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, bullshitting. 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.
Now, we had never arm wrestled before, but at 6'4" and 200 lbs., I am a lot bigger than him. And being an ex-basketball jock, I am actually a lot stronger than I look. But I laid it on thick, baiting him, and saying that I would probably lose because he was so much stronger than me. Yeah, right. I was secretly pretty confident that I would win.
The match, at the table in the living room, was over in about 30 seconds. I took him down easily, slamming his wrist onto the table with little effort. You should have seen the stunned look on his face! He asked for the best two out of three (why do losers always do that?), but I refused, and grabbed him and marched him into my room for his bondage punishment. He came along reluctantly.
My bondage board, which is 9' long and about 15" wide, was set up like a table, waist-high and horizontal. The board has a series of holes and hooks in it, perfect for tying a guy down in any number of very secure positions. Since we had both been hanging out barefoot and bare-chested, I just muscled him over to the board and pushed him down onto his back. I then spent the next 15 minutes tying him very securely to the board with several coils of thick rope. His wrists were placed over his head, arms bent, biceps flexed, and I tied ropes around his wrists, forearms, above the elbows, and below the shoulders, using the holes in the board to lace him down very tightly. I grabbed his bare feet and pulled them down to the foot of the board. With his feet hanging over the end of the board, I spread his ankles and used more rope and the holes in the board to tie his ankles very tightly. More rope was then wrapped around his body and the board at his chest, waist, crotch, and knees. He was strapped down pretty good, but I wasn't finished yet.
Taking two lengths of strong, thin sash cord, I started to tie up his toes to really immobilize his bare feet. Tying the end of one cord around the base of his big toe, I threaded it back through one of the chains that support the end of the board from the ceiling, and pulled hard. This caused his foot to flex back and his toe to be pulled back at a severe angle. Bringing the cord back to his foot, I looped it around his second toe, and threaded it down through a hole in the board between his legs, again yanking hard. Back up from under the board, the cord wrapped around the outside of his foot and looped around his middle toe, then back through the chain, pulling that toe back in a different direction. Back to his foot, I looped the cord around his fourth and fifth toes together, and yanked it hard out to the side of the board, where it was securely tied off to a hook in the board. Now each toe was bound and pulled in four different directions, making any movement of his foot virtually impossible. Then I did the same to his other foot. Throughout this, he kept bitching and moaning about the ropes being too tight and his toes hurting, but I just smiled and continued my work.
When I was done, I sat back and admired the sight. Man, was this dude tied up and helpless! He didn't realize that his ordeal hadn't even begun yet.
He was still being cocky, and asked for a cigarette. so I lit one and put it into his mouth. But he soon realized, after a couple of drags, that I wasn't going to help him anymore, so he was stuck with a burning cigarette in his mouth, ashes eventually falling on his upper chest and face. That was his last cigarette for nearly two hours.
I next did two things that I am really ashamed about. His hairy armpits were so stretched out and vulnerable that I got the idea to shave them. I thought that would compliment his smooth, muscular chest. I went and got my Panasonic hair trimmer and completely removed the hair from both armpits, while he was struggling and cursing at me. I then attacked them with my fingers, tickling the shit out of the now defenseless pits, making him squirm and yell and laugh uncontrollably. You should have heard the swearing coming out of him, when he could catch his breath long enough to actually form words. What a filthy mouth on this guy!
His cigarette had long since burned right down to the filter. I ignored his sputtering grunts indicating that I should remove it from his lips for him, so he picked his head up off the board as best he could, and spit the cigarette out onto the floor. It quickly went out, and I asked him if he wanted another one. Surprisingly, he said no.
The other thing I deeply regret doing to him was messing around with his crotch. There was this unspoken thing about no sexual contact between us, but he was tied so helplessly and his cock and balls were bulging so nicely through his tight jeans, that I couldn't resist. But I didn't actually touch them. I simply got out my little electric hand-held vibrator, positioned the vibrating pad right on his cock and balls through the jeans, used some gaffers tape to tape the vibrator to his crotch, passing the tape over the vibrator and under and around the board to get some good pressure going, and turned the damn thing on. He jumped and did his best to squirm as the vibrations tickled his trapped genitals. And you know, an electric vibrator never gets tired... The thing hummed along happily for over an hour, while I went down to concentrate on those trapped bare feet.
Pulling up a chair and getting comfortable, with a nice cold Michelob handy, I proceeded to tickle the shit out of his beautifully trapped bare feet. Using my fingers and fingernails, I found that the base of his tied-up toes, between the toes, and especially the helplessly-stretched arches were amazingly ticklish. And I really dug in. I could hear him laughing and cursing and gasping for air, but I just continued on and on. I could see his feet trying to flex and move away from my tickling fingers, but his toes were tied and stretched so tightly, that his feet just tensed up without being able to move. Poor dude, must have felt pretty helpless right about then.
Besides my fingers, I used two old toothbrushes to explore his helpless toes and soles, and they got quite a reaction. So did the two shaving brushes, which worked equally well on his now hairless armpits. And the vibrator hummed along, so he was always being tickled in at least two different places.
One of his fatal mistakes was not to have set a time limit on his bondage ordeal, so I took full advantage. I really get off on tickling a guy's bare feet and I can do it for a long time.
Rick was finally pushed to his breaking point, gasping, begging, and generally showing signs of total fatigue and submission, so after about an hour and a half, I finally took pity on him, removed the vibrator, and untied him. He was exhausted and shaky as I helped him up off the board, he mumbled something about getting back at me, and stumbled down the hall into his room to pass out. While his genitals had been well-stimulated, he claimed he never shot inside his jeans, and I didn't check, so we'll never know.
He never got back at me. A few months later, he moved out of town. We still talk once in a while, but I haven't seen him since.
This is only one of several tickle bets I've made with straight guys. It's a lot of fun, and I'm always looking to make new buddies who might be up for a good challenge.