[MF] Babysitting! (18F)

This is a story that I personally like a lot and I’ve been wanting to write about it for a long time, so it’s my pleasure to offer it to you :)

I started babysitting for this guy when I was around 14. It was pretty much the only job I could take in the small city I lived in. When I turned 16, I could have taken a better job, and I did get a job at one point at a grocery store to supplement my income, but I had gotten attached to this family quite a bit. At 17, his wife left him for someone she met on the internet and the pair divorced; for a reason I ignore, he ended up with custody of his children, except one week-end every two weeks. I think she didn’t have a very stable life or did not care much about her children.

Together, they had had three wonderful boys that I adored; by the time this story happened, I had been babysitting for four years and the oldest one was almost 12, certainly old enough to babysit his siblings for a little bit, but not overnight. I was certainly used less and less, as the mother also had custody of them sometimes, but the father would still call me here and there for a night. Sometimes he would have to work late and wanted someone to take care of his kids, make sure they could eat (i called delivery) and so on, and that they brushed their teeth and so on. Sometimes he was on a date and would make me babysit overnight (!!!). I absolutely loved the kids and he paid for the entire night, which was awesome. Sure, I earned a bit less per hour than at my grocery store, but the joy was much more enjoyable – during the best days, I was even paid to sleep :).

This story happened shortly after I turned 18. I know what it’s going to sound like, but I think he genuinely did not know I had turned 18. He was supposed to go on a business trip in a neighboring city and didn’t want to drive back (4 hours) every night. I was hired from Friday 6PM (after school, I was in grade 12) to Sunday 8PM or so. I should also say, at 18, I really, really, really wanted a car. I had already gotten my license a year back, and sometimes my parents lent me their car, but it just wasn’t enough. I wanted a car to drive to my school (with friends), I wanted a car to drive to work, I wanted a car to go out downtown, etc.

A family member happened to have the perfect one. My aunt didn’t drive much and, after our town expanded its bus services, kind of realized she did not need a car anymore. The car was worth $4,500 easily, in fact I did end up reselling it a few years later for more than I paid for, but since it was me, she was ready to let it go for the rock bottom price of $2,000.

I had around $1,000 saved up from work, gifts and so on, and I badly wanted that car. In good condition, low mileage, etc.

I charged $10 per hour to babysit, so the entire week-end would net me a nice, round $500 (the guy didn’t even try to bargain or negotiate a lower price, “you’ll be sleeping 8 hours so I’ll pay less etc etc etc). We just agreed on $500. Then again, I would have to cook a few meals, bath the youngest, make sure they brush their teeth, go to bed on time, etc.

I was super happy about getting that huge amount. It would mean I would only need $500 for the car and I was sure my mom would loan it to me happily.

The first day of babysitting went super well. Not going to bore you with the details, but I had zero problems. His kids were polite and nice. Barely argued with me. Did homework by themselves. Yeah, that kind of work. The first night I felt awesome getting paid to sleep (!!) and the man even allowed me to sleep in his bedroom, a large, king-sized, super plushy bed.

During that night, I couldn’t help touching myself. It’s kind of dirty, but I’ll say it anyway: this was the bed the man had fucked his wife in multiple times. This was the bed he had made those children I was babysitting. I found myself super aroused by the idea and touching myself until I was soaked wet. I felt a bit bad about soaking his bed, but surely it would dry off, or I could wash it.

I fantasized about the man too: tall, dark, good-looking, charismatic. Very nice, very polite, but firm. Dominant who always looked at me in the eyes with a smile, not even a shadow of self-doubt or hesitation in everything he did. I started to imagine myself as his wife and imagine him fucking me. To be honest, masturbating in his bed had been a fantasy of mine for quite some time, and I was happy to fulfill it. Just getting in that bed and imagining the two of them going at it made me horny.

The next day, he had left me money for pizzas, so me and the boys had exactly that. I laid them in bed and wrapped myself in a blanket to watch a movie. He had that huge living room in the basement with a huge TV (and gaming consoles) that was just awesome.

I was shocked when I heard the front door open, or at least I was sure I had heard something. I became quite afraid, until I saw his familiar face enter the basement.

“I thought you would be here. Are the kids asleep?”

