The Perfect Date

A Saturday night was reserve for fun and excitement. Some people get invited to parties or a night at a bar. Some plan out overnight trips to an amusement park or go out of town. Hell, some even get wasted at clubs or big sports events, only to pay for decision the following day. And like all of the above, Wes planned for such a night. Only this was a different kind of fun.

The bedroom started to make him uneasy. Dim lights shined down upon the red satin sheets and dark polish wood of the bed posts. Everything looked like it would take a month's pay just to buy it. It was a rich man's secret chamber, a Haven of luxury. And it was complete with velvet rugs, mahogany dressers, and gold lined furniture. One could only wonder what you'd have to do get a room like this for just one night.

"Maybe this wasn't a good idea." Wes muttered to himself. His fingers pattered against the sheets as he sat at the edge of the bed. His legs kicked nervously. This was not like him. All of this was completely not like him. Straight-laced and by the books was his code, no deviations, no guilty pleasure. And now here he was, about to lose his mind by just being at this man's penthouse. Why did he accept his man's invitation again? Why did he think this was good idea?

The red headed male flexed his fingers and took a long deep breath to calm himself. Just relax, he told himself. He came here at his own free will. There's nothing wrong with what he was doing. There's nothing to be ashamed of. The mantra repeated in his head, soothing his anxiety somewhat. But at least he wasn't on the edge.

As minutes crawled by, the door finally opened. Wes's head snapped instantly towards the open and soon a red wave of blush followed closely after. Rich and Handsome wasn't enough to describe the man. Chiseled jaw, short brunette hair, strong athletic build, his body was sculpted to be a paragon of desire. His tux jacket was slung over his shoulder. Black slacks and a half button up dress shirt clothed his body. Loafers were in his other hand along with a red tie. Wes blinked. It was the only thing he could do. The man made him look like a slacker. Even his attire outshined him by the miles. He was right. Maybe this was a bad idea.

The Man greet him with a warm smile, placing his jacket and tie on the other side of the bed. "I'm so glad you could come and join me tonight" He said, walking towards one of the dresser and searching in the jewelry box on top of it. "I was worried that I wasn't going to have a date for the occasion."

"Glad I could help, sir." Wes replied. His voice was so sheepish, soft. Part of him hoped he heard him. Sir seemed more appropriate than referring him to his real name. He stayed seated as the man scoured the box for his gold. The redhead peeked over his shoulder, admiring his form. Of all the people to give an invitation to, why him? He was just so...beautiful. And Wes wasn't even attracted to men. He was straight to his core. Sexuality wasn't a game that he played often even. But there was something about this man that brought a certain side of him out.

"You'll have to forgive me Rebecca." The man continued. "I'm running a tab behind schedule. But I did pick out your dress for you. I'll have my secretaries come and assist on putting it on once we get to the party."

"My name is Wes, sir." It took everything he had to dash away his shyness to speak those words. He stood up to face him, an action not out of resent, but by curiosity. His words halted before he slowly turned his heel to him. Their eyes met and then a sudden jolt of pleasure pricked Wes, sending a shiver of goose bumps across his skin.

"Of course it is." He commented. Deep green eyes, bold as his stature, locked on to the quivering redhead. He stepped forward, closing the gap between them, making his heart flutter from his advance. "But I'm not talking to Wes, am I? I'm talking to my date." His words robbed him of his voice. All he did was stared deep in his eyes, letting dominance press down on him. "Will there be any more questions?"

"No sir."

"Then wait here." he ordered before turning back towards the side door, disappearing within the next room. Wes stood at the foot of the bed. His hands were placed neatly at the small of his back, standing tall like a young girl showing off lovely assets. His sentences echoed in his mind as he waited patiently for him, replaying the message. I'm not talking to Wes, am I? I'm talking to my date. His cock twitched at every single word. The heat of his breath stole his. If only he could stay a little longer. If only he could tell him more of his plans for tonight. Still, a good date can't be naggy. The redhead stayed at his position, quietly waiting for Sir to come back.

Anxiety filled minutes quietly shuffled by before the handsome male came back. The clothing on his back was well put together, Cuff links jeweled his sleeves. His tie was well put together, accompanying his suit jacket and button down shirt. Doing a few last minute adjustments, he walked back to the redhead, watching him low his head and avoid his gaze. But despite staying away, Wes could still feel his presence next to him, causing his cheeks to flush. May I please change into something else? What will be acceptable to you, sir? Deep down, Wes was talkative as he could ever be. But his lips were silent and still. The thought of speaking out now scared him more than anything in the world.

