Prior to the trip, Margaret and I had worked long hours together on the presentation we were to give and although I looked for any mistakes she might have made, that would have given me reason to keep her from presenting with me, she did pretty good. That didn’t stop me from giving her a hard time about things every chance I could.
During the week of the convention, Margaret and I spent our entire days together, giving the presentation and mingling with our fellow attendees. Although Margaret was able to handle her own when it came to company business, when an important client spoke about figures, she knew that I was to take charge and handled the deal. Each night, we went out to eat and had a few drinks.
On one particular night, at a Mexican restaurant, it seems we both over did it with the margaritas and really loosen up. What began with talking about her being single, slowly faded into our love lives. By the time we reached our fifth margarita, we were talking outwardly about sex and sexual fantasies.
Margaret took a long gulp to finish off her drink, leaned in and asked, “What is the most memorable thing that ever happened to you, in terms of sex?” Her eyes seemed to glow with curiosity.
It was my turn to polish off my drink in one, large swallow. I leaned into the table, in an effort not to be heard by the other diners around us, and explained that when I was in my senior year of High School, I had a teacher that would sit in a high desk that had an open front, while she taught her lessons. Because the chair was so high up, the teacher’s legs were at eye level with the students sitting in normal desks. Luckily for me, my desk was positioned directly in front of hers.
I began to get flush as I confessed to Margaret, who was herself leaning into the table so she didn’t miss a word, that a few weeks into the semester, I looked up from my notes and realized that I could look right up the teachers skirt. I then explained to Margaret that although I would hate to reveal to her my true age, that this was during the sixties, when the skirts were quite short. At first, all I saw was her knees because she had her legs together.
I went on to explain that, as the teacher spoke to the class and shifted in her chair, I would get many different views of her panties and her pubic mound, covered by the undergarment.
I sat back in my chair and explained to my Margaret that since that day, I have developed a fetish for women in skirts and for glimpse up their skirts.
Margaret beamed from my candid confession and motioned to the waitress to bring two more drinks. Margaret broke the eerie silence that came upon us by blurting out, “Hell! I was going to tell you about the time I gave my boyfriend and his friend blowjobs in my living room while my mom and dad were in the kitchen!”
At that point, we both laughed and changed the subject. Later that night, after I got a chance to sober up, I began to regret telling Margaret of my encounter.
During the last two days of the conference, Margaret seemed different to me. She seemed to have taken more charge whenever we spoke to clients, as well as during the presentations. Although she had dressed in business attire on the prior days of the conference, the way she wore her makeup and hair those last few days made her look older and more authoritative.
When we got back to work the following week, the president told us how well we did and suggested that Margaret work on more projects with me. One day, rather than have my assistant proof read a report I had created, I sent it directly to Margaret to read over and add her portion of the work to it.
When I returned to my office, I found that Margaret had returned the report with corrections on it. To make her point, she had used a red marker to circle grammar and spelling mistakes. I thought it odd but I chalked it up to how Margaret may make corrections to her other reports.
However, when I checked my answering machine, I received a message from Margaret stating that, “She was not happy with the quality of my work and thought I could have put more effort in the writing.” She added that she would be out of the office for most of the day and insisted that I see her at her desk after work to get it right.
I became defensive and couldn’t wait to put her in her place. I was the senior manager and she was going to be put back in her place? I tried to contact her for most of the day. When she finally did answer her phone, she cut me off, told me, “It will have to wait until I saw her later that day and that she will call me when she was back in the office.”
The day could not go by any faster. I waited for Margaret to return. As everyone else from the company began to leave for the night, I sat and seethed, waiting for the call from Margaret. Finally, just as I was about to leave, I got the call from Margaret, stating that she was in the boardroom and demanded that I get there immediately.
When I flung open the big oak doors, I saw Margaret standing in front of the room in a grey business skirt, what seemed to be an extremely white, crisp blouse and black high heeled shoes. She looked incredible. She had pinned her hair back into a bun behind her head and she was wearing bright red lipstick and thick rimmed glasses. She looked much older than her thirty years.
She met me with a stern voice and told me to sit in front of her and listen to her teach the lesson. She also told me to remain quiet and pay attention or she will have to discipline me. I immediately remembered back to the restaurant and of my confession about my teacher.
I could not resist. I sat in my seat and stared at the woman in front of me. I had to admit, I began to get aroused by the sight of Margaret in that attire and the control she had forced on me.
Margaret began writing on the white board on the wall. As she stood with her back to me and taught a lesson on proper writing skills, she allowed me to sit and watch her tight ass move about her.
It wasn’t until Margaret sat down in the chair in front of me that my growing cock ached to be released from the confines of my pants. As she spoke, Margaret would ever so slightly open and close her legs, purposely, giving me glimpses of her upper thighs and crotch.