“Ye… Yes, sorry,” I said, a bit startled.

“Don’t be sorry! You couldn’t have heard me open the door,” he said.

“You’re already here?”

“We finished the business deal early. And the hotel was so uncomfortable, I couldn’t picture myself spending another night there. I know it’s late, but I made the drive back. How was it?”

“It was fine,” I just said.

I was a bit… disappointed. Usually, when he came early, he only paid me for the hours I had babysitten (is that even how you conjugate that verb? lol). Since it was around midnight, he would pay roughly half, maybe a bit more. That was over $200 I was missing, or around 10% of my car. A huge amount.

“You didn’t receive my texts?” he asked.

And on this, I realized my phone had been charging upstairs for a bit.

“It’s okay,” he said. “I know I arrived early, but I hired you for the week-end, so you can stay for the week-end.” I froze a second, thinking about his bed full of my juices. Maybe he wouldn’t notice? I decided to go get my phone and, sure enough, there were several missed texts of him coming.

“I’m sorry about that,” I said. “I don’t really understand how this phone works totally, I got it just a few weeks ago for my birthday.”

“Your birthday?” he asked.

“Yeah, I turned eighteen.” When he heard that, his face completely froze. I’m not sure why I even mentioned my birthday in the first place.

“You should have told me it was your birthday. I would have gotten you a gift.”

“Please, sir, it’s not necessary.”

“Call me Charles. And we’ve known you for so long, it’s only natural. C’mon,” he said, opening his fridge and grabbing a six-pack of beer. “I see you haven’t even touched my beer. I wouldn’t have been mad,” he joked.

“I don’t… really drink much,” I said. And it was true. At parties, I drank one beer, maybe two in a night. It’s not that I didn’t like it, but I usually got very few chances to drink beer, as I didn’t party much, and the people I partied with tended not to drink much.”

“It’s a tradition to drink a beer when you turn 18,” he said.”

“It’s 21,” I said.

“I know, but c’mon,” he said, throwing me a can. “You were watching a movie?” he asked.

“Yeah.”

“I could use a movie to relax.”

He took a bag of chip, poured it in a bowl, then went downstairs carrying his remaining five beers. I took a sip of mine and followed him. We sat down on the couch quite far apart and started watching the movie.

The beer was oddly good. The kind that is light, or at least taste light, but gives you no aftertaste. By the time I was half-done, he had finished his and was grabbing another. He seemed focused on the movie and I decided to drink faster, I’m not sure why, to catch up with him.

“Take as many as you want,” he said.

“Thank you.”

“Everything went well with the boys?”

“Yes si… Charles,” I said.

“Good.”

I was about half-way done with my second beer when he asked me if I minded if he put on something more comfortable. I said I didn’t, and was getting ready for bed too.

“Well go put on something more comfortable too,” he said as he stood up.

I had my pajamas, which were still quite childish in nature. A long-sleeved pant with some drawings and a tank top that perfectly showed my curves. I thought it was a good idea and went to the bathroom to change. He came out of his bedroom wearing a pair of boxers and an undershirt. he looked muscular and powerful, yet relaxed.

We sat down on the couch again and I quickly finished my second beer. The chips had made me thirsty.

“Charles, do you mind if I take another one?”

“Oh no, go ahead.”

“You’re lucky to have three nice children like that,” I said.

“Thank you. I did my best, as a single father, you know? For a year now.”

“Yeah.”

I was getting more and more comfortable. Tipsy, but also… Don’t laugh, but I could not help but look at his crotch. The boxers he wore really made a nice curve there and I thought he must be huge.

“You look tired, you should lay down,” he said.

“Yeah? The couch is too small for both of us to lay down.”

“Just go ahead.”

I laid down, putting my head on the couch’s shoulders, but my feet ended up just next to him with my legs bent.”

“It’s okay, put them over me,” he said. I did and my feet were right on his lap. “You know, my wife said I gave amazing foot massage,” he said, looking at mine. “You worked quite a bit today with the kids.”

“I didn’t work that much!”

“Well I know they can have energy. I bet your feet are tired. Would you like me to massage them?”

“You’re going to miss the movie,” I said. “But okay, sure.” I had never gotten a foot massage.

