by MissKateKees

 

There was a brief moment of silence, of pure unadulterated terror for Olly, before the crescendo of hysterical laughing broke out. Steph clasped her hands to her mouth in complete astonishment, Kate looked Olly straight in the eyes, laughing AT him, and Sophie stood there giggling with happiness, her arm fixed on Olly’s naked shoulder in case he thought to make a run for it. The girls had always warned her off this ‘obsession’. She would now show them it was Olly who was obsessed – obsessed with her! He had declared his love and offered himself entirely to her.

“So what the fuck is this?” Said Steph, standing and taking a step forward to scrutinise Olly’s athletic body, with only his briefs hiding his modesty.

“He came around an hour ago beset with passion, he’s declared his love for me!” Sophie forcibly turned Olly’s head and gave him a deep kiss, her arms went behind him for a quick feel of those rock hard buttocks.

“Aw!!” The girls clapped in celebration for Sophie, as she generously accepted the applause, grinning ear to ear.

“So why…” said Kate, leaning upon his shoulder “is he in this state of undress?” Olly twitched with fear, Kate’s incredible looks were now a source of fear and Steph’s piercing gaze didn’t look particularly friendly either.

Sophie recounted the tale:

“I couldn’t stop him! He ripped his clothes off right in front of me and begged that I accept him as my boyfriend. I just about convinced him to keep these on” she pulled his briefs out and let go, slapping painfully back into his cock. “To keep just a LITTLE modesty.”

The two girls broke out once more into outrageous laughter at the vision of Olly manically stripping off his clothes before a startled Sophie and begging for her affection. Olly couldn’t quite believe it. He was about to protest at her tale of him wilfully submitting but…she was telling it with such confidence, had it actually happened that way? He recalled arriving here full of lust, and then removing his clothes before her, and he had screamed his love for her…his head was dizzy, he could no longer think, and resolved to remain silent.

“But why stop there?” Said Steph, growing in confidence. She had never liked the way this brat had led her friend and flatmate on, “take his pants off him.”

Kate bent down to unashamedly inspect his little bulge. “Doesn’t look like there’s much there. So what’s all the fuss about? Take them off him Sophie!” With this she poked at his groin. Olly dropped his head in humiliation, these two were determined to expose him. After all he had done for Sophie, they were going to unveil him anyway for the little dick he was! Their goading grew more vocal and more intense, to the point when Kate put her hands around his briefs, ready to yank them down.

“Stop!” The two halted their teasing immediately as Sophie demanded.

“He’s mine, not yours, he does what I say. I ALONE!” Kate was impressed with this new found confidence in her girlfriend, clearly she had all in control, and Olly well under the thumb.

“You’re the boss.” Steph conceeded, leaving the pathetic figure alone in favour for the bottle of wine on the counter.

“Oh Olly will get that. Sit down girls, I want to hear all about your evening.” Steph and Kate threw a confused look at each other but did as Sophie asked, sitting on the couch with her.

“Olly, be a good boy and open the wine. Then pour. Then that pasta needs cooking and whilst we eat you can clean the toilet.” Steph guffawed at Sophie’s outrageous requests, but all the girls broke out squealing when Olly merely turned around and followed his orders. Sophie sat back and laughed.

“He loves doing the chores for me!” She said with a grin, reality was now hers to fashion “He begged and grovelled to let him do it! He wants to be my house husband in the future.” Kate and Steph watched on in amazement. Clearly the boy was besotted with Sophie and would do anything for her. “Where can I get a man like this?” said Kate.

“If you’re nice to me I might just help you.” Sophie giggled, even the girls were looking up to her. In the past Kate had always had the pick of the boys, but she wasn’t the one with an obedient male servant, willing to do anything for her. As Olly walked back to the couch with the bottle and three glasses he felt three pairs of eyes devouring his near naked body. Reaching across to hand Kate a glass, Steph gave his arse a hard slap “on with it you stupid boy!” Olly looked to his mistress for redress but she merely laughed in his face.

“Oh do get on with it Olly! Stop flaunting or I’ll have those pants of you so fast…”

With this threat Olly now understood his position. That evening he dutifully went about his tasks as the girls went through three bottles. The sexual lust he had briefly shared with Sophie had now disappeared. There was no longer any hint of eroticism or desire in her tone, she simply commanded him as he went about his list of tasks. On serving the girls dinner, Sophie pointed him to the bathroom. As the severely intoxicated girls toasted Sophie’s success, Olly fell to his knees before the toilet bowl. The tiled floor was cold and Olly shivered as he tried to make sense of his position. In what must have been less than an hour he had gone from anticipating sex to a half-naked underling, serving the girls he had once looked down upon. He felt hate grow inside him for Kate and Steph. While he hoped Sophie did this to him out of love, these two bitches seemed to cruelly revel in his downfall, and seemed determined to push it further. How they had started to order him about and threatened to take his pants – and with them what was left of his dignity! That was only for his mistress. That beautiful girl who was both his entrapper and his saviour. He only had to serve her and the pictures would remain their little secret forever. He felt a shadow upon him, she stood in the doorframe, frowning at this lazy boy.

“You’re not doing what I asked. When I order – you do! Honestly Olly! How is this relationship ever going to work unless you do what I say?! Do I need to rob you of those pants to make you see sense?”

