Managing Expectations

It's not that I didn't understand her, I do pride myself on having a vocabulary. I just didn't understand why she said it. So to clarify I asked, "What?"

"Take off your shirt."

The apartment wasn't particularly warm, but that comment raised my temperature. As I often did when faced with an uncomfortable situation I stalled and attempted a joke. "Maddy I haven't really been hitting the gym lately, and I'd hate to inflict that kind of punishment on you." I didn't really look that bad, by the way, although I certainly didn't have anything resembling muscle definition.

She sounded disappointed in me for the first time that evening, "You have a job in advertising but you can't advertise yourself."

I still had no idea where she was going with this. I was wondering if she might have been drinking before I ever walked in the room. Maybe she was just high. Whatever it was, I could see she was serious. I stood up and took off my shirt as nonchalantly as I could under the circumstances. I set it on the back of the unused chair and turned to face her.

The approval returned to her voice. "Not as bad as you made it sound Ben, not bad at all really. You undersold yourself. I do wonder what else you might be underselling."

I just smiled. I guess I'd passed some kind of test. I gamely tried to redirect the conversation back to the reason I was here. "Well with more time off, I could definitely start working out and addressing some personal improvement." I was impressed with my ability to stay on message... for about two seconds.

She waved her waved her dismissively. "Now the rest of it."

This was not even close to matching any scenario I'd considered when imagining this conversation. I was now very uncomfortable. "The rest of it?"

"I seem to have to repeat things before you get them Ben. Do you really not understand what I am saying? The rest of it."

"I'm sorry Mrs. Fairbanks. I guess I should be going. I'm a happily married man and I must have given you the wrong impression. I won't mention this again. I was hoping for a serious conversation about my prospects but whatever this is, well I don't know what this is but it obviously isn't that." I reached for my shirt intending to put it on and exit without even buttoning it. I just wanted to get away from a weird situation I didn't understand.

"Oh it's a serious conversation. You walk out that door it's your choice. When you do though, you leave any future goodwill from me in this room." It wasn't threatening but there was steel in her voice. It was a voice that communicated that there were high stakes for either decision I might make.

I didn't put on the shirt. I was trying to comprehend what she said.

She just looked at me. "If you're going to go, go. I'm sure you can have a lovely conversation with your wife."

That decided me. There was no way I wanted to have that conversation. At that moment I remembered Belinda's words, "You do not leave that room without having given it your absolute best."

I moved in front of her and started clumsily removing the rest of my clothes. It's difficult to remove socks standing up but I was now fully committed. I managed to remove everything but the boxers. She never said a word while she watched but the smile had returned. She was clearly pleased, I just wasn't sure exactly why. I paused when I got down to just my plain red and white boxers and looked at her. I was wondering if by "the rest" she really meant all of it. She just continued to look at me and drank more wine.

I took that as an answer. The boxers joined the rest of the pile on the rug. She made a circle with her finger and said, "Turn around. Let's see the rest of what you're selling."

I turned my back to her and waited. In case anyone is wondering, I definitely didn't have anything close to an erection. "Erotic" was not the first word that came to mind describing how I was feeling. "Humiliation" was a lot closer.

"Nice ass. That wasn't obvious from either your pants or those boxers. For someone in advertising you certainly don't put a lot into your own presentation. Turn around."

I did. Her words seemed like she was doing more than just taking a shot at me. It was like she was trying to be helpful. I was going a bit nuts trying to figure out exactly what was happening and how things had gotten to this point. She pointed to the other end of the couch.

"Grab your glass and join me. Let's continue our discussion."

Fully naked, I grabbed my glass of wine and joined her on her end, my flaccid penis clearly in her field of view. Her eyes didn't linger there, thank God for small favors. I'm a grower, not a shower. I took a big swallow of what was still in my glass. I felt like I might need the whole bottle by the end of this conversation, if that was indeed what this was going to be. She raised her feet as I sat and placed them on my lap.

"My heels might be a bit hazardous. Why don't you be a dear and remove them?"

