Reconnecting with Rene

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.

Honestly, the dinner was really awkward. I didn't want anything more our Rene at that moment than to bang her and hope it was as fun as I had always imagined. It's not that I didn't enjoy talking to her; actually, it was nothing that was her fault at all. I just felt really uncomfortable talking to a woman old enough to be my mother when all I wanted to do with her was bend her over and fuck the hell out of her. The fact that my desires were out in the open didn't change that weird dynamic I felt.

What didn't hurt, though, was Rene's outfit. We had planned to dress like we did for work so as to enhance the fantasy. I came to dinner in khakis, a button-down shirt and a tie. Rene wore a short, tight black skirt, a button-down blouse and black high heels that were about three inches. She had just gotten her hair done, as she told me, and her blue eyes seemed to have an extra sparkle coming through those black-rimmed glasses. She was as excited as I was but didn't seem quite as nervous.

After dessert, we took separate cars to Rene's house. Originally, we planned to do the deed at my apartment, since Rene still had one of her daughters living at home. However, when Rene learned that her girl was staying at a friend's house tonight, we changed the location. We figured it would be a little more private in a house as opposed to an apartment complex.

Up to this point, I was anxious that this whole thing was a mistake, that it wouldn't come close to living up to what had ran through my head for the most of the last three years. Maybe it was because Rene was much older than I, but not only did I feel awkward pursuing intercourse with a woman whom I had had a strictly professional relationship with prior to this week, but I felt like a virgin all over again, like it was my first time. The confidence I had built up sexually, especially over the past couple years, abandoned me as I sat at Rene's kitchen table and watched her pour us each a glass of wine.

Some more superfluous small talk ensued as we imbibed out beverages until the drinks were gone and Rene, thank goodness, cut right to the chase: "It's not my old office desk, but do you think this table will do?"

"It will do just fine," I said. I could feel a goofy smirk on my face that I couldn't control as I stood up and placed my empty wine glass on the nearby counter. It was like Rene's words were magic, dispelling my nerves immediately once I realized we were about to really do this hot, decadent act. I think my cock was fully erect before I was standing up straight.

Rene looked around quickly to make sure all the curtains were drawn. We couldn't have any nosy neighbors spoiling our fun! Next, she hit the dimmer switch so that the light was low, just enough so we could see and enjoy everything we were about to do. All that was left was for Rene to clear the table, which just had a napkin dispenser and salt and pepper shakers, and we were ready to use the piece of furniture for the best thing for which it would ever be used.

This hook-up with Rene, with such a unique context in my experience, was very much a first for me, so I recalled other firsts in my past to help me carry through with it without any awkward incidents. I knew I needed to do anything but over-think the fact that my very vivid fantasy was about to become very, very real. Instead of letting nerves get the better of me, I let the excitement grip me, which helped me leap over any inhibitions I felt in regards to joining my body to this sexy older woman's.

Rene started by unbuttoning her blouse, not delaying but simply opening the whole thing from top to bottom, revealing a black lace bra. "Tell me exactly how you want it," she said, grinning as her eyes gleamed behind her glasses.

"Don't you be shy either," I said, almost unknowingly pulling at my own clothes frantically. We agreed on partial nudity to aid the office theme, so I removed just my pants and boxers, leaving on my shirt and tie, while Rene removed only her underwear, leaving the shirt on (but open, of course) and her skirt as well. She removed her panties first and carefully pulled them around her shoes, leaving the footwear on, per my request. Then she removed her bra, revealing to me, at last, those boobs for which I had longed, small but so round and perfect were they on her petite body, especially considering her age.

Cutting right to the chase, Rene turned away from me, facing the table and bending over it, resting herself on her elbows as she looked over her shoulder back at me. The rest was up to me.

My exposed cock at full mast, I stepped up behind my former supervisor and, first, pushed her skirt up her thighs and past her ass. I gave one of her butt cheeks a squeeze, wondering if one day I would fuck that ass, but such a request would be better at a later session, should this sexual element remain in our renewed friendship. Next, my finger searched for Rene's pussy and was greeted by confirmation that my old boss was every bit as excited as I was.