Her voice was near hysterical, Olly was petrified, he couldn’t let Kate and Steph see his poor little penis, he’d die of the permanent humiliation, they would never let him forget it and ensure everyone knew he wasn’t the man he proudly posed to be. Desperate to please his mistress, he crawled towards her and began to kiss her feet.

“PLEASE forgive me mistress?”

Sophie was so irritated, why did he have to make everything such a chore. Why would he try to disobey her like this?

“Go get your clothes, I’m so angry I done with you for tonight, I’ll call you tomorrow.”

As Olly hurriedly changed on Sophie’s doorstep (Kate had forcibly refused to allow him to dress in the flat) he was overcome with remorse. He had angered his mistress. He bitterly regretted not throwing himself into his cleaning duties without hesitation. Then he wouldn’t have disappointed her. On returning home Olly immediately shed his clothes. Kneeling naked down beside his bed, he fantasised over kneeling before Sophie and kissing her shoes, barely ten strokes in and he erupted with ecstasy. It was even better than last night’s wanking session, Sophie had awoken a new level of desire in him. He tried to sleep but Sophie’s gorgeous body filled his mind with both lust and guilt.

*

Tessa noticed something odd in Olly the next day. He made no attempt to boss her about and shuffled around meekly as he went about his work. Even Marie had remarked on her employees’ strange behaviour and had asked him if he needed to go home sick. Tessa didn’t care what was wrong with him, she preferred this docile version to the usual chauvinist she had grown to hate. As the doorbell rang, Tessa went to open it.

“Hi Sophie!”

Olly twitched at the name. Looking towards the door he saw Tessa, chatting away to his mistress. He didn’t quite know the extent of their acquaintance but it filled him with dread. As Sophie marched into the small office, Chiara and Marie went over to greet her. Their quiet little office rarely got visitors, it was only a small business, Marie had left a larger management consultancy to form her own, Chiara and Olly were her only permanent staff and Tessa held the only internship offered. As the girls kissed cheeks and exchanged pleasantries Olly sunk low into his desk chair. Why was it women always seemed to have some secret affinity with each other? Why had Sophie come here? Surely she wasn’t going to make an example of him in front of the female staff? His neck twitched as he fiddled with his scratchy collar, he longed to take it off.

“Aren’t you going to greet me darling?”

Sophie’s words confused the girls, were Olly and Sophie dating? Stumbling to his feet, Olly slowly walked over to her, all eyes on him. He stopped before her, unsure as how to proceed. She wasn’t going to make him kiss her shoes right here in the office – was she? Sophie leant in and kissed him. Deep and long, just so there was no confusion from the girls that he was hers. Tessa exhaled in surprise. Olly was always acting the macho bachelor but in actual fact he was Sophie’s boyfriend! Marie smiled at the loving sight, from what her friend Hilary had told her, Sophie was a lovely girl, she seemed like she could get Olly to settle down.

“I hope you don’t mind Marie, but I was wondering if I could whisk Mr. Big here away ten minutes early?”

With Marie’s permission, Sophie took him by the hand and led him out the office. Marie shared a puzzled look with the girls, Sophie certainly seemed to know how to handle him. Tessa considered if Sophie’s nickname for him – Mr.Big – had a hidden meaning…

Olly sat silently, holding hands with Sophie on the train home. She was gazing out the window, smiling happily. Was she planning a repeat performance for her flatmates again?

“Will, will they be there again?” Olly was scared to ask Sophie a question, but his quivering dick demanded to know what ritual humiliation they had in store for him.

“Oh we won’t be going back to mine, Hilary’s invited us both over.”

Olly’s heart sunk at the news. Hilary! He had completely overlooked his last dealing with Hilary since Sophie had taken over his thoughts entirely. It was that wicked bitch that had arranged all this in the first place. He brooded on his situation, recalling her hurtful kicks, her forced photo session, her demand that he crawl for her. Hilary had forced him into this state of submission. Feeling sorry for himself, sick of it all, he tried to wrestle his hand free from Sophie’s but she merely grabbed him tighter. She threw him a look of annoyance that instantly quashed any thoughts of resistance on his part. Olly bitterly noticed that Sophie didn’t look anything as good as she had last night. She was wearing a rather frumpy sweater and a long checkered skirt. Though the heels remained. And yet despite her now dowdy appearance, still Olly felt attraction to her, he wanted to forcibly strip her down, turn her over and fuck her hard from behind, where he’d be in charge.

By the time Sophie had dragged Olly to Hilary’s it was getting dark. On answering the door Hilary embraced Sophie with a long hug, beaming with happiness at her buoyant young protégé. As she turned to Olly her faced turned to one of menace.

“I knew you couldn’t resist her!” Hilary and Sophie sniggered as Olly looked to the floor.

“Please go through Sophie, tea will be served shortly. Olly stay there.” She said it as an order, not a request. Olly couldn’t believe the presumption made upon his mistress and yet Sophie went along with it, with a kiss to the cheek, she abandoned Olly to this tormenter.

“Now boy. I hope you’ve learnt a thing or two. First things first, don’t you dare come into my house wearing a power suit. Take it all off right now.”

