Lisa and Her Intern

Ever since her teens, Lisa was disciplined and driven. She attended a prestigious west coast university on a tennis scholarship. She maintained excellent grades and was consistently making the Dean's List when she dropped out to pursue tennis professionally.

Her professional tennis career started with great promise. She was soon consistently playing amongst the world's best. At the age of 21, she won two major tennis tournaments. With her model-like beauty and her tall athletic figure, She was the darling of the media.

Unfortunately, as is common with elite athletes, her career was interrupted by injuries. After being sidelined for almost a year, she retired from professional tennis.

She went back to university and completed her studies. She graduated with a degree in business and economics.

While in a school, her beauty and fame caught the eye of a local modeling agency. She was convinced to try out modeling. Her modeling career started out part-time while she was in school.

After graduation, she decided to pursue modeling professionally. She had average to small size breasts and at the advice of the modeling agency she had breast implants. She landed a modeling contract for a major athletic apparel company. She mostly did catalog shoots, with the occasional in-person promotions.

Her modeling career was successful, but she realized, now nearly thirty, she would soon be considered too old.

She moved to Los Angeles and started her own very successful business. Her business was an agency that provided career marketing and brand management for athletes. She was a bit of a pioneer, because not only was this an emerging field, but she was a woman in a male-dominated environment.

Having always prioritized her career, she now was a successful 54 year old woman who had never married. Throughout her adult life, she discovered that most men were intimidated by her success. She moved from one relationship to another. Currently she was dating a handsome 58 year old divorced executive at a Fortune 500 company.

Even after she faded from the public eye years ago, she was still viewed as a celebrity in her small midwestern home town. Feeling the desire to give back to her roots, Lisa started an internship program at her former high school.

The program involved offering airfare, housing, and a small salary for a college summer internship. Her former high school took responsibility for the selection process. Aside from having had to be a graduate from the high school, the applicants had to meet the usual requirements such as being actively enrolled in college, maintain a certain GPA, have a clean criminal history, etc.

Lisa read the email announcing Andrew Holt as the inaugural recipient of the internship with an unexpected pang of disappointed. She realized she just assumed the intern would be female. Her desire was to help young women achieve success in business.

The second Lisa laid eyes on Andrew Holt, she was overcome with a different desire.

"Hi Ms Flowers, I'm Andy." He held out his hand. Lisa stood for a second looking him over.

He was extremely handsome with chiseled features. He had perfect fair skin with dark features. He had big dark eyes with long lashes. His thick black hair was in a tussled mop with bangs falling over his forehead.

From his application, she knew he was 19 years old and just finished his freshman year at his state college. But he looked younger. Also, from his application she knew he didn't play sports in college. But his physique was clearly the result of substantial time at the gym.

"Well hello, Andy. It's a pleasure to meet you." She said stepping closer to shake his hand. At 5'8", she was taller than the 5'6" intern, and with her heels, she seemed to tower over him.

He was smiling and his eyes were sparkling with nervous excitement. He was wearing a blue button down shirt that could not hide his broad chest and muscular arms. The shirt was tucked into a pair of slim khaki pants.

"Wow, it's an honor to meet you Ms Flowers. I mean this is so cool. This is my dream job. Thank you." He said gushing with excitement. "Is that who I think it is out there?" As Andy passed through the sleek busy open office he noticed a prominent professional athlete talking to one of the agency staff members.

Lisa always dressed appropriately for the office, but never hid her athletic figure nor her ample breasts. She wore a silky white blouse with enough buttons undone to reveal her deep cleavage. Her skinny black pants accentuated her slim waist and hugged her ass. Her hair was light brown with blonde highlights. She wore her hair in a bouncy layered bob cut with bangs.

"Well, Andy," she said as she put her hands on his shoulders then slid them down his arms gently squeezing his biceps. She paused, blatantly admiring his chest and then slowly letting her eyes drift down his torso. Her eyes lingered on his crotch before she nodded approvingly. "I think you are going to be a great intern. I mean as long as you work hard and follow directions."

"Oh yes! I mean, you don't have to worry about that. I will work super hard and do everything you need me to." He tried to sound professional, but he could not hide his childlike excitement.

"Well let me give you an introductory tour, before I hand you off to Stephanie to get you settled in." She slid her hand down his back casually as she guided him out of her office. She kept her hand on the small of his back the whole time as they wandered through the busy office.

Throughout his first week, Andy was allowed to sit in on meetings, given minor tasks, and shadowed various employees. He tried to act professional, but his eagerness could not be suppressed. He always wore a button down shirt, khaki pants and a huge smile the whole day and every day.

