Summer Internship

Story Info
Little sister helps big shot older brother.
5.6k words
4.5
201.8k
80
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
gymmyt
gymmyt
684 Followers

James Helling headed into his office building, avoiding the puddles that had formed from the rain showers of the previous evening. It was still overcast on this dreary Dallas Monday morning, and as he looked up into the heavens, he hoped it would continue to rain as the forecast predicted, they needed some relief from this blistering Texas summer.

The front door swung open for him as he neared the entrance, just like it had done every morning for over seven years.

"Good morning, Mr. Helling!" Daylon, the head of building security, beamed. They slapped hands and gave the male 'shoulder hug'

"The wife loves the gift, sir!" He extended his arm and showed off the gold Movado watch that adorned his wrist, the watch that James had bought for him.

"I'm glad, Daylon. You work so hard, I just figured that you deserved a token of our appreciation!" He gave him a big smile.

"You get a new car, Mr. Helling?"

"Yeah, 2009 Dodge Challenger SRT8, first one on the block. That sucker is a beast, 6.1 liter V8, 425 horses, 420 lb feet of torque, 6 speed, it is bad!"

"Did you put twenty two's on it?" Daylon craned his head towards the parking lot, trying to get a better view.

"Twenty fours!" James threw him the key. "Take it to lunch with you, you are such a car nut, I want your opinion."

Daylon's 60 year old face broke into a child-like grin.

"I sure will, Mr. Helling!"

James walked through the main lobby and into the elevator, making his way to the top floor of the high-rise. The doors shut and he examined himself in the mirrored finish of the elevator walls. James was THE man at a major mortgage lending company. He had been recruited hard by this company coming out of college, but decided to go with another company, but they never gave up. He made the move over here seven years ago and never regretted it. This place was an underperforming, sleeping giant when he came on board, and did he ruffle some feathers, he immediately fired anyone that wasn't on board with his program, and overnight earned the nickname of 'The Hammer', as in, 'When The Hammer comes down, look out!' The five story building consists entirely of the mortgage company, with the mailroom and whatnot on the bottom floor, and the senior execs on the top, and when he makes the rounds, even to this day, hearts skip a beat. The good thing, is that he values loyalty and effort, give him that, and he is your biggest fan. Although he is in a lofty position on the top floor, he knows the name of every employee in the building and will stop and chat with anyone, asking about their spouse or kids, even their dog. The company turned a profit in the second quarter of his leadership and never looked back, and he was VERY well compensated.

The reflection that faced him was a handsome one; James packed about 185 lbs on his six foot frame and kept in shape from four days a week of weightlifting and daily jogs. From his $300 haircut to his custom made suit, the platinum Rolex that adorned his wrist, to his Italian leather shoes, he screamed money. His mom and dad always complained that he wasn't married, heck, both his sister and brother had already provided them with grandkids, and if they weren't satisfied with that, his little sister could provide them some more rug rats. She was graduating this fall from college, James' alma mater, he would proudly tell anyone that would listen, and she was starting her internship any day now. She could get married; he just wasn't the marrying type. James preferred to play the field, and did so quite well.

Right before the door chime alerted him to his destination; he leaned forward and lightly brushed at the crow'?s feet around his eyes.

"Note to self." He said, under his breath, "Botox injections."

Adriana, James' secretary, greeted him with his daily planner, which was usually rife with appointments and business meetings. There was a huge gap this morning.

"What's with nine to eleven, Adriana?"

"Summer intern orientation, James, you know how you hate to miss that!" She smiled knowingly at him.

James exaggeratedly straightened his tie out.

"Ah! A new crop of fresh meat! How could I forget that?"

James winked at Adriana and went into his office, telling her to hold his calls for him so that he could prepare for the orientation. He had a major reputation of banging several of the young female interns that would come in every summer, and with his selection process, he always made sure that the incoming interns, of which there were usually between 15 and 20, were well over half women, and all gorgeous. He always had Adriana conduct the final interviews, making sure that the girls were top notch, and she always picked the top five girls to work on the top floor with James.

