Roommate Tickle Wager:
Craps-You Lose



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.

Zack also had a passing interest in bondage, but only with women. He let me tie him up a few times, very briefly, for educational purposes only. He even tied me up once, but of course, nothing sexual ever happened. We were (and are) very good buds.

Anyway, one night, during a very heated game of craps, I thought it would be interesting if we upped the stakes a little. I went to my room and grabbed a few lengths of rope, brought them into the living room, and threw them down into the pot.

When he asked what they were for, I told him, "First guy to lose all his nickels gets tied up."

He really thought about it for a minute and hesitated. I was sure he was gonna refuse, but then he said, "Sure. You're on. Just no funny stuff, O.K.?"

He had no idea of just how funny the evening was going to get.

I rolled those dice like I had never rolled before. I wanted to win so badly, I could taste it. The dice were smoking in my hands. The game went back and forth for a long time, first he was up, then I was up. But luck was on my side. Finally, after several hours (and several bottles of cheap sherry) I won his last nickel. With a whoop of victory, I grabbed a length of rope...

Zack just thought he'd have to endure a few minutes of being tied up for losing at craps. To pay his debt, he stood up and crossed his wrists behind his back. I took the rope and was going to tie his wrists together behind his back, but then I changed my mind. I spun him around, grabbed his arms, put his wrists together in front of him, and proceeded to tie up his wrists. The rope was this thick, cotton and nylon boating rope which is my favorite to use for bondage. I looped it several times around both wrists, then began to cinch it tightly between the wrists. This has the effect of making the coils of rope like two handcuffs, snugly encircling the wrists, with very little space in between.

I marched Zack into my room and positioned him under one of the strong metal hooks which are attached to my ceiling. My room is well-equipped for restraint, with all sorts of structures, pulleys, and hooks in the ceiling and floor. Taking a long length of rope which was threaded through a pulley right above him, I tied one end through the coils of rope around his wrists. I went to the other end and started pulling. Up went Zack's wrists into the air, and I pulled hard until his wrists were way up over his head, his body stretched tightly. As usual on a hot New York summer night, we had been hanging out barefoot and bare-chested, so I enjoyed watching his chest and arms as they strained against the bondage. And of course his armpits were stretched and very vulnerable. I had some idea of what I was going to do to him, so I had to secure him even more tightly.

Grabbing two more lengths of rope, I quickly tied one around each of his ankles, lifting up the legs of his jeans to expose his bare ankles. I kicked his feet apart until they met these two eye bolts which are screwed into my floor, about five feet apart. This made him have to really stretch to keep his balance, and he yelped as most of his weight was suspended from his bound wrists. As I tied each ankle rope off to the hooks, he realized that if he went up onto his toes, he could relieve some of the painful pressure on his wrists. He did, and I stepped back to take in the sight.

Here was my buddy, my roommate, who had been giving me such grief, barefoot and bare-chested, standing in the middle of my room, all strung up and straining at the ropes. That's when all of his former taunting and name-calling came back to me. He had really hurt my feelings several times by calling me a wuss (we have to take enough abuse from other sources; we shouldn't have to tolerate it from friends) and I decided to get back at him.

And what better way than attacking those vulnerable, ticklish armpits of his?

I approached him and, standing right in front of him, I brought my hands up to his face, and started wiggling my fingers in the air. Looking him right in the eye, I asked,

"Now Zack, which one of us is the wuss?"

He replied with a very smart-assed, "You are, you asshole. Now let me down out of here."

Still wiggling my fingers in the air, I slowly began to move my hands down toward his defenseless armpits. His eyes followed my hands, and as soon as he realized what was about to happen, he jerked his body and yelled, "Don't even think about it, dude. Get out of there, or I'm gonna have to kill you."

Nice talk from a guy who is helplessly strung up and who happens to be extremely ticklish. Well, he brought it on himself. Now he pays.

