Mixing Business and Pleasure

by Softly

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Mult, Consensual, Reluctant, Coercion, Blackmail, Drunk/Drugged, Slut Wife, Cuckold, Swinging, Gang Bang, Group Sex, Oral Sex, .

Desc: Erotica Sex Story: Their Boss set the wives up to satisfy the clients, and himself. Then it was payback time, until the prospect of Big Bucks, changed a lot of minds.

I was standing at the dispatcher's desk, when she approached me. "Captain McHale, I'm Diane Williams. I will be your co-pilot tonight. Are you ready for the crew meeting?"

With a smile, I said, "yes."

It was a brief meeting. "If you observe anything that you think might effect the comfort of the passengers or the safety of our flight, please notify me immediately, no matter how trivial you think that it is."

The flight attendants all nodded.

As a junior captain, I bid the 11:45 PM flight to Atlanta, known as United 842. It was no secret that the reason the flight was scheduled at that time was the Post Office contract. We were a mail plane. The income from the passengers was just gravy. After Atlanta, we continued to Little Rock, and then to Dallas. After twelve hours down time, we did the trip in reverse.

"Ms. Williams, would you like to drive us tonight?"

"Love to. Had a captain last month that never let me touch the controls."

"There are some of those assholes still flying the line."

She chuckled. "Exactly."

"United 842, cleared for take off."

"United 8 4 2 rolling," I intoned. In moments, I crisply said to Ms. Williams, "V 1... V2. She rotated our 737 at 146 knots. Precisely, she flew the climb profile, as I expected that she would. I relaxed as we passed through ten thousand feet.

At that time of night there is little traffic. We were at thirty-six thousand, on autopilot. I noticed that her eyes continued to scan the instruments, the sign of a pro. Without looking at me she inquired, "you married?"


"Wife catch you a being a badda boy?"

I laughed. She cast me a sideways look. "No. In fact she was going on hot and heavy with the attorney that she worked for. I was still a co-pilot, making a lot less money. I think that her mommy made a lot of derogatory comments about me being away so much."

"Did the attorney dump his wife for her?"

"Shit no. He fired her the day that he found out that we had split."

"You're a good looking guy. Any serious relationships?"


"I'm divorced. If you don't mind, I'd like to spend our down time together?" She turned her face towards me. Her eyes locked on mine.

"I would like that."

She smiled. "I would bet that a lot of women have come on to you."


"Tell me about it?"

We were in our little world that only pilots know of. From our altitude, cities such as Indianapolis, Louisville, Lexington, and Knoxville would slide by in slow motion beneath us, while the stars twinkled above. Our metal tube was moving at over five hundred miles an hour, so the engine noise was behind us. There was just the hiss of the air.

"When I was in high school, girls would come up to me and ask me to take them out on a date. I was a lifeguard at Lake Forest Beach. When I was seventeen, a twenty-four year old gal asked me to date her. She was beautiful. We dated. No funny stuff. Just nice dates. Why she wanted to date me, I'll never know."

Diane smiled, and chuckled. "You would probably have to know the last guy that she dated to understand why she dated you."

It was my turn to laugh. "Anyhow, my dad sat me down and told me that making babies was not a good idea. I heard my mother telling one of her friends on the phone that I was like catnip to girls. I looked up catnip in the dictionary to see what she meant."

"I'll bet that was confusing as hell to a guy your age?"

"Very much so. It got worse when I went to Lake Forest College. I must have been the poster boy for the type of guy that mothers told their daughters to snare. At one point, it was so bad that I let my beard and hair grow so as to hide my face so that girls could not see what I looked like."

"That work?"

"Not really." We both laughed.

"You have sex with a lot of girls in college?"

"Can I plead the Fifth?"

"I had sex with seven."

"For me, it was three, including my wife to be."


"The three most beautiful women that I have ever know."

That is quite a statement, considering the hundreds of flight attendants that you have met. What was your wife like?"

"She was a Miss Illinois."

"What was her talent in the Miss America Pageant?"

"Singer. Since we divorced, and her attorney friend dumped her, she has gone to Hollywood. She has had two small parts in pictures."

"Did she try to get back together with you?"

"Yes. But I said, thanks, but no thanks."


