Training Day

As far as he knew it started with a simple flirt. A comment was made by Megan, our training manager, about stuffy executives as she passed by my office on her way to a meeting. Heading to the same meeting, I exited behind her and joined the conversation with something playful like "I think you'd find me pretty open-minded." She slowed her pace, breaking from the group she had been walking with, and looked over her shoulder with a smile. Megan was a stunner, about 5'5, shoulder length straight auburn hair and an alternative but business classy style. I really enjoyed her educated, sarcastic wit and was glad she paused for me. Her dark purple lipstick drew my eyes to her lips as she responded to my jest, "oh really, that could be fun." She had a tight body from regular workouts which she proudly posted on her social media feeds and with that comment my mind and eyes began to wander over it. I was tongue tied and very distracted by the sexual overtones and responded only with a "hah!" as I opened the door to the conference room for her. Back to work.

But, it was hard to stay focused as she had sat directly across the table from me. She was wearing a form fitted, thin knit top with a high mock neck that beautifully displayed her ample breasts above tight abs. My eyes kept wandering. It was a good thing that the conference table hid her skirt and high heels. The meeting continued but my mind was focused on her. Wow, I was horny and I wanted her, but she was married as was I. Still fun to think about during some future masturbation session. This meeting was dull and she was hot, sitting over there smiling at me with those big purple lips. Oh no, had she caught me looking? I returned a smile and forced my mind back to the meeting. It ended and the day continued, back to normal.

Towards the end of the day when the meetings had ended and most had left the office, there was a knock at my door. "Can I talk with you for a few minutes?" Megan asks, standing at the threshold. I'm a bit worried as she enters and shuts the door behind her, me trying not to stare at her ass, figuring that's why she was here and that I was in trouble. She turned a chair from my conference table around towards me and scooted it up close, just enough so the hemline of her skirt was obscured by my desk. Focus Jeff. "I'm really excited for the training class next week! I think it will be a really good way for you and your team to connect.", she begins. "Yes, I'm also very excited. Thanks again for coordinating it and getting us those free spots." "My pleasure! It's fantastic that so many of the group have taken you up on the offer. They have asked us to be there about six thirty a.m. to get the hall setup and such." "No problem" I say, thankful that she apparently didn't notice me checking her out in the meeting earlier. "We'll have to stay late to help clean up as well" Megan continues. "No problem. We should have plenty of hands at that point to make quick work of it," figuring I can count on many of my team to chip in after a day away from the office. "I'm very curious to hear what they all think about this style of session and the agile methodology," I say, working to keep my focus as Megan switches her crossed legs, causing me to glance down at her legs. "Yes, I'm curious too," she says with a smile. "Maybe we could debrief after the clean up over a drink at a nearby lounge that I know?"

Did she just ask me out for a drink? No, it's nothing, she's just very engaged in her work and wants to discuss how the training went. Hum, I'm not sure, I think she might have caught me looking at her and liked it. Could she be like me, a sexually frustrated married professional looking for something more to life than work? No, it's nothing. Things like that don't happen to me.

"Sure, that would be great to catch up while it's still fresh. What did you have in mind?" "Well, there are a number of fun places within a few blocks of the conference center. My favorite has a very cool atmosphere and is only two blocks from the training facility. Maybe we could just walk over when we're done. Let's play it by ear and see how the day goes," she adds casually. "Sounds good" I say, "Looking forward to it."

Not clearly sure if I had just been hit on in my office, I was still enjoying the fact that they hottest gal in the company had just asked me to join her for a drink after next week's training. The fact that she had asked me behind the closed door for my office was interesting. Was it just that she wanted to be discreet about discussing the training opportunity for my team? Or was it that she didn't want anyone to know that she had asked me out for a drink after the training? Secretly hoping for the latter, I thanked her again for arranging the training and was looking forward to the full day's events. She rose and returned the chair to its original spot, turned her back to me and headed for the door. It was impossible for me to not look at her cute bottom, but as she reached for the handle she peaked over her shoulder and caught me in the act. My eyes popped to hers, and a smile spread across her face, "I look forward to hearing just how open-minded you are." She says as she closes the door behind her.

