tagFetishNaughty Naomi

Naughty Naomi

bytoocold©

When people asked Naomi what her job was, she told them that she was a school secretary, which was mostly true. She was a secretary, and it was a sort of school, though in actuality it was the sort of school that she previously assumed only existed in sexy fantasies -- an all-girl institution for ladies aged 18 to 21 who, with complex legal paperwork being signed and validated, agreed to submit to a regime of corporal punishment when the school authorities felt it was warranted. A key part of Naomi's role was to maintain the Discipline Record, a handwritten (to facilitate the signature of the punished) book listing who had been punished, how and for what.

As she was 22, Naomi was technically outside the remit of attendance at the school -- a fact that was a teasing disappointment to her every time one of the students came into the office to report for a punishment. Naomi had long fantasised about receiving exactly the type of punishment discipline that the school dished out. Whilst exploring her sexuality she'd managed to get a couple of men to spank her bottom, but their focus was usually on her boobs and her pussy and they'd never given her what she really wanted which was a long and hard thrashing. At least, that's what she had in mind -- having never felt anything stronger than a light slap across her backside, she acknowledged that being caned might be less fun in reality than it was in her fantasy.

Actually, being punished was one of three key fantasies that dominated Naomi's mind, and was one of two she'd yet to experience. The second was to have sex with another woman. She'd had plenty of men whilst at university -- she was pretty with a wide smile and big, blue eyes, thick, chestnut hair, pale, creamy skin and the sort of curves on her 5' 4½ " frame that no man could resist ogling, with soft, natural 32F boobs, a slim waist and full, fleshy buttocks, so attracting men was not a feat. She'd worried about getting a reputation as a slut (she was right to; she had) but what she actually wanted was a reputation as a lesbian, but she'd never had the courage or opportunity. Now she was away from the insular world of uni, she was determined to find a woman to sleep with.

Her third fantasy was the one that she had actually indulged, and was now more a regular reality than a fantasy. Naomi was turned on by needing to use the toilet, and loved to wait and wait until the desperation to go was physically painful. She loved to sit at her desk, desperate for the loo, crossing and uncrossing her legs, squeezing her thighs together or tensing her bum cheeks as either or both her bladder and bowels screamed at her for release. Of course, the result of waiting until she could wait no longer meant that accidents had happened. On more than one occasion Naomi hadn't quite made it to the toilet once she finally decided to go and had flushed with embarrassment as her knickers were soaked with pee. Twice, both times thankfully at home, it'd been worse and she'd filled her panties with shit too. The fact that on each of these occasions she'd masturbated to glorious orgasms before cleaning herself up was something that Naomi was aware of but ashamed of.

Right now, Naomi was at her desk, enjoying the quiet hour after the students had gone home. This was her favourite time of day, when she could catch up on her work whilst reading the Discipline Record. This always turned her on, and she was aware of the heat in her pussy and the stiffening of her nipples as she read the list of sanctions. Unlike old-fashioned schools with just a cane, the headmistress here, Ms Holloway, liked to use a range of implements. Gently squeezing her thighs together to both put pressure on her pussy and because she'd needed the toilet for the last 90 minutes, Naomi's eyes flicked excitedly down the list on the most recent page:

Philippa R -- tardiness -- third offence -- hand (30 mins), cane (6)

Charlotte O -- swearing -- second offence -- hand (20 mins), hairbrush (12)

Helen R -- tardiness -- fifth offence -- hand (30 mins), paddle (24), cane (24)

Nicola T -- lewdness -- first offence -- hand (10 mins), strap (6)

Natalie E -- poor work -- fourth offence -- hand (30 mins), strap (12), hairbrush (36)

The punishments escalated with multiple offences, of course, and always began with a hand spanking. Naomi sighed to herself as she looked and wished...

Peering through the crack of the door into her office, Ms Holloway was deep in thought, weighing up her experience and belief with the risk of embarrassment. She was very attracted to Naomi, and believed from the stray looks she'd seen Naomi give herself and other girls that, even if she'd not done so before, Naomi would be receptive to the idea of sleeping with a woman. She'd also seen the way that Naomi read the Discipline Record when she thought she was unobserved. In fact, Ms Holloway had spent as much time sitting at her own desk fantasising about punishing and ravishing Naomi as Naomi had spent at her desk daydreaming about being caned and used by a woman. Fortune favours the bold, Ms Holloway mused to herself as she crossed her office to stand behind her desk.

