Ride Along

Everybody liked Bernie. Her given name was Bernadette but everyone called her Bernie. She was a hard worker, a live wire and an inspirational leader. People loved being around her and worked hard for her because she busted her ass, was always positive and enthusiastic, had a great sense of humor and could sell ice cubes to an Eskimo in February. Oh, and she was also hot as a firecracker.

Bernie was in her early forties but looked ten years younger. She was of medium height with light brown shoulder-length hair, pretty face, a mature, slim body with all the right curves and nice firm boobs jutting straight out. She had a way of turning heads wherever she was whether it was because of her infectious charisma, her impeccable dress or her incredible body.

She was a Vice President of Sales for a large marketing firm. But her style was unlike that of the other VPs in the company. The others tended to spend most of their time at the corporate office holding meetings, working at their computers or talking on the phone. But Bernie spent much of her time in the field. She still serviced a large number of accounts herself while the others only handled a cherry-picked few. She also spent a lot of days riding with the sales reps under her umbrella, meeting their clients, learning their territories and helping them sell.

Bernie had a sales manager working for her named Wendy. Wendy was Bernie's polar opposite: A fat dead-serious Jewish woman with a grating nasal voice, annoying personality, no sense of humor and seemed to take little or no enjoyment from her work. She was all about the numbers.

They were planning to open a new territory in an outlying area that was a two-hour drive from the office. They would need a qualified self-starter who could get up and running and become productive quickly and could work unsupervised most of the time. It was decided that Wendy would interview the applicants and any that she deemed strong candidates would then be interviewed by Bernie. They had both interviewed five applicants when Wendy asked Bernie to interview Jayden. 'This could be the one', Wendy had said.

BERNIE:

I remember when Jayden walked into my office for his interview. My very first thought was, 'Wow, this kid sure is nice to look at'. He was mid-to-late-twenties, tall and I could tell he was muscular underneath his snug dress shirt. He was ethnically handsome with a dark complexion. His black hair was pulled tight against his scalp and tied into a pony tail which was tucked into the back of his collar and down inside the back of his shirt. He made a good first impression, had a professional appearance and I instinctively knew he could represent the company well.

His resume was pretty much what we were looking for too: College degree and some, but not too much, related experience (the company had its own culture and liked to mold its own). He was sharp, quick-witted and very likable, and spoke with a clipped, indiscernible articulation. Within five minutes I knew two things: One, I was going to hire him, and two, I was going to supervise him myself.

JAYDEN:

After the first interview I didn't think I'd get the job, and wasn't even sure I wanted it. Wendy seemed to be so serious and such a ball-buster I just couldn't imagine working for her. But when she said she wanted me to interview with her boss, a VP named Bernie, I figured 'Okay, what the hell'. I went to the interview the next week and had no idea Bernie was a woman until I walked into her office.

What a knockout! She might have been older, but she was fucking hot. Great thin body and nice firm tits all wrapped up in a cool blue designer business suit with just enough skin of her upper chest visible to give my dick a buzz. I tried not to let my eyes linger there but I'm sure she caught me.

We hit it off immediately, she was nothing like Wendy. Bernie was enthusiastic as she described the position and asked all the typical interview questions and she had a magnetic smile and laugh. I liked her immediately.

A few days later I learned that I got the job and was relieved and flattered to hear that Bernie would be my direct supervisor. She mentioned that Wendy was already spread too thin but I think she may have sensed that me and Wendy would have been like oil and water.

--

Jayden started work three weeks later. The first week was classroom training with other new employees. The company put him up in a local hotel so he wouldn't have to drive over two hours each way each day. A couple evenings after class he met with Bernie in her office and they discussed his prospects, his work plan and goals and mapped out the new territory. Bernie said that she would try to arrange to ride along with him at least once every couple weeks for a while to help him get off to a fast start. Both times they were in her office till after seven p.m. On Wednesday evening she took him out to dinner and they talked business and it was after eight by the time she dropped him off. It appeared that he would be working for a workaholic. He'd noticed she was in early and went home late.

"You really work long hours, don't you, Bernie?" Jayden asked her at one point.