"Aw don't be so shy, Rebecca." he felt his hand reach towards his cheek, raising his head up. Wes almost jumped at how close he was, seeing his smirk. His voice was low when he spoke. "You'll be in your dress soon enough. Just you wait."

"y-yes sir." the redhead replied. The moment lingered, keeping him frozen. But then he let go, heading out the room.

"Come with me." he spoke again, glancing at his watch. "We're already running behind. The Car should be waiting for us." Wes rushed to behind him, keeping at his heel, making sure not to trip or impede him in anyway. He was this man's date. So he needed to act like it. Mentally, he checked his posture behind the man as the two of them venture down the luxurious hallways filled with expensive artwork of all kinds. Their strides sounded off against the smooth shiny linoleum floor. It must be great to be rich. However, it's amazing to be dating the rich.

Down the stair case they went to the main Foyer of his mansion. Wes kept his eyes on Sir as much as possible as he led him to the main door. Holding it open with a latex gloved hand was a beautiful jet black hair female. Wes couldn't help but had his attention taken from him, slowing the stride to gaze upon her form. The frilly skirt to her maid uniform was barely covering her rear. She wore black high heels with fishnet stockings. The outfit she wore barely covered her breasts. The Redhead couldn't help but ogle. It wasn't from an attraction to her but envy. A large ball gag was strapped snugly in her mouth. The red shade of the gag matched the color of her lipstick perfectly. Silently she held the door for the two of them, not making a sound nor making eye contact.

"Who is she?" Wes couldn't help himself. He asked the question before he could stop his voice. He shouldn't have done that. Why did he just had to ask such a stupid question?

But the prestigious male only look back at him as they exited the building, watching her close the door behind her, lock it, follow them. "She will be your assistant." he replied. Wes had to double take a look as she obediently trailed behind. The bulge in his pants grew from her sight. She was helping him? Was it to dress? The embarrassment was starting to suffocate him. Deep down, he was using all his willpower not to explode out with his flustered feelings. Keep calm, Wes. You need to be a good date for Sir. You need to be the perfect, Date.

The black Limo was at best 15 feet from his Mansion, purring at the end of the walkway. Wes and Sir waited once they got the side, letting the assistance walk over to open the door. Both of them crawled inside the vehicle. And Wes saw more maids just like her sitting inside the long passenger cabin of the Limo. Each one was dressed identical to her, only unique from their facial features, skin tone, and hair style. But each one sat at a seat, quieted by a gag, waiting patiently for the two to sit down at the end. As they took their seats, the assistant closed to the door. And soon, the vehicle began to roll on to the driveway, moving out to the road.

All the windows were tinted, acting as blinds against the outside world. Not a single noise was uttered by the redhead as he sat next to the well-dressed man. He might as well have been gagged like the rest of the girls. His voice was locked with in his throat, refusing to come out for anything. Being his close to him was making him uncomfortable. Even his maids were better looking than he was. But still, he kept his eyes low. His hands gripped his slacks nervously, feeling the gazes of his harem look upon him. This was disgraceful. If only he had some kind of curtain or wall from them. Even though, they were silenced, his mind wondered out to grim thoughts. They were commented on him. Wes just knew it.

Suddenly, the redhead's head snapped towards Sir as he Scoffed, looking at his watch. "We going be late." his lips pursed at his sentence. Wes put his head down when he turned to him. "It can't be helped." he then said. "We'll only have to move our plans up a bit early." He snapped his fingers. The Redhead was surprised to see two of the gagged maid moving in unison, crawling towards him. The first one, a short haired blond, reached for a small handbag in a nearby compartment, fetching several items before moving towards him. The other, an ebony beauty, moved towards Sir, kneeling as he began fish something out in his pocket. Wes tried to peek over to see. But a gloved hand stopped him and gently guided him to look forwards.

The blonde maid took off the cap of a stick of lipstick, carefully painting his lips. Shivers of excitement ran up his skin like electricity as he let the silent woman work. Eye shadow and foundation came next. The gagged female worked expertly on Wes's face like a master artist. With each tool that was revealed to the redhead, more joy began to swell inside him. Still, he kept still, letting himself be the perfect canvas for her.