I set my glass down and worked on separating her from her expensive footwear. After I put them on the floor, she kept her feet in my lap. In a way, I was glad for the covering. I felt a little less naked.

"That's better. Heels can be rough on the feet. Do you give a decent foot massage?"

"I've never had any complaints," I said as I started to massage one of Maddy's feet. At this point, even I was smart enough to know that I didn't need her to come out and request one.

She let out a contented noise as I started working, "Oh that feels great. You keep doing that while I talk. You've told me why you want a promotion, so allow me to give you some feedback."

I kept massaging and just said, "Okay." At that point I felt fewer words were in my best interest while I tried to wrap my head around this turn of events.

"It sounds to me like you came into this company with certain expectations. I'm gathering your wife also shares them. You do good work, you are timely and responsible and you've put in a lot of hours. You seem to feel that if you did all of those things, that a promotion should naturally follow. You feel you deserve it and want it because you have life goals that you are working on."

Everything she said seemed accurate. I just remained silent and started working on the other foot. Based on her body language, I felt I was giving a pretty decent massage. I did actually undersell my ability in that area; I'd often had Belinda drooling at the end of one of mine. An unfortunate side effect of being in contact with Maddy was that I once again felt that treacherous bastard waking up.

Maddy made another contented noise, took another sip of wine and continued,"You've looked at management from your point of view. You mention you are 'well liked' as an asset. That is certainly an asset when working as part of a team or meeting with clients. It can be a liability once you get into management. I am very effective at what I do and I'm certain you aren't sure how you feel about me at this moment."

That was an understatement. I just kept rubbing her foot, perhaps a tad harder than I had been. Part of it was passive-aggressive behavior; the other part was growing discomfort with my stiffening member.

"Oh yes. That's the spot. Keep doing that." She drained the remainder of the wine in her glass. "So what we look for as management material is not the same skill set we look for in other areas. You've managed to raise some red flags during this trip, as well as shown some potential. Could you be a dear and refill my glass?"

I carefully removed her feet from my lap to stand up and get the bottle. I look down and sure enough, the little bastard was semi-erect. No way I was hiding that. I got up, got the bottle and poured her another glass. I took the opportunity to drain my own and refill that one as well. Then I sat back on the couch. Her feet resumed their place on my lap.

"Thank you, Ben. Oh, don't stop rubbing. Now I'd like to hear from you. Why do you think I'm humiliating you like this?"

That was another sharp left turn. Well, at least I learned she wasn't crazy. She was aware of how I must be feeling. I thought about it. There was clearly a right answer.

"Don't stop rubbing."

I'm a terrible multi-tasker at times. This was not the time to be that guy. I resumed rubbing. "You want to see how serious I am about this. You want to see how I act under duress. You are testing me to see if I can handle the pressures that come with management." I hoped I was right.

She let out another sound of pleasure as I worked a spot on her left foot. "Bravo Ben, you're almost there. Not quite though. There's also a bit of a personal reason as well. I won't make you guess."

That was good because I had no idea what that could be. I hardly knew her.

"When you knocked on my door unexpectedly you put me into an embarrassing situation. I realize you don't know this about me, but I love my family, and that includes my husband. I answered the door expecting it was room service, since Jeff had just ordered some champagne. Imagine my surprise and dilemma finding you there, unannounced and clearly aware of who I was with. It's certainly not something I'd ever want getting back to anyone."

So that was it. She was not as unperturbed as I had hoped. "I'm sorry Maddy, it was impulsive. I do understand, I also love my wife. I'm not a gossip. I also wouldn't want to do anything to damage my happy marriage." I felt like I was tiptoeing through a minefield. I hoped I was being diplomatic enough. I omitted the part where I couldn't ever imagine cheating on Belinda. What was happening at the moment was uncharted territory for me, and I really didn't want to think about it.

She was drinking from her second glass of wine. "I sized you up pretty quickly. I felt that what you saw wasn't going to go anywhere. I suspect you didn't even tell your wife."

She was right again. It's normally the kind of thing I would tell Belinda. What had kept me from doing that was my concern she'd think I'd blown the promotion, not to protect Maddy's privacy. I wisely just said, "I didn't."