"It wasn't that some guy had gotten into her pants. It was more that she was full of herself. When a co-pilot, she gave me a load of shit about that she deserved better than I was providing."

"I can understand your reaction to that."

I turned to look at this Diane Williams. She was average build; clean cut, crisp looking, with no make up. I was attracted to her. She had matter-of-factly told me that she wanted to have sex with me. Then, she had gone down a checklist of questions about my life that a woman would be interested in. "Why did you bid this flight? With your seniority, you could have bid more convenient flights." I asked.

"I have seen you around. I wanted to get to know you."

I was stunned. "Whoa, gal. Are you saying that you planned this last month when you bid your flights, so that you could sleep with me?"

"Absolutely. Does that scare you?"

"I'm an airline captain. Scare does not enter my thinking. Wondering what the hell I'm getting into does."

She turned to face me square. "I'm as much woman as you are man. The chief pilot, Johnson, told me that I'm an exceptional pilot. He compared me to you, Tom Mc Hale. Said that the FAA examiner was awed by your last six-month flight test. I want to get to know the best of the best, Mister, and you're it."

"I've never met a gal like you?"

"That's right." We both laughed.

"This will be interesting. So, why are you divorced?"

"He was captain of the football team at Michigan State. He also was an academic All-American, as well as president of our senior class. You might have heard of him? Matthew Williams. I worked while he went to law school. Things went sour when he went to work for the Firm of Mead, Johnson, Wing, Hudson, & Bernstein. He became obsessed with becoming a first chair, trial attorney. To the point that he volunteered to take trial cases anywhere in the state. He was never home."

"Was he having an affair, too?"

"Not that I know of. I brought up the idea of either spending more time with me, or we would split. Wanted to scare him. He said, fine. He had been thinking that he didn't have time for a family. Ninety days later, we were divorced. I have never looked back"

"I can see why."

"United 842, Atlanta center. Descend and maintain flight level 2 4 0."

"United 8 4 2 out of flight level 3 6 0, for flight level 2 4 0."

At 0645 we landed at Dallas. The van took Diane and I to the hotel. We showered, each in our own room. Diane joined me for breakfast. Now adorned with a casual sundress, and heals, as well as makeup, she would no longer be confused for a man. I stood to greet her.

"A gentleman, I see." She said with a smile.

"I don't normally differ to co-pilots."

Under her breath, she observed, "Unless, of course, you are planning to join me for some fully acrobatic flight between the sheets?"

"Woman, you're bad."

"So I've been told."

Later, when we had adjoined to my room, she held eye contact as she removed her clothes. "Cowboy," she said. "I'm like a wild filly. You need to come on to me very slowly, and gently. Take your time and move a step at a time. I'll tell you when I'm ready for you to ride me. I see that you have a nice package."

"Where do you want me to start?"

"Some plain old kissing is as good as any."

I knew from that first kiss that this was one hell of a lot of woman in my arms. Her whole body was part of the kiss. She moved my hand to her breast. I'm not usually much of a titty man. But when I took hers in my mouth, her reaction made me one. This was no act. Her body turned red, as sweat formed all over her body.

"Down there." She commanded in a hissed whisper.

I started to kiss her legs near her knee. Her hands pulled my face to the junction of her legs. The smell of her sex was intoxicating. My cock was ramrod stiff.

"Are you ready?" she cooed.

I slid upward. Her hand guided my cock to her entrance. Found, it slid inward. She took both sides of my head in her hands. Our mouths joined for the most wonderful French kiss that I have ever experienced. At the same time, her body begins to undulate, and pump her bottom up and down as well as sideways. I was not fucking her. Rather, her pussy was consuming my cock, as no woman had ever done before. All too soon, we both came. There was an act two, equally as fine as the first. We fell asleep in each other's arms.

That night, in the wee small hours, while still at flight level 3 8 0, sixty minutes out from O'Hare, Diane said. "Tom, since we will have three days off, I was thinking that I would go to my apartment to get some things. Then, come over to your place to spend some time with you."

"Ho, ho, ho. You're something else. What makes you think that I want you to invade my space?"

"Cause, I'm the most woman that you have ever meet, as well as the best sex, Cowboy."

"You're right on both counts. I was going to ask you. You beat me to the punch."

"You have to get up very early to get ahead of me. My Mommy did not raise any dumb kids."

