College Proposition

This is a story I wrote at the request of a friend. It is definitely different than what I typically write so I would appreciate your thoughts in the comment section. I certainly hope you all enjoy it. Thanks!

*****

Katie stepped out of her class building and pulled her sweatshirt a little tighter against herself as she was met with the brisk pre-spring air. It was Thursday and her final class had just gotten out. She was tired and would love to go back to her dorm and take a nap but she knew that she had a big test tomorrow she had to study for and the library was her next stop for the day. She sighed thinking about the long night of studying she had ahead of her. Luckily, though, the library was open until midnight on weekdays.

'First things first,' she thought, 'I need some coffee if I'm going to be up all night.'

It was a large college campus and there were multiple coffee shops spread out around the buildings. Her favorite was a small shop tucked in a small walkway between the agricultural building and the biology center. It made great espresso and it was open until nine o'clock which was great for late study nights. It was nearly empty when she entered which was normal for this time of day. There were just a few people sat around the café.

"Large mocha, please." She told the guy behind the counter and stared around absently as she waited for the drink to be ready.

"That'll be 4.50." the guy said as he set the cup on the counter.

"Let me take care of that." Came a deep, smooth voice from behind Katie.

She turned around to see a tall man in a dark gray suit standing behind her. He stepped forward and dropped a twenty on the counter from his wallet.

"Would you mind joining me at my table for a few minutes, miss?" he asked her, before walking to a table where he had been sat over in the corner of the café.

Confused, Katie took her drink and, after a moment of hesitation, followed the man to his table and sat across from him. He looked to be in his thirties. She could see he was handsome. His well-tailored suit fit perfectly to his muscular frame. His hair was short and black and he had a short, cleanly trimmed beard.

"Is there something you want?" she asked, still unsure of why she had been brought over.

"I'm sorry." The man said. "Let me introduce myself. My name is Nicholas Murphy. May I ask your name?

"Katie...Katie Winslow." She replied.

"Well Miss Katie, the reason I asked you over here is because you caught my eye and if you are willing to hear me out, I have a proposition for you."

"Umm...I guess." Katie said, with a little trepidation.

"Well I am a man of certain taste. I haven't quite yet found the woman for me yet but I still have needs as a man. And I prefer to avoid professionals, if you know what I mean. You have caught my eye and I would love for you to join me this weekend for the night."

"Okay I think I'm done here." Katie said, as she realized what the man wanted and got up to leave.

"Wait." The man said calmly.

Katie froze. He wasn't shouting or even speaking loudly but his voice held an authority that made her pause. He motioned for her to sit again and she reluctantly did.

"This is a proposition. A business deal I suppose but I would prefer you didn't think of it that way. If you will join me Saturday evening, I will pay you fifteen thousand dollars, cash." He said.

Katie thought she had heard him wrong at first. Fifteen thousand dollars? There was no way.

"I'm sorry, how much did you say?" She asked.

"Fifteen thousand. I could get an escort or hooker for a few hundred bucks but that's not my taste. I prefer someone like you. You are beautiful and more real than those women." He replied.

She had always known she was a somewhat pretty 22-year-old. She was a tiny girl at just over five foot. She had shoulder length, dirty blonde hair that she usually kept up in a ponytail. Her breasts were only relatively small B cups but they were perfectly shaped and she was okay with them. Her waist was slim and her little bubble butt went perfectly with her frame. Her eyes were big blue, doe eyes that people had complimented her on before.

But to think that someone would offer her so much money just to be with her for one night was crazy. She could really use the money. Her nursing major at this university had come at a steep tuition and she had plenty of student debt. Fifteen grand would go a long way. But she still wasn't sure. She had only had sex twice before. Once was on her prom night and it was an inexperienced and drunk fumbling mess for both of them. The second time was with a boyfriend who only lasted a couple weeks before they broke up. But she knew she needed the money. She closed her eyes and sighed.

"If I say yes, what are the exact terms." She asked.

"It's quite simple really. I will pick you up Saturday around seven o'clock and bring you to my house. You will do whatever I say for the night. Sunday morning, I will hand you fifteen thousand cash and you will be driven wherever you want to go."

The whole 'whatever I say' made Katie kind of nervous but in the end her thoughts of the money won her over.

