The Contract Specialist - Cover

The Contract Specialist

by Fish Taco

Copyright© 2022 by Fish Taco

Erotica Sex Story: Lilly never dreamed she would get hired for such a great job right out of high school. She wasn’t informed of the full job description.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   NonConsensual   Reluctant   Heterosexual   Anal Sex   Oral Sex   Tit-Fucking   .

Lilly Flowers hummed to herself as she brushed her long dark hair in front of the bathroom mirror while wrapped in a towel. She could barely believe it. She graduated from high school only a month ago with no idea what she wanted to do and now here she lived in this company-provided apartment and starting her new job at WildAcme this morning.

She had been a top student in high school with almost all A’s but she couldn’t afford to go to college. Her parents couldn’t take on student loan debt and what scholarships she qualified for were not enough to pay for one semester at a university, let alone a four-year degree.

Yet, here Lilly was at only eighteen starting a job this Monday morning as the executive assistant to the president of WildAcme, John Longwood, and she would be trained to be the number one contract specialist for the company. She didn’t know exactly what the latter meant but they said she would be trained and it mostly involved making sure contract agreements with other companies were completed. She looked forward to the training because she had no knowledge of corporate contracts which made it all the better knowing they still hired her. WildAcme obviously saw her potential from her school grades.

Lilly put the brush down on the bathroom counter. She took off the towel, hanging it on the bar. She returned to the mirror. She gazed at all five foot one of her naked body. She had large double-D tits that always gave her body a small jolt of pleasure when she touched them. A high school boy once snuck in a squeeze and she was embarrassed by how loud she gasped. She touched her bare mons then slid her fingers further down. She opened her pussy lips. One day she would find the right guy to let inside her. Boys had hoped to be the one to be her first and to touch her large tits but they were all so immature. She was a woman now and she was ready for the right man. She had wondered if it would be at college but now she knew she would meet the right man in this new city. He was out there and he could be in a dance club or a grocery store or even at a SaleMart.

Lilly arrived at work dressed in a white blouse, a dark green blazer, and a matching dark green pencil skirt. She wore black, low heel shoes. She remembered them saying something about a clothing allowance during the interview but she certainly wasn’t going to mention it anytime soon. She had received so much in such a short amount of time.

The first part of her day was as boring as possible. She spent all morning in HR. She received her access badge and she took training after training after training. Ethics, diversity, harassment, safety, security. Tedious and dull. After lunch, she had a few more HR tasks to complete until she finally could go up to the ninth floor, the top floor, of the Wild Acme building.

The elevator opened up to double glass doors straight in front of her. She went through and headed to the desk in the middle of the room. The desk had a computer monitor and papers and also a nameplate. The first line said “Lilly Flowers”. The second line said “Contract Specialist.” Lilly’s heart felt warm. She already had her place and she liked that it said “Contract Specialist” over “Executive Assistant”, not that there was anything wrong with “Executive Assistant” but “Contract Specialist” sounded more important.

She sat at her desk. The chair was very comfy. To her left were two double doors and the sign on the wall said, “John Longwood”. To her right were also two double doors and the sign said “Executive Conference Room.” She surmised this was probably where contract negotiations happened.

Lilly tried to login to the computer with the username and password HR provided but with no success. She stood and walked over to Mr. Longwood’s office. She hesitantly knocked. She didn’t want to disturb him but he’d probably want to know she was here.

“Come in!”

She slowly opened the door. He was on the phone. He waved her in. Lilly stepped inside. He held up a finger. Lilly stayed motionless.

Mr. Longwood had been part of her interview during career day toward the end of her final days in high school. She later heard it was unusual for a company president to show up. The other companies only sent HR people. The man was in his 50s with some slight graying at his temples. He was tall and still lean. He looked pretty good for being a really old guy.

“Yes, I know we can come to an agreement,” Mr. Longwood said. “I have a new contract specialist that started today and I’ll have her ready to meet you on Monday and seal the deal.”

Lilly’s stomach fluttered. Could she be ready in a week?

“Excellent! See you on Monday.”

John hung up.

“So Lilly, how has your first day at WildAcme gone so far?”

“Good,” she replied.

“Really? I think having to spend all day in HR is miserable.”

