It wasn't right away that I fantasized about my boss. When I was interviewed by her for the job I ended up earning, the thought of having sex with her never remotely entered my mind. Even so, when I did develop those erotic feelings, I never sought anything really passionate or at all romantic. I didn't so much as want to even kiss her. By that point, all I wanted was to catch her in a good mood, fuck the hell out of her (preferably on her own desk, as my fantasy always went) and not put my job at risk.
I'm not sure at what point I began to desire to plug my boss. While I respected her immensely from the moment she hired me, I felt no physical or sexual attraction for her for at least the first few months at my new job. Actually, with the job, I inherited my own staff that was comprised mostly of females, so my honest ambition was to bang a couple of the select attractive young ladies who reported to me. My boss Renee, on the other hand, was old enough to be my mother. I pegged her as certainly pushing 50 and later found out she was past that milestone at 54. She didn't necessarily look young for her age either. It's not that she wasn't attractive for her age, though; she just wasn't especially hot - well, at first, anyway.
The more I worked with Renee, the more I respected her. She was a very good boss, one who let me run my department and gave me the tools and support I needed to do the job. It wasn't long until I started to trust her significantly on a personal level, too. She seemed to take a sincere interest in my personal growth as well as my professional development, making efforts to build what was feeling like a friendship. At this point, she became one of my favorite people in my life, and somewhere around there followed the burning lust to have sex with her.
Renee's five-foot frame didn't inherently exude sex appeal, but she genuinely did well with what she had. Her short, curly blond hair didn't make her look any younger, but I started to notice that some days she wore it just right where her curls made her look not only professional but sexy. She wore black, thick-framed but narrow glasses that hid her bright blue eyes but were stylish. Her style was what really helped her cause, as her humble pale white frame was always dressed classy. Some days she'd wear just the right skirt or shoes that would make me wild with an unquenchable desire to bend her over her desk right then and there.
As time went on, I began to suspect that the growing sexual attraction was mutual. After all, to an older woman like Renee, I couldn't have been too unattractive. Still shy of 30, I was in shape, fairly tall and, like Renee, did the best I could with what I had. My hopes began to peak when Renee got even more comfortable with me, even flirtatious. I started to entertain the idea that I may actually fuck her - then, I'd remember she was a strict professional with a husband and four children. Still, it was fun to think about, and it was harmless to be cautiously flirtatious back to here, even if I were misreading her signals.
Friday, September 12 was the date of my performance review. It was also the day before Renee left for vacation, which would be followed by my own vacation. It was the last time we would see each other for a couple weeks, so we wanted to make the most of the time. It was also the day I first fucked my boss.
I'd later find out that the timing of the performance review - on a Friday before Renee went on vacation and at 5 pm no less, when the office was virtually deserted - was by Renee's design. The setting was right; if the sparks flew, then all the better. Normally I would have been annoyed with having to stay late on any day, let along on a Friday; for Renee, though, I would do anything.
It had been a very stressful day, which was pretty much the norm in this job. Inter-office politics made both Renee's and my jobs more difficult than they needed to be on most days, and we'd often debrief and de-stress in Renee's office at the end of a particularly stressful day. It was these meetings where I'd often detect what I construed as mild flirting from my significantly older superior.
The meeting started with our usual venting and small talk before transferring into my review. Needless to say, I scored high marks. Renee said a lot of very sweet things about me, which again had me thinking about lying on her desk while she rode up and down me. I clearly started to drift there, because Renee called me out.
"What did I just say?" Renee said.
"Oh," I stuttered, "Sorry. I was just . . . thank you for the kind words," or something along those lines.
Our conversation then turned toward Renee's upcoming vacation. I found out that my boss was going with just her kids, leaving the hubby behind, which I found strange and politely questioned her on. Renee then spoke freely of her strained relationship with her husband, including in no uncertain terms that she hadn't "been laid in four months." Yes, we had gotten pretty comfortable with each other, but even so, that comment took me back. I must not have been thinking clearly when I responded, but in retrospect, I'm thankful for whatever state of mind I was in.