Five months later a justice of the peace married us. I met Diane's mother and father, who were fine people. Her mother was a firecracker. Her dad was a savvy old guy who smiled a knowing smile when I commented that his daughter was a whole lot of woman.

United went bankrupt. Diane and I were laid off the same day. I had already purchased a bugler and fire alarm company franchise, which was doing well. Two employees and I had all gone to their school. I had appointed Fred Brown to be the manager, since I was out of town fifteen days a week as a pilot.

Diane took a job working for Wolzenburg Fine Gems, a wholesaler company located right here in Lake Forest. When she mentioned the names of the two other women who worked in the office, I almost fell out of my chair. "Did you say, Susan Prendergast and Grace Devine?"

"Yes. They are both very pretty. Do you know them?"

"You could say that. Do you remember that I told you that I had sex with three girls while in college?"

Diane turned to look at me. She set the pan in her hand down. Her eyes looked at my face. She had a bemused look on her face. "Tom?"

"It is a very small world."

"Have you had any contact with them since college?"

"I was invited to both of their weddings. I know their husbands well, and like them both."

Time passed. Diane came to like both Susan and Grace. She never told them that she knew that I once had sex with them both. Each asked her how I was doing, she reported. Then one day I could tell that Diane wanted to tell me something. Finally, I asked. "Something going on that I should know about?"

"Let's sit and talk." When seated, she continued. "Tom, a month ago, I left work at five. I went a few blocks and then remembered that I had forgotten something that I wanted to work on at home, so I went back to the office. I head some noise coming from Mr. Wolzenburg's office. Peeking, I saw Grace giving him a blowjob."


"Gave me a lot to think about."

"What does this guy look like?"

"He is big, well over six feet, and must be all of fifty. He is hung pretty well. That isn't all. Since I knew that some hanky-panky was going on, I would leave at five and go around the block. If either Susan's or Grace's car was still there at fifteen after, I would sneak back into the building. Low and behold, the next time it was Susan sucking old George off. But that wasn't all. When he got hard again, he backed her up to his desk, lifted her skirt and entered her, like he owned her."

"Whatever he is doing, it seems to be working. It will be your turn next."

"That is why I brought this up. You know as well as I do, that we need my salary to get by until we get back to flying, or your company builds up more clients. Tom, Mr. Wolzenburg wants me to accompany him to a three-day conference in Cleveland. You know that he plans to come on to me. What should I do?"

We sat without saying a word for several moments. My mind was racing, as a professional pilot is trained to do to examine the, "What Ifs."

"Do you mind screwing him?"

"No. I like him as a person. You know that I like sex. He is well hung."

"From what you have told me, he must have something on Susan and Grace for them to give him blowjobs. As I recall neither girl was all that hot for oral sex. Go along with his act to see if you can find out what he has done to them."

"Yes, Captain."

Just before she left to go meet George Wolzenburg at the airport for the flight to Cleveland, I kissed her. "Call me and tell me exactly what has occurred."

"You don't want me to wait until we are alone in bed?"

"No. Tell me exactly what he tries to do when you phone."

"How about if we have had sex?"


That evening at just after nine, the phone rang.


"Perfect gentleman. Ate with several men at dinner. Talk was all business. Am in my own room. Will change and join him and others for a trip to a nightclub."

"Have fun."

At just after three AM the phone rang. "Yes?"

Diane's voice sounded like she was in a barrel. "Tom. Tom. It happened."

"What happened, Diane?"

"Please don't be mad, Tom?"

"It's just sex, Baby. What happened?"

"There were four of us that went out to a comedy club. Larry the Cable Guy was on and he was hilarious. Well, it turned out that George does a great impression of Larry, Jeff and that Texas guy, Ron White, with their Redneck jokes. He had us all in stitches. I drank too much. Was having just the greatest time. We returned to the hotel. George walked me to my room. When I opened the door, he barged right in, and started kissing me.

I know that I should have said no, but then I would have never known what he had on Susan and Grace. Besides, to tell you the truth, I was horny, and didn't want to shoot old George down. He was so excited.

Quicker than I can tell you, he had me naked, was naked himself, and was working on all my zones. I didn't mind a bit when he started to ride-the-lady."

"I wonder how many other men have heard anything like this from their wives?"

"There is more, Tom."


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