He squirmed uselessly in the constrictive rubber, letting lose muffled yelps for help into the darkness that surrounded him. A simple gag of Scotch tape was all it took to silence his cries for help, not that the padded walls around him were going to let any sound escape. He was at the mercy of a cruel, vindictive woman, but things hadn't always been that way. As he was squeezed by the warm and constrictive walls around him, he thought back on the series of events that lead to his current imprisonment.

It had begun the previous day as he stood outside a high-end New York hotel in his red bellhop uniform. A line of golden thread spelled out "Dan" across his breast, informing any passersby who this belabored college student was. It was the summer, so Dan was doing his best to earn back all the money he'd spent on college courses. A bellhop job was probably one of the better ways to do that, Dan thought as he made a sideways glance down the street towards a distant 7-11 where a different student was likely working. His thought on his serendipity were quickly interrupted as a sleek black town car pulled up in front of the building. The passenger side door opened and Dan's eyes went wide at the woman climbing out.

He had definitely seen some gorgeous women enter the hotel, running the gamut from high-class prostitutes with clients in tow to spoiled teenage daughters of rich CEOs. And yet none of them were the same as the woman before him. Dan's eyes couldn't help but trace her from the ground up. Her black stiletto heels clicked on the pavement as she extended one out the car. Rising up her smooth legs was a layer of nylon. Beyond that was the skirt of a business suit that began about halfway up her thigh, allowing Dan a quick view at the lacy black panties she wore as she dragged her body out from within the town car. The skirt connected seamlessly into a matching blazer with a white button-down shirt worn beneath it. The shirt was open enough to give Dan a substantial view of the woman's generous bossom. As she stood up to full height, which was only an inch shorter than him, Dan's eyes immediately locked on the woman's face, trying his best to show respect to the likely important client.

Looking at her face-to-face gave Dan a chance to observe the woman's features better. She had light porceline skin and brown eyes that matched the long hair cascading down her back. Her face was without flaw, with the exception of a beauty mark just below her lip. Despite her attire, she didn't seem very old, potentially only 27. Although, between her face and body, Dan was having trouble believing she wasn't a supermodel.

"Valet, fetch my bags," She addressed Dan with a cold, even tone.

"Y-yes ma'am," Dan replied quickly as the woman vanished into the lobby.

Dan went around to the trunk and pulled out the woman's luggage, a rolling suitcase and a weighty computer bag. Judging from the woman's attire and modest packing, she was probably heading out on a flight tomorrow for a business trip. Dan mentally frowned as he realized he wouldn't get much of a chance to enjoy the woman's good looks while she was staying at the hotel. If he had known the predicament he'd been in within the next 12 hours, he'd quickly wish he hadn't thought such a thing.

Inside, he found the business woman waiting beside the open elevator doors, tapping her foot impatiently as she watched Dan approach. The bellhop felt her eyes looking him up and down, sizing him up like a piece of meat in a butcher's shop. Dan did his best not to return a similar look to the buxom business woman, customers tended to tip better when he didn't gawk at them.

The elevator ride up to the 20th floor was one of awkward silence. Dan could feel the woman's eyes on his back, apparently continuing to look him over. However, every time he glanced back a little bit to confirm this feeling, he saw the serious brunette was standing, eyes forward, with her arms folded beneath her impressive bust.

Finally, the elevator echoed with a resounding ding and its doors shuddered open. Dan stepped out first, then waited, allowing the woman to go first and lead on to her room. As Dan followed the woman down the hall, his eyes were drawn downward, towards her shapely ass, barely continued in a tight work skirt. His eyes quickly looked up as he saw the woman begin to turn. His gaze met the woman's and he swore her cold features softened a bit, revealing a subtle smile.

"Right here," the woman said, standing before an open doorway. Her tone suddenly didn't

Producing a folded bill she leaned forward, her breasts mere inches away from Dan's chest and slipped the money into his breast pocket. As she backed away, Dan reached into his pocket to find a twenty dollar bill, alongside a deep blue condom. His eyes went wide and he looked up to see the woman openly smirking as she beckoned him with a single outstretched finger.

"Why don't you come in and help me.....unpack," she whispered

Dan's body went rigid as he broke out into a cold nervous sweat. The woman backed into the open door with a smirk on her face, watching as Dan quickly picked up the bags and followed her in. Dan stepped passed the woman, setting her bags down at the center of the room as a matter of habit. He heard a thump and a click behind him and turned to find the brunette leaning against the door as if splayed out on a bed. She had removed her blazer and allowed a few buttons on her top to loosen, revealing a lacy black bra cupped around her perky breasts.

Dan stood awkwardly at the center of the spacious hotel room, unsure of how to proceed. On one hand she was stunningly gorgeous and undeniably eager, yet on the other hand he could easily lose his job for this. The woman answered for him as she approached, rolling her hips with each step. Dan felt her arms wrap around his body, pulling him in close. He felt her lips on his neck, the warm wetness of a kiss followed soon by a playful bite. As she pulled her mouth away, Dan felt a jab in his neck, unlike that of the woman's bite. It was like.....a needle.... Dan stumbled backwards his vision blurring as he fell towards a sofa standing against the back wall. The last thing he remembered before he passed out was the woman speaking up again, her tone now an even blend of blunt and sensual as if she enjoyed his plight.

"My name's Jessica, little one," she said with a smirk.

Dan came to in an unusual predicament. The room was dim, illuminated only by the rays of dawn filtering through the drawn curtains. He tried to call out, but found that his mouth wouldn't open. It felt like it had been taped shut.