"You're as wet as I always imagined," I said to Rene as I pushed my finger into her pussy, costing my digit with her excessive juices. "I bet you're just as tight too." For that last part, actually, I didn't know what to expect. She was an older woman, so I knew she would be more broken in than the younger gals I was accustomed to fucking. I was well aware, though, and in much anticipation of how Rene's years of experience would make up for any wear and tear on her body.

Rene tilted her head back and moaned as I started to finger her, sliding back and forth slowly at first but quickly increasing my pace. She let me pleasure her manually for just a minute or so before she said, "Put your cock in there," her tone sounding like she was begging.

"You're the boss," I said, grinning as I pulled my finger out of her and wiped some of her juices on the tip of my cock, preparing it for entry. I was proud of my boss reference there and had always wanted to use it in a sexual context. Rene, on the other hand, was more interested in my getting to work on nailing the shit out of her sexy little body than my cleverness.

It was now or never. My heart was in my throat as I put one hand on my former boss's lower back and used my free hand to guide my cock toward that mature fuck hole. For the first time in my life, I would be joining my body to one that was beyond early 30s in age, and it was with the only woman with whom I had ever imagined doing such. My mind swirled with a mix of raging lust and unbelief as I worked the tip of my manhood into my sexy supervisor, eliciting a sigh from both of us as we only just began to fulfill our dream.

I cursed as I pushed the first inch of me into Rene, sinking both sets of my fingers into her ass as her warm, wet insides greeted and enfolded my cock. Rene moaned, scratching her nails against the table as I slowly thrust forward until all of me was sheathed inside of her. My head was swimming, and my heart was pounding harder than I could remember in a long time as this wonderful realization set in. With my balls touching my former boss's clit, I held tightly to her ass and ground up against her, for the moment enjoying the sensations of just being inside her.

Rene's pussy was tighter than I imagined for an older woman, leaving me not the least bit disappointed. As I held firm inside her for just another moment, Rene started to grind back against me, rotating her hips slightly but just enough to give me an additional rush. I couldn't wait to see what other tricks she had picked up throughout the course of her sex life, which undoubtedly extended beyond my entire lifespan.

In such a trance was I that I kind of had to come to my senses before I actually began to fuck Rene. The two of us seemed content to just grind on each other until I snapped out of it, at which point I looked down at my cock inside that tight, mature pussy and pulled back slightly. I could very evidently see streaks of Rene's juices on the shaft of my dick as it pulled back until just the tip was still inside her. Then I pushed right back into her, firmly and fairly quickly, breaking in her pussy for me as we both moaned.

After a few more deliberate thrusts like that one, I leaned forward a little more, pushing Rene down a bit and forcing her to spread her legs a tad more, her high heels scratching against the linoleum kitchen floor. Once we were positioned just right, I began to pump in and out of her at a faster and steady pace, which felt really, really good for both of us. It felt like I was in a dream, but I was really having sex with Rene!

Rene lifted her head up and looked straight forward as she moaned and encouraged me on. Now I was just getting past the initial disbelief of my good fortune to be actually fucking my old boss like I had often fantasized and was more and more able to just fell headlong in the wicked pleasure of nailing this divorcee over her own kitchen table. As I pounded her harder and faster from behind, that table began to creak and my flesh started to slap against hers as I thrust into her over and over again. The longer we fucked, the louder Rene moaned, but the quieter I got as I focused on giving it to her good. I swear, her pussy felt like it was getting tighter and tighter the more I plowed into it.

Rene's twat was dripping wet, squishing as I thrust in and out of it faster and faster. Rene writhed against the table, her nails leaving faint scratches on the surface as she took my steady pounding. As I fucked her, I had the presence of mind to finally see for myself if those boobs felt as good as I had always fantasized. Letting go of her ass, I slammed to the hilt inside her, reached underneath, pushing away her blouse, and grabbed a hold of one boob in each of my hands as I leaned forward and ground against her.

