What A Deal Ch 31

A reminder that this is part of a Non-Consent/Reluctance series. If you don't want to read about sex where someone is put into that position, then stop now and move on.

This is a continuation of what would be considered a "stroke" story, or as I like to call then a Jack(off) and Jill(off) story. I got some requests to continue this not very serious, fictional sex romp, so I'll try to keep up.

In the last chapter, Cindy and Dennis had finally gotten Barb to play with her and Dennis. However, things were about to take an odd turn for the entire group.

Recurring Cast

Dennis, 42 years old, 5' 11", 175 lbs, brown hair, blue eyes, Cindy's husband.

Cindy, 42 years old, 5' 4", 105 pounds, brown hair, blue eyes, Dennis' wife.

Diane, 42 years old, 5' 7", 140 lbs, auburn hair, green eyes, recently divorced friend of Cindy's.

Becky, 39 years old, 5' 9", 155 lbs, blonde hair, blue eyes, Cindy's friend, widow.

Jack, 43 years old, 6', 185 lbs, black hair, brown eyes, Louise's husband.

Louise, 39 years old, 5' 4", 130 lbs, blonde hair, brown eyes, Jack's wife.

Jackie, 20 years old, 5'6", 125 pounds, dark brown hair, blue eyes, neighbor girl.

Katy, 20 years old, 5'6", 115 pounds, blonde hair, blue eyes, Jackie's friend, now Dennis' sub.

Suzanne, 37 years old, 5'5", 125 pounds, brown hair, brown eyes, neighborhood acquaintance.

Bill, 39 years old, 5'9", 170 pounds, black hair, brown eyes, Suzanne's husband.

Brittany, 28 years old, 5'8", 120 pounds, red hair, blue eyes, Jimmy's wife.

Jimmy, 23 years old, 5'10", 160 pounds, brown hair, brown eyes, Brittany's husband.

Lucy, 28 years old, 5'5", 105 pounds, auburn hair, blue eyes, elementary school teacher, Ed's wife.

Ed, 29 years old, 5'10", 180, pounds, brown hair, brown eyes, Lucy's husband.

Jan, 29 years old, 5'5", 130 pounds, brown hair, blue eyes.

Barb, 26 years old, 5'2", 125 pounds, blonde hair, blue eyes, Wes' wife.

Wes, 28 years old, 5'8", 190 pounds, brown hair, brown eyes, Barb's husband.

------ 6 months after Barb's seduction ------

Over the next six months, the company went through a major move and reorganization. The entire operation, due to the increase in contracts up north near the major city where I had done a lot of work, was moved to just south of that major city where there happened to be a large warehouse area. One of the warehouses was changed into office space and almost everyone moved up there. This included Barb and Wes from across the street.

Cindy, Katy, and I didn't want to move. As a key member of the company and now a senior VP, the CEO, who was very thankful of all the work I had been able to get for the company, gave me the choice of working a couple of days a week in the new office and the others at home. He would let me set my own schedule. It was a great deal. We had an apartment over the garage that we had used time to time whenever I had to work from home, so we turned half of it into a full-time office.

Along with this change, I lost my administrative assistant. She was married to one of the individuals moving north, so they moved up there and the company found her a new job. I had to find a new assistant.

I discussed it with Cindy.

"So, what will we do with our current arrangement when I have an assistant here?"

Cindy grinned. "What, no more naked Thursdays in the house? At least you don't have to worry about all those little playthings you had. Most have moved away or moved on. Their lives changed and so did they. We still have Suzanne around at times with her husband, and Jan is still able to play. But obviously, things around here with Katy and I will have to be a little less open."

"That's true. I'll have to be careful when it comes to someone who works for me."

Cindy punched me in the shoulder. "Poor baby. Something might come along."

"Relax, nothing like that is going to happen."

Cindy shrugged. "I know, but I can always hope, can't I?"

"Yeah."

A couple of weeks later, I had completed a few interviews and my favorite so far had been Heidi. I wanted to ask her where she got that name, but refrained during the interview. However, she was the most qualified educationally. She had a Bachelor's degree in English Literature and carried herself very well. She had graduated from college 5 years ago, but not worked since. She quickly mentioned getting married and having a child when I asked why she took so much time off. It was nothing unusual. I called her back for a second interview.