She stood there, hands on hips, fully expecting Olly to get naked on her front-door step. He considered calling to Sophie for help, but Hilary’s ice-cold stare filled him with dread. The last time he’d resisted she’d taken everything from him. Every shred of dignity! And she had taken it with ease. He knew he couldn’t compete with her. Slowly fumbling with his clothes, he felt utterly dejected. As he removed his shoes he stood there, shoulders slumped, stark naked in front of this imperious woman, right on her doorstep where anyone might see. Hilary took a moment to grimace at that impertinent little cock before kneeling down and gathering up his clothes. She casually threw them into a bush nearby. “You can retrieve those after you leave.” And with this, she grabbed his ear and marched him into the house and through to the kitchen.

“Here’s the pot, get a tray and serve us.”

Olly newly awakened subservient nature took over. At least when he was working for them the women generally left him alone. Arranging the cups and the teapot onto a tray, he dutifully took it into Hilary’s salon. The two of them were sitting on the couch, transfixed on some folder between them. Despite his hands shaking, Olly managed to place the tray down onto the coffee table, and stood patiently for further orders. Sophie caught his eye, and glanced to the floor with annoyance.

Sensing her intention, Olly fell to his knees, head down before his mistress.

“Do you want a peak Oliver?”

Hilary pushed the folder before him. The nightmare returned to him as he gazed upon Hilary’s own photos from that fateful day. His naked state, enshrined for eternity in various demeaning postures.

“I think it’s some of my best work. I wanted to title them ‘vulnerability’ for an exhibition but your dear mistress here has persuaded me against it. For now.”

Olly looked up slavishly to Sophie, he wanted to thank her for protecting him from Hilary’s proposed public humiliation of him, but he struggled to speak the words. Sophie ruffled Olly’s hair with a smile, and with her foot gave his penis a playful little push.

“Which reminds me.” Said Hilary “I have a present for you both.”

Sophie’s eyes betrayed a moment of doubt as she quickly looked to Olly. He in turn looked to his mistress for guidance. Did she know something about this? Sophie’s look for him was almost of sympathy as Hilary returned with a little box complete with a bright pink bow.

“Now I know this is a big step for you Sophie but it will really help young Oliver here. I suggest you do it for him.”

Olly was completely lost, was Hilary actually doing something to help him?

As Sophie opened Hilary’s present, she shuddered and gasped with what she found. From his position on the floor, Olly struggled to see inside. Slowly holding out the box before him, Olly nearly burst into tears.

No. Please NO NO NO! Within the box was a small steel cage, complete with a small padlock. Hilary smiled at the scene. It was one of delicious pleasure, seeing the stupid boy slowly realise what his future entailed.

“All loving relationships should start with this if they are to truly last. Men can’t control their base desires so it’s only right the female in the relationship takes charge. Both of him, and his penis. Think of how tranquil your lives together will be. Oliver will never cause an argument, nor disobey you, because you now own him entirely. He will, cook, clean and serve. Oliver, think of the happiness that you wearing this will give your mistress. Think of the relief of never having to worry about your micro-dick ever again.”

Olly couldn’t believe he was hearing this, he looked to Sophie for some sanity but was shocked to see her looking bright-eyed at him.

“Well Olly? It would prove your love to me. You said you loved me, don’t you want to prove it? So you will put it on yes…YES?”

He was now sobbing as he desperately shook his head. Hilary had first stripped him of his clothes, know she was going to lock him into chastity, and into life-long servitude to Sophie. He would not allow it.

“How dare the boy!” Hilary was teething with anger at his ungratefulness. She was offering him the chance to secure his love forever in a very permanent statement of submission. She had even gone to the trouble of finding an extra-small cock cage to fit his soon to be worthless dick.

And now Sophie began to tear up, pulling Olly up to her she looked him in the eye.

“You said you loved me! So why would you refuse this Olly? Don’t you want me to control you forever? Hilary says quite a lot of men are now wilfully surrendering themselves to stronger females. It’s not a big deal! It’s not like it’s a lot to ask!”

Olly scoffed at the incredulity of the statement! Why on earth would he want his cock locked up? He’d spent most of his recent free time wanking furiously; Sophie made him so hot, how would he survive a lifetime under her without regular release.

Sophie pushed his head into her ample bosom as she made soothing noises, stroking his hair: “Just try it on my love. Please, for me. Just see how it feels. And if you don’t like it then maybe you can take it off yes?”

Hilary had lost all patience for this. Olly had already submitted to Sophie, he couldn’t be allowed to go back on what a modern relationship required; total male submission and acceptance of female authority. Smashing the coffee table aside, she stood and grabbed Olly’s hair. With her other hand she grabbed his balls and squeezed so hard Sophie was terrified she was going to rip them off.

Speaking into his ear, Hilary told him how things would be, “I’ve had enough of this little macho! You ARE going to be locked into chastity and you are going to thank your mistress for doing it! You’re embarrassed? I DON’T CARE, you do not have the right to be embarrassed. That little cock no longer belongs to you, it belongs to Sophie. You resent us for this? You should be grateful that we have relieved you of this embarrassment of yours.” With this final upbraiding of Olly she threw her foot into him. God it felt good to bring down this arrogant boy! Perhaps she’d ask Sophie to let her take her frustrations out on him from time to time. There were further depths of humiliation she longed to inflict on this boytoy.

Affording him no time to recover, Hilary grabbed him by the hair and dragged the quivering wreck before Sophie.

“Now Oliver. Do not try me again. BEG Sophie to take you into chastity. Beg her accept this pathetic cock of yours.”

