How Ticklish is Tony?

When the author meets a cocky eighteen year old high school wrestler named Tony, he challenges the jock to a male tickling session to prove his manhood and earn $100.
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How Ticklish Is Tony?
by Lyle Blake

ticklish tonyI saw him late one afternoon in my local supermarket. Just a shade over average height and very nicely put together. He was striding cockily down the aisle in front of me, clad in a tightly fitting one-piece wrestling suit that clung to his small ass and accented his long lean legs. He didn’t have a T-shirt on under the suit, so that its narrow straps and scooped-out armholes revealed the broad shoulders and rippling muscles of a truly fit athlete. A cap of jet-black hair covered his well-shaped head. The way he carried himself said arrogance, macho cool and raw sex appeal. I knew that I had to have him.

I turned and hurried back the way I had come, rounding the corner and heading quickly down the next aisle so that I met him coming the other way. He didn’t give me a second look, so I was free to feast my eyes on his exceptionally handsome face. His skin was a perfect alabaster white, and the eyes were deep blue, framed by very long, very dark lashes. I judged him to be about eighteen, maybe a bit older.

I started to follow him through the store. When he got to the dairy section and stopped in front of the display where cartons of eggs were stacked, something funny happened. Another boy, very similar in coloration but with a less mature face and a relatively undeveloped frame, came up behind him, evidently making a deliberate effort to walk softly. This kid, who looked about fourteen, was definitely sneaking up on my muscle boy. The older hunk made his selection and reached up to a high shelf to lift down two cartons of extra-large eggs. For the split-second that he paused in the act of lifting the cartons, both arms were raised high over his head, causing puffs of dark hair to show at his deep armpits while the thin material of the wrestling suit clung to his sides and outlined a prominent ribcage. That’s when the younger kid struck. Pouncing with a little cry of triumph, he ran dancing fingers up and down his victim’s sides and then jabbed two fingers of each hand into those inviting pits. The reaction was extraordinary: The older guy gave a violent jerk that convulsed his entire muscular body, while an explosion of laughter erupted from his lips. His arms came down involuntarily as if pulled by strings, the two egg cartons went flying, and there was a spectacular mess on the floor of the aisle.

The young kid found all this terribly funny’. “Oh God, Tony,” he gasped, “if only you could have heard yourself! And look at the mess you’ve made!”

Tony was flushing beet-red with embarrassment and anger. “What the fuck do you think you’re doing?”

“I’m getting even with you, Tony,” was the youngster’s smug reply. “You think just because you’re my big brother that you can do anything you want to me. I’m sick and tired of you wrestling me down to the ground and tickling me silly every night. Just because you’re bigger and stronger doesn’t give you the right to pick on me!”

At that moment a pleasant-looking woman with the same dark hair as the two boys rounded the corner and exclaimed in dismay. “Mom! Look what Tony did!” the younger one was quick to point out.

Tony, his serious perfectly chiseled face set in an expression of concern, tried to explain. “I couldn’t help it, Mom. He sneaked up behind me and tickled me and made me drop them–”

She wasn’t buying his excuse. “Now, Tony, I’ve told you before that a boy of your age has no business being that sensitive to the touch. There’s no reason why a high school senior should be that ticklish. Why, last week when your cousins held you down and tickled you at the family reunion, I thought you were going to die, you were laughing so hard.”

He looked even more embarrassed, if possible, and shuffled his feet. She went on, “As a partial punishment, young man, you are going to walk home from here. And it will serve you right if it rains on you!” With that, she collected the younger brother and swept away. In the meantime, as Tony ruefully headed for the outside door ‘ my mind was whirling. Surely, Tony would appreciate it if a helpful driver stopped to offer him a ride?

Ten minutes later, having waited in my car to give him a little head start, I spotted him walking along the side of the highway and swerved over. He was full of thanks as he piled into my passenger seat and leaned back, spreading his long legs and stretching his arms out, giving me another peek at his muscular secret pits and the rippling muscles of his tight stomach where the wrestling suit clung to it.

I tried to get the conversation going in the right direction by complimenting him on his body and asking about the wrestling suit.

“Oh, yeah,” he drawled, “we have a really wild time on the wrestling team. It helps keep me in shape, and the guys are a real blast. We just finished having tryouts for this season’s team, and next week we’re gonna have the initiation for the new team members.”

