Chapter One – I gotta wear shades

Corporate Ambitions

I gotta wear shades

During my initial interviews with several large corporations, I was intrigued most by Women’s World. The position being offered was executive assistant to the CEO. Talk about starting right up there! The idea of working directly with a CEO, along with a generous compensation and relocation package was more than I could resist. I shrewdly figured that working directly with the CEO would put me on the fast track to the top. I put a very good effort into this particular interview, and it seemed to pay off.

Doris, the interviewer for Women’s World was quite charming. I figured her for the Human Resources Dept. director and not one of those paid recruiters. She seemed to know everything about Women’s World, and I asked a lot of questions, priding myself on interviewing my interviewer. But I could not get a read on this one. Nothing I could put my finger on, but at times I swear I caught Doris trying to hide a smirk. Finally, Doris left me with a few encouraging words and a very large packet of material for me to fill out and send back to her. She said she felt fairly confident she could get my application “in front of” R. Williams, the CEO and, in this case, hiring manager.

I had nothing keeping me in “B” school town. No wife, no romantic interests, no more promising prospects, so I said, “What the hey.” I filled out and sent the information called for in the hefty package Doris had given me. I wasn’t really surprised by the voluminous pre-employment miles of paperwork, given the position being offered. But I was a little curious about the requirement to include several photographs, and the specific emphasis on at least one full body shot. I just shrugged and thought, “Probably too many guys wearing jeans and sneakers while looking all business-like from the waist up.”

I wasn’t expecting a response for a certainty, and when I received an e-mail directly from R. Williams/CEO I was somewhat surprised. The e-mail explained that my employment package was “impressive”, and asked me to respond with a time that would be good for me to discuss the position available. My mind was reeling, as were my thoughts of even better chances of moving up the ladder fast. I e-mailed my reply immediately and set up a time for the call the next morning, if he could put me on his calendar then. “She” responded within an hour advising me of the time for our “teleconference”. I was a little embarrassed to learn only then that R. Williams was a Ms. Rebecca Williams. I can remember thinking, “Hmmm, this is going to be easier than I thought!”

The next morning the phone rang at the appointed time, and I nearly jumped out of my skin. I tried desperately not to sound nervous answering, being somewhat unprepared at such an early hour. But it only took seconds for her to put me at complete ease. Her voice was very soothing yet intensely commanding, as she led the conversation precisely where she wanted it to go. It seemed like only a few moments but it had been nearly an hour since we had begun talking and I was accepting her invitation to go to Florida for a second interview. The real kicker was that she had a corporate jet in town for business and offered me a free “hop” if I could go the next day. I was packed and out the door the next morning at the crack of dawn, heading for a private section of the airport. I was certain I was headed for greatness!

The plane ride was rather uneventful, but it was the first time I had ever been on a Lear jet. My mind concentrated on the future that lay ahead, and my visions of grandeur were, to me, pragmatic and clear. I would land this job, then work myself into the graces of this Ms. Williams until I would be the new CEO. It seemed like only minutes but it was actually 2 hours till we were landing at a small private airport in Florida.

The first of many pleasant surprises awaited me when I stepped off the plane and saw a limousine waiting to drive me to my hotel. Even more pleasant was the chauffeur, who had to be the most beautiful woman I had ever seen. Tall, blonde and gorgeous! The leather riding pants she wore made no effort to hide the most luscious derriere I had ever seen, and her black satin blouse likewise showed off a pair of beautiful breasts to their utmost. I knew I would love to spend time with this woman. Yet, like Rebecca, she was at the same time soft spoken and still somehow very direct. She welcomed me and held the door for me. “Nice touch,” I thought as she sped us to my hotel in the powerful car. At the hotel, she opened the door for me once more, and told me she would meet me in the lobby the following morning at 8am sharp. Her face changed a little when she said in a voice that betrayed a hundred times, “Please try and not be late! Ms. Williams is irritated easily by tardiness.” With that she was off, leaving me with a vision of her cute, wiggling ass and many female conquests that were yet to come. As I watched the way she moved, my eyes glued to her ass, I joked to myself, “Hmmm, two Volkswagen Beatles vainly trying to pass each other on the Freeway.”

