Timid Timmy's Tale of Terrible Sripping

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Status: Finished  |  Genre: General Erotica  |  House: Stripping and Humiliation

timid timmy is lured by his neighbor ana, who, using her looks and the boy's ingenuity, puts him in handcuffs... whatever could happen to a boy who can't fight back against the serial humiliator ana...

Timmy squirmed and struggled against his cuffs sheepishly.

“What are these for, again?” He asked, his voice seemed a pinch of fear from breaking. The seventeen-year-old seemed only now coming to his senses. Had he really not realized his compromising position until then?

Ana couldn’t help but eye her prey up and down. Timmy —no, little Timmy— Milesman was an adorable teen two years her junior. A mane of long, curly, light-brown hair crowned a rather childish, prim looking face; his feature glass-like in their fragility. Big green eyes looked fearfully at the female figure that imposingly stared down at him, a cute, small nose sat between to pinkishly shaded cheeks. A soft jawline was accompanied by a pair of soft, small lips that were all but trembling. Poor Timmy. He did not do well with uncertainty, and the fact that Anna was analyzing his predicament instead of answering his questions seemed to be quite torturous for the teen.

The boy was quite short for his age, not quite looking seventeen. His skinny frame, his somewhat childish sense of style and the fact that he couldn’t even grow a wisp of a beard didn’t help him in looking older than a pale, lanky, twelve year old. A pale, lanky and scared twelve year old, she corrected herself mentally. The little guy lay on her bed, arms over his head, cuffed securely to her bedpost, stretching his short body as far as it could go.

“Oh, silly me, I must’ve forgotten why those were for. What did I tell you those were for?” She played dumb, coiling one of her many blonde locks of hair. She put on a pouty, innocent, I-could-do-no-wrong face just for good measure too. God she loved messing with the boy’s mind: lull him with a sense of security before really crushing the poor fellow.

“Well, uh, you told me you needed help figuring if you’d built your bread correctly and—” He said timidly before he was cut off.

“Ugh, right! I hate putting together stuff from IKEA. Anyways you were saying…” Had she really needed to cut little Timmy off? No, of course not! She simply enjoyed watching the boy cringe as he realized that she had control of the conversation. Well, to be fair, she had control of everything that would be going on soon…

“And you told me you knew this trick called the handcuff trick, to see if a thing was sturdy…” He said hesitantly. He clearly still had hoped she’d teach him some wild trick to see if the bed would break down into pieces or remain the robust wooden structure it was. Adorable.

“Oh, of course, the handcuff trick…” She said, barely able to contain her mean smirk. She didn’t know for how long she’d be able to put up the sweet girl façade. “But I don’t think I remember it now… Silly me. Maybe we should do something to pass the time until I remember it, what do you think, Timmy?”

“I… Yeah, I’d like that.” He said.

“Hmmm...” Ana theatrically stroked her chin, histrionically putting up an ‘I’m thinking’ kind of pose. She tilted her gaze slightly upwards and leftwards as she said: “What to do, what to do…?”

“Ummm, Ana, could you, uh, untie me?” The boy asked, hope in his eyes.

“Oh, don’t be silly, Timmy! It’d just be a waste of time, un-cuffing you now and then re-cuffing you when I remember that darn trick. Plus, I can think of many, many things to do to you while you are still like that…” Her naughty side started to show. She couldn’t cover her grin as anxiety took over the boy.

“Don… don’t you mean with me?” He asked shyly.

“Oh, no, little Timmy, I mean to you. For example, I’m just thinking, I could really take off those pants of yours, and you wouldn’t be able to do anything about it… Would you?”

“Uh… No, I… I wouldn’t…” He said absentmindedly. Clearly, Ana’s victim’s focus was on his squirming and struggling, both of which he now performed —quite delightfully for the nineteen year old girl—, without even an attempt to hide his actions. The chains that bound his cuffs dangled a high-pitched melodious tone as he tried to pry the cold, heartless steel away from his wrists. It was to no avail, however. Not a single boy had ever escaped those cuffs of her.

Ana sat on the bed next to terrified little Timmy and let her hand fly down to his chinos-clad inner thighs. He crossed his legs tightly, more than likely an act of reflect against her intrusion. He blanched as he looked at his captor, now completely still, mouth slightly agape —Ana was sure it was dry with fear too!—, eyes big as platters staring at hers, pleading for mercy.

“I would like to hear you say that sentence. The whole sentence, Timmy.” Ana said as she started to slowly, oh-so-slowly, drag my fingers upwards, toward his waistband. He seemed to take the action as the threat… err… motivator that it was and quickly started blabbering.

