I’m gonna edit this to get around the post size limit
Like the title suggests, this story starts with me getting hired as a babysitter. After graduating high school my family didn’t have enough money for college so I ended up working in customer service, and I babysat occasionally for a little extra cash. The kids I was babysitting in this case were 4, 8, and 13, but they also had an older sister who was a high school senior (18F), I’ll call her Maisie.
. I arrived at 5:00 and the parents said they’d be back around midnight and left, telling me that the kids’ bedtimes were 7, 9, and 10 in ascending order of age, and dinner was usually around 5:30, they told me to order a pizza, and that they had an indoor pool in case any of the kids wanted to go swimming while I was there. I brought a swimsuit in case the kids did decide to swim.
It started off like any normal babysitting, I let the kids watch television while I relaxed on the couch and Maisie stayed in her room studying. Eventually it got to 5:30 so I ordered a pizza and let Maisie and the kids know it was dinner time. When Maisie arrived everyone else had already started eating, but the moment she walked into the room she caught my eye. She was wearing a hoodie and a pair of short shorts that instantly drew my attention. When her back was turned to serve herself pizza from the counter I couldn’t help but take a good long look at her gorgeous ass. It wasn’t huge, but it had a perfect roundness to it that made me want to slap it and squeeze it as hard as I could, and I was sure that it would look even better with the shorts off. She turned back around to come over to the table and I quickly averted my eyes back to my food, but I think she caught me staring because she shot me a knowing smile.
When she got to the table she said “it’s hot in here, isn’t it?”, and took off her hoodie to reveal a light pink tank top. The spaghetti straps did their job of fastening the garment and preventing it from falling off, but there was a slight looseness to them, as if they were begging me to walk over, slip them over her shoulders, and take off the tank top. And the way the tank top hugged her boobs — which, like her ass, were small but perfectly formed — to her chest was enough to almost fully entrance me as we ate.
We finished at the same time, but I waited to take my plate up to the sink so I could watch her ass sway from side to side as she walked. Once she reached the sink, I stood up and began walking over, passing her on the way. As I walked by, my hand “accidentally” touched her thigh. She let out a barely audible gasp of surprise, but continued back to her room as I put my plate in the sink, grinning from the brief touch I had managed to get but wishing for more.
Later in the night, once all the kids were in bed, I sat down on the couch, tired from babysitting them for the evening. I briefly considered going into Maisie’s room but wasn’t sure what kind of reaction that would get from her, or if she would have her parents fire me which would result in me never getting to feast my eyes on her again, so I decided against it. Before long, I had fallen asleep on the couch, but I was soon woken up by the sound of footsteps.
It took me a minute to get my bearings but when I did, I heard a door close. The door to Maisie’s room was wide open and the light in it was off, so I deduced that it must be her whose footsteps had woken me up. I quietly walked over to see what she was doing, and discovered that she had gone into the room that I had been told contained the indoor pool. I listened at the door, and heard splashes that indicated she was swimming. I waited for the splashes to become particularly loud, and slowly pushed the door open just enough for me to poke my head through. I did, and what I saw next caused my mouth to hang open in shock.
There was Maisie, stark naked, swimming laps in the indoor pool.
I saw that the clothes she had been wearing earlier, as well as underclothes, had been placed next to the pool. After a good ten minutes or so of watching this take place, I decided that I needed to get a better view, maybe even more than just a view, so I formulated a plan. I put on the bathing suit I had brought, and strolled right into the room with the pool, feigning a look of surprise as I noticed her in the pool while inwardly admiring her flawless body. She looked up at me and gasped, much like the gasp from when I had touched her thigh only louder, more provocative.
“Oh, I didn’t know you were in here,” I lied, approaching the pool. She hastily tried to clamber out, but in her rush she accidentally fell back into the pool, giving me a full view of her tits and pussy. They. Were. Beautiful. Her pussy looked to be just the perfect size for me to finger and get my dick inside, and the qualities that her boobs had possessed while she was wearing the tank top were only amplified now that it was gone, especially as they bounced up and down as she fell into the water. I walked over to the side of the pool as she came back up to the surface, extending a hand to help her out.
