It had been another good day at the office. It was not an uncommon experience for him to find himself on stage, presenting to a standing-room-only auditorium of people, all intent on hearing the message he had to deliver. He was e****ted from the stage after his hour long presentation and mobbed by audience members who all wanted more.
More of him.
More of his knowledge.
His wit and humor.
It felt great to have the undeniable approval and accolades from this room full of strangers that he'd most likely never see again, but would remain locked in his memory as a group that escalated him to new heights in his professional career. It could not be denied, this was one of the best performances of his career to date and he was excited about the press that would come of it and knew his controversial speech would cause waves in the social media arenas and that he'd be responding to inquiries for weeks to come.
However, there was really only one approval he was intent and keen on getting that day, and he was nervous as to what the response would be.
As he made his way through the crowd, smiling nervously and nodding his head politely and making small talk with the lingering audience members, he searched the room for her. He caught sight of her as the crowd began to disperse and found her standing at the back of the room. Dressed in her conservative black skirt suit, she gave no secrets away as to who she was or what she was there for. Anyone coming across her would have thought she was there for the same business reasons they were - to hear him speak. There would be no knowledge of how intimately she knew him and what she knew of his brilliance - The crowd would just dismiss her as being another fan in the "Amazing Simon Club” waiting patiently to speak to him.
She made direct eye contact with him and gave him a slight grin. There was a twinkle in her eyes, but her expression gave nothing away. He couldn't tell if she was pleased or if she was hiding her disapproval and disappointment behind the tight grin. He knew her facial expressions well and her smiles of joy could not be mistaken. When she was over joyed, she'd laugh and smile with her whole body - throwing her head back, smiling widely with an open mouth, showing the world all her pearly white teeth. He so far only managed to get a deep look and a slight grin and that made him terribly nervous.
She stepped forward to join him on exiting the auditorium and walked beside him. He became increasingly anxious as she did not utter a single word to him. She just walked silently beside him and would stop and smile politely as he was still being stopped and questioned by lingering audience members. He was concerned about her annoyance with these strangers who were demanding his time and he began to feel a cold sweat pouring over him. They were finally able to make their way out of the massive auditorium and she finally spoke to him.
"To the room. Now." was all she said. Four precise words and no emotion on her face. She continued walking and he stayed in step walking by her side, listening to the click-clack of her stilettos on the paved walkway to the elevator bays that led to the hotel guest rooms on the other side of the conference hall.
The silence in the elevator was deafening. As they stood side by side, he stated aloud casually as if addressing the elevator doors, "I think that went phenomenally well," and anticipated that she would at least give him some verbal clue that she was pleased with his performance. He searched her face for acknowledgement of his statement, but she refused to make eye contact with him and stared straight forward into the back of the elevator door. He turned to see her reflection in the doors and saw she still had the twinkle in her eyes and the tight grin on her lips.
They made their way to their rooms. As was standard with them, there were always two hotel rooms that were booked and they were always magically connected on the inside. Giving no secrets away to prying outsiders who knew nothing of their extensive relationship. He would enter through his door and she would enter through hers and they would meet always somewhere in the middle. It was their safety zone and he was happy to be now in their world, where she could finally tell him what she thought of his performance.
She stepped forward and looked deeply into his face and finally gave him one of her wide toothy smiles. She immediately pulled his face down to hers and kissed him deeply on the lips - prying his lips apart with her tongue, so she could flick his tongue and entangle herself deeply in his mouth. The relief he felt was exhilarating as her approval was of the utmost importance.
As she pulled away from him, he realized her facial expression had changed dramatically and the panic and realization that he might have upset her came rushing right back.
She stepped back and sat at the edge of the bed, leaving him standing before her.
"Strip for me. Now”
It was amazing to him how quickly the tables could be turned. As just a few minutes ago he was at the top of his game, commanding the attention and adoration of a room full of people to now find himself standing before an audience of one, and just with a simple look could make him feel so very ashamed.
He replied, "Yes, Mistress." and began with kicking his shoes off and pulling off his socks, revealing the secret of the white sheer stockings he had on. His jacket was the next to come off and he carefully placed it on the chair next to him. He knew better than to casually toss it aside or on the ground as he knew how much she loved his suits and was quick to punish him for not taking care of his things.
