More than a year ago, I posted a story that shared a fantasy of mine that I had otherwise kept to myself for the past few years, namely, fucking my older female boss over her own desk at work. While I found the woman, Rene, anything but sexually attractive when she first hired me (if for no other reason because she was in her early 50s and I in my mid 20s), as my respect for her grew over the next several months, so budded a very real desire to plug her good and not adversely affect my job. I started to see her in a whole new light and realized that, for an older woman, she was pretty sexy.
Beside her age, I noticed she was actually sort of my type. I always gravitated toward more petite women, and Rene stood no taller than 5'2" and was thin with pale white skin. Despite her frame, she had a nice, firm rack that I desperately wanted to touch, and her ass was as round and sexy as they come on women in their 50s. What she did to accentuate that body is what really helped attract me to her, always wearing fashionable blouses and skirts, accompanying her outfits with the right pair of high heels and making sure her short blond hair was perfectly done. Her stylish glasses were perfect for not only making her older face appear more youthful, but also for somehow bringing out, not obscuring, her pretty blue eyes.
Rene had supervised me for the better part of three years before the company let her go without notice and without any specific reason to give her, but the severance package certainly softened the blow, I'm sure. As Rene left my life that day, so did my unrealistic hope of ever banging her. No, I never really thought it would happen, but it was fun to think about, so fun that I wrote about it and never stopped fantasizing about it.
A year after Rene left my life, I was chatting with a co-worker in my office one afternoon this past April. In the course of my conversation with this female employee, who has asked to remain nameless in this story, I came to find out that she was the niece of Rene, who had actually referred this girl to my company for a job in the first place.
Upon finding out that my co-worker was related to my former boss, I also discovered that Rene was recently divorced. It was sad to hear, but I couldn't help but wish Rene hadn't been attached when I was seeing her everyday at work back in the day - as ridiculous as I thought it was that it would have changed anything between us. Still, like I said, it was fun to think about.
Now, I may or may not have slept with this particular co-worker on at least one occasion, so when I asked her how her aunt was doing, one of the things she said was, "Of course, I never told her about that one night we had," she laughed. "That would probably just make Auntie jealous."
"Jealous?" I quickly responded. "Jealous how?"
My friend seemed uncertain how to answer that, but she said something along the lines of, "Please, Auntie had such a thing for you, the handsome young man on her staff. If you were having sex with anyone, she would want it to be her." She was blushing a little, clearly uncomfortable talking about this subject.
I let out a little laugh. "Truth be told, I kind of had a thing for her too," I chuckled again, trying to play it off as if I weren't 100 percent serious.
"What? Isn't she, like, too old for you?"
"Well, you know . . ." I responded, and the conversation continued like something along those lines. At the end of that discussion, my mind was on only one thing. Immediately I recalled that a long time ago, Rene had emailed me her personal cell number for a work-related issue. To my relief, I found that number in my trash bin and programmed it into my phone right away.
After determining that I would contact Rene with the hope of a hook-up, I did nothing for several days, paralyzed by nerves. What would I say? Did I really think I could just text or call my old boss, who was nearly twice my age, and think it would result in having sex with her? Hell, it would be super hot if it did, but anything short of that end wasn't really worth reconnecting with my former supervisor. And what would I say? And how did I know her niece wasn't exaggerating or, even if she wasn't, that Rene had actually been serious when she had somehow communicated a sexual interest in me?
After days of deliberating, I figured the worst case was an awkward conversation and I would never see or hear from Rene again. The best case, hey, you never know. Thank goodness I texted her.
I finally texted Rene under the pretense of seeing how she was doing following her divorce. I told her that I had talked to her niece and that her niece had implied that Rene might like hearing from me. As the conversation progressed, I used the divorce as my in, telling her that her new relationship status would free her up with the younger guys like myself. One thing led to another, and, even before I knew it, my heart was pounding as I nervously texted her back to tell her about my fantasy of fucking her in her office when she had been my boss. I was one favorable response from a dream come true.
Just two days after I texted Rene, we had a date set. I call it a date, since I don't really know what else to call dinner and sex, but it was a little weird to think of it as a date with someone in her mid 50s while I was still in my late 20s. Yeah, we went out to eat simply to catch up, but we had also decided to go back to her place afterward for no uncertain activity, making dinner more than just a casual affair.