The second my wiggling fingertips made contact with Zack's armpits, he yelled and tried to jerk away, but the ropes had him stretched so tight that he only managed to pull back a few inches. Then the ropes swung him right back and into contact with my tickling fingers. This sorta determined the game for the next 10 minutes or so. By just keeping my tickling fingers at a spot where he couldn't help but make his armpits come in contact with them, I had a great time just wiggling them and watching his squirm and try to pull away. Every time he stretched against the ropes and pulled back for a second, his body was immediately thrust forward again, and my fingers found their mark again. He was yelling and cursing, but soon he also started laughing, a deep, masculine rumble, amidst the yells.

In short order, Zack was panting and drops of sweat started to form on his brow and in his armpits. I knew that the sweat would make my fingers glide through his pits even easier, making him that much more ticklish, and sure enough, it did. You should have seen him bucking and yelling and cursing at me. I was having a blast.

This was turning into the most intense armpit tickling session I ever experienced. And it has never been topped. Yet.

I gave Zack a short break to try to regain his breath, then I approached with another challenge for him. I again started wiggling my fingers in the air near his armpits, and he looked down at them with dread. He started squirming again, and I wasn't even touching him! I brought my fingers to within an inch of each pit, and kept them there for a minute. The sweat was really starting to pour off of him now. Must be awful to be tied up so tightly and tickle tortured on such a hot summer night.

Suddenly, I moved my right hand, fingers wiggling, in toward his left pit, finally making contact. He yelped, and jerked to his right, where my other hand made contact with his right pit. He got a break on the tickling of his left pit, but now his right one was getting it. After a few seconds, he jerked over to his left again, to escape the tickling in his right pit, and his left pit found my wiggling fingers, just waiting there for him. He did this several times, left, right, left, right, until he finally got it. He more or less had to choose which armpit was going to get tickled by which way he moved. And with those ropes so tight, his options were very limited. Back and forth it went, him moving his upper body an inch or so to the right, coming in contact with the tickling fingers, and then swaying over to the other side, where the other pit got tortured. A few times, he actually stayed for a few seconds and suffered the non-stop tickling of one pit, but he couldn't stand it for very long, and he would always move away, just to get the opposite pit tickled. He was basically in Hell, and it was starting to dawn on him how fucked he was.

Between gasping for breath, he was calling me every name in the book, and a lot were very demeaning. I vowed to keep up his tickle torture until I had achieved an attitude adjustment on his part.

I asked him again, "Zack, which one of us is the wuss?"

I think he said, "You are, motherfucker. Now get me down from here.", but it was hard to understand him through his laughing and yelling. His deep, masculine voice and laughter was starting to take on a different pitch. As he lost more and more control of himself, his voice got higher pitched, and he actually started giggling. What a macho stud. I was on my way to breaking him down completely. I was enjoying this immensely.

It was then that I got the idea of how he would be able to end this torture by himself.

Keeping up the alternating armpit tickling, I said to him, "Zack, if you want this to stop, all you have to do is tell me that you are a wuss, and apologize for calling me one.

Zack tried to take this in, all the while squirming to try to avoid my fingers. He finally made his decision, and yelled, "Fuck you, man."

Big mistake.

My work was now cut out for me.

I was surprised at Zack's determination not to give in to the armpit tickle torture. After being strung up and tickled so fiercely, he still had the guts to say, "Fuck you, man" when I asked him to apologize and say that he was a wuss. I renewed my determination to get him to surrender.

Having played sports in high school and college, I knew what pride and endurance were all about. Zack had been a wrestler in high school, and he was calling on all of his stamina to hold out against the relentless torture. I decided to try to psyche him out and wear him down.

The way I had him strung up was definitely tough on him, and it was getting to him. Being stretched so tightly like that, I could see from his squirming and flexing that his muscles had to be getting tired and sore. I had an idea to further fuck with his head.

I suddenly stopped tickling his armpits, and walked around behind him. He couldn't see the ace bandage that I had grabbed, and was now bringing toward him. I quickly brought the bandage in front of his face, placed it over his eyes, and started to wrap up his head and his arms, all in one nice tight package. With his wrists tied together and stretched straight up to the ceiling, his head had been nestled between his biceps already, so I just tightened up the package. Wrapping the bandage several times around his head and arms, I tied the ends in a knot behind his head. Now he was blindfolded, and his biceps were pressed tightly to the sides of his head. The additional bondage stretched his armpits even tighter, further restricting his mobility, and adding to his sense of helplessness. Now, I thought, something frustratingly light and ticklish, to contrast the intense bondage. Drive him nuts.

