Jenni The Clown: Nate's Mistake F/M

“Tight enough for ya?” Jenni asked Nate sweetly. The more he pulled on his bonds, the more they appeared to constrict him. In all fairness, he had asked for it. Literally.

Growing up, Nate had looked forward to Jenni’s visits. Every kid needed a babysitter from time to time and Jenni never minded making extra money. Jenni had a way with kids, even before becoming a clown for parties. She was always up for a good time or a good game. The two of them had hit it off right away.

Over the next couple of years, her visits had become an almost weekly occurrence. One night, and for the first time ever, Nate got upset at her demand for him to do his math homework. She had offered him a challenge: Prove that he was too grown up to have to do children’s work, and she would let him off the hook. She tackled him, pinned him to the ground, and tickled him by grabbing his hips. When he broke into laughter, she told him that she had proved he was still a child because he laughed at being tickled. Something that she claimed only little boys and girls do.

The whole ordeal had humbled him, to be sure. But he had also had an even more interesting revelation than that: He had enjoyed it. He liked being held down and manipulated. At first he thought it was just that he had a crush on her. As he got older, he realized that while he did like her, he liked being restrained in general. He confided in her, telling her how he felt about it. And eventually it became a normal thing for her to tie him up during her visits. Sometimes she would tickle him. Sometimes she would simply watch in amusement as he tried to escape, often commenting on how helpless he looked.

That was years ago. But not much had changed. Nate was now 18. Jenni was 23. They had gone a few years without speaking, having drifted apart as friends sometimes do. But they had recently run back into each other and Jenni had invited him over for old time’s sake. It hadn’t taken long for him to ask her to restrain him once again. She was all too happy to oblige him, hogtying him in the middle of her living room floor. She had made him strip down to his tighty whities first, just to humiliate him further.

“Is it?” She asked again.

“You must be getting soft.” He shot back. “I’ll be out of this in a jiffy.”

“It’s giving you a stiffy in a jiffy.” She laughed, knowing how aroused he was by the situation. It was another reason why she had wanted him to be nearly naked before she tied him. She wanted to track and gauge his libido. “I see something has grown since you were little. Remember our deal. If you can’t get undone in the next two minutes, you owe me kisses.” She had removed her shoes and socks a little while ago. It was one of the games they used to play. He would literally have to kiss her feet if he was unable to get free from her ties. He struggled as she sipped her Jameson. More than once did he catch her rubbing herself as if she was getting off to watching him struggle.

Time was ticking away. And he had no chance of escaping. As before, Jenni had taken to using bungee cords to tie him. They held better and were too rough to just slip out of them. He had never been able to shuffle free of them in the past. And it looked like he wouldn’t be able to now.

“30 seconds left.” She told him. He tried to pull and wrestle one wrist free. Just one wrist would give him enough to finish the job. To reach the hooks and unclasp them. But alas, it took him too long. “Time!” She called out, raising her feet. “Alright, piggy. Better wiggle your butt over here.”

“Okay…” He conceded, worming his way over to her and laying on his side. Her bare feet dangled millimeters from his face.

“You know what to do.” She nodded. He raised his head up and to the left, planting a kiss on her left heel. He heard a pleasured sigh from up on the couch and was encouraged to do it again. Jenni loved having her feet adored. Something that many people did not know about her. He moved upward, kissing just above the heel of the same foot. “Maybe some day you will learn not to challenge me, Nate.” She sounded more than a little condescending. He remembered what she had said to him all those years ago when she first pinned and tickled him. He got a wicked idea, kissing the center of her instep. She responded with a girlish giggle. “Hehehe hey now.”

“What’s the matter?” He asked. “Still a little girl?” He kissed her again just under her toes. She pulled her foot away, knowing exactly what he was referring to. “What’s wrong? Cat got your tongue?” He taunted her.

“Oh… so you think you’re a wise guy now, eh?” She raised an eyebrow. “Let’s not forget just how ticklish YOU are, little Nate?”

“No idea what you’re talking about.” He lied. “I haven’t been ticklish since middle school.”

“Oh no?”

“Well, you know, some people outgrow it. Some don’t.” He used a bit of strength and raised his head as if he was going to kiss her toes. She pulled back reflexively and he started to laugh at her. “I guess you’re one of the unlucky ones.”

Jenni could barely hide her fuming.

“Okay, tough guy. So you’re trying to tell me that if I tried to tickle you, nothing would happen?”

“Absolutely nothing.” He vowed.

“Mhmm.” She reached out and pulled the hooks apart, effectively letting him free. “Come with me.”




Jenni led Nate down the stairs into her basement, opening the door to her playroom. The walls were colored pink and blue. On one side of the room was a counter with several drawer like on might find in a science classroom. On the other wall were a number of anatomy charts depicting sensitivity levels of various subjects, complete with notes on each one and images of tickling implements. There was a drain in the floor right at the foot of what looked like a dentist’s chair. The chair was unique. Nate could see a handful of assorted levers built into the chair. Did it come apart in sections?