Sophie sat mouth wide open as Hilary firmly held her love in place before her. When Hilary had revealed this plan to Sophie she had considered it a step too far, but if Olly actually wanted it, if he were to actually admit to it…

Olly wriggled with pain as he felt Hilary behind him shove her fingers up his arsehole.

“PLEASE!”

Sophie kissed him on the forehead, “yes what is it you want honey?” she began to massage his penis slowly, he gasped with pleasure as she began to rhythmically stroke his limp cock.

“Please do it! I’m – I’m yours, take me! Please Sophie!” Olly no longer knew what he was doing, the pleasure from Sophie was coupled with the sensation of Hilary’s invasion of his arse.

“Very well.” Sophie locked lips with Olly and stuck her tongue deep into his mouth. He groaned in pleasure as he felt Hilary remove her fingers from his arse. He clasped onto Sophie’s tits revelling in feel those firm beauties. He felt his cock twitch as it was harshly massaged. It was being pulled, he felt cold metal against it.

And then heard a click.

Sophie immediately stepped back and looked down towards her prize. Olly looked puzzled as he saw Hilary kneeling before him grinning with victory. His little dick had disappeared. It was now locked away in the small steel cock cage. He howled in disbelief as Sophie stood before him, in obvious delight over what this meant. He had devoted himself to her utterly! It had been his choice, Sophie hadn’t forced him. He had actually wanted to surrender his penis to her.

Hilary stood up to take in the sight. She had always known Oliver had secretly wanted to give his dick away. He had been so ashamed of it, Hilary had resolved to step in and make it so. And yet for some reason Olly certainly didn’t see it that way. He meekly sat on the floor crying as he looked down to his caged manhood. There was no return from this. Sophie had him forever. Sophie herself was confused by Olly’s reaction.

“I’d thought he be pleased! This is a happy day for us?”

Hilary took the young girl in her arms and gave her a comforting squeeze.

“He’s a stupid boy. He doesn’t know how to handle his love for you. You have to take control from now on.” With this she brandished a small key aloft.

As Sophie tied the key onto her necklace, Olly looked on in a daze.

“Now. I’ll keep a spare key with me, just in case you lose yours. And there’s a third one here.” Hilary held it before Olly. For one senseless second, he actually thought this was to be his key. He was already planning to take this monstrosity off and force Hilary to suck his dick.

“Now you say he works only with women?”

“Er, yeah that’s right.” This was the moment Sophie was most worried about. She knew Olly secretly wanted to surrender himself to her but this would be a different matter…

“Well one of those girls should have this key so as to keep him in line at work.” Olly grew even more light-headed. Sophie couldn’t be about to agree to having him effectively enslaved by chastity at work. The women would mock him into oblivion.

Sophie looked at Olly with pity. It would be too cruel to let Marie take control over him like that. She knew he had some irrational issue with working under women in an office environment.

“Not his boss. He wouldn’t like that.”

Olly sighed with sheer relief.

“His secretary, Tessa. I know her, she could hold onto it for us.”

Olly crawled up into a ball before them. Tessa! That intern bitch, given command over his cock. He’d treated her like shit, he just knew she’d take revenge in the most shameful way possible.

“Please Sophie! You can’t! Not Tessa please! She works UNDER me!”

Hilary wasn’t having any of it “An absurd situation. A young woman working under a boy like you? We’ll have to discuss this with this Tessa at some point.”

As Olly laid on the floor sobbing, Sophie and Hilary spoke of the new arrangement. After sending him to bring them a bottle of wine the two schemers sat on the sofa drinking, completely ignoring Olly, who remained stationary on all fours. As Sophie drained her glass, she stopped and turned to him.

“It occurs to me that you haven’t thanked Hilary for her present.”

Hilary gushed at the young girl’s suggestion, she was really getting the hang of this.

“Come and make your gratitude known.” Sophie said in a raised voice, it was a command, not a request.

This was too much. They actually expected him to THANK Hilary for locking up his cock? They were acting as if this was all his idea and they had merely been kind enough to oblige. Yet remaining on all fours, Olly crawled up to them. Sophie threw him a scowl, was he deliberately trying to embarrass her in front of Hilary!? Hilary herself stared down at the boy, one eyebrow raised in amusement. Hate, anger, rage! Olly could not sort his thoughts for this bitch of a woman…as he lowered his head to kiss her infamous red heels.

“Get licking, there’s plenty to do down there.”

Sophie laughed at Hilary’s chastisement of him as she gazed upon the beautiful naked body on all fours before them. He licked away at Hilary’s heels for a good ten minutes until she kicked him aside. As Sophie gushed her final thanks and goodbyes to Hilary, Olly remained naked, caged and crouched with his head down. He was sure to keep silent, vision fixed on the floor.

Effusive goodbye’s over, Olly was jolted into action by a kick to the arse courtesy of Hilary and he rushed on all fours to keep up with his new keeper. Hilary felt pure joy at the beautiful sight, as Sophie marched out into the night whilst her beloved slavishly followed on his hands and knees.

“Sophie you can’t someone will see us!” Halfway down the front lawn, Sophie stopped and scowled at him.

“And just where did you leave your clothes silly boy?”

“Hilary threw them into that bush!”

Sophie sighed. Why was he intent ruining their fun? But she supposed she didn’t want her new boytoy being taken away by the police for public indecency, and so reluctantly gave him leave to frantically retrieve his clothes. On returning to Olly’s flat, Sophie took a good long while to survey this former bachelor pad. Obviously the furnishings would have to change to her own feminine tastes. Looking at Olly cowering before her she titled her head to one side.

