Babysitting Adventure
 

It all started when I was asked to babysit Jane.

At the time, I had just turned seventeen years old and it was the spring term of my junior year. I was about five ten, kind of tall for my age, with a toned and tanned body from playing soccer, and black hair. I guess girls thought I was attractive, but I hadn’t really done much with any of them. Not that I didn’t want to, I was just shy. I when in the phase where all I wanted to do was buy video games, so when I heard Jane’s mom was looking for a babysitter I jumped on the opportunity to make a little extra cash. Besides, it wasn’t like it was even going to be that hard.

I had know Jane pretty much every since I was born, as our families were pretty tight. I had hung out mostly with Jane’s older sister, Emily, who was my age, but I still knew Jane fairly well. Jane was fifteen, with long blonde hair and was very cute for her age. She was not as developed as the girls in my grade, but she did have a nice ass and some breasts. Her sister – Emily – had pretty large tits, so Jane will probably also have some knockers in a few years.

When I arrived at Jane’s house at around five that Friday evening, I was greeted by Jane’s parents. They told me they were going out to dinner at a fancy restaurant two or so hours away, and as a result they would not be back until eleven. Emily was out at a concert, as she was the musical type, and that was why she could not babysit, although they did not know when she would be getting back.

They also sprung a surprise on me. Jane was having friends over, two to be exact, who would be spending the night. This was not exactly what I had been expecting, as it would make my job harder. But before I could complain they shoved twenty dollars into my hand for pizza and left.

I went into the house and called Jane’s name a few times before she appeared at the top of the staircase. She was followed by two girls her age, who she immediately introduced to me. Rachel was the shorter one, with dark hair and a cute face. She had pretty large breasts for her age, and nice ass too, both of which were bigger than Jane’s assets. She was also fifteen, a little older, while the other girl was only fourteen like Jane. Her name was Carly, and she had dirty blonde hair. Her breasts and ass were small, but she made up for it by being the prettiest of them all. While Jane and Rachel were cute, Carly was gorgeous.

They were all dressed in their soccer uniforms, as they had just gotten back from a game, which they had won. I asked them if they were hungry already, and they said they were. We decided to order two large pizzas from Luca’s, a local place that delivered. The people at Luca’s said it would take about thirty minutes for the pizzas to get here, so I asked the girls what they wanted to do. They all said they needed to take showers and get cleaned up, so they headed upstairs to do so. Meanwhile, I sat down in front of the TV and turned on a sports channel, satisfied so far with how easy this job was.

Very good start, I am so much looking forward to read more :-)

You have a good writong style, will be interesting to see how this story progresses. Good that it's taking its time. Good effort!

I'm very interested keep it up its good.

Amazing Start can't wait to read more!

write more write more

Thanks for all the replies!!!!!!!
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The girls came back downstairs about fifteen minutes later, having taken fairly quick showers. They had changed too, and they all looked very nice. Jane was wearing black yoga pants that accentuated her curves, and on top she was wearing a plain white t-shirt. Rachel had on jeans and a blouse, which was cut low enough to reveal some cleavage. Carly had on a pair of white khaki shorts, which showed off her long tan legs, and a black tank top on top, which revealed not only the straps of her red bra but also some cleavage.

Luckily for me, the girls all enjoyed sports so they didn’t care that I still wanted to watch the baseball game, and they watched it with me. I could sense them getting bored after a minutes though, so being the kind babysitter that I was I asked them if they wanted to change channels. They said no, the game was fine, but my question sparked some conversation and after a few minutes of talking about school, sports, and love, it was Jane that asked the question.

“Soo… you guys want to play truth or dare?”

The other girls squealed excitedly and looked at me.

“Do you want me to play too?” I asked a little incredulously.

“Of course!” they all yelled.

I shrugged and said sure, as even I was getting a little bored of the baseball game.

I love it! Can't wait for more!

Jane started it off by asking Rachel, who chose truth. “What’s the farthest you’ve gone with a boy?” she asked.

Rachel explained that the farthest she had gone was just making out and then the boy had briefly groped her breast. She then turned to me when she was done explaining this and asked, “Truth or dare?”

To be on the safe side I chose truth, and she asked me if I was still a virgin. “Yes,” I replied a little embaressed, but no one said anything to make fun of me.

I then turned to Carly, the only one not involved yet and asked her. She chose truth. “What size breasts are you?”

“22 B,” replied, and was about to turn to ask Jane when Jane interrupted her.

“Alright this game is almost as boring as the baseball game… lets make it more exciting! How about you can’t choose truth twice in a row?”

The girls all nodded so I just shrugged in agreement. Satisfied with the new rule, Jane turned to Carly who asked her, “Truth or dare?”

“Dare,” said Jane boldly.

“I dare you to take off your t-shirt, turn it inside out, and then put it back on.”

Without hesitation, Jane whipped off her shirt revealing her nice breasts, which I knew to be a 26 B, which were covered in a plain black bra. She then flipped her t-shirt inside out and quickly put it back on, in order to cover up as quickly as possible.

Now, although I had known her for my whole life, and although she was two years younger than me, I felt myself staring at her breasts when they were exposed. Don’t take this the wrong way, I had no desire to fuck her - yet -, but she was hot and very attractive. I was a teenage boy, raging with hormones, who, by the way, had not masturbated recently, so I was very attracted to this pretty girl in front of me. Anyways, I didn’t have a lot of time to reflect on how weird it was that I was attracted to her because she turned to me and asked, “Truth or dare?”

“Dare,” I replied, although I didn’t really have a choice because of the new rule.

Jane smiled and responded, “I dare you to…..”

I can't wait to read more, please continue.

very good so far looking forward to more.

That was great! can't wait for more!!

It's really good so far! Keep writing!

Thanks for all the replies! It makes me feel like my writing is worth continuing, so keep it up plzzzz


Jane smiled and responded, “I dare you to take off your shirt for the rest of the game.”

I groaned, but without much hesitation took off my shirt. I kept myself in pretty good shape so I nearly had a six pack and had nearly no body fat. The girls all gave me mock wolf whistles as I stripped off my shirt, and I just grinned. When it was off I turned to Rachel and asked her, although she didn’t really have a choice as she had just chosen truth.

After she said dare, I responded. “I dare you to lick your toe.”

Everyone just stopped and looked at me. “What kind of dare is that?” exclaimed Jane.

“What do you mean?” I asked.

“That might be the lamest dare I’ve ever heard of!”

I blushed. I knew it was an awful dare, but honestly I didn’t want to give any dares that were even slightly sexual. I was suppose to be the babysitter and I was suppose to be the responsible one. I told them this and Jane just laughed.

“Listen, we’re all basically the same age. We just want to have fun tonight, not be bored and responsible. So please just play with us as if we were just chilling and having fun.”

I thought about this. I guess she was right, as long as she didn’t tell her parents then there was no way they could find out. “Fine,” I said, “Rachel, I dare you to take off your blouse and leave it off.”

Everyone cheered and exclaimed that I had given a good dare at long last, even Rachel, who then proceeded to strip off her blouse and reveal her rather large C 22 breasts that were just barely held in place by a light blue bra. She did not blush at all while doing this, leading me to believe that this was not her first time being so adventurous.

Rachel then turned to…

I really like this. Keep up the great work. How old are these characters supposed to be?