"I thought so, but I'm still glad to hear you say it. I assume this will remain a secret you can keep."

"It will." I meant it, too. There was no way I could tell Belinda that without also telling her about this, and there was no way I was ever going to tell her about this night, even if it ended in the next minute. As it turned out, ending soon was not something I needed to worry about.

"Good. Now that you have felt the same sense of embarrassment I felt that night, let's see what else you have learned. You're a quick study. Let's see if you have the rest of what it takes to move up."

It felt good to hear that. Whatever else was going to happen, Maddy had gotten her pound of flesh. I wasn't going to be further compromised. I was wrong.

"You give a great foot massage. A woman could get used to that."

"Thank you. I actually enjoy doing it." I enjoyed doing it for Belinda, but certainly this one was under duress. It was still nice to know I could perform under unusual circumstances.

"You can tell when someone enjoys their work. Reach under my dress and pull down my panties."

Smack! There it was again. As soon as I felt I knew where things were going I was thrown off course again. By this point I had eliminated "What?" from my vocabulary, and without hesitation I reached under her dress worked my hands up to her panties. I was careful not to raise her dress on her legs too much, since it seemed she wasn't ready to show everything. That also worked for me.

She shifted on the couch, enabling me to slide them down her legs. They felt soft to the touch and what I pulled off was a black silk pair that just screamed expensive. I imagined her bra constituted the other matching half. My erection was definitely noticeable now and was clearly on prominent display when she returned her feet to my lap.

"Why do you think I just asked you to do that?"

"You want to see if I'm a team player?"

She laughed. "That's part of it. Remember how I commented on your boxers? I'm never sure what the day will bring. I'm prepared to offer the best version of myself at all times. Even if no one sees what you're wearing underneath most of the time, you know it's there. You never know when you may have an opportunity. I certainly wasn't thinking about sex when I prepared for this meeting. I just am always dressed for that possibility. Do you understand?"

"I do." And I really thought I did. "You were just prepared for any possibility. You didn't start realizing we were going to have sex." I hadn't realized it either and wasn't sure I was prepared to see this through all the way, despite my rebellious dick giving evidence to the contrary.

She laughed. Not a little but a lot. "Oh that is presumptuous. I have realized no such thing." She took another drink of wine while stifling laughter. I had no idea what I said that was so hilarious. All I knew is that I'd gotten it wrong again.

"Oh dear Ben, I have haven't realized any such thing. Is that what you think is going on? That you will secure your promotion by having sex with the boss? I mean, I do like you but I am selective about with whom I sleep."

I was a bit miffed. I'd been thinking something along those lines sure, but she wasn't quite right. "It's not that. I didn't think you found me desirable or were exchanging sex for a promotion. I saw it more as a way to maybe ensure my secrecy."

She gave me an appraising look. "Not bad Ben, you're learning. But when I said I trust you to keep a secret I meant it. While that has some added value, it really is more about putting the needs of others first in the organization. Right now that means my needs. Those needs don't include sex right now."

I knew better than to feel relieved and relax at this point. I was waiting for the next shoe to drop. I wasn't disappointed.

"However, Ben, I do want to see if your tongue is as skilled as your hands are. So while I'm not sure whether or not I want your cock inside of me, I do want you to get me off, knowing I might not feel like returning the favor."

She set down her glass of wine after taking yet another sip and laid her head back, spreading her legs slightly. Somehow, this was what I considered the point of no return. I could justify everything that had already happened as still being technically faithful to Belinda. Not this. I didn't hesitate. I supposed that when I stripped I had already gone all in. There would be time for thinking later. Right now my goal was to give this manipulative bitch as big an orgasm as possible. If that meant I was eating my way to the top, then so be it.

I took my time. I lifted the hem of her dress over her hips. I wanted a clear view of the target. Her legs were shapely, suggesting some sort of regimen like jogging or a StairMaster. They were also very smooth. Her pubic hair was nicely trimmed. I hadn't expected otherwise given that she told me she was always prepared. Maddy seemed relaxed as I slowly kissed and caressed my way up her right leg. Her eyes were closed. I think they closed almost immediately after she told me what she wanted.

