The Assistant

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Ağu 31, 2023 // By:analsex // No Comment

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All characters in the story are eighteen years of age and older.

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The Assistant


I checked my calendar. Only two weeks until a work/vacation in Cancun Mexico and I was looking forward to it with heightened anticipation. My assistant was accompanying me, and I was delirious with excitement.

I remembered that Tuesday like it was yesterday. My search for a new assistant had been an absolute failure. The candidates were either over or underqualified, too young, or too old. Some of the expectations were beyond belief, eight weeks’ paid vacation, salary demands above what I was earning to name a few.

Barb, my assistant was moving to Denver, and I had two weeks to find someone qualified.

“Hey Jen, I just made some fresh coffee, want a cup? I can bring it in?”

“Thanks Barb but I’ll come out, need to stretch my legs a little.”

When I sat on the end of Barb’s desk, the cup was there waiting for me.

“Where in god’s name am I going to find another you?”

Barb chuckled as the search had been fruitless.

“How many more today? I’m beat and its only just after lunch!”

“One more, her names Paige Gallagher. Job experience is thin, but she graduated from Drexel and is taking courses toward her MBA at Villanova. Looks promising but until you interview…”

“I know, I know but am I asking for too much?”

Barb was suddenly very thoughtful.

“Do ya want some advice from your attorney?”

Barb had recently graduated from law school and was moving with her lawyer husband to the Mile High City in pursuit of better employment and outdoor activities.

“And what’s that…?”

“Don’t give up until the verdict is in. Wait until you speak to all the candidates before you adjust your search criteria.”

While I grumbled, I knew that Barb was right, but was I expecting too much?

“Look Jen, you took a chance on me. You saw something, some potential and worked closely with me to bring it out. You inspired me to pursue my dream and attend law school at night. I owe you, boss!”

“You owe me nothing! Barb, you put in the hours, the work and it paid off. I saw that for you to grow, you’d have to leave the nest. I’m sorry to see you go but it’s in your best interest.”

Barb’s eyes misted over. We’d worked together for almost seven years, and we were friends as well as colleagues. Just then Barb’s phone intercom buzzed.

“Yeah Ruthie?”

“There’s a Paige Gallagher here for an interview.”

I heaved a huge sigh.

“It’s showtime…give me ten minutes before you bring her to the conference room.”

I was mentally preparing for another letdown. Judging from the resume, Paige was twenty-three or twenty-four and probably too young for the position. As I sat in the conference room, I took several deep breaths.

“Come on Jennifer, get yer mind right.” I whispered, remembering a line from the film “Cool Hand Luke” with Paul Newman.

Just then the door opened and in walked one the prettiest young women I ever laid eyes on.

“Hello, Mrs. Dell’Angelo…Paige Gallagher.”

Paige extended her hand and when I gently took it, I swore sparks flew up my arm.

“Oh ah…please call me Jennifer.”

I was clearly stunned by the girl’s beauty; it was disconcerting, and she looked more like a model than an executive assistant. Barb joined us as she usually did, and the interview commenced.

The young woman was sweet, charming, and well-spoken with an infectious laugh that fit her personality to a T. She answered every question effortlessly with wit and intelligence. Finally, the interview concluded but had gone way over time.

“Ms. Gallagher would you mind waiting in the lobby for a few minutes?”

After she walked out Barb looked at me hopefully.

“Well, boss?”

“Barb, I’m a little stunned…is she too good to be true?”

“Don’t think so…passed all the pre interview testing…references all checked out…got her transcripts from Drexel…graduated with a 3.90 GPA. Hmm, not one bit of bullshit on her resume…what’s not to like?”

“I’m thinking she’s too young…won’t be able to handle the pressure…”

Barb gave me the fisheye.

“I was twenty-four when you hired me.”

“You were very mature…”

“And this girl’s not?”

“I dunno…”

“Look Jen…take my advice, unless I’m way off base, she’ll workout just fine. Give her a chance and spend the time training her that you did with me. Patience is a virtue, and the rewards can be great! I think you’ll make a good team. And if I’m wrong, you can come out to Denver and kick my butt!”

“Very funny…kick an attorney? The lawsuits would be never ending!”

Barb gave me a raspberry.

“So? What are ya gonna do?”