"Fine. I'll do it" She said. "How will you find me on Saturday?"

"Put your number in my phone." He instructed before handing her a black iPhone.

She put her number in as Katie in his contacts and handed it back to him.

The man stood up and placed the phone in his inner suitcoat pocket.

"Very good, Miss Katie." He said. "I look forward to seeing you this weekend."

With that he left her sitting there in the café and walked off into the fading sunlight.

Katie couldn't hardly believe what just happened. She kept playing the scenario over and over in her mind as she drank her coffee. She was very nervous about this weekend and what the man had in store for her. But she also was equally excited about the money.

'Fifteen thousand dollars!' she thought giddily.

It was only Thursday but her stomach was tumbling and full of butterflies as she thought of Saturday. But even though she was scared of what was to come, she could also feel some anticipation in the bottom of it all. She finished her coffee and tossed the empty cup in the trash can before leaving the shop and heading for the library. She still had a test tomorrow and she had to focus and get to studying.

The next day seemed to drag on forever. Katie could hardly focus during class and her thoughts were drifting all over the place. She managed to focus up enough for her test and she thought she did reasonably well on it but as soon as she handed it in and walked out of the classroom she realized she was that much closer to Saturday and all her nerves returned. To get her mind off tomorrow, Katie decided to go spend some time with her friend Anna.

"Katie!" Anna exclaimed as she opened the door for her friend. "What's up, girl? How ya been?"

"I'm good." Katie replied, and walked into the dorm.

Anna was very much opposite of Katie in many ways. She was a taller girl at 5'9" with long brown hair that fell down her back. Her figure was ridiculously proportioned with huge double Ds, a tiny waist, and wide hips that formed her big butt. She was a very outgoing girl who was always going out with guys and partying. She had an infectious laugh and knew how to make people smile which was why Katie was here tonight. She knew that if anyone could distract her, it was Anna.

They talked for a while about how classes were going and all the work they had lately. Anna was a environmental science major so she understood the workload that Katie was under as well. Anna did most of the talking and Anna listened to her stories and jokes. Eventually they turned on Netflix and surfed through shows for the rest of the night. Around midnight, Katie crashed on the futon in Anna's dorm.

Katie woke up on Anna's futon and sat up groggily. She had a blanket on top of her and realized that Anna must have placed it there last night after she went to sleep. Anna was already gone by the time she awoke. She checked her phone and saw that it was just past noon. Suddenly she remembered her deal that she had made for tonight and that in seven hours, she would be going to have sex with a handsome older man that she barely knew.

She yawned and stretched, working out her stiff neck and shoulders before getting off the futon and heading back to her room. She still had hours before seven so she just pulled out her laptop and continued last night's ritual of watching Netflix shows. Halfway through an episode of The Office, her phone dinged. It was a text from a random number that read, 'seven o'clock. Be at parking lot K'. She knew it had to be from him. 'What should I wear?' she replied. A minute later came a reply. 'Wear something comfortable. I only care what's underneath'.

Katie shivered with nervousness and a bit of anticipation as she read that. She still couldn't believe that she, a small-town girl who was one of twenty thousand students at the university, could command such a high price for one night with her. She un-paused her episode and returned to watching the show.

At six o'clock, Katie reluctantly got up and went to go shower. She cleaned herself well and began getting ready. She did her makeup and did her ritual as though she were going out to a bar or a club. She dressed simply in a pair of skin tight jeans and a t-shirt with a sweatshirt over top to keep off the night air. At ten minutes to seven, she left her dorm and made the short walk over to parking lot K.

She waited anxiously, checking her phone every thirty seconds to see the time. At exactly seven, a black Mercedes sedan pulled up and stopped next to her. The back door opened and Katie nervously got inside. The man was seated beside her in the back. He was dressed in a simple but elegant black suit. Up front, a man in his forties or so sat behind the wheel looking forward.

"Wonderful to see you again, Miss Katie." The man began. "This is my driver, William."

The driver nodded his head at her in the rear-view mirror and resumed looking forward.

"Are you ready to go?" the man asked.

"Yes." Katie replied.

"Then let's go, William"

The driver nodded and pulled away from the curb and left the parking lot.