“You… You could pull down my… uh, my pants, Ana.” He said, stuttering quite adorably. His cheeks had already taken a deeper rose tone than before. Clearly the mental image of a pantless Timmy had had quite an effect on the little boy. Oh, his fears were a drug more intoxicating than any other for the wicked girl!

“And…” She started. He clearly had tried to get out of admitting the best part of it all. What a naughty, naughty boy. I’ll tame him eventually, she thought.

“And I… I wouldn’t be able to… to do anything about it.” The green-eyed teen said, his voice dry, fearful as he felt my hand grip his mid-thigh suddenly.

“You’re good and obedient, little Timmy. No, go on and say it all together for me.” Ana stared intensely into his eyes. He’d tried to avoid the confrontation of it at first, but the wicked blonde had chased his gaze around, and once she caught it, he dared not break the tense eye contact.

“Ummm, Ana, you could… you pull down my pants and I’d… I wouldn’t be able to do anything, ummm, anything about it…” He said. Poor Tmmy’s voice decreased in volume as he spoke. It probably had something to do with the daunting feeling of his tormentor’s hand slowly but surely running up his inner thigh once again.

Ana grinned and mischievously let her fingers dig between the fabric of Timmy’s underwear and the tight waistband of his olive-colored pair of pants. She sat there, gripping his garments, but not moving as she commented. “Oh really? You wouldn’t be able to do anything about it?” My voice took in a lustful tone.

The red-faced teen did nothing save for squirm and shake his head no. He couldn’t do anything but that, being all too conscious of the soft yet commanding grip Ana had on his attire. It seemed to Ana the poor boy had come to his apogee of embarrassment and anxiety. Naturally, she decided to go past that.

“It’s okay that you don’t want to answer me, Timmy, we’ll find out just now…” She teased him. Her cat-like grin made her face beam as, after having announced it to her victim, started to slowly —even slower than she’d moved her fingers before— started to pull down the boy’s pants down.

Timmy cringed, fear and shame taking ahold of him, yet his only reaction was to mumble “No, no, no!” over and over as he felt his pants slide down his legs. Suddenly, before even his full pair of underwear was showing, Ana stopped.

“Should I continue, Timmy? You are looking quite embarrassed.” She asked teasingly, both her hands still grabbing his trousers. The boy seemed too shocked to respond, so she tried again. “Do you want me to stop, little Timmy? Do you want me to leave your little pants covering your undies?”

The boy, finally coming to his senses after having been overwhelmed by shame, nodded wildly as he said “Yes, yes please! Ana, thank you!”

She smiled meanly and tugged. Just a bit. The pants didn’t move noticeably, but the boy yelped a high-pitched sound and frantically moved his arms, producing a satisfying ding from his bounds clinking together. “Do you really, really want me to let you keep your little boy pants on, Timmy?” Ana asked, her tone was mocking, babytalk-like. “Say it for me, my plaything.”

“I…” His voice was but a mere whisper, and quite a high-pitched, desperate one at it. Music to Ana’s ears. “I really, really want to keep my li… my little boy pants on, Ana… please?” The teen noted, quite delightfully, how the cuffed boy had maintained her degrading tone.

“Well…” She said as she let go of his pants with one hand, which she used to lay with her hair in a silly, unoccupied manner. “When you put it like that…” She relaxed the grip on her other hand, all her fingers save her index clasping nothing but air now. She noted how Timmy looked at that last finger pleadingly. Teasingly, she moved it towards the front of the teen’s pants, and then back. She went on for a few seconds, giggling at her victim’s expense. “It’s really a shame you can’t do anything about me taking them off then, is it not?”

With her sole clothe-grasping finger used as a hook, Ana kept on pulling down. Timmy’s eyes looked glossy with tears, and he said nothing but a high-pitched, aghast “Nooooo!” as she stripped his pants. His voice, so near breaking, was like a delicious treat to cruel Ana. He wanted oh-so-badly to stop her, Ana was sure. The boy squirmed about, desperately trying to get her hands off of him, but it was to no avail. The chains and cuffs restrained his arms firmly over his head and she easily overpowered the weakling’s attempts at crossing his legs to halt her progress.

Soon, the olive-green pair of chinos rested bunched up at a very embarrassed boy’s ankles, as the girl who had slid them down inspected her newly-revealed entertainment. With the sweet sounds of Timmy begging her to un-cuff him as a pleasing background noise, Ana inspected the boy’s legs. They were smooth, hairless and milk-white. She helped herself to more than a couple strokes of the inner thigh, each and every time getting closer and closer to the loser’s underwear.