Lilly flushed and gave a small smile. “Yes, sir.”

“Hey, I’m John. I’m just a normal man. We’re on a first name basis.”

“Yes, s-, John.”

“I just got off the phone with Hikaru Yagiwong of Yagiwong Enterprises. They’re going to supply us with some specialized microchips and we’re going to sign the contract next Monday so can you send him an email reminder? His address will be in contacts.”

“That’s why I knocked, sir.”

“John,” he corrected.

“Sorry. The password they gave me doesn’t work.”

“Call IT.”

“What’s their number?”

“It’s on the sharepoint.”

“I can’t login.”

“Oh, right.” He clicked on his computer then wrote on a sticky note. He held it out. “Here you go.”

Lilly walked up to the desk and took it. She was almost out the door when he called out.

“Are you ready to start contract training right away?”

“Yes, sir. I mean, John.”

“You better start getting that right or I’ll have to give you a spanking. Would you like a spanking?”

“Uh – no,” she said, flustered by the strange question.

“Ok, we’ll find out later. Let me know when you’ve emailed Yagiwong.”

“Yes,” she slowed down. “John.”

Mr. Longwood’s phone rang and he picked up. She closed the door behind her.

IT got her logged in after having to reset her password twice. She found John’s calendar and the meetings he was scheduled for. Julie from HR had told her during check-in that there were things he kept off his main schedule and they would be just listed as “unavailable” with no explanation or reason. Lilly thought it made sense that the president wouldn’t want to have everything listed.

Lilly went through her computer and got a feel for the document filing procedures. She found policies and documentation on the sharepoint and became knowledgeable of Mr. Longwood’s official schedule. A couple of department heads came in and gave her a big friendly greeting and smile before going in to see the president.

Just before 4 pm, about an hour before the end of Lilly’s first day, she received an IM requesting her to come into his office. She didn’t have much to do right now and tried to stay off her personal phone so she was happy that she would have something to do.

He stood, semi-sitting against the front of his desk when she entered.

“Come here,” he said, waving her forward.

Lilly stopped a few feet in front of him.

“I’m sure you know why I hired you as a contract specialist,” John said.

Lilly didn’t know what to respond. Part of her wasn’t sure to be truthful. She was happy to have the job. “My grades?”

He laughed which disconcerted her. “You’re not a dumb rock so that’s a plus but no that’s not the reason.”

Lilly felt afraid to answer. What if she said something that cost her job?

“No, the moment I saw you,” John said, “I knew I had to hire you as my personal assistant and contract slut.”

Did he say slut? She must have misheard.

“What do you have that every guy wants?”

“I don’t know, sir.” Lilly felt more anxious by the second.

“What are they? Double-D’s? And on such a small body?”

Lilly didn’t know what to say. He clearly was talking about her breasts.

“Let’s find out.”

In a flash, he grabbed her wrist and pulled her into his arms. He spun their bodies around and sat her ass on the desk. He reached his hands into her blouse and pulled violently. Buttons flew everywhere.

“Oh, yeah,” he crowed. His hands went under her now open blouse and reached behind.

“Don’t,” she protested softly, feeling his hands on her bra clasp.

Lilly’s bra sagged and he pulled the cups underneath her big firm tits.

He grabbed the side of each tit with his hands and she let out a shocking gasp.

“These are magnificent!” he praised. “So firm when so young.”

“Doooon’t,” she said, barely above a whisper. His hands squeezing her tit flesh caused pleasure shocks throughout her body but especially inside her pussy.

He pushed her tits together and brought his mouth down on her right nipple. He sucked and made it a hard firm point. Lilly moaned and her head arched back. He moved to her other nipple and did the same. She moaned even louder.

“You love this!” he declared. “You love having your tits played with.”

“Nooooo,” she said with limited strength. She slowly shook her head back and forth.

“I thought you’d be reluctant like my previous assistants but you want this!”

“Nooooo. Doooon’t. Please stop.”

Lilly didn’t want this. She didn’t want him touching and fondling her tits but she couldn’t deny the pleasure she felt. What was happening to her?

