Debbie the Intern

Story Info
Debbie wants to make daddy happy.
5.4k words
4.46
44.6k
52
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

In many ways, Stephanie Renner was exactly who one would expect to be the Executive Assistant to the Senior Partner of the Most Prestigious Law Firm in the city. She was smart, efficient, well educated, attractive, impeccably dressed, pleasant, driven, and forceful.

Stephanie was also very young for such a job, only 29. She had received her BA at 19, decided she wanted to be close to money and power and set her sights on her present job. She worked her way up the ranks at various firms. Each firm and each job was a carefully planned stepping stone.

Stephanie's intelligence and talent had made her a valued employee. But Stephanie had advanced because she knew how to fulfill her boss's deepest desires. She was ruthless about it - bribing, blackmailing, and seducing others to ensure those desires were satisfied.

Stephanie blackmailed a hedge fund manager so her boss could buy a rare antique auto. She seduced the son of a famous CEO to obtain a Picasso another boss wanted. Stephanie secretly paid Czech porn stars with company money to 'accompany' her last boss on business trips.

That was how she became the Executive Assistant to the Senior Partner of the Most Prestigious Law Firm. Fulfilling his desires was a key part of her job description, though a part that was never written down.

Today, Stephanie was interviewing candidates for a new internship. Normally, internships were handled by Human Resources. But this internship was for the Senior Partner and he was very particular.

The written requirements for the internship had been carefully crafted to find someone like the girl sitting on the other side of Stephanie's desk.

Her name was Debbie with an 'ie'. She had come from a small town in the Mid West to the big city looking for adventure and opportunity. She probably dotted the ' i ' in her name with a heart.

Debbie's job experience was minimal: babysitting, retail, a summer job at her uncle's car dealership. But all the intern candidates had minimal job experience.

The interview showed the girl to be exactly what was expected. Naive, optimistic, eager. Willing to work late and do anything. But most of the intern candidates were naive, optimistic, and eager.

Those were the written requirements but they weren't what the Senior Partner really cared about.

Stephanie's job was to see if the girl met the unwritten requirements. The crucial requirements.

Debbie was wearing clothes that came from some discount chain, a polyester/cotton blend and definitely last year's style. The young girl's makeup was tasteful though the application had been amateurish.

Stephanie mentally shrugged. Clothes and makeup could be fixed. "At least it's better than the last girl. She looked like a cross between a streetwalker and a clown."

Debbie had just turned 19 and was cute in a 'girl next door' way. She had long thick red hair that hung almost to her waist. Her eyes were green. She was short, only about 5' 3". The girl was flat chested. Stephanie's practiced eye estimated she was a 34A.

Debbie had been a gymnast in high school. Her body was slender, athletic, and flexible. She moved with an unconscious gracefulness.

Cute, slender, and agile were among the Senior Partner's unwritten requirements. Stephanie had some requirements of her own but that would come later.

Stephanie had already interviewed dozens just like her. But this one was special. Stephanie couldn't really put her finger on it but she hired Debbie.

One of the things not on Debbie's resume, and the reason she was hired, was The Voice. It had arrived when Debbie hit puberty.

The Voice was a certain way of speaking: soft, warm, a bit deeper than her normal tone, slow, with a hint of Southern drawl and Irish lilt, Even Debbie liked The Voice. It evoked lullabies and summer breezes, lover's holding hands, days at the beach, dreams fulfilled.

When Debbie used The Voice, people wanted to agree with her. It made people feel special when they agreed with The Voice. Each person felt it differently. Some felt happy, some felt safe, some felt loved. But they all felt very, very good.

It wasn't hypnosis. Debbie couldn't make people dance like chickens or anything like that. People could, and did, ignore The Voice but only if they strongly wanted something else.

When a group couldn't decide on a restaurant, Debbie would use The Voice and suddenly everyone would want to go to her favorite place. She would use The Voice on a date and the boy would want to see Debbie's favorite movie for the fifth time.

Or she could use The Voice during a job interview and the person would want to hire her. Debbie had used The Voice on Stephanie.

"I really hope you'll hire me," Debbie had repeated several times.

Each time, Stephanie felt how pleased her boss would be with her for hiring Debbie. Each time, Stephanie felt the pleasures the girl would bring to her directly.