Reluctantly, she took it, and I enjoyed the closeness of our bodies as she stood up once she was out of the pool. She seemed embarrassed, and tried to cover up her boobs, ass, and pussy so I wouldn’t be able to see them — a task that proved impossible since she only had two hands to do it with, and in a way, her trying and failing to cover herself up was almost even better than if she had proudly displayed her body to me. “What’s wrong?” I asked her, “no one’s ever seen you naked?”
She shook her head, her gaze pointing down at the ground in shame. “N-not a man.”
I reached out a hand slowly toward her boobs, raising an eyebrow at her as if to ask whether she wanted me to touch her. After a long pause, she nodded shyly, a slight smile tugging at the corner of her lips. I brought out my left hand to go with my right, and as they made contact with her boobs, she gasped again. I squeezed, starting with a light grip then working my way up to clenching my grip on her boobs as hard as I could, feeling my dick grow in my swim shorts. Her gasp turned into a moan, and only now did she look back up at me, our eyes meeting as I squeezed relentlessly. I could tell she was enjoying this just as much as I was, but her eyes seemed pleading, as if she was in pain but enjoying every minute of it.
Eventually, I decided she had had enough of that, and I altered my grip so that while I was still holding onto her boobs, the tips of them including her tits were exposed. I then tightened my grip once again and began shaking her boobs, watching them bounce up and down as she moaned even more. I smiled, bringing my head in closer and burying it in between her boobs as I continued to squeeze, shake, and rub them raw, with her moaning loudly all the while.
After a while of that, I decided it was time to move a little lower. I slowly eased her to the ground, and her body was splayed out before me. The feeling of *power* I had over her in that moment was indescribable. I could do whatever I wanted to her and she would have no way of stopping me.
“Can I touch you?” I asked, already knowing the answer.
“Yes,” she breathed, clearly eager for me to resume.
“As much as I want?”
“Yes!”
“Wherever I want?”
“Yes!”
I could tell she was *longing* for more at this point, so I gave her what she wanted. After a few minutes of just looking at her naked body licking my lips and enjoying the feeling of total control I had over her, I moved in. I started with her boobs again, poking, pinching, and fondling them repeatedly before moving down to her legs. I placed my head in between them, grabbing her thighs and rubbing them against my cheeks, even licking her thighs a little too, which got even more of a reaction out of her. Noticing this, I spread her legs wide, taking a long sniff of her pussy before lapping at it enthusiastically, listening with immense pleasure as her moans grew even louder and she orgasmed. Still vigorously sucking on her pussy, I rolled her over onto her front, then removed my tongue from the pussy to look at that perfectly rounded ass.
I waited a minute, knowing that she had no way to see what was going on or what I was about to do, before giving it a hearty smack. She shrieked in surprise, but I could tell she liked it because when I drew my hand back she stuck her ass in the air as if asking for more. I spanked her again, and again, and again, and by the time I finished she was groaning in painful pleasure and her ass cheeks were red and raw. I gave her a few seconds, let her think it was done, before giving her one last slap right to the ass cheeks, the hardest one yet, and causing her to cry out in pain.
“Do you want me to lick it better for you?” I asked, taking in the sight of her perfect, freshly spanked ass as I waited for an answer.
“Yes! Yess, please!”
“Are you sure?” I asked sarcastically, “Because I’m thinking maybe you’ve had enough…”
I started to stand up, but she rolled over to look at me, her eyes *begging* me to stay. The look of longing on her face, of *desperation* for more turned me on more than any seductive glance ever would.
