The Big Stretch

Jacie was late for her first day at work.

She was flustered as she pushed open the revolving glass doors to the high rise downtown. The guards hassled her for her ID as she dug through her expensive shoulder bag, unable to find it. She had to explain that she was new. By the time she rode the elevator to the 54th floor, she was already sweating in her new blouse and new work suit. The receptionist at the desk gave her a smile as Jacie tried to fake one as she walked up.

"It's my first day, I'm supposed to report to the marketing department for my internship," she says. The receptionist regarded her slim figure and took her time looking up her information in the system. Jacie looked around and scanned her new work environment.

"Honey," said the haughty receptionist, "You're already late for the start meeting. It's around the corner down that way," she said pointing indistinctly.

"What room?" asked Jacie. But the receptionist held up a finger as she answered the phone. Instead of waiting Jacie took off down the hall at a brisk pace. She winced with every step in the new high heels. The new pantyhose's didn't help the blisters now forming.

She rounded the corner of the cubicles and found her way to a hall with a set of doors that looked like conference rooms. She tried the first, only to open the door too quickly. It slammed into a tall man in a suit, hitting his laptop and crashing it to the floor.

"Oh my god I'm so sorry!" said Jacie. In her attempt to pick up the computer, she dumped the contents of her entire shoulder bag onto the floor. The embarrassment flushed her checks as sweat started to build on her forehead. By the time she looked up with the tall man's suit she stopped.

The man was tall with hints of gray in his neatly trimmed beard. His suit was simple but pristine. His dark eyes looked into her, and he smiled. The kind of smile that a superior would give to someone new like her. Jacie felt so embarrassed that she was sure the man would fire her right then and there.

"You must be lost," he said as he picked up a notebook from her bag to give to her. Jacie, flustered, attempted a response.

"I'm so sorry. Yes, I am a little. I'm an intern and it's my first day. I'm looking for the orientation, I...," she said, stopping in her tracks.

"What department?" he asked.

But Jacie started to sweat even more. He still held the notebook. More accurately, her sketchbook. As a beginner graphic designer, she had originally wanted to get into fashion and make clothes digitally. Lingerie and kinky clothing was her favorite, and she constantly sketched out her favorite types in between sketching logos and designs for her internship. But soon the notebook evolved into more erotic fantasy as the lonely nights of studying stretched on into college. The most recent and most graphic ones were most recently done at the back. The way the executive held it, she could see the naughtiest images of them all sticking out. She lifted her eyes and met his sharp ones.

"I uh... Marketing. I'm a marketing intern," she said.

"Oh, you must be part of the new graphic designers that are starting, is that correct?"

"Yes. I mean, yes sir," she said. The executive cocked his head back in a smiling laugh. She found it cute.

"You don't have to call me sir. Call me Phil," he said, extending his other hand to shake hers. It was a firm handshake and she felt the power in his hands.

"I'm Jacie," she said.

"Well Jacie, why don't we get you where you need to be. Here's your..." he said, but Jacie's stomach dropped as he was about to extend the notebook and saw the most recent pages.

Shit she said in her head. Before she could explain, Phil opened the notebook to the back of the most recent images. He looked at them with a blank expression. Jacie's head started to rush, knowing that her internship was over before it even began. She stared in horror as Phil started to page through, taking his time to look over her work. No words of protest could come out of her mouth due to the embarrassment building in her.

Phil paged through a few silently, taking several long moments to look at each image. At one he stopped, his eyes went slightly wide as he froze, studying it. He snapped his head up, looking at her, which made Jacie jump. Then he reached into his coat pocket with the other hand.

"Well Jacie, let me write down the room number for you for where you need to be so you don't forget," he said. A blue pen whipped over the corner of one of the pages. He shut it, then handed it to her.

"If they ask, tell them I held you up," he said smiling. Jacie nodded as she took the notebook and stuffed the rest of her belongings in the bag.

"Thank you," she said. She hustled out of the room, thanking her lucky stars that she wasn't going to be let go on the spot. T

he embarrassment of letting a hot executive accidently see her kinks on the first day of work made her so flustered, she kept wandering without looking at the notebook. But after a moment, she took out the book and paged to where he wrote down the room number.

