A Boss a Mentor a Lover

I was 23 when I landed my dream job at ADM Advertising and Marketing, a national firm. I had graduated from college over a year previously so I was getting pretty desperate to find a job to further my chosen career, one that didn't involve waiting tables or mowing lawns. My first boss, the guy who hired me, was on his way out the door, just months from retirement. When he left, a co-worker in my department took over his job as director and became my boss. Her name was Carrie Sterling, and I was happy that I'd be reporting to her.

She had treated me well in the several months since my arrival, and I believed she'd make a good supervisor. She'd been with ADM for five years and had impressed management from the day she started. Her promotion was inevitable, and she was earmarked to continue her rise through the company.

Carrie was six years older than me, but never came off as condescending or haughty, even though I was a bit green, this being my first corporate job. Over the next couple of years I tried to learn as much as I could from her and my co-workers. I grew into a reliable idea and creative guy, and I learned pretty quickly. When they finally let me begin pitching concepts to both current and potential clients, the true art of our jobs, I was generally cool under pressure though a bit timid. I needed to learn aggressiveness.

This, Carrie decided, was her responsibility and she took it upon herself to take me under her wing. "Stillman," she said one day after a client meeting, "you've got a lot of potential, but you need more balls. I'll teach you. From here on out, you're going to meetings with me." It was this kind of good-natured ribbing and tough love I'd come to expect from Carrie. She was definitely tough as nails and expected everyone who worked with and for her to be the same way.

She wasn't unfair by any means, but she had no problem ripping into people if they didn't perform up to potential. She'd never chewed me out for anything before, perhaps she'd given me some honest criticisms here and there, but she never called me out, embarrassed me or questioned my intelligence. Instead she allowed me to mature in my role, without undermining my confidence.

Because of this, I respected Carrie a great deal. And I got a lot better at my job while she was mentoring me. Over the next year and a half, I attended every client proposal meeting with her. At first I was a bit intimidated, but soon enough we built a work rapport that was something to be reckoned with.

Our success rate slowly grew through the roof. In high-pressure meetings, Carrie would play the role of aggressor while I'd temper her hard-ass routine with wit and humor, putting clients at ease. The result of this good cop/bad cop routine was that clients knew we had good creative ideas with their best interests at heart, but we also meant business. So we consistently got great results and made damn good money for the company.

"Jim, I gotta tell ya, you're getting better every day," Carrie said to me as we were leaving a particularly good initial meeting with a potential client. "Thanks Carrie," I replied, "I really feel like I'm getting the hang of this."

"Oh great, only took you, what, four years?" Her ball-busting had become more frequent the more successful we were. I didn't mind it at all. I had really grown to like Carrie, and truly there was a lot to admire about her. She was a great boss, a good motivator with solid instincts who was loyal to her team. She was driven and also took good care of herself. She exercised regularly, packed a healthy lunch for herself every day, and consistently had great energy and mental strength. She was average height, about 5' 5". Her exercise regimen left her toned and sleek, but not in the least bit unfeminine. In fact, she had soft curves, especially in her waist, hips and backside.

She also dressed impeccably, and chose fashionable clothes that complemented her lean, toned body well without being inappropriate for a business environment. She wore a modest amount of makeup, and kept her light brown hair shoulder length and informal, so that she never looked overly done up. And she never overpowered her light green eyes with too much eye shadow or mascara. The result was that she came across as confident, but not full of herself, and as you got to know her you realized how sexy this made her.

She had married her husband Paul five years prior; he was a lawyer several years her senior. They made a good couple, but every time I was in their company, I couldn't help but feel that he was a bit stiff and cold. Sure, Carrie was a hard-ass in business, but she had a humorous and mischievous side to her that softened her personality. I never sensed that from Paul. While Carrie was serious about her career, she was also down to earth and grounded. Paul always seemed a bit full of himself.

"Oh whatever," I responded to her barb, "you'd be nothing without me."

"Ok, you got me there. Sterling and Stillman, we're a helluva team."