He then felt a tug at his pant. The blonde wasn't done just yet. But he couldn't help but wonder what the second maid was up to. He felt his zipper being undone. Latex hands slipped inside to let his cock jump out free. He didn't budge an inch. But suddenly, the bite of cock metal, almost made him jump, almost making the blonde mess up from his sudden jerk. Sir's hand was placed on his shoulder as before he utter a single word. "Don't worry." he assured. Wes looked down as the second Maid finished her work with a click. A metal chastity device was placed over his member, imprisoning his male hood with a sound of a lock. Nervously, he glanced back at the man. "This is all part of our little date, Rebecca." there it was again. That same name, the name he called him. All the fear began to wash away as he sat back down, letting the first maid finish her painting.

It wasn't long before the two girls finished. And a short while later, the car came to a complete stop. The door opened, allowing everyone to come in single file outside at the foot of a grand brick building. Not a single soul was to be seen. But Wes followed Sir and his women towards the front door, adopting his same demeanor as before. Eye forward, mouth shut, posture straight. Sir snapped his fingers once he got to the door.

"Rebecca." he said "My maids will help you in your dress. Follow them to the dressing room."

"Yes, Sir." he replied, letting him enter the building first before he did. A hive of voices swarmed out from inside. Wes followed the Maids into the narrow corridor. But his curiosity was getting the best of him, peaking over them to see flashes of leather, moans of submission, and images of sadistic weapons at the end. The redhead couldn't get a clear shot. All he could see was Sir leaving his side, heading down the hall, entering the large room at the end. He felt a tug on his arm afterwards. And quickly, he notice it was from one of the maids, trying to guide him to one of the doors to the side.

As the Redhead entered the open door, He quickly found himself inside a jumbo sized dressing room. Florescent lights illuminated the room, revealing the racks full of outfits to fit any occasion. From cute pink princess get ups to two pieces that scream "I'm a slut", the room was a girl's dream. There were even rows upon rows of shoes and heels of every size, stacked neatly on the shelves. Right at the other side of the room was a tall mirror, reflecting his form, his confused, awkward, wavering, rigid souled, male form. Seeing his white polo and jeans made him want to rip them off immediately, shunning away his masculinity. The urge was growing, tempting him. And slowly but surely, it was winning.

One of the girls handed him one of the dresses, a latex corset and mini skirt. Reluctantly, he accepted the pieces of clothing, letting his excitement go wild and rampant. He stripped himself from his polo and ripped off his belt away from his pants, kicking off everything, no longer able to wait any longer. The corset hugged his body perfectly as he slipped in on, letting one of the maid lace up his back. Another one aided him on his skirt, letting him step inside before raising it up to his waist. Black and white ribbon decorated both articles of clothing. Just like the maid, the outfit was revealing, barely exposing his rear, generating a bust for him. Bashfully, he let loose a smile, letting the giddy feeling inside him take over. His own pair of high heels came next. And as he slipped on both shoes, he mentally patted himself on the back for shaving his legs.

Everything they gave him, he happily put on. The blonde wing, the black panties, the thick collar with the word "whore" engraved on it, it was all gladly donned by Wes. Every now and then, he would gaze upon himself at the mirror, seeing his Masculinity being slowly scraped away from his appearance. And every time, femininity would slowly take over, claiming more of his looks, his demeanor, his stance. Before he knew it, he saw himself curtsying and giggling like a little girl. But at the same time, he couldn't believe what he was looking at. The Wes he knew, the Wes that he lived with for so long, it was barely recognizable. All traces of his boring male self have been completely removed. And in its place was a sexy, blonde, latex bombshell, ready to fall to her knees at her partner. Damn, she was hot. The question was, was she enough for Sir?

Someone clapped their hands, causing her head towards the door. One of the maids bowed her head and gestured towards the open door way. These girls must have spent a lot of time gagged, able to communicate without the need to speak. Nether the less, Wes did she asked, walking out towards the main room, finally able to see what was inside.

