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Cheryl's Big Day (m/f)

T

Tidas

Guest
She finished putting on her mascara, and batted her eyelashes at herself in the mirror. It was the little things, the daily routine, which kept her smiling. That, and her job.
Cheryl was an administrative secretary for a local law office: Siltain, Fergusson, and Hill. Mostly small cases, family law and such, but Cheryl loved her job. She started out as a girl on a phone, skinny as a bean pole and in a dress that hung off of her like a drape. As the years passed, Cheryl developed confidence, capability, and impeccable fashion sense. She worked hard, and now she ran the roost, although that never stopped her from working hard.
She finished putting on her lipstick, and looked herself over in the mirror. At 42, she wasn’t a kid anymore, but she was still lovely. Her umber hair curled right over her bare shoulders, her deep blue eyes showed kindness and sensitivity, and her polite nose was dappled with tiny freckles. She adjusted the strap of her grey sheathe dress, making sure it covered her bra straps, and ran her hand down the front, smoothing out the wrinkles. She no longer had a teenager’s body, and her dress fit very nicely, accentuating her curves.
She tucked her feet into a pair of open-toed, black, kitten heels, and the laugh-lines at the corners of her eyes bunched as she smiled. She loved these shoes, and they did a great job of showing off her new pedicure. “Tickle Me Pink” the glittery polish was called, and she loved it. Cheryl liked getting pedicures. She enjoyed the massage, the human contact, the giddy giggly ticklishness; being made to feel pretty. As a single lady at her age, she took every opportunity she could get to feel pretty, and pedicures were her favorite.
She got into her sedan, and headed off to work, sipping her coffee on the way. She thought about things while she drove. Cheryl’s morning commute was one way she organized her thoughts; it was time she didn’t have to spend on anything else. She thought about life, about love, and quite often about her job. Today her thoughts dwelled on romance. Cheryl was single, and always had been. She had dated before, a couple of guys here and there, but none of them had that certain something she’d always been looking for. She was quite a catch, too, but at the end of the day, she just couldn’t find what she was looking for.
Her thoughts on the commute threatened melancholy, but she beamed as she walked through the front door of the office, swinging her hips as she walked to her desk. She stopped off to check in with the other girls for a bit, chit chatting, and directing the day’s tasks. Cheryl always liked to organize the girl’s workload by case, and by the Partner they were assigned to. As a small firm, one would think that the filing would be easily managed, but it was its own animal; and animal only Cheryl could properly tame.
She peeked her head around the door to Fred Siltain’s office.
“Good Morning Fred!” she chirped, waving politely.
“Ah, good morning Cheryl! Did you get the filing instructions for the Mitchell case? I set them on your desk…”
“I haven’t gotten to my desk yet, no, but filing is going to be my main focus for today, if that’s alright with you.”
“Absolutely dear, you file away! Lord knows no one else can do it. Just make sure you have your cell on in case I need you. That filing room is like a dungeon sometimes.”
Cheryl chuckled. “Absolutely Fred, you know I always have it on! I’ll just be at my desk for a minute, and then it’s off to file-land for me!”
Fred laughed and waved goodbye to Cheryl, sipped his coffee and picked up the receiver of his phone. “Charles? Yeah. Listen, about the Sanderson hearing…”
Cheryl took the long way to her desk, soaking in the buzz of the office, and catching up on not a little gossip along the way. She straightened the files on her desk, and picked up a stack of empty folders, blank tabs, and a massive stack of loose papers. She bundled all of her work up in her arms, and marched off down the corridor to the file room.
She opened the door to the file room, and took a deep breath. Cheryl absolutely adored that smell. It was that old paper and dust scent of an old-fashioned file clerk’s office, like her mother’s. She loved this room, and its smell, because it was her very own little kingdom in the office. No one could match her filing skills, or frankly understand her methods, and thus she maintained control over this room, and, to some extent, the firm itself.
