Brought Down to Serve Pt. 04

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....