Christina Holloway was 38 years old, and stood 5' 8", although almost always wore at least 3" heels to allow her to tower over most of the students. She'd put on a little weight once she passed 30, she was now about 150lbs, but the extra pounds went on in all the right places and her body was as eye-catching as Naomi's, clocking in at 38-30-39 with a 30DDD or 30F bra. Her sparking blue eyes and fiery red hair, sleekly styled, got almost as much attention from male admirers as her chest, but, like Naomi, it was other women she was interested in. She smoothed the skirt of her fitted business suit, opened an extra button to reveal even more cleavage than usual, and pressed the intercom button.

"Naomi, could you step in here for a moment," she said, crisply.

The buzz of the intercom made Naomi jump and she had to clamp down instantly to regain control of her bladder. Rising from her desk, she hurried to attend to Ms Holloway when the intercom buzzed again. "And bring the Discipline Record" Ms Holloway's voice added. This was a fairly normal request -- it was Friday afternoon, and Ms Holloway liked to review the week's punishments. Naomi enjoyed this as she almost always managed to time it so she was desperate for the toilet whilst she was in her gorgeous manager's office talking about girls having their bottoms disciplined -- almost every week the first thing she did when she closed the door of her apartment behind her on a Friday evening was wet herself whilst masturbating and thinking about this weekly meeting. Little did she know that this week was going to change her life.

Entering Ms Holloway's office and closing the door behind her, Naomi crossed the room and handed the book to her boss. She was turning to sit as she usually did in one of the guest chairs when Ms Holloway spoke up, instructing "Just wait there for a second, Naomi." The brunette did as she was told, her eyes automatically looking down the redhead's blouse at her deep cleavage whilst she read the latest entries. Ms Holloway could feel the younger girl's gaze, and resolved on her course of action. She'd been considering offering a drink and trying a slow and cautious approach, but decided to throw the dice and see what happened. Picking up a pen, she began to write in the book whilst speaking. "Do you like your job, Naomi?"

Naomi was surprised by the question, and her need for the bathroom was starting to overpower her ability to think straight, but she replied, "Yes, very much, Ms Holloway."

"I see, good. What do you like best?"

"Umm...well, it's varied and...close to home. And, of course, I like working with you and the teachers."

Ms Holloway added another note. "And the way I do things doesn't bother you?"

"Oh! You mean...no, not at all."

"Is that why I often see you reading the Discipline Record when you think you're alone?" Naomi looked startled and guilty. "Tell me, what are you reading it for?" Ms Holloway looked directly at Naomi now, who was blushing furiously. Of course, she'd not really done anything wrong but something in her was responding to this situation with a feeling of utter submission.

"I...I mean...nothing, I don't read it for anything...it's just there..." Naomi stuttered.

Making a final note in the book, Ms Holloway sat back in her chair, turned the book to face Naomi and folded her arms beneath her breasts, slightly accentuating her already unavoidable cleavage.

"I'm not sure it is for nothing, Naomi. Why don't you take a look at what I have written and see if you have a different answer for me?" As if in a trance, Naomi leaned forward to look at the book, resuming where she'd last read, where there where new entries:

Natalie E -- poor work -- fourth offence -- hand (30 mins), strap (12), hairbrush (36)

Naomi S -- lying -- first offence -- hand (10 mins), slipper (6)

Naomi S -- lewdness -- second offence -- hand (20 mins), strap (12)

Naomi S -- lying -- third offence -- hand (30 mins), cane (6)

She nearly fainted. Her hand went to her mouth as she gasped, overcome with arousal and panic and confusion and guilt, as well as the now omnipresent need for the toilet. "I didn't...I mean, I'm not lying..." she trailed off.

"I think you are, Naomi. I think you told me lies about why you like the job -- I think it is because you hear me punishing naughty girls all day. I think you look at the book for lewd reasons. And I think you lied to me about that when I asked you. You work here, Naomi, and you know how I work. Just because you're a year older than the oldest pupils doesn't mean that the methods will not work on you."

Every part of Naomi's body felt like it was vibrating with excitement and fear. This was her fantasy, right here, right now. Could she take it? Surely Ms Holloway did not intend to give her three punishments all at once? Could she take that? She'd never even had a proper spanking. "Yes, miss," she finally croaked. "I...you're right, I like the job for the reasons you said. I read the book because it is exciting for me. I just wanted to try it, see what it was like."

