Fucking a Reluctant Sitter

My babysitter, Melissa was downstairs watching my son while I was working in my office upstairs. My wife was at work so we needed Melissa to watch Mark so I could get my work done. Melissa was very plain looking and was about 5'4" tall and around 120 lbs and had dark brown hair. She just put Mark in for a nap and was watching TV when I called her up to my office. It was her 18th birthday.

"Happy Birthday Melissa!" I handed her 3 presents. "Open this one first."

She said "THANKS MR C!"

She opened the first present, "Wow! It's a digital camera! Thanks! I know this costs a lot Mr. C, are you sure this is ok with Mrs. C?"

"Melissa, Mrs. C doesn't need to know about this and don't tell anybody else that I gave this to you."

"It's out secret Mr. C."

"Melissa, let me take a picture of you with your new camera."

"OK Mr. C"

"Give me a sexy pose honey."

"MR C!!! I can't do that!"

"It won't hurt anybody Melissa. You're not a little girl anymore now that you're 18. It will be our secret, please"

"OK but don't tell anybody or show anybody." She turned her back to me and stuck her ass out and turned her head towards me. "How's this Mr. C?"

"Hot! So hot, you have a great ass." I took a few pictures and said, "Honey do me huge favor and pull you shorts down a little, just for the picture."

"I'm not sure Mr. C, you're old enough to be my dad and what would Mrs. C think if she knew you asked me to pull my shorts down so you could take a picture of my bare ass?"

"Mrs. C and I are married in name only. We don't even sleep together anymore so she doesn't care what I do. If you don't want to show me anymore I understand; you might not be grown up enough for that."

"I'm a grown up now, I'll show you!" She pulled her short down a few inches and I saw her butt crack and her thong. She had a perfect ass, it was not a little girl ass anymore but it wasn't too big.

I took a few pictures of her ass while saying "what a perfect ass you have, beautiful. OK honey, open up this present now."

She opened it and said "Oh, I love it, what a nice skirt, thank Mr. C!"

"Try it on honey."

"OK, where do I go to change?"

"Stay here and let me take a picture of you changing. I already got a picture of your ass with your thong on so it won't be much different."

"Oh I don't know Mr. C."

"Come on honey, we'll just keep it between you and I. You have such a hot body and I always thought you were the most beautiful girl I've ever seen."

"Gee thanks Mr. C! I guess it would be ok but I feel weird about it."

"Thanks Melissa, don't feel weird, we're just having fun."

She pulled her shorts off and started to grab the skirt and I said "Melissa, let me take a few picture before you put the skirt on. It will be a before and after shot." I didn't wait for an answer and kneeled down in front of her and took a few shots of her thong covered pussy. "Turn around now and bend over." I gave this to her as more of an order than a request.

She slowly turned and bent a little and I said "bend all the way honey, it will be a real sexy picture." She bent over all the way and I said "spread you legs wide."

"MR C! You'll be able to see my private area if I do this."

"Your thong will not let me see it, spread them and let me see if they show." She spread her legs while bending over and her thong didn't hide her asshole at all. I could see her beautiful tight puckered asshole barely covered by the thin thong. I could only dream about shoving my cock in there. The top of her pussy was still covered but I could see the bottom clearly. Her pussy lips were barely visible because of all the pubic hair covering it. I wouldn't be surprised if I was the first one to ever see her pussy because she was so shy. I took a few more pictures and then asked her "You were right, I got some good pictures of your ass and your hairy pussy. I love it when there is a lot of hair."


"Sweetheart, your pussy is the most beautiful that I've ever seen."

"Really Mr. C, I didn't know that."

"I can't believe your pussy looks so beautiful for your age, it's not like a little girl's pussy. It's a grown up woman's pussy."

"You really think so Mr. C? I'm glad you think it looks so nice. Do you really think it looks like a grown up's pussy?"

"Yes honey, do me a favor and let me get a good picture of your pussy."

"I don't know Mr. C; I've already gone too far with you."

"I already got a picture of your pussy, just let me get one more from the front. Turn around, lie down, spread your legs and pull you thong to the side."

"Mr. C, I don't want to."

"Please Melissa, I already have a picture of the back of your pussy, I just want a picture from the front. It's so beautiful; I can't believe how beautiful it is. The most beautiful one I ever saw."

I didn't wait for an answer as I turned her around and sat her down on the couch in my office. I spread her legs apart and pulled the thong to the side and took a few picture of her pussy. It was a beautiful pussy with lots of thick coarse pussy hair surrounding her tiny slit. "Melissa, it's beautiful, you are the most beautiful woman in the world. You should be a model or movie star."

"Thanks Mr. C; are we done yet?"

"Not yet honey, I need to get a picture of your pussy with your lips spread. That's what grownup woman do when they show their pussy to a man. I'll show you how it's done."


Too late, I already was spreading her lips and I could now see her closed up fuck hole. I took a few pictures while she just sat there in shock. She probably couldn't believe that a man old enough to be her dad was spreading her virgin pussy lips and taking pictures. "Oh Melissa, you're a beautiful woman with a perfect pussy."

"Mmmmm thanks, mmmm, nobody ever touched me down there, it feels weird."

"Oh honey, you're so beautiful. It feels weird because when a man touches your pussy; your body is getting ready for a cock to go in there." I wondered if I was pushing her to fast.


"I said that you're pussy is starting to get ready for that, not you. A woman's pussy lips gets bigger, her clit grows and she starts to get wet in her pussy hole. I can see that happening with you already. Look, you're getting wet, see." I stuck my finger in her hole up to her hymen and she was getting wet.


