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Introduction:

This story is pure fiction. All characters depicted are 18+.

Chapter 5 - Sealing the Deal

An hour later I was in a large office building, sitting patiently in a waiting room. The six chairs in the room were all way more expensive than anything I ever had in my own home, and there was a small chandelier above me. Two flat screen tvs were mounted on the wall, one showing the golf channel and the other CNN. There was an array of magazines on side tables next to all the chairs, and big table against the wall with coffee, bagels, and donuts.

I looked through the instructions that my boss sent me again, making sure that I had all the details memorized.
I had remembered to text Sophia on the way here, asking her to please stay with Julia until I got home, which shouldn’t be too late. She had happily accepted, she really seemed to love babysitting my daughter. They were really good together, and I was happy that she had an older woman in her life, since her mom had left so many years ago.

After some time a tall redhead with thick black framed glasses, a long gray skirt that went a couple inches below her knees, and a green button up shirt stepped through a door in the room and motioned for me to follow her.

I tried to break the ice, “I’m excited to meet Mr. O’Connor.”

“Excuse me?” she stopped and turned in my direction, one eye brow raised in a very confused look.

“Shannon O’Connor, the gentleman I am supposed to be meeting.” I was now as confused as she appeared.

She immediately let out a belly laugh, putting her hand on the wall to hold her up. I just stood there even more confused.

“Did I say something?” I asked mousily.

She laughed a little more and replied, “I’m Shannon O’Connor.” She smiled a big grin at me.

I felt like such a fool. Had I already blown it?

“Oh my! I’m so sorry. I just assumed that you were a he, I mean that Shannon was a guy. You see I had a friend in college named Shan--”

She chuckled a little more, “It’s fine really. I have a cousin named Ryan, and people always assume she’s going to be a man. Its those androgynous Irish names.”

She straightened herself out and continued back down the hall, motioning for me to follow.

I felt like I was walking behind her like a sad Charlie Brown, eyes to the ground. That’s when I really noticed her ass. Even with that thick skirt material it was pushing through, it looked like quite the handful.

We went into her office, it was impressively spacious.

We both sat down, her behind her desk, and she relieved the tension a little, “You know, usually men get to know me first before asking to meet my father.”

Maybe it was the blood rushing out of my head and to my hardening cock, but it went right over my head.

“You’re father?”

“Mr. O’Connor.”

“Oh, wouldn’t that be your husband…?” I don’t know why I said it, it just kind of slipped out of my mouth. I instantly regretted it.

“I’m not married, so Mr. O’Connor is my father.”

“Boy I’m really failing this test huh?” I quipped leaning back in my chair trying to play it off both cool and self-deprecating.

Then she she said, “Well not everyone can have looks AND brains.”

Was she hitting on me, or just being playful?

“So how’d you get so lucky then?” I would have never been so bold, but after what went down (literally!) on the train earlier today I was feeling confident.

“Oh my, are you here to court me or my company?” She retorted, blushing a little and opening up her latop.

“Well they’re not mutually exclusive are they?”

“Oh look, he does have a brain after all!”

We bantered back and forth like that for a little interspersing some business talk here and there.

I quickly realized that she wasn’t the one who I was going to be giving the presentation to. I think her job was just to feel me out, see if I was a bullshitter or not, if I -and by extension my company- was someone that they had chemistry with, you know, could do business with. That realization made me a little bummed out, I really thought that she liked me, but I think she was just supposed to roll with whatever personality walked through her door, and then later give her conclusion to her higher ups.

She explained that I’d be giving a presentation to a group of executives around 3pm, and that I had a little time before then if I needed to go grab a bite to eat, or get any work done. She said there was a spare office where I could find some quiet if I so needed. Then she thanked me and wished me luck.

I felt thrown out. Did I blow it with her, did I blow it with the company? I’m no salesman, I was only here because of the two salesmen the company had one was busy with a bigger client and the other was terribly ill, and my boss didn’t want to make them wait, since they were potentially new clients, he wanted to make a good frist impression. I might have just undermined that.