He stood up and came back with some oil and tool of some kind. Then he rubbed and caressed my feet, good and long. He had strong hands and could really push and massage the muscles. It felt good, incredibly relaxing and somewhat… I don’t know, sexual in nature I guess.

“You are a grown woman now,” he said, smiling.

“Hmm-mm.” God it was good. Learn to give foot massages, guys!

“Is your back tired? I give good back massages too,” he said, as he was finishing up my feet.

“Yeah, sure!”

I turned over on the couch, on my stomach. He put his hand at the bottom of my back, under my tank top, and started working his way up, his strong, powerful hands rubbing my back. I pulled my tank top up to my breasts and he managed to massage my upper back under it. God that one spot near my shoulder muscles or something, it felt so GOOD and I moaned in pleasure a bit.

“It would go a lot better if you removed it, do you mind?”

“Sure, go head,” but before he could do anything, I removed my top by myself. My breasts were pressed again his couch. He gave small but precise hits with his palms where the muscles are and continued to massage the muscles.

During that time, he also caressed the sides of my breasts, on each side, and he made my heart jump somewhat. Only at that moment did I realize I was in his house with my breasts exposed. What if his kids saw us? I had the natural reflex to cover myself a bit with my hands, but did I really want to?

“Relax,” he said, and I felt the hot oil on my breasts, warming my body up, and turning me on incredibly. He pushed his hands under my pants to grab my ass, and massaged it somewhat. I felt incredibly vulnerable, but loved it soooo much. He then asked me to turn around and I obeyed immediately: he started massaging my belly, then worked his way up to my breasts.

“Sir, it’s not okay…”

“Shhh…”

“Your kids are asleep upstairs, it’s, it’s…” wrong, I was going to say. But they were hard asleep, there was a floor between us as well as a few doors, and I didn’t mind it that much. He started to caress my breasts and soon I lost it, horniness completely overtook me.

I felt warmth down on my pussy and opened my eyes to wet my wetness had leaked through my pajamas. I remember panicking a bit, thinking I would damage his couch or something. He told me to calm down again. He caress my breasts with his strong hands until I was so horny it was unbearable; then, he worked his way down, sloooowwwllyyy, and started caressing my thighs, using his fingers to move the muscle underneath.

“Again it would go a lot better if you removed it. Massages are usually… without clothes,” he said.

Truth be told, at 18, I was sooo shy about my body. I was afraid men wouldn’t like it, would be repulsed by my naked body, I didn’t like my body very much. I was insecure and felt I had grown too much at some places, and too little at others. I didn’t really think men could find my naked body attractive.

He started to pull my pants down, slowly, and I whispered a quiet “no,” using my hand to gently stop him.

“Is it because you’re insecure? About your body? Don’t worry about it,” he said. He stood up, and removed his shirt and boxers. I could not help but stare at him. He had a sharp, strong body and a dick that was already hard. My first thoughts were: oh my god he’s much bigger than my last boyfriends, the two of which I had had sex with, which hadn’t been very pleasurable. “See? That’s how I am. I’m sure you’re a beautiful young woman under those clothes,” he said.

“Okay,” I replied.

“I want to massage your clit so bad,” he said. “Only part I have left.”

“Okay,” I said again, and feeling some confidence, I lowered my pants until I was naked.

“Amazing,” he said, looking at my pussy. He started rubbing my clit, very gently, and I opened my legs wide almost automatically. Then, he brought his tongue to my clit and starting licking and OMG, I had never gotten anything like this. I had given head, of course, but had even no idea men could do it to women! It felt incredibly good, as good as a blowjob would feel for a guy I feel. He worked me up until I was seconds away from cumming. Then, he laid his body over mine, kissed me, and asked:

“May I please enter you?”

I kissed him back and using my hands to pull him towards me. He slid in me right away. With my previous two boyfriends, it had been difficult: pretty much hurt every time, wasn’t very enjoyable. This guy was on another level. Longer and wider than them, he also knew how to make love. Shallow penetration, deep. Shallow, deep, over and over again.

“Did you know, we made our youngest one here,” he said. “Right on this couch, same way we are doing now.”

I had gotten an orgasm before, but only a few times, and nothing as good as this. It only took him a minute of fucking me to bring me to the most powerful orgasm of my life and up until that point, I had no idea orgasms could be so good.