“I’m thinking…”

Paige was the first interview that impressed me enough to consider hiring her and there was that electric handshake that kind of unnerved me.

“While I don’t like hiring someone on the spot, let’s bring her in and discuss Bolu Escort job expectations, salary, and benefits. That’ll give us more to go on.”

When I talked over the job requirements and benefits, the young woman was just as if not more charming and sincere. When Paige looked distracted by a knock on the door, I unobtrusively got Barb’s attention and she simply nodded. The receptionist, Ruthie brought in a tray with coffee and as we sat sipping the hot beverage…

“If you’re agreeable, Ms. Gallagher, I’m offering you the position. When can you start?”

Paige looked stunned.

“Ah…I have the job? I wasn’t expecting to…when do need me?”

“This Monday would be ideal.”

“Yes, I can…start then.”

“Good, Barb will show you the ropes and bring you up to speed on policies and procedures.”

With the interview concluded, I sat with Barb as Paige walked out.

“Well Barb…here I go into the unknown…”

“You make it sound like some Sci Fi movie. It’s not that mysterious. Girls got a lot going for her, pretty, and intelligent…you’ll have a hard time keeping most of the horny males, married or single, away from her on company time…”

“Oh no…I forgot about the male population around here.”

“Don’t sweat it boss…girls like Paige know how to handle unwanted attention. She’s probably got a boyfriend or two right now.”

The following Monday, Paige appeared right on time and sat with Barb. Every day that first week, I noticed that she ate her lunch at Barb’s desk and not the employee break room.

On Friday after work, there was a going away celebration for Barb at O’Keefe’s Pub and it was humbling to see the respect and affection her fellow employees had for her. Paige was sitting off to the side and I was determined to make her feel welcome.

“Hey, having fun?”

“Yeah, Barb is a very special person…I know you’ll miss her a lot…”

I felt tears well up in my eyes.

“I’m sorry, I didn’t mean to upset you.”

“Please don’t be sorry. She was not only a colleague but a friend too. I’ll miss her a lot, but her life is on a different path now.”

“I’ll do my best, but I have some big shoes to fill…”

“She was confident that you’d succeed and from what she told me after your first full week…you’ll go far.”

Paige blushed and it was very endearing.

“That was very kind of her. I know I’m kind of young for the position, but I’ll try very hard.”

“Hey, enough work talk…tell me about yourself. Did you grow up around here?”

“No. I’m originally from Wisconsin, Green Bay area but moved here to attend university and stayed.”

“I’m curious, why here?”

“It’s funny you say that because I get that a lot. I tell people to spend a winter in Green Bay and see if they like being frozen seven months out of twelve.”

“That bad?”

“Yeah, but we’re crazy about our football team, the Packers. My dad had season tickets. I’d go to a game or two each season. I do miss that, spending time with him…”

Paige’s eyes misted over.

“Originally, I wanted to major in dance, and there are far more opportunities to pursue here in Philly and with the proximity to New York City. But an injury ended any chance at a career. Plus, I like it here, there’s so much more to see and do…”

As Paige was speaking, I got a good look at my new protégé. She was even prettier up close with dark chestnut color hair, alabaster skin tone, youthful face, and sparkling hazel eyes. When she excused herself to visit the ladies’ room, she had a fluid, graceful way of moving, and it was plain to see that she had the svelte body of a dancer.

I was enchanted by my new employee and spent the rest of the evening chatting with Paige and falling under her spell.

The next Monday was Paige’s first day without Barb and the first day working exclusively with me. We worked closely with each other and except for lunch break, there was very little down time. Paige always ate a bag lunch at her desk, and I was determined to invite the hard-working hottie out for the noon repast at Trattoria Firenze.

“Thanks’ Jen, this is a fancy place.”

“We bring client’s here, and the food is always good. If you’re going to schmooze a prospect, feed them first.”

“I’ll remember that. I can’t afford to eat out much, so this is a real treat for me. Thanks.”

“You very welcome.”

I made it a practice to invite Paige out to lunch at least once a week and I looked forward to our time together. It helped push the stress of my job to the sidelines for a while with this positively alluring creature. There was an innocence, a genuine charisma that she exuded and slowly, inevitably, I became infatuated with her.