She was hailing a cab to take us back to the office. We worked in a pretty big city, not a major metropolitan but fairly large. My apartment was outside the city where it was calmer though. I chose to live nearer to the small town where I grew up and commute into work. Personally, I liked some elbow room. During the cab ride back, Carrie gave me some good news.

"All right Jim, I've debated telling you this, I'm really not supposed to..." She paused leaving me in suspense.

"Well, hell, you have to tell me now," I replied.

"Right, so... we have a killer meeting with a national phone service provider next week. They've been a client of a competitor of ours forever, at least 10 to 15 years, and they've always denied our requests for a face-to-face. Until now. We have no idea why they've granted it to us, and management is pissing their pants right now. No one wants to jinx it. So, here's the thing, they've offered me the meeting."

"No shit," I gasped, "that's huge. Congrats!"

"Yeah, well... you up for it, Stillman?" I couldn't believe my ears. I'd prepared presentations for, and gone on, dozens of initial meetings, but never with potential clients this big, with this much money at stake.

"Are you serious?"

"You know I wouldn't have offered if I wasn't."

My initial reaction was to be terrified. This was way bigger than I was used to, and it was intimidating as hell. Sure I'd been at the job for about four years, but this was the kind of opportunity that went to people with a lot more experience than me. But then again, Carrie had spent damn near two years teaching me to be more aggressive and confident so I couldn't let her down now that she'd given me this shot.

"Yeah Carrie, I'm up for it."

"That's what I wanted to hear," she said smiling at me. Our cab pulled into our office parking lot and we both got out. "Ok, good meeting today. Go home early and get your head together. Tomorrow we start our crunch planning for the big one next week."

"Ok," I replied. She began to walk away, but turned when I called to her. "Hey Carrie... thanks." She nodded in understanding, and continued walking toward the door. I turned to start walking to my car, but stopped to watch her walk away. Her skirt hugged her hips and ass tightly, creating a soft, curved w, creeping just slightly into her crack. Her heels elongated her shapely calf muscles, and made her ass swing back and forth in a delicately feminine, pendulum-like manner with each step.

Admittedly I had begun to look at Carrie like this more and more every day. I had remained single and unencumbered throughout most of my 20's, mostly for my job's sake. I just didn't want to be tied down. Sure I'd had my share of sexual partners and dalliances, some more adventurous and strange than others; I was definitely getting mine. But most were fleeting and temporary; a girlfriend just hadn't entered my thoughts.

This fact came much to the displeasure of my sister, who was also my best friend, who wanted to see me settle down. I knew I would eventually, but for now I wanted to be unencumbered. This lifestyle offered me freedom, but it also created its share of cravings.

When I first started working with Carrie, I was a bit intimidated and in awe of her. I never allowed myself to fantasize about her or think of her at all in a sexual way. It was hard not to, she was gorgeous, but I buried those thoughts away when they cropped up for my own damn good. As our rapport grew stronger though, and our successes became more frequent, a confidence was growing inside me and I began to see her in a new light.

I'd take notice every time she stretched or yawned, watching the way her clothes clung to her curves. I'd admire her legs when she crossed them or swiveled in her chair, her feet when she'd kick her heels off and go barefoot later in the day. When she'd remove her jacket, I'd admire her small, but very pert breasts, or her lean arms when she rested her head on her hand. She was quickly becoming a fantasy for me, an unattainable goddess I could merely admire from afar.

I admired her in secret because I respected her far too much to ever betray her trust. She was a consummate professional, and my career owed a lot to her mentoring and direction. I knew in my head that I would never do anything to risk hurting our professional relationship. I would never say anything suggestive to her, or, god forbid, make a pass at her. But it was becoming more and more difficult not to lust after her.

Just recently I'd seen something that was permanently stuck in mind. We had stayed late to work up some concepts. It was only she and I left in the office by around 8:30 and we were both pretty burned out. I'd taken off my tie and jacket long ago and she had removed her jacket and kicked off her shoes. We were sitting in a conference room trying to hammer out one more idea, but were getting nowhere. "God, Jim, I am so fried," she said as she leaned back and stretched, yawning. "I dunno if there's anything left in my brain."