My groin stirred at that word, “initiation,” I started to evolve a perverse scheme. “Initiation, huh? What kind of stuff do you do to each other?”

He laughed. “It’s mostly really stupid stuff, because we’re not allowed to do anything that causes pain or would really hurt you. So we make the new guys do stuff like put ketchup in their hair or run around the block in their underwear. The idea is to test each wrestler to see how cool he is. We try to make him beg, and he tries to tough it out no matter what we do to him.”

I cleared my throat. “I guess you had to go through the same thing when you joined the team, huh?”

He was incredibly casual and relaxed. “Sure. But they didn’t get me to knuckle under. I’m one cool dude, if I do say so myself.”

“Hmmm. I can tell you are. But I bet I could get you to give in, if I had you tied down so you couldn’t move.”

He laughed again. “Oh, sure! You’d threaten to cut my balls off or something! I’m tough, but I’m not stupid!”

“No, no. Even if I had to follow the rules you use in your wrestling initiation, doing nothing that would hurt you or cause you pain, not even anything that would leave any marks, I’m sure I could get you to surrender and ask me for mercy.”

This arrogant kid wasn’t convinced; he curled his upper lip into a sneer, which made my racing blood quicken even more. “I bet.”

“Wanna bet? I tell you what. I’ve got a hundred bucks in my dresser drawer at my place. You come by there with me right now, and if I don’t have you caved in and begging by dinnertime, the hundred bucks are yours.”

He gave me an incredulous look. “Let me get this straight. You tie me up. You don’t hurt me, you don’t do anything that’ll leave a mark on me, all I have to do is keep my cool for an hour, and I get a hundred bucks?”

“That’s right.” I made the turn onto my street.

“But if I lose–I’m not gonna lose, of course–but if I were to lose, I sure don’t have a hundred bucks to pay you.”

“That’s okay. We’ll make this like that game Truth or Consequences. If you lose, I get to pick a consequence and you undergo it.”

He shrugged his broad shoulders. “Sounds good to me. Let’s get down to it.”

Soon we were in my apartment. I led the way into the bedroom and got some very sturdy leather straps I just happened to have in my closet. “What do you have on under the wrestling suit?”

“Just a jock.”

“That’s cool. Strip down out of the suit and lie down on the bed and I’ll get you all set for the test.”

He seemed unalarmed at the order to strip, probably thinking incorrectly that there was nothing sexual going on as long as he got to keep the jock on. I almost held my breath as he grasped the straps and slowly peeled down the top of the suit. Because of his dark coloration, I had feared that he would have a hairy body; to my pleasant surprise, his smooth firm chest was not blemished by even a single hair. The pecs were small but solid, the nipples soft and succulent, the tummy flat and hard. He kicked off his hightops and stepped out of the suit, standing there for a second in the tightly fitting jockstrap. Then he lay down on his back and, without my even having to prompt him, stretched his arms and legs out to the four corners of the bedstead.

I worked fast with the straps and there he was, firmly tied spread-eagled before me, absolutely helpless, his delectable ribs, rippling stomach, and dark hollow armpits mine for the taking. My hands were shaking as I began the test.

“Yep, Tony, you sure do look tough.” And I bet you are.” He smirked up at me confidently. “But I bet I’m right about something else too. I bet you’re pretty ticklish.”

The smirk vanished, and his already pale skin went several shades whiter. His eyes goggled slightly at me, as he made a choking noise in the back of his throat.

“So what do you say, Tony? Are you ticklish?”

He had to clear his throat. “Uh. N-no. No, I’m not.”

I wanted to make him say the word. “You’re not what, Tony?”

“Er, I’m not … ticklish.” He was trying to be ultra cool, but I noticed that he was surreptitiously flexing the muscles of his arms and legs to see how firm his bonds were. I went on.

“Well, it’s a funny thing, Tony. Some young guys are a lot more ticklish than they think they are, even when they’re big tough muscular guys who’ve gotten almost all the way though high school. You might just be more ticklish than you think. I tell you what, Tony. How about if I test you to see how ticklish you are?”

He licked his lips, obviously terrified out of his wits. “No, I don’t think you have to do anything like that. You can take my word for it. I wouldn’t lie to you. I know what I’m talking about.” He was almost babbling.

“No, Tony, I really think if we’re going to be fair about this bet I have to find out everything I can about your body. I guess I’ll start with your sides.” And grinning fiendishly, I reached out for him.

