By MissKateKees

 

Checking his phone for any contact from Sophie or Hilary, he found nothing but a voicemail from his secretary Tessa. She was little more than a jumped-up intern at the office and yet her tone on the phone was thick with sarcasm as she reminded Olly he was meant to be in the city ten minutes ago.

On that train journey in, he struggled with his shirt collar. It was constantly scratching his neck, while his tie seemed tight around his throat. He couldn’t wait to get home and take all this pretence off, to get back to sultry pictures of Sophie. On entering the small office he was angered to see Tessa sitting at his desk. She always overreached herself.

“Get out from there.” He snarled, he really wasn’t in the mood for her attitude today. Tessa looked up at her so-called line-manager. She was barely a year younger than this macho, yet he got to order her about whilst she suffered away on a minimal salary from this useless internship. She had a degree in management, for what? To make Olly coffee? She remained in his seat while she studied her oppressor, was he sweating?

Olly really couldn’t be doing with the insubordination of this girl. She sat there like she owned the place, owned him. He had never really considered her attractive, and therefore she was really only good for making coffee or drafting his reports for him. She had a mousy look to her, small frame and unkempt curly hair, almost boyish. Olly felt nothing but disgust for her. Tessa finally relented, she got up from Olly’s desk and made to leave. As she past him, she felt a hard slap to her arse.

“Coffee, you stupid wench.”

Tessa froze in astonishment. Had he actually just slapped her arse? She turned and threw a look at him, but Olly was already busy with his laptop, chuckling at his little victory. Her thoughts were consumed with loathing for this arrogant prick, he really needed to be brought down a peg or two; perhaps she’d tell Marie the office manager, after all there were three women in the office and just one guy, Olly. He shouldn’t be allowed to strut about like the proud cock.

As he sat at his desk, the hours crawled by. He longed to be home again, to further explore this new sexual revelation of his. He could no longer deny it, something about Sophie had a profound effect on him. She wasn’t girlfriend material by any stretch of the imagination. She was from a poor rural background with absolutely no breeding or affluence, as well as being about five years older. And yet there was something about her. Yesterday’s event felt like a vivid dream, but a dream nonetheless. He was relieved to have come out of it intact, neither of the two ladies had made contact with him, they were probably as embarrassed as he was from the whole ordeal. Sophie would be on the train home this evening, if he flirted with her, perhaps he could cop a feel of those enormous tits, she’d probably let him the desperate slut.

Tessa’s lazy drawl interrupted his thoughts “Call for you. It’s Sophie. You know Sophie right?”

“Put her through now!” Olly failed to hide the panic in his voice, he certainly didn’t want to leave those two girls chatting on the phone. He was well aware they somehow knew each other. Picking up the receiver, Olly wiped his sweating forehead. His tie was choking him so he yanked it off in anger and undid his top buttons.

“Yes…Sophie?”

“Olly! Good to speak to you, just letting you know, don’t look for me on the train tonight, I didn’t go into the city today. But you can come by my place afterwards, Hopefully see you then!”

With that she hung up. What did it mean? She had sounded very friendly, happy even. The prospect of seeing her again arose feelings of lust but also of anxiety. Would she mention what had happened? Had she kept the photos she had taken? But to see her, at her place, it was a perfect chance to make a move. Despite his macho appearance, Olly had shied away from ever sleeping with a girl. His good looks and athletic body had presented him with plenty of opportunities but the prospect of his little secret being exposed had always deterred him. But Sophie now knew of his little affliction and she still seemed eager. Maybe it wasn’t actually that small? Perhaps it pretty average. Sure girls talk of huge dicks but they probably didn’t exist, Olly had never seen one. An infamous lay with Sophie tonight would prepare him for Eleanor next week. He’d go into that date a man, not a boy.

*****

He knocked on the door quietly, his previous confidence for this rendezvous had since deserted him. She had the pictures! What would she do with them if he slept with her then scarpered? Sophie immediately opened the door.

And she looked stunning.

Her hair had been done in a new wavy style and she stood tall in black high heels with a figure hugging dress to match. She bounded forward and gave Olly a fulsome hug. He felt those beauties press against his chest. He in turn pulled her closer into him.

“So glad you could find the time Olly!” She said before giving him an enthusiastic kiss on the cheek. She was always trying to kiss him hello and goodbye, until now Olly had shirked this affection with disdain.

“Not a problem.” Olly stammered, finding himself leaning in to turn kiss her cheek. Sophie’s face lit up with his impromptu display of affection, they spent a brief moment smiling at each other. It was how Sophie always imagined it.

Regaining control Sophie took Olly by the hand and walked him into the flat. “Steph and Kate are at a bar so we’re alone for now. My bedroom’s through here.”