Adriana had been his personal secretary for four years and she was a stunner. Five foot four inch Latina with long, flowing black hair, pouty lips, a full C cup and a Vida Guerra ass. She was also bisexual. No big deal to James, she had great taste in women and it showed with the girls that she selected. James and Adriana played a serious flirting game with each other, with James trying everything that he could to get into her pants, usually to no avail. Eighteen months ago, Adriana succumbed to his advances after the company New Year party, and ever since, in both of their opinions, they had the perfect relationship, purely sex with no strings attached. James and Adriana usually hooked up about three times a month since then, although he really, really liked her, he could never tell her for fear that it would ruin their friendship.

"It is time, Master!" Adriana knocked at his door.

"Shall we?" James motioned to her to lead the way.

James and Adriana sat at a large table that was in the front of the employee meeting room on a lower floor.

"Please check in at the front and take a seat, everyone!"

The summer interns filed in, signing their names and finding seats in the auditorium.

"You have outdone yourself, my dear!" James leaned in to Adriana and whispered into her ear, commenting on the fact that most of the girls here could easily pose in Playboy.

"Well," Adriana grinned slyly, "They are not all for you!"

They both laughed and James cut himself short. A tall blonde lady walked in, high heels, sharp gray business suit with a skirt that came down just above the knee, showing off shapely calves. Underneath the jacket was a light purple shirt that was unbuttoned enough to show off some nice cleavage. Her curly flaxen hair flowed around her shoulders and she had on a pair of glasses that the hot librarian in your best wet dreams wore.

Adriana touched his thigh.

"Here is my favorite, she is hot!"

The stunning beauty strode with confidence into the room and toward the check-in table, stopping just short of it.

"What are you doing here?" James asked Donna, his sister.

"Do you two know each other?" Adriana inquired.

"Uh, she works out at my gym." James lied, knowing the strict company policy about relatives working within the company.

"I didn't realize that you were here, James!" Donna said as she nervously scribbled her name on the sign-up sheet before shaking Adriana's hand. "So, this is the one we were warned about?"

"The very one! Now please take a seat, we are about to get started."

James watched his sister find a place to sit, thinking that she had grown up quite beautiful, sexy even. He didn't see her that much, he chalked it up to the age difference, their parents had Donna when he was fourteen, and when he did, she usually had on a sweat suit or something akin to that. He shook his head, thinking that he had just been scoping out his little sister.

"Warned about?" He asked Adriana.

She just smiled and stood up.

"Good Morning, everyone!" She started. "You all should remember me, I am Adriana Fuentes, and I am the Intern Coordinator, and this is James Helling, the company CEO. In the next two hours, I will outline your duties for the next three months and James will brief you on what is expected, then I will give you your duties and those groups will go to their respective departments for further instruction. Shall we begin?"

The meeting was a whirlwind for James as he found his eyes irresistibly drawn towards Donna time and again. He couldn't help but look her over as her legs were crossed very demurely and lady-like, her foot bouncing slightly every now and again.

Adriana placed Donna and two other stunners in the group that worked for him, much to his chagrin.

Walking out of the office at the end of the day, James snatched the chance and grabbed Donna by the elbow, pulling her to the side. Anyone that saw this just figured that he was lining up his next victim.

"What are you doing?" He spat, feeling the veins in his forehead popping out from the anger that rose from within him. "You know about the nepotism clause with this company, do you want to get me fired?"

Donna looked over her shoulder nervously.

"Hell, no! This is the hottest internship in the land for my field, I am sorry, bro, this is about me and not you!" Donna stated, her eyebrow darting up like it always did when she was being defiant.

James smiled and put his hands on her shoulders.

"We need to be careful then. No slip-ups whatsoever."

Donna's stance eased.

"I took all of the precautions. Mom and Dad's address isn't listed on your emergency contacts, our last name isn't rare, y'know, besides, I want to learn from the best, and, now I can!" She grinned from ear to ear. "You have to play your part also, big bro."

"What do you mean?"

"I have heard stories about you and the summer interns, so if you don't treat me the same way, red flags will go up!"

"DONNA!" James protested, looking from side to side to see if anyone was looking at them. He grabbed her by the elbow and gently led her off towards the file room. "I am NOT going to sleep with you!"

"Ah! What's wrong bro? I give GREAT head!" Donna pursed her lips up at him and rocked back and forth on her long, lovely gams.

"DONNA!"