She nodded in approval. As he loosened his tie and began to unbutton his shirt, she also began to move about the room, still keeping watch on him as he continued his private performance for her. As he unbuttoned his dress shirt and revealed the tight white basque she had dressed him in earlier that morning, his cheeks became flush with the thought of the embarrassment that would have come to him had he not had his jacket on while on stage. What if the audience had seen him tightly bound in a basque underneath his shirt? It would have been humiliating. But yet here he was, standing before her and exposing the secret they both knew was under his power suit.
As he wrestled with his embarrassment, he noticed the change in her wardrobe as well. She had shed her black jacket and in stark contrast to his, wore a patterned black basque as the under layer of her suit and pulled her hair tightly back into a bun, pulling her dark, black hair up to expose the full length of her neck and shoulders. He wanted to approach her and kiss the length of her neck and run his tongue down the sweet valley of her cleavage, but held back as he knew he could not do so without her permission and he was still unsure as to whether or not she was happy with how the day had gone or if she was going to punish him for any shortcomings.
He continued by unbuckling his trousers and dropping them to the ground to expose the white lace g-string she also put him in early in the morning. He gathered his clothes and laid them nicely beside him on the chair and stood straight before her. Crossing his arms across his chest in embarrassment as to what she made him wear underneath his clothes. There he was, white, corset wrapped tightly around him, his lacy white g-sting and his white stockings.
She stepped forward and quickly placed his obedience collar around his neck. It was covered in a furry leopard pattern and had a long black leash attached and he was humiliated that she would choose an a****l pattern for him. He remained still and held his arms down by his side as he knew she was not done with the additions and changes she would make as he stood before her.
As she verified his collar was properly in place, she ran her finger tips down his right arm, producing a line of goose bumps to appear as she lightly scratched him down the length of his arm. She kissed the tip of his nose and he knew to bend his head forward so she would be able to reach him and quickly apply the raven dark, long locks of his sissy girl wig on his head. She would always kiss his forehead to let him know she was done with that task and he could stand upright again.
Next came the make-up, why she felt this was necessary was beyond his comprehension, but he knew better than to question it. She would always apply his lipstick first - a deep shocking shade of red that was in perfect contrast to his pale white skin. She was feeling dark and aggressive and the contrast of the make up she applied to him showed how she was feeling. With a smokey grey eyeshadow, heavy black eyeliner and a deep rouge to his cheeks - his transformation to her sissy whore was almost complete.
She went to the closet to gather the remaining pieces to complete her masterpiece and nodded to him and he knew to put his arms up so she could pull the white flowing dress over his head and it was very rare for her to ever bend before him, but she would to offer him the sling back stilettos she wanted him to step into. And there he stood in full sissy dress, the humiliating transformation complete from being one of the most powerful men in the industry to now being her Sissy whore whom she lovingly called Sissy Simone.
He now stood so tall before her in the stilettos, that when she stood on the bed before him, she was eye level with him. She tugged on his leash, pulling his neck and his body forward to her and purred into his ear, "I'm so very proud of you my Sissy Boy. Your mistress is going to take good care of you and reward you for a job well done."
His reply was, "thank you, Mistress"
With that, she hopped down from the bed and positioned herself on the chaise lounge in front of the big bay windows overlooking the Las Vegas strip, dragging him steps behind her as she led him by his leash. As she sat and pulled up her black pencil skirt up above her knees, he caught a glimpse of her cock. He had no idea she had worn her harness and her massive black cock through the course of the day underneath her skirt and he was immediately hot for her and began to ache to feel her cock inside him.
She reached up underneath his dress, stroking his muscular, stocking encased legs with her finger tips and went directly to the bulge of his cock in the g-string and released him from the cock cage she had f***ed him to put on in the morning with the other items beneath his suit.
"Had you performed poorly today, I would not be releasing you from your cock cage. But seeing how much you have pleased me with your public performance today, I am going to give you the privilege to get hard for me and not keep your cock caged."
to which he replied, "thank you, Mistress"
"now then, come lay across my lap so you can get your spankings" He did as he was told and she once again lifted his skirt, exposing his bare ass and the g-string. She slapped his ass hard with her bare hand, immediately making the spot she spanked turn a brilliant red.
"Oh, Miss! Please be gentle." he cried out.