Lisa made time from her busy schedule to check in with him daily. She frequently went to his cubicle and leaned over him from behind pressing her chest into his cheek as she looked over his shoulder at his laptop.

She always kept her hand on his back if they walked together. She casually caressed his shoulders or arms during any conversation.

Andy found the physical contact a bit awkward. He did not say anything because he really loved his internship and he desperately wanted a full time job there.

Although she was really quite attractive with a great figure, he did not view her as anything other than his old woman boss. He convinced himself that this is how sophisticated adults behave.

"Andy" Lisa said one day in her office "One of the tips for being successful is to put in extra effort with the clients. You don't need to do anything you don't want to, of course. But any opportunity to do something extra goes a long way. The same goes for your bosses. You may be asked to do things not specifically related to work, but if you do it, it helps you out in the long run."

"Oh yes, Ms Flowers, I'm sure there is nothing I can't do to help the clients, or the boss... I mean you." He said with his usual enthusiasm. "Just tell me how to help. I really, really, really, want to work here after college."

"Well..." she said stroking his biceps and staring at his chest. "If you do a good job as an intern, I bet there may be a place for you here at the agency. So far, you seem to be exactly what I..." She gave a forced laugh. "I mean, what the agency needs."

That Friday, Andy received a call from Lisa. "Hi Andy. Listen, I'm off site with a client and I have another off site this evening. There is a portfolio of some glossies on my desk. I was hoping to look them over before Monday. I know it's the weekend, but if it's not too much bother, can you drop them off at my house tomorrow? It would save me a trip back to the office."

"Of course! No problem, happy to help any way I can." He responded eagerly.

The next morning, Andy rang the bell. He was dressed as if he was going to the office with his usual blue button down shirt and khaki pants.

Lisa opened the door wearing a white collared short sleeve tennis dress. The v-neck of the dress revealed her cleavage while the stretchy fabric clung closely to her breasts. The dress hugged her thin waist before flaring out stopping just below her ass. Her legs and feet were bare.

"Here you go Ms Flowers." Andy smiled triumphantly as he held out the portfolio. "I brought it, just like you asked."

She took the portfolio. "Why thank you Andy. Say, if you have a minute, I'd love to chat with you, you know, just see how things are going."

"Oh sure, I have plenty of time."

"Great, come on in, but if you don't mind, this is a shoes-off house." He quickly kicked off his shoes. Lisa followed him into the living room admiring his tight ass as he walked. Once in the living room, she directed him to sit on the couch.

She tossed the portfolio onto the coffee table and sat very close to him on his right side. She crossed her right leg over her left so it rubbed his right leg as she swung her leg casually.

She twisted her torso so she was looking at him inches from his face. Her left arm was bent with her elbow on the back of the sofa, her hand cradling her face. Her right hand slowly traced the outline of her v-neck as she spoke.

"You doing OK? You like it at the agency?"

"Oh yes. I love it. I mean, I can't believe I'm here. I really really really want to work here." He said earnestly.

"Well you're doing a great job. Remember how I told you to go the extra mile with clients, and your bosses?"

"Oh yes, I'm always saying yes to anything asked of me."

"Well, the next step is to do the extra things without being asked. But it's more of an art than you think. If you're too blatant, the clients will think you are just desperate and your bosses will think you're a brown-noser."

He frowned as he pondered her advice. "But what's the trick? I want to do it right."

"Well, you have to assess every situation. You have to examine your position and see how you can please the clients from there. If you do it correctly, the clients will feel special, like VIPs. And your bosses will think of you as a go-getter, a real stand-out."

"Oh, yeah, I get it. I really want to learn that." He said determinedly.

"Well, there are a couple of exercises that help. I was going to show you on Monday, but if you want, we can do them now."

"Yeah, I would love to do them now. If that's OK with you, I mean, please." He almost begged.

"Ok then, let's see... oh yes, here's a good one. First you stand up in front of me, facing me."

He sprang up and stood facing her. Lisa straightened her self on the couch still seated. "Ok now you kneel." Andy immediately dropped to his knees.

Lisa slowly reclined back, spread her legs, and lifted the hem of her dress. Andy's eyes got big and his mouth dropped open slightly as he stared at her shaved pussy.

"Ok, from this position, how do you think you can please me?" She asked.

"Umm, what about... don't you have a boyfriend?" He stammered nervously.

"Andy, this isn't about anybody else. It's about you... you taking the initiative. But if you don't want to, that's fine. You just have to ask yourself how important is this job to you."

He swallowed. Then he slowly leaned in and kissed her pussy. "Oh, good, good!" She said encouragingly. "Way to take the initiative." He continued to kiss and lick her cunt more energetically.

He worked on her pussy with his youthful energy. "Oh yes.. yes.. this is very pleasing to me. Good job, Andy..." She said starting to breath harder.

