Chapter 1

When I was fourteen, my parents decided to take a long-dreamed of two week trip to South America. In all the discussions about their upcoming trip, it was decided early on that I would stay at home by myself during the time they were away and just have a neighbor keep tabs on me. Sounded fine with me, I was happy with that.

But, about two weeks before their trip, my mom decided that I was still a bit young to be on my own and that a neighbor's daughter who used to babysit me would be home from college and that it would be best if she stayed at our house while my parents were away.

So, I guess this all really starts back when I was ten years old.

My parents asked a neighbor's daughter, Kristen, who was fifteen at the time, to babysit me when they went out. She was really cute; I noticed girls even though I was still shy of puberty; I did get hard-ons and rubbed myself a lot, but didn't get much chance to do anything else.

Anyway, Kristen babysat for my parents for several years. I always liked having her babysit me and though we never did anything sexual, she did fuel my lustful imagination when I would jack-off. No, nothing really happened back then. Well, except maybe in my dreams and fantasies.

So, I wasn't going to be on my own after all and if I had to have supervision, at least it was Kristen and her being pretty was a bonus. It immediately fed my current fourteen-year old fantasies which, if harnessed, could power a small-sized city.

On the day of my parent's departure, Kristen came over with a small suitcase and a backpack and I was knocked out by how she looked. She was cute as ever, long, dark brown hair, smoothest, creamiest skin, I'd ever seen, pretty, pink lips, and slim with large, round tits pushing her college sweater skyward.

Oh, I thought, two weeks of whacking off dreaming about her around the house. I was going to be worn down to a nub. Oh, well, a happy nub.

The first couple of days were uneventful, except for my jacking-off every couple of hours thinking of Kristen sleeping in my parent's room just a few feet away from my room.

Kristen was cool, wasn't as strict as she used to be and told me that she had learned a lot being on her own and that I was old enough to pretty much do what I wanted to do.

About the third night, I was in my room, door closed, doing my homework (meaning, naked on my bed and jacking-off, actually), thinking about Kristen off at college, who she might be screwing, what she must be like in bed, just within a minute or two of a big cum, when Kristen opened the door to see if I needed any help with my homework.

She must have knocked lightly; if she did, I didn't hear her, my mind was on other important matters, and she must have stood there for a minute or so before I opened my eyes.

"Oh, shit!"

There was nothing nearby to cover myself with, I just lay there with a stupid look on my face with all the covers at the foot of the bed.

"Hey, don't worry about it, Justin, everybody does it. I told you you're old enough to do what you want to do. And there's really nothing wrong with masturbating. Actually, that's a good idea, I think I'm gonna go do it myself," and she turned to leave, paused and said, over her shoulder, "Um, would you rather I leave you alone or would you like to get off together?"

Remember, I'm a fourteen-year old boy. And, I've never had any form of sex with a girl, nothing, not even a good boob feel.

"Um, well, why don't you come in? Here, sit here, next to me," as I started rubbing myself again since she was so okay with masturbation and all.

"Do you do it a lot, Justin?"

"Um, well, yeah, some, um, quite a bit."

"Well, that's okay, so do I. Like several times a day, sometimes more if I'm really feeling horny."

"Wow, that's cool."

"It looks like that feels good, huh?

"Oh, yeah, really good."

"Do you think about certain girls when you do it? Like right now?"

"Um, well, yeah, um, I kind of do, yeah."

"Like who were you thinking of before I opened the door?"

"Um, well, it was, um, it was..."

She cocked her head and asked, "Me?"

"Um, yeah, and right now, too."

"Well that's a nice complement, Justin. I really like watching guys get off, it's really cool when they orgasm and shoot their cum. Especially young guys like you. They shoot so far. Are you close?"

"Um, I'm gettin' closer."

"You have a very pretty cock. Nice and long. Girls will love your cock. Have you seen a girl naked before?"

"Well, uh, no, not really."

"Would you like to?"

Again, a question that really needs no answer from a fourteen-year old boy who is on the verge of cumming.

She stood up, pulled off her top and stood in front of me in a pink, lacy bra. Then, she reached around and shrugged it off.

Her breasts, for a slender girl, were pretty large, they actually were wider than her chest and crowned with very pretty, pink nipples which were very pointy. She squeezed her boobs together with her hands and played with them a bit, kind of shaking them up and down.

"God, you are beautiful Kristen. You have the most beautiful boobs I've ever seen, even in Playboy."

"Aren't you sweet. They are nice and I love to play with them. And I love to show them off to boys like you who really appreciate them. This'll give you a lot to dream about when you get off."

She sits back down and takes hold of me and asks, "Would you like for me to do it? I love making guys cum. And I want you to cum so you'll last longer when you see my pussy."

Did I hear this right? Her pussy? Oh, my god, I've died and gone to heaven. I let her take over and the feeling is thrilling. Absolutely thrilling. Her soft hand is moving up and down as I almost faint from ecstasy.

"Oh, god, Kristen, that is so good."

"How's this?" she asks as she turns more toward me and starts using both hands.

"Oh, god, I'm really close. It's just ... oh, yeah, oh, yeah, EWWW, EWWW, eww, eww, oh, wow, that was the greatest. Oh, Kristen."

"Boy, your cum really shot far. I love it. Look, even on my shoulder and your chest. And my boob. Wanna lick it off? I'll make sure you squirt some more."

It's my own cum, but who cares. You should see the beautiful breast it landed on. So, of course I licked it off. Took my time, too.

"You can suck my nipples, I just love that. Mmm, just like that. Is it nice?"

"MmmHmm," I mumbled not wanting to let go for a second. She's still playing with my dick which is still pretty hard.

"Watching you cum has got me so hot, I've just got to get my fingers on my pussy."

As she stood up and unzipped her jeans and tugged them down, I scooted over to make room on the bed for her. My heart was about to explode right through my chest as she pulled off her panties and stood there in front of me.