Finally, Ana let her eyes wander and inspect said underwear more closely. Little Timmy wore —much to his haunting, she was sure— a pair of tight, childish briefs. In his struggles, she’d realized, his shit had ridden up, offering a lovely, unobstructed view at the boy’s undergarment. The soft, pale-red fabric clung to his body tightly, and covered little to nothing save for the essential. As if that wasn’t enough to embarrass her victim, the pair had a silly-looking little stickman stitched in a maroon thread, right over where his privates were. Playfully, Ana focused her attention on it, her slender index finger tracing it softly, over and over again.

“Wow, Timmy, I guess you really couldn’t do anything about me pulling down your pants, huh.” Ana teased. “Quite a nice view, you know. Your face is almost as red as that little guy’s one!”

The boy closed shut his eyelids, fighting the tears of shame. His face was burning a bright, bright red, his normally pale complexion acting as a canvas for the humiliating color. He still tried reaching downwards, but no luck there, his hands still held tightly by the cold, steel manacles.

“I can see your undies, you know, Timmy.” Ana mocked the slightly-younger teen. “And your pretty little legs. They are so smooth. Do you shave them, Timmy?”

“N… No…” he mumbled.

“Oh, what a lucky little girl you’d be then. So smooth, to kill for…” Ana kept on, relentlessly teasing, yet pausing dramatically every once in a while, taking in again and again the sight of the almost-botomless tied up boy. “Come to think of it, your undies do look like a pair of little panties, you know, Timmy?”

Little Timmy offered no reply, seemingly too embarrassed to properly address Ana.

“Tell me, Timmy, do you think you look like an embarrassed little girl?” She said as she slowly slid his shirt upwards. She stopped when the white garment covered nothing save for his pectorals. Unsurprisingly, the boy was not muscled at the abdomen, but rather flat and skinny.

“I… I don’t know…” He managed to get out between sniffs.

“I really think you do. Look, you are wearing red panties and… yes, your shirt now looks like a white bra.” Ana smirked.

Once again, the little guy was silent, overwhelmed by the shame of having had his underwear uncovered and stared at.

“Say it for me, Timmy.” Ana commanded authoritatively, deciding once again, to take his humiliation up a notch. “Tell me how you are a little girl and how you are being seen in your undies by a big girl like me” Oh she was devious!

“I’m… I’m a little girl and you are a… a big girl, Ana.” He said as quickly as he could. His tears slid coldly, contrasting against the heat of his face.

“Oh, c’mon, my little Timmy, you can do so much better than that. Use your words, be descriptive…” Ana demanded, her lustful, playful tone came back to her.

“I… I, uh, am a little girl and… and I’m wearing my tight, red p- p- panties and my little white bra… and nothing more, and Ana… who… uh… who is a big girl, is seeing me in just my undies.” Oh how he struggled with words, it was marvelous. Ana had him completely debased. And she loved every second.

“A little girl indeed.” She affirmed, pleased with herself. “But don’t you think a little girl like you, with no boobies, shouldn’t wear a bra?”

“I… I don’t know.”

“Little girls agree with big girls, right?”

“Right…” Timmy said hesitantly.

“So you agree that a little girl like you shouldn’t wear a bra?” Ana pressed on.

“Y- yes.”

“Well then…?” The devious girl asked, as though her request was obvious. The boy, having obviously not caught up to what she’d meant —and deliciously terrified at the prospect of the consequences of that—, remained silent. “Ask me to remove your bra, silly little Timmy.” The boy sighed, defeated.

“Ummm, Ana, would you remove my… my l… little girl… bra?” The boy paused, though Ana, unsatisfied with the level of shame, simply stared at him coldly. “… Please?” he whimpered finally, on a pitch higher than the rest of the sentence, and a tone quite softer. It was, to put it lightly, charming. How could Ana not help out such a damsel in distress?

The older teen worked slowly, making sure to steal many a glance at her near-naked plaything as she worked. She was careful as she worked. She had to uncuff each of Timmy’s wrists to fully remove his shirt and, she wanted not a spec of unwarranted freedom in her preys mind. She made sure to tightly pin the wrist she unlocked while she removed the white, Pikachu-stamped t-shirt.

After a few moments, Ana had Timmy fully topless, his t-shirt lay casually on the ground next to her ruffled bed. Cruel, cruel Ana even locked the cuffs even tighter than before, really making sure the frigid steel dug mercilessly onto Timmy’s skin. Did she need to? Of course no. But his flinching and yelps made it worth her while.