I waited a few moments, so he could get used to not being able to see what was gonna happen to him, and so that his anticipation would build. His body was tense, his breathing still came hard from his last round of tickling, and the sweat was still dripping from his armpits.

After another few moments, I very slowly brought my fingers up to his armpits again. This time, I just barely grazed the hairs in his pits, wiggling my fingers slightly. He suddenly felt the very light tickling sensation, and he gasped and jerked. After just a moment of this, I stopped and walked away. I went into the kitchen to get a cold beer, and left Zack to wonder and worry when the next attack on his defenseless armpits would occur.

I came back into the room, sat down, and started enjoying my beer, looking at Zack all strung up in front of me. He was squirming and straining against the ropes, now in some definite agony. He was still trying to stay up on the balls of his feet to keep some pressure off his tied-up wrists, but he was shifting around on those bare feet, and flexing and pulling against the rope that hung him from the ceiling. The silence and waiting for the next attack finally got to him, and he said, "What the fuck are you doing, man?"

I didn't answer him, just kept sipping my beer and waiting.

After several long minutes, I finally put down my beer and approached him. He sensed that I was close, and tensed up. I had decided that the best way to wear him down was to do some frustratingly light tickling of his pits. That, coupled with the strain he was undergoing from the intense bondage, might be just unbearable enough to break him down.

Taking both my index fingers, I placed them lightly on Zack's upper arms, just below where the ace bandage was wrapped, on the sides of his straining biceps. He flinched at the touch, not being able to see, and not knowing what was coming. I was counting on his temporary loss of sight to heighten his ticklishness even more. I touched his skin lightly, and then slowly started dragging my fingertips down, closer and closer to his exposed armpits. As I finally reached his pits and lightly dragged my fingertips through them, he yelled and laughed and tried to pull away. But with his upper arms now firmly wrapped to his head, he literally had nowhere to go. He began to giggle again, in a higher-pitched voice than I had ever heard out of him, alternating with some yelling and gasping for breath. Yup, this was gonna work just fine.

When my fingertips reached his sides, I removed them, brought them up to his biceps again, touched down, and repeated the slow and torturous drag through his pits. This slow, very light tickling was having just as good an effect on him as the more intense tickling had a few minutes ago. Zack was giggling and laughing and yelling, and his whole body was incredibly tense. Each pass took a about twenty seconds, and I repeated it over and over, with no break in between.

The sensation of being strung up so severely and being tickled so lightly finally took it's toll on my tough buddy. Between gasps and laughs, he finally said, "Please stop it, man. I can't take it."

With a big smile on my face, I said, "Sorry, Zack, I didn't hear you. What did you say?"

He eventually caught his breath long enough to say, "Stop it! I can't take it!"

I felt that victory was within reach. I thought I had him. I demanded that he say what I wanted him to say.

"Zack," I said, as my fingers kept lightly tormenting his armpits, "Say you're sorry for calling me a wuss."

With a big groan, he took a deep breath and mumbled, through his giggles, "Sorry I called you a wuss."

Keeping my fingers brushing through his armpits, I demanded, "Now, tell me who IS a wuss?"

I knew I had him. I knew I was finally gonna win this endurance test that I had started. He waited several seconds, still laughing and trying to suck some air, even shaking now from the strain he was under, and he finally yelled out, "Fuck you, you wuss. Let me down from here!"

I couldn't believe what I had heard.

This was gonna be tougher than I thought.

But I was now determined to get it out of him, even if it took all night.

Zack had now been strung up by his wrists for well over a half an hour. The ace bandage I used to bind his arms to his head was acting like a blindfold, so he couldn't anticipate my next tickle attack. His position left his armpits, the most ticklish part of his body, totally stretched and exposed.

