Lost The Bet

My father left us when I was ten. He was a nasty fuck, so while it was tough financially (which I didn’t understand then), it was for the best. My Mom worked long hard hours, and I brought in an extra twenty or thirty bucks a week doing odd jobs with my friend Sal.

Anyway, when I was thirteen my Mom met this guy Chris, who was pretty cool. He had a son named Jason. Jason was two years younger than me and was a real pain in the ass. A year later they were married and Jason moved in.

I used to kick the shit out of him. All the time. I was mean, aren’t all big sisters?? When they weren’t home I’d make strip him and make him do things around the house. I actually got excited sometimes watching his scrawny pre-teen nakedness wander around cleaning (I loved to dump water on the kitchen floor and watch him on him scrub it naked on his hands and knees).

Why didn’t he tell on me? Because he was always in real deep shit, and what I did to him was nothing compared to how his father handled his actions. So Jason was always willing to do as I wished. By the time I was sixteen, he had learned to eat me, and he kept his entire body shaved.

It was the summer of my seventeenth birthday that things turned around. Jason met a girl and suddenly started to behave himself a little more. I only got to use him maybe once or twice every couple months. Anyway, I eventually turned eighteen and moved away from home to college.

My Mom called often and told me that Jason was back to his old antics and they had thrown him out. He even called me and we got into a blowout of a fight which led to the bet. I told him he was a useless piece of shit and that he was never going to amount to anything.

This really pissed him off. He bet me he could get a job, any job, and keep it for six months. I laughed at him, saying “Yeah, I fuckin’ bet.”

He called me on it. “I’ll bet you that I can get a job, and a place, and keep the job.”

“Ha! For how long?”

“I dunno… Tell me.”

“Six months. I’ll believe that you turned your act around if you can get a job and keep it for at least six months. But if you lose, it just proves your the useless piece of shit that you are.”

He grunted, “Yeah, and what do I get if I win?”

There was silence for a few minutes. A heavy silence.

“What do you want?” I asked.

His voice changed, “I want you for one day. You will have to do whatever I want.”

“Okay,” laughing, “if you do it, I’ll be your slave for a day. Fair?” It sure sounded that way to me, this guy never kept a job over three days!!

“Deal.”

“Deal,” and I hung up the phone. I hadn’t heard from him again until the last week of the following April. I got a package in the mail. I opened it. There was a letter with a bundle of paper banded together. I lifted the note and looked at the bundle. It was xerox copies of tons of paychecks. With Jason’s name on them.

I flipped back to the letter.

Lisa,

Here’s the proof. Six months of paychecks and a copy of my lease. I’ll see you at my place on the 14th. 8 a.m. Wear only pants, sneakers and a jacket.

Jason

I couldn’t believe it. Shit! I went through every check, and even checked out the lease. It was him. All of it. Wow! Somehow, the thought of being at his mercy was strangely exciting. And the 16th, that was this Saturday!

That Friday, I finished my classes and practically ran back to my dorm room. I packed (lightly of course) and headed home. Mom and Chris were happy to see me and of course wanted to know what I was doing home for the weekend. I told them I missed being there, that seemed to work.

We had dinner together that night and they told me how much Jason had turned around. He was responsible, and working hard. ‘All this for me?’ I wondered. It was almost flattery! Would it last past Saturday? For how long? Why?!?

I could barely sleep that night. Mom tried to call Jason, but he wasn’t home (just not answering the phone I guess).

The next morning, I got up and out of the house before anyone was stirring. Dressed as he wanted. It was pouring out. I pulled into the driveway of the place he was staying. It was a huge victroian house with many apartments in it. I parked and took a deep breath. I got out and walked around to the back door (the one with his apartment number on it).

There was a note that told me to go to another apartment. I walked back around to the front of the house and knocked on the door. I was just getting ready to leave when the door opened. I was greeted by some sixteen year old kid in his underwear, his cock hardening as he looked me up and down. His hair was standing up on end and he looked as if he had had one pretty wild night.