“I really like taking off your clothes, Timmy.” Ana said casually. “I’ll take your pants off now too, while I’m at it, no need for them to be at your ankles any longer.”

Ana knew the psychological impact of having the boy’s clothing actually removed from him. Before, he was uncovered, sure, but he knew that with a few swift motions of my hands, I could cover him again —not that I would have!—, but If his clothes came all the way off? The he was really vulnerable, she thought, satisfied at her expertise in the area. Her extensive practice was showing, too. Timmy practically shone a deep red, almost competing with the lamp for brightness

She did quick work of the boy’s shoes and socks. His last garment was one quick tug away from abandoning, yet Ana wouldn’t let him out of his predicament so easily. No sir.. Ana let her fingers dangle and play with his clothing for a while. She would tug at it, and then pull it slightly upwards to correct the movement. She would pull the waistband away and let it snap back into place —the first time she did this, surprised little Timmy let out a moan of pain that was simply precious to hear— yet eventually, she reached the peak of her mental torturing of the boy, and finally slid his olive-green pants fully off of him.

“Look at you, Timmy!” Ana said, triumphantly waving the boy’s pants as she spoke, teasing him, reminding him of his state of near-nakedness. “Almost naked, all tied up for me. Such a treat seeing you like this, tight, red undies clinging to your skin, a face equally as red...” She focused her eyes on the specific parts of the body she was describing. Timmy had resorted to a soft, shameful but oddly quiet sobbing. Good, Ana thought, elated. “Tell me, Timmy, do you want to be let out?”

“YES!” He sounded hopeful, renewed. “Yes! Oh, yes, please, please, Ana, please, let me go!” The male teen seemed to snap out of his shame-induced trance. He squirmed relentlessly, chains clinking and clanking once again as he moved frantically.

The girl smirked, and seductively reached between her ample breasts —God bless low-cut shirts, right?—  and, with a theatrical flourish, dug out a necklace, the jewel of which was the key to poor Timmy’s handcuffs. She took off the necklace, much like she had done a few moments ago when she’d removed his T-shirt. Only this time, she started to play with the necklace, balancing it, looking at it, as she spoke.

“You certainly deserve to be let go… I’ve stripped you, teased you and humiliated you all day long, isn’t that right, Timmy?” She went on as the boy nodded wildly, his mouth practically salivating his escape. “You really want me to put this key on the lock of those manacles and let you go, huh. You really, really do.”

“Yes, please, please, please Ana!” He kept on begging, his face still pink, but not the bright red from before. “I’ll do anything, Ana, please, just uncuff me!”

Ana shifted her position in a few dexterous moves. She went from sitting next to her victim to straddling him. She sat atop his hips, her tempting, booty-short-clad behind barely a few centimeters away from the embarrassed boy’s crotch. Yet, her demeanor wasn’t seductive or sexy. No. Timmy realized quite quickly her demeanor was cruel and imposing. He gulped, as the teen was closer than she’d ever been, wild, cat-like grin plastered on her face. She was up to no good.

Ana was all but giggling at the boy’s expression of pure disappointment. Oh, Silly Timmy. Had he really believed she’d take pity on him? Poor innocent boy. She’d teach him how boys are supposed to be: at her mercy, burning with shame.

“Well, Timmy, I guess I’ll just have to give you the key then.” She spoke as she guided the chain of the necklace around Timmy’s neck. With a quick snap, the accessory was on him, the cold metal of the key resting against a hairless, uncovered chest that bobbed up and down due to heavy-breathing.

She got off of him and stood up, proudly looking at her handiwork. Oh she was terrible! The seventeen year-old’s face had regained whatever red it’d lost, and the boy himself was squirming and twisting himself in every way he could think of, just to try and get a grip on the key. However, the oh-so-short chain that bound his cuffs together would allow him no such thing. It was tantalizing, watching his hopeful eyes look at the key like a man lost in a dessert might look at a glass of water, yet unable to reach it. Ana was beaming.

“You’re so, so close to your freedom, Timmy, and yet, you can’t do anything about it, can you?” She mocked the little boy, who looked ready to break down crying again. When she finally managed to peel her eyes off of her own torturous game, she continued. “I’ll be back in a second, Timmy, don’t go anywhere!” She couldn’t help but giggle at her own comment.