Debbie began work the next Monday. She was the Executive Assistant's intern, working directly for Stephanie. The first couple of days consisted of filling out employment papers, training, tours of the firm, settling in. The rest of the week was routine. Delivering papers throughout the building, doing minor tasks, getting coffee and lunch for Stephanie and the Senior Partner.

As expected, Debbie was eager to please. She stayed late twice. Stephanie had asked her to stay late to finish some routine filing that could have waited for the next day. It was part of the process. Making sure the intern really would do whatever she was told.

Monday of the second week, Stephanie took Debbie aside. "Your wardrobe reflects poorly on the company. Not to be mean but it is shabby. Look around at what others are wearing. That is what you should be wearing."

Debbie held her breath. She was going to be fired. She couldn't afford expensive clothes like the others. She had read enough issues of Vogue to know Stephanie's pale yellow suit cost at least a thousand dollars.

"The Senior Partner likes to mentor his young interns. Give them a good start in their careers. This afternoon, you and I will go out shopping and buy you some appropriate clothes."

"I can't possibly afford that. My check barely covers my rent and such."

"Don't worry dear. The firm is paying. To get you off to a good start." Stephanie's eyes roved over Debbie's body. "There will be an appropriate time to express your appreciation."

That afternoon, Stephanie took Debbie to a boutique clothing store. The two sales women knew Stephanie. The women looked at Debbie like sharks look at a seal. Dinner, or at least fat commissions.

Debbie was taken to a screened-off area.

"Take off your clothes. All of them," Stephanie ordered brusquely and then stepped away.

Debbie hesitated. "I guess this is how they do things at these fancy boutique stores," she thought.

Debbie removed her clothes. The sales ladies carefully folded the items and set them aside. She was measured six ways to Sunday. Measured in a way meant to test the intern.

One sales lady would take a measurement. The other sales lady would lightly fondle Debbie's naked body, caressing her ass, tits, or pussy. Then the two women would switch places. Sometimes the same measurement was taken two or three times.

Stephanie listened closely. This was part of the process too. To see how far the intern would go. Since the sales ladies didn't work for the law firm and Stephanie wasn't present behind the screen, there was plausible deniability when the touching began.

At first, Debbie tried to cover up and avoid the fondling. By the third measurement, she had relaxed and was letting herself enjoy it. By the seventh measurement, she was encouraging the sales ladies.

"This is crazy," thought Debbie, "but I might as well enjoy it. Besides I need the job."

Stephanie smiled. So far, so good. She snapped her fingers and stepped back behind the screen. The two sales women scattered to collect an assortment of new blouses, skirts, and jackets.

Debbie stood with her back to her boss. She was suddenly embarrassed about what had just happened.

Stephanie always liked this part. It was a high stakes game for the firm, the intern, and the Executive Assistant. Had Stephanie picked the right candidate or not? Now was when Stephanie would find out if her own requirements would be met.

This was the final test for the intern. If she failed, there would be a quick payment, a good reference, and a nondisclosure agreement. Stephanie would make all evidence of the hiring disappear. Very Important Law Firms did not like sexual harassment suits.

Stephanie moved close behind the naked girl. She put her hands on Debbie's waist and let them slip down to her hips. She cradled Debbie's bare butt cheeks and pulled them apart.

"Do you mind me doing this?"

"They sure don't do that back home. I kind of like it," Debbie thought but she didn't say anything in response to the question.

Stephanie ran a finger down the ass crack and pressed against the girl's ass hole. Her finger pushed inside. Debbie made a noise that clearly wasn't an objection and leaned forward a little.

"No one has ever played with my ass hole before. It feels funny but nice," she breathed. "My boyfriend played with my tits a lot but never my ass."

Stephanie thought, "Damn it! I forgot to ask about a boyfriend before." She asked now.

"We broke up a couple months ago. He didn't want me moving here. It wasn't that serious anyway."

Stephanie was now fingering Debbie's pussy. Debbie was quietly moaning and opened her legs to allow better access.

"My best friend and I had sex once," Debbie volunteered. "We were terrified of getting caught but once we got into it, it was really nice."

The girl pulled away from Stephanie and turned around to face her.

"Is this personal? Or part of the job?" asked Debbie.

