Helping Mr. Penn...... (Closed)

[ella_v]

The young woman didn’t know what to make out of Mr. Penn’s ‘you look like that’. However, she had to admit to herself, that she had enjoyed the attention that she had gotten from all the men. Actually, she kind of like the look and wanted to stay in the dress for the time being, just to have a bit more fun. And seeing those additional $2500 in her hand, made the young graduate look more relaxed on Mr. Penn’s methods.

Once at her office, Ella started right away to process the paperwork. She made copies of the contracts and filed those away. Then she gathered the paperwork together, got her keys, and drove into the city to meet that lawyer. Ella had been surprised to hear that the lawyer was female, so she was even a bit curious what kind of person she might be.

Half an hour later, she parked her Jaguar and made her way into the office, still dressed in her white, revealing outfit. She walked over to the receptions desk and smiled at the young woman behind it. “Hi, I’m Ella Thompson, Mr. Penn’s personal assistant, I would like to speak to Mrs. Jackson. I have some important documents for her.”

 

[Steve5511]

Steve got out of his suit and into his swim trunks. Even though he was 43 he still has his tight muscular body so he was comfortable without a shirt. He grabbed a towel and made his way to the pool.

Once there he dove right on and took a few laps. The water was cool and refreshing as made his way doing his workout. Once his laps were done he popped out of the water and played on one of the lounges in the sun.

As he closed his eyes and began to dose off, he couldn't help but to think of Ella in that outfit. His mind ran up and down her body and his cock started to get hard at that thought. He pictured her standing with her hands on her hips knowing that she was making him hard. In his mind he then started to kiss her long legs from her heels right up to the hem of her skirt. In reality, his cock was now at it's full length and harder than it had been in a while.

 

[ella_v]

Mrs. Jackson turned out to be a very good looking, black woman in her mid 30s. She eyed Ella with a raised eyebrow when she saw the sexy new assistant. It was clear to hear, why Mr. Penn had hired this one. However, she had to admit, that the old man had quite a good taste.

The two women quickly got through the documents and soon Ella was back in her car, driving back to the house, with the satisfying feeling of a well done job. When she was parking her car outside the mansion, it was already mid afternoon. The weather was great and Ella decided to spend the afternoon in the sun, if Mr. Penn didn’t have any other jobs for her to do.

She walked through the house, searching for her boss, remembering that he was planning on going to the pool. When she stepped outside to the pool area, she saw him lying on a lounge chairs. She walked closer, when she realized that he was asleep. Her eyes moved over the older man, he wasn’t in the best shape, but he wasn’t bad looking at all. When Ella’s eyes reached his lower body, she gasped.

Mr. Penn had obviously an erection, but what was really shocking was the size of the tent it formed. “Oh my god… that’s… huge.”, mumbled the 23 year old, wondering how well her boss was endowed. She blushed at the though and turned to walk silently away, not to wake Steve up and to cause an awkward situation.

 

[Steve5511]

By now Steve's daydream had gotten Ella out of her dress but she still had on her heels and sunglasses. He had licked and sucked on her firm and amazing breasts. His tongue made circles around her hard pink nipples. Her yits fit perfectly in his hands as he began to kiss her neck and onto her lips.

As he lay in the sun, his cock was trying to bust out of his shorts. The tip started to peek out from the waistband but he was still confined. Then for some reason he thought he briefly woke up and saw the amazing sight of Ella walking away from him. Her teardrop ass looking even hotter because of her heels. Was this part of the dream too?

 

[ella_v]

Without noticing anything about Steve’s short wake-up, Ella walked back into the house and to the first floor, where her rooms were located. She was unsure whether she was supposed go to the pool, while her boss was around. Especially since he was in such a delicate state at the moment. Her mind flashed back to the very impressive tent that Steve’s short had shown. Ella wondered how big Mr. Penn’s dick would be in its full glory. Although she tried hard to shut that though out of her mind, she wasn’t really successful doing so. Frustrated she walked to one of the windows, which faced the pool area, her boss was still sleeping in the sun and Ella imagined that she even could notice his hard on from up here.

She was still unsure, whether she should go to the pool or not. In the end her curiosity won. So the young woman stripped out of her white, sexy dress, her high heels, and her thong. She looked at her naked body in the mirror and couldn’t stop herself from smiling proudly. Then she got her new bikini and slipped into it. The panties were in a bright neon orange, while the triable bikini top was black with white cup insides. The swimsuit were not outrageously sexy, but in combination with her lightly tanned skin, it looked really good.