Before leaving her room, Ana picked up all of Timmy’s fallen clothes. One by one she stashed them in a bag. And she giggled all the while, simply to mess with her red-clad victim —or… well, maybe because the struggling pathetic little boy was a sight so humorous she couldn’t hold her in-control persona and simply had to mock him by giggling—. Once no clothing remained on the floor, she made her way out, closing her door behind her.

Timmy was left to his own devices and, though the door between them was closed, Ana could still hear the satisfying, desperate sounds of a metallic chain colliding with, scraping against and bouncing off a wooden bedpost. Oh it was the perfect torture for hapless little Timmy. So close and yet so far… She enjoyed the sound for a few minutes after having hidden the boy’s clothes and fetching the provisions she’d previously prepared. She just loved the idea of the wild, wild thoughts running through restrained Timmy’s mind. In a way, giving him hope that he could get out while he still had a secret —hopefully a little secret!—, albeit, a false hope, was even a more perfect way to further torment the boy than simply stripping him.

But, eventually, Ana grew bored.

“Hi Timmy, I’m back!” Ana said in a high-pitched sing-song voice as she entered her room, closing her door behind her. The boy, his eyes wide as they’d ever been, glassy with unshed tears, froze and stopped moving about with his chained hands. “I missed looking at that tiny bulge of yours, barely covered!”

Ana took her customary spot once again, sitting on her bed next to her bare-chested little victim. As she looked deep into his eyes, she let her hand rest atop his inner thigh. Soon, she lifted all but her index finger and, barely making any pressure, began running it up and down Timmy’s moonlight-pale legs. The squirms and uncomfortable moans and “Mmmm!’s” that resulted of this made her grin madly.

“So, Timmy…” She said, her voice histrionically uncertain, as she ran her finger past the side of the boys underwear —purposefully avoiding his crotch… for now— and tracing patterns on the boy’s flat tummy and hairless chest. “… You’re only wearing your undies now…” She held his gaze for a few moments, letting her words sink in. “… Do you know what that means, my little toy?”

The boy gave no answer save for near-quiet yelps and cries.

“C’mon, Timmy, be a good little toy for me and tell me, what do you think will happen now that you are only wearing your tighties?”

“I…” The boy was still dazed with humiliation. Ana’s touching driving his face a more tantalizing, redder shade than before. “… You’ll… you’ll take them off?”

“Are you asking me?”

“Er… no…” He said nervously.

“The say it, don’t pose a question!” Ana demanded, mischievous lust on her eyes. Stripping was important, but verbally teasing the boy was key to shaming him as much as possible.

“You’ll take my underwear… my underwear off.”

“Maybe I will…” Ana teased, her hand still running wildly through Timmy’s bare flesh. “Maybe I won’t… But first, there’s a little something I will do to you.”

Ana stopped teasingly touching the boy and bent over herself, reaching for something in her pale-yellow bag-of-fun. She could hear the boy’s ragged, heavy breathing. Oh, what could he be thinking? What could she do to him before finally stripping? It was a delicious moment, which she savored for longer than she’d needed to, her fingers not rummaging through the contents of her bag as quickly as they could have.

Yet eventually, enticing though it was, she stopped letting the boy’s mind run wild and finally pulled out a little ice-cube mold, which, shielding it with her back from the eyes of Timmy, shook until she pulled out a single cube.

“My, my, little Timmy, you are so red in the face I supposed you were feeling quite hot.” Ana said impishly as she turned around to reveal her hands. “This should cool you down a bit.”

She lowered her hand towards Timmy’s torso to the melodious sounds of a pleading “No, no, no, please, no!”

Playfully, she let the ice cube atop Timmy’s hyperventilating torso and watched it dance around, the movement of the boy’s shivers and wiggles provoked the frigid thing to move about wildly. It was an enthralling show, watching the little cube melt to water atop her victim’s chest, helping it get back up when it slid off. Timmy’s nipples got hard and erect from the cold, his skin getting frosty to the touch.

“Is it too cold, Timmy?” Ana asked mockingly.

“Y… Yes!” The boy said between shivers.

“Well, this next one you are allowed to take off your chest, okay? Just reach for it and take it off!” Ana was all but laughing out loud as she said that.

The next ice cube, Ana traced patterns with. She was deliberate in her teasing, getting the freezing block as close as she could to the tormented boy’s reach and then quickly pulling away. Timmy’s struggles and imminent face of disappointment as he realized he hadn’t managed to slap it off made Ana giggle uncontrollably every time it happened.