"Jeezus, James! Get over it! I mean that you have to at least treat me like you normally would, y'know, hit on me and shit." Donna stepped away from him briefly and placed her hands on her hips, thrusting her chest out towards him. "It won't be that hard, will it, Mr. Helling?"

James smiled and shook his head slowly back and forth.

"You certainly have grown up, little sis, in a, uh, couple of areas for sure!"

Donna and James laughed together and made their pact together, it was ninety days for the internship, and he vowed to make her deadly in the business, after all, what is family for?

*************************************************

Donna walked in to James's office and placed a stack of manila folders in his inbox, things that needed a signature.

"Whatcha doin', bro?" She moved around behind him as he leaned back in his swivel chair, placing his glasses on the desk. Donna began massaging his shoulders.

"Oh, just some busy work. I am tired as Hell. You?"

"I was just thinking that this summer has flown by, there is only a week left in this internship, and to think, big brother, you didn't get into my pants!" Donna laughed.

"It's not like I didn't try!" James added, jokingly. "Seriously, Donna, You have been wonderful this summer, I am petitioning the board to waive their family rule. I want you here after you graduate!"

"I am stunned, bro!" Donna sat on the corner of his desk, crossing her legs at the ankles and causing her skirt to ride a little higher on her toned, tanned thigh. "But, I am worried about you. You aren't yourself, what is wrong?"

James rolled his head about, stretching his neck. He caught Donna's pretty feet in his line of sight and casually observed her long, slim toes that were pedicured to perfection as they led to her shapely calves and muscular, yet ultra feminine thighs. He forcefully pulled his eyes away as he could feel the onset of an erection forming in his trousers. Donna was a very, very pretty woman, and they had worked closely together over the last two and a half months, James would be a liar if he told you that he didn't think about her late at night, in compromising situations. Alas, there was more.

"James?"

A gentle finger under his chin pulled his eyes up towards hers, but not before he caught a nice downblouse shot of her full, round breasts.

He stirred in his seat, more so to downplay his rapidly swelling erection than anything else.

"Uh...don't think that I am stupid, O.K?"

Upon her nod of approval, he continued.

"Adriana hasn't been herself lately. There. It's out!" James could feel himself redden.

"Bro? You have fallen for Adriana?"

"SHHHHHH!" James looked out of his office door towards Adriana's. She wasn't there. "I don't know about all of that, well...sorta...kinda...yeah." He added in a whisper.

"Oh James!" Donna kissed his forehead. "That is wonderful!"

"How is it wonderful?" He rose up in his chair, face beet red. "She lives with a woman, she's a lesbian, and I can't get her out of my mind!"

Donna soothed him, "Lesbian, no. Confused, moreso, bisexual, definitely. FYI, big bro, she and the girlfriend are no more. I think that she is enamored with someone else!"

"Great. Who?"

"Someone that has been, shall we say, very close to her for a while." Donna looked at James knowingly.

"You are aware of...us?" James looked at his little sister quizzically. "Since when?"

"I told you that she and the "Girlfriend" broke up. She needed a place to stay; I have a big apartment, thanks to Daddy's money, which is no longer lonely." Donna leaned back on to the desk. It was hard for James not to notice how incredibly large her chest looked as her boobs strained against the fabric of her cotton polo. "She and I have downed much Tequila over the last few weeks, and shared many, many stories. If what she says is true, big bro, and I emphasize 'Big', I would be very impressed."

James stood and turned his back to her, looking out of the top floor window onto the lights of Dallas as it stretched out before him.

"That is not important, Donna." He questioned, "Why not so much as a hint at all from her?"

"She has seen you bang countless numbers of ditzy interns in her time here." Donna almost scolded him. "Why should she let herself fall for you, just to see you throw her away like the others?"

"I would never..."

Donna cut him off abruptly.

"Have you told her that?"

"Of course not!"

"She hated me at first because she thought that I was fucking you." Donna smiled.

"You didn't tell her, did you?"

"Hell no!" Donna stated with aplomb. "I just told her that you were eyeballing me, that's all. I told her that I would fuck you if you made the move!"

"No time for jokes, Donna."

"No joke, James."

James and Donna stopped and looked at each other, their eyes meeting, tension building.