Olly couldn’t believe it was this easy as she led him into her bedroom, he was finally going to fuck a girl! On entering the room Olly’s hopes were reinforced. The lights had been dimmed, an incense candle was burning and classic slow music was playing. He felt his little dick stir with excitement. Sophie pushed him down so he was sitting on the bed, she leant in and kissed him hard on the lips. Olly immediately reciprocated and Sophie was in heaven. It took all her strength to pull out and regain composure.

“I’ve made something for you.” She said as she picked up a large book from her desk. Handing it to Olly she sat onto the bed beside him and put her arms across his broad shoulders. Whispering into his ear she said “It’s a photo album.” Olly couldn’t believe it! Had she taken photos of herself for him?! He hoped to God there were some naked ones of her luscious tits.

“Open it. Take a look.”

As he opened the album and took in the sight of the naked body before him Olly’s faculties began to desert him. He struggled to breath, his head was pounding and his eyes were already watering. On each and every page was a naked picture, and they were all of him. Olly let out an audible cry as he came to the first picture Sophie had taken, with him sitting on the floor, legs apart, tears streaming down his cheeks. And right there front and centre, a pathetic little dick sticking out. It really did look small to Olly, a little stub smaller than the drooping testicles. Sophie leaned in and kissed his ear, “That one is my favourite.”

Fighting back the tears, Olly looked at Sophie with hurt and confusion. “Why have you done this?” He stammered through his heavy breathing.

Sophie’s expression turned from deep abiding love to anger. “I did it for you! You’re so proud of your body I thought it should be celebrated. Every INCH of you.”

“Tell me no one else has seen this?” Olly still felt a flicker of hope, if this was intended for him, he could simply burn it and pretend that morning had ever happened.

“Well…”

“Sophie PLEASE!”

She looked at him with disappointment. He had been so charming earlier, and she had spent all day immortalising his modesty in this album, and this was how he treated her efforts? He was still in it for himself. It seemed Hilary had been right in her prediction – Sophie had harboured hopes that Olly would come to the inevitable need for them to be together independently but clearly Hilary’s proposal was now necessary.

“Hilary has her own photos.” – Olly whelped in terror – “But she’s agreed not to use them for her art exhibitions without my permission.”

Olly couldn’t understand the link, “your permission?”

“Isn’t it obvious my love? I can’t have my boyfriend exposed in front of an entire art gallery without my say so.”

Olly could simply not fathom what the conspiring bitch was talking about.

Recognising the look of utter stupidity on his face Sophie resolved to explain it in a way this dick-thick could understand.

“Look I get it. You’re rightly ashamed of your micro-dick. Hilary said some very nasty things about it and you’re afraid that every girl who sees it will laugh at you and want nothing to do with you.”

With these soul-crunching words Olly felt said cock retreat into itself. He moaned quietly in despair.

“But you don’t have to worry. I still love you, even despite your cute little dicklet. It won’t affect our relationship, well not too much.”

Olly turned to look at Sophie. Her cheeks were flushed as she pulled him closer to her. He looked down at those glorious breast barely an inch away. At that point his phone rang. Both of them jumped, startled as they were jolted back into the real world. It was Eleanor. Seeking an escape from Sophie’s temptress embrace, Olly forcibly shoved her off him and answered the phone.

Sophie was simply astounded by his rudeness. She had tried to make this as romantic as possible for both of them, she wanted to start their relationship on the right foot; everything she had done was to save Olly from deep humiliation. But it seemed Hilary was right all along, there was only one way to force him to submit. It was déjà vu for Sophie as he laughed and joked on the phone to Eleanor, talking about plans for next week, how dare he!

Olly tried to string the conversation out for as long as possible. It felt so good to be him again. Eleanor would help him break free from Sophie’s lustful hold over him. But after ten long minutes Eleanor had to hang up. Suddenly she was off the phone and it was just him and Sophie. Sophie’s face was fixed with rage, she didn’t say anything, but her look of hurt dragged Olly right back to where she had had him. Seeking to end the tension, Olly slowly put his arms around her, pulling her into his embrace. She complied silently. God she felt good to Olly. He slowly moved his hands up from her waist towards her breasts. She didn’t seem to mind. Finally he cupped both with a hand and squeezed gently. Ecstasy! They were bigger than his grasp and so he began to freely grope her chest, squeezing ever harder.

“Stop! What are you doing!” Olly felt her knee smash into his groin. The all too familiar pain winded him as he fell to the foot of Sophie’s bed. He strained to look up at a wrathful Sophie.

“HOW DARE YOU! You plan a date with that bitch, hurting my feelings on purpose!” He spotted tears in her Sophie’s eyes.