After grabbing a towel from the bathroom, she walked with her flip-flops back to the pool area. When she was close enough she slipped them off, to make no unnecessary noise and tiptoed closer to the lounge chairs and her sleeping boss. She placed her sunglasses and other stuff on the chair next to him, before her eyes darted back to his shorts. Her jaw dropped, when she noticed that the thick crown of the hard cock was peeking out from the waistband. Ella gasped in disbelieve, “It’s so dark and… and… HUGE.”

 

[Steve5511]

After a while Steve started to wake from his afternoon slumber. Unfortunately for him, his cock had been awake for a while. Turning his head he saw Ella's long and lean body laying in the lounge next to his. His mind quickly became aware of his hard on and he quicker than lightning jumped back into the pool.

His big frame made a big splash as he jumped in. He didn't know if Ella had seen his erection but he was kind of safe now. Pretending that he didn't notice her he took another lap and then just relaxed near where the lounges were. He hoped that she didn't catch him looking at her but part of him did.

 

[ella_v]

After taking a good look at Mr. Penn’s hard dick in his short, Ella had made herself comfortable in the chair next to him. She enjoyed the sun, red a book, and glanced over to her boss and his constant hard on from time to time. It was impressive how long that older man could stay hard. “He either has an impressive stamina or he hasn’t gotten any in ages.”

Ella even wondered what or who had gotten her boss so excited, when she noticed that he was waking up. Quickly she acted like she had noticed nothing. But she couldn’t stop sniggering when he jumped up and raced to the pool like he being hunted by hundreds of angry wasps.

When he had finished his sudden swim, Ella go up from her lounge chair and walked over the pool. She sat down at the edge and placed her feet in the water. She smiled at him and leaned back on her arms, pushing out her chest. “Did you have a relaxing nap, Mr. Penn?”

 

[Steve5511]

Steve couldn't help but look at her perky tits as she almost presented them to him. He also wouldn't have minded just swimming up to her, spreading her legs and diving right in. He then wondered how trimmed or shaved she was. Again his dick started to stir.

"Ah yes... quite refreshing." He managed to blurt out being caught in a daydream. Thinking on the fly he then swam up to where Ella sat, grabbed her legs and pulled her into the water. As he did he said "I told you to call me Steve! Ha-ha"

 

[ella_v]

With a high pitched squeal the 23 year old splashed into the water. She pulled her leg away from Mr. Penn’s grip and resurfaced next to him. Ella gasped for air and pushed her long, wet hair out of her face. “Oh, you are bad, Mr… ah… Steve.” She splashed some water into his direction in an attempt for playful revenge.

She started swimming a few laps in the pool, since she was now already in the water, she could also spend some time in a meaningful way. However, her mind always returned to the images of Mr. Penn’s hard dick and it’s huge size. Suddenly she had an idea and swam over to him. “May I ask you something personal, Steve? Is there a Mrs. Penn? I mean a guy like you must have someone he loves and spends time with.”

 

[Steve5511]

Steve paused and got a sad look on his face. "I was married once before when I was your age. But she really wasn't ready to settle down and started seeing someone else. After we divorced I jumped into my work and built my small company into what it is today."

Before he knew it Steve was right next to Ella by the side of the pool. He could see her hard nipples pressing against her top but his mind was elsewhere.

"I date now and then but don't have anyone special. Maybe that's also why I hire a lot of women to work around me. For some companionship and most of them tend to try and take care of me a bit. My lawyer who you met today always brings me soup when I'm sick. In return, I make sure they too are taken care of and their families too."

 

[ella_v]

It was surprising to learn that Steve’s ex-wife had cheated on him. Ella wondered why someone would do that, especially if her husband was endowed like Mr. Penn. Hence it could hardly have been bad sex, unless Ella had totally misjudged those tenting swim shorts. But none of that was really the young woman’s business.

However, what made graduate student wonder was Mr. Penn’s confession that he like to hire women, that gave him also companionship and took care of him. Was that rich man hitting on his employees? Or was he even hiring and paying them for physical companionship? That lawyer had been beautiful and surely would have met Mr. Penn’s taste. And Ella doubted that her boss would look after someone’s family for bringing around chicken soup.