After saying this she finished her yawn and stretched her legs up onto the table. I was sitting next to her, and her feet landed just in front of where I was resting my head on my hand, reading through some notes from earlier. Without turning my head, I gazed discretely at her feet; they were small, feminine and cute, but her toes were actually quite long in proportion to the size of her overall foot. She had light, tiny little hairs growing on the knuckle of each toe, and for some reason I found them strangely arousing. Her toenails were painted red; this was the closest I'd ever been to them so I drank in every detail about them. I don't have what you would call a foot fetish by any means, but I appreciated how sexy Carrie's feet were.

After a moment of admiring her feet and toes, I turned my head slightly and was greeted with an incredibly beautiful sight. I was looking down the length of her leg, up her skirt. She had leaned back in her chair and put her hands behind her head, reclining her head back to look toward the ceiling. I sat there resting my head on my hand looking up her skirt at her creamy, white thighs. She wasn't the tanning type, so her skin was always soft and creamy white. Her skirt was modest, cut just above the knee, and today she'd decided against wearing pantyhose. I couldn't see very far up at first but as she reclined further, she began to subtly spread her legs just a little more. It could have been my imagination but it felt as though she was doing this on purpose. I could now see her upper thighs, and the sensation was making my head spin.

She was inhaling deeply through her nose, and had her eyes closed, relaxing. After several moments, she yawned and stretched again. This time she spread her legs even wider and gave me a clear view of her silky white panties. They were smooth and thin, trimmed with a delicate floral pattern, and they hugged the curve of her mound and pelvis softly. My heart was now pounding in my chest. I was overcome with a deep, driving urge to run my tongue up her leg and over those beautiful silky panties. Without opening her eyes she moaned and murmured, "I think it's time to call it a night." I was struck by the desire to say, "Actually, I think it's time we really made the most of this night." But instead I just said, "Yeah, you're right."

When she leaned forward and opened her eyes, I think she could tell that I'd been admiring her. She said nothing but gave me a quick, knowing look. After that we packed up and headed home, and the image of her soft, smooth thighs and delicate silk panties had been burned in my mind ever since. The contrast between the hard, business-like exterior, and the soft, sexy, panties that lay beneath was haunting my mind, cropping into my thoughts at random moments throughout the days when I was with her.

The next few days were filled with long meetings to prepare for our big face-to-face. Two days before the scheduled meeting, Carrie dropped another bombshell on me. "We have to drive to Philly for the meeting. We'll be there all day so we might as well get hotel rooms and not worry about driving back after." Of course this idea thrilled me but I didn't let on. I just said it was no big deal.

The day of the meeting we made the several-hour drive to Philly reciting our gameplan. We stopped at the hotel first to check in, then took a cab to the clients' office building. When we met with the execs, the process could not have been smoother. We worked our routine masterfully. We learned that the clients felt mistreated and were unimpressed by their current marketing firm. They said it seemed like the company they'd used for years had grown complacent and no longer seemed to see them as a high enough priority.

By the time we left, we'd convinced them that complacency was the last thing on our minds and consequently they were singing our praises. The outlook couldn't have been brighter. We offered to buy their executive team dinner but they politely declined. It looked like they were going to make us sweat a little bit. But still, I'd never seen Carrie so ecstatic as when we walked out of that meeting. We hit the street and she was gushing.

"Fuck Jim, I mean holy shit! We rocked, we absolutely fucking rocked! Nothing is in the bag and we can't count any chickens yet, but fuuuuck! Holy shit, seriously..."

I'd never seen her this excited before. All level of decorum was completely forgotten. I felt great too. "Damn right Sterling, we slayed today, absolutely slayed."

"You were awesome, Jim. You so had your shit together. Even when they pushed on you to see if you'd crack with your 'good cop' routine you just fired right back. You really earned their respect in there."

"Thanks Carrie, you were amazing, this was all you."

"No, Jim," she said grabbing my arm and stopping me, "I'm really proud of you." She threw her arms around me and hugged me. "That was so awesome."