“Are we forgetting something?”

He grudgingly removed the clothes he had only just reclaimed. Onto his knees, once more he crawled up to kiss his mistresses feet.

“Yes yes enough of that” She nonchalantly kicked him away, as she noticed Hilary had done earlier. Secretly she loved seeing him on all fours before her, passionately kissing her heels, but she wouldn’t give him the satisfaction of knowing.

She gently sat Olly down on the coach with her, it was the first time this evening Olly had been asked to do something other than grovel on his knees. He cozied up beside her with enthusiasm. He had done all that she asked and now they were alone in his flat they were finally going to consummate this relationship. His caged cock began to strain painfully against the harsh steel in anticipation of release.

“Now darling,” she said softly, putting her arm across his shoulders, “what Hilary suggested actually makes a lot of sense. It can’t be right for a man to serve a women at home whilst bossing a girl about in the office. How is that fair to Tessa? So I’ve decided, as I can’t be there to look after you, that Tessa will be given a key and asked to mind you in the office.”

She said it in such a matter of fact way that Olly couldn’t quite believe this conversation was actually happening. After being forced into this damn relationship with a frumpy girl he despised, he was now sitting here, naked, in a cock cage, being told his bitch of a secretary was going to be given complete power over his penis. For the next fifteen minutes, he begged at Sophie’s feet, he cried, he screamed, he tried to argue, and in a fit of desperation he even pleaded that his boss Marie be given the key instead. But his entrapper was not having any of his petulant whinging, she was beginning to see now why Hilary treated him with such little sympathy, only discipline seemed to have any positive impact on him.

With her best Hilary imitation, Sophie tried a heeled kick into his balls – and was delighted that she missed the chastity device whilst hitting him square in his unprotected bollocks. That brought an end to the discussion. As he writhed on the floor in pain, she told him how his new life would be:

“Put your misogynist posturing aside Olly, from now on, you serve women, not the other way round. You’ve walked over girls for years, well now we get to have a laugh at your expense. Tessa will have my permission and authority over you and you don’t get a say. Maybe now you’ll be a little nicer to her: she’s told me some worrying stories about your chauvinism in the office. Now I’m taking your bed tonight, you can sleep on this sofa.”

“Mistress please! When will this be taken off?” Olly held his little cock cage and looked pleadingly towards her.

Sophie was sick and tired of his moaning, the cage was meant to have put an end to that, but instead he was becoming even more petulant and insufferable: “Honestly Olly you’re so ungrateful! It was you who wanted it on in the first place! Hilary has suggested a brief removal of the device once every four weeks, at least to start with, but only if you behave. I’ll also be checking with Tessa whether you’ve behaved at work. If not, it won’t be coming off at all!”

Once in every four weeks! He didn’t think he’d survive a day without wanking over Sophie. Despite his resentment for her, he still lusted after her luscious body.

“And there’s something else. I was disgusted by your behaviour towards Hilary. After all she’s done to help you! It’s like you’re not even thankful! You seem to forget Olly, you wanted this. Now thank me for accepting you.”

Olly stared in incredulity. His cock had been taken from him, his freedom to masturbate, and he was now expected to be servile to these scheming women. It was every boy’s worst nightmare. And yet she was suggesting that he thank her for it! Instinctively holding his testicles for protection he instead begged again.

“Please mistress, I can’t survive this. You have to take it off. You said if I didn’t like it I we could take it off. You said so!”

“And what about my feelings Olly? I rather like it on you. A shiny steel prison for your penis! As well as reminding you of your commitment to this relationship it will also help re-educate you into humility before women.”

Humility before women! Olly couldn’t bare the idea of being treated like an inferior to them. He’d always celebrated male dominance. But here he was, completely at the mercy of the girl he had once considered beneath him. “But I can’t possibly go four weeks without a wank! I’ll even do it for you, at your feet. Please!”

Such an ungrateful display. It seemed he still harboured some lingering ego. Sophie took her time considering the cowering boy before her before deciding upon the simplest way to shut him up.

“Five weeks.”

“Sorry mistress I…”

“Six weeks.”

The idiot finally realised what was happening. He was now up to six whole weeks without release. His pitiful attempt at resistance had just bought his cock another two weeks locked up. He bowed his head in an attempt to hide his impending tears from Sophie. She left him to his shame, as she went to claim his bedroom as her own. Retreating to the couch, Olly laid down on the cold leather and inspected his chastity device. The lock was metal and the steel seemed impossible to break out from. He didn’t want to accept this was happening. He was in his own apartment, and yet nothing was now truly his. Sophie had so effortlessly taken everything from him. How could he possibly resist someone who only had to utter ‘one more week’ to put an end to all arguments? As he curled up on the couch, his hands meekly cupped around the device, he hoped the morning and his impending encounter with Tessa would never come.

*****

Throughout the morning train ride, he squirmed in discomfort. His thick pubic hair kept getting caught in this damned cage. And none of his underwear fit over it, forcing him to go commando. A moment of blind fear overcame him as he walked into the office. He and Tessa were usually the first in and sure enough there she was, sitting in his chair, at his desk. She displayed no obvious signs of knowing. She bit her lip as she attempted the crossword. Concluding that Sophie couldn’t have possibly spoken to her yet, Olly endeavoured to appear completely normal.

