Cutter09

You Bet Your Ass

"Bullshit. Today's music is vulgar and crude. The lyrics are suggestive at best."

"Old music had suggestive lyrics too," I argued.

I was talking to our neighbor, Mr. Anderson.

"I bet you a hundred dollars I can name an old song with suggestive lyrics."

"First of all, you don't have a hundred dollars, secondly you're only thirteen, you're too damn young to know any old songs."

We were always arguing about stupid shit. We've made stupid bets before too. I had just finished mowing his yard for free because of one of our bets.

"So what do you want to wager?"

"My yard will need mowing again soon. Mow my yard four times against a hundred bucks. But you have to name two songs written before 1980. And you don't get any time to research it. Name them right here, right now."

"Your yard is huge, and you threw in two songs instead of one. In that case you have to sweeten the deal. A hundred dollars, and a blow job."

"Uh… A hundred and a blow job, against lawn mowing AND a blow job but then they have to be written before 1970," he stuttered.

"Why 1970?"

"That's the year I was born."

"Ok, you've got a bet," I said extending my hand to shake on it.

He looked at me suspiciously. "You seem too anxious. Let's make it a little harder. They have to be top 100 and came out in the same year."

"Shit. For that I want five blow jobs."

"I knew you couldn't do it. Ok, five it is." He was grinning from ear to ear. He thought he had me. Now he was the one holding out his hand.

I shook it.

"Let's see. In 1964 would it have been lewd for a woman to suggest living with a man for a year then she's in the wind?"

"Definitely, but there's no song like that."

"Sure there is, and most people know it because it's such a sweet, happy, tune."

"What?"

"We'll Sing In The Sunshine. Released in 1964. The lyrics say «I will stay with you one year, then I'll be on my way. It even says she takes whatever she can from him then she's history»."

He quickly googled the lyrics. "Son of a bitch. I used to love that song. I really never paid any attention to the lyrics I guess. But you still have to name another, and it has to be from 1964 now."

"That's easy. Hang On Sloopy. The lyrics say «let your hair hang down on me», then «Shake it shake it Sloopy. It feels so good.» What do you think it's suggesting?"

"Shit! I forgot about that song. You're right, I don't even need to google the lyrics."

Anderson pulled out his wallet and handed me a hundred dollars.

"Don't forget the blow jobs."

"You're not going to hold me to that, are you?"

"You're damn right I am. What thirteen year old boy doesn't want a blow job. Besides, if I had lost, you'd certainly expect me to get on my knees."

I didn't wait for a response, I unzipped and tugged my pants and underwear to my knees and sat on his sofa.

He stared at my four and a half inch [11 cm] hard on, subconsciously licked his lips, then got on the floor between my legs.

Anderson slurped and sucked and licked me for twenty minutes before I squirted my cum in his mouth. While he was busy, I took a couple of pictures with my phone.

"Same time tomorrow?" I asked as I pulled up my pants.

Anderson squeezed a large lump in his crotch and said, "Uh… Sure," as he licked a little leftover cum from his lips.

When I got to my room, I called my friend Mike. "You owe me fifty bucks and a blow job… Yes, I have proof."

The next day I was back at Anderson's. This time I got completely naked and sat on the sofa. Anderson was wearing boxers, and as soon as he saw me naked, a tent began to form in them.

He slurped and sucked a minute then got up and went to the bathroom. He came back carrying a tube of lube, and a huge tent in his boxers.

"What's that for?" I asked.

"Just something to make your blow job more enjoyable."

He starts sucking me again, and then I feel his finger at my butt hole.

As he pushes it in, I let out a moan. I had never played with my butt before, but his wasn't half bad. He began sliding it in and out, bumping something inside me that felt incredible. I lay back and closed my eyes, letting him do his thing.

After a couple more minutes, he slides in a second finger, and rubs that spot again, and I fire off like a volcano.

I'm still trying to catch my breath, when I open my eyes, and Anderson is standing over me jerking on his big cock. It had to be at least nine inches [23 cm]. He unloads all over me in torrents. I've never seen so much cum.

I could feel his eyes following me to the bathroom to get a towel. I got dressed, staring at his now limp but still big cock, lying on his thigh.

"See you tomorrow," I said.

That night, I had barely hit the bed, when my step dad comes in.

"Your mom's asleep," he says as he pulls off his underwear. He's got about seven inches [18 cm] of cock waving in front of him.

"Yesterday, Anderson bet me you'd let him finger your ass. Today he shows me a picture of you with two fingers buried in your butt. The way I see it, you owe me the two hundred you cost me."

He grabs me and holds my face into the pillow as he forces his dick into my ass.

By the time he gets all the way inside me, I stop struggling, and start moaning instead.

"You like it don't you. Well don't worry, I'll give you plenty. Your butt is much tighter than your mom's pussy."

I hate to admit it, but I did like it. He even made me cum on my sheet. Just as I feel his dick throb out his cum, the door burst open, and there stands Mom.

"You son of a bitch! He bet me a thousand dollars on our wedding day that you'd try something like this. Now get the fuck out of my house."

I had forgotten about that wager, it was a year ago. I'm glad Mom reminded me. But I was going to miss his dick in my butt.

The next day while my stepdad was getting his stuff out, I was at Anderson's. This time he used three fingers. It felt almost as good as my stepdad's dick.

I spent the night at Mike's house and got my blow job. He only had twenty dollars so now he owes me another blow job as interest. I was nice. I let him fuck me. His dick isn't as big as Anderson's fingers though, but he'll get bigger.

The next day as Anderson sucked me. I bet him he couldn't get his whole cock in me. I lost. Now he gets to fuck me the rest of the summer. I wonder what I can bet on when school starts.

The End