"Yes, I guess I do," she said, "But I love what I do. My daughter is grown and out of the house and my husband Fred is an airline pilot. He flies from the U.S. to the far east...Tokyo and Hong Kong...and back every week. He is gone Sunday till Thursday. So I work a lot during the week, and go home to a big, empty house.

'Hmm', Jayden thought to himself, wondering if she was getting enough at home.

On Friday, the final day of training, Bernie told Jayden that she would come out and ride with him the following Wednesday. She asked him to set up a full day with four or five confirmed appointments and they would make some cold-calls too. They were going to close some sales.

--

Jayden had five set appointments. They went 0-for-2 in the morning but closed two out of three in the afternoon, and managed to set up several appointments for the coming days. Jayden would let Bernie kick things off and then follow her lead. They quickly developed a chemistry together. The prospects seemed to enjoy their performances.

Jayden got the hang of the job quickly and was doing pretty well on his own, but every time Bernie rode along with with him was a productive day. Unless appointments canceled on them, they'd always manage to close one or two and identify some good future prospects. Bernie would arrive early and they would haul ass all morning, then Bernie would treat him to lunch, and then they'd haul ass all afternoon. Then right before they parted at the end of the day Bernie would get out her datebook and schedule their next ride-along.

Each day they spent together was seven or eight or nine hours in close quarters, in the car, side by side in front of a client, at a cozy table for lunch. They became very comfortable together, their inhibitions lowered. They laughed together, occasionally touched one another during conversation, and shared personal information.

"Can I ask you a question?" Bernie asked him one time at lunch.

"Sure," Jayden said. "What?"

"You have a slight accent. It's very unique. Where are you from?"

He smiled and sat back. "I was born in Curacao and lived there until I was twelve. Then my mother wanted me to be educated in the States and we moved here. My father stayed."

"Ah, interesting. How did your parents meet?"

"My mother is American. A tall blonde with blue eyes. She was a senior in college and in Curacao on her Christmas break when she took a snorkeling trip and met my father. He was Captain of the boat. She went back home and finished her final semester of school with me in her belly. As soon as she graduated she went back to him. They were together until she brought me here when I was twelve. She begged him to come but he had no interest. He's still there, still running boat charters. We've stayed in touch and I visit him from time to time; he is always after me to move back and go into the business with him. I probably will some day."

"Your father sounds like a character from a Hemingway novel."

"His name is Alonso. He is a descendant of the Caquetio Indians and the Dutch. He loves where he lives and what he does."

"That's the secret of happiness, I think," Bernie said. "Who, what and where. Sounds like your father has at least two out of three."

"Huh?" Jayden asked.

"Who, what, where," she said. "Who are you with, what are you doing and where are you doing it? If you are with the right person, are doing what you want and live where you want to be, that's true happiness. If you have two out of three you can be reasonably happy too. Less than two, I don't think so."

"Hmm," he said. "I never thought of it like that. Interesting."

"How about you, Jayden? Where are you on the scale?" Bernie asked. Her eyes were wide open and staring into his. He detected a slight semi-wink from her left eyelid.

"Two out of three. I have the what and the where."

"No who?" she asked.

"Nah, not right now, I'm too busy with the new job and everything." he said. "My last who ended months ago. I'm currently who-less."

Bernie laughed and paid the lunch tab. They went back to work and sold a new account that afternoon. At the end of the day Jayden watched Bernie drive off and thought about that little sparkly wink in her eye. He had a brief thought about Who's Who and then instantly put it out of his mind.

--

BERNIE:

After a couple of months I could have ceased and desisted with the ride-alongs. Jayden was doing a very good job on his own. But I didn't because I was getting as much out of it as he was, I think. Those days riding around with him were a nice change of pace from my days around the corporate office. I really enjoyed his company and I could tell he enjoyed mine. Whenever I was with him I would sneak peeks at him. I found myself dressing up for him. He was always checking me out, I could tell, and I was checking him out too, believe me. Sometimes we flirted a little.

I think there are times we come to in life where we have to make hard decisions and take a risk. Risk, or lose out. I could hardly believe it, but I started actually contemplating taking a big risk. Risking my marriage, risking my job, risking my reputation. With a young employee only a few years older than my daughter. My brain was saying no, but another part of my anatomy was screaming yes, yes, yes!

