The Dad and the Sitter

We had been fucking for a few weeks. She was leaving school early and I was skipping out on work a couple of times a week so that we'd have 2 hours of alone time together before my kids got out of school. She wasn't a virgin, but she wasn't super experienced either. She'd only had sex a handful of times with a senior she went out with last year. They had barely done more than missionary and girl on top and he had always worn a condom. He never ate her out or played with her asshole or shot his cum on her or in her. What a fool. I was determined to turn her into a dirty little fucktoy before she went off to college and I was gonna spend the next 4 months training her how to make an older man happy with her tight little body.

So far we had been working on her deep throat skills (she was natural) and I'd been fucking her sweet little cunt raw without a condom. I would constantly remind her how tight she was while I fucked her little pussy and tell her how badly I wanted to be the first man to ever cum inside it. I'd tell her THIS was the time I was going to fill it up but she'd always freak out and ask to me pull out because she was scared she was going to get pregnant. She had very little faith in her birth control pills. As much as it annoyed me and as easily as I could have just cum inside her with or without her permission, I really wanted her to WANT me to do it, and so each time she requested I would reluctantly slide my cock out of the impossibly tight perfect little teenage pussy and shoot my load all over her tits, ass, stomach, or face instead. It was hot but a little frustrating. I was a patient man, but not THAT patient.

One afternoon after we'd finished having sex, she lay in bed nude on her stomach, feet up in the air crossed together just staring at her phone. She looked adorable and sexy at the same time. I asked her what she was looking at.

Her: Dresses.

Me: You need a dress for something?

Her: Yeah, spring formal is in a few weeks. My mom bought me something but I hate it.

Me: Why didn't you get her to buy you something you like?

Her: Well I found this one dress that I thought looked really hot but she said it was too sexy and she gave me the option of these three different dresses and I hated all of them, so I just picked the one I hated the least.

Me: Hmmmm. What if I bought you the dress?

Her: Yeah?

Me: Sure, I could keep it for you at the house and you could grab it the day of your dance and get ready at a friend's house.

Her: I don't know. Wouldn't your wife think it's weird that I just have a dress at your house?

Me: I will stick it in the guest room closet. She never comes in here. This is basically my space to hangout, play my guitar, listen to records, fuck your little pussy.

Her: You are so bad.

Me: Yep. SO do you want me to get you the dress or not?

Her: Yes please.

Me: Okay, my only rule is you aren't allowed to wear any panties with it.

Her: Oh my god. No I can't do that. It's really short.

Me: I guess you don't want me to buy it for you then.

Her: No! I want it. Okay, NO panties. I promise.

And so with that I gave her the money for it and she brought it to the house and stuck it in our guest room closet the next time she watched the kids. It sat in that closet for 2 weeks and just as I had said, my wife never saw it. The day of the formal, she came and got it from me. "Thank you so much, for this." she said. "Anything for my sexy little girl. Just make sure to send me some pictures of you in it." She promised and then left.

Around dinner time, she sent me a few pictures of her with her friends all done up in their dresses. She looked sexy. It was black, with a deep V in the back that went almost to her waist and it was very short and absolutely clung to her. It made me a little bit jealous I wasn't going to get to enjoy her in it and I imagined some lucky high school boy having his way with her in the backseat of his car after the dance. A few hours later she sent me another picture making a kissy face with the text "thank you". I responded back. "I can think of a few ways you can pay me back for it." 30 minutes later I got a picture from a bathroom where she had the skirt hiked up just a little bit so that you could see the bottom of her ass cheeks with the text "see no panties", I was instantly hard. "You are gonna be in so much trouble when I see you again." I responded. She sent nothing else and I figured she was probably done teasing me. The kids were asleep and my wife had gone to bed at her usual time of 9:30, meanwhile I was on the couch watching basketball. At around 11PM I got another text from her.

Her: i need help.

Me: Yeah, how so?

Her: Can I call you? Is it safe for you to talk?

Me: Yeah let me go outside. Hold on.

I went out into the backyard and gave her to okay to call. I picked up and I could instantly tell she was drunk. She told me a very long and rambling story about leaving the dance with her friends and going to a house party at some kid's lakehouse, she said her friends had all either left or were hooking up with guys and that she was stuck. She pleaded with me to come get her. She said she just needed a ride to her friend's house where she got dressed but that her friend wasn't answering her phone or texts. This was a real pain in my ass. Luckily my wife can sleep through a tornado. I told her to text me the location and I'd be there to pick her up in a little bit.