“Morning Tessa. You’re erm, sitting at my desk again.”

Tessa looked up with complete disinterest.

“Coffee.”

“-Thanks Tessa I’d love some.”

“You don’t seem to understand sir, I want you to make it for me.”

As Tessa swung in the swivel chair nonchalantly before him, Olly spotted something that forced his balls back into him with fear. Around her neck was a silver chain, and hanging of it was a small key. Retreating to the kettle Olly tried to take his mind of it, but it was definitely a key. Had Sophie already got to her? He would not yet believe Sophie would actually be so brazen in her actions.

Walking slowly back to Tessa, cup trembling in his hand, he placed it before her. She let him wait nearly a minute in trepidation before picking it up to slowly take a sip. Turning to look at Olly, she gave him such a mischievous grin that Olly now released it was already over. Sophie must have told her everything.

“Not nearly strong enough!” she yelled as she threw the cup of hot coffee into Olly’s groin. He doubled over in shock, the searing heat from the coffee scolding his sensitive dick through his soaked trousers.

“Now look at the mess you’ve made Olly. Take those off mister.”

The pain and anguish was too much, he remained looking down, refusing to acknowledge the demand. But Tessa wasn’t having any disobedience, she was only just getting started as she grabbed his thick hair and pulled his face towards her. She wanted to see his will break utterly as she gave him the sweetest of smiles.

“Trousers. Off. Now.”

With that she reclined to watch the show, playfully twirling the little key on her chain. Olly could no longer stand the scolding pain, his unzipped his trousers and shamefully stepped out of them.

Tessa burst out in a raucous laugh, what happened to so-called Mr Big?! The little cock cage was all that Sophie had promised, he looked absolutely ridiculous, standing there sullenly in a suit and tie but no pants. She grabbed her phone and before Olly knew, the camera flash blinded him.

“There. Now go and attempt that coffee again. You are at least capable of that aren’t you?” Tessa smiled smugly at the comical picture that was definitely going as her desktop wallpaper. Should Sophie ever lose heart and release Olly from his chastity, she now had something to continue her hold over him.

“But what about my trousers?”

“-Well you better just hope they dry before Marie and Chiara arrive.” With this she gave him a cheeky wink and giggled, she couldn’t believe how fun her life was about to become.

Olly didn’t like the sound of that and knelt to pick them up, but Tessa was too quick for him, snatching them from his grasp.

“Please?!”

“-Certainly not!”

As Olly tried to grab them Tessa dodged to the side and dashed past him to the other side of the office, waving them above her head whilst cackling at Olly’s misfortune.

“Please?!” Olly charged forward but Tessa got past him again, looking back to enjoy the sight of his little cock cage slapping up and down as he clumsily ran. Laughing uncontrollably and as an obvious threat, she held his trousers out of the open window.

“I asked for coffee Mr Holland. Go make it or I suppose you’ll be introducing mr little dick to Marie and Chiara!”

Olly realised this girl had defeated him. So easily and utterly. Just as Hilary had found it all too simple. Barely ten minutes into the working-day and she had him by his cock. These cunning, self-assured women were running rings around him. What power he once thought a dick gave him, the supposed ‘dominant’ gender, clearly didn’t measure up to much against these conniving ladies. His youthful victor whooped in triumph as he sloped back to the kettle, but not before she smacked his arse hard with a slap, just as he had once done to her, role reversal was such sweet revenge. When he returned with another cup, Tessa paused to think of his predicament. Sophie had merely asked her to ‘keep him in check.’ But that could be widely interpreted… Resolving to move ahead with her own little plan she pressed print on Olly’s laptop.

“I bet you want your trousers back don’t you? Marie and Chiara are usually in by now.”

Olly nodded his head sullenly as he tried to hold back tears. Of course Tessa wasn’t going to settle just for that, he hadn’t even begun to make amends. Swinging in his chair she thought how best to tackle this snivelling wreck. Luckily for her, Sophie had already extolled some good advice on how to control this silly boy when they had met early that morning for coffee at Sophie’s request. She placed her foot forward and waited.

“I haven’t heard an apology yet.”

Olly impulsively collapsed to the floor and did what he did best, he zealously kissed Tessa’s left foot as she viciously pushed her little pump into his mouth.

“I SAID I haven’t heard an apology yet.”

Olly tried but failed to utter his profuse apology as she drove her foot further into his mouth. Though she quickly bored of his slobbering. Standing up before him she waited in expectation.

“Tessa..” he began, consciously aware that at any moment, Chiara and Marie would walk in to find him kneeling before the intern wearing a chastity device. He wanted to tell her she was a devious little bitch, that she was a plain-faced slut with zero talent,

“You’re so gorgeous, and so smart. I’m — I’m not worthy to have such a confident woman serving under me. I’m so so sorry for how I treated you. I only did it because I -” he paused searching his true feelings.

“Because I was afraid of you.”

Tessa had suspected it all along. He was obviously the type of misogynist who was secretly terrified of strong, confident women, probably because he knew what would happen if they were ever to discover the disgraceful size of his cock. Sophie had explained all this morning. How a conflicted Olly had surrendered himself to her and how vital it was that the women in his life now help him come to terms with his true subservient nature. She had explained Olly’s new predicament with a hint of affection and sympathy – but Tessa wasn’t in the mood for sympathy. Olly didn’t need to be ‘helped’ along to his new role, he needed to be systematically humiliated by every woman in his life until any misogynist-fuelled resistance had been broken entirely.