As I was almost out the door and she was already deeply engrossed in whatever what on her computer screen I reeled around and said, “Excuse me?”

She looked up a little surprised, “Yes?”

“I just wanted to let you know that I’m not actually a salesman, and I;m sorry if I’m not making the best impression. One of our salesmen is out of state with an important client and the other guys is terribly ill, but my boss really wants to work with you all and he sent me along because I’ve been working there for a long time now, in many different departments and I know our product better than anyone else. So I’m sorry if I made an awkward first impression.” Where was the confidence I has walked in the building with? I felt like my old shriveled up self.

She nodded her head and replied, “Well I thank you for coming all the way out here despite that not even being your job, you clearly are a dedicated employee. And your company must be pretty good to foster such dedication. Also I appreciate the honesty and how forthright you are. Again, I wish you luck with your presentation.” then she went back to her computer.

I couldn’t tell if what she said was a pat on the head good job kid here’s a trophy for attendance, or if she actually was impressed. I figured I’d go find that quiet spot to relax and prepare.

It was shortly before three and my phone vibrated. I looked and it was a text from my daughter. She was probably just telling me that she was home from school. She did that if Sophia was running late.

Just as I clicked on the message to see it a balding old white guy in a blazer appeared in the door way.

It was a picture message.

“The boardroom is now open…”

The picture was a selfie. She was standing in front of her bedroom mirror, wearing a yellow tank top and Hello Kitty panties. They were white with the kitty’s face on them, and the word Hello above its head.They had a purple border and the elastic band was extra thick.

“...if you’d like to get set up so that we may start on time.”

The text of the message just said, “I bought these today after school, with some money I found in your room. I hope you’re not mad, but I needed new underwear, many of mine have gotten pretty old.”

My jaw dropped, and I looked up at the man greeting me. “Oh, um, ah, yeah, uh, thanks.”

He stood there looking at me.

My phone buzzed again. This time it was just a text (I found myself thinking “Thank God”).

It read, “You always wanted a kitty but I was allergic. I’ll let you pet this one, I swear. ;)”

My head shot up, eyes darting toward the older gentleman who was clearly trying to figure me out.

I said nothing and just started to pack up my things. I had nearly everything in my suitcase when my phone went off again. I immediately looked at it. It was another picture message.

It was a close up of her crotch. One hand was pulling her panties to the side, exposing her mound, which was still trimmed very short. The text read, “And look! It’s a short hair! It won’t shed as much! =)”

I nearly lost it.

She sure knows how to flirt/drive a man crazy.

The old man started to nod and smile, “Ah, is that the little lady?”

What the fuck?! How did he know?!

“The uh--?” was all I could mutter.

“Yeah, you know, the old ball and chain?” He smacked me on the shoulder.

“Oh yeah! Right. Yeah. It’s my little lady for sure.” I stammered in response.

He showed me the board room and left.

I quickly got back on my phone and sent a reply, “Sweetie I’m about to be in a very important meeting, giving a big presentation. I can’t really talk right now.”

Then I got everything all set up, they had a computer connected to their projector so I set up my slideshow on there, and then got my laptop out for my notes.
About a dozen people filed into the room and took their seats. Most of them were graying old white men, but there were a few women and younger people in the mix. Just as I thought we were ready to get started Shannon walked in and sat down at the end opposite of me, so that we were both at the head of the table. She set her laptop down as well and was obviously looking for something. when she found it she started to talk.

She introduced me and then proceeded to explain what my company does and why I was invited here to speak to them.

While she was talking I got a new email.

It was from my daughter.

It was a picture of her blowing me a kiss.

I closed the email and looked up. Shannon finished talking. I thought I was about to start but some guy asked her a question. She responded, but then he went on some long explanation, that I could tell from her eye-rolling was either irrelevant or off topic. I had the jitters, I felt totally exposed and uncomfortable given the messages my daughter had just been sending me.