I hadn't felt so sexually charged in many years. It was as if a residual electric charge was pulsing through the room as I worked to process what has just occurred. I was getting quite hard, possibilities running around in my head, both of them very interested in all fun things that Megan might bring to the near future. The rest of the work day would be shot unless I could get her off my mind and release this sexual tension that was building. Thankfully this building had a basement that was nearly empty but fully finished, including a men's locker room. The toilet stall there was a perfect place to stroke my cock to a nice orgasm. I quickly headed for the elevator and upon reaching the basement found it deserted as usual. The locker room was the same, quite, so I quickly entered the stall and unzipped my slacks, letting them and my boxers fall to my ankles. My cock was semi hard in anticipation and took only a few strokes to reach full engorgement. I'm looking down, watching my head grow as I pull my foreskin back slowly, a bit of pre-cum glistening at the tip. I use my other hand to gently rub that slippery lube around my head making it grow even larger a turn a deep shade of purple. I begin to stroke it rapidly, so horny now that I don't want to wait for release any longer. I raise my free fingers to my mouth and taste the salty lube, licking between two of my fingers as if they were Megan's pussy lips. Then I take them both deep into my mouth and suck them clean as I thrust my cock deeply though my other hand. My mind filling with Megan's beautiful body, wishing she were here, bent over in front of me with her skirt up around her waist, panties at her knees and my cock buried in her pussy. Ahh, that did it, I can feel that familiar sensation building in my mind and balls. I keep stroking quickly, straining to hold back the cum, building the sensation until I can't restrain it anymore. I moan as the release comes in a wave of body shudders and a pulse of cum shooting across the stall, and then another. I slowly stroke my cock and release the remaining juices and my eyes close and my head roles back enjoying the waves of calming pleasure. I languish, wishing for more, with Megan, with someone. Maybe there will be something soon? But the day and the priorities, and all the rest start to slowly intrude into my stream of consciousness as they always do. Time to clean up this big mess of cum and get back to work. Good thing the class is only a weekend away, or I'd probably be down here again more than once.

The day of the seminar I arrived at the prescribed time to help setup the event. Megan has arrived before me and is already talking with the event director. She's dressed for the physical labor of setup and teardown, but still managed to look sexy in tight fitting jeans, black blouse and calf-high black boots with a low heal. Her back was to me as I entered the main hall so I was able to fill my eyes with her sweet backside as I slowly walked to them. Wow, wouldn't it be fun to take her from behind..., focus Jeff. I was greeted with a lovely smile and a friendly hand to my upper arm as I announced myself. "Thanks for being her so early to help," she says. "I know it's a long drive for you." "No problem, I'm a morning person and very excited for today's events. Thank you for taking such an interest and doing all the work to get this going for me and my team." Her gorgeous smile was mesmerizing and abruptly interrupted by a rather obtuse and homely building manager beginning an oratory on how the hall needed to set just so. Time to get to work.

Mostly on our own we moved tables and chairs, in multiple rooms, into position for the expected 200 attendees. I hadn't seen Megan much during the busy morning and as the event began she joined my team and me, all seated together for the opening session. As the day progressed it was fun to watch her interact with my team and other in the group activities. She was extremely outgoing, not afraid to jump up and be part of the interactions or presentations. She was very confident and it was oh so very sexy.

The day was full of breakout sessions and again I didn't see her much until around lunch time when I had gathered my team together for some early feedback. This was more about team building for my new group than anything else. Even if the sessions were mediocre, we would be able to review them as a team and have time to bond over lunch and closing discussions. Megan was interacting well with my team of technicians, making friends with every conversation. Again, very attractive to watch.

As the day was wrapping up, I began getting excite about the possibilities over a drink or two with her after our clean up duties were done. I had specifically not planned any after events for my team with the excuse that I had a long drive home and work the next day. Many of my team helped out with the cleanup however and chatted about the day and what to do after. Most had to leave but a few were making plans to get together for a beer nearby. I declined politely with my pre-planned same excuse, but was now worried that they would be in the area where Megan and I would be going out to talk about the day. Would she invite them to join us? This would be an interesting view into her thoughts for our time this evening? She also politely declined stating that she had already made other plans. Wow, she did want to be alone with me. Was it possible that she was interested in me for more than just work? It sure seemed as if the possibility was there. My mind was racing. How do I handle this one? Play it cool, she's a co-worker, you could be wrong and making advances could be a very bad career move. Be your friendly, outgoing self and let her push the envelope if she is so inclined. Yeah, that would have to be the way, as my job was more important than my sexual desires. We'll have wait and see how the evening turns out.

How incognizant, at that time, how much this line of thinking would be put to the test over the next six months, and how often it would be tested to millimeters of the edge.