She plopped down into a chair, and set her files and papers on a small table next to her. For the second time that day, Chery’s thoughts began to drift toward romance. She felt so alone in the world, but no one could ever accept her for who she was. She’d tried everything she could think of, even had turned to the internet, but no one she had dated could ever accept Cheryl’s fetish for tickling. Cheryl loved being tickled, for as long as she could remember. In fact, nothing made her happier than the feeling that ran through her body when she was being tickled. She couldn’t experience pleasure in the bedroom without it, and that was just too much for all of her potential suitors. She sighed audibly as she considered her position in life. Over 40, alone, with an overwhelming need to be tickled, Cheryl just felt consigned to be miserable. It wasn’t all bad though, and slowly but surely, she began to consider the positives. She didn’t have any dependents or much in the way of responsibilities, which freed up a lot of her money to spend on herself. She always had nice dresses, and shoes, and she was constantly getting pedicures. As previously mentioned, pedicures were her favorite, mostly because they tickled like crazy, and they kept her feet nice and soft in case she ever met someone who would be willing to indulge her little fetish. She looked down at her new heels, and wriggled her pretty pink toes, and began to think positively again. It was really a talent of Cheryl’s, being able to stay positive all of these years.
Cheryl got to work, organizing files, replacing folders, re-tabbing and swirling around and reorganizing the room. She lost herself in her work, as she often does, and when she walked out of the file room door, the office was empty. Shocked, Cheryl looked down at the thin silver watch dangling from her delicate wrist, and was amazed to see that it was past closing time. Well past it as a matter of fact, as it was dark outside and only one light glowed from the ceiling. Cheryl shrugged her lightly freckled shoulders and walked over to the coffee machine, unaware of the eyes watching her as she strode. She fluttered her fingers over the K-cups on the rack, searching for her favorite flavor. Her eyes lit up when she saw the blonde roast. She snatched it up and stuck it in the machine, putting her favorite cup in line to catch the hot coffee.
The man continued to watch Cheryl from a dark corner, astounded that someone was still in the office. He had been so careful! His plan had been perfect, and then here was this pretty secretary, all alone, coming out of the file room…his eyes snapped wide open. This was perfect! He grinned as he reached into his pocket and produced a syringe. He prided himself on always being prepared, and this situation was no different. His footfalls were silent as he padded up to the secretary, stirring her coffee, oblivious to him. He was so close now. He could smell her perfume, light and airy. He took a half-breath and held it. His heart was pounding in his ears and a trickle of sweat was trailing down his temple. He clamped a hand around her mouth to contain her scream, and he plunged the small hypodermic needle into her round bottom, pushing the plunger, and pushing her into a deep sleep.
The world was blurry. That wasn’t right, because she never needed glasses. Cheryl opened her blue eyes all the way, stretching the lids to their limits, and fluttered them, trying to clear the blur from her vision. Had she fallen asleep? She was just making coffee, so how could she have fallen asleep? She was back in the file room, that much she knew, but how had she gotten here? She shook her head, trying to clear the questions, and tried to stand. Now she began to truly panic, for now she truly understood her predicament. Cheryl was in a chair, with a belt around her waist, like a seatbelt, holding her cello waist down to the seat. Her arms were spread wide over her head, stretched near to the point of discomfort, and neoprene cuffs held her wrists in place, secured to the filing racks behind her. Her long, smooth, legs were stretched in front of her, and her dainty ankles were similarly cuffed and secured to a chair in front of her. This chair was secured to the chair she was sitting on, so that no matter how she pulled, she couldn’t move a muscle. She opened her mouth to scream, and thought better of it. There was no one here after all, and she didn’t want to alarm her captor into hurting her. Instead, she just softly called out.
“H-h-hello?”
“Ah, y-you’re awake. Good!” the man smiled nervously as he stepped out of the shadows, taking a few steps toward Cheryl. He was about six feet tall, and about the same age as Cheryl. He had dark brown hair, with a touch of grey at the temples and light green eyes.
“Yes, now do you mind telling me why you have me bound like this? Y-you’re not going to….h-hurt me are you?” Cheryl began to tremble, teetering on the edge of terror at his response.