She repeated the process for a few more ice cubes, though she focused her attention lower and lower each time. At first, she mocked the boy’s reach, letting the freezing water melt over his arms and wrists. The, she focused on the boy’s pale neck and pink, puffy nipples, tracing cool circles around them. Finally, she let herself wander off to his lower tummy, daring to reach all the way down to his waistband a couple of times.

She wasn’t exactly embarrassing the boy just then, but the sense of complete and utter control she felt were reason enough to keep her entertained. Little Timmy thrashed as she cooled off every bit of his exposed upper body, and yet he could do nothing about save for moan, cry and yelp; maybe beg for mercy as he had deliciously done for the last few moments, but the key was he simply could not stop her. She was in the throes of passion, torturing the silly, tied up boy; the power she exerted over him coursing through her veins like ecstasy.

And yet, her hunger called for more humiliation.

She began teasing the boy with her last ice cube normally, tracing chaotic, geometric patterns over his exposed skin, giggling all the while and enjoying his red, wincing face. Eventually, she started to really focus on the boy’s lower tummy, the ice cube barely leaving the areas adjacent to his waistband. Ana took in the sight of a worrisome face, as the boy realized she was purposefully getting closer and closer to his last secret.

With great enthusiasm, Ana hooked Timmy’s burgundy waistband with her left index finger, which was not leading the small block of ice. And then, she pulled. Slowly, and only a bit; not even enough to sneak a peek —though she kept her eyes affixed on the boy’s—. She held the position for a few moments, enjoying how Timmy’s already red face grew a shade darker and he started to breathe even more heavily.

“Now, little Timmy, are you ready to really shiver for me?” She asked cocking an eyebrow, her right hand provocatively moving the frigid cube back and forward mere centimeters.

The boy seemed terrified, having understood the threat, but he managed to obediently nod, though Ana new it as the last thing he wanted to do.

“Say it for me, Timmy. Say you are ready to really shiver for me.” Ana ordered, her voice commanding. She wanted the anticipation to be just as bad as the forceful cooling itself.

At first, the boy did not answer. Ana hoped it was because he was simply too mortified. Yet, she could not have him disobeying her like that.

“Timmy. Do as you are told. Or else…” She bit her lip. That ‘Or else…’ had such an effect on her prey. It was a testament of how wrapped around her finger she had him.

“I’m… I’m ready to… uh… to really shiver, Ana…” He said timidly.

“You are forgetting a bit, Timmy. Say you will really shiver for me.” She pressed on. “And add that you are an obedient little boy.”

“I… I am ready to-“

“Actually, add that you are an obedient little almost naked boy.” She cut him off, beaming as she devoured the boy’s shame.

“I’m… I’m ready to… to really shiver for you, Ana… Like… Like the little nea- near naked boy that I am…” Oh he was in tears. Silent, cold tears that slid off his red, shameful face. Ana almost had to stifle a moan of pleasure as she took in the sight of Timmy in the most embarrassing moment of his life.

Ana slid the ice cube in and let the waistband’s elastic slap back to its place.

The shivering started almost immediately, much to Ana’s delight. She got up, getting an eagle’s view of her victim. Timmy was a sight for sore eyes. The little boy thrashed about, desperately trying to get the ice cube to slide off his tight underpants, naked save for those, red-faced and eyes closed shut. He let out yelps and cries as the cold took over. Ana could not help but smile broadly at her handiwork.

“Ah! Ah! So… So cold!” Timmy shouted. “Please, Ana! Oh! Please let me go! Ah!” It was to no avail. Ana could do nothing but giggle and laugh at her desperate victim.

The freezing lasted minutes. To Ana, it felt like it was over in the blink of an eye. To Timmy, it felt like an eternity had passed, his privates feeling gelid and over-sensitive.

Ana grinned as she sat again. The icing had had a secondary effect, much like she’d hoped. Timmy’s underwear now stuck to his body, revealing every single little curve. Timmy’s penis was quite nicely outlined for her, the red material clinging to it. Ana didn’t look in detail. Why spoil the big reveal? She thought to herself.

As Ana drifted her attention away from the scantily-clad boy’s crotch, it seemed to her the boy hadn’t noticed the effect the water had had on his clothing, for if he had, he was taking the revelation of his privates far too well. Naturally, Ana had to maximize the humiliation.

“Ooooh, Timmy, look at your undies, I can see your little friend, I think…” She said giggling, her voice mimicking that of an annoying schoolgirl on purpose.

“Aaaah!” The boy gasped wildly and once again attempted to reach toward his crotch before realizing in desperation, that he had both his hands tightly cuffed over his head. “Ohmygod, ohmygod, ohmygod! Ana, please, please, don’t look, please, I beg you, please, don’t look at it.” The way he was panicking? Adorable.