"Your boobs feel amazing," I panted as I squeezed them nice and hard before I resumed my thrusting motion in and out of her. Now I was leaning over on top of her, holding dearly to her tits and slamming myself back and forth into her body, rocking it forward with each push. The table creaked louder and even started to shift forward a bit as I drilled Rene from a lower angle, fucking her a little more slowly but harder and more deliberately, causing my balls to swing forward and slap her clit each time I buried my prick inside the warm confines of her womanhood.

"Oh! Oh! Oh!" Rene moaned with each push of my hips into her. Being this close to my mature friend now, I was beginning to feel really warm, causing my forehead to sweat and the skin under my shirt to become clammy. The breathing of both of us grew more and more ragged, and Rene's moans got louder and louder until she let out one big, drawn-out cry.

"I'm cumming!" she yelled, going rigid as he body rocked with an orgasm. I squeezed her boobs hard again and fucked her pussy as deep as I could right through her climax, causing her to shudder and spasm even more than she already was. Her cunt had a vice-like grip on my member, and judging by her moaning and convulsing, her orgasm lasted more than a minute until she at last indicated the waves of intense pleasure that were crashing through her body were subsiding.

In the passion of these moments, all my confidence was restored, to the point where, once Rene relaxed against the table after cumming, I gave her just a couple more thrusts before pulling out and asking her to roll over. While I enjoyed the doggystyle position over the table with this woman for whom I had no romantic feelings, I wanted to give her some room to kick those sexy legs while I fucked her before it was my turn to cum.

Rene, panting and sweating, rolled onto her back, her unbuttoned top falling open and giving me a full view of her heaving breasts. Wasting no time, I picked up her legs, holding them up in the air and resting them on either of my shoulders, in so doing, spreading her beautiful pussy. Perhaps still feeling the aftershock of her climax, Rene quivered slightly as I pushed my cock back inside her, not wanting to be apart from my former boss's pussy again until I had unloaded in it.

Rene and I moaned in unison as I sank all the way back inside her until my balls made contact with her taint. As I pushed all the way forward, my shoulders bent Rene's legs back with me, stretching her out nicely. Starting out, I wrapped my arms around my lover's legs, gripping her ankles just above her high heels with my fingers. Then I proceeded to resume fucking the mature 50-something-year-old lady deep in her delightfully constricted cunt.

As I thrust in and out of Rene, she gripped the edge of the table where her ass was and held herself in place. After a minute of my fucking her in that manner, she started to rotate her hips and grind up against me, working with me to maximize the pleasure for both of us. I assumed these moves were little tricks she had picked up along the way, as her sexual experience by far exceeded mine. The things this woman could do with her cunt and body were subtly but wonderfully unlike what the younger girls from my experience could do. I realized in that moment that what I was doing was more than just fulfilling a dirty fantasy of mine. I had an opportunity here for some serious, extended fun with this woman.

I slammed into Rene harder and faster as she urged me on, my arms wrapping tighter around her legs, my nails sinking deeper into her ankles and my shoulders pushing her legs farther and farther back until I decided to let go and, instead, latch onto her small but firm boobs again. I leaned even farther forward to squeeze those tits, causing Rene's legs to spread even more, her ankles sliding down my arms toward my biceps. All the while I continued to pound her tight pussy hard and fast to the sound of our moans and the creaking table beneath us.

At last, I felt my balls welling up. "Where should I cum?" I asked, desperation in my voice as I could hardly hold in my seed any longer.

"Inside me," Rene said between breaths, her body sliding up and down the table as I relentlessly fucked her, even as she held the table so tightly that her knuckles were white. Still holding fast to Rene's boobs, I drilled her pussy as fast as I could, starting to lose my breath until I finally let loose inside her pussy, moaning and shaking uncontrollably as I shot off streak after streak of semen into my boss's womb.