Using one finger of each hand, I slowly started to stroke his lower sides right above where his jockstrap ran over his hipbones. Moving lightly, with a delicate teasing touch, I gradually inched up toward the bottom ribs.

“Yeah, it’s funny how some guys are such pathetic wimps that they can’t stand to have anybody even touch them. I’m glad you’re not like that. Now remember, Tony, if you want that hundred bucks, if you want to prove you’re as tough as you say you are, you have to keep your cool. I don’t want to hear a word of protest, not even a sound.”

I got to the ribs and started to exert a little more pressure. There was no way Tony could stay still while I was doing this to him; he bit his lower lip and squirmed a little bit.

“What’s the matter, Tony? I thought you said you’re not ticklish.” I kept my fingers going.

“I-I’m not.” Now I started using all my fingers and thumbs, caressing each rib as I traveled up his obviously sensitive sides. He was panting in shallow gasps now and really starting to squirm a lot more, but the straps had him helpless.

Tony was fighting desperately not to show me how ticklish he was, but after what I had seen and heard in the supermarket he was doomed. I got to his deep muscular armpits, outlined by his straining tendons as he struggled in his bonds. I started to draw little circles on the smooth patches of skin just under the pits, at the top of the ribcage. Tony couldn’t stand anymore; as much as he tried to stop it, he jerked under my hands and started to giggle.

“Hey, Tony. I thought I just heard you start to laugh. Are you sure you’re not ticklish?”

He was still giggling, because I had not stopped drawing those deadly little circles.

“Because if you really are ticklish, that means you lied to me. And it means you’re not as tough as you thought. Come on. Admit it.”

He had his eyes screwed shut, and his mouth was working helplessly as he clenched and unclenched his fists, where they were bound securely up above his head.

“No, no, I’m–ha–I’m not–ticklish–ah,ha,ha–no–”

My ruthless hands slid into the deep hollows of his pits and started to move back and forth over the damp curls there, and he burst into agonized laughter.

“Okay! Okay!” he gasped between gusts of laughter, as he fought for breath. “I’m ticklish! I admit it!”

“Good,” I said, continuing to probe and stroke his incredibly sensitive armpits, while his muscular, almost nude body writhed and bucked beneath me. “Now all we have to do is find out how ticklish you are.”

He was laughing so hard by this time that he couldn’t talk any more. I stopped the tickling and gave him a chance to catch his breath, while I shifted my position and started a close-up examination of his stomach.

It was gorgeous, hard and well-muscled, and right in the middle of it was his belly button, open and vulnerable to my touch. The belly button was a fairly deep one, with a wrinkled bottom, and when the sheaths of muscle in his gut jumped and flexed as he continued to jerk under me the secret cavity of his navel seemed to be contracting and expanding before my eyes, almost as if asking to be explored. I smiled.

“Hey, Tony, this looks like a really nice belly button. Since you’ve finally admitted that you are ticklish, I guess you won’t mind if I try tickling you down here. What do you say?”

I stiffened the index finger of my right hand and slowly started to lower it toward his belly, and I saw his eyes widen in fear.

“C’mon, man, you don’t need to do that. Let’s move on to some other part of the test.”

“No, Tony, I really am curious to find out exactly how ticklish you are. And since we’ve proved that your word can’t be trusted about your ticklishness, the only way for me to find out is by personal experiment. Here goes.”

With a feathery touch as light as a spider’s footsteps, I started tickling all around the edges of his belly button, and he went berserk. This area must have been even more sensitive than his armpits, because he started to arch his back and twist from side to side in a desperate attempt to escape my relentlessly tickling finger, all the while letting out with these deep hearty gales of laughter that seemed to be erupting up from the very bottom of his stomach.

Finally my index finger went right down into the belly button, scraping and poking and prodding, and that did the trick of pushing him over the edge. His laughter took on a higher pitch, and he started to beg.

“No, don’t, please don’t. Stop. Ha, ha ha, stop. I can’t stand it, hahaha, don’t tickle me anymore. Ah, ha. I can’t stand to be tickled. Please, stop, I’ll do anything you want if you’ll just stop!”