“I barely caught a glimpse, my little plaything, but why shouldn’t I look?”

“It’d…. well, It’d be very embarrassing!” He said, hopeful that he might convince her.

“Would it now? I guess I have embarrassed you quite a bit. Why would it be embarrassing, my toy?”

“Well… It’s private, Ana!” Timmy said, finding courage in keeping his last bit of covered skin clothed.

“Oh, silly, I know that.” Ana said, her voice slowly grading back to her teasing tone. “I just want you to tell me why it’d be embarrassing. Is it because it’s little? What I managed to see wasn’t very big…”

“No!” He said as an act of reflex. “Or… well… maybe… I don’t know…” He was panicking again. Oh, Ana was beyond adoring his demise.

“Timmy, is it little?” Ana demanded.

The boy remained silent for a few seconds.

“Yes…” he said and nodded softly.

“Awww” Ana said triumphant. “Go ahead, say it for me. Say ‘Hi, I’m Timmy and I have a little penis.”

“Ana... please…” He pleaded.

This time, she didn’t even have to verbally threaten the boy. She simply placed her hands at her hips and threw him a glare. Timmy swallowed and gave in. He opened his mouth a few times, but he found himself out of breath. Each and every time he was about to start, his cheeks flustered just a tad more.

“I’m… I’m Timmy and I… I have a little… a little penis…” He finally said, eyes closed, fists clenched. Once again, Camilla couldn’t help but giggle at the teenager. Oh, how would she ever top this with another boy? This one was just the perfect victim!

“Very good, Timmy.” Ana said, letting her hand rest dangerously closely to Timmy’s spoken-about privates, which caused him to let out a surprised, acute ‘Ah!’ “But if you have a little boy’s penis, you shouldn’t use big boys’ words, should you?”

Timmy didn’t answer, but Ana let it slide.

“No, no you shouldn’t!” She affirmed. “Wittle boys like you should say ‘I’m Timmy and I have a silly little itty bitty willy.’ C’mon, pet, say that for me. Tell your owner and about your wee-wee.” She demanded, her hand cupping Timmy’s privates and delivering a gentle squeeze —painless though it was, the boy flinched quite delectably—.

The boy was once again sobbing quietly —it was clear to Ana now how her relentless teasing made all the difference in tormenting the boy—. He struggled to speak once again, teasing her by opening his mouth and quickly shutting it close again and again much like the last time she’d ordered him to speak.

“Hi… I’m… I’m Timmy, and I… I have a little… No, I have a silly… little… little itty bitty… a silly little itty bitty willy.” The last few words were more a sequence of characters slammed together and whispered, for the boy did not found it in him to put the correct pacing to the words. Ana would have objected, had she not been grabbing at her tummy as she roared in laughter. Oh, it was simply too precious.

It took her a few moments to calm herself down, and when she did, she took to inspecting the furiously —almost crimson-looking— blush on little Timmy’s face. Oh, the boy was beyond mortified! To have made him admit his lack of virility like that? Oh it was just marvelous, Ana was more and more convinced she was a humiliation mastermind.

And, of course, no humiliation would be complete if the victim was still wearing any clothing…

“So… Timmy…” Ana said as she tentatively let her hand rest on the boy’s flat, cold tummy. “I think I’m going to take off your undies.”

“No!” The boy spoke up —He all but shouted that first word— for the first time in a long while. “No, please, Ana, you can’t, please!”

“Oh, but I can, Timmy. I can just hook my finger here…” She said as she curled her index finger into a hook-like shape and dug between the moist fabric of Timmy’s waistband and his skin. “And very, very slowly pull down.”

“Noooo!” The boy cried as Ana started the long, tortuous process of fully stripping him. She took her time, eyes fixed on her victim’s not wanting to catch the slightest glimpse yet. Timmy thrashed and wiggled, struggling against the hard, unforgiving metal of his bounds. He tried crossing his legs, but the water of the melted ice cubes acted as a lubricant, allowing Ana to slide his underwear right off.

Of course, even though she could slide them right off, she wouldn’t. She teased the boy, slightly lowering his garment and then pulling it back up, or lowering just one side and playing with her fingers there before continuing and lowering the other side. She’d yank them down a surprising amount only to do the opposite a mere moment later. The boy squirmed and yelped deliciously as she did so.

And yet, after a few minutes of risqué play, the underpants were dangling from the hands of a very mean humiliator.