I was longer able to pay attention to what Margaret was saying. Instead, I stared at Margaret’s legs and begged for another opportunity to see up her skirt. At one point, when Margaret stopped her lesson and asked me if I was paying attention to the lesson, I snapped out of the spell her legs had placed on me, sat up quickly to attention and blushed from being caught staring.
Margaret stood up like she was annoyed and came over to show me what she had on the paper she was reading from. Margaret was now standing to the back, right side of me. Because she had placed the paper so low on my lap, she had to lean quite low over my shoulder for her hand to maintain contact with the paper.
This enabled me to look down between the buttons of Margaret’s shirt and see her lace bra and deep cleavage. As she read the lesson from the page on my lap, I noticed that Margaret had allowed the back of her hand to rest deeper into my crotch.
As she spoke, Margaret, as if to do it secretively, so no one in the “class” could see, began to slowly move the back of her hand up and down the shaft of my dick. I in turn, allowed my hand to hang from my side and slightly brush the side of Margaret’s calf.
Slowly, I made my hand rise up, rubbing her lower leg and back down, hoping that she would not catch me. My heart raced. I was so scared that the “teacher” would realize what I was doing or one of my imaginary class mates might see me. I was fighting the urge to go higher up her leg, in fear of getting in trouble. I finally got the courage to make my move.
I slowly brought my hand behind her leg, stopping when I touched the inside of her leg at the calf. Slowly, I brought my hand higher up and rubbed the inner part of Margaret’s leg and then slowly went back down. Each time I went up, I would go a little bit higher. I finally went from her calf all the way up to Margaret’s inner thigh. However, I did not go back down. Instead, I gently rubbed and squeezed her soft flesh.
Margaret began to have difficulty of her own to maintain concentration on the lesson. She quietly stood there running her hand over my cock while I slowly inched my way towards her pussy.
When my hand went as far up her leg as possible and I touched her pussy, I felt the heat emanating through her panties. I smiled when Margaret squeezed my cock through my dress pants and gave a gentle sigh. As I began to rub Margaret’s pussy through her panties, I took this opportunity to reach over with my left hand and squeeze Margaret’s right breast.
Margaret suddenly released my cock and stood straight up. She looked very angry and asked me, “What I thought I was doing.” This caused me to become confused and lower my hand from beneath her skirt. Margaret walked up in front of me and sternly asked, “How dare I touch her breast while she was helping me with my lesson!” Although I apologized, she would hear nothing of it.
As Margaret slowly unbuttoned her blouse, she sternly questioned if I even knew what to do with a woman. She then noticed the bulge in my pants and asked me what exactly I planned to do with that hard cock. She smirked when I played along and admitted that I did not know.
Margaret stood in front of me, straddling my legs and placed her exposed breast in front of my face. She stated that, “If I felt bold enough to touch her breast without permission, we should see just how good I am at satisfying a woman.”
Margaret unzipped the fly on my pants and pulled out my cock. Margaret quickly raised the hem line of her skirt, grabbed the waistband of her panties and pulled them down and off her legs.
I leaned in and began to kiss Margaret’s cleavage. I worked my lips over Margaret’s breasts, stopping to gently bite, when I reached her erect nipples. I reached back under her skirt to find her now naked pussy. I inserted, first one finger into Margaret’s pussy to make it wet with excitement, then another, as she began to moan softly.
As Margaret stroked the back of my head, I devoured her breasts. My fingers worked as a piston as they pumped in and out of Margaret’s pussy. The deeper I pushed my fingers into her cunt, the louder Margaret would moan. I pulled my fingers out of Margaret’s opening and licked the slick juices into my mouth. I asked Margaret how I was doing for my first time with a woman.
Margaret lowered herself onto my lap, grabbed hold of my rock hard cock and guided it towards her swollen pussy lips, all the while looking into my eyes. She did not stop until her pussy engulfed my entire shaft. She was surprised when I had thrust my pelvis up for good measure.
As Margaret rode my cock, I closed my eyes and threw my head back, amazed at how great her pussy felt, wrapped around my dick. I suddenly remembered just where we were, before this fantasy game began. I looked towards the boardroom door and wondered if there was anyone still in the building that could walk in on us at any moment. I shared my thought with Margaret.
She simply flashed a wicked smile and reached down between our bodies to work her swollen clit. The excitement of possibly getting caught was too much for either one of us. Margaret quickened her pace of riding my cock and suddenly began to come.
As Margaret’s young pussy clamped down on my cock, I began to shoot stream after stream of my semen up into her pubic cavity.
We sat frozen for a moment, enjoying the remnants of our joint climax. It was Margret that broke the embrace first. She quietly leaned back away and raised herself off my well spent cock, giving me a final look at her young, lean body. With her hair down and business attire askew, Margaret no longer took on that mature teacher posana. She once again looked like my junior executive.
Once we were dressed, I walked towards the door to leave. Before opening the door, I turned towards Margaret and said, “I want to speak to you tomorrow in my office about your math grades. let’s see if I enjoy dealing with a student as much as I enjoyed being one.
