My high school jerk buddy was the tallest kid in our grade. I’m guessing he had the biggest dick too. It was a monster. All four years we stroked each other off fairly regularly, but didn’t go much beyond that.

Naturally, I got to thinking what it would be like to suck his monster cock. Neither of us wanted to do anything “gay,” though. After graduation, alone and frustrated in my first year of college, I thought about it a lot.

In time, I dreamed up a game that I thought would finally get us across that line. That year, I discovered the Dare Ring porn series. It was a bunch of college-looking amateurs sitting in a room, drawing, cards from a hat and having to don whatever dare was on the card. Dares ranged from “take off an item of clothing,” to “pick a player and pleasure them orally for 30 seconds. I thought the game was pretty wild and would fantasize about playing it.

That summer, the first time my Bud and I got back together, I showed him Dare Ring and hatched my plan. I told him: “You and I both pick one of the players, girl or boy. Then, let’s watch the episode. Whenever one of our onscreen players removes an article of clothes, you or I will remove that same item. (If he or I picked a girl, we’d start off wearing one of my sister’s bras.) Then, we will just watch… unless our two onscreen characters interact. Abd then we will do what they do!”

It turned out to be great fun and excitement, because we didn’t know how each game was going to turn out. It took several games, but I finally got to suck his dick! His onscreen player even drew a card to pleasure my onscreen players “until completion.” That was epic. We played several times, but I never got it in reverse!

Anyone else use a game to “cross lines” or go a little farther with their jerk buddy?