He took off her blouse followed by her bra. She sat topless on his desk now. He grabbed her tits and plunged his face into cleavage. He pressed her tits against his cheeks. She felt his tongue licking her skin between her two huge tits. The touch caused her to push forward to try to drive his face deeper into her valley. His tongue on her tits felt incredible. She felt moisture seeping out from between her legs. He pulled his face out much to her relief but also to her frustration.

“Now I’m going to give you what you really need!” he said ravenously.

Lilly felt his hands unzip her skirt and he slid it off. He removed her shoes at the same time. Next his hands went to her everyday white panties and he ripped them until they could slip off.

“Please don’t, Mr. Longwood,” she pleaded. She was completely naked now.

“You want it. I know you want it.”

“Noooo!” Lilly didn’t want his cock inside her pussy. She wanted to save her pussy for her future loved one and hopefully the man she would marry.

His fingers touched her pussy and she gasped.

“You’re so wet already. Your cunt needs cock.”

“Nooo! Please don’t – John.” She hoped using his name would dissuade him. Lilly felt his fingers open up her lips.

“What’s this? A virgin! You are definitely my best assistant ever!”

“Don’t do this! I’m saving myself.”

He grabbed her tits and began squeezing. Lilly moaned loudly.

“Sounds like a girl who needs a big hard cock inside her.”

“No, no, I don’t want that!”

John removed his hand from her tits and opened up his pants. He pulled down his pants and briefs and out popped eight inches of big hard cock pointing right at her. He pushed her top half back so she had to hold herself up by her arms. She watched his big hard cock approach her pussy. He was going to try to stick that giant thing inside her little pussy.

“Doooooon’t!” she begged again.

She saw his eyes were completely focused on her virgin pussy. She shuddered when she felt his cock go between her lips. She screamed as his cock ripped away her hymen. She felt the intruder go deeper and deeper. How deep could it could go in her? He stopped and Lilly looked down. She had all eight inches inside her pussy.

He started to thrust. With his hands holding her waist, his big hard cock moved back and forth inside her formerly virgin pussy.

“You have a nice tight cunt!” he complimented.

“No! No! Don’t fuck me!” she pleaded in dismay.

“I know you want it.”

“Noooo! Take it out!”

“You have a body made for fucking with a sweet pussy made for cock.”

“Don’t talk that way!”

“It’s the truth. You wanted my cock since you first came into my office.”

“No, no, that’s not true!”

“Maybe not but your pussy already was soaked. You love my cock in your cunt. You’re glad I took your virginity.”

“Noooo!” she replied but it sounded more like a moan.

“You’re going to cum. This is your first time and you’re going to cum.” He sounded triumphant.

“No, no,” she said weakly. His cock thrusting inside her pussy, rubbing against her gripping walls felt so incredibly wonderful. This was a feeling and sensation she never felt before and she wanted it to continue to grow stronger.

“I didn’t know you were such a slut but now I know. You are perfect for this job.”

“Don’t call me that,” she begged, as ripples of pleasure emanated from her pussy outward to the rest of her body.

“Slut? That’s what you are. You love my cock fucking your pussy, don’t you?”

Lilly couldn’t help herself. She moaned more and more but managed to moan out, “Nooooo!”

“You’re a little slut than wants to cum.”

“No, don’t make me cum.”

“I’m not making you do anything. I know you want to cum.”

Lilly didn’t protest. She chose to stay silent because he was right. She wanted to cum. His big hard cock made her get closer and closer to the cum she wanted to experience. This felt way beyond anything she ever did on her own with her clit.

His cock abruptly pulled out all the way. She mewled and looked down her body at the wet, slick monster that was inside her.

“Do you want it back inside your cunt?”

She slowly and reluctantly nodded, feeling ashamed that she wanted him to continue fucking her and wondering if she was a slut like he said she was.

He smiled and jammed his cock back into her. “Slut!”

He resumed thrusting and his hands moved up and gripped her tits. She felt like her body was on sexual overload. Pleasure was a consuming fire. She moaned loudly. His cock in her little pussy felt so tremendous. He was going to do it. He was going to make her cum! She didn’t want to cum from being forcibly fucked by him but she so desperately needed to cum. She needed his cock thrusting in her pussy and his hands tightly grabbing her hyper-sensual tits. His cock kept moving faster and she couldn’t stop it if she wanted to. She was cumming!