I couldn't believe that I hadn't been able to "break" him yet. When he said, "Fuck You" and called me a wuss again, I really started getting pissed off. But I also had some doubts that I was going to be able to win this endurance challenge that I had started. It would mean I would go down in defeat, if I couldn't get him to say that HE was a wuss. But being a former jock myself, I know how to push a guy and keep pushing. I hate to lose. And Zack, a former high school wrestler, was proving just how tough and stubborn he could be. I sensed that, even though he was going through hell, that he sorta enjoyed the chance to show me how tough he was and how much he could take. He was in excellent shape, muscular and defined, and we both knew he could take a lot. And damn, he was one of the most ticklish straight guys I had ever met. Too bad for him.

But now, his strength was starting to fail him from the extreme bondage and the nearly non-stop tickle torture to his defenseless armpits. I was definitely wearing down his willpower to resist. He began to slump in his bonds, as I kept up the dreadfully slow, light tickling to his stretched-out armpits. Having his biceps tied so tightly to the sides of his head made those armpits excellent targets. But looking up at his hands and wrists, they were turning white, and feeling them, they were beginning to get cold, so I knew I had better get him down.

But, damn it, he hadn't broken yet. I wasn't gonna give up, no way in hell. I thought quickly about changing his position, trying to figure out how to do it so he couldn't escape.

I went and got two thick, padded leather wrist restraints and a couple of padlocks. I reached up and tightly fastened the restraints to Zack's wrists, just below where they were so securely tied with the thick rope. I padlocked the restraints together. I grabbed three more screw hooks and screwed them into the floor a few feet behind him. I placed the other padlock by one of the hooks. And then, to keep him off balance, I made a full tickle assault on his armpits, digging in with my fingers and wiggling them like crazy. Caught off guard, Zack yelped and tried to buck out of the way, only to be swung sharply back again to my wiggling fingers. He never learns, I smiled to myself. He can't get away from these devious fingers. I kept up the tickling for a full minute, and once again Zack was laughing and yelling and gasping for breath. Time to go into action.

With my buddy off his guard, I quickly untied the rope that was stretching his wrists up to the ceiling. He was still laughing and disoriented from not being able to see, and I grabbed his arms and began to force him down to the floor. With his feet still tied to those wide-spread hooks in the floor, he had no choice but to keep his knees straight and I had no trouble muscling him down. Soon his butt hit the floor and I was on top of him, forcing him down onto his back and pulling his wrists back up over his head. With that ace bandage still tied in place, he could neither see nor move his arms down to protect himself. In an instant, I had forced the restraints down to the hook that was about a foot beyond the top of Zack's head, and padlocked the restraints to the hook. My plan had worked, and he was secured once again, flat on his back, legs still spread and tied.

Trying to catch his breath, Zack yelled out, "Hey, man, what the fuck are you doing? C'mon, man, let me out of this. Hey, I gotta take a leak."

And at that moment, a calm smile spread across my face. I remembered what he had said about his baby-sitter experiences.

As I proceeded to remove the ropes from his wrists and untie the ace bandage from around his arms and head, I asked him again: "Zack, I already got you to apologize once for calling me a wuss. But I really need to hear you say that YOU are one. Say it, buddy, and I'll let you go."

He refused, muttering some curse words under his breath, short as it was.

My conscience was clear. He had sealed his own fate.

I reached down to his hands and roughly massaged them for a minute, making sure his circulation was returning. He was tugging on the restraints and trying to bust free. Since the hook where his wrists were locked was only about a foot beyond his head, he had a lot of movement in his upper arms and elbows. But not for long.

Grabbing two lengths of rope, I tied the end of one tightly around his slightly bent elbow, and fed the other end through one of the hooks off to the side. Pulling hard, it flattened Zack's arm, in a slightly bent position, right against the floor and forced him to stretch his arm as far as it would go, stopping when the wrist restraints would not let it go any further. I tied off the rope, and he yelped at the uncomfortable strain on his arm muscles. I did the same to the other elbow, and now his arms were very securely tied and stretched, wrists together, elbows splayed out, arms tight against the floor. This had the delightful effect of making his armpits slightly deeper than they were when he had his arms stretched straight up over him to the ceiling, when they were more flattened out. I was hoping that those deep, lightly hairy pits, now virtually immobile and stretched taut, would make even better tickle targets. And having him tied down on the floor like this, with me looming over him, would give me a distinct psychological advantage, maybe even make him feel even more helpless and...ticklish.