"So, tell me, Miss Katie," the man began. "What are you majoring in?"

"Nursing." She answered.

"Ah." He nodded. "That's a tough job with long hours. I'm sure you'll do great. Where are you from?"

He continued to ask her questions about herself for the entire ride and listened intently as she answered each time. He had a quiet intensity to him that made her stomach fill with butterflies. His eyes were warm and friendly but also steely and she felt like they could also be very hard and cold when he needed them to be. Before she knew it, she had pulled into a private driveway and up to a roundabout.

The driver got out and opened the door for her. She got out and looked up at the house they had come to. It was a massive two-story building with tall ornate windows and trim. The front of the house was three steps leading up to a large stone patio and a set of huge, oak double doors. She couldn't believe how beautiful it was and suddenly realized that fifteen grand probably wasn't that much to this man. She didn't realize he had come up behind her until he placed his hand on her shoulder, making her jump a bit.

"Right this way." He told her and guided her into the house.

They entered into a massive entrance hall in front of a staircase on the left side of the room curved up to a big balcony which overlooked the entire room. She followed him up the stairs to the second floor. They went down a long hallway past bedroom after bedroom before they reached the biggest door at the end of the hall. Katie followed him into the room which was clearly the master bedroom. It was huge. Probably four times the size of her dorm room. In the center of the room against the far wall to her right was a massive king size bed. A dresser and wardrobe were on one wall and a giant flat screen covered the wall opposite the bed. Various chairs and paintings filled the rest of the room. Two doors led off from the bedroom which she assumed was a bedroom and closet.

"Are you ready, Katie?" He asked her.

"Yes, Mr. Murp..."

"Please call me Nick." He interrupted her.

"Yes, Nick." She said, nervously.

Nick walked across the room and sat down in an armchair, beckoning her over to stand in front of him.

"Strip." he said, calmly.

"What?" Katie asked.

"Strip." He repeated, more firmly this time.

Katie swallowed nervously. She had no idea how to strip. She had never done anything like it before. She had seen plenty of porn videos though so she just decided to try to imitate what she had seen some of the girls in those do. She crossed her arms and grabbed the bottom of her t-shirt, slowly pulling it up and over her head and dropping it to the floor beside her. She reached behind her back and unclasped her bra, gently lowering it and allowing her breasts to come into view. She blushed as she saw Nick's gaze drop to her now bare chest.

"Keep going." He instructed.

Katie unbuttoned her jeans and unzipped them. She turned around to face away from him and slowly, ever so slowly, inched her jeans down her hips and over her bubbly cheeks. She went as slowly as she could, bending at the waist as she went to give him the best show she could. When her jeans were all the way down, she stood back up and stepped out of them. She repeated the same progress with her panties, wiggling her hips as she slid them down over her butt and stepping out of them before turning around to face him. She nervously crossed her arms in front of her chest but dropped them when he motioned for her to do so.

Nick slid off his dress shoes without bothering to untie them and stood up. He removed his suit coat and unbuttoned and removed his shirt and tie as well. Katie was impressed by how well built he was. His chest and abdomen were as immaculately cut as his expensive suits were. She drew a sharp breath in as he stepped toward her. He towered more than a foot over her tiny frame.

"Take off my pants." He instructed her and stood with his arms crossed in front of her.

Katie stepped up and slowly reached for the crotch of his pants. She fumbled with the belt for a few seconds before unfastening it and releasing the buckle. Then she took hold of the zipper and, with trembling hands, zipped it down. The pants slid down his muscular legs and he stepped out of them. She could already see a bulge forming in his boxer briefs and it looked quite large.

He stepped forward and took her face in his hands, leaned down and began to kiss her. After a couple seconds, Katie began kissing back. His lips were firm yet gentle and his tongue pushed past her lips and dominated her mouth. She closed her eyes and began to lose herself in the intense making out. She could feel his hands roaming her body a bit. One hand reached between them and took hold of her right breast. Her small B cup was barely a handful for his large palm but he gently squeezed and massaged it, tweaking her nipple and making her gasp into his mouth. His right hand traveled down her side and over her hip. It was soon joined by his other hand and he cupped and squeezed her cute butt. Katie lost track of time as she began to melt in his arms but eventually he broke the kiss, leaving her breathing heavy and flushed.