Lilly let out a tremendous moan and liquid gushed out of her pussy and during that same moment of her cum, she felt his cock stop deep inside her. His big hard cock violently throbbed against her inner walls and she felt a huge amount of his cum pour out into her. It continued to spasm, putting more and more into her until she could feel it dripping out of her. His cock stayed motionless then she slowly felt it retreat and she watched it exit her. His white, warm, gooey cum coated her pussy lips. It felt like he put so much in her.

“Your little pussy feels magnificent, slut!”

“Please don’t call me that!” she said, looking away. He fucked her and she came. She came so hard. It was the best cum of her life. Yet now she couldn’t give her virginity to her future husband.

“You’ve earned it. I heard you. You loved it. I never felt a pussy release so much juice and squeeze around my cock so tight during her cum.”

Lilly worried he was right. She had cum so hard. She must be a slut.

“Come here,” he said, sliding her off the desk. “I have to try your amazing tits. You love it when I touch them.”

Lilly felt more shame. It did indeed feel so good when he grabbed her tits and sucked on her nipples.

“Lie down,” he commanded. “On your back.”

She sank down to the carpet as John moved the two chairs in front of his desk out of the way then completely undressed. He stood over her, his legs on each side of her. She watched his cock that had lost a little length and firmness after exiting her pussy grow back into his eight inches of big hard cock. He dropped down, straddling her and plopping his cock between her tits.

“Push your tits together,” he said.

She didn’t hear him. She was mesmerized by the warm and heavy feel of his cock on her chest.

“Push your tits together!” he said frustrated, grabbing her hands. He put them on each side of her big tits and pushed. “Hold them there.”

Lilly understood once he started thrusting, his cock head popping out of her tit canal but she really understood because his long shaft rubbing against her inner tit flesh felt wonderful. She squeezed even tighter.

“That’s it,” he gasped. “A nice and tight tit cunt.”

She watched the head of his hot cock appear and disappear. This was what it was doing inside her pussy just a few minutes ago and making her feel the best she ever felt in her life. She gasped as he continued to titfuck her.

“I’ve never met anyone with as erotic tits as you.”

He didn’t say it but Lilly said it in her own head. She must be a slut. Maybe he was right. Maybe she subconsciously wanted his cock and he sensed that and that’s why he raped her. But then it wouldn’t be rape. While he fucked her, she wanted him to keep fucking her because his cock felt so good inside her pussy. No, no, she was thinking wrong. He shouldn’t have forced himself on her. He shouldn’t have done it. It didn’t matter, she-

Lilly moaned and all other thoughts left her mind. His wet cock drooled out more liquid making it easier and easier to slide between her tits. The rubbing against her tits felt so good but her body knew it wanted more.

John reacted to her physical response. His hands gripped each nipple and pulled. They became hard points and he rolled them between his fingers which brought a mixture of pain and - she cried out loudly, arching her back. His touch felt astounding and his hot thrusting continued to feel incredible. She was cumming again! She was a slut!

She arched up again and became rigid then cried out loudly while juices gushed out of her pussy. She collapsed down as his cock became a blur between her tits. She felt tired but managed to keep her tits pressed around his cock.

“Oh, fuck! Oh, fuck!” he groaned.

His first blast splattered cum on her nose and lips. The rest of another large cum load covered most of her neck. It felt warm and sticky.

“Damn!” he said. “Now that’s a titfuck.”

He got off her and looked down at his cum on her neck and face and the previous load coating her cunt.

“That was a good first day, Lilly. You may get dressed and go home.”

She sat up. Her panties were unwearable and her blouse wouldn’t close. “How am I supposed to go out wearing that?”

“You’re not. I have new clothing for you. You will find when you get back to your apartment that I’ve had your wardrobe replaced with what is appropriate for you to wear in your position.”

John went to a drawer and pulled out a top and a skirt.

“Put this on.”

The skirt was short. Very short. She couldn’t bend without exposing herself.

Lilly moved toward her bra but John snatched it off the floor and tossed it to the other side of his desk.

“No bras, no panties. All your wearing are the skirts and tops you’ve been provided as part of your clothing allowance. You get to decide on your shoes but they must be easy to slip off.”

