This story takes place in February 2003.
My name is James Willis. I'm a 28 year old former model that's a recently graduated Marketing MBA student from Richmond, Ohio that has been living in San Mateo, California working for my aunt's advertising company called Willis and Marshall Advertising. Marshall was the last name of her former co-owner, Douglas Marshall, but he has since retired and been replaced by his gorgeous daughter Debra. She is a big breasted former WWE diva who I was a big fan of from the wrestling world, but she has since transitioned to working in business.
From the moment I got there I knew Debra wasn't a big fan of mine. For one thing, our company had only ten employees, eight of them were women and the only guy there other than me was this gay dude named Carl. The focus of the company was to work specifically on the advertising of women's products, but my aunt Helen felt I was qualified enough to work for the organization. The first time I met Debra she specifically told me she would be watching me closely and made note of company policy that meant no dating fellow employees. I was cool with it.
Two months into the job, I was doing just fine. Then in mid-February I was informed by Debra that she and I would be flying to Las Vegas for an Advertiser's conference with yours truly being required to make a speech. I didn't really ask Debra why I had to speak, but I asked aunt Helen. She told me either she or Debra had to go, but she wanted Debra to because she was single and wasn't tied down. All I knew about Debra's personal life was she was married twice to a former football player and wrestler, divorced from both of them, thus giving her a lot of money and she was, as I was told by my other co-workers, a "man hater." She simply hated men. Knowing all this made me even more attracted to her.
The conference would be held from March 12-15 and would be considered work days. Even though she was a bitch to me, I was very turned on by Debra. She's older than me at 36 years old, but she's very bright and gorgeous. Plus, I watched WWE a lot when she was booked to be one of the sexiest women in the wrestling business. She had blonde hair, blue eyes, a big rack that's like 36DD and a great set of ass and legs on her too. It helps that she wears skirts every day, often times she'll wear short ones. As they say, it's great seeing her, but it's good to see her walk away too.
* * *
March 12 - 10am on the plane to Vegas
I met Debra at the airport. The flight to Vegas was only like an hour and I was interested in talking to her in that setting. When I got there, Debra was in this black business suit. It had three buttons up top with the top one undone showing a little bit of cleavage. Her skirt was pretty damn short, which is not something I was going to complain about.
She got us first class tickets. I had never sat there before, so that was cool. The conversation on the plane was pretty interesting. We talked business for a few minutes, but then I asked her why she was always so bitter towards me.
DM: "I'll admit I've been tough on you. As you know, we don't hire men outside of Karl and I was hesitant about bringing you on board. Your aunt insisted, so I let it happen. The way I see it, this event here is a make or break time for you. It's your chance to shine. Either you make the most of it, or you don't. It's up to you."
JW: "Can I ask you an honest question: If it weren't for this conference where a man was required to speak do you think you would have agreed to hire me?"
DM: "I don't know. This is an important conference for us, though. Helen has confidence in you and despite what you may think, I do too. With that said, there's a lot of pressure on you during this trip. I hope you're up for it."
After I assured her I would be okay, she finally asked me some specifics about my speech.
JW: "The main focus of the speech will be on the three things we as people want in life: power, money and sex. I know it's a little controversial and may surprise some people, but I trust that it's a topic that will fit well with this group that we're going to be talking to. I want us to be a cutting edge company. I want to expand what we are to reach a wider group of people and for that to happen we have to take some chances at events like this."
DM: "Ooh, I'm impressed. I like your line of thinking, James. It could definitely work. There are a lot of power players here, big companies that we can reach to with this line of thinking. I know Victoria's Secret will be there, we've come close to landing a deal with them in the past, but it didn't happen. I'm hearing they are open to just about anybody this time. That's a company I'd really like to have under our tree."
I assured her I would do everything I could to get us that success. Then we started talking about some personal things. I was a bit surprised by it, but it gave me the confidence that maybe she didn't hate me.
DM: "Can you be honest with me and tell me what the other girls think about me? I get the sense that the majority of them don't like me."
JW: "You're a tough boss, Debra. I don't know how to say it other than that. It's hard for people that work under you to carry on a normal conversation about life when you're their boss. They're afraid to say something that may upset and could lead to them losing their job. You definitely have their respect, though. Don't question that. We all know how hard you work and that's why we're all so willing to work hard for you."
DM: "What about this man hating thing? I heard somebody say that about me. They think I'm just some bitch, right?"
JW: "Again, it's not easy for any of us to just come and ask you some personal questions. Then when I got hired you told the girls they couldn't date me and that was fine, but I think that and a number of other events have made them feel separate from you."
DM: "I know I can be uptight. When we first hired you the girls learned about how you used to model, they googled your name up and were looking at your pictures."
JW: "Really?"
DM: "Yeah, so I told them to stop and get back to work, then they were all bitchy toward me."
JW: "What did you think?"
DM: "Of what?"
JW: "The pictures? Did you like 'em?"
DM: "They were very good. You're a handsome man, no doubt about that. I used to model a bit. I won a teen beauty pageant in Texas when I was growing up and I almost pursued that career. Then I married a rich guy when I was young, it was a horrible relationship, but I went and got my education, did that wrestling thing for a few years and now I'm doing pretty well for myself."
Just before the plane was about to land, the pilot came on to announce ten minutes to go, Debra asked me for a favor.
DM: "So you know, there's just one room for us. There's a king sized bed, then a smaller one in another corner that one of us can sleep on. A lot of men like t o hit on me and things like that, so it makes me real uncomfortable. Now since you're new they don't know you and I was thinking you could pose as my lover, boyfriend, whatever to help me with that. Could you do that for me?"
JW: "Yeah, I mean I said I would do whatever you needed of me and I meant that. Just what about the whole 'not dating co-workers' thing that you're so strict about at the office?"
DM: "We're not at the office now, are we? Nobody back there has to know. What happens in Vegas, stays in Vegas, ya know?"
JW: "I got it."
DM: "So if I kiss you, you kiss me back. If I hug you, you hug me back. If I hold your hand, you hold mine. I'll determine when it's the right time, okay?"
JW: "You're the boss."
Our plane landed at about 11:00am, we got our bags, hopped into a cab and made our way to the Marriott hotel in Vegas, which was the hotel where I'd be doing my speech later that day at 5pm. On the way up the elevator, Debra told me to hold her hand as we walked out just in case somebody was around to see us. She knew that if somebody saw her with me they'd leave her alone for the week. I obliged and frankly was eager to do it.