“No miss,” He stated firmly, but politely, his kind eyes narrowing slightly. “I’m not going to hurt you, but you will tell me where to find the Mitchell case file, or you’ll have this to deal with!”
Upon emphasizing the word ‘this’ the man held up an 8” turkey quill feather, and waved it ever-so-slightly back and forth. Fireworks exploded in Cheryl’s brain. Of course she knew exactly where the case file was, she had just filed the Mitchell case away naught but ten minutes or so ago. But he wasn’t going to hurt her, he was going to tickle! The one thing she wanted more than anything, and he was threatening it like a punishment! Cheryl kept her emotions in check however, as she didn’t want to seem too eager and risk him coming up with a different torture for her.
“N-n-no! You fiend! I can’t tell you where it is, it’s too important!” She lied. She knew exactly where it was, and it wasn’t exactly important, but he did exactly what she wanted. He walked toward her feet, clutching one of the heels and tugging it gently off with a slight pop. She instinctively curled and wriggled her pink toes as the air kissed the sole of her freshly bare foot. He hovered the feather over the lightly wrinkled sole of her right foot, wriggling the tip back and forth in the air.
“This is your last chance ma’am, you either tell me, or I’m afraid I’ll just have to tickle it out of you!”
This was obviously his first rodeo. His voice lacked confidence, and he seemed almost…polite? Cheryl wasn’t sure what his intentions were, but she supposed she’d find out sometime soon.
“I-I can’t tell you! Oh please don’t do this! I’m just far too ticklish!”
James Mitchell grinned at her statement, and considered the helpless bare foot of this beautiful secretary. It was soft, the softest he’d ever seen, and completely free of any trace of callous. A small maze of light wrinkles crisscrossed the soles, and five beautifully elegant toes wriggled and swayed in anticipation of the feather’s touch. Her toenails were glittery pink, and they were captivating. He began to slowly stroke the feather from the heel to the toes, giving it his lightest touch.
Cheryl’s eyes popped open wide, and then slammed shut. Her lips pursed tightly together and she buried her forehead in the shoulder of her forcibly upraised left arm. It was singularly one of the most ticklish things she’d ever felt, and she was trying desperately to hold in her laughter. If she played it tough, but no too tough, he might just keep up the tickling!
She was holding it in! Playing hard to get, which James thought was just perfect. His wife was divorcing him for his tickling fetish, and this firm was handling the case. It had been a source of struggle all his life, and he wanted to change the records to show that he wouldn’t have to pay alimony. His horrible soon-to-be-ex-wife didn’t deserve his money. She had been so abusive to him throughout their marriage to deserve another thought from him. So here he was, breaking and entering, something he had never done before, and he couldn’t believe his luck! This was like his greatest fantasy come to life! He increased the speed of his feather strokes, lightly flitting the tip from heel to toes.
Cheryl couldn’t believe her luck! This was like her greatest fantasy come to life! It tickled so awfully, and when he sped up the feather, she couldn’t help but begin to sweetly giggle. She wiggled her toes tantalizingly at him, trying to encourage him to even more intense tickling.
“This woman is unbelievable!” James thought to himself as he watched her gorgeous toes flex and wriggle. It seemed to him like this woman wanted it! He began to swipe the feather underneath her perfect toes. “You’ll tell where the file is miss, but first, you’re going to tell me your name.” He stated with a coaxing nature, quite intrigued by this giggling woman.
“I’ll hahaha never tell you where the fihihihihile is! Eeeehehehee!”
“Fine,” he stated matter-of-factly as he slipped the feather in between each of her toes, “then tell me your name. That’s a start.”
Her giggles turned to laughter as the sensitive spaces between her toes were stroked by the soft feather.
“Hahahaha! No! Ahahaha! I w-wohohohon’t talk!”
He responded by deftly slipping off her other little kitten heel, and now exposing both of her bare feet. He then began to sweep the feather across the soft wrinkles of both soles, targeting the very center of each foot and alternating back and forth. “Come on ma’am,” he prodded “it’s just a name you know.”