Olly realised this charade had now gone far enough, she was clearly unhinged. He needed to cut his losses quickly. “Look I’m sorry Sophie but I am going to date Eleanor and you will just have to accept that.” With those words, Olly realised he had immediately made a mistake, Sophie’s hand came hard and sharp across his face. As Olly laid on the floor, clutching his burning cheek, the photo album was placed before him.

“Steph and Kate will be back soon. What fun it will be for them to discover your little secret.”

How? How had he forgotten about the album? In a moment of lust for Eleanor he had insulted the girl with enough photos to ruin him forever.

Sophie was desperately trying to recall Hilary’s advice, first strip a man of all pretences.

“Get up” Sophie cried as she grabbed his ear and brought him to his feet. “You don’t seem to get it. Is your little dick doing all the thinking for you? I’ve given you so many opportunities to do this!”

“Do what?” Olly mumbled, terrified that he had finally pushed her obsession over the edge.

Taking both his hands in hers Sophie looked him in the eyes.

“To ask me out, to be my boyfriend, we’re going to spend the rest of our lives together.”

Olly couldn’t help himself, he instantly snorted in derision at this ridiculous fantasy. Sophie cocked her head to the side, wild with anger at his insubordination. She raised her hand to slap his grinning face when the front door clicked.

It was Steph and Kate. Olly could tell from their raucous laughing that they were drunk. Unsure what this meant for his current predicament, he looked to Sophie. After a brief pause, she grabbed the album and made for the door. He only just caught her, clutching her hard into his body. She shook furiously trying to get him off her.

“PLEASE Sophie no! Not them! Not anybody! You can’t! PLEASE! They can’t see it!”

“You had your chance Olly!”

“I’ll do it I’ll do it!”

With this Sophie stopped struggling, Olly fell onto floor in defeat. She had been so close to exposing him to the female world. She would stop at nothing to attain him.

Sophie panted with relief as she sat back on the bed, clutching the album to her beating chest. Had he relented? Was he hers? It didn’t feel like it, she had expected it to be more triumphant. Remember what Hilary said.

“Take-Take off your clothes…” She could barely get the words out and Olly looked to her in horror and disbelief.

“We’re going to do this properly. Stand up and remove your clothes for me.”

Olly’s head was pounding, he’d been put through the emotional wringer tonight. But was he actually going to be rewarded with sex? Sophie was panting hard, her breasts were heaving up and down, lust overcame him, he was going to fuck her hard. Sophie was in awe as she witnessed the love of her life willingly rip his shirt off in front of her. She had often fantasied about him doing so, his lithe, naked body serving her as a willing and obedient partner. Stripping solely for her. She was so SO close to achieving him.

Olly’s passion was checked as he grabbed the waistline of his briefs. Glancing at the photo album, his modesty overcame him. Sophie was quick to notice his hesitation but there was no way she was going to allow him to stop now.

“Let me.” she said as she took his arms and brought him towards her on the edge of the bed. Olly stood there silently, legs trembling as Sophie savoured a good long look at her prize. He truly did have the body of a Greek God. She raised her hands to caress his ripped torso, the feeling was electric. As she worked her hands down she took a tight grip on his briefs both sides and paused. They were little tighty whites. She could just about make out a little bulge within them. She couldn’t resist running a hand across the little package, causing Olly to gasp in anticipation.

She pulled them down. One smooth, quick action right down to his ankles. His little secret was eyeline for Sophie, she could feel the heat from it. In a thick garden of hair, a little stub of a thing peaked back at her. Two low and heavy testicles were just about the only sign that Olly was a man at all. This was her moment of triumph. And Sophie felt cheated. She knew full well of Olly’s little problem (she had a hundred photos to prove it) but after all her efforts; was this really all he would be bringing to their relationship? It didn’t look fit to please a woman and Hilary had strongly advised against trying it; “there are other tasks for little Olly.”

Olly looked down at Sophie with trepidation. She seemed so disappointed. Her vision fixed on his ‘manhood.’ Desperately hoping not to lose this moment of passion Olly took her hands and encouraged her to stand up, to break the scornful gaze upon his own inadequacy.

“Now you…” He dared. Sophie rolled her eyes at this demand and sighed – yet Olly found himself victorious! She reached behind her and pulled down the zip of her dress. Olly took a step back to drink in this vision, as the black dress slowly fell to the floor. Sophie stood before him, black lingerie complete with stockings. Her heavy breasts were barely contained in that lacy black bra. He didn’t quite know how, but he had done it! His little cock rose to the occasion, all one and a half inches pointing hopefully up to Sophie, this goddess before him.

This was not lost on her, she burst out laughing at this little fella’s appearance. “A bit presumptuous Olly!”