'What kind of kinky woman did I stumble across,' the college student wondered.

As he tried to reach up and remove the tape from his mouth, he found himself unable to move his arms. He squirmed a bit and found that he couldn't move his legs either, it felt like he had been stuffed in a sleeping bag that was several sizes too small. It was at this point that he noticed the feeling of rubber over his bare skin, extending from the neck down. It gleamed in the dim light filtering in, reflecting it back to Dan in a bluish hue.

A heavy wind followed by a loud, somehow feminine, noise caused Dan to jerk his neck to side. His eyes went wide at what he saw. The gigantic face of Jessica, the sultry brunette businesswoman, recoiling from a yawn. Her eyes fluttered open and she greeted Dan with a devious smile. Dan yelled into his gag, jerking his body around as he tried to back away from the now colossal woman as she rose to sit up in bed. Jessica continued to smile as she sat up to full height, rising hundreds of feet above Dan, who lay helplessly on her nightstand.

"Well good morning, little one," Jessica began with a smirk.

Dan yelled and screamed at her, calling the gigantic woman many unpleasant names, none of which made it past his gag.

"Mad, are we?" Jessica asked rhetorically.

Dan's muffled yelps were of the affirmative variety.

"Don't blame me, you should no better than to follow strange woman into hotel rooms. And its not like I told you what the condom was for."

Dan took a break from his screaming, his lungs burning for air which he heartily took in through his nose. He took the moment to take another look at the restrictive "sleeping bag". Sure enough, he was imprisoned in the same rubber that had been slipped into his pocket the previous evening. It was rolled up to his shoulders where a hair tie spiraled around to keep Dan from slipping out.

"You should be thankful, three inches is a lot more than I give most of my toys," Jessica noted as she saw Dan take in his predicament.

Dan gave another muffled cry for help, pointless though it was. Jessica responded as if he had asked a question.

"Yes, I have done this before. Shrunken people are addicting. One of many ways they're like alcohol. Though normally, I'd prefer a tiny that's more like a fine wine, you'll have to do. A quick shot of liquor for my long flight today."

Dan gulped as the woman finished her speech, confirming his fears that she was unlikely to help him in any capacity. She was crueler and colder than she had seemed when she first exited her town car, her softer tone and constant smile at his plight only reinforced that.

"In any case, I don't have time to answer all your questions like 'Why me?' or 'How did you do this?'. I guess the gag makes that a lot easier, wonder why I never tried that before." The woman, now musing aloud, rubbed her long fingers along her chin in a contemplative gesture.

As she was lost in thought, Dan did his best to try and get away, inching across the nightstand like a pathetic worm. Jessica's eyes soon fell back to her fleeing toy. Her hand descended and scooped him up with little effort, bringing him up to the scrutiny of her brown eyes.

"Now then, just one last thing to pack up." Jessica explained, Dan saw her free hand go down to her waist were it began to tug at the lacy black panties she had slept in, "I think it goes without saying, you will be having a rather uncomfortable trip through airport security."

Dan was helpless to watch as the woman slide her panties down her legs, revealing her toned ass and a cleanly saved pussy to him. His body was lowered down towards the former in a slow, torturous motion. Her free hand pried apart the two thick cheeks, revealing her puckered anus between them. Dan immediately began to struggle as the woman began to move him closer to the awaiting rose bud, his feet angled for entry.

Jessica gave a content sigh as she felt her victim's feet make contact, vibrating pleasurably as he tried to kick his way to freedom. This was a much better plan than the last time she'd tried to sneak a tiny through airport security, a rather handsy guard had to pat her down, nearly finding the shrunken man she'd stashed in her bra cup. She let out a soft moan as she pushed Dan deeper.

Dan, on the other hand, was no were near as happy with her predicament. He struggled as hard as he could as he watched his feet and legs disappear into the woman's asshole, sinking him up to his waist. The moaning from the woman above did help him keep his cool as he screamed for help. His screams were pointless though as with another shove, his body vanished up to his chest into Jessica's backside. He felt her thumb press down on his head for the final stretch, pressing him down till only his head was poking out, his neck be constricted and almost choked by the wrinkled ring. Inside Jessica's body an uncomfortable heat and tight walls ensured he would remain uncomfortable for his stay. The continued presence of Jessica's thumb made him worried that she was about to push his entire body inside herself.

The idea did in fact cross Jessica's mind as the stimulating squirms of the poor bellhop started to make her feel moist.  She gritted her teeth though and pulled her hands away, causing her rounded cheeks to snap back into position, immersing her victim in a crushing darkness. She knew that shoving Dan any deeper would mean that she wouldn't be able to pull him out for her time on the flight. In fact, he'd probably have suffocated by the time she was able to force him out the natural way. Without any more thought to her shrunken victim, Jessica dressed herself and called for her town car to bring her to Kennedy International Airport for a non-stop flight all the way to Los Angeles.

Now in the present, his body entombed in a vindictive business woman's ass, wrapped in a condom, and walled off by her tight panties and skirt, Dan had tired himself out struggling. He had no idea how long he'd been stuck hanging out of Jessica's asshole or when, if ever, she intended to take him out. He had just spent an hour long ride in early morning New York traffic with Jessica's mountainous cheeks squeezing his head like a grape as she rode comfortably in her town car. Of course, he had no idea the kind of torment that would await him when he finally was freed from Jessica's backside.