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It takes two people to baby sit three girls, one of which is a baby.
Fbailey story number 719

My Sister And I Babysitting

My sister and I have always been close. I had been looking for a way to earn some extra money when my sister suggested that I help her baby-sit. She promised that I would not have to change any diapers as long as I helped out by getting bottles ready and playing with the children. She had tried babysitting once and it was more than she could handle. Mom had suggested that she find a girlfriend to help but none of her friends wanted to spend their Friday and Saturday nights babysitting snotty nose kids.

My sister Kendra was thirteen years old at the time and I was fourteen years old. She was a really sweet girl. Mom felt better having me with Kendra because Mom was afraid that someone might take advantage of her. Apparently Mom had had a few close calls when she was a teenage girl babysitting. Husbands come home drunk or grabbed at her taking her home.

Our first job was for the Smith’s three kids. They promised us fifty dollars for six hours work. They were going to his boss’ house from six to midnight. Then they wanted us there at five o’clock and said that they might be late coming home too. Kendra negotiated for ten dollars an hour up to midnight and then fifteen dollars an hour after that. They agreed.

We arrived a few minutes early and found that they had a four-month-old baby girl, a two-year-old girl, and a three-year-old girl. Their bedtime was six-thirty except the baby wakes up about every hour to get milk…mother’s milk. Mrs. Smith had some frozen and told us how to thaw it and then warm it in hot water. She explained about the temperature and then she nursed the baby before she left.

Kendra and I were sitting there when she pulled her dress straps off her shoulders and then pulled her top down below her breasts. I had never seen a woman topless before but she didn’t mind at all.

She saw me staring and said, “I’m not shy about feeding my baby. I went threw it twice before. I even do it in public. I don’t usually take them both out if there are other men standing around but you are going to be babysitting for us often…I hope.”

Kendra asked, “If we do a good job, you might hire us again?”

Mrs. Smith said, “Yes dear, perhaps every weekend if all goes well tonight. You see this is a very important dinner party. My husband is up for a promotion.”

She let the baby suckle on one nipple and then changed her over to the other one.

Mrs. Smith noticed my look, giggled, and then said, “I have to even them out. I wouldn’t want one of my breasts to look larger now would I?”

When she was finished she stood up and handed the baby to my sister.

She then turned to me and said, “Would you like a taste? Then you could see how warm the milk in the bottle should be.”

My mouth was open and before I knew it she had pulled my face to her breasts. She put her big nipple in my mouth and told me to start sucking. In the corner of my eye I could see my sister watching me. I wasn’t sure if I would ever get another chance like that again so I started sucking. It was warm and it tasted good. Soon she told me to suck from the other one to even her out again.

Just as she pulled her dress up, adjusted her shoulder straps, and bounced her breasts around a little her husband said, “Come on I don’t want to be late.”

After they left Kendra asked, “What did it taste like? I wish she had let me taste it.”

I tried to explain to her that it was like warm cow’s milk, only it was a lot more fun drinking right from her nipple.

Kendra lifted her shirt up to her neck. She was not wearing a bra either. Then she touched the baby’s lips to her breast and it latched on right away. She smiled and said, “That feels nice. I always wondered what it would feel like to let a boy suck my nipples.”

I stepped closer, bent over, and sucked her other nipple into my mouth. The baby gave up soon knowing that no milk was coming out of her breast. I didn’t give up that easily and my sister liked it. She almost dropped the baby when my hand rubbed against her panty-covered pussy so I stopped and started playing with the older two girls. They were into Lego’s, Thomas the Train, and Dora the Explorer. They had been fed before we got there so it was just an hour and a half and we put the two older girls to bed.

The baby went down too but we knew that wouldn’t last. Her crib was in the parent’s bedroom and there was a baby monitor.

For the next hour Kendra sat on the couch with her top off, I lay across her lap, and suckled on her small firm breasts until we heard the baby cry.

I fixed a bottle and she changed its diaper. Kendra didn’t put her top back on. After we fed the baby she rocked it to sleep and then put it back in its crib.

That time my sister let me feel her pussy but she wanted to keep her panties on and my hands out of them.