“Lookie lookie, Timmy!” Ana mocked him, holding his underwear in front of him and waving them like a flag. “You’re naked! If I were to just look a bit downwards, I’d see your little pecker, wouldn’t I?”

“No, Ana, please! Please, give me back my undies!” The boy pleaded, tears streaming from his furiously blushing face. Ana couldn’t help but giggle at the word ‘undies’ used not a teasing way, but an honest one.

“Nuh-uh my little pet, I’m not giving these back. What I am going to do, however, is take a loooooong look at your silly little penis.”

“No!”

“Yes… Say it for me, Timmy. Say ‘Big girl Ana is going to look at my little boy penis’”

“Ana… please…” He begged, his voice back to the near-silent tone she’d grown accustomed to.

“Say it, Timmy. Or else…”

“Big… big girl Ana is going to… going to… she’s going to look at my little boy’s p…. penis…” Oh it was marvelous.

And yet, delicious though it was to listen to the boy admit his pittances of manhood, Ana decided it was time to finally see Timmy’s last secret.

Making sure her victim followed her gaze —his panicky eyes trailing her lustful ones— Ana started to lower her head, and with it, her sight. She saw Timmy’s penis to the accompanying melody of high-pitched “No!” and “Please Ana!”. Could she have asked for a better ambiance?

Timmy’s penis… No, Ana decided it didn’t deserve that word. Timmy’s willy was a sight to behold. Barely visible, the small thing dangled cutely atop a hairless crotch as its owner thrashed about trying to hide it from her sight. She enjoyed the sight of the squirming boy, catching glimpses of his bobbing privates. It was humorous to a degree she had not expected, and she could not hold back her giggles.

When Ana grew curious, however, she decided to get a closer look. She threw him a dangerously frigid gaze —a threat worse than any she could verbally produce— and set to inspect the boy’s willy in detail. Prying his legs apart, she inspected it closely. She had been right, the little thing looked adorably small on the boy. It seemed to her puberty had barely knocked on Timmy’s door. Pinching it with her forefinger and thumb and looking at the underside of it. It was just so small!

“Awww, Timmy!” She said, mockingly “You didn’t tell me it’d be so cute and small! Look at it, it’s tiny.”

Ana carefully caressed Timmy’s ballsack, which was pressed tightly against his skin. She ran her palm slowly against it, feeling how smooth it was, as there was not a hair to be found. She let her middle finger continue the upwards motion, tracing the outline of his silly little thing as well, and tracing circles atop its head.

“And you are so smooth, Timmy, do you shave down there?” She giggled. In all of her stripping escapades Ana had never seen a boy to underdeveloped —and, of course, so embarrassed!—.

The boy remained silent as Ana stood up, clutching the red pair of underwear. She took a good, long look at Timmy. Tied and exposed, red faced and naked, it was a perfect sight. The little boy was thoroughly embarrassed, she could simply do no more to put him in despair. She blew him a kiss, sarcastically before making her way out of the room and hiding his underwear.

***

Ana watched from her window how a very pale and very naked boy made his way to his home. Just because Timmy had been her neighbor it didn’t mean she’d break her tradition and give the boy his clothes back. Though, she pitied missing the opportunity to stalk a naked teen as he made his way through a couple of streets, naked and exposed for all to see.

 

Authors note: Hello everyone! Timid Timmy’ Tale of Terrible sTripping (Alliteration is hard to do well, ok?) ended up being… mediocre, for which I’m sorry. I simply had to finish this, if anything to get past a persistent writers block.  I decided to publish it even though it is not up to my usual standard —or at least it doesn’t feel up to my standard— simply because the world always need more silly boys stripped, right? Anyways, expect some better stripping of boys soon!


Submitted: July 25, 2020

© Copyright 2021 SwimKid. All rights reserved.

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Comments

qwertpoint

it was good, but switching between 3th person and 1th person view was confusing.

Sun, July 26th, 2020 11:11am

Callum white

Loved this, another great story to add to your collection collection

Sun, July 26th, 2020 11:12pm

Blondie2

As I've said before, SwimKid, I love your style, and this was no exception to your entertaining humiliation storytelling. Your depiction of the victim's humiliation is excellent, and is matched by the depiction of his captor's enjoyment..

Thanks for posting, and as always I look forward to your next submission.

Mon, July 27th, 2020 12:36am

massageguy

Loved the slow buildup, and the way Ana made him say things correctly for her. There are some jarring typos, though. Build her bed, not bread. And I'm pretty sure she lifted his...shirt.

Mon, July 27th, 2020 4:53pm

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