"I owe it all to you," I replied. Her embrace sent shockwaves through my body. We held each other for a moment and I realized this was the most we'd ever touched. All we'd ever done prior to this was the occasional high-five or fist pound, certainly we'd never hugged. Even at the annual Christmas parties we only ever did the one arm shoulder hug at most. Or every once in a while she'd touch my arm or graze my leg just for a second. Those few fleeting moments were a special treat, and I'd gotten a thrill out of them. But now I absolutely reveled in this embrace and enjoyed the feel of her body pressed against mine.

This was no arm hug; our whole bodies were pressed together, almost in relief. Like we'd both wanted to press against each other like this for some time, and the relief of surviving the meeting had given us reason to. I know I had craved this embrace, but I couldn't tell for sure if she felt the same. We hugged just a little longer than I would have expected, but when she broke the hug she grabbed my arm and we kept walking. Finally I said, "Hey, where are we going anyway?" I had never been to Philly and had no clue where we were.

"Fuck it, Jim, we're walking back to the hotel. I'm too excited to sit in a damn cab and it's only a few blocks anyway. We'll enjoy the city of Philly more this way and we'll get dinner at that restaurant in the hotel when we get back. Whatdya say?"

"Sounds great," I said. And it was. The walk back to the hotel was almost magical. The city was beautiful on this spring night and Carrie was gorgeous in her outrageously celebratory mood. She even held my hand at one point and swung it back and forth as we walked. At another point I carried her on my back so that her feet could rest. She was wearing heels and I didn't want her to hurt her feet or get blisters. I also loved having her legs wrapped around me, to have her on my back with her arms around me clutching me. I could smell her sweet perfume, and her hair smelled incredibly sexy as the breeze blew it into my face. "We did it, we so pulled it off," she kept saying. I would just laugh and say, "Of course we did; we're the shit," in reply, and she would squeeze me tighter. I almost didn't want the walk to ever end.

We arrived at the hotel and she crawled off my back, smiling. "Thanks, He-Man," she quipped, gripping my bicep. Again my heart skipped a beat. We got to the restaurant at the hotel and were lucky to get a table. It was a weeknight, otherwise the maitre'd assured us we wouldn't have been so lucky. Carrie had calmed a bit as we sat down to eat. She was gazing at me admiringly with her stunning green eyes. She had settled into a euphoric, satisfied calm after she made the call to her boss, our regional manager, to give him the good news. Now we were relaxing sitting across from one another in an atmosphere not unlike afterglow. I imagined this must have been what Carrie looked like after orgasm. She had an alluring, satisfied smirk on her face.

"Can you believe we did it?" she asked me calmly after we ordered a bottle of celebratory champagne.

"I'm just so proud to be here, so happy to have been a part of this."

"Well, I'm going to let you in on another little secret. When they offered me this meeting, our higher-ups made it a point to tell me not to get my hopes up. They figured the whole meeting was just a way to get that other company to buck up and start paying attention again. Truth is, we only thought we had maybe a 10 percent chance at best of actually landing this deal. I didn't tell you before because, quite frankly, I thought we were good enough to make big things happen. And together we did. I know nothing is final yet, but we're in, I can just feel it. You really shined today, Jim."

"Thank you, Carrie," I replied, stunned. "You've really made all this happen for me."

"Bullshit, Jim, you made this for yourself. I've never given you anything; you've earned it all. You've really grown over these last four years. I don't wanna sound like a mom, but you've made the most of every opportunity."

"Ok mom," I teased. "You're not going to give me warm milk and a cookie and send me off to bed later are you?"

She laughed. "No Jim, I'm not your mom, and I don't see you as a son. With how incredible you've been lately, I couldn't look at you like that. As for sending you off to bed with a cookie though, well that'll just depend now won't it?"

"Will it now? Depend on what, might I ask?"

"On if you're a good little boy of course." She laughed again after saying this. This suggestive flirting was new; we had never flirted like this. We joked around all the time but there had never been any suggestiveness in it.

"I'm always a good boy," I replied smirking.

"You are." As she said this our champagne arrived. We toasted our job well done and one another repeatedly. When dinner arrived, we discussed the meeting in detail as we ate, replaying all the big moments over again. The give and take between us was comfortable and jovial, and the champagne started going to our heads.