It was clear she had no doubt that I would. She knew she had me. The combination of what I wanted and the fact she was attractive sealed my decision. She also smelled good. My cock was throbbing as I got closer to her pussy. I love how a woman smells down there and the scent was encouraging me. I was hoping to leave her a quivering mess.

She made sounds of approval as I started kissing her folds. I gently parted her with my middle finger. She was definitely wet. I also like the taste of a woman, and I got my first sample of her. No two women taste exactly alike. I'd been with Belinda for so long I was used to a very specific flavor. Maddy's was different, not better or worse, just different. I was enjoying that taste as I worked her over with my tongue.

I was rewarded by hearing increased breathing and gasps of pleasure from Maddy, along with the occasional word of encouragement. "Yes... right there... oh god... you are good at this... I knew it... I just may fuck you... ahhhhh...."

I was merciless with my tongue on her clit as my finger worked the inside of her pussy. She was a lake down there. I pressed up against the top of her finding a nice spongy spot. From the sounds, I definitely had found a good spot. She got louder at this point but if she was speaking any words, they weren't intelligible. Her thighs gripped my head cutting off my hearing a bit as she made a long sustained noise.

I stayed down there until her thighs opened back up and she pushed my head away. "Stop. That's enough."

I moved my head away, but traced my fingernails along the inside of her thighs. That produced quite a few satisfying aftershocks. I planted a few light kisses along her legs as well. She took a while to recover. I located my wine glass and sipped. I felt a bit self-satisfied. I also like giving oral sex. I was positive I'd delivered on that one.

When she got her breath back, she said, "Ben, you are full of nice surprises."

I just sipped for a bit. My cock was leaking precum. That happens when I get aroused, even with little to no stimulation. I was definitely mentally stimulated. When she sat up, it didn't escape her notice. I just continued to sip my wine with a grin on my face. I couldn't help it, I knew I'd rocked her socks off.

"You seem pleased with yourself," she finally said.

"Only because it seems I pleased you." I was learning.

"That was a very good answer. So good, don't say another word for the next few minutes."

She took another sip of wine then set her glass done again. Her head found its way to my erection as she maneuvered herself across the couch. Then with a, "Shhhh, not a word," she proceeded to give me a blow job. There's something highly charged about getting a blow job while drinking an expensive glass of wine. I didn't close my eyes. I watched.

She didn't exactly go slow, which was a good thing because I was ready to pop my cork at any moment. She just licked the precum off, then wrapped her soft tips around my shaft while she pumped me. I didn't last long; there was no way I could. She swallowed as I managed to do my best impression of Old Faithful while managing to hang on to my wine glass. It was close. I did slosh a few drops onto my hand.

Now it was her turn to look satisfied. "Lesson time again. Why did I do that?"

I felt like I had this one. "It's your way of letting me know that if I play ball good things will come my way. Also, you wanted to wipe the smug look off of my face."

She laughed. "Right on both accounts.

The next hour passed free of tension. Another bottle of wine got opened at some point and we both just talked a bit about our lives. She talked about her two children and her husband and I talked about the plans Belinda and I had for children of our own. Much of that conversation was had while I was still naked and she was still wearing her dress. I was pretty sure that thing was going to have a big wet spot on it, even after she took a short trip to the bathroom.

Eventually, we made our way to the bedroom and she got completely naked while we continued to talk. Of course the reason she got naked was so I could give her a back massage. I did get to see all of her charms and they were not disappointing. My hands may have taken a few liberties during the massage. After all, in for a penny, in for a pound.

I knew my life was going to change. The promotion wasn't mentioned, but I felt it was almost in the bag. While massaging and both of us drinking more wine, she invited me to ask her anything. She seemed quite at ease and I'm sure the fact I love giving massages had something to do with it. I asked the question I was most concerned about. How did she compartmentalize what she did with other men with her love of her husband.