All of this was giving the young beauty much to think about. She was curious and disgusted at the same time, but she didn’t want to judge on her boss too soon. “Wow, sounds like you ex made a big mistake back then.” She smiled teasingly at Mr. Penn and studied his face closely before she continued. “So, what does a girl like me have to do, to get you to look after me and my family?”

 

[Steve5511]

“So, what does a girl like me have to do, to get you to look after me and my family?”

Now there was a loaded question he thought. And many answers ran through his head. Most of them right now involved Ella out of that bikini. After seeing that dress she wore today, he couldn't help but wonder what other outfits she had for her sexy body. Maybe he'd have to buy her some presents so he could enjoy seeing her in something else.

"Well loyalty and honesty are big with me" he started his answer. "I don't really have any family so that's why I get close to some of my employees. If they are loyal and honest, hard working and trust worthy... well they become like family."

"I'm not saying that I'm that way with every one of them" he continued. "But like in life, some have become closer than others."

He wanted to add "and those with a body like yours, I want to treat in a special way" but he thought better of it and put his lust for her to the side.

 

[ella_v]

Although Ella could fully understand when Mr. Penn was telling her, she had the feeling that there was something missing in his explanation. It just felt so general, as if it come from a mob boss running his criminal business as well as an amish-parish leader. Additionally, there was a strange look in Steve’s eyes, that made the young woman suspect that the older man was expecting something else, which he didn’t seem to be ready to tell.

The young woman swam to the edge of the pool and pushed herself out of the water. The clear liquid was running down her body and her bikini was sticking to her skin showing every curve of her body underneath. She sat down on the pool’s side again and looked at her boss in the water. Her face blushed a little, when she asked her next question. “Oh, and how close do you usually get to your employees?”

 

[Steve5511]

Ella looked like a girl in a swimsuit calender. Her hair was wet and pulled back. Her hard body glistened with water droplettes. You could just see that her nipples were pushing against her bikini top. Steve wondered how long it would take her to realize the things she could get using her looks and that sexy body.

Swimming to the side of the pool to where Ella was, he positioned himself between her legs. He playfully grabbed her ankles to hold himself there.Her tight bikini bottom clung to her crotch of which he had a great view. Once again he didn't realize that his cock had grown for her.

“Oh, and how close do you usually get to your employees?” she asked him.

He replied "Well that all depends on the employee. Take you Ella... I like you and i'd like to see you do well for yourself."

Steve then pushed himself out of the pool and sat next to her. His trunks clung to his body now and showed off his nearly full erection. This time he wasn't embarassed by it. "If there's ever anything you need or want from me, I'm sure that we could work out some sort of arangement."

He then stood up knowing his bulge was close to her face. He wanted nothing more for her to slide it into her warm and wet sexy mouth and wrap her full lips around him. He'd even be willing to pay her a large sum for it, looking like she did. Steve grabbed a towe and layed on a lounge chair to get back to his dream of her.

 

[ella_v]

When her boss got out of the water, Ella grey-blue eyes went wide. A small gasp was leaving her lips, when she saw the huge bulge up close. The wet swim short stuck to his body and made it pretty obvious to the 23 year old, that Mr. Penn had the biggest cock she had ever seen hidden in his pants. Her boyfriend was no match to this guy and she hadn’t even seen Steve’s dick in its full glory.

Her eyes stayed on the hard swinging rod while her boss moved over to the lounge chair and laid down. Ella even held her breath and she felt the excitement growing in her lower body. Luckily her bikini panties were already wet, so her growing sexual energy was only given away by her hard nipples pressing against her wet bikini top.

She closed her eyes and tried to get control over her body. Then she got stood up and raised her arms to grab her long, blond hair and push it over her shoulder and out of her face. With a smile on her face she walked closer to her boss and looked down at this hard on. “Mmh, well… it looks to me, like you are more in the need of something, Mr. Penn.” She giggled and blushed a little at the same time.

Ella sat down on a chair next to her boss. “So, what kind of arrangement do you have in mind?”

 

[Steve5511]

Steve needed to make the sale here. He needed to throw the facts on the table and let her choose what she wanted to do. He looked over at her sitting next to him and just wanted that sexy body of hers. He also knew that either accidentally or on purpose, she now knew he was sporting some wood.

"You're a bright girl Ella. With all of your business training and such, you probably one day want to start your own business. The one thing that every business needs to start? Money. Of which I have a fair share of if not more. You also happen to have certain assets and abilities that one might find desireable."