I jumped in my truck and drove out towards the lake. It's about 20 minutes from my house and once I got out there I saw the street was full of cars parked up and down both sides and drunk teenagers were everywhere. Hardly anyone lives in this neighborhood full time, it's just a place where all the rich people in town have their weekend lake houses and so it's definitely a perfect place to have a party. It was when I was a teen and it still was today. I started to realize I looked conspicuous as hell picking up a teenage girl at this party and so I drove down to the end of the street and parked and then I called her. I sent her a text "hey i'm here. where are you?" No response. I called her. She didn't answer. Well there was no fucking way I was getting out of my truck and going to this party to look for her, So I cranked my truck back up and was getting ready to leave when I saw her. She was standing in the middle of the street talking on her phone. I drove up to her. "Get off the phone and get in." She did as I said.

Me: Why didn't you answer the phone? I drove out here because you asked me to. I could be at home in bed right now.

Her: I'm sorry, I was talking to Aly. She's at some guy's house. I told her I need to get into her house to I can get my stuff but she's not going home.

Me: Okay, well what do you want to do? Do you me to take you home?

Her: No, I can't go home. My parents will freak out about this dress and they'll be mad I'm drunk.

Me: Yeah I can imagine. Are you wasted?

Her: No, I just had like 4 beers I think. And maybe a shot. and I also smoked a little bit of weed. (She laughed trying to remember everything)

Me: Jesus Christ. I don't know what I should do with you.

Her: Yeah you do. You know exactly what to do with me. (she said in her poorest attempt at a sexy voice)

I looked over at her, she had pulled the skirt up over her hips and had her shaved little pussy completely exposed to me.

Her: I feel so sexy in this dress. You should fuck me in it.

My cock was hard as a rock. I pulled off on a dirty road and drove down towards the lake, towards the marina. it was pitch black. No one was out here. I parked my truck and unzipped my pants. "Come her" I told her, and she instinctively put leaned into my lap and put her mouth around my cock and started sucking it like she did every time we were alone together. I hiked the skirt up around her waist so I could see her perfect naked ass. I smacked it hard. She yelped but I grabbed her by the back of the neck and started the fuck her face. I smacked her ass again, harder this time. She moaned around my cock and I rained down more smacks to her round peachy little backside.

Then I began to stroke her wet little slit with my fingers, teasing a few inside and then also sliding my thumb into her asshole. I had a cock in her mouth, two fingers in her cunt, and a thumb up her ass. I told her she was a dirty little slut in that dress and that she was gonna get her little holes all used tonight. I took her head off my cock and looked at her. "I want your pussy right now." I said to her. "Are you gonna let me fuck it how I want?" "Yes" she panted. "Are you gonna let me fill it up with my cum tonight?" "Yes" she replied. "No backing out, if I fuck it, I am cumming in it. Deep. Do you want that?" "Oh fuck. Yes." with that I was on top of her and inside of her with one quick motion. The passenger seat leaned all the way back with her legs wrapped around my waist. My cock thrusting in and out of her wet perfect young cunt deep and hard.

Me: God you feel so fucking wet tonight. I bet all the boys wanted to fuck you at that party.

Her: Yeah, they did.

Me: They could smell what a little slut you are. They could tell you're in heat.

Her: yeah. fuck.

Me: Did you let any of them fuck you tonight?

Her: No.

Me: Did you suck any of their cocks tonight?

Her: No.

Me: You promise. I know you like sucking cocks.

Her: I swear. I didn't suck anyone. I didn't fuck anyone.

Me: Why not? You're dripping wet and I know you wanted to get fucked in this little slutty dress.

Her: Cause I'm yours.

Me: That's a good girl. Your little mouth belongs to me, doesn't it?

Her: Yes.

Me: and so does your tight little pussy, doesn't it?

Her: Yes.

Me: Are you gonna let me cum in it? Are you gonna let me shoot my hot cum into. The first man who ever filled you with cum is gonna be me, isn't it?

Her: Yes, fuck please. fill me with your cum.

Me: Good girl.

With that I began jack hammering her pussy as deep and as hard as I had ever fucked it. I could feel her little cunt throbbing, as I gripped me shaft. She was moaning and panting and saying my name and begging me to cum inside her. Telling me she was mine. I couldn't last a second longer and bottomed out one last time as I shot the biggest most intense load of my life into her tight perfect 18 year old pussy. I left it inside of her to make sure she took every single drop. We kissed for a long time, she said how hot that was and I got hard again and fucked her pussy for a little bit more, but couldn't manage another load. I was spent. We drove around in my truck for an hour or so, after that. We talked all night. Finally her friend Aly was done hanging out with the guy and I was going back home. I dropped my sitter off down and the street from her friends house and went back home. Everyone was still sound asleep. I crept into the guestroom and went to bed with thoughts about my beautiful sitter and what a lucky dirty old man I was.