"Hush, Darling. This is just the beginning."
She continued to spank him hard with her bare hand, and between the lashings, she would bend forward and nibble at his ass with her teeth and lick his round ass cheeks with her tongue.
"Bend your ass up - offer me my cunt."
"yes, Mistress." and he did as he was told, rising up on his knees, pulling back on his haunches, arching his back and offering his ass up to her so she would have no issues licking his cunt. She spread his cheeks wide and moved the g-string to the side and slowly licked the length of his ass and lingered as she rimmed and licked his cunt. She f***ed her tongue into him, tasting and devouring him. It felt so good and he moaned in delight at having his Mistress bury her face in his cunt, lapping at him and rimming his tight ass.
As he moaned, she pulled on his leash and tugged his at his neck - a quick reminder that she had not yet allowed him to express his desire or his pleasure vocally. He had to get himself in check.
"Go and lie down on the bed now, darling."
"Yes, mistress" and he did as he was told. Laying down with his raven locks falling around his shoulders, the white dress spread across the bed, his legs shoulders width apart.
His mistress stood before him and removed her black pencil skirt to reveal the length of her massive black cock hidden beneath her clothing. She approached the bed while stroking the length of her cock and Sissy Simone replied in kind by getting harder and dripping with percum for his Mistress' cock. She straddled over him and kissed him deeply, violently, smearing the deep red lipstick across both their faces. "You are such a slut. Only whores wear this shade of red - as it leaves the best ring marks around hard cocks. You like that don't you?"
"Yes, Mistress. I am a slut and I like to suck cock while wearing red lipstick."
She continued her violent kissing across the nape of his neck, biting at his earlobes, and pulling his head back with her hand - she spread the red lipstick across his neck. And with that she turned and he found himself face to face with her black cock as she offered it to him in a 69 position and as he opened his mouth to take in her black cock, she replied in kind by pushing his g-string aside and taking his swollen cock deep into her mouth.
They stayed in the position for what seemed an eternity - each lapping at each other's massive cocks. Sissy Simone reached up to draw his fingertips through the harness and feel his Mistress' cunt juices flowing from her as he sucked on her cock and she swallowed mouthful after mouthful of his percum as his cock was in the back of her throat.
"Oh Mistress, I want my cock, please" he pleaded.
"You do? You want to feel me buried deep inside you, you little whore?"
"Oh yes, Mistress. Please. I beg you. Give me your cock."
It was his night after all, and this was his reward for an amazing performance. She could not argue with what her Sissy Whore was begging for - she wanted to fuck him good and hard as he had worked so hard for his prize.
She moved over him, lifting the skirt of his dress and slowly slipping the white g-string from him. He watched in anticipation as she rubbed the anal lube up and down the shaft of her cock, obscenely stroking her cock as if she could produce a massive load of cum by stroking it. And slowly moved over him, pulling his knees up about her as she slid between his thighs. She rubbed the head of the cock up and down his ass, to grease his cunt a little further and prepare him to take her and slid the head of the cock into his tight cunt.
He cried out in ecstasy and pain at the shock of her penetrating him. She thrust forward, pushing half the length of the cock into him, forcing him to open up for her and Sissy Simone cried out again - a fine line between the pain and pleasure of it all. Slowly she found a steady rhythm and with each thrust would push the cock a little deeper into him. He reached forward, pulling at her hips for her to go deeper into him and she resisted. Wanting him to only have the cock she offered, this was not his experience to control - it was 100% hers. This was her realm - behind the closed doors - his realm was what remained beyond the hotel doors.
As she slowly thrust into him and he writhed in pleasure before her in the bed, she began to stroke her massive cock, dripping precum all over them both and as she continued to give him more and more of her cock into his ass - the harder his cock became in her hand as she stroked it with each thrust. "Oh please. Please give me all of your cock, Mistress"
and with that final plea, she caved to his desire and thrust herself fully into him, clamping down harder on the cock in her hand and as she thrust as hard as she could into him, he came and sputtered cum all over her hand and his white dress.
His mistress slowly pulled out and lapped the cum from her hand and what she could get from his dress, collapsing beside him on the bed - to stare into his brilliant blue eyes and whisper sweetly to him, "You did a job well done today. I'm proud of you."