When she arrived, she was dressed very professionally. She was a beautiful woman, 5' 5" tall, with a nice shape and a ready smile.

"Good morning, Heidi."

"Good morning, sir."

"You can call me Dennis."

"Okay, sir."

I chuckled at her response. "Heidi, I want to offer you the position. HR will be in contact with you later today with the specifics. Are you still interested in this position?"

"Yes, sir," she answered enthusiastically.

"And can you start next Monday?"

"Yes, sir."

"You understand the physical arrangements, correct? We will be working most days from here, but will travel to the main office a few days a month."

"Yes, sir. I understand."

"Good, you should hear from HR later today. They will call you and verify some information, and then send to your home email an application and some other documents to complete. Okay?"

"Yes, sir." She then looked down at where her hands were folded in her lap. She seemed concerned.

"Is everything okay?"

"Yes, sir. It's just that I'm worried that my situation will affect what you expect of me."

"Well, what's the situation?"

"I'm a single mother of a 4-year-old daughter."

"Yes, you mentioned that you had a child, but as long as you have childcare of some kind and do your work, that's not a problem."

"Yes, sir. I'm just worried about when she gets sick. Right now, I'm living with my mother, who is providing the childcare. But she may want to go back to work and I'll have problems juggling everything like that. I don't want to mess up and lose my job."

I looked at her. She must not have discussed this much with other women. It was illegal to discriminate against someone before you even hire them because they have children. You couldn't take action unless they ceased doing their job. "Heidi, there are millions of women in the workplace who deal with this every day. We will support you in this and your work. As long as you make the effort, and it appears that you will, things will be fine."

"But you also mentioned that there will be times when we both have to go up to the main office or meet customers, sir."

"Yes, that's true. If something happens during one of those planned trips and you have to miss it, then that's fine. As long as I don't feel that it's a continuing problem, it will be okay. I usually want my assistant there because you will be making all the arrangements for our travel and stay, will be distributing all the materials we have for any meetings, and taking copious notes to type up as a record of the meetings. Also, if we are working on a contract, you will assist the individuals working on our proposal and act as a go-between for me and them. I can do that once in a while, but need my assistant there most of the time. Are you still okay with those travelling requirements?"

"Yes, sir. I can do that."

"Okay, then. We are going to be fine."

Heidi smiled and stood up, extending her hand. "Thank you, sir. I look forward to hearing from HR."

I shook her hand. It was a little damp, probably from her nervousness. "Okay, good. Thanks for coming by again. I look forward to you joining the company."

She left and it left me puzzled about how she brought that up. Surely, she knew that we couldn't hold that against her as long as she kept up with her work. And she never once called me by my name. She kept saying "sir". Maybe she was just getting used to being in the workplace and wanted to be polite. Well, she was smart and well educated when we had discussed a few items I always asked my interviewees. I felt like it was a good choice.

Heidi went to work the following Monday and turned out to be excellent. She organized the space we set aside for the office in the apartment and was always working to improve the work we were doing. She was very personable, but I could never get her to call me by my name. She always called me sir.

Heidi was also always usually wearing very nice clothes that showed off her shape. She wore dresses that accentuated her legs and ass, and her blouses showed that she was fairly well endowed for a small-boned woman. There was nothing slutty about it, just nice office wear that showed she was a sexy woman.

We made one trip up north after a couple of weeks. Everything was still getting settled and my presence was not required as much as the boss initially thought. We were able to do most of our work over email and Zoom.

About 4 weeks after Heidi came to work, and not having had much of a rest while putting in some long hours on a new contract, I decided that we needed a little break. It was Friday afternoon and at about 2pm I closed everything out on my computer and stood up. I wanted to find out some more personal things about Heidi. She had continued to be very polite, calling me sir, immediately responding to my every request, and making sure that I knew all that was going on with the work we were doing. She was very efficient. I just had to find out some more about her. She didn't talk much at all about her personal life. She seemed a bit like an iceberg to me, so much more hiding than showing.

And she also gave all indications of being submissive. In both actions and words, she seemed to me to show that. I didn't want to make any assumptions and it was dangerous to discuss some things with a subordinate, but I had to find out at least a little more about this beautiful, efficient, and educated woman.

