s my kid, after all.”

Natalie laughed. “You’re such a jackass.”

The two of us shared a chuckle, but when it was over I looked at Natalie and saw that look on her face that said she wasn’t going to let this subject go.

“It’s not something that I have to worry about now, but eventually Eleanor is going to ask where her mother is.”

“You never talk about her.”

“She took off a few months ago. Haven’t seen her since.” Natalie’s face suddenly softened, when she heard that. “One day, Eleanor is going to ask where her mother is, and the truth is, I have no goddamn idea how I’m going to explain it to her.”

“Be honest?”

“She’ll be crushed. I can’t tell my daughter that her own mother didn’t want to be in her life.”

“You don’t have to phrase it like that, but you have to be honest. It’ll hurt, but she deserves to know the truth.”

“That’s what you think. I won’t make her live like that, knowing that she was tossed aside, that her mother didn’t want her.”


“I’m not making her live with that knowledge, dealing with the stomach aches, the pain and the insomnia, as she wonders if her mother is ever coming back.”

The whole room fell eerily silent, as I realized what I had just said.

“Are you still waiting for her?” Natalie asked me.

I didn’t know what to say. I hadn’t expected to suddenly make such an ass of myself.

“I don’t really know,” I said, honestly. “I have a lot of emotions swirling around, but the logical part of me knows that I could never go back to her. She’s too good at causing pain, for that to ever work.”

I looked down at the table, unable to look at Natalie as I spoke, but I was so distracted by my shame that I didn’t notice her coming towards me, and was caught off guard when she lifted my head and suddenly put her lips against mine.

“Fuck,” I said, “After all of this, I’m starting to wonder when this will turn into a real date.”

She smiled. “When you fuck me.”

My emotions certainly didn’t swirl any less, after that, but as she came back for another kiss, I was suddenly hit with a sense of clarity.

My shirt was off in seconds, but it hit the floor only moments before my belt.

As my hands roamed down her back and to her hips, Natalie kissed her way down to my neck, leaving a trail of lipstick down my cheek.

“We have to be quiet,” I told her.

Her only response was to giggle and say, “You should be more worried about yourself.”

It only took one quick pull for her to tear off my pants and boxers, and my cock was standing at full attention. Natalie kissed along the length of my shaft, all the way to the tip.

“Oh, fuck,” I said, moaning in pleasure, before gently placing my head into her open and waiting mouth.

I could feel her humming softly, as her tongue teased the tip of my cock.

“How am I doing?” she asked, pulling away.


I nearly cried out, as she once again wrapped her lips around my engorged staff, but I knew I had to keep quiet.

However, Natalie’s words were turning out to be true, and I was having considerable trouble keeping my voice down, especially once I felt myself building up to a climax.

“Stop, for a second.”

“Did I do something wrong?”

‘Fuck, no,” I told her, vehemently. “I just don’t want to finish too early.”

“Oh, good. I was worried, because that’s the first time I’ve done that.”

I looked down at her, completely in shock. “Really?”

“Yeah. I mean, I’ve done other stuff, but I’ve just never had a guy ask for that, before.”

I pulled her up to her feet, holding her tightly sculpted body next to mine.

“So, it was good, right?”

I laughed and prepared to tell her that it was, for the third time, but suddenly stopped when a thought crossed my mind.

“Is this what it feels like, when you say I worry too much?”


I leaned in, enjoying the fact that this time I got to take the lead.

In between breaths she managed to sputter out, “Do you want to move to-” but suddenly gasped, as I lifted her into my arms.

She was lighter than I expected, and felt so small as she wrapped her arms around me and nibbled on my earlobe. All the while, I carried her off to my bedroom, creeping past Eleanor’s room at a snail’s pace.

However, knowing that I needed to be quiet only turned Natalie on more, and she redoubled her efforts to get me to cry out, at the worst fucking time.

“You drive me crazy.”

“That’s the idea,” she said, making me nearly fall over as she slid one finger down the full length of my cock.

Moments later, we made it into the bedroom, and I breathed a sigh of relief that Eleanor hadn’t woken up.

I gently closed the door behind me, after letting her down. I considered telling her how irresponsible she was and scolding her for almost waking up my daughter, but as I saw her dress slip from her shoulders, all of that disappeared.

“You didn’t wear underwear to a practice date?” I said.

She strode over to me, placing one of my hands over her breast as she told me, “I also made sure to grab some plan B. I was being hopeful.”

I fell down onto the bed, with my sexy little babysitter on top of me. I think you know this part of the story already, and the really exciting part comes next, after

I’ve pinned her down.

“Oh, fuck,” she whispered, as Natalie fully internalized what was about to happen.

“I guess this isn’t a practice date anymore.”

“You’re not inside me, yet.”

As I kissed my young lover, once again, my head began to gently push past her folds. Her slick cunt put up not resistance, except for how naturally tight it was.

“Sorry I’m so-”

“You’ve got nothing to apologize for,” I told her, continuing to gently open her up, putting myself further and further inside of her.

Natalie moaned, as she kissed me, softly, and wrapped her legs and arms around my body. “I’m not used to being with someone who is so gentle. Most boys my age just want to get inside as quickly as they can.”

“Well, I love seeing you quiver every time I push inside you.”

“And making me wet?”

“Of course?”

“Well, I’m plenty wet, now. I’m ready for you.”

I didn’t need one more word of convincing.

“Oh-” She cried out, before remembering she had to stay quiet. Natalie furiously bit her bottom lip, barely able to contain her screams of pleasure, as I unleashed my full force inside of her.

In an instant, her velvet folds went from being gently opened, to forcibly gaping, as my stone member fucked her tight hole, over and over and over.

“Fuck. Fuck. Fuck,” she whispered, wracked with pleasure.

“You like it?”

“You know I do.”

She wrapped around me in just the right way, her pussy being so tight that it came close to hurting, as my cock penetrated her.

Meanwhile, she ended her frantic whispering and began kissing along my neck, once again, only this time purposefully leaving a trail of hickeys across my skin.

“You can’t leave evidence.” I stopping for a moment, so that I could remind her of who lived across the hall. “Won’t your brother be mad if he finds out?”

“Of course he will,” she said, pulling me back down, fully inside of her, and starting our rhythm, once again.

“Fuck, you’re getting me close,” she said, almost completely breathless.

“So, am I. You’re too tight to resist.”

She quickly left another hickey near my shoulder, but I could feel her bite down as her skin was in my mouth.

“What the hell?”

“Sorry, that was just…” Her eyes rolled back as the feeling continued to sweep through her. “That was a lot more than I expected. Are you ready?”

“Ready for what?”

I could feel her hands moving across my skin, as I kept fucking her amazingly wet cunt. “I want you to cum inside me.”

“You do?” I asked, wondering if she knew how hot that sounded, to me.

“I do. I want to feel you pouring out, as deep as you can. I need-”

I didn’t wait for one more word. I rose up off the bed, seized her by the hips and ravaged her pussy, forcing her cunt further apart and putting my cock deeper than it had ever been.

Somehow, through it all, she remained silent, clutching the sheets as she writhed in pleasure, before I finally climaxed in just the way she wanted.

Drops of cum ran down her stomach, forced out of her overflowing pussy, as I shot load after load of my sticky cum into the babysitter, and as the feeling of receiving my seed hit her, Natalie finally cracked.


Once her call had wrung out, the two of us sat there for several moments, waiting for the crying to start, but it never did.

“You got so goddamn lucky.”

She smiled and looked down at her cum covered pussy lips and my limp cock draped over her stomach. “Yeah, I did.”

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