Cheryl threw her head back, and laughed as sweetly as any music James had ever heard. Her delicate wrists shook back and forth in the cuffs, and her beautiful feet kicked back and forth as she laughed. Her tortured laughter echoed throughout the file room as the only response to his inquiry. He slowed his feathery torment on her soft soles, and she gasped for breath, giggling, and panting.
“F-fine! It’s Cheryl. Cheryl Innes. Now, no more! I already told you, I’m far too ticklish for this!”
“I’m afraid, Cheryl, that I can’t let you go without that file, and you need to tell me where it is. I’m sorry, but if you won’t talk, you’re just going to have to get tickled some more. Oh, and mine is James, by the way.”
“I don’t think you’re supposed to taaAHAHAHH!” She never got to finish her thought, as James continued tickling the soles of her helpless, wriggly feet with the turkey feather. He knew what she was going to say though, and she was right. He was making mistakes because he was falling for her. She was so pretty, and so very ticklish, and she was making his heart pound in his chest. He dropped the feather and touched his fingers to the silky soles, marveling at the softness of her tender feet. He danced his fingers ever-so-lightly up and down, torturing the beautiful brunette into giving up her secrets.
Her laughter reached previously unknown levels as Cheryl’s poor feet were subjected to James’ tickling fingers. She liked his touch, the feel of his slightly rough fingertips against her pampered soles, the dichotomy of tender touches with fiendish torture. She was in heaven. She laughed earnestly, and begged genuinely, but she never wanted him to stop tickling. This handsome James, she wanted him to tickle her for the rest of her life. She had to admit to herself, as she wiggled in her bonds and begged for mercy, that she might just be falling for him.
“Come on Cheryl, I know how torturous this must be for you. I can see you are really quite ticklish, just tell me where the file is and I’ll stop, ok?” He tensed with anticipation. He really hoped she would never tell, and he could just tickle her all night. He waited with baited breath for her reply, as he eased his fingers into a ticklish trot.
“Ahahahah NEVER! I’ll never tell, James, so do your worst! AHAHAhahHAHAH!”
“Have it your way Cheryl,” he said with a large, pearly white grin. “We really do have all night, you know. Tell me, your underarms aren’t ticklish are they?” He stopped tickling all together, waiting for her reply, and letting his intentions sink in.
Cheryl’s eyes widened, and she audibly gulped as his words echoed in her ears. If there was one spot that could actually make her talk, it was there. She didn’t want their little game to end so soon, but she was just too ticklish under the arms to take it for very long. Her feet were very ticklish, but her underarms were just on another level altogether. Maybe if she begged…
“No! Please James, not that! Anywhere but there, please!” She tugged at her wrist restraints, but they were firm and she wasn’t going anywhere. She was trapped, and her bare underarms were on display for her handsome torturer. She really didn’t want to give in yet, but she may not have a choice. “Oh God. No, please!” Cheryl thought as James’ footfalls echoed, and brought him ever closer to her helpless hollows. He had retrieved his feather, and was twirling it in his fingers. He was so close now, Cheryl could smell his aftershave. She swooned over this handsome stranger, and what he was about to do to her most ticklish spot.
James knelt down at her left underarm, and brought his feather to bear, aiming it at the tender hollow. “Cheryl, I really don’t want to have to do this, (a complete lie, he loved underarm tickling) but I will if you don’t talk. You can spare yourself more torment, if you just tell me where it is.”
“N-no, I c-can’t! I just can’t tell you James! I want to tell, and make it stop, (James wasn’t the only liar here) but I just can’t tell you!”
“Then I’m afraid Cheryl, it’s the pits for you!” He cursed himself inwardly at his corny joke, but he doubted she’d remember it once he started. He began by tracing the rim of her underarm, swirling all around the edges, wondering at the smoothness of her skin. He didn’t dip into the hollows yet, or attack the centers, but continued to trace the turkey feather all around the edges of her outstretched armpit.