After the next feeding she let me get my hand inside her panties and we both enjoyed that a lot. Just as Kendra was having an orgasm the damn baby cried and she jumped up and ran off telling me to get another bottle ready.

That time after she put the baby to bed Kendra removed her skirt and her panties to remain nude for me. She allowed me to do anything that I wanted to do…except…put my cock in her pussy or in her ass.


Other than being disturbed by the baby crying I spent the next few hours kissing my sister, sucking her breasts, and feeling her pussy. A few times I licked her pussy until she had an orgasm. Twice she let me cum in her mouth. I liked it and she seemed to like the taste.

About two o’clock in the morning the phone woke us up. It was Mrs. Smith telling us that they were on their way home and that they were sorry for being late.

That gave us time to get dressed.

Mr. Smith just went straight to bed. He was drunk. Mrs. Smith handed Kendra one hundred dollars and thanked us for babysitting.

Kendra boldly asked, “Can I suck on your nipples? I want to know what it is like.”

Mrs. Smith smiled and asked Kendra to unzip her dress. Kendra got behind her and unzipped her dress. Mrs. Smith let it drop to the floor and then she stood there in a very sexy pair of red thong panties. She pulled both my sister and I to her bare breasts and let us suck.

I had been sucking my sister’s breasts all night and felling of her pussy so my hand just naturally went to Mrs. Smith’s pussy. She didn’t object so I slipped my hand into her panties and started to tickle her clit. She moaned and asked if we could continue on the couch.

Kendra hadn’t noticed what I was doing until I sat down next to Mrs. Smith and slipped my hand back into her panties. Mrs. Smith lifted her butt and slipped her panties off for me. I went right down to taste her pussy and I liked it, it was strong, and it tasted great.

Mrs. Smith looked at Kendra and asked, “Do you want a taste of that too?”

Kendra smiled and took my place between Mrs. Smith’s legs. We took turns sucking her breasts, licking her pussy, and kissing her face. Kendra was having just as much fun as I was.

Mrs. Smith asked, “Do you let your brother fuck you?”

Kendra blushed and said, “Not yet. I let him do everything but fuck me tonight after the girls were in bed.”

Mrs. Smith asked, “Are you both virgins?”

We nodded our heads yes.

She asked, “Would you rather he be a virgin the first time that he fucks you or can I let him fuck me first?”

Kendra said, “He can fuck you first…besides the other girls say the boy is a lot better the second time in one night.”

Mrs. Smith laughed and said, “Yes honey, boys do last longer the second time around and the third and forth time too. Can we take turns wearing him out?”

Kendra said, “Okay.”

So Mrs. Smith scooted closer to the edge of the couch and opened her legs wider for me. She even helped me get my cock in her hole. After that she just let me pump away until I had cum in her.

It felt great being inside her. She smiled and she encouraged me to keep going. After I came in her she thanked me.

Kendra sucked me hard again even though my cock had been in Mrs. Smith’s pussy. Then I realized that her tongue had been in Mrs. Smith’s pussy too so it really didn’t matter.

Then Kendra got on the edge of the couch and spread her legs for me. Mrs. Smith helped guide my cock into my sister’s pussy. I did last longer and we both enjoyed it. It was actually my forth time to cum so it took long enough for Kendra to have an orgasm.

Mrs. Smith said that it was quite unusual for a virgin girl to have an orgasm her first time out.

Then Mrs. Smith and Kendra got into a sixty-nine with Kendra on top and my fresh cum dripping into Mrs. Smith’s open mouth.

We got dressed and walked home.

We babysat every Saturday after that and sex with Mrs. Smith was something that we both looked forward too. Mr. Smith got his promotion and got drunk every Saturday with his boss and coworkers.

Mrs. Smith told us that her husband and she had foursomes with other couples at those gatherings.

A few months later she told Kendra and I that she was pregnant again. She also said that she had no way of knowing who the father was. I never used condoms and neither did the other eight guys that got to fuck her.

I had never been more thankful that Mom had gotten Kendra on birth control.

Mrs. Smith was only thirty years old and the prettiest woman that I knew…and I might be the father of her next baby…I might get to watch my own child grow up. Wow!

The End
My Sister And I Babysitting


2017-12-02 18:20:23
What an awesome introduction to sex.

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