“Yeah?”

“I’m here to see Jason. Is he home?”

He shrugged, “I dunno… Think he’s sleepin’ upstairs in his room.”

He just stood there and looked at me. “Well, I’m his sister. Can you let me in?”

He shrugged again, “I don’t give a fuck,” I started to walk in and he stopped me. “Take off your shoes, girl. Don’t get the floor all wet.” I wasn’t sure what to do, but I took them off. I put them next to the matt with about ten other pairs of shoes and sneakers. He stepped out of the way and I went in.

He pointed down the dark hall, “Up the stairs.”

I walked down the grungy hall. From the feel of what was under my feet, this place hadn’t been swept in about ten years. I walked down the hall and up the stairs. I found his door and knocked on it. There was some banging inside and the door finally opened. He smiled when he saw me there.

“Hi,” he said sleepily.

“Hi Jason. Here I am.”

He stood in the doorway and looked me over, “Where’s your shoes?”

“I had to leave them at the door.”

“Okay. Get undressed.”

I looked nervously up and down the hall and did as he said. I unzipped my coat and took it off, my nipples hardening from excitement as I dropped it to the floor. Then I reached down and unbuttoned my pants, unzipped them and pushed them to my ankles, slowly stepping out of them. My pussy was aching and pulsing as I stood naked in front of him in the hallway.

He stepped back and motioned me in. I started to pick up my stuff but he stopped me, “No, leave it there. You won’t need your clothes in here.”

I went in and he closed the door. “Go stand in the middle of the room, hands behind your head.” I did as he said. He walked up behind me and kicked my feet apart. He stood in front of me and I watched as he took off his shirt, sneakers and socks, stripping down to his cutoffs. He still had a great build. Five-four and rock solid. I was amused to find that his body was still shaved (or at least what I could see of it).

He knelt on the floor behind me, “You know,” he said as he placed his hands around my ankles, “I’ve waited for this for a long time.” His hands slowly moved up and down my legs as he talked, moving closer to my aching vagina. “The day when I’d own you.” His hands moved to my inner thighs, occasionally palming my mons and gently squeezing. I was panting, the excitement of what he was going to do getting the best of me.

He was driving me nuts! I was so hot that I thought I was going to cum just from having my thighs and pussy rubbed!!! He must have sensed how close I was because he stopped and got up. He walked over to a closet and took something out. My jaw dropped when I saw what he came back with. It was a paddle that I used to beat his bare ass in front of a friend of mine.

Smiling he said, “Bend over and hold your ankles.” I did as he said and he started on me. I yelped and he told me to shut up. The pain was searing, but he would hit me two or three times and then rub my ass, legs and pussy, my excitement numbing me. He would get me to where I was just ready to cum and then whack me again.

He only hit me about twenty times and then told me to kneel. I did as he said and was my ass hot!! I put my hands behind my head again, just like I used to make him do. He walked over to the couch and sat down.

“Come here.” I got onto hands and knees and walked over to him, kneeling at the spot he pointed to between his legs. He took his barefoot and started to slowly run it down my chest, stomach, and then to my pussy, his toes slipping between my lips. I trembled and bit my bottom lip, closing my eyes as he wiggled his toes.

He stopped, “You a little horny?”

I nodded.

“Hmmm… I bet you are.” He took his foot off me and I groaned. Jason stretched out and smiled at me, “Satisfy me,” was all he said, his hand pointing at the swollen crotch of his shorts. I leaned forward and undid his pants. His huge cock sprung out and bounced in front of my mouth. I was so fucking horny I couldn’t stand it.

I took his cock in my hand and opened my mouth to take him in. I felt his hand on the back of my head as I gently closed my lips around him and started to suck, his strong hand urging me to take him deeper. He entwined his fingers in my long hair and worked my head up and down his cock as I stroked with my hand.

I didn’t think it possible, but his cock was still getting harder, not really longer, but harder and harder.