In twenty-three years of marriage I had never cheated on my husband. Men had come on to me plenty of times over the years but I'd never strayed. My husband had, though.We learned the hard way that him flying halfway around the globe and back every week, and crashing at airline-owned condos in the Far East with other crew members could lead to some shenanigans. Now, for the very first time I was considering it. Adultery, that is.

JAYDEN:

We became pretty comfortable together. We made a good team on sales calls. We shared a lot of laughs and there was definitely a mutual attraction despite the age difference. We were both a little flirtatious but it was all just innocent, playful fun. If Bernie hadn't been my boss I would have made a move on her, married or not. But she was my boss and I knew it would probably never happen.

One time I made a follow-up sales call to a client I had seen the week before with Bernie. 'Where's your girlfriend?' he asked. I played dumb and he added, 'You know, your girlfriend you came in here with last week'. 'Oh, Bernie', I said. Then he asked, 'You tapping that?'. 'Bernie, hell no, she's my boss!' I said incredulously. He said: 'I know that, but it wouldn't be the first time it happened. You sure you're not tapping that?' I assured him I wasn't. Not that I hadn't thought about it, though.

--

It was very early on a Tuesday morning. Bernie was in the shower when she decided what the hell, this would be the day. She quickly scrubbed her body clean, shampooed her hair and rinsed off. She dried herself and dressed in one of her hottest pantsuits. She added a touch of red lipstick and smoky eye shadow. She logged on line briefly and booked a hotel room for that night. Then she packed an overnight bag and got into her car and began her two-hour drive to spend the day with Jayden.

They met in their usual place, a shopping center which conveniently had plenty of parking and was directly across the street from the hotel where she would stay that night, hopefully with company. If she was going to enter into an affair, she reasoned, then doing it two hours away from home was the way to do it.

Jayden had a full day planned for them and they ran hard all morning and afternoon, not even having time to stop for lunch. They grabbed hot dogs from a street vendor as they hustled from one appointment to the next. They managed to sell two new accounts and it was almost six o'clock when

Jayden dropped her off at her car.

"Do you have plans tonight, Jayden?" Bernie asked.

"Nothing big tonight. Go home, heat up some rice and Chunky Soup. Recover from the way you run me ragged. Rest up for tomorrow."

Bernie laughed. "Would you like to have dinner with me?" she asked.

"Dinner with you?" Jayden said with surprise. "Tonight?"

"Yes. We didn't get much of a lunch today and I'm staying over there tonight," she said, pointing at the hotel. "I wasn't up for the long drive back. Are you up for dinner?"

"Uh, sure," he said. "I'd love to."

"Okay good, I'll enjoy the company. I want to get a shower and I have a little bit of work to do. How does seven-thirty sound?"

"Seven-thirty sounds fine."

"All right, let's meet in the lounge. I'll buy you a drink."

Jayden headed home to get a shower and some fresh clothes.

--

When Jayden entered the lounge at seven-thirty Bernie was already camped out in a small booth along the wall. She was talking on her cell phone, frantically waving her hand as she spoke and had scattered papers and a half-empty glass of wine on the table in front of her. She spotted him and waved him over.

Jayden sat down and waited while Bernie finished her call. She was talking to one of her managers about one of her areas. A waitress came by and he ordered a draft beer.

"So here we are, thanks for coming," Bernie said when she finished her call. She slid a piece of paper across the table. "Here, sign this. Then our work is done for the day."

"What is this?" he said as he picked up the paper.

"It's your ninety day review. Don't worry, you aced it. Just a formality and now your probationary period is over and your benefits kick in." She sipped her wine. He signed it and slid it back across the table.

The waitress returned with his beer and Bernie ordered another glass of wine. They made small talk for a few minutes. Jayden was a little nervous and tried not to drink his beer too fast. He noticed some men in the room checking them out. They'd noticed that this stylish older woman had been busy in her booth by herself and now this young guy strolled in and joined her.

Jayden was into his second beer when Bernie steered their conversation into shop talk.