I entered my room still wearing the self satisfied smile to find a chilled bottle of wine and a welcome note from Women’s World that enthused how looking forward to meeting me they all were. “I could get used to this,” I quipped out loud, as I stripped to my jockeys. I sat down and started going through the Dunn and Bradstreet report on Women’s World, ticker symbol Ww (boy they had been around a long time). I had brought piles of reports with me on this company. I wanted to ensure I was really prepared for this interview. The more I learned about this company, the more intrigued I became. They were an acquisition company, but with a focus, it seemed. I was just piecing it together when the day caught up with me and I fell sound asleep.

I was up at the crack of dawn, shaved, showered and in my best, neatly pressed Brook’s Brother’s suit. While waiting in the lobby for the limo to pick me up, I garnered all the enthusiasm I could muster. The limo arrived at precisely 8 and I was pleasantly surprised to see that my gorgeous blond chauffeur, Janie, had traded in her riding pants for a short, tight, leather mini-skirt. Talk about legs, this woman had some of the most gorgeous legs I had ever seen. I could only imagine where they lead. I figured she might well be my first conquest! Janie was the epitome of sexy and I was disappointed when we’d arrived at the offices of Women’s World so quickly!

We pulled into the sprawling Women’s World headquarters campus at just 8:30, and Janie escorted me to the lobby. The building was rather unassuming for a Fortune 500 company, but that was nothing compared to the inside. It was very obvious from the décor that this business was owned by and catered to women. There were light pastel colors and everything was so very “pretty”. I remember thinking how I would change it once it belonged to me. The thing that threw me most, though, was that there didn’t appear to be any men working there. Again, I was smirking. “Oh yes, this is going to be easier than I thought.”

The area opened into a kind of bullpen, with secretaries sitting in the middle, and offices around the perimeter. And, the women were all so beautiful. “My dumb luck,” I mused, “to stumble into such riches.” As the secretaries milled around, not one of them wore anything but a nicely tight, short mini-skirt, showing off their long, luxurious legs, which of course descended into sexy high heels. Wow!

Everyone from the receptionist to the secretaries was attired thus. I was totally absorbed in a vision of all the fun and “bennies” I was going to have at this job. Just then, the receptionist snapped me from my reverie telling me in a stern voice, “Ms. Williams will see you now.”

I snapped out of it, shook my head, and focused once again, walking into her office. It was like any other CEO’s office. Plush and very comfortable, with a singular exception… its decor was very feminine. Then the tall, leather armchair behind the desk turned around and I saw Ms. Williams for the first time! She stood to shake my hand firmly, and I had trouble making the words come out of my mouth. She was stunningly beautiful! She was wearing “the” classic, tailored, woman’s business suit. While it was a suit, it remained somehow sternly feminine, if there can be such a phrase. It was all business, but still highlighted her charms to the maximum! I made her somewhere between the age of 35 and 40, close to my age, if perhaps a bit more sophisticated. And it was obvious that she took very good care of herself. No single word superlative I can think of to describes her combination of beauty and demeanor adequately. Statuesque, perhaps, comes close. I needed to remind myself to breathe!

Taking the lead, she offered me a chair as she began. Just as on the phone, her voice was soothingly disarming. She had me at ease in an instant, with her easy charm. She asked me questions about my education, where I came from, and my career ambitions. She also told me a little bit about her company, most of which, I already knew.

About half an hour into our interview she was called from the office on an emergency, and as she left, she told me to make myself at home and to check out “the surroundings.” I could not resist. I got up and began looking around the plush office, thinking, “Someday it will be mine, all mine!”