Working in the marketing industry can be very stressful and I often wondered why I chose the field. My husband, Ray, was an attorney with a similar stress level. By the time we saw each other in the evening, there was very little time to share with one another. To be honest, we probably should Bolu Escort Bayan have but Ray put very little effort in making time for just us. And as time marched on, he put even less effort into our relationship, when I did my best to engage him in anything interesting.

After trying unsuccessfully to have children, we decided it was best for our careers to not to have any and Ray got a vasectomy. That doomed our sex life which I will mention later.

On Saturdays, Ray golfed with potential clients or hung out with buddies while I usually brought work home with me. I was also expected to pick up and drop off any laundry or dry cleaning, do all the marketing, cook the meals, and the topper, clean the house. Whenever I brought up the idea of hiring someone to clean the house at least once a week, Ray would angrily balk at the notion. Finally, I told him I was hiring someone, and I would pay the expense.

Sunday’s mornings were reserved for sex and later we’d go to brunch and a movie or visit a museum. Our lives had become very predictable and perfunctory, not a breath of spontaneity!

There was very little romance, and I often wondered if he still loved me. He sent me flowers on my birthday and Valentine’s Day but that was it. I’m surprised he signed the card: “Love Ray.” Rarely if ever did he tell me he loved me when I did daily.

Which brings me to Sunday morning sex if I can call it that. After Ray’s vasectomy, our sex life declined too almost nothing. I can best describe it as a patient on life support with little chance of survival, just pathetic. To begin, there was almost no foreplay, I was expected to give him head but he rarely went down on me. Intercourse was usually over in a minute, and I was left hanging. If I wanted relief, I jilled in the shower. In fact, I had to rely on masturbation for my orgasms. He seemed totally unfazed by this and whenever I brought up the subject, he would tell me all the luxuries we could afford. What that had to do with sex, I had not a clue. My frustration was getting worse by the day, and I was willing to compromise for just a mediocre sex life than a lifeless one.

I often said we were like an old married couple when, in realty, we were both only thirty-five. I wanted to make our marriage work but while I put in the effort, he did nothing to improve the situation. I started imagining what it would be like to have an affair, and little did I know, I was ripe for just that!

With so much time and effort devoted to work, I found myself growing closer to my young protégé. After a very taxing week, I was in my office trying to massage my tense neck when Paige walked in.

“Neck hurt?”

“Yeah, can’t seem to get the kinks out. Shoulders feel tight too.”

“Have you ever tried yoga?”

“No. Do you think it will help?”

“Yeah, I practice at Lotus Blossom in Manayunk. I go at least five times a week. Wanna try it?”

“As long as you think it will help, I’m game!”

Now I’ve always been a devotee of exercise and arose very early and went to the gym Monday through Friday for “boot camp.” It kept me in excellent condition, lean and hard bodied.

My introduction to yoga was illuminating, and I liked it so much that I went with Paige after work and on Saturdays, soon we bonded as friends. The sight of her in yoga clothes was jarring, the girl had a beautiful body, and I was infatuated with her. Then they came, the sexual thoughts. At first, I tried to banish them, but it was useless, and I’d find myself imagining what she looked like without clothes.

We’d been working together for about four months when an important project was dumped in my lap. Luckily my budget allowed me to pay Paige overtime. Since we lived relatively close to one another, I proposed meeting at my home on Saturday mornings instead of the long trek to the office.

“Very casual dress is fine. We want to be comfortable when we work and if it’s nice, out by the pool.”

Paige’s eyes lit up.

“You have a swimming pool?”

“Yeah, I spend a lot of time out there in the summer. Hey, if you want, bring a suit and you can take a dip to cool off.”

“Gosh, thanks Jen. I just might take you up on that…”

Paige had a down home folksy goodness that was enchanting and lit a fire inside me. Her artless demeanor was infectious, and I had a clear picture of a guileless young woman, unfamiliar with big city ways. It confused me because I’d never been attracted to another female on an emotional and physical level.

I absolutely loved spending time with Paige outside of work. There were times when I intuited that the attraction was mutual, but I wasn’t positive. However, she never mentioned having a boyfriend or dating for that matter.

Later I came to the realization that I was gonna see my assistant in, if I was lucky, a bikini. Further, my husband was going on a golf outing and would be gone the entire day. Lucky me!


