About a dozen years ago I started working at an international company at one of their offices in the US Midwest. The team of ten people worked closely and grew to know each other through hours sitting together. In situations like that solid, long-time friendships can develop. Other relationships can develop, too.
Jenny began at the company when I did. She was engaged to some guy. I swear the only time I saw him was in a really neat picture of Jenny riding on his shoulders at some sports event, a picture she kept in her cube area. Those two really appeared to be a fun couple, but Jenny was most often reserved and serious. In the picture she was smiling and goofing around. I wanted to find out more.
Jenny aspired to be successful professionally, and that seemed to guide her interactions. Over time she opened up and her business-like demeanor loosened up. She even became a bit flirtatious. After two years it became apparent she came across as prim and proper but there was more going on. I just knew it. Beneath that demeanor was a WILD woman, I was positive.
Unfortunately, Jenny followed a dream to move to California. Her engagement had fallen apart – hell, I didn’t think he was deserving anyway! Once out there she and I kept in touch for a couple of years in which she shared tales of dating or fending off guys. She continued to flirt openly. Yes, we were different in a few key ways and never got beyond the talk even though it seemed like the potential was there.
As luck would have it Jenny eventually returned to our company only this time working in another city. But she WAS back and in the same division of the company as me. Hmmm...good, I thought. But damned if she didn’t get engaged AGAIN though. Yes, busy gal. She could attract the guys; they’d fall for her every time. However, after just a few months, this engagement fell through, too. Jenny was always full of surprises.
In our jobs we now attended the same meetings at various locations. We also took time helping each other’s careers, plus held late-night discussions wherever we were. I did try to put the move on to her a couple of times but was rebuffed in a nice, consistent way. I never pressed the issue, but she kept teasing me along and, being a normal horny guy just ate it all up!
We shared stories at every opportunity with no one in the company any wiser. She was serious about being successful, and I wasn’t going to fuck that up. We continued to talk about relationships, family, and frankly, things of a sexual nature. I gave up hope of something happening but it was still fun as Jenny had a smart mind but more importantly dirty and very naughty. I could learn some things from a woman’s perspective. Cool, I thought.
Timing again worked on my side when we were promoted to a similar level and scheduled to attend the same three-day training/celebration. The celebration session was the kind where money did not matter and the company spent freely - first class all the way AND the perfect setting for something to change in my admitted lust for Jen. This was now six years after we first met. So we both flew into the same city to join hundreds of other new executives. I was at my most business-like behaviour, of course. But Jenny seemed to be much friendlier with me than before. Or maybe it was just my male ego?
The first two nights of the session there was plenty of drinking, networking and bullshitting going on. Late at night she and I gathered in her room to talk: I did my usual pop-psychology about her dates, boyfriends, and fiancés. And she did her usual tease that drove me a bit crazy. She innocently made sexy remarks and seemed to shed clothes while we spoke, “Oh, I’m hot do you mind if I take this sweater off?” or “I’m going to put on my jammies but you know I only wear a t-shirt, is that ok if I get dressed for bed now?” Not fair!
Finally, the anticipated blowout party night arrived. The company rented a sports dome and had a half-dozen open bars, games, and fun going along with a live band. It was a carnival atmostphere and I was feeling no pain after a few trips to the bar or grabbing drinks off countless trays being carried around. I challenged Jenny to a few games – she being very competitive – and we ended up tied in total wins. Jenny said she would figure out a tiebreaker later. I didn’t know what she meant at the time.
We left the party during the night for a short bus ride to take a tour. On the bus we had a few more toddies until reaching the destination. On the way everyone toasted our success and, at the right moment, I kissed her cheek. She just smiled.
Once at the location we took a series of three escalators up to the private tour’s start. On the second of three escalators I was a step below her and Jenny started rubbing her body, her ass, all over my chest. Her TIGHT JEANS felt good. She bent her neck and head backward to whisper in my ear, "Tonight is the night." I was a bit stunned. “What does she mean?” I thought. It was so damned noisy I wasn’t sure – but my mouth went dry anyway. I said nothing but stared up at her. She watched my reaction grinning.
Next we were part of a same small tour group and, as the tour progressed, Jenny pulled me to the back at each stop, stood in front of me, and rubbed very deliberately backwards. I couldn’t react (though I was having a hard time, so to speak). She gyrated her NICE ASS on me, grabbed my crotch casually, and whispered in my ear and such. I just pretended to listen intently to the tour host. But my COCK was HARD most of the tour!
The tour ended, we got back to the bus, and Jenny led me to the very last seat on it. As the bus roared back to the party she started messing with my belt and zipper. I still wasn't convinced she wasn’t teasing me more, her most devious flirt. I had been rebuffed before. I played along.
Once inside back at the main party we walked around a minute or so when she told me to grab some wine and MEET HER BACK IN HER ROOM a little later. Then she took off. I still couldn’t believe it, but I was sure those were my instructions. Fuck, this was the night!
I made it back to the hotel about a half hour after she had left the party. I was still not sure this was really happening but my cock was pretty positive and had been twitching for a long time. I hustled through the crowded lobby and entered the elevator with drinks in hand. As the doors opened onto her floor I walked down a couple hallways to her door, casually double-checking both ways in the hall for observers. No one there. Good. I kick-tapped the door’s bottom and it opened, an arm extended out, a hand pulling my sleeve and me inward. The door closed quickly behind.