As I orgasmed, I felt a bit scared his kids would hear me. “Let loose,” he said. “Let loose.” I started screaming in pleasure as my body orgasmed. I grabbed him and let the orgasm control me as he kept fucking me. I moaned in pleasure for over a minute, every second being pure elation. God it was good.

As I finished, he asked very politely:

“May I please orgasm in you?”

“Yes, please.”

“You are a beautiful young woman” he said, and he tightened up his fucking. Now, he was thrusting harder and faster. Very soon, he started panting and moaning, and bit me softly on the shoulders.

“Is your pussy ready to get filled with my cum?”

I don’t know what was going on with me. I usually couldn’t orgasm twice in a row. I needed a break, to do something else, and even there, it was rare for me to reach orgasm twice.

“Yes.”

“That’s the same cum that made the three little kids you babysat,” he said. “And I’m going to fill your pussy with it.”

He went faster and faster, until he pushed all the way inside me, and right as he came, I came again. Unreal how fast he had made me reach orgasm – twice. He seemed to really enjoy his time too as he took his time to really drain himself inside me, until his dick was totally flaccid.

I really, really thought it was done. With my boyfriend, when they ejaculated, usually in my mouth, but sometimes in my body, they just wanted to… sleep, I guess. At least they weren’t interested in sex at all. But Charles kissed me and said it was the best pussy he had ever fucked, and it was HOT. He said he was going to “fill me” at every place he had made a kid.

“The first one was in our bedroom, same bed we have now. Our second kid… I guess I’ll tell you after,” he winked at me.

He grabbed me, one hand under my upper back, one hand under my knees, and lifted me without problems. Cum was starting to leak out of me, but he didn’t seem to mind. We walked upstairs, nude, and he brought me to his bedroom, and fucked me doggystyle. He continued until he came, and I felt him coming, and felt super hot.

“You wanna know where we made the second one? The middle one?”

“Yes please.”

He brought me to his garage, pushed up the two front seats, and sat in the back one. Quickly, he had me sit on him, still naked. We kissed and it took a minute or two until he was hard enough to penetrate me. This time, I was on top.

“Do your work,” he said.

“I’m… Not sure how.”

“You’ve given handjobs before? It’s like that, but use your entire body instead of your hand.”

I did the best I could and he guided me. “Just do whatever feels pleasurable to you. Try every move you want until you find something that can make you come, then do that until you come.”

I tried moving forward, backward, up, at an angle… Eventually, I found an angle that felt really good to me, I think maybe hit the mythical g-spot, and I decided to do that angle only. I fucked him, my juice and overfilled pussy dropping on him, and it was harder and harder to keep his dick in with all that slippery stuff. Then, I think I hit the spot exactly, because I felt a powerful orgasm coming as he grabbed my bouncing breasts.

Within a few thrusts, I came, and this time I wasn’t afraid of any kids hearing, so I screamed in pleasure, letting myself go completely; just a few seconds into the orgasm, he pushed his hips up and came.

“Beautiful little woman,” he said. We kissed and he carried me to bed. Then, I remembered our clothes laid on the basement floor, and panicked a bit, fearing the kids would find them in the morning. He was nice enough to go grab them, and we feel asleep quickly, in each other’s arms, naked. When I woke up, I saw him looking at me and without a word, he penetrated me. I wasn’t wet, I wasn’t ready, but it honestly didn’t hurt. I think he had fucked me enough in the night before that… I don’t know, actually.

Within a few seconds, I was wet again, and I remember thinking it was so nice the kids let us sleep. Within a minute, I no longer thought of the kids I was supposed to babysit, cook breakfast for as I found myself about to orgasm again, his dick doing its magic inside me.

“I can’t yell too loud, can I?”

“Scream in a pillow,” he said.

He turned me over, switched to doggy style, and I did as he asked. This time, he asked to ejaculate over my face, and I agreed. I would have agreed to almost anything at this point.

He made me suck him, and I didn’t mind my juices covered his dick. As he came, I closed my face and he covered my face and breasts in cum. Damn it felt hot, he told me to go near his wardrobe as he had mirror door, and seeing myself like that turned me on so much.