Andy was not very experienced in cunnilingus, but by the way he felt her rock and tremble he knew he was doing something right.

"Oh Andy, lick my clit. Lick a little higher, high... yes right there. Suck my clit... harder... yes, even harder" She directed the show and he did as told. "Oh yes, you are my go-getter!" She was panting now.

Andy continued licking and sucking her. Her breaths became faster. Her body rocked. She moaned softly.

Suddenly her body went stiff, her pelvis arched up into his face. She inhaled sharply and held her breath. Her whole body quivered as she orgasmed. Then she exhaled loudly and went limp.

Andy looked up, slightly dumbfounded. Lisa slowly caught her breath. After a moment, she said encouragingly "That was good. Let's try another one shall we? This time you stand up."

Still in shock, he stood up. "OK, now take off your shirt." He undid his buttons and took off his shirt. She could not control the soft gasp that escaped her lips at the sight of his naked torso.

The sight of his smooth large pecs and his flat hard abdomen made her pussy tingle. She admired every curve and bulge of his muscular shoulders and arms. She stood up and slowly ran her fingers across his chest. She traced some of his abdominal muscles slowly.

"Good, now take off your pants." She tried to sound calm, but it came out in almost a hoarse whisper.

Andy undid his pants button and let them slip to the floor. He then pushed his boxer briefs down. He stepped out of his clothes and kicked them aside. He stood before her fully nude. She looked down at his crotch. She smiled as shook her head in feigned disapproval at his limp cock.

"OK, now I need you to get hard. I could do that for you with my mouth, but for your first time I think you should do it all on your own." With a fake tone of pity she added "But I can help you a little."

She slowly stretched the v-neck of her dress over one shoulder and slipped her arm out. She repeated the maneuver with the other side. She pushed the top of her dress down so it bunched up under her now exposed breasts.

Andy's cock came to life almost immediately at the sight of her tits. It only took him a couple of strokes before his cock was fully hard. Lisa raised a hand to her mouth and spit into her palm. She reached down and lubricated his rigid shaft with her saliva.

She turned around and climbed onto the couch. She knelt facing away from him, her forearms resting on the back of the couch, her back arched and her ass in the air. She hiked up her dress again exposing her ass and moist pussy. She turned her head to look back at him.

"Ok, from this position, what can you do that would please me?"

Andy stepped forward. He fumbled a little before awkwardly plunging his hard cock in her pussy. "Oh, yes, Andy... Great idea!" She said with genuine enthusiasm. "I like what you're thinking."

He instinctively started fucking her. "Oh yes... yes" She was starting to lose herself in pleasure. She was breathing harder with each thrust of the teenage cock.

"Oh... oh, grab my tits." she instructed between hard breaths.

Without hesitation he reached around and fondled her jiggling tits. "Faster, Andy." she said as she reached down and rubbed her clit. She started bucking in rhythm with his efforts.

She was pushed forward into the couch with each forceful thrust. Her head was being whipped up and down. His hard cock was ramming her wet pussy in a steady fast pace.

"Yes, yes, yes" She repeated getting louder with each breath. He body quivered as her ecstasy crescendoed.

She looked at the large decorative mirror on the wall. The sight of the muscular gorgeous teenager with eyes closed, face contorted, mouth open, pounding her ass from behind pushed her over the edge.

She trembled violently. She emitted a long high pitch shriek as she climaxed again. Just then, Andy, with a loud hoarse grunt, erupted inside her. She felt the warm ooze fill her pussy. He grunted and exploded again. He came four times inside her.

He stepped back in a daze. He was confused as what to do now. He could not believe he just fucked his 54 year old boss. For a second, he was afraid he would be fired. He quickly got dressed without saying a word.

Lisa turned around and sat on the couch. She calmly slipped her arms back into the sleeves of her dress and pulled her dress back over her tits. She turned to the mirror and fixed her hair with her hands. She stood up and smoothened out her dress.

"I have an important video call Monday. It's with a Tokyo analytics firm. It's boring but important. I think I could use you there." She said smiling.

Andy let out a gasp of relief. He was glad he was not fired, and he was glad the topic was back to work. "Oh yes, of course." He said. "I would love to be at your side and I'll help however I can."

Lisa guided him to the front door, with her hand directly on his firm ass. They stopped at the door. Andy was smiling, but clearly still shaken. As she opened the door she said "I think you can help me best, not at my side, but under my desk, on your knees, between my legs."

Andy suddenly looked puzzled. As he turned and slowly walked out the door he heard her call out to him cheerily. "Have a good rest of the weekend. But get some rest, I need you in tip-top shape on Monday!"