You'll need to build a frame to accommodate the guy. It would be easier to draw, but I'll do my best to describe it to ya. So bear with me O.K. pal?
* the frame is in the shape of a "Y", the upper part, the "V" is made out of 2X4's, for the lower part "the tail" use a 2X8
* the tail of the "Y" is long enough to accommodate most guys from their crotch to about a foot beyond the top of their head
* the top of the "Y" is about 2 feet apart and has two more 2X4's going out back of it at 90 degrees, creating an "L" and then somehow braced to the body of the "Y" (I'm not a carpenter so you figure it out). It should be short enough that the guy's feet and ankles extend beyond the end of the "L". Each of these bars has hooks fastened to the sides for tying toes back
* at the top of the "V" at the bend you put another longer 2X4 which extends out across and beyond the two arms of the ever popular "Y"; put good strong hooks into it.
O.K. Here's the deal. Challenge a guy to a little endurance test. If he loses, he's your bondage boy for 48 hours and you get to tickle torture train him to your heart's delight. If you lose . . . well I guess that'd be up to him . . .but he's goin' down, so don't worry Bud!
Get the guy to remove his shirt, shoes and socks. Force him to lie down on his back on the frame (it's on the floor with the arms of the "L" pointing down and resting on blocks). The guy will have to bend his knees to keep from sliding down the frame. Make sure the inside of his knees are snug against the "L" part of the frame and then firmly tie his lower legs to each 2X4. His crotch should be pretty well lined up with the crotch of the "Y". Pull his arms above his head and behind the tail of the "Y" and tie his wrists there, just to keep them out of your way for the time being. Time to attach the ropes to the cross bar and crank the guy up. Just far enough to get the tail of the "Y" off the floor. At this point the guy looks basically like he's hanging by his knees from a trapeze. Let him dangle there for a few minutes to let his body stretch out naturally and acclimatize itself to the position before you continue. Strap his upper legs to the "V" part of the "Y". Then go back and deal with his feet, tying his toes back and out, creating that stretch you like to get on them. Untie his wrists and put a wrist restraint on each, then chain his wrists to hooks in the floor. Raise him till you can begin to see the pull on his arms . . .
The word "sir" is important in this endurance test, so now might be a good time to for the guy to learn to say "SIR" like he really means it. You can put him through a "Racked and Tickled" type of scene or just plain stretch the guy till he's spurtin' out the word "sir" like it's the only word he knows. When you get him to that stage, lower him a bit to reduce the stretch and then finish tying him up. Add a strap around him and the tail of the "Y" just above (or I guess below, since he's upside-down) his hips and make him suck in his gut while you pull it good and tight. Create a rope harness to secure his upper body tightly to the tail of the "Y". One more strap and you've got him just about where you want him - it goes around his forehead, anchoring him to the tail of the "Y", immobilizing him nicely. The guy should be lookin' more expertly trussed up than a Christmas turkey. Unchain his wrists but immediately tie them to the tail of the "Y" behind his head again. Lower him back to the floor and position the top legs of the frame on those blocks again.
Let him rest for whatever time you like and test him occasionally for the word "SIR". Make sure he still LIKES to say it . . . A LOT! It shouldn't be a problem since the guy should be sweatin' pretty good by now. Make sure he knows his "Sir Lesson" was just a prelude and his endurance test is yet to begin.
Go get a barbell and put just ten pounds on it. Attach a couple of sturdy straps with D rings to either end of the bar, but inside the weights. If the guy is stupid enough to want more weight on it, be sure to oblige him. Untie his hands from their position on the "Y" and get the guy to grip the barbell, duct tape his hands to it about 2 feet apart. Go to the winch and crank him up until the barbell is a couple inches off the floor.
The guy has to give you 200 reps, lifting that barbell in a nice, slow, pretty arc. It's gotta start right from the bottom and come up and touch his upper thighs, where he can hold for one second or so, and then slowly back down in the arc to the bottom, where he's in a stretch. He's allowed to hold at the bottom for two seconds . . . one thousand and one, one thousand and two. Make him count them out loud, just for the hell of it! For that matter make him count out his reps too. Might as well keep the guy busy. The fella's allowed to bend his elbows slightly to reduce the stress on them.
Let him pump out twenty or so before you tell him they don't count `cause he just has been saying "one thousand and one, one thousand and two", instead of the required "SIR, one thousand and one SIR --- SIR, one thousand and two SIR". Tell him to start over and YOU start in on his feet. Keep your eye on his form too and let him know there are penalties for being sloppy . . . reps added, weight added, tickle penalties or whatever strikes your fancy, buddy. So it'll go like this: 1st rep - he lifts the barbell to his thighs (SIR, one thousand and one SIR) lowers the weight and counts out the first rep (SIR, one SIR) then still at the bottom he counts the two second hold (SIR, one thousand and one SIR - SIR, one thousand and two SIR) then he lifts for his second rep and on it goes!
If the guy makes a mistake in counting the reps it's back to number one again. If he forgets to say SIR - well now, that's up to you, the penalty depends on how much you like to hear him say it, I suppose!
When the guy starts begging for a break, tell him he can have it if he repeats "SIR I'm a wussy faggot SIR" (or whatever) ten times without a mistake and then "SIR, may I have a Time Out SIR?" Lower him down so that the bottom of his feet are about a foot off the floor. Hook two ropes to the straps on the barbell and winch him up so that his torso is parallel to the floor. "Alright buddy boy you got yerself a ten minute Time Out". You put him through ten minutes of overall torso tickling to find his weak spots . . . then it's back to work with him till the next Time Out or until his muscles give or until he says whatever you want him to say to end the test. If the guy still seems relatively O.K. at this point let him hang there for a while, just to build his character.
As you lower the guy (still tied to the frame) back down to the floor you say:
"So, welcome to New York buddy. Well now, I've got a feeling in the next 48 hours we're gonna be able to make a MUCH better sport outta ya, Pal. What d'ya think BOY?"
"SIR, lookin' forward to it SIR!"
Pick (just a guy who can't say "SIR")