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.
By the time Renee finished blowing me, I was more than ready for a good fuck. However, she was the boss and didn’t let me forget it, stating I now had to pass an “oral exam.” What she was implying was obvious. She got up from her knees and then pushed herself up onto the desk, facing me as she sat on it. Then she leaned back, holding herself up by supporting herself with one arm while she used the other hand to hold up her skirt and reveal her clearly moist pussy between her legs that were spreading.
My fantasies of Renee never involved going down on her, but in this moment of reality, I was happy to comply. Again, she was the one signing off on my paychecks. Obediently, I knelt beside the desk, in front of my boss’s taint and leaned forward as Renee lifted her right leg up into the air, over my head and slid her left leg farther out along the surface of her desk. My peripheral vision was obscured by Renee’s skirt, so I had nothing to be focused on except for my boss’s pink pussy.
I went right for it. At first, I used my index finger to locate the exact spot. Then, using that same hand to more or less spread Renee’s pussy, I pressed my mouth against that spot and began to eat out my 54-year old supervisor. Her moans led me to believe that I was performing my task well, as did her increasing wetness. Giving my boss oral may not have been on the job description I signed off on, but then again, I recall there was a point that included being willing to go above and beyond my expected duties.
I licked Renee’s twat for a little longer than she’d given me oral, maybe eight or 10 minutes. About halfway through, she lowered her leg and rested it over my shoulder, still holding up her skirt as I went to town on her cunt. The heel in her shoe poked my back as my tongue prodded her insides. My boss squirmed and moaned throughout my pleasuring her and assured me that I was doing a good job, calling me “sweetie” and “honey” a lot. The affection was kind of weird coming from my boss, but, then again, eating my boss’s pussy wasn’t exactly standard either.
When Renee said I had done enough with my mouth, I pulled back and wiped my lips and chin. The scent of her pussy was strong in my nostrils, and I was fine with it. With both our engines primed, my boss and I were ready to lay aside months of sexual frustration.
“Now for your real performance review,” Renee said seductively, lifting both legs straight up in the air and propping herself up by her elbows behind her. My cock was more than set for what would ensue. I stepped up, my head now between my boss’s high heel shoes that were held up in the air, my hand on my cock as I prepared to enter my boss like I had fantasized about for months leading up to this unbelievable experience.
With one smooth motion and hardly any resistance, I slipped my cock, slick with her saliva, into my boss’s exceptionally wet pussy. On that first stroke, I went balls-deep in her, sliding my whole length inside my sexy supervisor. Renee moaned while I forgot to breathe. As I started to fuck her, Renee rested her ankles on my shoulders and slid onto her back, her arms slipping straight out on the desk until her fingers gripped the edge over which I stood.
I put one hand on Renee’s hip, pinning her skirt against her hip while my right hand held her ankle, which stayed suspended over my right shoulder. As I adjusted to the thoughts and sensations that came with having sex with my older female boss on her own desk, I was delighted at how surprisingly tight Renee’s pussy was. It was much tighter than I had expected for a woman her age, possibly betraying that tonight’s tryst was the result of years of dissatisfaction with her husband.
I immediately felt sweat on my forehead and also remembered to breathe as I slowly pulled out of and pushed into my boss, who’d never looked hotter than she did in that moment now that my dick was in her. We were both moaning in unison now as I fastened my gaze on my stiff cock’s disappearing inside my boss’s pussy, then sliding back, only to steadily dive back in. I watched my cock go in and out of my boss for a moment before my eyes traveled to Renee’s heaving boobs, at which point I released her ankle in order to give her left breast, still veiled by the lace bra, a good squeeze. It was nice and firm, as I’d hoped. Then I slid my hand over to the right breast, this time under the bra, giving this tit a firmer squeeze. I was not disappointed.
I squeezed my boss’s boobs for a couple minutes while I started to fuck her harder. My balls slapped against her taint while the force of my body’s smacking against hers caused her to slide up the desk. Her grip on the edge of the desk, which tightened to the point that her knuckles were white, kept her in place for the most part, though, despite my increasingly intense thrusts into her as I plowed her.
By now, I was sweating so much that my dress shirt was sticking uncomfortably to my back. Relentless, though, I pushed harder and faster into Renee as neither one of us said a word amidst our fantasy’s coming true.