I came back to kiss him and he told me kids had to eat. He said he was going to cook for them, and that I should lay in bed until he came back. I said “okay” and that I was gonna sleep in a little.

“Don’t clean yourself, he said.”

I think he cooked for all his kids, they seemed very happy to get their dad back, they seemed to really loved him. He asked them to go play downstairs or something, because he brought me delicious pancakes with coffee.

“Can I push my luck to get one more use of your pussy?” he said.

“Our contract said I would be here until 8PM I think, so you can use my pussy as much as you want until 8PM.”

As I kept eating, he went down on me to “eat me” and I started to eat faster and faster, almost gorging myself with food. . There were still some cum dripping from my breasts and face, although the pillow and sheet had grabbed most of it.

Finally finished, he pushed the breakfast tray away, then using the pillow covers to tie my wrists to his bed post roughly.

“What are you doing?” I asked. The restraints weren’t super tight and if I struggled, I could certainly undo them, but I didn’t.

“Shhh,” he said, and he tied one last pillow cover around my mouth, saying: “can’t have you scream from your orgasm, the kids would know.”

Without control of my hands, it was a totally different experience. I felt dominated and totally controlled. He entered me pretty fast and fucked my helpless me until I came, the pillowsheet in my mouth absorbing my orgasm. He came in my stomach this time, finishing himself and shutting his stuff all over me. Not much I could do about it – except enjoy it. At last, he laid next to me, kissed me, and told me I was amazing, and that was better than any sex he had ever had – his wife or otherwise.

He untied my wrists and finally allowed me to shower. I dressed in my change of clothes and went to join the kids downstairs. I decided to use his soap, to smell like him. Apparently, they had not noticed anything or didn’t ask any question on where I was.

As 8PM nearer, so did the end of my shift. Originally, he was supposed to finish his business by 2PM at the latest and arrive here at 6PM at the latest, enough for an hour or two to spare. I had to go home and prepare for school early the next morning. “No no no,” he told privately. I absolutely need your amazing pussy one last time.”

I helped him put his two youngest in bed, but the latest one didn’t want to hear anything. “I don’t go to bed until 9,” he cried.

“What’s the game you wanted so much?” his dad asked, and he mentioned some gamecube or wii game, I’m not sure. “If you go to bed now, daddy will buy it for you tomorrow coming back from work.”

The kid smiled and immediately accepted.

As 8PM rolled, he had be naked in his basement, bent over the couch’s shoulder, and fucked me hard and fast, almost last he had to hurry. “I want you to keep this load in until you go home. Can you please not shower and go to sleep with it?”

“I’ll try.”

“And I need to see you again,” he added.

He finally finished, but not before I came first. He had brought a mirror and I wasn’t sure why, but watching me being bent over and fucked by a strong man turned me on soooo much. He gave me a deep hard fill, then helped me put my panties on.

“Remember, you go to sleep like that. In your pj, no cleaning.”

“Okay,” I replied, still horny.

He led me to the door and at that moment, I had totally forgotten I had to get paid. He hadn’t, and started counting the $20 bill.

“Do you have any plan for the money?” he asks nonchalantly.

“Yeah,” I replied, just chatting. “I’d like to buy a car.”

“How much you missing?”

“About a thousand,” I replied.

He paused a second, then started counting again.

“Here, a thousand bucks,” he said, handing me a HUGE pile of twenties. “Enjoy your new car and drive responsiblity, okay?”

“Sir, it’s way too much, we agreed on $500.”

“But you did such a nice job babysitting my kids. You deserve it.”

“But…”

“You deserve it, Sarah. Take care and enjoy your car.”

This was the most money I had ever held in my hand and I couldn’t believe how lucky I was. By next Friday, the car was mine. I hadn’t thought of insurance and the cost for registration unfortunately, and would have been a bit short, until I received a text message saying his kids “urgently” needed babysitting tonight. I asked him if I would still get $10 per hour and he said yes.

By the time I arrived, his kids were not there – it was their mother’s week-end to get them. He invited me in, and let me just say that by the time the week-end ended, I had plenty for insurance and registration :).

Source: reddit.com/r/gonewildstories/comments/dhlma2/mf_babysitting_18f