He looked over at her again, watching as it appeared that her nipples were getting harder. "Lets put it this way Ella. You made $2500 today in 2 hours for wearing a dress and acting like a little sex kitten. And that's on top of your regular pay and perks. Your business mind should be doing a cost annalysis on that and asking yourself what else you'd be willing to do and for how much."

 

[ella_v]

The 23 year old beauty set up strait and looked with big eyes at her boss. Although she had harbored a hunch all this time, hearing Steve’s implied offer out loud was still a bit shocking. It made Ella feel repulsed and intrigued at the same time, but something stopped her from jumping up and running away. Instead the stayed seated and moved her eyes over Mr. Penn’s body, down to his showing erection in his swim shorts.

Finally, she looked back to his face, there was a deep blush in her face. “So, let me get this straight. You are asking me to have sex with you… for… for money?” This made her feel cheap, but at the same time, it was thrilling that a man of Mr. Penn’s format - and that wasn’t just reference to his huge dick - was interested in her so much, that he was filling to offer her money … lots of money to be exact.

This was a chance to make double or triple of her normal salary on the side, tax free since it was all illegal in the first place. Her heart was beating fast and Ella felt bad for even considering the offer, but before she could even make her mind up, she heard herself ask, “How would this arrangement work? … I mean, what are you looking for… and what would you pay?”

 

[Steve5511]

“How would this arrangement work? … I mean, what are you looking for… and what would you pay?”

Steve smiled to himself. He got her! He was going to turn her into his personal little sex toy. Steve now openly looked up and down her perfect body. So many possibilities.

He didn't want to scare her off and tell her all the things he was looking for from her. At least not right away. But once she got a taste of getting paid to get laid, she'd open up to more. He needed to see right now though if she was serious or just pretending to be.

"Lets keep it simple at first and see how things go." he told her as he tested the waters. "I'll give you $3500 right now if you take your top off and jack me off".

There it was, the first deal on the table. If she didn't go for it or ran away then he'd have to find another assistant. And he didn't want to go through all this again.

 

[ella_v]

Ella sat quietly on her chair looking to the floor and listened carefully to Mr. Penn. She was feeling so confused, on the one hand she wanted to get up and walk away from all of this, but on the other hand, there was a lot of money on the table for a fairly easy task. Sure her boyfriend would go crazy if he ever found out about it, but she was hundred of miles away from him.

She bit her lower lip and thought hard about what she should do. There was a part of her, that wanted to enter into this fateful adventure. Ella had always been the good girl, who studied hard, kept her nose clean, and never missed an 8:00 am class. Now, seeing that older guy - who could be even her father - with his huge, hard dick in front of her, was making her to seriously consider Mr. Penn’s offer.

Finally the 23 year old looked up and smiled at her boss. “So… you are going to pay me $3500 for just giving you a hand job while being topless?” When he nodded, she sat still with her heart racing, finally she slowly nodded her head.

Ella though she was going to be sick, when she got up and moved over to Mr. Penn. She threw her right leg over his and sat down on his legs, the huge tent right in front of her. Ella smiled nervously at her boss and moved her right hands behind her back and undid the lock of her bikini top. With her left the held the top in place. She was biting her lip nervously, when she moved her arms ahead, letting her top slip over her shoulders and down her arms, until is fell on Mr. Penn’s lower body.

 

[Steve5511]

When Ella nodded and sat between his legs Steve said softly "Good girl".
Although she still hasn;t done anything, she was on the right track. For now Steve would sit back and relax.

As he knws she would, Ella nervously removed her top. Her face was beet red but Steve knew she would soon embrace it. Ella was still young and inexperienced to know just how sexy she could be. Her hard body was the envy of most women and the desire of most men. She just needed the sexual confidence to take her from "girl next door" to "Porn Queen".

As her top came off she revealed a fantastic set of tits. They were firm and round. Her pink nipples pointing up without a touch of sagging. Steve's cock was almost at it's full length now that he saw her topless.

"My God Ella, you are beautiful" he said to boost her confidence but also he spoke the truth. His cock proved that.

 

[ella_v]

A nervous smile formed on Ella’s lips when she heard the compliment. She pushed her hair once again out of the way and moved her trembling right hand slowly toward Steve’s thigh. She then moved it upward toward the swim shorts, where the tent seemed to grow even more. Softly her fingers traced over the hard pole underneath the textile and the 23 year old was surprised by the hardness and thickness of the still hidden pole.