"Well, you'll find out what it is like in just a moment, Naomi. But there's no 'trying it' with me. I expect you to confirm like the other girls that bend over for me -- if you agree to this, then you agree to me disciplining you as I see fit." Naomi was so excited that this statement almost made her orgasm -- she certainly felt a flutter in her pussy. She nodded, meekly.

"I understand that, Ms Holloway." The older woman looked her secretary up and down. She was wearing a simple white blouse that stretched over her huge boobs and a black pencil skirt with either tights or stockings below. She was fidgeting slightly.

"Well, then we shall proceed. I suspect that you have listened to me do this many times, Naomi, so you'll know the drill. First, take off your skirt, girl."

Feeling like this was all happening to someone else, Naomi slowly reached behind and undid the zipper on her skirt, sliding it down over her wide hips to drop in a pool of cotton at her feet. Ms Holloway drank in the view, as she could see the 22-year old's underwear now -- her bikini-style cotton panties with white and candy-pink stripes looked sweet and girlish, an odd contrast to her black, hold-up stockings which indented slightly into her soft, round thighs. What she did not know is that as well as battling her escalating lust for her boss and her onrushing fantasy of being punished, Naomi was also nearly at breaking point with her need for a pee. Ms Holloway rose from behind her desk, and walked to stand at Naomi's shoulder. She saw no reason to deny the sexual element of this. She kept it all business with the students, but Naomi was here because she wanted to be.

"As this is your first time, I'll explain what's going to happen. First, I'm going to sit in this chair, bend you over my lap and take down your knickers, Naomi. Then, for ten minutes, I am going to spank your bottom with my hand. I know this is your first punishment, but I don't believe in going too easy, so the spanking will hurt. After that, I will take a leather-soled slipper and smack your bottom with it six times. Six, hard times -- three on each cheek." She paused, enjoying Naomi's silent, squirming acceptance. Ms Holloway's knickers were noticeably wet in the crotch as her own pussy responded to her arousal. "Then, after a short rest, you'll get another spanking. Harder this time. For twenty minutes. If you haven't already, I guarantee that you'll be in tears by this point and will be wishing you'd not been naughty. Then I will bend you across my desk and you'll feel the leather strap on your chubby bottom, a full dozen." Ms Holloway was walking around Naomi in a slow circle, and her heart soared when she saw how Naomi's erect nipples were visibly poking through her bra and blouse. She was hoping for a sexual relationship with her young secretary, and the brunette's clear arousal was a promising sign. "Finally," she whispered now, breath hot on Naomi's neck, "I'll take you back over my knee for another thirty minutes of spanking. This will be the hardest yet, and after the slipper and strap your bottom will be on fire. Then, finally," she paused, her hand idly stroking down Naomi's back, past the hem of her blouse and onto her panty-covered bottom. "The cane," she finished, giving Naomi's ass a firm slap as punctuation. Unfortunately, the slap was not just the end of something -- it was the start.

Startled by the sudden blow and long past desperate, Naomi's bladder gave out in a sudden rush. She made a pitiable keening sound and covered her face with her hands (but made no attempt to move) as her gusset was swiftly soaked with hot, pale yellow piss. The first Ms Holloway knew what was going on was when a rivulet of pee run along the under-curve of Naomi's bottom, spilling down the back of her thigh to soak her stocking as a torrent splashed through the sodden material of her panties to patter on the carpet between her feet. The redhead stood back, briefly shocked, and watched Naomi disgrace herself. As she flooded her panties, more splashed down into a soggy pool between her feet, and streams ran across her bottom and down both thighs, running into her shoes and visibly soaking the front and back of her panties. Naomi began to cry, not the hot tears of pain that Ms Holloway had planned, but gentle sobs of humiliation, as she stood in front of her boss, uncontrollably wetting herself like a small child. Her body betrayed her arousal, though -- you could almost smell the sex in the air and her breasts felt like they might catch fire they were so hot and heavy and her nipples painfully stiff.