“Take a seat, Mister I’m Not Ticklish.” She gestured to the chair. He was nervous, but if he backed out now, he would only prove her point. He did as he was told. The chair was more comfortable than it looked. She raised his arms and strapped his wrists to a pole that emerged from the headrest of the chair. She then used a crank to raise the footrest so that he would be in something of a reclining position, and then strapped his ankles in. “Give me a minute or two. I’ll be back.” She walked out of the room, letting the door shut behind her, and leaving him in the room by himself.

The minutes passed like hours. What was she up to? Was she even still in the house? Was she playing some kind of elaborate practical joke on him? He watched the minutes pass on a clock by the counter. She had been gone nearly twenty minutes. He thought that he was going to fall asleep when the door opened back up. She was wearing a satin jumpsuit that was colored bright blue and her face was covered in greasepaint. There was a white face with little pink hearts over her eyes and a little feather on each cheek. Her lips were bright red and there was a little red dot in the tip of her nose.

“Jenni?”

“In my final form.” She joked with a Dragonball reference. “It’s almost a split personality at this point in my life.” He did notice that she was strutting a little more than usual and her voice was a bit higher… more playful. Almost as if she was partially imitating Betty Boop. She moved over to him, standing at his side, leaning over slightly, and dragging a satin gloved finger along his chest.

“Now since we go back, you and I… I will give you one more chance to admit that you are still ticklish. Do so and I might even let you go free.”

“I meant what I said.” He claimed. In his own mind, he was cussing himself out. Jenni was no fool. He knew that. He also knew that she was one Hell of a tickler. What was he doing???

“Okay dokey, tickly wickly.” She moved to the counter and opened a drawer, pulling out a strange looking contraption. It was made of metal and reminded him of a costume gauntlet that he once saw at Hot Topic. It fit on her right hand like a glove, even over the glove that she already wore. The steel points extended an inch and a half past her fingertips. It looked like Freddy Krueger’s glove, except the points weren’t sharp enough to cut. “Don’t worry.” She said. The only thing my toys will hurt… is your pride.” Her index finger point touched down on his belly. He took in a sharp breath as the metal fingertip dragged along his lower tummy. He was already starting to lose the battle. The damn thing tickled more than he could even imagine. If he listened, he could even hear the slight sound of the metal moving along his skin. It sounded like a fingertip on loose paper.

“It’s not… so bad…” He tried to convince himself out loud.

“Well, I’m going pretty easy on you.” She told him. “We both know where your worst spots are. I’m just messing with you so far.” The tool scratched lightly on either side of his bellybutton, causing him to wince with each swipe. “Tell me which is worse.” She requested, using a satin fingertip on one side of his belly and the talon on the other. The combination was getting to him. He started to wiggle around a little bit from left to right.

Jenni knew a ticklish reaction when she saw one. Over the years, she had developed a keen instinct for sensing such things. He could have been perfectly still and she would still have known. But she wasn’t trying to break him yet. This was more about establishing dominance. Putting him in his place.

“You’ll have to… try… better than-” He was cut off by the metal talon entering his bellybutton and gently scratching the knot inside. His expression instantly changed as he pursed his lips and his cheeks blew up.

“Trying out for Olympic swimming?” Jenni asked, noting how he looked as though he were trying to hold his breath. “Oh, that’s a sweet spot isn’t it?” She asked with a tone that sounded almost endearing. “I know how ticklish that special knot can be. It’s an erogenous zone, after all. Full of nerves. And I don’t believe for a second that you can last too long if I just… stroke… over… and over… and over…”

“Hehehehehe okay stohohohopp.” He cracked like an egg after so many soft scratches against the wrinkled bump.

Oh, so you ARE still ticklish after all.” Jenni loved rubbing sensitivity in her victims’ faces. That wonderful moment where she has proven them wrong and gained control over them. The gauntlet worked magic. Soon, Jenni tired of it though, and substituted a gloved finger once again, which she used to ever so lightly wiggle against the soft, purple flesh inside. This sent shock waves flowing violently through the bound teen. The tickles were electric.

The worst was, after a few seconds of fingering, when Jenni bent her head down, pursed her lips around the birth spot… and blew.

PRBRBRBRBRBRBRBRRRRRTT! The sound of imitated flatulence was loud, but merely a whisper compared to the volume of Nate’s screams of laughter. PRRRRBRBRBRBRBRBRRRRRTTT! Jenni punctuated each raspberry with an exaggerated inhalation of air right beforehand. She had no doubt that if she blew into Nate’s belly for thirty straight minutes, the poor boy would probably wet himself. His reactions were that extreme.

Jenni had no intention of leaving such a mess, though. She blew four more times and decided to give Nate a few minutes to collect himself.