Masters, Mistresses, and Slave of all kinds populated the well decorative den of sin. Sex was everywhere. On the walls, the floor, the furniture, Sex and submission was the main theme of it all. All around her she could see it. A mistress was sitting at the leather couch, letting her pet clean and massage her bare feet with his tongue. Another Master was at the table, attending to his bound toy, letting the candle in his hand drip upon her exposed flesh. More displays were all about in the wide open room. All of them excited her. Her cock rattled and banged against the bars of its cage. The sounds whip cracking and ecstasy filled screams made her want to jump for joy. But her shyness anchored her in one spot, scanning the area for Sir. As lovely was the action in the room was, she needed to be at her Sir's side. She needed his approval.

"My, my, my." his voice chimed in her ear. Rebecca spun around and noticed him approaching. The smile on his face beamed at her, causing her to blush as he approached. The now-blonde woman quickly stood up tall, stuffing her sheepishness to the side, keeping herself at attention for her Sir. He stopped in front of her, looking down at her with satisfaction. "You look stunning, Rebecca." he said. "I knew that outfit would be just perfect for you."

"Thank you, Sir." she spoke, hiding her own from him. A sudden warmth began to build with in her, relishing in the feeling of her Sir's approval. "I'm glad you like it."

His hand suddenly grabbed her by the arm, spinning her around, pulling her close. Rebecca's heart skipped a beat. The scent of Sir's cologne filled her with lust. The need to serve, the need to bend to his will drew her closer to him. "I don't just like it." he whispered into her ear. His lips lowered to her neck, coaxing her to give me more of what he wanted. "I love it." his voice lashed out with pure dominance, enticing her even further. Her knees felt weak. She grinded against him, no long resisting his voice. I want you. I want your cock, sir.

Leather cuffs were revealed to her by one of Sir's maids. Eagerly, he took them, strapping each cuff to her wrists, binding her arms. She grabbed her by her golden blonde locks, taking a whiff of her scent, lick her neck. "Use me as you see fit Sir." she moaned, her lip quivering. "I'm yours."

"I'm your what, Rebecca?"

"I'm...I'm..." her voice stuttered. The words were there. But they were weighted down with coyishness. And it took everything she had to make them jump out. "I'm your date, Sir." with that, her invitation was given. Sir grabbed her arms and brought her to the middle of the room where a lone chained hook dangled from the ceiling. He took the chain link from her cuffs and pulled her arms up, hooking them in the air and forcing her to bend down, raising her nice round plump ass in the process. Sir chuckled, only bringing embarrassment to her. All around her, she could sense them. She could feel their presence. She could feel them grope them with their eyes, watching as Sir circled around in front of her. With a gentle hand, he guided her face up to his.

"I'm going to fuck you." he stated boldly. "I'm going to have all these people watch me fuck my sexy date."

Rebecca was about to protest. But she was interrupted by a large red ball gag being shoved inside her mouth. Sir buckled it swiftly, muffling her protests. A part of her wanted to run away. The fact of being fucked in her tight pussy was unbearable. But the other side craved it, telling her wiggle her ass in front of her, moan like a cum crazed whore, present herself before sir. I want your dick, sir! Please give it to me!

Slowly, his cock invaded his rear, causing Rebecca to moan like a needy slut. The more he pushed his length inside, the louder she vocalized her desires. Her fingers flexed. She leaned into him as he mounted her ass, thrusting, pounding, fucking her rear.

Harder! Fuck me harder! Beneath her skirt she could feel herself drip from inside her cock cage. Her length was thickening, twitching. She was thankful for Sir using lube. But it didn't stop her from asking for more. Every bit of her rear hole was being stuffed by his rod, rammed relentlessly. His movements became wilder and wilder by the minute. The gag quieted a hiss, hoping he would hear, hoping he would rip him in half with this thick, rock hard, male hood in front of the entire party.

"That's it Rebecca....take it..." all movements were stilled in the room. Everyone was silent. All he could hear was Sir, using her as it were natural to them both. "Take it Rebecca....take i-EEERGH!"

His hot seed injected inside her, feeling it cream her ass. The mere thought of it, made her moan with delight, her body shivering as his grip tightened on her arms. Pulse after pulse, his cock drained into her before he pulled away, letting it drip from the puckering hole. Rebecca was in absolute heaven. The spotlight was on her, showing her naughty, sexy, slutty, body to all with in the room. And she loved it all. Sir took in a deep breath, letting the afterglow of his fun wash over him. "Did you enjoy yourself, Rebecca?"