Regaining her composure, and more turned on than she'd been in her life, Ms Holloway sat down and said "Assuming that is over, Naomi, we'll start with your punishment now. You can take off your own knickers so that I don't get your pee all over me. And your stockings, you dirty little girl." Humiliated, embarrassed and on the verge of dissolving into orgasmic bliss, Naomi peeled off her pissy clothes. She dropped them into a soggy heap on the floor and went to stand in front of Ms Holloway, hands folded in front of the neat triangle of hair over her pussy.

Taking Naomi's hand, Ms Holloway guided her over her lap into the classic spanking pose, bottom high, head dangling. Naomi's hands were on the floor to aid her balance, her full, un-spanked bottom cheeks, damp with her own piss, facing up ready for Ms Holloway's punishing palm. The headmistress admired the full, round cheeks -- she did like a big bottom to punish. And, unlike the begrudging girls at the school, Naomi was here totally voluntarily. She didn't just deserve to be punished -- she wanted to be. Surely that was all the more reason to make this a hard one. Even before she disgracefully wet herself!

Without further preamble, Ms Holloway glanced at the clock and then brought her hand down hard onto Naomi's fleshy right buttock. Naomi gasped at the sudden sting, but had no time to process the feeling as a similar burst of pain followed a slap on her left cheek. For the next ten minutes, that was Naomi's whole world -- a metronome like series of smacks, one after another after another, covering her whole bottom, top to bottom and side to side in firm, remorseless spanks. The stinging pain built slowly as spank fell upon spanked flesh. She winced and gasped, especially at the ones that targeted the tuck of her bum or caught the tops of her thighs, but she endured it better than many beginners. Of course, she had no idea at this point how much harder Ms Holloway could spank. Then it was over. The hand stopped falling, and the younger woman was able to gather her breath and consider how she felt. Turned on? Definitely. Sore? A bit. Chastised? Not yet. And that was her last thought before a resounding thwack filled the room, and Ms Holloway brought the slipper down with determined force. Naomi cried out as this was much more painful, the wider striking surface of the leather slipper seeming to cover her whole bum cheek with one slap. Five whacks later and Naomi was on the edge of tears, but hung on, biting her lip and ignoring the burning of her posterior for a moment. Following Ms Holloway's command, she shakily stood up and then went and stood facing the wall, hands on her head, aware of the heat in her bottom, the stinging pain, and the fact that her punishment has hardly begun.

Quarter of an hour later, she was back across Ms Holloway's thighs, five minutes into her second spanking. Having been warmed up by the spanking and the slipper, Naomi could feel that her boss was going harder and faster this time, a relentless tattoo of slaps once again covering her whole backside, the full bottom cheeks flattening under each smack before bouncing back, redder than before. As the heat built, Naomi reminded herself that she'd wanted this, dreamed of this and agreed to this. She wasn't a pupil here -- she fantasised about getting a smacked bottom and that is exactly what was happening.

Naomi was whimpering and mewling as the intensity of the pain in her behind grew, and was dimly aware that she was kicking her legs in response to the hardest of the spanks. She could not see her chubby cheeks and so had no idea how scarlet they were. Ms Holloway, however, had a perfect view and was almost entranced by her secretary's shapely bottom, the once-white cheeks now a fiery, painful red. She could also see Naomi's juicy cunt, now clearly wet and pouting from sexual excitement. There was no question that the voluptuous girl was aroused by this. With a glance at the time she delivered one final, ringing slap to Naomi's bottom and told her to stand up. She could see the younger woman's eyes were full of tears, and they'd soon be spilling. They already would if Naomi had felt a proper punishment, but Ms Holloway was easing her into it -- not that the brunette realised this.

"Bend over my desk now, Naomi," the redhead instructed. "It's time for your first taste of the strap." Naomi bit her lower lip nervously, but complied, leaning across the desk, her heavy breasts squashed against the papers there, curvy bottom pointing up and waiting for more punishment. Ms Holloway flexed the leather strap in her hand, stood behind and to the side of Naomi, and raised her arm.

"Aaaaaaooowww!!!" Naomi's scream filled the office as the all-new pain of the strap overcame her restraint. She jumped up from the desk, hands covering her abused bottom.

"What do you think you're doing? You should know the rules, girl. That one does not count. Jump up again like that and you get a choice -- I double the tariff or you can quit and we never do this again." That put the ball firmly into Naomi's court, just so Ms Holloway could check the 23-year old was definitely wanting to be punished.

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bytoocold© 7 comments/ 80377 views/ 45 favorites

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