But not only was the room number written down, but also the name of a bar and a time for that evening. And it happened to be on the page with one of her most desired kinks. A model wearing fishnet lingerie and a harness, being drilled by a large cock right in her ass. She liked this one the most because of the slight wince of pain she was able to capture on the model's face. What's worse is that the man she drew looked like Phil.

Her head started to race. Why did he stop on this one? Why does he want to meet me? What should I do? What does this mean? Suddenly being late didn't matter. The stress started to go away and suddenly just the beginnings of hormones and horniness started to take its place. Her mind kicked over to the positive. The type of older man you fantasize about saw this and wants to meet you. The fear started to make her horny. She looked at his handwriting one more time and it gave her the thrill. Maybe, she thought, maybe this might actually happen instead of just being in my drawings.

She closed her notebook, then took her time walking to the conference room for orientation.

#

Jacie saw Phil sitting at the high bar of a five star restaurant just outside of the office building. Two martini drinks were being made by the bartender when she walked in. Phil gave her a smile just as the bartender served the drinks.

"Hope you don't mind me ordering for you. Seemed like you needed it after such a stressful morning," he said. Jacie took the drink and took a longer pull than she intended and sat at the bar. She had to control herself from looking at his undone tie too much. It was entirely too sexy while the sun was still up.

"Listen," she began, "I've been trying to come up with what to say to you all day. And the only thing I can come up with is to ask you... Why?" she asked.

"Why what?" he teased back. He smirked, holding the martini glass in his fingers by the edges.

"Why... Why did you ask me to meet you after seeing," she nodded to her bag that she put underneath the rail, "that? Are you going to fire me or something?"

"No, in fact I couldn't even if I tried," Phil said, taking a drink. "I asked you here after seeing," he playfully motioned to the bag just like Jacie did, "that, because I wanted to know why you draw things like that."

Jacie felt herself starting to get wet without knowing why, but the thoughts in her head started to flash by as if her life was at stake. There was something incredibly inappropriate with sharing this information with a stranger, much more an older superior at her new work place. But that was partially why. Being rough with an older man in bed, someone who would take control and use her like a fuck toy was such a fantasy that she could barely describe it in words. So she described it by drawing it instead. Further, her ass was always more sensitive than the rest of her body, but she didn't have the nerve to touch herself in that way. She wanted someone older, more knowledgeable, and strong, to stretch it for her. This wasn't something she expected to happen anytime soon. And now, here was this perfect stranger asking the right question. She took another long sip of her drink and set it down.

"I guess there's no point in beating around the bush, is there?" she asked back.

"I'm a really straight forward person, so you can dive right in," he said. Jacie took a deep breath.

"I draw what I want to experience," she said. She grabbed the drink again and finished it.

"And have you?" asked Phil.

"No, not yet. But..." Jacie started to lose her nerve. But Phil leaned forward slightly. She could smell his cologne, which mixed with her senses and the vodka now brewing in her stomach.

"Would you like to?" he asked.

"Yes sir," she said back. Phil smiled.

What transpired over the next hour in a corner booth of the restaurant was the kind of sexy and transparent conversation that Jaice never had with someone her own age. Only a man with this kind of experience, this kind of wisdom, could have. They discussed particulars in blunt terms. She outlined what she wanted. He asked thought provoking questions. And by the time the conversation ended, Jacie was trailing her toes around the outside of his ankles, biting her lip and giggling with the prospects of the coming evening.

#

Jacie felt better in the black high heels she wore that evening. Her toes felt comfortable in fishnet stockings, which she could feel up and around her hidden lingerie as she walked up the driveway of the outskirt villa. The black overcoat she wore hugged her, helping to contain her nervousness and excitement. The harness she wore was exactly the same one that she drew, and her pussy was already exposed and pulsing in anticipation. She recalls what Phil told her at the table.

'Remember, you're going to be my fucktoy for the night' he said to her. And I want you to make sure you're ready for me to play with your ass. It'll be like nothing you'd expect.

