All posts by Jack

Roommate Tickle Wager: Craps You Lose

By Jack

My roommate Zack and I, just before he moved back to the midwest to a different college, used to hang in the living room, drinking sherry (of all things) and shooting craps. We were way into it, and would have some fierce, marathon games, sometimes lasting until dawn. We sorta played by Hoyle, but some rules we made up as we went along. We were very competitive, really rubbed it in when the other guy lost. Zack was especially sadistic when I lost, calling me a wuss and a loser and stuff. We played with stacks of nickels, and the game was over when one guy won all the other guy’s nickels.

Now, Zack is very ticklish, but only his armpits. He is a muscular, wiry guy, 5’8″, 150#’s, smooth, clean-shaven, real handsome, with several tats. Very tough, hot, macho little 24 y.o. dude. Smooth, muscular chest, light wisps of blond hair in his armpits. Hated being tickled. No, I mean really HATED it. Used to tell me horror stories about his baby-sitter tying him up with electrical cord and tickling him until he pissed himself. Also, about his mother and older sister pinning him down with his arms over his head and tickling his armpits until he was screaming and crying. I listened to his stories with mock dread, and always seemed to feel sorry for him. So, yeah, I knew he was ticklish. And I knew he hated it.

But I also knew what a prick he was when I lost to him at craps.

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Roommate Tickle Wager: Arm Wrestling

By Jack

One of my recent wagers was with my buddy and roommate Rick. Unfortunately, I’m afraid I stacked the deck against him, and I feel just terrible about it.

We always used to hang out around the apartment drinking, playing cards, horsing around, bull shitting. Rick is a well-built, masculine guy, a carpenter, like me, with an in-your-face cocky attitude. He is about 5’9″, muscular, 160 lbs., with size 9.5 feet. He also shared my interest in bondage devices, and we had even tied each other up a few times. Nothing major, just Ha Ha, You’re tied up, now let’s do something else. Being straight, there was never anything sexual involved with Rick. But the last time he had me tied up, he used my handcuffs, some chain and padlocks to get me into a very tight hogtie. He was none too gentle with the cuffs, and they dug into my wrists real painfully and cut off the circulation, which didn’t seem to faze him, despite my protests. I plotted to get a little revenge for that.

I knew from horsing around with him that Rick was very ticklish, especially his feet and pits. And he HATED to be tickled. I had never mentioned to him my interest in bondage and tickle torture, so he never suspected a thing.

Late one night, after knocking back several Stoli martinis each, and several games of cards, he started to get rowdy and run off at the mouth about what a tough stud he was. The time was ripe.

I challenged him to an arm wrestling match, loser to get tied up. He was drunk enough and cocky enough to accept.

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Elevator Tickle Attack

By Jack

My buddy Jon and I used to work a retail job together. During one holiday season, we were working a gift fair in a large corporate office building down in the Financial Center. The merchandise was set up on tables, and we were using an SE/30 as a cash register and inventory control machine.

At night, we could just cover the merchandise with drop cloths, but we had to pack up the computer into a box and lug it up to the 33rd floor, to be locked in an office overnight.

This particular night, Jon offered to carry the boxed computer up, while I was in charge of the cash box (pretty lightweight).

Now, Jon is in his early twenties, a very clean-cut and handsome guy. He defines the term “jock”: extremely muscular, athletic, short brown hair, cocky attitude, very dry, deep voice.

When we entered the elevator up to the 33rd floor, it was well after 5:00 pm. No one was heading UP at that hour, so we were alone in the elevator. As I looked over and saw Jon struggling with holding that heavy box (easier to just hold it rather than to put it down on the floor of the elevator and then have to pick it back up again), I all of a sudden felt a mischievous streak rising in me.

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Racked and Tickled

By Jack

Have you ever been tied and stretched on a medieval torture rack?

It is one of the most painfully intense tortures you can experience.

The further you are stretched, the more painful it becomes. It can also be extremely dangerous, too. Shoulders can be dislocated, lungs can collapse, muscles and tendons can be sprained and snapped. You would definitely want to avoid being stretched out too far.

This type of torture was standard in interrogations. The victim was usually stretched painfully and then asked questions, or made to confess to heinous crimes against the church or state. With every wrong answer or refusal to talk, the cylindrical drum at the top of the rack was turned another notch, and the body was stretched more and more, inch by inch. Even after obtaining a confession, often the stretching continued until the victim passed out. Or worse. The victim usually had no control over how far his body was stretched.

But what if you found yourself tied to such a device?

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Fourth-Quarter Tickle Blitz

By Jack

Yo, Bud –

Got a little challenge here for ya.

Time to see how tough you are, and what yer endurance is like.

You man enough to accept the challenge, or you gonna wimp out right now?

It’s just a little game, dude. You like engaging another jock in a little friendly sport, don’t ya? May the better MAN win.

Here’s the deal:

You are down here on a Friday night. We got tickets for Rangers/Leafs at the Garden on Saturday night. We been drinking beers, horsing around, bullshitting one another, when I toss out this game idea. You lose, you gotta wear… you know which jersey to the game and root for…you know which team (GO, RANGERS! YO!)

Here’s the game plan: You get tied for four quarters, with a break between each quarter. Simple little endurance challenge. Each quarter lasts an hour. No sweat for you, right, tuff guy? You hold out for four hours, you win. You win, and I got to pay a penalty. Any penalty you come up with, no matter what it is. No questions, no backing out.

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