Jess Ch. 02

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(This chapter is particularly perverse and nasty, so be warned!)

Jess had been teased by friends in the office as she had every Monday morning for the past four weeks, since getting together with the office hunk. They noticed the big smile on her face when they mentioned Alan, and how defensive she had become over him.

When she started wearing short skirts, almost as short as Dora’s, they were particularly inquisitive. It had been useless trying to keep it a secret, for they guessed then teased it out of her. She hadn’t admitted to moving in with him two weeks ago, though had to confess being an item together.

She had never shared an apartment, let alone her life with a man before. It was easier than she thought it might be, as she smoothly fitted in with his routine. It was so gratifying to hear him say, she was a perfect, respectful woman for it motivated her to try harder to please him. More than that, she was with Alan, the very man her colleagues in the office coveted.

Everyone saw her as a modest and demure young woman, yet she had given her body to him. Her colleagues in the office were young modern women and wouldn’t have been surprised at the two of them having sex out of marriage. The way she smiled, and the clothes she wore, broadcast a clear message, that she was being satisfied. If they discovered what she was doing, it would certainly shock them.

Jess didn’t care what they would think if they found out, she just wanted to be with Alan, and all her efforts went into keeping him happy. She had been shocked when Dora was teasing her about oral sex, but the advice had stuck fast with her. ‘Do whatever it takes to please and keep your man,’ Dora had advised.

That is exactly what Jess was doing. Anything he wanted of her she was dutifully obeying, like the perfect respectful woman he wanted her to be. She didn’t think of their relationship in terms of submission and dominance, just that he was wonderful, and she must do her utmost to keep him.


Jess walked into Alan’s office on Friday with a big smile upon her face. “Good morning sir,” Jess said. “I hope you had a nice weekend?” she politely asked.

“I did thanks, and you?” Alan reciprocated.

“A wonderful weekend, thank you sir,” she smiled in return.

Knowing smiles were shared from having spent most of the time having wild sex.

“You said you have something to show me?” he prompted.

Jess laid a report on his desk. Instead of referring to it she bent over and lifted the skirt. She pulled down the panties and waited with a smile of expectation.

“Well?” he said.

“I’ve taken out the final butt plug sir. I wanted to show you as a surprise,” she giggled. She could feel her asshole gaping at him ready for his cock. He was sure to be pleased as he had bought them and instructed her on how to fit them.

At first it was a shock. To please him she had used the butt plugs, becoming used to the feel of it inside, what once had been a very private place. One after another she had eased larger and larger plugs into her bottom, until the last one had been worn for five days. Her asshole was now stretched for him, to more easily take her, when ever he wanted.

“You’re acting like a slut!” he told her. His voice was quiet and strong.

His official office voice used to discipline staff was used rather than the intimate tone she had come to love. It whipped her into standing before him, like an errant school girl before a school master, more fiercely than if he had canned her bare ass.

“This is no way to behave in the office. Did I not tell you to keep our relationship discreet? Of course it cannot be a secret, but there is no need to go around flaunting your ass in the office, like a street whore,” he chastised her firmly.

He hadn’t shouted at her but the tone of voice was enough of a slap to bring tears to the corners of her eyes. She had let him down, behaved badly and needed to be punished. She felt the knickers pooled around her ankles, dying to pull them up and run from his office, though afraid to make the move.

“You deserve to be punished, don’t you?” he asked with an imperious tone to his voice that demanded only one answer.

“Yes sir,” she said. He was only a year older, though she felt so young and vulnerable it was difficult to think straight. He often did this, leaving her wondering how she had allowed him to treat her so badly.

This time it was her idea, thinking to please him, yet it had ended badly. He was right. Their sex lives couldn’t be brought into the office.

“Get back to your office and get on with your work. I don’t want to see you or your asshole for the rest of the day. Tonight you will be punished,” Alan warned her.

It was a terrible punishment for him to banish her away from him, and that gave her concern enough, let alone worrying about tonight. She bent down to pull up the panties from around her ankles, the action leaving her feeling so terribly belittled.

“No! almanbahis Take them with you, in your hand,” he told her.

