Company Retreat

On summer vacation from college, Jenny had taken an internship at a downtown Atlanta office to work at before entering her senior year of college. The 20 year old had gotten a job at an office that managed orders for a mid-level industrial supply company, although her job mostly consisted of odd-jobs such as getting coffee for people and sorting mail. She was excited because despite only working there for three weeks, she was invited to the company weekend getaway in Florida at a luxury hotel next to the beach.

"All ready for the big weekend?" Stan, her boss, said to her smiling. He was always nice to her, and her job had her often running errands for him. In his late fifties, she didn't know much about him, even if he was married or not. He was only a few inches taller than Jenny's 5'6'' height, although he was rather heavy, probably at least 250 lbs. Mostly bald on top, he had a gray and brown beard on his ruddy face.

"I can't wait!" Jenny said with excitement.

Everyone in the office was in a hurry to finish up. It was only Thursday, but they all had Friday off, and the trip would last until Sunday. At 4:30 Jenny left with most everyone else and she went home to pack.

At home, she finished packing with clothes for walking around, and a sexy 2-piece black swimsuit that she had just bought for the trip, which left little to the imagination. Before packing it, she tried it on one more time, just to get a look at it again. Even she knew she looked hot as she viewed herself in the mirror. Her dark brown hair seemed to flow perfectly down her back over her slender shoulders. She thought to herself how her tan looked good now, but she still wanted to work on it when she got to the beach. The bikini top really accentuated her 36 D-cup breasts, which she knew would be the envy of many guys there. She also made sure that her mom and dad didn't see the small bikini since she knew they would tell her no way.

"So what time will you be back?" Jenny's dad began fielding questions to her during dinner.

"Sunday" she replied in a monotone voice.

"And what is the hotel number and address?" her mom chimed in.

The whole dinner was spent with her answering questions, which bored Jenny to death. She couldn't wait just to get out and be in the sun and sand.

She arrived at the airport the next day and said bye to her mom who had driven her. It didn't take long to find her co-workers and soon they boarded the plane. Upon sitting down she realized that she would be sitting next to Stan for the flight. The idea of sitting next to her boss for an entire flight first seemed uncomfortable, but Stan made plenty of conversation and took in interest in her hobbies, much to her surprise. Jenny found out that Stan was married, and had two children, both who lived out of state with families of their own. He had been with the company for almost 20 years and he gave her all the inside information he could. For her part she told him about her studies in school and her future plans, and also mentioned that she had a boyfriend. She had the chance to bring her boyfriend on the trip, but she decided against it. Jenny was unsure if the relationship would last and also, it was supposed to be a "business" trip too, and she figured he may not like it.

They got to the hotel around 1:00 pm, after a quick check-in, that still left plenty of time to swim. They were given the go ahead to have free time for the rest of the day. Jenny had a room that she would be sharing with two other ladies in the office that she really didn't know. She didn't mind because she was quick to make friends, and either way, she wouldn't be spending much time in the room anyways.

Jenny got up to her room and found that the other two ladies had gone elsewhere. She quickly got changed and decided to hit the beach. She changed into her small, black bikini and had to stop again to admire herself in the mirror. She put on blue flip-flops, large sunglasses and a hat, and headed out.

"Wow!"

"Lookin' good!"

"You look fantastic."

"Someone has been spending time at the gym."

As Jenny walked toward the beach in her new bikini, she found herself having compliments laid on her left and right from her co-workers. She swam for a little bit, and then decided to hang out on the beach with her co-workers. They were making drinks, and since no one seemed to care, Jenny invited herself to some, despite the fact that the beauty was only 20 years old.

After two drinks she got to talking about what type of nightlife the place had. Some of the guys and girls closer to her age invited her out to the clubs for the night, so Jenny decided on going and went up to her room to get changed.

She felt a little dizzy at first walking, but she had only had two drinks and it was hardly her first time drinking so she saw it as no problem. She made her way up into her room, seemingly lost in the giant hotel. She arrived to her room and realized that she had forget her keycard, however, she was in luck, as one of the ladies she was staying with left their keycard in the slot when they left.

Jenny entered the room and took off her bra and flung it on the bed. The shower was on, with one of the other ladies possibly planning for a night out too. Not wanting to get stuck in a conversation, Jenny figured she would just get changed quickly and sneak out.

As she looked around, she could not find her suitcase anywhere and she wondered someone had moved it around. She heard the shower go off and decided to ask one of her roommates if they had moved it. Her unassuming attitude changed drastically when she saw Stan, her boss, emerge from the bathroom, completely naked.

Jenny stood there horrified as her boss stepped out of the bathroom. As he noticed her they both stood there for a moment, Stan being completely naked and Jenny only having on the bottom of her bikini with her tits fully exposed.

"What are you doing in my room?" he asked sternly.

"Your room?"

"Yes."

"Oh... my god... I am so sorry... I didn't.." she began stuttering. She was in such a hurry to go out, she didn't even pay attention to where she was going in the giant hotel.

She looked at her boss, standing naked, he had gray and brown chest hair, and some patches of hair on his back and shoulders. As her eyes moved down, she saw his large stomach protruding outward. She gasped when she saw his penis. It had to be around 7 inches and it wasn't even erect.

"You can get into a lot of trouble for this, breaking in here." Stan walked toward her.

"I wasn't doing that... I... I mistook the room." She sputtered out.

"That seems unlikely." Stan was now acting totally calm, he stood face-to-face with her and put one hand on her shoulder, slowly massaging it. He put his other hand under her chin and raised her head up to his.

