Five years ago, I received a phone call from a woman, whom I will call Rene, to set up a job interview with me for a position she had open in her department. I met Rene a few days later in her office, and if you had told me then what this woman would be to me just four years later, I would have never believed you. At the time, I was just looking to land a job that would provide me the security I needed. I never imagined I would so much as lust after her in the least bit, let alone fulfill that lust and then some.
At the end of an interview that lasted about a half hour, I had landed the job. I was very happy, not only because I got the outcome I had hoped for, but also because my experience with my new boss was really positive. As any employee knows, your supervisor can make or break your work satisfaction. Rene appealed to me because she was clearly very intelligent, honest and down-to-earth. I knew right away that I would like working with her.
What I didn't know right away is how sexy I would come to find Rene. In fact, those inappropriate thoughts never even entered my mind for the first several months I knew her. At the time, I was barely in my mid-20s, separated from grad school by just a year. Rene, on the other hand, was literally just about twice my age at that time, pushing 50. That fact alone made me never think about what it would be like to fuck my boss, but even if I had been attracted to older women at the time, I'm not sure Rene would have gripped me. While she was petite, which I liked, and she always wore fashionable tops, skirts and high heels, which made her look classy, she didn't look young for her age, and her short blond hair, aging pale skin and scrawny frame didn't make her objectively attractive to me at first. That perception, however, would dramatically change over the course of the next few years.
Regardless of any lack of physical attraction, I very much admired Rene as my leader over the coming months while I worked closely with her. I'm not even sure when and how it happened, but as my respect for my older female supervisor increased, so did my attraction to her sexually without my even realizing it right away. Before I knew it, Rene was holding meetings with me in her office while I was thinking about how it might actually not be terribly gross if I were to, say, bend her over that desk and fuck the shit out of her until I came deep inside her.
Those thoughts, over time, turned into full-blown fantasies, which turned into a desperate wish that I could actually have hot sex with my older supervisor. Some days, I couldn't even be around her without sporting a bulge in my pants if I wasn't careful to control my wandering mind. It was funny how that short, styled blond hair all of a sudden seemed sexy, how her bright blue eyes seemed to shine through her narrow, thick-rimmed glasses, which gave her that undeniable professional sexy look. Throw in the stylish clothes, the tight round ass and firm-looking breasts that I began to notice on that petite frame, and all of a sudden a woman who elicited no sexual desire from me previously had all the right qualities to star frequently in my fantasies.
Rene ended up leaving the company suddenly and unexpectedly about two years ago, but I didn't stop thinking about her. In fact, not having her around only further frustrated my desire to plug her to the point that I actually wrote and posted a fantasy story about how I would have imagined a sexual relationship's developing between Rene and me. Over the next year or so, I would revisit that story often, all the while having no contact with my former boss.
Even when I worked for Rene, I never imagined my fantasy would become reality. After she left my life, it didn't even make sense to think about. However, everything changed about a year ago.
I've already posted two accounts of my reconnecting with Rene, so I will simply summarize: after I conversed with a mutual friend of ours, I discovered that Rene was at least as attracted to me as I was to her. I also found out that Rene had recently gotten divorced, so I figured I had every reason to give her a call (once I found her number) to see how she was doing. After successfully and with surprisingly little difficulty steering the conversation toward her newfound freedom to hook-up with a younger guy like myself, I was in-that is, in the metaphorical door and in Rene's literal body.
Rene and I had sex that first night we reconnected, marking the first time I ever railed a woman that much older than I. In the coming weeks, we met for increasingly passionate affairs fairly often - since, needless to say, the actual experience lived up to my expectations so much so that I yearned for it more and more. With Rene's age and experience came some really pleasurable sessions with the older woman, not to mention the fact that she used to be my boss, which multiplied the enjoyment factor by a dozen.
Not too long into my fling with Rene, I managed the nerve to share with her my dirtiest fantasy, which was inviting another man into the bedroom to double-fuck Rene. I had experienced a devil's threesome with two other girls in the past and thought Rene was a prime candidate to receive that mantle. While she didn't exactly jump at the suggestion, she didn't rule it out either, which was all I could hope.
After a couple months, though, my trysts with Rene came to what seemed to be an abrupt halt. I wondered if it had to do with my prior proposition. However, as it turned out, Rene had taken a lover her age and didn't have much time anymore for her younger man on the side. She didn't tell me about this change in her life, though, until one night when she unexpectedly asked me over to her house. When I asked her the reason for the impromptu invitation, all she texted back was "Double." That one word was all the convincing I needed.
That night, I would meet her new boyfriend, an older gentleman named Rob, who then double-teamed Rene with me in Rene's bed, finishing off the party by double-penetrating Rene until I came in her pussy and Rob came in her ass. During the drive home late that night (with work looming the next morning), everything felt surreal, like I was having a dream. It never really sank in that I had slept with Rene in the first place, let alone that I had just sandwiched her, which had been my ultimate fantasy. Sure, the double penetration hadn't been done on her desk in her office or in a board room like I had always imagined, but I could certainly still check it off my bucket list.