“Yes, sir, thank you sir,” she bleated, like a little lost lamb.

She had no pockets to hide them anyway, so as embarrassing as it was, she had to scuttle off to the washroom for anyone to see the panties dangling from her hand. She always wore sensible knickers, though now, wished they were just a little thong that could be hidden in a fist.

Refreshing her makeup helped hide the tears. Everyone was busy catching up on the usual Monday morning demands so at least she got away without them noticing her fretting.

Staring at a report her thoughts were far from it. She had been a good Chinese girl, looking after her mother, then came to Hong Kong with no experience of life. He was right, she was a naughty little slut. She didn’t know how to behave decently. Jess didn’t have the heart to blame him for this uncharacteristic blatant behaviour, and so blamed herself.

She sighed forlornly knowing that whatever punishment he decided on, she would accept it gladly, as long as she could be with him.


Jess got home first, as Alan had a late meeting with the corporate directors. Not seeing him all day meant she didn’t know what he wanted for this evening’s meal, so fretted over what he would say if nothing was ready.

She changed into an outfit bought by him recently, to please him, hoping she had been forgiven. After all she had been showing enthusiasm for something he had done to her. Before meeting him she would have been appalled at the mere mention of anal sex, though now, it seemed almost casually accepted. Not for the first time, Jess wondered what was happening to her.

Her anal tract had been worked hard and she was beginning to enjoy it. She had become a depraved slut, Alan’s dirty little slut, and she didn’t care; Alan liked it and that made it all right. Jess was in heaven feeling his cock buried deep up her bottom pounding away at her prone body.

She still found it humiliating but revelled in the degradation. “Oh! Hell!” she whispered to the empty kitchen. “He’s made me into his little slut and I can’t resist it,” she moaned.

“I’m home Jess,” he announced.

She was startled out of the reverie. The very way he said her name lifted her mood.

He sniffed the air expressively. “Good! You didn’t cook, we are eating out this evening, to celebrate,” he told her. He grabbed her shoulders to tenderly kiss her forehead then wrapped his strong arms tight about her. “You look gorgeous my pet,” he said.

“Now show me you your surprise,” he told her.

From his loving attention her spirits soared. She eagerly bent over the table and spread her cheeks. He put a hand to her crotch with fingers playing over her lips, teasing the already high arousal into wonderful pleasure. He could do this to her with the slightest of touches.

His other hand slowly slipped down her bottom with fingers sliding between the cheeks until reaching her magic hole. She could feel it gaping open for him. She had worked hard with those butt plugs, wearing them all day, even in the office. Every few days she changed the butt plug to a larger one, until achieving what he wanted.

She had stretched it, for him to easily fuck his hole, whenever he wanted it. It was used often, more often than her still tight pussy, but she didn’t mind that much. At first she thought it was to prevent her from becoming pregnant, though soon realised he simply enjoyed buggering her.

His fingers circled her crinkly hole with feather touches, around and around, making her feel giddy with delight. She felt his finger slide into her asshole until his palm cupped her cheeks. There was no pain on entering that magic pleasure hole, it just slid in, but the passage muscles were still there to grip the digit tight.

“The suspenders and stockings frame your lovely ass so well, it looks good enough to eat,” he told her.

Jess giggled. “I bet your cock is ready to eat and I’m hungry,” she teased back at him.

“That can wait. Think of it as part of your punishment. We are going out to eat and it won’t be me, although who knows, maybe,” he laughed.

She didn’t care abut being punished now, on realising it would mean a naughty game, and it was one she had learnt to enjoy. It always ended in a stupendous orgasm, so whatever it was, she was ready. Just so long as he enjoying her body.

“Where are we going, I need to get changed,” she said, still breathing heavily from his playing with her sex.

“No need, you look just right,” he mused.

She was still highly aroused but that wasn’t why she intended to seduce him, or at least not the only reason. After a sex session she could change his mind about taking her out dressed like this.

“This outfit is for the bedroom, it’s too short, and I’m not wearing anything decent underneath,” she complained.

Lifting up the little flared skirt almanbahis yeni giriş she pushed her hips forward to show how easily the panties split open. Before he could say anything she turned around and bent over. She looked back at him, over her shoulder, knowing he could see the gaping hole. It was more than ever his toy to play with.