“Oh my. I see old tricks still work. Remember when I used to give you belly blasters back in the day. These widdle lips can still make you holler. Hahaha.” Jenni took a moment to observe her prey. “This underwear isn’t too expensive, I imagine.” Jenni went back over to her counter, returning with a pair of shears that she used to snip his tighty whities off. She was now looking at a semi hard penis and everything that came with it. “You used to have a thing for me back in the day, didn’t you?”

“What boy didn’t?” He replied, making her smile.

“Flattery will get you nowhere.” She told him. “But you can keep trying if you want. I won’t complain.” She brought a sharp metal fingertip to his testicles, slowly drifting it around the scrotum.

Nate twisted and writhed, groaning uncomfortably. It didn’t hurt, but it was a strange kind of tickle. One he hadn’t felt before. The point of the gauntlet sent all kinds of tingles through his body. When she traced the seam, he snorted awkwardly.

“I think that’s enough of that. We don’t want you having too much fun.” She guided his glance so that he could see how much his manhood had stiffened. “What can I say? I know my way around.” She gave him a suggestive, playful wink. “And you can’t blame me for wanting to explore you. When we played last, you were still a kid. But now… oh, how you’ve grown. Now, you’re just fresh meat.”

Nate wasn’t sure what to say. But Jenni ended the intimate moment, surprising him with a tickle attack on his lower belly, scratching with splaying fingers.

“HAHAHAHAHAHA COME ON HAHAHAHAHA!”

“Come now. Let’s not forget why we’re here.” Jenni reminded. “Ticky ticky tickle…”

As Nate thrashed about (to the best of his abilities in his straps), Jenni chose to entertain him with her recollections, reminding him of different ticklish torments she had treated him to in his youth. She recalled times when she tied his toes together and played tic tac toe with him, using a sharpie on his feet. Another time when she had made him hold his arms up and feather the wells of his pits. She had always liked to make a game out of it back in those days. Seeing how long he could hold in his laughter… seeing which touches tickled him more or less… sitting on him and seeing if she could tickle him to the point where sheer panic would allow him to get out from under her… she told him about the time that he actually cried one time because the tickling had gotten so intense and he couldn’t escape. And about how she had taken pity on him and let him go. Something that she wouldn’t have done for just anybody.

“But don’t think for a second that I’ve forgotten about the spot.” She told him, getting his attention as she gave his belly and sides a rest. “You know the spot I mean.”

“Yes…” He acknowledged. It was the same spot that had driven him to tears back in the day. The dreadfully ticklish spot that she rarely revisited after that. Thankfully, in the position he was seated in, he knew she’d have a bit of trouble getting to the spot from where she was. His relief was short lived when she grabbed his hips, just as she had all those years ago, the first time she tickled him.

“GA-hahahahahahahahaha…”

“There’s an old standby.” Jenni remarked. “I just press my thumbs in and watch you go to Happy Land. Hahaha. Coochie coo.” She goosed him rapidly as he bucked in the chair. She laughed at him, not mockingly, but out of sheer amusement. He was even more ticklish now than he used to be. She wondered if that meant… “Is the spot more ticklish than when you were little?” She asked out loud. He tensed as she let go of his waist and heard the inquiry.

“Well, you’re not going to find out tonight.” Nate assured her.

“Oh no?” She shot back. “You sound pretty sure of yourself. Care to make a wager?”

“What are you thinking?”

“If I can get to the spot within 10 seconds, I will tickle you for the rest of the night. And with every tool that I have. Fingers, feathers and bears, oh my.” She paraphrased The Wizard of Oz. “But, if I can’t, I will untie you and you can do whatever you want to me for the rest of the night.”

“Anything I want?” He asked her to clarify. She had piqued his curiosity.

“Absolutely anything.” She promised. “The only limit is your imagination.”

“Deal.” He grinned confidently.

“Okay. 10 seconds. Starting… now!” She reached out to grab a small lever on the side of the chair. As she pulled it down, she released the seat of the chair, pulling it away.

“Hold on! I didn’t know you could do that!” He protested in terror.

“Tough cookies, little boy.” She reached out with the metal talons and began to softly tickle the spot, otherwise known as his bottom.

“HAHAHAHAHAHAHAHAHAHAHAHAHAHA HEHEHEHEHEHEHEHEHE HAHAHAHAHAHAHAHAHAHAHAHAHAHA!” He lost all control, bouncing up and down in the chair as if it were on fire. She had discovered the spot by accident many years before. She had meant to mockingly pat him on the seat of his pants, imitating a football player. But he had pulled away and therefore, the hand that was meant to pat merely grazed his cargo short-covered bottom. The sound he had made was one to remember, and she knew at once what it could do to him.

The worst part was that now, she had all night to play with him. And she had no intention of letting him go this time...

Great story! This is a fine series.

Love it