Alarm bells sounded in Cheryl’s consciousness, and a cavalcade of ticklish sensations swept over her as he began to play the feather on the outside of her armpit. She knew how bad this was going to be, but she was glad for the teasing, it helped her hold out longer. Still, she couldn’t help shaking her head back and forth, whipping James with her chestnut hair, and giggling with mad abandon. “AHAHAHAH James! No! Please don’t do this! HAHAH! You can tickle my feet all night, or anywhere else, just please not the pits!” Cheryl’s begging was truthful, and James enjoyed the intensity of her pleas.
“Pits?” he mused as he kept up his feathery teasing. “Not what I expected from such a polished and classy gal like you, Cheryl. You must really be serious, if you’re begging like that. All you have to do is talk, and you won’t have to experience anymore of this awful tickling.”
“Do your worst!” Cheryl declared, rather foolishly. She didn’t want him to, but she was so taken by this handsome stranger, that she wanted to experience the full force of his torments. She imagined his hands on her body, and she was swept up in the moment.
“As you wish, beautiful Cheryl…” He turned his wrist so the top of his hand was facing the ceiling, and he lifted his hand to eye level on her. He dropped the feather, and watched it float down to her lap, and rest there gently. His hands then began to move toward her tender armpits, stretched wide open and helpless.
“God! No! James please! Don’t! Don’t!” Cheryl squirmed as much as she possibly could, but there simply was no way for her to protect her pits. Her begging dissolved into hysterical laughter as his fingers made first contact with the silk under her arms. She howled, shrieked, and screamed out with maniacal laughter as her hairless hollows were invaded by James’ wriggling fingers.
He couldn’t believe what he was feeling. The skin was completely devoid of any hair, stubble, or any single blemish. The light wrinkles at the center of her armpits seemed to get the best results, but the hollows that formed from being stretched so tightly were a gold mine as well. James was having the time of his life tickling poor Cheryl’s underarms.
She couldn’t believe what she was feeling. It was so insanely ticklish, and she was nearly cursing herself for having those laser treatments last year. There was no resistance against his fingers, and she couldn’t close her arms to protect her pits. She was on cloud nine, and James had flown her all the way there. She loved how much it tickled, but it was so intense, she needed release. She had to make it stop, she needed it to stop as much as she wanted it to continue. Before she knew what she was doing, she screamed out through her hysteria, “I’LL TALK! I’ll tell you anything, just no more in my armpits! PLEASE! PLEASE JAMES, PLEASE!”
The sincere desperation struck a chord in him, as he heard her screams for mercy. He stopped tickling immediately, and looked at Cheryl with a deep longing. He tucked her hair behind her ears, and listened as she told him everything he wanted to know. When she was finished, he thanked her, retrieved the file, and made to uncuff her arms.
“You know James…you…don’t have to…do that.” Cheryl muttered sheepishly, looking down at the floor.
“What, untie you?” James replied with some confusion, and more than a little hope.
“Y-yes. You could…keep tickling me…if you wanted to.”
“I would love to Cheryl! You mean…you like it? Really?”
“Oh, yes James, yes! I love it! Do…do you like it too?” Cheryl replied, blushing crimson, and warming with hope.
“More than anything! Oh, Cheryl! I thought I was the only one!” James rushed forward and kissed Cheryl deeply and passionately, finally fulfilling his lifelong dream. Cheryl returned the kiss, thrilling at their mutual discovery. James pulled back from Cheryl, and gazed deeply into her blue eyes. “You know, Cheryl, it’s only 2100…we still have all night…”
“Oh tickle me James! Tickle me, and don’t stop until the sun comes up!”
Long into the night, James tickled Cheryl from her nose to her toes and everywhere in between. When it was all over, she showed him how to forge the case file, freeing him from his alimony, and they wiped clean any evidence of his being there. Cheryl stayed over at James’ house that night, and every night after. They lived, truly, happily ever after.
 
Wow! A man after my own heart! Terrific story! I love the interrogation scenario and you did it well!
 
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