“Go and get that printout, there’s a good boy.”

Olly couldn’t give a damn about her printout, he needs his trousers back on now! Why wasn’t his grovelling apology enough to satisfy her? As he returned to Tessa, he instinctively held the sheets of paper down to shield his modesty. Tessa snatched them with a flourish, complete with a venomous look as if to say, don’t even try it.

“Now then,” she began in a very matter of fact way, arranging the papers.

“What we have here is your full and frank appraisal of me that I’ve taken to trouble of drafting for you. Just like as I do most of your work for you. Oh gosh Mr Holland! You’re so kind in your praise. Oh wow! You actually recommend that Marie takes me on for the open position!”

Olly looked at this tomboy bitch with bemusement “what open position?”

“What with you desperately seeking a secretarial role, now that you have too many commitments at home with Sophie, there’s an open position for junior account manager.”

It took Olly several moments to understand Tessa’s little game. It slowly dawned on him with horror. She was actually asking him to recommend his own demotion. To serve her? As a secretary? An invitation to watch helplessly as she took his rightful position in the office from him; swanning around in her little skirts and frilly blouses as he was forced to make coffee, to take her calls; serving a girl? She had gone too far now, she’d surely overstepped what Sophie had asked of her. He clinged on to this last remaining hope.

“Sophie wouldn’t allow this…”

Tessa was taken aback at this rebuke. A realisation that she was running out of time urged her into action. She may never get a better chance to escape this internship, to make something of herself. And all that stood in her way was a little locked-up cock. Moving quickly, she summoned what strength she could muster. Wrapping her arms around his hunky shoulders she tried to push him down onto the desk. A moment of terror overcame her when she released he was resisting, she could barely move him, he was still too strong for her. Grunting and panting she continued to try and force him to lie on the table but her feminine frame could do nothing against those strong manly muscles.

“Just do it!” she cried, exasperated and desperate. She was losing her hold over him, all hope for the future were slipping away. Olly was shocked by a rare surge of pride, he had defied her! The little woman had tried to force him and he had defied her! All his resentment for his new predicament came spilling over, for what the devious women had done to him, for how Hilary and Sophie had colluded to cage his cock, he threw his hand across Tessa’s face in an almighty slap.

They both stood frozen in silence, shocked at Olly’s moment of violence. Tessa stared at him, mouth open, clutching her aching cheek. Tears swelled in her eyes. She looked so small and fragile to Olly, so scared and hurt as the tears began to roll freely down her cheeks.

“Tessa…Tessa I’m so sorry-”

She smashed her knee up into his caged cock. Beset with fury, she threw two sharp kicks into the little cage. As he crashed to the floor, she leant in and grabbed hold of his bollocks, squeezing with unrestrained anger.

“HOW DARE YOU HIT A WOMAN! YOU CAN’T DO THAT!”

It was Olly’s turn to cry. And cry he did. Sobbing, begging, howling with regret as Tessa crushed his balls in one hand, whilst throwing slaps at the cock cage with the other. Refusing to release her grip, Tessa dragged him up to his feet by the bollocks and pushed him to lean over the desk. This time she met no resistance. Olly sobbed uncontrollably as he leant over, willingly presenting his arse to Tessa. With one hand still reached around to hold her vice-like grip on his crushed testicles, Tessa went about one of her burning fantasies, spanking Olly on his own desk. Snatching hold of a metal ruler, she whacked away mercilessly and with fury as her burning cheek reminded her of the justice of this. Olly was beset with shame and guilt. He cried for his pathetic position, lent over, arse up, getting spanked by the secretary, but a small part of him felt he deserved this. Tessa had looked so upset, so vulnerable when he had hit her, like a little girl. What if she told Sophie? And in turn she told Hilary? Would they would refuse to let his cock out for even longer? With each stinging slap of the cold metal he resigned himself to her mercy. He didn’t try to hold back his crying as Tessa spanked his arse red raw.

Panting heavily, Tessa could continue no longer and dropped the ruler to the floor. As she stroked her own violated cheek, she looked in satisfaction at what she had done to Olly’s. His bright red cheeks pointed up to her in submission as his little chastity device hung unprotected below them. Throwing one final kick into that particular embarrassment she slumped exhausted into the chair. The prostrated boy didn’t dare to move, he was aching in pain and waiting in fear to see how the wronged girl would exact her rightful revenge.

Picking up a pen, she silently offered it to him. Trying to wipe away the tears, he looked down at the paper Tessa had prepared. He’d lose everything. His praise in the recommendation was effusive for her, admitting she completed most of his work to a standard he couldn’t hope to match. It literally begged Marie to employ her in his position, with his salary. The final paragraph made him whimper, as it explained his need for a lesser secretarial role in order to leave him more time for domestic chores, as well as a ‘natural inclination’ to serve under women in the workplace.

“Marie won’t agree to this.”

“-Then you’ll have to convince her.”

Olly racked his brain for a solution, but the throbbing pain of his arse and balls took over. Who was he kidding? He was lying across HER desk with his arse bright red and his cock locked up. He was entirely in this girl’s power. Since his reckoning with Hilary, every girl he had confronted had so effortlessly outsmarted him. As the standoff continued, emerging noise from the stairwell jolted him into action. Maire and Chiara were going to come in! Hurriedly taking the pen his signed his life away, ignoring Tessa entirely, he reached for his trousers and frantically pulled them up. Tessa watched on in shock. It had been a close run thing, but had she actually pulled it off?