Walking to a table with some open boxes sitting on it, I saw what had to be some of the most beautiful lingerie ever conceived. “These must be some samples from one of the manufacturers,” I mused, holding the dainty things up to the sunlight. I could just imagine what my chauffeur, or any of the secretaries for that matter, would look like in this lingerie. And even more so, Ms. Williams! I continued my explorations and picked up a pair of pink, satin panties and while admiring them, suddenly felt her standing right beside me! I dropped the panties immediately, blushing a bit. Ms. Williams, or Rebecca, as she had asked me to call her, laughed lightly and said, “Not to worry dear, we are in the lingerie business and know precisely how lovely these things are. You’d be surprised how many men we sell that kind of thing to.” I stuttered my disbelief’s and went back to my chair, scowling.

Rebecca went back around her chair, and while standing behind it, smiled down at me. She took the back of the big, leather chair in her hands and asked in a disturbingly matter of fact voice, if I believed that men would buy such pretty things to wear themselves? I spat involuntarily that I couldn’t believe it! She just looked at me quizzically and replied, “You would be surprised with the number of orders we send to P.O. boxes with addresses to only a first initial and last name. We’ve done some research and found that most of these orders are from men who want to remain anonymous. Now why do you suppose that is? We could care less, of course. Business is business, no matter who buys! As a matter of fact, I bet you would be extremely turned on if you would slide a pair of our silky panties up your thighs and around your waist!” I stammered that I most certainly would not! She looked at me with a wry smile and continued, “I’ll tell you what, Mr. Smith.” She said it with a touch of cynicism in her voice, “I have reviewed your resume and references quite thoroughly and I am impressed. However, I am still not convinced you are cut out for a business career with this particular company. What say lets make a little wager?”

“Wager?” I stammered. “Yes, just a little wager. Since you seem to doubt my word about men buying and wearing panties like those pretty, pink, satin ones you, yourself were admiring, and since I can’t afford to have an assistant working for me who doubts my word on anything, lets make a little wager. I want you to take a pair of our panties and go into my bathroom and put them on. If you are not aroused by the soft satin, I will give you a check for $50,000.00 and send you back home on my jet at my expense. But if you become aroused, you will work for me for an entire week, learning my business and doing exactly as I say. And…” she looked thoughtfully at me before finishing, “You will wear panties under your Brooks Brothers suits the whole time! At the end of a week, if you have proven to me that you no longer doubt my word; that you can without hesitation do what I ask, and we both agree on it, I will offer you the job as my executive assistant. The pay is $150,000 a year to start, plus benefits, plus relocation package.”

“To make the bet even sweeter, if you do win, I will give you two nights with my gorgeous chauffeur, Janie. I know you liked what you saw, you are a normal man right? And every normal man lusts after that beauty. Well? What do you say Mr. Smith? Oh and by the way, I won’t watch you change. You can lock the door and after you change you will come back out into my office and sit with me chatting for a half hour before the decision about your arousal is made, if it takes that long,” she snickered.

Then she came around from behind her chair and settled back into it, looking at me with an evil grin. I just sat there thinking. Why not take this bet? I may not get the job, but $50 K free money and a ride back home, and most of all, two nights with that gorgeous babe chauffeur! I couldn’t lose! Look at it as a paid gambling trip where I got $50K and laid to boot. I could do this, it would be easy! I looked at Rebecca and choking back a laugh, said, “You’re on! I’d like my $50,000 in cash please.”

I expected Rebecca to get up and hand me the satin panties I was admiring before. Instead, she pulled open a desk drawer. I will never forget my chagrin as long as I live. She pulled out the prettiest panties I had ever laid eyes on! They were pink, and all satin with big ruffles at the waist and legs openings, and tied on with satin ribbons. This meant that I would actually have to work at putting them on. Not just sliding a garment up my legs, but I would have to tie bows at my hips. As she handed them to me, she firmly restated that I had 3 minutes to get the panties on and be back in her office with nothing around my waist and crotch but the panties. Her eyes were mocking, while I realized I hadn’t noticed before how tall she was. She rose from her chair, and pulling herself to her full height, held the mischievous garment daintily between her thumbs and forefingers, tauntingly. The expression on her face said that it was not her practice to hold panties in such a way.