She didn't wait for an answer. Debbie began unbuttoning her boss' blouse. She unhooked the bra and exposed the older woman's tits. She took one breast in her mouth and massaged the other with her hand.

Stephanie had definitely picked the right candidate for the job.

Stephanie let the girl suck on her tits for a while. The girl may have come from a small town but she had a talented tongue.

Debbie guessed what was going through the older woman's mind. She smiled to herself. She hadn't felt it necessary to say she had grown up in a well to do Chicago suburb. She and her mother had moved to the small town only a couple months before.

"Sometimes it's better to let them think you're a country mouse," Debbie mused.

Stephanie snapped her fingers and the two sales women appeared carrying an assortment of clothes. Stephanie didn't appear concerned that Debbie was still sucking her tits.

"The gray outfit, the light blue, and the dark green. Two of each," the Executive Assistant said, selecting the purchases. She turned away from Debbie and fixed her bra and blouse.

Debbie assumed they were finished, so what happened next surprised her. The two women brought a camera from the corner and set it up in front of an old fashioned couch with curved wooden arms.

They proceeded to pose and photograph Debbie in a variety of erotic positions on the couch as they dressed her in the new gray outfit. It was like a reverse striptease. Some of the poses were solo, some were with one of the sales women. Debbie's tits and pussy were touched a lot.

After filming was done, the memory card with the photos went in Stephanie's purse.

"For my personal album," she said nonchalantly.

"What about bra and panties?" Debbie was fully dressed except for that.

"You won't be wearing any underwear to work from now on. Is that understood?" That was one reason Stephanie preferred small breasted girls for interns. It was easier to hide the fact they were braless.

Debbie nodded. The cool air felt good on her ass. Almost as good as Stephanie's hand had felt.

They were walking back to the office as Stephanie explained that Debbie's job would change.

"You will have some new duties at the office. Some for me and some for the Senior Partner. Do you understand?"

"Involving my assets?" asked Debbie coyly. Stephanie smiled and said nothing.

Back at work, Stephanie sat at her desk, chair pushed back.

"Get under my desk. Lick me until I tell you to stop." Now her own pleasure would begin.

This was the part Stephanie liked the best. Having control over someone. Literally making the person kneel in front of her. Making sure they knew their sole purpose was to pleasure her.

Debbie scooted under the desk. She realized all three sides were solid and went to the floor. Nobody could see her.

Stephanie rolled her chair forward, slid her skirt up, and resumed her work.

Debbie went to work also. Stephanie shaved her slit but left a nice amount of hair above it. Debbie played with the hair while licking the outside of the lips. She pushed her tongue inside and tasted the dampness.

Debbie was enjoying herself. Stephanie tasted good and it was fun trying to get her wetter and wetter. It took almost 20 minutes but Debbie got Stephanie to cum. There was no dramatic orgasm, just a pause in the work and some sticky white fluid flowed out. Debbie licked it up. She thought she was done.

"Don't stop," Stephanie commanded.

Forty-five minutes later, Debbie wasn't enjoying herself. Her legs were cramping and her mouth was dry.

"I need to pee," she called out from under the desk. Stephanie rolled her chair back and let Debbie stand up.

"Pee in that corner. Facing me." There was a large silver urn in the corner. It looked like a piece of art. But it was designed to be a voyeur's urinal.

Debbie looked at her boss quizzical and uncertain.

"I like to watch women pee. I don't like watersports, just watching," Stephanie had found a brief explanation cut short the questions. What Stephanie really liked was that the person was helpless while they peed.

Stephanie never did anything to the person peeing. Just the idea that she could do something and the person would be helpless to stop her is what aroused her. It aroused her a lot.

"There's a remote control on the table. You can lock the door with it if you want. There's also a bidet built in to clean yourself. I like watching that part too."

The top edges of the urn were shaped to accommodate a person's legs. The back edge provided a tiny seat. The front edge dipped down to offer a clear view.

Inside were two cameras, one for stills and one for video. At night, Stephanie would lie in bed, watching the videos, masturbating. That was the extent of her rather pathetic sex life.

Stephanie watched closely as Debbie peed. It was a strong stream of urine, the kind Stephanie liked best.

"You may go home now. Get a good night's sleep. Don't pee until you get to work."