Olly just got his zip us as the door opened.

“Morning guys and gals!”

Marie and Chiara were evidently in a good mood. After the usual pleasantries, they retreated to the other side of the office, where they shared the larger portion of the floor-space. Throughout this Olly watched Tessa like a hawk, trying to spot any sign that she was going to give him away. As the two older women went through the partition, he turned to Tessa with caution.

“What happens now?” He dared to ask.

Had she been brought back to reality? He felt safe again in his suit and the commanding presence of Marie, this little intern upstart seemed sullen by the return to normality. But the new found confidence his trousers gave him proved unfounded.

“Oh no you don’t. Come on.”

Tessa hadn’t done all the hard work of subduing this prick to give up now, she wouldn’t let his macho hope of avoiding humiliation get in the way of her career. Taking the papers and Olly in her hands, she marched towards Marie’s desk. Olly just about managed to wrestle her hand of his arm as their boss looked up to them in anticipation.

“Well what is it?”

Handing the papers to Marie, Tessa repeated her carefully prepared words. Marie looked to Olly in puzzlement, the intern’s term had not yet finished, was there really a need to review her now. Putting on her glasses and turning to the statement, Marie read on in incredulity.

“Is this a joke Olly?”

Before he could reply, Tessa subtly stamped his foot hard and began to play with the chain that held the chastity key. Was he really going to do it, to hand his prospects over to Tessa? Marie stared at him with a look of bemusement and just a hint of irritation. He knew full well she didn’t suffer fools. He was secretly scared of her, a woman in charge. Unlike most other women, she was actually taller than him. Long raven hair and elegant looks, Marie always looked the part in bespoke suits. Olly noticed she was wearing a new pair high heels, stripy black and white ones, stirring a little twitch in his cock cage.

“WELL Oliver?” Marie’s raised voice caused Chiara to take an interest, was Olly getting a dressing down?

Marie only ever called him his full name when she was angry. His arse still burning with shame, he bowed his head to his defeat.

“It’s all true.”

What was Marie to think? Her bright young thing admitting he was no longer up to the job? Her little marketing company was barely breaking even, she had had such high hopes for him. Looking up at this sullen disappointment, a rare flash of anger overcame her.

“Oliver you’ve put me in a terrible position. You know we needed you if we have a hope of meeting our current commitments.”

Three sets of female eyes were fixed upon him. He couldn’t believe he now had to argue himself out of his position. Why was Tessa making him do this!?

“PLEASE!” He exclaimed, forcibly abandoning all hope. “Please you have to give the job to Tessa! She’s done all the work, she knows the clients better than me.”

Marie and Chiara studied the pleading boy with astonishment as he actually fell to his knees!

The boss tittered at him in disgust. She didn’t know what had got to him but he really was finished if this was his attitude, actually on his knees begging? Absolutely pathetic. Maybe a secretary’s position really would suit him better. Tessa risked a slight smirk at the scene. It couldn’t be going any better! Olly had played his little part well, now for her to complete a well-deserved victory. Pushing the kneeling boy aside she took a step forward to address Marie.

“I’ve been working on the projections and I think I’ve found some savings we can make from Olly’s original proposals. I’ve also drafted an update on all our current accounts. I can bring them to you if it would help?”

The next ten minutes were something of a daze for Olly. He remained at the side of the boss’s desk, still on his knees, as Marie went through Tessa’s new responsibilities. After instructing Chiara to adjust the payslips, Olly suppressed a tear when hearing what little he, the secretary, would now be making. In contrast, Tessa gushed at her new found wealth, Olly certainly had been making a lot! She would enjoy her hard-earned promotion. Thanking Marie one last time, and offering a delightful smirk of derision to the beaten Olly, she went to her newly claimed desk in triumph. She had taken on her misogynist, macho, boss and bent him into submission. And if he felt her pleasure over his fall from power was over, he was very much mistaken.

After being dismissed from Marie’s presence with a severe scolding, Olly went about his new duties. The girls made good use of their obedient male secretary. Making coffee, filing, taking calls, even picking up Marie’s dry cleaning, As the end of the day approached, Olly detected the two older women were beginning to enjoy bossing him about. But Tessa reserved the most hold over him. He trembled each time she called him over. So far she had restricted her demands to petty menial tasks but this time she had a mischievous glint in her eye.

“Take your suit jacket off. From here on in you will work in a short sleeved shirt, no tie please. A mere secretary has no need of such power dressing.”

Olly felt he was removing his last scrap of dignity as he complied with Tessa’s commands. As she watched her obedient male secretary remove his jacket, Tessa paused to consider how to break Olly’s sudden lack of income to Sophie. Tessa was well aware Sophie had already quit her job in preparation of living off Olly’s back and savings. Obviously she didn’t want to interfere with Sophie’s possession of the boy, but she also needed to assert herself in the office. If these two needs clashed? Well why should she worry? This was Olly’s fault really, after all he had begged Marie to demote him. Tessa resolved to make sure he’d get the punishment.

“I think you’re done for the day. I know Sophie has some exciting plans waiting for you at home. Don’t worry Mr little dick, I’ll call ahead and let her know how you made such an exhibition of yourself begging to be demoted. Have a great weekend!”

 

To be continued…