“Well, alright, if you *insist*,” I said with a smirk, sitting down. She rolled back over, sticking her ass up onto the air once again, and I could see that it was still raw from the fierce spanking I had given her. Well, little did she know, it wasn’t done. She expected my warm, soothing tongue, but what she got was yet another vigorous spanking. I slapped her ass again and again, making it seem like I would never stop, sure that at this point her ass must be *throbbing* in pain. She scream-moaned as I did this, but kept wiggling her ass in the air, giving me a perfect view of her asshole as I spanked the cheeks.
After at least ten full minutes of this, I firmly grabbed her ass with both hands, pushing downwards. She had been sticking it up into the air, but now it was pressed onto the floor hard. I kneeled on her back, resuming the spanking, smiling as she flailed under my weight and her ass became redder and redder, rawer and rawer, but she never once asked me to stop.This continued for yet *another* ten minutes, until finally, at long last, I decided she had earned an end to the spanking. I kept sitting on her back, but leaned down, moving in with my tongue and started licking all over her raw bootycheeks, amazed at how squishy they were. It was made even better by the fresh quality that was a result of such a long spanking. I gradually moved my tongue to her asshole, groping around as deep as I could as her moan changed to a low hum.
After a long while of this, I ran my tongue along the area in between her asshole and pussy, and rolled her back over — becayse she couldn’t roll over herself, she was voluntarily limp at this point, completely powerless — to get back to her pussy, moving my tongue around inside her as I spread her legs out wide, pushing them outward to the limit of how wide they would go and taking pleasure in the long, submissive moan that followed. We stayed like this, with me furiously licking inside her pussy and her moaning in exhaustion and pleasure, until I lost track of time. It must have been a good twenty or thirty minutes, all of which was spent with my tongue inside her, by the time I heard the door to the house unlock and open.
*Fuck,* I thought, *her parents are home.*
She heard it too, and similar expressions crossed both our faces. We could hear their voices talking, they were wondering where Maisie was. We heard their footsteps getting closer and closer to the door to the room we were in. Thinking, fast, I removed my tongue from her wet pussy and got into the pool, pulling her in as well and savoring the feel of her warm body against mine. We stayed above the water until we heard the door open, at which point we both plunged below the surface, desperately hoping they wouldn’t notice us.
As we hid, she slid her hand into my shorts and squeezed my ass hard in her nervousness, massaging it despite the circumstances, and I couldn’t stop myself from doing the same with hers. We could faintly hear her parents’ voices even though we were underwater.
“She doesn’t seem to be in here, let’s check her siblings’ rooms. And where’s the babysitter?” Her dad said.
Her mother’s reply came almost instantly. “Wait a second, are those her clothes?”
*Damn it!* I thought, inwardly scolding myself. We had forgotten to hide her clothes, they were just sitting there on the pool deck, betraying our presence. Her grip on my butt tightened as she remembered too.
Only a few seconds after that, we were spotted. Her father pulled her out of the pool, leaving me to climb out myself. He gave her a harsh scolding before telling her to go to her room. She did, and he turned to me. He told me to stay away from his daughter, that I had no right to rape her like that. I tried to reply that she had agreed and that she was 18, but he didn’t care. I began to feel sorry for her, having such restrictive parents. Her father sent me out of the house, telling me never to come back.
But as I drove home dejectedly, still daydreaming about what had just happened between the two of us, I noticed something: a slip of paper in the bag containing my clothes. I pulled it out, and was elated to see that there was a number written on it — Maisie’s number. She must have put it there on the way to her room, while both parents were distracted with me. A spark of hope lit up inside me, and beyond the hope, a hunger, a hunger for her, for her juicy pussy, her rounded boobs, and her squishy ass. I would text her when I got home, and maybe, just maybe, I’d have a chance at meeting up with her again. And when I did, I would go even farther than I had the first time.
Source: reddit.com/r/gonewildstories/comments/s35jvd/i_20m_took_a_babysitting_job_didnt_expect_their
But did they pay you for babysitting the other 3 kids?
Things that never happened: this.