"I think that's enough work for today, Heidi. Let's have a drink."

"Oh?" Heidi looked up at me. "Now, sir?"

"Yes, now. We have been working our tails off with all the work coming our way and making sure everything is properly organized because of the move. You've done excellent work, too. It's time for a break."

I walked over to the refrigerator and pulled out a beer. "I'm having a beer. What would you like?" Heidi hesitated, but I could see her looking at the alcohol alongside the refrigerator in this small apartment. "Something alcoholic? Scotch? Gin and tonic?"

"Uh, well, gin and tonic would be great, sir."

"Excellent." I went to the cabinet and pulled out some tonic. "I have a wonderful aromatic Fever Tree tonic here and it is great with gin."

Heidi stood up and came over to me. "Sir, I can make my drink."

I stood back and grinned. "Yes, you can. Go ahead. I'll get out some snacks."

Heidi started to mix her drink, which I could see was going to be rather strong, while I got out some crackers and chips. I knew we had some cheese, too, so I could cut some of that up. Cindy had made sure that I had some munchies in the apartment.

I put the crackers and chips out. "Do you want some cheese, too?"

Heidi looked at what I had placed out there. "Yes, sir. But I can get it."

"Nonsense. Sit and relax. It'll just take a second." She seemed like she thought she had to wait on me. She was my assistant, not my waitress, but she was always that way.

I cut up the cheese and, rather reluctantly, I saw Heidi sit down. She smoothed her skirt down and sat rather primly on one end of the couch.

I finished and sat down on the other end of the couch. The munchies were on the coffee table in front of us. I had a couple and then Heidi started munching on some. I waited a few seconds and then tried to ascertain more about this new employee that I had.

"So, Heidi, you have a 4-year-old daughter. I haven't seen any pictures of her. Surely, as a mom, you have plenty to show me."

Heidi smiled. "Yes, sir, I have a lot of pictures of her. Her name is Elizabeth, but we call her Beth."

"Okay."

Heidi opened her phone and scrolled through her photos. She finally scooted a little closer to me, turned the phone toward me, and started showing me pictures of her little girl. She was adorable. She looked a lot like Heidi and had an amazing smile. I saw pictures of her all dressed up, some from her last birthday, and all the while Heidi talked like a proud mother.

I looked up at Heidi. "She's beautiful." Heidi smiled when I said that. "She looks just like you."

Heidi blushed when I said that. "Yes, she looks more like me than Josh, my ex-husband."

When Heidi looked up and smiled, I said, "Well, you are lovely, so that's a good thing."

"Thank you, sir." She looked away with a small smile.

I got up to get another beer, and took her almost empty glass to make another gin and tonic. She protested that she could do that, but I made her sit while I got the drinks. I made hers as strong as she had, about two shots in the glass.

She couldn't drop the sir, but at least I got her talking a little. She then told me about her mother, who was Swiss and gave her the name Heidi after her grandmother. She told me more in the next five minutes than I ever knew. When she mentioned her ex-husband had moved out to Oregon to be with his family, I asked the question that I was wondering about.

"You never talk about him. I hope he wasn't abusive or anything."

"Oh, no. Nothing like that. We just weren't compatible."

"Okay. So, what about your mother? How long has she been in the U.S.?"

Heidi then provided a brief history of her family and how her mother and father met and married in Europe. She described how they came to settle here and how she ended up here.

At the end of that discussion, her drink was empty so she got up to make another and got me another beer. She was drinking pretty fast for the amount of alcohol she put in the drinks. But, anyway, I told her a little about Cindy and I, but I left out the open marriage and how we did all kinds of things like fake home invasions and other things. She definitely didn't want to hear about that.

I told her more about the history of the company and how I had been there for most of its existence. I had started as an IT technician and worked my way up to VP as the company grew and I proved my personnel and contract-winning skills.

When I finished all that, Heidi got another drink. I was only halfway through my third beer and she was on her fourth gin and tonic. Each one had to have at least two shots of alcohol. I might have to get her an Uber home, if this kept up.

Finally, it was nearing 4pm and I figured she might want to go early. I started to stand, but then she put her hand on my arm.

"Thank you for everything, sir. I really enjoy working for you."