I looked down and there was another new email. I almost didn’t click it, I wasn’t really sure why I did, but the subject line said “good luck!” There was no picture, just a short sentence, “Don’t be nervous. Sorry about earlier. You can do this.After you nail this out of the park lets go out and grab a bite to eat tonight, what do you say?” I felt guilty. She was just trying to have some fun. She didn’t know what I was going through. My heart warmed up and the thought of my beautiful baby girl and how much she really loved me.

I quickly replied, “Thanks. That sounds great. Just a bite to eat, or do you want to stay up late having fun too?” Then I close the e-mail program, and just in time.

I gave the presentation, and answered all the questions, I think sufficiently well, but they were a hard crowd to read. After it was all over I thought maybe I’d get a round of applause or something, but I don’t really know how this stuff works.

Instead, they just asked me to step out into the hall for a moment, they need a minute to talk.

I left my things where they were and stepped out. It was so quiet in the hall that I could actually make out most of what was being said in the boardroom without me. The consensus seemed to be that I impressed them and they wanted to do business. The only one who had a strong negative opinion to voice was Shannon.

“Well, if I may be frank. I had the chance of speaking to him earlier, and I’m actually skeptical. I just don’t know if they are the right fit for us. I definitely don’t think we should take their offer without negotiating. And I don’t want to negotiate with someone I barely know who didn't make a strong impression with me over the phone. I think we should ask him to stay here tonight and we can meet with him in an AM session tomorrow and see if we can bring their offer down some, and what kind of sweeteners they can offer.”

What. The. Fuck.

So close yet so far.

I knew I fucked things up earlier.

If my boss found out we lost this client because I was hitting on their external VP he’d chew me up and spit me out. I might even get fired for something like that.

They opened the door and thanked me for my time. Then they asked me if I would be able to stay in town for the night and meet them at 10am for one more round of discussion, they said they still have a few things to clear up and that they’d really appreciate it. I accepted of course. Then I packed up my things while everyone filed out.

Shannon was the last in the room, she came over to me and handed me her business card, and I gave her mine. She thanked me for her time and then left. It was all very business.

A little while later I had found a hotel and told me boss (some of) what happened, mostly the stuff I wanted him to hear. I was very optimistic and she was happy to see me taking initiative by agreeing to stay out there, and told me that if I get this for him, it’ll be a very sweet bonus.

After I hung up I saw I had another text. I was expecting it to be my daughter. It was from a number I hadn’t put in my phone yet. I looked at the business card Shannon gave me, it was her.

It read, “So do you still want to do dinner, or do you just want to come over my place and order pizza, and then get to that fun you were eluding to?”

I dropped the phone, and I think my jaw hit the floor as well.

I quickly opened my laptop and checked my email. Sure enough, the message I had received earlier that I thought was from Julia, had actually been from Shannon… I just stared at the thread:

>>“Thanks. That sounds great. Just a bite to eat, or do you want to stay up late having fun too?”

>>>>>“Don’t be nervous. Sorry about earlier. You can do this.After you nail this out of the park lets go out and grab a bite to eat tonight, what do you say?”

She had thought I was nervous because of her. She had no idea that my daughter has basically been sexting me right before the presentation. And she apparently did like me because not only did she ask me out, but her more recent response sounded more like a booty call than a date.

Sometimes things have a way of working out.

A couple hours later I was at Shannon’s penthouse apartment ringing the doorbell. She opened the door wearing a sexy green dress that hugged her wide hips and large breasts, which I hadn’t really noticed in her business casual attire earlier. He long flowing hair fell down to her spaghetti straps, and her sexy legs were adorned in fishnets, and she was wearing high-heels. Behind her the apartment lights were dimmed and slow jazz was playing, also I thought I smelled candles.

Before I could say anything she grabbed me by my tie and pulled me into the apartment, slamming the door behind me. She pushed me into the wall and we just started making out, running our hands all over each other.

We sloppily kissed each other while doing some heavy petting. Her ass was really firm and her breasts were amazing. She had her hand on my cock, rubbing it through my pants, her other hand on my chest.