About halfway through our intercourse, we decided to switch it up. A couple minutes before, though, I put my right hand back on Renee’s ankle and held her leg in place with my arm as I nailed her. Around that time too, Renee reached up with right hand and pulled on my tie, begging, “Fuck me harder!” I’d never heard my boss use such foul language before, but I did as I was told.
When Renee released my tie, I let go of her and reluctantly pulled out of her. It wasn’t for long, though, as Renee simply hopped down, turned around and bent over her desk, just as I had dreamed. I looked down to see Renee’s heels scratch against the carpet of her office as she spread her legs farther, preparing for my entry.
“Make your boss your bitch!” Renee said. Those hauntingly hot words got me going like few else have to this day. Renee reached across her desk and held the opposite edge while I hiked up her skirt and guided my cock back into her cunt.
With my cock sheathed in Renee’s pussy, I quickly removed my tie and shirt, as the damp clothing was making me uncomfortable in the poorly ventilated office. With the attire discarded, I put both hands under my boss’s skirt and onto her bare ass as I proceeded to fuck the hell out of her doggystyle. I started hard and steady but somewhat slowly before building up to harder fucking, sinking my nails into her flesh as I slammed into her, my balls slapping against her clit. Renee’s nails scratched against her desk as she moaned loudly, her body sliding forward on her desk as she now propped herself up by her elbows.
“I bet you love fucking your boss!” Renee yelled as I nailed her over he desk. “Fuck me faster!” I was slamming into her so hard that her files and office supplies were shaking on the desk and I was breathing so heavily that I didn’t manage a word in response to her.
“Faster!” A pencil cup fell to the floor, spreading writing utensils in every direction. “Faster!”
“I’m going as fast as I can!” I finally managed. Renee laughed gleefully.
“Don’t stop!”
The room grew very hot, and were both sweating profusely at this point. By now, Renee was matching my thrusts, pushing back as I pushed forward, ensuring that my cock was going as deep inside this older woman as possible.
Just as paperclips, papers and other shit began to fall off Renee’s shaking, creaking desk and onto the floor, the office phone rang. Deterred for only a second, I barely broke my pace as I continued to grab my boss’s ass and nail her hard, figuring Renee would let the call go to voicemail. To my shock, she picked up the receiver.
“This is Renee. May I help you?” I was shocked, instantly ceasing from my wild thrusting into this amazing woman. Not only was I totally surprised that she would take a work call during naughty sex, but I was amazed how well she was hiding how out of breath she was – not to mention that she was being fucked by her employee.
“We do provide those services,” Renee said expertly. “I’ll be on vacation next week, but let me give you the manager’s contact information so he can arrange a meeting with you.” She then gave my own contact information before wishing the caller a good weekend and then hung up. I was still in shock.
Renee told me to expect a call from a woman named Laura on Monday, switching perfectly to professional mode despite the fact that her hair was in her face and, oh yeah, my cock was in her pussy. I was astounded by this woman’s sexy professionalism.
I managed only to trail off in response to her, not knowing how seriously to take her. I was starting to go a little soft, out of confusion if for not other reason. Finally, Renee laughed.
“Well?” she said. “Are you done? Or are you going to cum inside my pussy?” There it was. It took a minute, but I got back to screwing my boss over her desk to the point that it was shaking again. We were both moaning together in no time as the steady smack of flesh on flesh joined the creaking of Renee’s desk to fill the room.
Toward the end of our intense intercourse, I leaned forward, reaching into Renee’s unbuttoned shirt and putting my hands on her boobs as I continued to fuck her pussy. I pushed her bra down a bit so I could again get the full experience and was still not disappointed. By now, we were both glistening with sweat, and various office supplies littered the floor. At last, I felt Renee’s pussy constrict around my plunging cock, which, along with her yell, indicated her orgasm. Her shrill cry would have surely been heard by anyone nearby, but I didn’t care. In fact, my orgasm wasn’t far to follow. Within a few minutes, I was spraying cum deep inside my boss as I kept her bent over her own desk, sufficiently making her my bitch like she had challenged me. I couldn’t contain my own moan as I unleashed several spurts of cum until my full load was in her womb. There I realized another advantage to nailing a 54-year old woman: no risk of pregnancy.