Nick walked past her to a nightstand next to the gigantic bed and opened the second drawer. Reaching in, he pulled out a couple things which she could see were handcuffs and some other object that consisted of leather straps and some metal parts. He walked up behind her and gently pulled her hands behind her back, cuffing them securely there. Reaching up to her face he took the other object, which she now saw was a ring gag, and held it in front of her.

"Open." he commanded.

Eyes wide, she obeyed and opened her mouth for him. He fit the ring between her teeth, forcing her jaws open quite wide, almost uncomfortably so, and fastened the straps around her head. Now unable to close her mouth, she could already feel the saliva building up. Nick returned to sitting in the armchair and beckoned her forward, pointing to the floor in front of him. With some awkwardness, Katie dropped to her knees where she was told and awaited instruction. Nick took hold of his briefs and slid them down and off his body.

Katie gasped as his cock came into view. It was massive. Far bigger than the two boys she had had sex with and bigger than most porn stars she had seen. It was incredibly thick and even without being fully hard, at least 6 and a half inches.

"Lick the sides and head." Nick told her.

Katie inched forward between his legs and leaned forward as best she could without her arms. She did her best to extend her tongue past the ring in her mouth and began licking up and down the sides of his shaft. Saliva leaked past her lips and spilled down her chin as she worked. She worked her tongue around his head and teased the tip. She didn't have much hands-on experience so she was working off what she had seen in pornos to do her best to please him. She could feel him slowly but surely hardening beneath the ministrations of her soft, wet tongue. Soon he was at full staff. Katie stared up nervously at his monstrous member. At full length, it exceeded nine inches and was immensely thick. She didn't know how it was ever going to fit inside of her tiny body.

"Start sucking now." Nick said and Katie obeyed.

She moved her head up over his attentive pole and lowered her open mouth onto his bulbous head. His cock barely fit through the ring stuck in her mouth. The head of his penis alone entirely filled her tiny mouth and there were still more than eight angry inches behind it. She began to suck as best as she could on the head and used her tongue to swirl around it. He allowed her to continue like this for a minute or so before giving her more instruction.

"Deeper."

Katie looked up at Nick and met his eyes with hers. She didn't think much more of this gargantuan could fit in her mouth but she knew what he expected and pushed her head further down on him. Every millimeter felt like an inch to her as she progressed slowly downwards. She only managed to get another inch and a half in her mouth before it hit the back of her throat, triggering her gag reflex. Her eyes water and a tear formed in her eye. Katie pulled off his cock, panting and looked up at Nick. Nick reached down and cupped her chin in his big hand. He wiped away the tear from her face with his thumb.

"Again." He commanded, calmly but sternly.

Katie once again began to suck on the head of his cock and now took a bit more in each time she went down. She knew that two and a half inches was her gag point so she bobbed up and down, taking just the first two inches in her mouth. Saliva dripped past the ring and drool dripped down his shaft. Nick watched passively at her attempts to suck his cock for a few minutes, letting her get her bearings around his dick. After a few minutes, he placed his hand lightly on top of her head. Katie stopped her movements and looked up at him.

"I want you to take it as deep as you can and hold it." He told her.

Katie nodded slightly and took a deep breath, preparing herself. She began to push her mouth down over his shaft once again, going to her limit. Once again, at about two and a half inches, his tip struck the back of her mouth and she gagged. She reflexively tried to pull back but Nick suddenly tightened his grip on the back of her head and pulled her back down. She whined and peered up at him through watery eyes.

"I said as deep as you can go and hold it. Go deeper." He said, more aggressively.

The hand on her head applied more pressure and suddenly, Katie felt the massive sausage in her mouth begin to slide into her throat a bit. She gagged again and whimpered trying to pull back but Nick strong arm easily kept her down. Nick forced her to take another inch down her gagging throat for a grand total of four before stopping. She could feel her throat beginning to bulge a bit below her chin. He held her there a couple seconds before relenting and releasing his grip. Katie flew off his cock and began coughing and gagging. She leaned back and gasped in large breaths, her eyes watering. Nick stood up from the chair and leaned down to her. He took her chin in his hand, turning her to face him.