Pleasing Debra The Boss

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 Marshall was the last name of her former co-owner, Douglas Marshall, but he has since retired and been replaced by his gorgeous daughter Debra.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.

Over the course of the next couple of hours we didn't converse much. I just worked on my speech some more while she was making calls to people setting up appointments for later in the night. Once 4:30pm came, we were both ready to go and represent the company. I was excited and so was she.

* * *

Delivering The Company Sales Pitch 5pm

I was wearing a black suit with a red tie because Debra was wearing a red business suit.

A few minutes before our speech, Debra pulled me aside: "When you're done the speech and you walk over to me, I'm going to kiss you. Just kiss me back and make it natural." I wasn't sure if her change of plans would work, but I said it was cool.

I did the speech about how our company was owned by two women and employs mostly women, except me and one other guy, who doesn't like women, so it makes me a lucky guy. People laughed at that joke. I talked about our strategies working with companies that work with women and how we know that even though "sex sells" is a phrase that people use a lot, there's a more to women than that.

My speech spoke about women in a positive light. I got the whole crowd laughing at times, I even interacted with a few of them and I could see Debra was impressed by my talking skills, which I've always had. She was a tough woman to please, but she was definitely smiling while I was up there.

I wrapped it up like this: "We at Willis and Marshall Advertising want your business because we know what's good for the consumer and we want to help you get it to them. Because at WMA, if you're not happy then we're not happy and we sure like being happy. Thank you."

Most of the people in the room gave me a huge ovation. I walked to the back of the room where we were seated and Debra gave me a long, wet kiss. Wow. I was stunned that she did it, but I was all in for it too.

DM: "That was fucking amazing. You absolutely killed it and I'm so proud of you."

About five minutes later, one of the women from Victoria's Secret walked over to us asking if we could give them a pitch because they feel like we could do a great job with one of their new lingerie lines. Debra had this huge smile on her face.

JW: "Wow that's incredible. We would love that."

VS: "To be honest, we loved the speech and it's really just a matter of working out a financial agreement. We definitely want to work with you as soon as possible."

Debra looked at me, then I looked back at her and smiled.

DM: "We would love that. We'll be here for four days, so whenever you're ready."

VS: "How about 9pm tonight, I'll get some papers drawn up and we'll meet in the restaurant here in the hotel."

DM: "Sounds great. We'll be there."

She shook both of our hands and was about to leave. Debra had another question.

DM: "If you don't mind, can I ask what sold you on us the most?"

VS: "It was him." She pointed right at me. "This business is full of a lot of bullshit, but that speech was very real and spectacular. You have a winner right here, Miss Marshall. It's not my business, but he probably deserves a raise."

I was probably blushing as she said that. Debra just smiled at me with a look on her face that I had never seen from her before, but I have seen it from other women that were attracted to me. It was as if she was looking at me in a different light now.

The presentations lasted another half hour or so. We got out of there by about 7:15pm when she told me she wanted to go to the room.

* * *

Hotel Suite 7:20pm

We had a little over an hour before we had to get to that meeting. I walked in the room and then Debra did. She locked the door behind her.

"Want to prepare for this meeting?" I asked.

When I turned around she was unbuttoning her red jacket one button, then two and she said: "Nah. We're ready. I want to celebrate right now." She undid the final two buttons on the jacket to reveal a black bra covering her massive tits that looked so familiar from her WWE days. She tossed the jacket down.

She walked over to me and started to undo my belt buckle. "I'm not a man hater," she said while taking off my belt. "I just haven't been lucky, but when I see you I look at somebody that can offer me a lot in the boardroom and the bedroom." She took off my pants while I took off and tossed my jacket down. Then she slowly unbuttoned my shirt. "You impressed me a lot. Our company needed that so much and now I want to show you my appreciation." She turned around, so I undid the zipper on her skirt and took it off.

After tossing my shirt off, we kissed passionately. I was in my boxers while she was in her black bra and panties. She was rubbing my abs while also reaching for my cock. She told me to sit back in a chair.

"It's time to let the puppies loose," she said referring to her tits. I kissed her on the lips some more, unhooked her bra and put her massive tits in my mouth. I sucked on the nipples gently while she moaned in pleasure. She was smothering my face with them while I was doing my best to support them with my hands while also kissing them. As I was doing that, she was rubbing her body up against mine to get my dick harder. It was really hard because I wanted her so bad.

She got off of me and then reached into my boxers. She yanked them down quickly so that my massive, erect dick was looking right at her.

She was on her knees in front of me rubbing my dick: "I bet you wanted this for a long time, huh? The 'Ice Queen' on her knees in front of you like this? Consider this part of my thank you."