"OK honey." Now I started to rub her clit and she groaned.

"OH! OH! OH! Mr. C what are you doing? It feels so funny down there. Stop, please stop."

"I'm rubbing you clit Melissa. This is how a woman gets ready to fuck. If I keep this up long enough, you'll cum and then you're ready for a cock to enter your pussy."

"I'M NOT FUCKING YOU! I've never cum before but my girlfriends have and they said it's great. They had their boyfriends rub them just like you're doing now until they came."

I just kept on rubbing her clit faster and faster.


I kept this up for a while and finally she came. I took a few more pictures of her like this.


I stopped rubbing her clit as she finished cumming. "How was that honey? Was that the first time you ever came?"

"Oh Mr. C, it was unbelievable. I've never felt anything so good."

"Honey, that's nothing compared to fucking. Fucking is a 1000 times better than cumming just like you did."


"Yep, did you ever see a cock?"

"No Mr. C, I'm scared."

"Don't be honey; just let me show you what a cock looks like. You've got me hard from rubbing your pussy."

"No Mr. C, I don't think we should do this."

"You'll be the first one in your grade who has seen a grown man's cock. You'll be the coolest girl in your grade."

"I would be but I don't know about this."

I pulled my shorts and boxers off and stepped out of them and pushed my cock near her. She looked at it with curiosity and fright.

"It's so big. That thing would never fit in me. OK Mr. C; put it away."

"Come on Melissa, it's your first time seeing a real man's cock. Don't be a chicken; you're not a little girl anymore. Here, hold it, see what it feels like." I knew calling her a chicken and telling her she wasn't a little girl anymore would get her to try more things. I grabbed her hand and had her wrap it around my cock and helped her move it up and down. "This is how you jerk off a guy. If you do this long enough, I'll shoot my cum out of the tip." I took my hand away and she kept stroking my cock.

"Mr. C, is that cum on the tip of your penis?"

"No Melissa, that's called precum, it's just the liquid without the sperm mixed in. Don't call it a penis, grownup girls like you call it a cock."

She pulled her hand off my cock and said "I think that's enough Mr. C. If we go any farther you're going to try and stick you cock in my pussy. I might get pregnant because I had my period 10 days ago."

"Honey, I understand completely. I wish I had a condom because you would be able to fuck then; you would finally become a women."

"Mr. C, if you had one I would do it with you."

"Really, do you promise?"

"Yes, but I know you don't because you told me you and your wife never do it anymore."

"OK, you might as well open up your last gift."

She opened up the small package and looked at me in horror as she saw the present was a box of condoms. "MR. C NO! I CAN'T. NO, PLEASE NO."

"A promise is a promise." I grabbed the box of condoms, opened it up, took one out, ripped it open and put it on before she could move. She watched in shock as I got between her legs and rubbed my cock against her pussy. I took a picture again.


I started to push my cock into her pussy and took another picture and she screamed "MR CCCCCCCCCCC! OHHHHHH! OUCH IT HURTS! OH! OH! Oh my god it's in, it feels better now."

My cock head was now in Melissa and she was crying and I took another picture "Mr. C you took my virginity, please take it out, it's wrong, you're old enough to be my dad."

"Don't cry honey, you're going to enjoy this as soon as you get over me popping your cherry. I'm going to push it all the way in now. Spread you legs wide and lift you knees."

She did this and I started to push my cock in. It was slow work getting it in and she was grunting, groaning and crying but my balls finally rested against her asshole. I had buried my 7" cock in her tight virgin pussy. I pulled my cock out until the head was just in and saw her virgin blood on my cock. I pushed it back in and started to fuck her slow and long while taking more pictures.

"Oh, Oh, Oh, Oh my god, it's too big, I feel too full, please take it out."

"Melissa, just relax, you'll begin to enjoy it in a minute."

I kept fucking her and lifted her top and took her bra off and started to suck her 34A tits. She started to groan a different way; she was starting to enjoy the sex now.

"Mr. C, it's beginning to get better."

"That's good honey because now I'm going to fuck you hard."

I started to fuck her hard and fast, ramming it in and my balls were slapping against her asshole. I would take that hole next but now was the time to do her pussy.

"OH! OH! OH!" She cried over and over each time I slammed into her.

I was going to cum soon and I had a diabolical idea. What if I somehow got the condom off without her knowing? She's young and naïve and it might be possible. I decided to go for it so I put my hand down between us and pulled the condom off quick and put my cock back in. It only took a second. OH MY GOD! She was warm, wet and super tight and she didn't know I was riding her bareback now. This only brought me closer to an orgasm and I was starting to swell up in preparation of dumping a load of sperm in my babysitter's pussy.


I stayed inside Melissa while I came back to earth and she said "Mr. C, did you say that you came in my pussy?"

"I'm not sure how it happened but the condom came off and I didn't realize it until I was cumming in your pussy. I'm sure everything will be ok."

"MR. C, I'm going to get pregnant. I'm too young for this, my parents will kill me."

"Honey, it usually takes a lot of fucking to get pregnant, I wouldn't worry about it unless we fuck every day for a week straight."

I pulled my cock out of her pussy and we both watched the cum drip out of her blood stained pussy. I took a few more pictures of this beautiful sight.

"OK Mr. C you can fuck me all the time but you have to promise me that next time the rubber will stay on."

NEXT TIME!!! She wanted to fuck again! "I promise sweetie."

To be continued...