"That's too bad," I said. "I would totally sleep with you." I remember the words exactly. I also remember how Renee's eyes grew so wide that I thought they'd pop. My heart stopped as I considered the words that just came out of my mouth, wondering how bad a thing I had just done. But then an unmistakably seductive grin spread across her face. My dread turned instantly to hope.
"Well," my increasingly sexy boss said, "as I said when you were zoning out there, despite your outstanding performance, there's no room in the budget for a raise . . . but maybe we can get creative and think of something else to serve as a reward for your work."
It was as if I were living out a porno. I turned red. My heart was pounding. I was as nervous as I'd ever been, but there was no way I was bungling this once-in-a-lifetime opportunity.
"What are you doing tonight?" I asked candidly, barely able to hide my excitement as I considered the very real possibility that I'd be fulfilling my fantasy and sleeping with my boss tonight.
"What are you doing right now?" Renee countered, raising the bar of my expectation where just a second ago it dared not go. She was grinning from ear to ear as she continued, "We're still holding your performance review, after all."
For the next several minutes, things were kind of a haze when it comes to remembering them. Very little was spoken after our clearly implied consent to have sex right there in Renee's office. Following a blur of activity, including Renee's standing up from her chair, which she pushed back with her ass, and my coming around to her behind her desk, we wasted no time proceeding with what very obviously had played in both our minds previous to this evening's interview.
Renee unbuttoned her blouse as I unbuckled my belt, now standing behind her. As I loosened my khakis, I studied Renee's outfit. As I eyed her from her feet to her head, there was no doubt in my mind that our scheduled meeting today was strongly taken into consideration when Renee picked out her wardrobe this morning. She sported roughly four-inch black high heels, separated from her pinstripe pencil skirt by her short but slender legs. The skirt rode two or three inches above her knees, leading up to her round ass and firm hips. Noteworthy for her age, she had maintained her womanly hourglass shape well, aided by boobs that, I now noticed for the first time, were rather generous for such a small frame. I could hardly wait to touch them and see if the felt as good as they looked.
After unbuttoning her royal blue blouse, Renee turned around, revealing her black lace bra, which was more evidence that she had planned for this best-case scenario. We exchanged compliments as Renee reached under her skirt and pulled down an equally sexy pair of black lace panties, which she let fall to her ankles.
By now, my heart was pounding as hard as ever. I couldn't believe that I was about to fuck my boss. It wasn't the most debauched thing I'd ever done, but it certainly belonged in the upper echelon of my sexual exploits. My cock was so hard that it was poking up out of my boxers, giving Renee a sneak peek.
"How do you want to do this?" I asked awkwardly, completely stonewalled as to how to continue. It's not like I'd ever fucked my boss before. Renee stepped out of her panties before dropping to her knees as she insisted we'd just continue with the performance review process.
Once on her knees in front of me, my boss pushed my pants and boxers down to my knees, took my shaft in her small hands and stroked it briefly. Then she moved her hand forward, opened her mouth and took me in.
I moaned loudly the second the tip of my cock touched Renee's tongue and slid deep into her mouth. I caught myself and stifled my audible expression of pleasure, realizing it was only 6:30 pm and that others may be around, but Renee, who often worked late, was quick to calm my nerves.
"It's OK, baby," she said, pulling her mouth away for just a moment. "Everyone else is long gone." I knew that there was evening security in the building, actually, but Renee added that security never comes back to the administrative offices. Pleasure gave way to caution, and I sighed and moaned again when Renee took me back in her mouth.
For the next five minutes or so, Renee sucked my cock, demonstrating expertise that came with her age that I had never had the joy of experiencing until that time. There I realized I was in for a real treat, even aside from the fact that I was going to plug my boss. Renee would be the oldest woman I'd be with by more than a decade, and all those years meant all that sexual experience. In truth, Renee had been having sex for longer than I'd been alive.