She felt her ass tighten as there were footsteps toward the grand white door. The lock turned, and her adrenaline began to dump. Phil opened the door, still in a pristine suit, and smiled at her. He showed her in.

Jacie's heels clicked on the marble floor of the entryway as he closed the door. Dim lighting from the chandeliers overhead made the mid century modern decor soft and welcoming. She turned, smiling nervously at him. But with a serious face, he pointed toward the living room to the right. Jacie walked, with Phil following behind.

The living room was ornate with a high ceiling. In the middle of the room was a large ottoman covered with a red cloth. On it were set out several little steel toys that glinted in the light. Excitedly, Jacie walked over and inspected them. Several plugs and wands of different gauges embedded with glistening jewels were meticulously lined up. She kept in an excited squeal.

"Do you approve?" asked Jacie as he took off his jacket.

"I do," she said back.

"You mean, 'I do, Sir,'" he said back sternly. The tone made Jacie snap to attention and her pussy to start becoming wet. She turned to see him holding a collar and chain in his hand.

"Say it," he commanded, swinging the collar by the chain in front of her.

"Yes sir," she moaned out.

"I'm putting this on you. Thank me," he said as he put the collar around her neck.

"Thank you sir," she said. His fingers touched her neck and her body shocked itself with goosebumps all over her. He clipped the chain to her collar, then pulled it. She tripped forward into him, in which he caught her by the chin. He angled her up, then began to make out with her. His sweet sensual kiss filled Jacie with desire. She began to reach her hands out to embrace him. When she did, she only caught a fleeting feeling of his muscles underneath before he pushed her back by the chin.

"No. I didn't say you could do that, did I?" he said, staring into her eyes.

"No sir," she whined. "I--" she started, but a firm and short slap came across her face that made her vision spark. The impact sent pleasure right down her entire body.

"You'll speak when I tell you to. Until then, you say yes, no, or thank you. That's all you get to say. Is that clear my little fuck toy?"

"Yes sir," she whined out. She put her hands to her side.

With one hand on the chain, Phil used his other to undo her overcoat. He pulled it over her shoulders and let it drop to the floor. He stepped back and inspected her body, marveling at her slender figure and how the straps of the black harness curved around her body. He licked his lips seeing her pussy, already wet and dripping down her leg.

Jacie felt herself becoming eager to please Phil. She thought about all of the toys on the ottoman and then turned to look at them. She had a few moments to see the steel anal plug with a red ruby. She gasped, but not before Phil yanked her by the chain close to him. He grabbed her by the chin again.

"Something distracting you?" he asked her.

"I--," she began, but another firm slap across her face made her yelp with desire.

"You're being a bad girl, and I'm going to make you earn what's on that couch first. Do you understand me?" he asked, his tone firm and commanding. He brought her chin up so that Jacie was on her very tiptoes.

"Yes sir!" she said in desperation. Phil leaned in and put his lips by her ear and whispered.

'You're much fuck toy for the evening. And now it's time for me to use you how I want.

At this, she saw the look in Jacies eyes. He grabbed her by the hair and forced her mouth on his, kissing her deeply and lathering his tongue around her in a way that made her messy. He pressed his body into hers, and she could feel how large his cock was against her body. The thought of how she was going to take that in her ass later made her weak in the knees. She started to moan while kissing. Phils hands started to explore her body, slapping her ass every once in a while to make her yelp.

After a makeout session, he held her by the hair and led her over to the ottoman.

"Kneel over with your torso on the ottoman," he said. She got into position.

"Now put your ass out and make it look pretty for your sir," he commanded.

"Yes sir," said Jacie.

She turned her head to the right to see all of the toys set out. She watched in delight as he took one of the smaller of the stainless steel plugs, then stood behind her. Then she felt a strong hand on her back, pushing her down into the ottoman.

'You're going to take this, and I'm going to work your ass out and stretch it to take my massive cock. Do you understand?" he said.

"Yes sir," she responded.

And then the play and pleasure began.

First she felt spanking over the lingerie. She began to yelp in pain and pleasure. She felt her cheeks getting red and her pussy starting to soak. She arched her back more to put her ass in the air for him to make it easier. He spanked again.

