Have any of you had one of those days that changed your life forever? I have. It was a Tuesday, if I remember correctly. It started at high school. Well, actually it didn't, but to get the whole picture I need to start there. It was lunch break, and we were all outside. And there she was. Jennifer Graston. Her hair was shining in the sunlight, a blonde ponytail waving back and forth as she moved her head. She was wearing pink again; she always wore pink, and she had her glasses on, the ones that were small, demure, and adorable. Just like her. And here I was, some guy that didn't exist to her. She wasn't ignoring me or being a bitch, it's just that I hadn't gotten the guts to approach her yet. Or at least, I hadn't until now. That's why I was standing on the other side of the courtyard at school during lunch, staring at her talking with her friends and rubbing my sweating palms on my shirt. I'd hoped to talk to her alone, away from her friends, but that was never going to happen. So it was now or never, and I moved in.
I only got about halfway across the courtyard when I tripped over something, and hit the ground hard. It was a harsh bellyflop that left me winded and gasping for breath. As the ringing in my ears faded away I became aware of people laughing, and looking up, I could see them. Everyone was looking at me, laughing. Even Jennifer, the beautiful angel of my dreams, was giggling and covering her mouth with her hand. One person's laughter louder than the rest, and was very close by. I looked up to see Bonnie standing over me, laughing her ass off.
"Did you see that?" she screeched to her friends. "I can't believe how easy it is to trip you up. You fall for it every time!"
I hate Bonnie. She was the biggest bitch in school, casually cruel and vicious to everyone and anyone. But in particular she seemed to have a grudge against me. I don't know why.
I picked myself up and managed to limp off somewhere quiet, but before I could find a place to rest for a bit, the bell rang, and lunch was over. Great. For a moment I contemplated skipping class, hiding behind the gym and just doing nothing for an hour until the next class, but common sense prevailed, and I made my back to the classroom. What did it matter anyway? This was already turning out to be the worst day ever.
Boy was I ever wrong.
The rest of the day was an unfocused blur of the teachers' voices, staring into space and riding the bus. I was doing my best to just let the time go by as quickly as possible until I got home. When I did I was finally able to relax. I dumped my bag by the door, kicked off my shoes, and made a beeline for my room.
"Another tough day at school, Danny?"
My dad was in the living room, on the couch. His face was filled with genuine concern, but I didn't want to talk about my day. It was just more of the same anyway, so I told him so.
"I'm just going to go to bed, dad." I said. "I just wanna sleep right now."
"That's ok kiddo. Sandra and I are going on another date tonight, so Kelly's coming over to make sure you stay out of trouble."
He smiled as he said it, and I laughed. He knew that I always stayed out of trouble.
"Well enjoy your date, dad." I said as I went upstairs.
It was just me and my dad at home, ever since my mom died in a car accident when I was five years old. Ever since then my dad had gone into survival mode. He'd sold the house for a smaller, cheaper one. He'd starting working longer hours to earn the extra income to make sure that we had enough money for, well, everything. It was only recently that Sandra had come along to remind him of what he'd been missing in that time, and hadn't even dared to think about. Intimacy with a woman. I was happy for my dad at finally moving forward and thinking of himself for a change, instead of thinking of work and taking care of me. However, him being out with Sandra meant that he needed a babysitter, and that meant Kelly.
It's not that I minded Kelly. In fact I liked her, she was nice, friendly, and pretty cool to have babysit. There were two things that bothered me about her though. First was that I was sixteen, and in my opinion a little too old to need a babysitter. It's not like I'm a baby, right? Second, Kelly was kinda hot, in an average girl next door kind of way. Not that this was a bad thing, per se, but it was just that I couldn't do anything about it. I had no idea how to go about getting her into bed, and I was afraid that if I tried she'd get upset, and never come back. That would also mean my dad would have to find someone else, and I didn't want to cause him another headache because I was being an idiot. Instead I just fantasized about her in the privacy of my thoughts. And in my bed, in the shower, and even in the bath when the mood takes me.
I made it to my room, locked the door, and stripped down to my boxers before climbing into bed. I had a couple hours before Kelly would show up and make dinner, so I knew that I could afford to get some sleep beforehand. I lay on my back, closed my eyes, and tried to sleep but it just wouldn't come. I found myself thinking of Kelly again, and as I did, my cock was starting to swell. I rubbed the growing hardness through my boxers as I thought about her. She was a few years older than me, and was a curvy woman. She wasn't fat, just. . . cuddly, a little bit of extra padding, as I like to call it. She had wide hips, with an ample ass to follow. Sometimes all it took for me to get an erection was for her to turn her back on me, and her ass would just fill my vision. Perhaps I had a thing for big asses, or perhaps it was just Kelly, I couldn't tell. Either way, her ass was awesome, and I enjoyed picturing it presented before me as she would get down on all fours, begging me to take her.
My dick was truly hard now, and I slipped my hand under the waistband to take it in my hand. I was quite proud of my own dick. I'd done some research on the subject, and while I found that it may not have been quite as long as the average, it was certainly a thick one. I visualized the swollen head of it poking against Kelly's moist pussy lips as she lay her face down on the carpet with her ass up in the air. I pictured it sliding inside her, all the way, until her ass cheeks were pressing against me. That image alone was enough to fire me up, and I was jacking my hand up and down my cock furiously, just picturing her back sloped in front of me, and her hands squeezing fistfuls of the carpet.
"I can see you're busy."
I practically screamed as the voice spoke, and I sat bolt upright, pulling my hand out of my shorts so fast I could have pulled my dick right off. I looked up to see someone standing at the foot of the bed, a guy wearing an old fashioned suit with coat tails, it was an eye-smarting shade of red, and he was smiling at me with a knowing smile. I had no idea who he was or what the hell he was doing in my room. Why was he standing there watching me masturbate?
"What the fuck are you doing here?!" I yelled, surprised beyond belief. "Who are you?"
He didn't seem to be embarrassed or even worried that my dad would hear me yelling. He just smiled again, and casually walked around the bed.
"You don't have to worry about me watching you, I wasn't here long, and while I may be a bit of a perv, I have standards."
"What the fuck is going on!?" I screamed. I couldn't handle the fact that there was a stranger in my room, watching me get off. I was getting hysterical. I started screaming for my dad.
"Just calm the fuck down, would you?" he said. "Your dad can't hear you, no one can, I've taken care of it. I'll answer your questions, but you need to give me a chance alright? Besides, I guarantee that I have something for you that you want."
That got my attention, and I settled down a little bit. He seemed satisfied and sat down on the edge of my bed. I pulled my covers up to cover my half naked body, and he just laughed.
"Relax. You're not my type. I'm into girls, just like you am I right?" he said, and raised an eyebrow.
"Well. . . yea."
"Of course you're into girls, how could you not be? They're awesome! They're so soft and warm, and they curve in just the right places to drive men wild."
"Point, please." I said. I was still uncomfortable, and him talking about girls like a horny pervert was not helping things.
"Right, right. You're probably wondering who I am and whatnot. Well first of all I'm not entirely real."
I blinked.
"What the hell does that mean?" I asked. He responded by disappearing in a puff of smoke to reappear again, only now he had his legs hooked over my hanging ceiling light, so he was upside down looking at me.