"Did I...interrupt something?" A voice broke through the silence like a knife.

"Adriana!" James nearly shouted, "I hadn't seen you all day, where have you been?"

"The third floor, boss, remember, I had to go over the intern files?" She stated, a questioning look on her face.

"Ade, I was just stopping in to invite James to our house warming party tonight, and he was telling me that he would be there for sure!" Donna waved bye to the two of them, "I have to clear up some things before I enjoy my Friday, so I will leave. James, nine-ish, remember?"

"Uh, sure, Donna, sure."

Adriana and James stood for what seemed like an eternity in an awkward silence.

"You like her don't you?" Adriana asked him.

"No, Ade, not in that way." James assured her, "You hit the jack-pot this year with the interns, though, I will tell you. I just haven't had the desire to bed any of them."

"Old age creeping up on you, boss?" Adriana kidded him.

"Maybe I want to finally settle down."

Adriana could feel his deep blue eyes piercing into hers, her body becoming warm, little bolts of electricity zapped at her up and down her spine.

James took her silence as a rebuff and quickly changed the subject.

"I heard about you and Cassandra breaking up. I'm sorry to hear that. You could have stayed with me, you didn't have to stay with my si-, my, uh, intern." James turned his blushing face away from her, hoping that he didn't blow it. He didn't.

"I didn't want to burden you, James. I'll see you tonight, right?" She asked, almost in a pleading tone.

"You bet, my dear, you bet!" James smiled as she walked from the room.

*************************************************

James rang the doorbell promptly at 9:27 and waited for the door to open, nervous as, well as Grandpa used to say, "A long tailed cat in a room full of rocking chairs!"

The door was opened by a complete stranger. A good looking boy, probably 22, 23 years old, his sister's age.

"What's up, dude, c'mon in."

He led me through the loft apartment that my sister thinks that our parents paid for, but I have the deed at my house to assuage that argument. She had done an awesome job decorating for what she had to work with. James chose this place because of the industrial feel of it, and she decorated it with some nice, modern furniture and artwork as well. Large, open floor with a small bath and bedroom downstairs, a large master and master bath upstairs that looked out on the lay of the house. Exposed overhead pipes and the mortared walls added to the feel of it. His favorite was the wall to wall windows that stretched the length of the apartment on the East side that allowed a generous view of the Dallas night life.

There had to have been thirty people inside, and who knows how many out on the balcony, the smoking section. It looked like a fair mixture that favored the women slightly, there was the artsy looking type with the disheveled look, the jocks with the upturned collars on their Polo shirts, the college frat boys and the sorority sisters. He was definitely the oldest person there, which normally didn't affect him at all; however, his nerves were really acting up.

He suddenly saw the two of them over by the island in the kitchen. They were getting some rapt attention, and James could see why, Donna was wearing a pair of jeans that were slung so low that the top of the jeans were below her hip bones. Her flat stomach was accentuated with a shiny diamond belly chain that dangled from her navel, her massive breasts were sheathed, barely, by a cream colored tube top that left no doubt that she was braless.

Adriana was breathtaking in her own right. Her back was to James, and he could recognize that bare back anywhere, he had, however, sprayed enough nut-butter on that back to wax a gym floor with. Her luscious, round ass was sheathed via a pair of light gray linen pants that fit her hips and buttocks like a second skin, and flared out towards her feet, which were clad in a pair of slinky four inch heels, her sexy toes capped in red. She had done her hair perfectly; her natural black color was tinted with red and blonde, and curled around her exquisite neck as it cascaded down her bare back. The matching gray top that she had on had a clear plastic strap that circled her back and the blouse itself tied at the back of her neck before it plunged down her front, revealing amazing cleavage and bunching up right below her navel. She looked amazing.

Donna looked at him as he approached, breaking into a smile and nudging Adriana.

"Hey, Handsome!" Donna squealed in glee, placing a kiss firmly on his lips, "I am glad that you showed up in time!"

"Yeah, well, y'know!" James sheepishly said as he threw an arm around Adriana, "You two look amazing!"

"You like?" Donna asked him, throwing her shoulders back and her chest out in a mock pose.

"Nice headlights, kiddo!" James sniggered.

gymmyt
gymmyt
684 Followers
12