Where do I begin? What does one do when they’re smitten with their boss? Escort Bolu Jennifer Dell’Angelo was a hottie, but I doubted she had any idea that I played on the girls’ team. Everyone probably thought I was heterosexual when I was a dyed in the wool lesbian. If fact, there wasn’t a time when I didn’t know I was gay.

When I interviewed for the position at Brighton and Parks, and was hired the same day, I was shocked. Before the interview, I had serious doubts that I stood a chance because of my experience level. My two years with Conyers and Associates was hardly enough and truthfully, I was nothing more than a glorified “go fer” trying to learn the ropes.

When I met Jennifer, she took my breath away. When I extended my hand for a shake and she took it, I swear sparks flew up my arm. Dressed in classy business attire, she exuded self-confidence and maturity. While she had a no-nonsense attitude, I detected a softness behind the façade. There was a sweet, caring person there, I could feel it and I was certain that she wanted me to succeed in the position.

We spent a lot of time working closely with one another and her patience level was remarkable. She took great pains to explain everything in detail and insisted there were no “dumb” questions. Little by little, Jennifer gave me more responsibility to handle. Her faith in me to perform, just made me work that much harder.

Socially, while I had a few friends both straight and lesbian that I spent time with, I had no significant other. My problem? I had a knack for falling for straight girls/women. I was highly attracted to “older” females, mid-thirties to mid-forties. They were usually married and while I might rock their word sexually, it was never enough to sustain a long-term liaison.

My last serous relationship ended with me getting hurt. Julissa was a married professor of Language Arts at Temple University. I showed her how the “other half” lives but after six months, she decided that she wanted to stay married. That was two years ago and unfortunately for me, I disliked random hook ups and stayed out of lesbian bars. While I had an occasional “fuck buddy” it wasn’t very satisfying as I hungered for a meaningful relationship.

I was twenty-four when Jennifer hired me and lonely enough that I was contemplating returning to Wisconsin.

Then, Jennifer noticed that I always ate lunch at my desk. Unbeknownst to her, I shied away from the break room to avoid any unwanted male attention. She invited me every Friday to the upscale Trattoria Firenze. It was a very kind gesture and she absolutely refused if I wanted to reciprocate. I adore Italian food and to my mid-western palate, it was delicious. There were times when I’d make an excuse not to go but she wouldn’t hear of it and would sit on the end of my desk until I relented.

It was during our lunch hour that I really got to know Jennifer. She had this infectious laugh and dry sense of humor that appealed to me. Often, she talked about her family, particularly her sister, Anna, and her father. It was apparent that they had a close relationship. I knew Jennifer was married but she rarely talked about her husband and only in passing which I found kind of odd.

During lunch, when I tried to talk about something work related,

“I have rule, no business chatter at lunch. Let’s enjoy our meal.”

While alcohol consumption was off the table, I tried a “Virgin Mary” with tabasco and loved it.

Because it was casual Friday, she’d wear stylish clothes that looked molded to her body. Although she was a couple inches shorter, she walked with a confident air and yet, there was no evidence of conceit or arrogance.

I started to wonder with all the hours that Jennifer worked how she stayed in such marvelous shape.

“Oh, I go to “boot camp” class, Monday through Friday at six am. It’s one hour of butt kicking exercise and weightlifting.”

I’ve been a devotee of yoga since my high school days and when I invited Jennifer, she fell in love with it. With all the intense exercise, I often wondered what she’d look like in a bikini. Then, fate intervened, and my prayers were answered.

A very important client was assigned to Jennifer’s unit, and it meant working overtime on Saturday mornings at her home. Her plan was to start at eight am and knock off at noon or one pm. When she told me we would work by her pool, weather permitting, I was ecstatic.

“You can bring a swimsuit, if you want and take a refreshing dip to cool off.”

Before that first Saturday, I fretted about what would be appropriate. I had every bikini I owned on my bed, trying them on one by one until I was totally confused. I’d appraise my body in the mirror and its true when the experts say we’re our own worst critic.

Before a serious injury to both knees ended my hopes for a career in dance, I was considered very talented. I’d spend hours practicing moves and routines. After six months in rehab, my knees were never going to hold up to the strain.

Yoga became my mainstay for exercise, but I also incorporated cardio, and a gal pal got me started on weightlifting to harden my body. The result is long lean muscles with no bulky look at all. Numerous squats transformed my butt into a prominent bubble, and I think it’s my best “ass-et”

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