I stood up and looked down at my helpless straight roommate. Tied to those five hooks in the floor and stretched out so tightly, his muscles were flexed and tense. He looked up at me with a mixture of defiance and trepidation on his face. But he wasn't giving in.

I asked quietly, "Who's a wuss, Zack?"

If he could have spit at me, he probably would have. But he pressed his lips together, in a signal that he wasn't talking. O.K.

It was time to play hard ball. I had just about had enough of his cocky, tough guy attitude, and decided to go for the kill.

I suddenly dropped down and sat down hard on his lower abdomen, facing his head. He winced and tried to suck in a breath, with difficulty. I picked up one, then the other of my legs, folded them in, and proceeded to sit, Indian-style, on my helpless buddy's chest and abdomen. Yup, all 200 pounds of me. I could feel him gasping for short breaths under me. Also, the additional pressure on his lower abs would, I hope, have the desired effect.

I leaned forward and went for his helpless armpits. With all of my fingers, I began a final all-out tickle assault on his defenseless pits. He yelled, and immediately started laughing, the pitch of his laughter getting higher and higher. He tried to suck up a good breath, but my full weight on his stomach and chest made a good, full breath an impossibility. His face immediately started turning a bright red, as he laughed and gasped and laughed some more. My fingers were now really digging into those pits and wiggling like crazy. My strong thumbs pressed hard into the muscles between his pecs and his shoulders, found a soft spot, and they dug in and started wiggling, too. Zack was caught between trying to yell, laughing uncontrollably, and gasping for breath, but with my full weight pressing down on his chest and abs, he could only manage quick, short ones between the hysterical laughter and the yells. He would occasionally cough and sputter, but the laughter was virtually non-stop now. He knew he was in trouble.

I tickled his armpits without stopping. My fingers were getting wet from his sweat. They were wiggling and gliding all around his deep armpits, not missing a spot. Several long minutes of constant tickle torture went by. The time for light, teasing tickling had passed. This was war.

Just to make it a little worse for him, I bounced up and down on his tender lower abs a few times.

That did it.

With an ear-piercing yell, and a grunt that must have started deep in his guts, Zack sucked in the biggest breath he could and managed to yell out, "ALRIGHT! I GIVE! I AM A WUSS! I AM A WUUUUSSSS!"

Without missing a beat, I craned my head around to see if what I thought would happen, had actually happened. It had. A dark spot appeared on the crotch of Zack's jeans, and slowly began to spread.

He was shaking and gasping and yelling now, and practically whimpering like a baby. I stopped the tickling and jumped up, to avoid getting myself wet. As soon as the pressure was lifted from Zack's chest and belly, he started gulping down some deep breaths of fresh air. His body slowly stopped trembling, and as he realized what had happened, he started cursing and swearing softly. I had totally broken him, and he knew it. The added humiliation was a sweet bonus for me.

I looked down at him and said, "Who is the wuss, Zack?"

He looked up at me briefly, then looked away quickly, not wanting to look me in the face. Catching his breath, he said, quietly, "I am." Then he started swearing again and said, "Now let me up outta here."

I quickly untied him and he stood up, shakily. The whole front of his jeans were wet. I said, "Great self-control, tough guy... I mean, WUSS." He glared at me as he headed out of my room and down the hall. In a moment, I heard the shower water running. He must have gone straight to his room after that and just passed out, because I didn't see him again until the next day.

Man, victory is sweet. Luckily, this incident did not adversely affect our friendship. Zack transferred to a different college and had to move out of New York a few months later, but we are still in pretty close touch. He is a good buddy.

He never tried getting back at me.

And he never called me a wuss again.


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