I indignantly snatched the panties out of her grasp and headed to the adjoining bathroom thinking, “This is the easiest 50 thou I would ever make! Closing the door, I took my pants and socks off, then came my Jockeys. I held the panties up and then tied bows where I thought they should go. Then I just stepped into them, pulled them up my legs and began settling them into my crotch. Turning around and looking in the mirror, my pride suddenly vanished as I felt and saw my cock begin to rise of its own accord, filling out the front of the panties. I panicked! I grabbed my cock and squeezed it hard, trying to make it subside. All this did was to arouse me more. What was I going to do? I had only three minutes to be out or I would lose, but going out like this was a sure loss also. What would I do?

Fussing with the infernal satin straps at my hips, I’m afraid I wasted a lot of the precious three minutes. As Ms. Williams knocked at the door I knew my three minutes were up!

“You can either show me you’re not turned on, or admit defeat,” came Rebecca’s voice from the other side of the door. “Well? Was I right or not?” the impatient voice insisted. Her tone made it clear she already knew the answer, and seemed to drip smugness. I had never been so humiliated! I was trapped! I could not show her my now raging hard-on, and I certainly wasn’t going to give her the satisfaction of seeing me with the ruffly panty tied across my ass with a big bow at each hip, no less! “OK, you win,” I admitted. I wished my voice were not quite so sheepish.

“Get out here, Heath! Or is it Heather, now?!” she mocked. “OK, so I lost the bet,” I confessed, as I hurriedly pulled my pants on. I was so flustered; I didn’t know what to do. I hesitated, took a breath, then finally opened the door and came out. I tried hard to look casual about the whole thing.

“The terms of our little wager were for you to show me how you are not turned on by the feminine lingerie this company sells. I hope I have made a point, ‘Mr. Smith,’” she chided with a particularly sarcastic emphasis on her use of the masculine title. I knew it could be a long time before I would get a respectful “Mr. Smith” out of her again.

Rebecca continued, “We sell these things to make money! As CEO, I care a lot about our bottom line. But I think you are a good sport! Welcome aboard, you’re hired!”

I was embarrassed and thrilled all at the same time. Red faced to have been maneuvered into making the silly bet, and losing! Thrilled to be offered this kind of money and a position so near the top of a big company. But I was still wearing those teasing panties under my pants. My still stiffening cock strained hopelessly against its satin crotch, making the elasticized leg openings tighten a little more across my ass. Oh, I was more aware of my ass than I had ever been in my life. Finally I offered, “I will accept the job on the condition that you release me from the consequences of our wager.”

Rebecca’s face grew into an exaggerated look of pretended dismay. “A bet’s a bet,” she smiled knowingly. “You wouldn’t welch on a bet, would you? I expect you to be properly pantied for the rest of the week, and I want no lip about it! These terms of our wager you agreed to separately, and my offer of EA stands on its own. Have we a deal, then?” She stood with her hand outstretched. A lifetime seemed to pass before I returned the handshake- her grasp was firm, and the deal was done!

“Good,” she said as though dismissing me. “Now get down to lingerie manufacturing and pick yourself seven or so pairs of panties. I can’t have my EA wearing the same panties all week long, now can I?” I was horrified! “ME?” I eeked. “Me get panties? I have to do it?”

“Yes, and by the way, we’ll be having dinner tonight, say around 8,” she said flatly while writing something into her appointment book. Then, looking up from her desk, “Is there something else?”

“No, ma’am,” I heard myself say. Where was the lingerie factory?

.. continued

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The unworthy apprentice sissy writing this has written You many times asking for help. You have always made he.r life better. The House has been the very foundation of he.r life. Thank You again for Your efforts.*curtsey*.

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