I laid back as she went to town on me, sucking on my dick by going up and down on it very quickly. She went fast to get it hard, but then slowed it down to savor it. I was moaning in pleasure: "What a thank you this is!"

She just smirked at me while continuing to suck my cock. She used her hands to rub my balls too, so I was in heaven while this was going on. Every once in a while she would take her mouth off my cock, but most of the time she was all over it. She did amazing and it lasted for like ten minutes.

When her mouth was tired, she shoved her tits onto my cock and sat upright while I stood up to start titty fucking her. The "Puppies" loved it as she shoved them together while my shaft went up and down across her tits. The titty fucking went on for a few minutes when I could tell she was getting tired a bit.

She smiled at me: "Why don't you stick that cock inside me while I think about that raise of yours?"

I wasted no time as I scooped her up in my arms and carried her over to the bed. I laid her on her back while yanking off her panties. I mounted her, then slowly rubbed her clit with my hand to feel how wet it was while I also kissed her on the lips.

I spread her legs apart, then thrusted my dick into her pussy and she moaned in pleasure right away: "Ohhhhhhhh fuck yes!" I was deep inside of her as I pushed forward with my hips to get inside her as much as I possibly could. She kept moaning, yelling "yes" repeatedly while I

"You want more of this," I told her while fucking her hard. "Give me that raise and it'll be yours all day every day." I was really getting deep inside of her, feeling how wet she was and could tell she was loving it. After dealing with her being a bitch so long, it felt so good to pleasure her like this and to get to see this side of her.

After a few minutes of fucking her, she kinda tapped me on the leg suggesting that she needed a break.

"All day, every day huh?" She smiled as I took my dick out of her and she rubbed it. "I like the sound of that."

I laid down on my back as she sat on my face with her clit on me. I rubbed her pussy with my fingers, got her really wet and started to eat her out. She was moaning again.

She was panting as she spoke: "Oooooooohhhhhhhh fuck yes! Get deep inside me, feel how wet I am for you! Oh fuck...fuck..."

I encouraged her to suck me off some more in the 69 position: "Suck my dick, boss. You know you want more of that!"

She leaned down and stroked my cock again: "Keep calling me, boss. I like that...a lot."

As I continued to lick her clit, she leaned forward and put my dick in her mouth again. I slowed down the pace of the clit licking a bit because she was really into the cock sucking, even more this time. Her blowjobs were amazing! I decided to encourage her some more.

"Oh fuck yeah Debra, you know how to treat an employee. You're the best boss ever!"

"Fucking right I am," she said as she went back down on me.

I kept on licking her pussy, feeling all of her juices and she was sucking me off amazingly well.

I complimented her again: "Money's good, boss, but this is better than any dollar figure that's for sure."

She got off my cock a bit to say this: "Oh you'll get that raise, sugar...I just want more of this in the office."

I assured her: "I have no problem with that!" She got off my dick while I stopped licking her clit.

As we both lay there on the bed exhausted, she had a big smile on her face: "That was quite the negotiation, huh?"

"Yeah," I told her, "but we didn't negotiate price."

"You're right," she said while smothering my face with her tits. "Lie back. I want to be on top for this negotiation."

I went back to the headboard of the bed so my upper body and back was up against it. Debra crawled on top of me with her clit by my dick. She held my dick in her hand, then mounted me so that her face and tits were above me.

With my dick inside her she rubbed her clit against it and then leaned down to stick her tits in my mouth. It was an amazing feeling. After about 30 seconds of sucking her tits, she leaned back a bit.

I smirked: "Is this a negotiating tactic?"

She was panting in reply: "It is whatever the fuck you want it to be. Just don't stop! Don't fucking stop!"

She kept on riding me going really fast. I could feel her body tighten as I went deep inside her.

"What kind of raise do you want?" She asked.

"I'll take 30% of what I currently make, plus I want to be able to fuck you in the office."

"Damn right you'll fuck me in the office!" She kept on riding my cock while breathing heavily. "How about 50% raise and you move into my mansion so we can fuck a lot more often."

I wasn't sure about moving in with her, but the sex was great and it would save me money if I sold my place, so I told her it was fine.

"That works for me," I told her. "So how do we sign the deal?"

She tapped me on the leg again so I could stop: "Cum in my mouth. That's the deal."

She got off of me, then I sat up the bed and I shot a load of cum into her mouth. She swallowed most of it.

As we lay there exhausted beside her, she looked over at me and simply said: "Best business meeting ever."

"You damn right, boss."

Feel free to email me with any thoughts or comments that you may have on this piece.