Of course she couldn’t go out dressed like this. The tight white top was a tiny boob tube, just covering her breasts, and her dark areola showed through it. The skirt poured over her hips, like spilt paint, to float out around her upper thighs.

The panties were a white ribbon of silk wrapped around her hips with two ribbons running between her legs. When the ribbons of silk parted everything was on show. The white suspender straps dug into her dusky thighs, clasping the white sheer stockings tight. The little red bows at each side of the stocking tops were on display with the suspender grips.

“You’ll just have to keep your legs together, you little wet slut,” he grinned at her.

Jess pouted defiantly and almost stamped her foot from not getting her own way. She knew it would be useless to argue, or even resist passively. If this was to be her punishment it would have to be endured. He wouldn’t let her run into colleagues from the office, so maybe it wouldn’t be so bad.


It was embarrassing walking into the restaurant, when all heads turned her way. It was an expensive establishment, with everyone dressed in designer clothes, leaving her feeling even more disreputable. The men looked at her with steamy eyes, telling her they wanted her, obviously thinking she was just a slut, available to anyone. Being noticed wasn’t something she was used to and being looked at in that way was humiliating. The women looked at her with stern looks, as though warning her off.

Alan chose an antique wooden bench in the centre of the restaurant. It was the last surviving part of the previous historic establishment and the only seats left – because it looked uncomfortable.

Jess thought this was a part of the punishment, for she would have to be very careful in the split crotch panties, otherwise she would leave a nasty mark. The look of steamy desire in all those men’s faces added to the arousal, leaving her soaking wet. It would be painfully awful to leave sex juices on the seat, for the waiter to see.

“Wait a moment,” Alan told her, as she began to sit. He guided her with a hand to her hip.

Her eyes widened in alarm as she sat down on the bench. Her knees were bent ready for her bottom to be dropped onto the seat. She felt something hard poking at her bottom.

“It’s alright Jess, sit down, carefully,” Alan told her.

Alan had stuck a large dildo to the smooth wooden seat and she was squatting awkwardly, ready to impale herself upon it. People were already staring at her, thinking she was a whore, available to anyone of them, for the right price. In consequence, her face was a picture of embarrassment. Feeling the hard object pushing between her cheeks, it changed to consternation and dread.

Ready or not she was going to sit, for her legs were giving way in the awkward crouched position. Before they gave way completely, leaving her to crash down upon the nasty thing, she had to lower her asshole onto it with as much control as could be managed. It seemed to rise up and up for such along time, deeper and deeper into her body, filling up her slight frame with a foreign hardness.

At last she sat, tenderly resting her cheeks on the bench, with the dildo right up her ass. A normal thing to do would be to shuffle, for a more comfortable position, but she was impaled there, unable to move.

“There is a suction cup holding it in place, so don’t try to move around,” Alan explained. He had a big grin on his face. “You’ll remember to behave in the office after this, won’t you?” he asked.

“Yes, sir,” she mumbled, still trying to get used to the big thing, stuck right up inside her body.

The white table cloth hid the little skirt from other customers, that had ridden high around her thighs, yet the waiter could easily see her panties. She couldn’t look around the room or at the waiter when he arrived. She knew he was staring at her, as Alan ordered for them both. He knew she couldn’t bring herself to speak.

The food arrived. “You know what I like, so serve me,” he smiled at her.

She looked at the dishes arranged along the far side of the table, and with dread, realised what it meant. Her muscles had clamped tight upon the large hard dildo and it was impossible to move. It was suck firmly onto the smooth bench anchoring her to it. To serve him, she had no choice. She would have to lift her ass off the bench to reach the dishes.

Leaning forward wasn’t good enough she had to ease herself up the length of dildo. Heaving herself up its length, she managed to lift a spoon and start dishing out rice onto his plate. It was o good she had to rest and slid down upon almanbahis giriş the giant appendage.

“Carry on, Jess, I want more than just rice,” he laughed.