I sat back, a little surprised by her touch. "You're welcome. You've been doing an excellent job. Since you are helping so much on the contracts that I am trying to win, you will get a small bonus every time we win one."

"Really?" She looked up at me and I could see that she was a little drunk. She was starting to look a little woozy. "I love working for you. You are so sure of yourself about everything, and so demonstrative."

"Thanks. I like what I do and I think I know how to do it well."

"You do. I wish my husband had been more like that."

"What do you mean?" She was slurring her words a little and I was wondering if some deep, dark secret was about to be revealed.

"We thought we could make a go of it, but we were too alike."

"What does that mean?"

"After Beth was born, we started having problems making decisions, and we would argue about it, but we didn't even really fight well. We sought counseling." She hiccupped. "Excuse me, sir. Anyway, we went to one psychiatrist who said that the problem with us was that we were both submissive. Neither one of us could be in charge. So, he decided to go live with his mother. I don't even know if he will come back to see Beth."

Did she really just say that? She was submissive? Was it just a slip, or had she really wanted me to know that? She didn't hesitate, but that could be due to the alcohol. Shit! She was looking very delectable, but she was still a subordinate. Maybe I should ask a little more.

"Heidi, you said that the psychiatrist determined that you were submissive. Did they make you take any tests to determine that?"

"Yes, sir. She made us take a lot of tests."

"Okay, well, you look a little affected by the alcohol, so I think I should take you home now."

Heidi leaned back against the back of the couch, her skirt riding up dangerously high on her thighs (and lovely thighs they were). "Okay, sir. Thank you." But she didn't move. I was standing there looking at her and she grinned at me. She put her arms up towards me like a child needing assistance to get up. "I'm ready."

I shook my head. "Okay, here we go." I leaned over and grabbed her hands. I started to pull, but she wasn't helping much. I then leaned over and put my hands under her armpits to help her stand. She giggled and put her arms around my neck. She pulled and I stood up with her hands around my neck and my hands under her arms. That allowed me to get her to a standing position.

"You seem to have had a lot of alcohol in a short period."

Heidi giggled again. "Yes, sir, I have." She was standing pressed up against my front, looking up at me. "Is there anything else sir needs?"

She said that like a real submissive. My cock responded faster than I wanted, but I hoped she didn't feel it. She was still my subordinate. I decided that maybe taking her home wasn't a good idea at that moment. I could imagine her throwing up all over my car.

"Uh, yes. I need you to come in here and lay down for a while. I think we should let the alcohol wear off a little before we get into the car." I turned and, still holding her up by putting my left arm around her waist, lead her toward the bedroom.

"Yes, sir. Whatever you say, sir." She followed along into the bedroom.

"Now, just lay her awhile. I'll get you a glass of water, and then, when you feel a little more sober, I'll take you home."

"Yes, sir."

Heidi turned toward the bed and I released her as she put both hands on the bed. She then crawled up onto the bed on all fours, her skirt again showing me most of her thighs as she was bent over. She then turned to lay down on her side, facing away from me, and her skirt settled up past her delectable ass. I stared at it. She had a perfect small, but bubbly ass, her thong barely visible above it. It was smooth and unblemished. It looked like that of a 16-year-old girl. Well, at least it looked like I remembered a 16-year-old's ass looked like when I was 16 and trying to get them out of their panties.

I went back into the other room and got a glass of water. I took it back in there and she had turned over onto her back, her skirt up around her waist. Her small thong panties were partially wedged into her pussy, leaving her right lip exposed. Damn! I had a boner now. I was going to attack whichever woman I first ran into, Cindy or Katy, when I went back into my house.

I went back in the small living room and sat down. She admitted that she was submissive, and, after seeing her lower body exposed, it was going to be very hard not to make her do all the things that I wanted right at that moment. Shit!

I walked into the bathroom and dropped my pants. I was going to have to pee as soon as my erection wilted a little. I was standing there in front of the toilet when the door from the bedroom opened on the other end of the bathroom. I turned to look and Heidi was standing there staring at my erection.

"Sir, do you want me to suck your cock?"

That was the last thing I was expecting to come out of her mouth, but I was past caring in that moment. My big head was going over all the things that could go wrong having sex with a subordinate, but my little head was screaming 'Suck me! Suck me!'.