"That's a good girl," he said. Jacie bit the red cloth in front of her in pleasure. Then, she felt a whiff of air followed by spit that hit her right on her ass hole. Her eyes rolled into the back of her head while Phile explored the outside of her ass with his fingers first. She started to moan, wanting more of him.

Soon she felt him get down on his knees. Another spit again, making her jump. But then the ecstasy of his tongue started to play with the outside of her ass. She moaned into the ottoman, unable to control her screams of pleasure. She wanted him to force the plug in, make her feel it and make her stretch out. She was ready for it.

He spanked her again, making her jump and clench in pain. And that is when she started to feel the cold plug make its way into her. He was gentle at first, and she could feel herself stretching, the pleasure shooting its way through her body like small shocks. She wanted it. She ached for more. Then there was the stretch, the slight pain mixed with pleasure, as he forced it into her. She felt it settle and let out a moan of relief and pleasure.

Phil walked around the ottoman and made her lift her head. He looked her in the eyes.

"Does my little fuck toy like that?" he asked.

"Yes sir," she moaned. He dropped her head onto the ottoman. She looked as he picked up a set of rope. She felt her hands behind her as he wrapped the rope in intricate ways. As he pulled it through, the ends of the rope hit her in different places, making small little welts on her ass and back as he worked. Soon, her arms were completely immobilized. He spread her legs. She now felt completely vulnerable and open, ready to be used for his pleasure.

Then she watched as he took the next gauge of plug. A wider one with a blue gem on the top. He also took a bar gag with him. He came around to her front, and lifted her head again.

"Is my little fuck toy going to enjoy moaning while I stretch your ass?" he asked. Jacie could barely respond, still feeling the current plug inside. She felt a want in a way she'd never felt before, just as he told her over the table. Pleasing him, making him proud of her to take it all in her ass, was all that she wanted.

He put the gag on her and she bit down. He tied it tight around her head so she couldn't shake it off. Saliva immediately started to drool out from it, making a mess. Oh I'll be punished for that for sure... YES she thought. But as she thought this, he started to pull out the plug. That same body sensation took her as the pleasure sent shocks through her body. She moaned against the gag, just as the widest part came out.

For a moment she relaxed, but not for long. Phil began teasing her ass again with his tongue, then ran his fingers over her dripping clit. The pleasure of both made her move her hips in delight. She felt ready for more.

The next plug went in and she felt how much larger it was. She gripped her hands together, moaning in both pleasure and pain. Phil took his time, making it go out, and then a little further. He continued this, until she could feel the plug get to its widest point, making her feel wide and open. She tried to moan loudly, but the gag muffled her. Then, as she shook with the pleasure and pain of being stretched, he let it go all the way in.

Jacie felt herself getting close to orgasm, breathing hard and feeling herself filled up. That's when Phil came around and got a large dildo. He walked back, then slid it into her pussy. Jacie arched her back at how easily it slid inside her, filling her up all the way. She felt full in a way she hadn't before, both objects practically touching each other and fighting for room. She tried to ask to cum, but only mumbled.

Phil grabbed her by the collar and made her arch back.

"Don't you dare cum yet. You will cum when I say, do you understand?" he said.

She nodded, then he let her back down on the ottoman. He began to tease the plug out as he slid the dildo into her pussy.

The trade between sensations sent her body temperature into a high heat. The back and forth pleasure edged her close, but she tried to stop it. She bit down on the ball gag and rode the pleasure line between orgasm and holding it.

Just when she couldn't do it anymore, he pulled both of them out, taking time with the plug to really make her feel it. Jacie felt herself breathing hard and wanting to cum more.

Phil came around again, and her eyes went wide when he lifted the final toy. It was a long glass plug, thin at the front and very wide at the end. So wide that she almost couldn't believe that she might be able to take it. But, as Phil came around behind her, she felt him press it into her ass.

She arched her back as electricity from pleasure in her ass exploded up her body. The deeper he pushed, the more her body felt electrified. She wanted to beg him to touch her clit, wanted desperately to cum, but she held on, obeying and being a good fuck toy for Phil. She felt her ass expand wider, and wider, and to the point that she was certain that he had inserted the entire toy in her.