The next morning Debbie arrived a little early. She really had to pee. Stephanie nodded at the urn in the corner. Debbie stood this time as her stream flowed out.

"Why don't you play with yourself while I pee?" Debbie suggested using The Voice.

Stephanie pulled up her skirt and began fingering herself. She had never done that before. She really, really enjoyed it.

When Debbie was done cleaning herself, she had another suggestion.

"Why don't I come over there and finish you off?" Again using The Voice.

Stephanie motioned the intern over. Debbie knelt on the floor and used her tongue to make her boss cum. There was no hiding under the desk this time.

When Stephanie came, it left the carpet wet. The Executive Assistant was certain she had never had a better orgasm.

It took Stephanie several minutes to recover. She finally straightened her clothes.

"The Senior Partner wants to talk to you. I'll take you in."

The two went to the corner office next door. Stephanie didn't knock. The office was huge, with a desk, couch, coffee table, and several chairs.

The Senior Partner sat at his desk. He was in his fifties, white haired, and fit. His suit was custom tailored and made Stephanie's thousand dollar outfit look cheap.

The Senior Partner didn't speak. He looked at Debbie for a few moments then nodded at Stephanie. The older woman stood behind the girl and slowly undressed her.

"Very nice. You always know what I want."

To Debbie, he said, "Are you a virgin?" She shook her head. She didn't have much experience but she wasn't a virgin.

"Good. Virgins are always such a pain."

He moved his finger in a circle. Debbie turned a slow 360 letting him see every side.

"Are you on birth control?"

"I have a diaphragm," she replied.

"Take it out. Go into the bathroom there. There's a shower. Rinse out your pussy thoroughly to get rid of the spermicide. At my age, I don't like to waste sperm."

As Debbie walked to the bathroom, she realized the Senior Partner was planning to get her pregnant. She didn't know what to do. She thought about it the whole time she was rinsing out her pussy.

The Senior Partner said "As you probably guessed, you and I are going to have sexual relations. We are going to do some other things as well. The room next to the bathroom is soundproof. You will be able to scream as much as you like."

Debbie suddenly got very scared. The man smiled.

"There may be some bondage, nipple clips, that sort of thing. Nothing terrible. Mostly they will be screams of pleasure, not pain. Have you ever had a vibrator pressed against your pussy for hours at a time? The pleasure gets quite intense."

"You are no longer to use any type of birth control. I enjoy the possibility that you might get pregnant. But this is not a breeding farm. It is perfectly alright if you don't get pregnant."

He drummed his fingers on the desk.

"I will eventually get tired of you. Sooner rather than later. At that point, you will have several options. You can 'work' for one of the other partners. They aren't necessarily as nice as I am. Or we can arrange for a job at a firm in another city. I don't like to bump into my former interns accidentally"

The Senior Partner looked bored. He had said this many times before.

"If you get pregnant, you will be dismissed from this firm immediately. We will arrange a good job at another company and provide a generous stipend. If you are smart and talented, you can rise rapidly and be quite a success. Take Stephanie here. She started as an intern. How many children did you have Stephanie?"

For the first time, Stephanie seemed a little flustered.

"Two." She looked at Debbie. "Twins. I found a nice family that couldn't have children. They adopted both of them. I'm not interested in children myself but they were useful as a means to an end. They got me my first Executive Assistant job."

Debbie shivered at the callousness of it. If she had children, she would want to keep them. It was time to explain her idea. She walked to the big desk, planted her hands, and leaned forward.

She spoke using The Voice. It was mesmerizing.

"Surely you aren't the only one who likes the possibility that a woman could get pregnant. Or who is interested in having 'relations' with a woman that is already pregnant. What if that was my job? Consider it a marketing tool for clients. A recruiting tool for hotshot new lawyers. When you need a little extra competitive edge."

She glanced behind her. "Stephanie can vouch for my ability to handle the women. Can't you Stephanie?"

The Executive Assistant rubbed her still warm her pussy and nodded.

"She made me cum with her tongue just a few minutes ago. It was so good."

Debbie resumed her sales pitch.

"I'd keep myself fit and attractive. I'd raise the kids, using your generous stipend, and stay out of the way until needed. You and the others pick your child's name, get updates as they grow up, shape their careers. All the benefits of fatherhood without any of the messy real-life details."

12