He didn’t understand, blood was pumping furiously to his dick, not his brain. “Eh?”

Sophie smiled to him “You haven’t actually asked me out yet. And here you are, waving your little thing about! What is a girl to think?!”

Olly thought they were well past formalities at this point but he dutifully stepped forward to kiss Sophie’s neck, he could taste her perfume with each loving kiss.

“Come on Sophie…”

“-not nearly good enough.” Sophie pushed him aside, Hilary had warned her on how his animalistic tendencies would take over; she had to rule him with a firm hand. Olly couldn’t stand this teasing, she was obviously desperate for him, he hugged her again, his cock pressed hard upon the inside of her stocking-clad thighs.

“Down boy!”

He was on the floor yet again. His face stinging from another Sophie slap.

“First you need to apologise to me. And it had BETTER be convincing. Or else!” Sophie stood tall above, looking down at him – high heels were such a wonderful aid! She was now thoroughly enjoying this, just as Hilary had said she would. Below her was the supposedly unattainable Olly, completely starkers, lying helplessly at her feet. Which reminded her – she put one heeled foot forward before his face. Olly groaned as he looked upon her heel. As he tried to get up he felt her other heel bearing down on his back, he slumped to the floor again. Crawling forward, he somehow knew instinctively knew what to do. Her bowed his head as he planted a kiss on Sophie’s heel.

“Again!”

Olly abandoned all caution and threw himself into it, kissing every inch of Sophie’s heel. He didn’t quite know why, but he couldn’t stop himself submitting to this goddess. Sophie watched on in delight. She had always known Olly secretly loved her, he was dying to submit himself to her! “Oh my!” she exclaimed, overwhelmed by his frantic display of submission and obedience.

“-but I still don’t hear an apology.” She sat on the bed before him, her stocking-clad legs crossed as she looked upon him, eyebrows raised in expectation.

Daring to get up onto his knees, Olly was dumbfounded by this goddess. She was so confident, so assured, and doing her bidding felt so damn good. His little dick strained in anticipation, wet with pre-cum.

“I’m so sorry Sophie.”

Sophie’s look of amusement turned sharply to a scowl. Olly was horrified how he had failed his mistress. Throwing himself back to her feet he felt tears of failure in his eyes.

“I’m so sorry mistress! I love you! I love you!”

Sophie threw her head back and smiled in triumph. She had always known it, and here he was, devoting himself completely to her for eternity.

“‘Mistress’, I like that.” Sophie ruffled his hair, bent down and kissed him on the cheek.

“Now get up my little boy.”

Wiping away the tears, Olly felt a heavy weight lifted from him. Of course he loved his mistress, she was his everything. Standing before her, Olly did not dare to attempt anything. That was the prerogative of his mistress. Sophie took her time studying the subservient body before her, she casually flicked the little penis and played with his testicles, tugging them down sharply, daring Olly to complain, but no verbal resistance came.

“Good boy. You can put your underwear back on now.”

The words hit Olly like a hammer. They hadn’t even started! Surely the sex was coming! To consummate their love! His little penis darted up and down in a frenzy.

“But- aren’t we going to have sex?”

Sophie’s benevolent attitude once again turned to anger.

“Sex? With that?” She once more flicked Olly’s pitiful offering with contempt.

“Besides, we’ll go no further in the bedroom department until we’re married. If you’re very good, I might let you go down on me one day. As you don’t have a cock, you will have to service me with your tongue. But for now you need to earn my love. And you’re a long way off from any of that.”

With these crushing words, Sophie reached for her dress and began to change. Olly felt the tears return, he couldn’t quite comprehend what Sophie wanted from him. The glorious vision of Sophie in lingerie was gone, she zipped her dress up and reached for Olly’s tighty whites. Holding them open for him at his ankles, she commanded him

“Step right in.” He whimpered in sadness as he stepped into them, and then howled as Sophie dragged them up to trap his cock in. She surveyed the pitiful scene, Olly quietly sobbed as his unused yet still erect dicklet strained against the tight fabric. Why wouldn’t he just do as he was told? She threw her hand into his package with a vengeance:

“STAY DOWN!”

Olly buckled over and gave way to his sobbing. He really thought he was going to have sex! Would Sophie ever allow him to pleasure her? Maybe if he did whatever she said, then just maybe she would allow him to stick it in?

“Stop crying, you stupid boy. We’re about to tell the girls the good news!”

Before he could comprehend the significance of this, Sophie clasped his arm and dragged him into the bright lights of the living room.

“HI, GIRLS! I believe you already know my boyfriend?!”

With that Sophie pushed her dumbstruck man before Steph and Kate, who were sitting on the couch, mouths wide open.

 

To be continued…