“Well, Tony,” I said cheerfully, finally stopping the torture and removing my finger, “it looks to me like you’re not going to win our bet. But I think, just to be fair, that I ought to give you one more chance to cooperate with me. I have to tell you that I got a big kick out of tickling your armpits. You’ve got such nice muscles, and the tendons there make them look so deep and inviting, especially when you’re working your arms trying to get loose from those straps, that I’m not sure I can control myself, just thinking about tickling those pits again.”

He interrupted me, almost hysterically, with a “No! No!” but I just kept talking.

“As a matter of fact, the only thing I can think of that’s going to stop me from tickling you to death up in these armpits–” and at this point I raised both hands and poised them directly above the vulnerable hollows, “is if you can accurately repeat after me the magic phrase: Please Don’t Tickle My Armpits, Kind Sir.”

I was now wiggling all my fingers in the air, and he was already giggling and jerking and almost out of control, even though I hadn’t touched him yet.

“No, ha, don’t. I couldn’t stand it, you can’t! Don’t!”

“You’re not saying Please don’t.” My fingers got closer to the puffs of dark hair in his deepening pits.

“Okay, please don’t!”

“Please don’t what?”

He was going crazy now, flexing his powerful arms and bunching up his shoulders, but he was very securely bound and absolutely helpless. “Please don’t tickle me!”

I stopped the descent of my hands but kept the fingers wiggling. “I don’t think you were listening to the magic phrase, Tony. Please don’t tickle you where?”

Now he was laughing steadily while he twisted in his bonds, totally psyched out by the deadly wiggling fingers that were within inches of touching his open and sensitive pits. “My armpits!”

“A whole sentence, please.”

“Don’t tickle my armpits, please!”

“Sorry, that’s not it.” My hands moved almost imperceptibly, and he made violent motions as if he would start to climb the walls if he were free.

“No, ah, hahaha, c’mon, don’t, please. Not my armpits, please.”

“I’m sorry, Tony, but you’re not doing too well on this test. I told you there was only one magic phrase that would stop me from tickling you to death here in your pits, and you haven’t said it yet.”

With that I lowered my fingers all the way and started lightly tracing the insides of his armpits, stroking the sweat-dampened curls and running fingertips all along the inside edges, and he started screaming.

This was a fantastic moment, a moment to give a lifetime for, as he bucked and thrashed so violently beneath my ass that I was almost thrown off. I tickled those helpless armpits without mercy for a good ten minutes, while he laughed himself almost unconscious, then I pulled back

His normally pale skin was heavily flushed as he gasped for breath and fought to regain his composure, and he refused to look me in the eye. I laughed myself, although not as heartily or as desperately as he had.

“Okay, Tony. Repeat after me, and I won’t tickle you anymore. I am not a tough guy and I never was.”

At that he did look at me, with a glare that showed just a trace of his old cockiness. “Tony, I don’t think I heard you.” I poised the fingers of one hand right over his belly button, and he caved in.

“Okay, okay. I’ll say it.” He paused slightly and then mumbled, I am not a tough guy and I never was.”

“I didn’t quite hear that, Tony. Could you say it again, a little louder?” I flexed the fingers that were hovering just above his rippling stomach, and he blurted out in a loud voice, “I am not a tough guy and I never was!”

I got off the bed and put a sad look on my face.

“Tony, I do believe you’ve lost the bet.”

“I don’t care about the bet. You can keep your lousy hundred bucks. Just don’t tickle me anymore.”

“Whatever you say, Tony. Only don’t forget our agreement. Now I get to pick a consequence for you to undergo.”

Fear returned to his handsome face. “Don’t tickle me anymore! Please! I can’t stand to be tickled! You know how ticklish I am!”

“Oh, I’m all through tickling you, Tony. I’m not even going to touch you again. You just have to give me your phone number.”

He looked suspicious, but another wiggle of my fingers persuaded him. I walked over to the bedside phone, congratulating myself on coming up with a priceless consequence to cap this afternoon of tickle torture.

“Yes, Tony, this afternoon in the supermarket I saw this young teenage guy who looked like he might have been your brother, and I sort of got the feeling that you’ve been picking on him a lot. Maybe even using the advantage of your stronger body to get him helpless so you could tickle him. I imagine that he would love to get back at you but up to now he hasn’t had the chance. It seems to me that if I leave you tied up like you are now you’ve lost your physical advantage. What do you think would happen if I got him over here right now? I bet he could get in a good hour of tickling you before your mother even missed you!”

Tony was starting to beg again as I picked up the phone.

Lyle Blake

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