She put on the top. It plunged deeply so most of her recently fucked tits were visible. The material made her nipples hard. The top felt embarrassing but what was more embarrassing was the top’s material made her feel semi-aroused because of the pressure on her nipples.

Back in her apartment, Lilly felt confused. Mr. Longwood shouldn’t have fucked her. He shouldn’t have put his cock inside her pussy. He shouldn’t haven’t put his cock between her tits. However, she shouldn’t have cum from being fucked for the first time by a man she didn’t want to fuck her. She shouldn’t have cum from his cock thrusting between her tits. Most of all she shouldn’t be thinking about wanting to experience the amazing feel of cumming again. It was shameful how she responded to his fucking. She shouldn’t want it to happen again.

She looked through her new clothing. Everything was a short skirt and a revealing top. She would have to dress like a slut. She wasn’t certain this wasn’t how she should dress. She feared that she might really be a slut.


Lilly felt very self-conscious walking through the lobby of the WildAcme building. She hurried to the elevator ignoring the leers of the security guard at the front desk and the stares of the men arriving for work. She waited for the car to open. She tried to ignore that the man standing behind her stared at her ass. The dark blue skirt barely covered her ass. The elevator doors opened and she entered.

Lilly went to the back corner after pushing the button for the top floor. Three men and a woman in a power suit also entered. The man she thought stared at her ass stood next to her even though there was plenty of room in the car. He gazed down at her ample tits, barely held in by the top she had to wear.

“Are you Mr. Longwood’s new assistant?” he asked.

“Yes, I’m a contract specialist.”

He chuckled. “You have the looks to be very good at it.”

Lilly had no idea what that meant. Politely she said, “Thank you.”

“No, thank you for the show. I hope to see you around.”

The doors opened and he and another man exited. After the sixth floor, she rode alone to the top.

She logged into her computer and checked her emails and John’s schedule. He must have noticed that she was logged in because she received an instant message asking her to come into his office.

Lilly gave a courtesy knock and entered. John smiled broadly. She walked forward.

“You looked fucking gorgeous!” he said. “Just like a contract specialist should look.”

“May-may I ask a question?” she said nervously.

“Of course. Come over her to my side of the desk.”

Lilly felt anxious as she moved around his desk. “Why does it matter how I look as a contract specialist?”

“We make agreements with powerful companies run by powerful men who appreciate a beautiful woman. Yagiwong is a man and like most men, he is more willing to negotiate fairly in the presence of a beautiful woman. You will seal the deal.”

Lilly didn’t like that it was her looks that helped establish a contract but she understood that the business world was still primarily a man’s world. Mr. Yagiwong would probably stare at her tits the entire meeting. The thought made her uneasy.

“Get under my desk, Lilly.” He rolled back in his chair

She looked at the opening under his desk then at him. “Sir?” she said confused.

“Sir? What is this? Do I have to slap that cute bottom of yours?”

The thought revulsed her. “No. I – I don’t understand.”

“Get down under my desk. I thought about your hot body all night and woke up with a raging hard-on so I need you to suck me off.”

Lilly swallowed. His cock in her mouth? The thought forced her to suppress a gag.

John stood quickly and grabbed her wrist. He pulled her closer then with a hand on her shoulder, pushed her down, guiding her under his desk. He sat back in his chair and scooted back up, trapping her underneath. His legs were open, one on each side of her. He undid his belt, opened his pants, and pulled down the zipper. He lifted his butt and pulled down his pants and briefs to just below his knees. He put his bare ass back down on his chair.

Lilly gasped. All eight inches of his big hard cock was in her face. How did this monster thing fit inside her pussy yesterday? It looked absolutely huge this close up.

“Come on!” He sounded impatient. “Start sucking!”

He grabbed his cock and the hair on top of her head. He pulled her face toward his cock. The tip pushed against her nose. He slid it down to between her lips. He forced her mouth onto it. His cock felt so hot in Lilly’s mouth. The warm flesh rested on her tongue.

“Close your lips and suck! I have phone calls to make.”

She closed her lips and slowly moved back and forth on it. Up above she heard, “This is John Longwood of WildAcme. I need to talk to your CEO, Gunther Muller.”

