[Pineappled]

I closed my bedroom door behind me, as I turned around I noticed Stan had his back turned to me. His arms were in front of him and he was on his toes. “Dude, what are you doing?” I asked. He turned around, which answered my question.

As he was massaging his growing erection he told me, “I’m going to need this for your dare.”

I think I lost my breath at that point. What?!? What would he dare me that he needed a full erection for? What did I get myself into?

He went to my desk and rummaged around for a little bit. I didn’t dare ask what he was looking for. “Bingo.”

He turned around at full mast and presented a ruler. “My next dare is for you to measure. I’ll measure to, as a sign of good will.”

It wasn’t a sign of good will, we both could see he had a bigger dick than me, he just wanted to prove it because of that stupid remark I made.

I put the ruler up to my mostly erect penis. He read it aloud “Only 5 inches. Thats not as bad as I thought!”

Well, it wasn’t fully erect, but I don’t think that will add on too much more. I just wanted to get this embarrassment over with. I handed him the ruler. “Oh look! 7 inches! Thats way more than I thought.” Stan had his trademark grin.

I think I need to knock him down a peg. “I have an idea.” I said to him. “Lets change this up a little.”

“Oh yeah? How so?” he asked.

“Well, you like to gamble right?”

He nodded.

“Well, how about we play some poker?”

“Uhh, okay. I don’t have any money.”

“It won’t be for money.” This time I had the grin. “It will be for dares.”

The confusion on his face was priceless. “I don’t understand. How will we gamble dares?”

“Easy. We will play 3 rounds. You write 3 dares, of increasing difficulty and assign them levels. For example a level 1 dare would be: Dare the other person to do 5 push-ups nude. And then a level 2 dare would be something slightly more difficult. Understand?”

“Uhhh…. Kinda. So we are writing dares for the other to do?”

“Right. If you lost the first round after you bet that dare then you can’t dare me that, but I dare you that, along with the dare that I had bet.”

He was still confused. “So, lets say I lost my level 1 and 2 dares to you. I only have 1 left. Whats that worth?”

“Uhh… I can bet you any value of dares that equal that number or more. So I can bet you my level 3 dare, or I can bet you your level 1 and 2, or any combination that equals 3.”

“So if level 3 is the most important dare,what would a level 3 dare be?”

“Anything, that will be the most difficult dare you can think of.”

“Alright, that doesn’t sound too bad.”

“But there is a downside to making the dares too difficult.” I said with a slight excitement in my voice. “If you lose every bet, in theory you will have to do 6 dares. All 3 of mine, and all 3 of yours.”

He nodded. His face was honestly pondering the idea. “If.” He grinned.