"So, Jayden, now you're a crusty, old employee of ninety days. What do you think?"

"What, about the job?"

"The job, the company, your boss, the whole shebang. How do you feel about it?"

"I'm happy with it," he said. "The work is harder than I thought it would be, but the company offers good product and delivers on their promises. Most clients seem satisfied and the ones that have had issues get taken care of. I'd like to make more money but I know that will come, I can see growth in that area already. And you have been great. You are a great help and I appreciate it."

"Well, thank you and you are welcome. Your success is my success, remember that. The better you do the better we both look."

"Here's to looking good!" Jayden said, raising his glass.

Bernie laughed and raised her glass. "To looking good," she said, and gave him her sparkly wink.

Jayden thought, damn right you look good. She had on a fine white blouse with a gold pendant peeking through the top two open buttons. A trace of nipple nudging through the fabric above the tabletop. Red, sheeny lipstick.

The waitress came by again and Bernie asked for menus. She asked Jayden if he minded if they had dinner in the lounge instead of the dining room. He said he didn't. 'It's cozier, more intimate', she said. They ordered another drink. They were loosening up.

Dinner arrived in short fashion. Bernie had a Greek salad and Jayden the Club Sandwich. Eating light. About halfway through the meal there was a brief lull in the conversation. Bernie knew it was time.

"You know, we've had a lot of success and fun these last few months on our days riding together, haven't we?" she said.

"Yes, we have."

"You set 'em up, and we knock 'em down," Bernie said. "You could have a great future here if you want to."

"I hope to," he said. He noticed her eyes were wide open and staring into his.

There was a brief silence. They took sips. Their eyes were locked.

"You are getting the job done, no doubt about that, Jayden. But even though you are doing a great job, I have to admit that there have been times when I've wondered whether it was a mistake to have hired you."

"Really? Why?" he asked.

"Can I be brutally honest with you, Jayden?"

"Yes, please."

"Okay. I've been doing this kind of work for a long time. I started on the ground floor, worked hard, worked my way up, took night classes, became a manager and now I've been a VP for six years. And in all that time I had never found myself in the situation...in the predicament...I'm now in with you."

"What do you mean?"

"Come on. I've seen you checking me out. And don't tell me you haven't caught me checking you out. Agreed?"

"Agreed," he said, his voice slightly breaking.

Bernie leaned closer so their faces were inches apart. Jayden could see a glassy green brightness in her eyes and tiny trickles of sweat above her ruby lips.

"This is the first time I... You are the first man ever to work for me whom I've wanted to fuck," she said softly.

There was a long silence as they sat staring at one another. Bernie was suddenly very afraid she'd gone too far and had blown it.

"What do you think about that?" she asked nervously.

Jayden was silently shocked. After a moment he said, "All I can think of to say is yes, good. Sounds like a plan."

Bernie sat back a little, relieved. "I'm quite a bit older, does that bother you?"

"No."

"Do I turn you on, Jayden?"

"Yes."

"Good, you turn me on too. Can you keep our secret?"

"Yes."

"Good. Want to come to my room?"

"Yes."

--

JAYDEN:

I couldn't believe what was happening. It was surreal, like my head was separated from the rest of my body. It seemed like a long walk to her room even though it was just down the end of the hall from the lobby. I didn't know what to do, should I hold her hand, should I touch her? I wanted to jump her bones, but she's my boss! How does she like it? She wants to fuck, that's for sure, but what else? How far should I go?

As she was unlocking the door to the room my brain slowed down enough so I could relax a little bit and think straight. I realized that SHE PLANNED THIS. The hotel room, the dinner, the drinks. Then her telling me she wanted to fuck me and knowing I wanted to fuck her.

BERNIE:

I was thinking, finally, I'm going to get to fuck this kid. God, I was relieved when he said YES! I thought that he would, but you never know for sure and it would have been pretty embarrassing if he'd turned me down. That would have been an awkward situation I don't think we could have recovered from. But I was confident enough to go for it because I knew he didn't have a wife or girlfriend, I was pretty sure he wasn't gay, plus I'd seen him peeking at my tits and my ass and my crotch enough times and I knew he liked what he saw.