She continued to move on his cock, casually hearing John talk about some product quality issue. He made several more calls over the next many minutes. During that time, an increasing amount of sticky liquid accumulated in her mouth. She swallowed it down and soon discovered she had to swallow more often as his juices filled her mouth faster.

Lilly heard him end a call. He reached down and grabbed two handfuls of her hair. He thrust for almost a minute when the phone rang. As she kept sucking his cock, she could hear his gasping voice as he tried to talk to whoever was on the other end of the call.

The call ended. She looked up and he was leaned back in his chair, his hands behind his head, and a giant happy smile on his face. She kept bobbing while looking at him. He noticed Lilly watching him.

“You’re doing it perfectly. I can tell you’re inexperienced but that’s ok. I didn’t want to cum too fast.”

Lilly didn’t know if she should respond. She was getting a little tired. She didn’t want him to cum in her mouth but she knew it was the only way this would be over. She continued her motion, her lips rubbing against the firm, warm skin of his big cock.

John’s phone rang. “John,” he answered. “Sure, come on up.”

It felt like forever since Lilly went under his desk but she knew it wasn’t really that long. The only way to end this was for him to explode in her mouth. How long did it usually take to make a man do that? She had no idea. This morning she was now no longer an oral virgin. This was one more virginity she couldn’t give her future husband.

“What’s up, Mike?” John said.

Lilly heard another voice. “I want to talk about a couple of issues with the potential Yagiwong contract.”

“Sure. Oh! Let me introduce you to our new contract specialist and my personal assistant.”

John leaned over, put his hands under her armpits, and pulled her up. He stood and pulled her top up, freeing her barely held-in tits, and pulling the top completely off. He spun her around to face Mike.

“This is Lilly Flowers.”

“Nice to meet you,” Mike said. He stood and stuck out his hand.

Lilly felt extremely self-conscious standing topless in front of a strange man. She hesitantly stuck out her hand. Mike shook her limp hand.

“Nice tits!” Mike complimented.

“Look how she reacts when you play with them,” John said.

From behind, he reached around and grabbed the front of her tits in two big hands. He squeezed them. Lilly gasped and felt ashamed. She didn’t want to enjoy the touch of John’s hands in front of this man, Mike. John kept massaging them until she let out a soft moan.

“She has the most orgasmic tits of any tits I’ve ever touched.”

“Incredible! I have to find a girl like her!” Mike said, impressed. “Do you have sister, Lilly?”

“She’s only 13!” Lilly desperately said, trying to fight back the pleasure.

“Oh, well, I guess I’ll have to wait 5 years. I’ll find someone else to replace Julia for now.”

“Get back under my desk, Lilly. You need to finish your job while Mike and I talk business.”

Lilly was happy she wasn’t going to cum in front of Mike but she wasn’t happy about returning to sucking John’s cock.

She heard them talking about some areas of negotiation for the upcoming possible contract with Yagiwong Enterprises. John gasped more and more.

“We can talk about this later, if you want,” Mike said.

“No, let’s do it now. Give me a moment.”

He grabbed her face and held her still as he did several fast thrusts then he stopped and groaned. Her mouth was deluged with a huge amount of cum. For a moment, she felt like she was drowning. Cum spilled out onto her chin and also down on her prominent tits. He released her face. He pulled his pants up and zipped up and refastened his belt.

“Ok, Mike. I can give full attention to our discussion.” He looked down. “Go clean up, Lilly. I’ll let you know when I need you again.”

She climbed out from under the desk. He held out her top. She took it, covered the front of her tits, and hurried out.

“Such amazing tits!” Mike complimented.

“Sure are. Decent cock sucker too.”

She didn’t hear anything else. She was out by then. She hurried to the bathroom.

After cleaning up, she returned to her desk. She couldn’t completely get the salty and bitter taste of his cum out of her mouth no matter how much she swished water. She felt so humiliated to be sucking his cock and having her mouth overflowing with cum while he chatted with another person in the room. It was bad enough to have to suck his cock but to do it while another person was there made it worse.

She settled into her job. She answered emails, scheduled appointments for Mr. Longwood, and forgot about the morning events.

Lilly was about to head to lunch when an instant message popped up. “Lilly, I need you.”

 
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