"I'm going to have to report this, I don't know what you are really doing in here. Trying to spy on your boss?" he said.

"No.. look... please... " She was up against a wall, both literally and figuratively. All she needed was something like this ruining her internship. When she looked down, she saw that his cock had become completely erect, and it had to be 10 inches, and very thick.

"It took me a long time to get where I am, and I don't like little hussies coming in and trying to ruin my career." he said, now sternly again.

Before she could answer he laid down on his back on the bed, his cock still erect.

"You want to come in here naked and spy on me?" he said, "Then I want you take care of this and we can forget this ever happened. Otherwise, I'll have to go down to security and have them look at the cameras showing you sneaking into my room."

"What?!" Jenny exclaimed, still nervous.

"You heard me."

"But... wait... can't we work something out?"

"Yes, and this is it."

Jenny was appalled but she knew that an expensive hotel like the one she was at was sure to have a very tight shift of keeping the guests secure. Also, she was surprised by Stan's sudden change in tone from being her friendly, old boss. She then figured that maybe a quick hand-job wouldn't be such a big deal. In the big picture it wouldn't count for much. Looking at the past, she had gone through three years of college with no drunken escapades or anything like that, which is more than most of her friends could say.

Still nervous, she slowly came toward the bed. Jenny sat down on the bed, still only wearing her bikini bottom. She wrapped one hand around the massive unit, not even able to get all the way around. Then she slowly began to pump up and down.

"No, no..." Stan said, sounding aggravated. He put his hand on her head and began to push it toward his cock.

"Wait... no." Jenny said, startled, "Look my hand will be fine."

"No!" Stan said angrily, "I don't care about a hand-job."

Jenny's face was now only a few inches from the giant cock. She was stunned by the decision, plus she didn't even know if it would be physically possible for her to do it.

"What is it going to be?" Stan demanded.

Trapped, Jenny closed her eyes and decided to make it quick. She only managed to get half of the cock in her mouth and she began to work the rest of it with her hands. She got on the bed completely with her ass pointed in the air as Stan lay on his back.

As she went up and down, she felt Stan place one of his hands on her ass and begin to massage it. She decided not to protest considering what she was doing, if it made him come a little faster it would be worth it.

Jenny couldn't believe the feeling of sucking on her boss. She had never experienced someone who was even close to Stan. She still couldn't even get the entire thing in her mouth, although she was trying harder, as she told herself the reason for her increased effort was all in the interest of getting him off quickly. She cupped his balls with one hand and continued to pump his cock with another. Stan was now aggressively rubbing her pussy and she was very turned on. She took her hand off of his balls and moved to toward her pussy to give Stan some assistance. Stan continued to rub while she stuck one of her finger in her pussy and began to masterbate herself, although Stan did help as his large hands rubbed her.

Jenny let out a loud moan as she reached orgasm. She collapsed on the bed, next to Stan, barely realizing that he had yet to come. The next thing she saw was Stan getting on top of her, as he spread her legs apart. She thought at first to protest but she wanted to feel him inside of her. She saw her boss, above her with his large gut and massive frame shadowing her. He leaned in and began kissing her, his beard felt scratchy rubbing against her as she felt his tongue exploring her mouth. His hands began to roam all over her body, rubbing all over her large breasts.

Stan lined his cock up against her soaked pussy and inserted it half way, and he began slowly thrusting half of his cock in and out. He looked at her face and loved seeing her expression as she let out a soft moan. Then with a sudden change in tempo, he forced his cock all the way in. He began thrusting with amazing speed despite his size, as he loved feeling his cock buried in her tight pussy.

Jenny lay on the bed, he arms stretched out to each side grabbing the sheets. As she looked up she felt repulsed by how her boss looked physically, but that didn't matter for her now as she didn't want him to stop. She reached up her arms and pulled his face towards her as they began kissing while he continued to pound away into her pussy. She felt his weight on top of her as he covered her slender frame completely. Jenny wrapped her arms and legs as tight as she could around him as she was shaken by her second, massive orgasm. As she lay in ecstasy, she felt his cock begin to spasm as he unloaded a torrent of semen into her accepting pussy.

Stan fell down beside her as they looked at each other. He leaned in and they began to kiss again, while their hands explored each others bodies. Jenny ran her hands over his large frame and gut, she was in disbelief to what she was doing. She saw his penis was erect again, so without hesitation she took both of her hands and began to stroke him.

Stan grabbed her and held her tight, pressing her head into his chest as he enjoyed the attention she was giving him. Still, he wanted to take her one more time, so with a sudden burst of strength, he spun her over so she was on her hands and knees. He got behind her and in one motion slammed his cock into her cunt. He reached both of his bag hands around and grabbed her beautiful, D-cup tits and started to grope them. Jenny was immediately turned on again. This time, Stan wanted to really ravage her. He grabbed her silky hair and pulled her head back slightly and he began smacking her lovely, tight ass.

Jenny was now fully into it as she moaned and screamed.

"Fuck me... please.. c'mon, harder..harder! Yes!" She commanded to him. She loved his new found strength as he pulled her hair.

Stan knew they were both close, so he spun her over and holding her ankles as her legs were spread in the air, he felt her climax once again as she moaned, she was now totally spent. Stan quickly removed his massive unit and began jerking his cock over her. Wanting to truly take her, he began to come, spraying his seed all over her luscious tits. Jenny, never having been cummed on, was too far gone to care. When Stan collapsed beside her, she nestled up into his heavy body. They kissed for a little while longer until Jenny fell asleep, with Stan's big arms wrapped around her.