“Oh my god, Mr. Penn, that feels huge. How is that even possible?” She blushed and bit her lip when she moved her hands to the waistband of her bosses shorts. Her curiosity was beginning to grow strong and Ella wanted to see that huge cock by now. Her small fingers undid the ribbon that sat in the middle of the shorts and than curled around the textile and started to pull them down with growing eagerness. “Please, lift your butt a little, Mr. Penn.” She smiled at him and slowly pull the shorts down.

Her jaw dropped, when she saw the hard pole for the first time completely.

 

[Steve5511]

Steve smiled proudly when his cock came out of it's comfines. He knew that he was blessed with both length and girth. It was always amusing to see a woman's reaction when she first layed eyes on his dick.

Ella's reaction seemed genuine. She could have been putting on a show to make him feel good. But he senced that this was the first time she had seen a monster cock. Plus she probably didn't know how to "play the game" yet. That would come in time.

Now was the time to have her earn her pay. Steve removed his trunks and lay there naked for her. His big cock almost fully engorged. It had been a few weeks since he had cum at the had of a woman so his balls were pretty much filled. He couldn't wait to see how Ella handled herself.

 

[ella_v]

The tick, long pole looked so unreal in Ella’s eyes. Never in her life had she seen such a huge cock. Of cause she knew that some porn actors were incredibly well endowed, but that was another world. But now the 23 year old sat on Mr. Penn’s legs, just inches from the giant erection standing straight up with a slight upward bend. Its thick base was set in dark, slightly graying pubic hair right above a massive looking set of balls.

An overwhelming sensation filled the dirty-blondes excited body. Her small pink nipples were standing at full attention on her round, firm b-cup breasts. Her pussy was starting to become wet just from the sight of the massive, hard dick in front of her. Ella was holding her breath in excitement, when she slowly moved her slightly shaking right hand to Mr. Penn’s ragging hard on. Her finger tips moved over the hard shaft, feeling the thick veins running along its length, moving slowly upward to the thick mushroom head.

Ella’s attention was fixated on the hard pole, her finger tips had reached the leathery skin of the cock’s massive spear head. She licked her lips and smiled nervously at her boss. “Wow, Mr. Penn your cock is so huge, it must be easily more than 8 or 9 inches… and… and it’s so thick.” The 23 year old tried to wrap her hand around the wide pole, but her fingers were not able to close completely around it.

With slow, soft strokes the young blonde started to move her hand up and down on the hard dick. It felt so unbelievable big and was no match to her boyfriend’s dick as well as her four ex-lovers.

 

[Steve5511]

Ella's hands look like those of a child's as she started to hold a real cock for the first time in her life. His dick twitched in excitement as her fingers started to explode the shaft that would make her a real woman. Steve exhaled as she first contacted him. His mind quickly raced through all the wonderful things he wanted to do to her with his huge rod.

Steve knew that he measured just above 10 inches when fully erect. More than a few women had taken out rulers just to know what they were in for. Also some of them for bragging purposes.

Mr. Penn let her start stroking him and get more comfortable with his dick in her hand, She hadn't backed out by now so she probably was in this for real. Reaching to the table next to the lounge, Steve picked up the bottle of baby oil and handed it to her. "Here, use some of this. It will make it easier for you." What he was really thinking was it would help him go into her easier when he finally takes that tight pussy of hers.

Ella already started to get that look of sex in her eyes. Her head was tilted slightly and her full lips were parted. Her firm tits were showing off her hard nipples. His cock stiffened more as he looked at hot hot she was. He could only imagine what she would soon turn into.

 

[ella_v]

It was surprising how well prepare Steve was, but Ella assumed that she wasn’t the first girl that had been corrupted by Mr. Penn’s immoral offer. She took the bottle with baby oil and squeezed some in her left hand. Then she took the bottle and started pouring oil on the huge mushroom head, so that it was running down the full length of the massive rod, looking like sticky, transparent pre-cum.

Ella rubbed her hands together, covering them as well with the slippery oil and started to stroke Steve’s huge cock with both of her hands. In slow long strokes she started to pleasure his dick and started to speed up to a nice, constant rhythm. Her breasts were bouncing up and down with each stroke, but the young woman kept focused on her task and only took her eyes of Steve’s cock to look at her Mr. Penn’s face.

“Oh my god, your cock is so big… do they even make condoms for this size?” She giggled and playfully rubbed with her right hand along the ridge of the big, purple cock head, while her left hand kept stroking the full 10 inches.