Steeling herself to the unnatural inner movements, she half stood again. With the head of the dildo just inside her asshole she scooped up chicken and added sauce to his plate. Again she just had to rest, and eased her aching asshole down its length. Looking at her plate she realised the process had to be repeated for her own meal.

One look at Alan, told her he was waiting for her to dish up her own choice. It was a little easier this time, though still an agony of emotion, and inner pain. No-one knew what was happening to her. That was little compensation though, for she knew. In a restaurant full of strangers she was buggering herself. Surely it showed on her face what she was doing.

Surprisingly she was becoming inflamed with arousal. The little panties were already soaked, and she could feel the wetness overflowing onto her thighs. It was surely running over the bench too, leaving it slick with her love juices. He was either being cruel or deviously sexy. Alan must have planned this during the day, not giving away this devious plan in the slightest.

Jess needed to go to the restroom but put off the hideous prospect of lifting her body off the dildo. Eventually the meal was over and the frightful task had to be faced. She lifted her bottom up and up, for it to seemed as though her whole body was being emptied. The short skirt couldn’t possibly cover that big thing. When she turned round Alan had scooped it up and placed it into the bag he carried.

Earlier she had thought it might be a present for her. It turned out to be a torture instrument. Pleasurable though. Now it was over, she felt that after all, it had been a surprise present. She was so turned on she didn’t think about the slimy thighs, glistening as she walked between the closely packed tables. The skirt was so short it showed off the ribbons on the suspenders and certainly revealed her wet thighs. Now brazen with arousal she just didn’t care what the other customers thought.

“I need to go to the restroom,” she whispered to Alan.

“Do you want to go back through all those tables,” he asked.

“No, lets go, please” she replied. The embarrassment of what the men could see of her body was closing in. Becoming conscious of the wanton sight she presented, brought on a moment of panic, so she just wanted to get out of the restaurant as quickly as possible.

Alan led her outside, to an alley beside the restaurant. “Down there,” he said. Still gripping her hand he pulled her a little way into it. It was a busy street and people were passing the end of the alley.

“You wanted to pee, didn’t you?” he asked.

“Here?” she asked, in a complaining tone.

“Go ahead, or I won’t let you go, until you pee you’re panties in the street,” he said sternly.

Jess crouched down and tucked the hem of the skirt into the waist band. An advantage of the split crotch panties was appreciated now. It could all be done so quickly and efficiently, ready to escape back to the street. Anyone passing could glance down the alley to see her urinating like a dirty bitch.

She successfully avoided splashing her shoes as an agonising, hot splash of golden pee, gushed from her hole. He told her it was that so often, she referred to her love-place, as a fuck hole, or just a hole. It was a relief, but that feeling was only short lived.

“Turn around and face the wall,” Alan told her. “Stick out your ass,” he added.

The skirt was still tucked into the waist band, though so short, it made little difference. She felt his cock nudge her pussy and she whimpered with desire. Surely he wasn’t going to take her here, in this dingy place. It was a back alley, and she assumed he was going to take her back alley.

“You’re my dirty whore, picked up for a quick fuck, in a dirty alley, up against the wall,” Alan loudly said, in her ear.

Jess sighed with delight. Was he really going to fuck her here? She would have thought of ‘making love’, or some cleaner euphemism, but she had learnt to call it what it was, fucking! Especially here, in a dirty back alley, it was just fucking. The smells from the restaurant waste, and her fresh urine, was adding to the nasty odours of the filthy place.

“Yes, sir, fuck your whore. I’m a common whore off the street, picked up for a quick fuck,” she said, while sticking out her ass at him. He demanded more. “Just fuck the whore and dispose of her afterwards. I’m so bad I charge a dollar a fuck. I’m your cheap whore fuck, sir. Please fuck me, I don’t deserve you lovely cock, fuck me, please!” she begged.

At last she felt his cock pierce her lips and drive straight in, deep and hard. She moaned in rhythm with his steady thrusts. “Fuck your whore, sir, punish your whore,” Jess moaned. She was reaching a point of ecstasy when something made her look sideways, down the alley.

She couldn’t see them clearly, though recognising the group of girl’s, arguing over something. They were her friends from the office! If they looked down here they would see her being fucked, like a common cheap prostitute, up against the wall!

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