She pulled away so we could breathe, and said, “How about we let him out, huh?” And she grabbed my hand and walked me over to her couch, which was full of throw pillows. I sat down and she got on her knees between my legs. She rubbed me a little more and then unzipped me and freed my cock.

“Oh my!” She said, and proceeded to envelop my meat in her warm wet mouth. She was totally lost in what she was doing and I couldn’t believe it, she was the second person to suck my dick today. When it rains it pours, they say right?

My phone vibrated. I wondered if I should check it.

I sneakily pulled it out and looked at Shannon. She was sucking away, paying no attention to my hands or the phone in them.

It was one of those short video messages, and it was from my daughter.

She was coming up from behind the babysitter Sophia, who was totally unaware. She pointed the camera down Sophia’s cleavage, showing fuller breasts than I thought she had. Then she reached around with her other hand and grabbed one of her boobs and yelled “BOOBIES!” and Sophia recoiled and yelled, “Hey!” and the video ended there.

Holy fuck, that was hot. Watching my daughter sneak a down-blouse for me and then grab another woman’s breasts, all while Shannon was going to town on my cock and balls.
A moment later it vibrated again and this was of the two of them wrestling on the couch, Sophia was yelling, “Give me that phone, you!” and my daughter had her in a hold. Then she flipped the babysitter over and pointed the phone at her ass, which she then slapped real hard. This also made Sophia jump. I thought the video would end there, but Julia then pulled the back of Sophia’s shorts down, exposing her nice ass. Then it ended.

Shannon was going real hard now, and I felt on fire with lust. Somehow she didn’t seem to notice what I had been doing -- I had kept the sound on the lowest possible setting and was watching it right in front of my face, so she probably couldn’t hear it over the sound of all that sucking.

I grabbed her and motioned to move with me. I stood up and pulled my cock out of her mouth and told her to suck on my balls. She put them both in her mouth and rolled them around on her tongue. I pumped my throbbing meat and got real close.

Shannon let go of my balls, and ran her tongue along my taint. That pushed me over the edge and I grabbed her face and began to cover it with my cum. A few bursts ended up in her gorgeous red hair. But I didn’t give her any time to clean herself off. I scooped her up and slung her over the side of the couch and spread her legs.

She wasn’t wearing any panties. Good girl.

I brought the bloated head of my over stimulated cock to her soft wet entrance and eased my way in, I could feel her slowly widen for me, and eventually I was fully inside. Then I just fucked her brains out. I slammed into her, and she was just screaming in sorts burst of “ah- ah- ah- ah- oh- ah- oh”

I had been fucking her doggy style for a couple minutes when my phone vibrated again. I looked back at it. It was within arms reach. With my left hand I grabbed Shanon around the waist real tight, keeping us together real hard, and with my right hand I reached back and grabbed my phone.

It was another short video.

It was just a close up of a beautiful trimmed little pussy. But then a finger entered it and thrust back and forth. It continued to do so for the rest of the video.

What a sexy little thing, sending me videos of her masturbating…

Or.. wait…

No.

Was it?
It was too zoomed in to tell, but the fingers were coming from the wrong angle. If she was masturbating then wouldn’t I be seeing the bottom of her hand, not the top?

Was my daughter finger fucking out baby sitter? And did she just send me a video of it?!?!?!

I dropped the phone and grabbed Shannon’s hair and fucked like an animal for another couple minutes just thinking of my daughter finger fucking her babysitter.

When I was close I moaned, “I don’t have a condom…” It was more of a question than a statement, and she knew what I meant. I wanted to know if she was on the pill or not.

“Just put it in my ass.” She commanded.

Who was I to argue?

I pulled out and spread her cheeks real wide and plunged my steel beam of a dick into her ass all at once. I got as deep inside of her as I could in one thurst. She let out a scream of both pleasure and pain and I emptied my balls. Waves of pleasure ran over my entire body and I could tell she was also having a full body orgasm.

Eventually she was laying on the couch, head on my lap and she looked up at me and said, “By the way, you got the account.”

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