Fucking My Boss

Breathing heavily, we both straightened ourselves out as I retracted from Renee's wet, now cum-filled twat. Catching our breath, we fixed our clothes and hair without saying a word, only now realizing how hot and messy the room was. Renee broke the silence by saying she'd clean up her office when she got back from vacation.

I walked Renee back to her car, which I'd done before but not until today as someone who had had sex with her. I felt a sense of satisfaction and accomplishment unmatched by any other sexual experience I'd had. As Renee got into her car, she finally said, "Five out of five for your performance review," grinning as she did.

"The job may not pay much," I said, "but it sure comes with a hell of a perk."

We agreed to hook up again when we were both back from our respective vacations and to not cheat by meeting outside of work. What ensued was a long two weeks, but the anticipation made it only better.

My first day back, I could scarcely stay away from Renee's office, unable to focus on work. All I could think about was how I had had sex with my boss and how I wanted to do it again. Three whole days passed, actually, before Renee and I got together again. Our schedules just conflicted until Thursday, and even then we had to wait until almost 7 pm for the office to be vacated. As soon as the coast was clear, we disrobed in Renee's office. This time, I lost the shirt and tie immediately, and Renee stripped down to only her heels and skirt. She started by riding me as I lay on the desk, her heels planted on either side of my hips as she squatted over my pelvis and slid up and down me. Next we moved to her office chair, which stayed in placed despite the wheels on it once it was cornered by the other flank of her L-shaped desk and the back wall of the office. I sat in the boss's chair as the boss sat on my cock, facing away from me as she fucked me, sliding up and down my shaft until I came inside her again.

I began to have sex with my boss on a regular basis, one or two times a week. More and more, I would take her to my apartment after work and fuck her there, most of the time in my bed, before sending her home to her family. Renee was always working, so the kids and husband apparently didn't suspect a thing.

Our trysts in the office became fewer, and our fucking became more like lovemaking than just dirty sex. After a few weeks, I was even kissing Renee during sex. I believe it was six times that I'd fucked her before I ever kissed her.

Renee and I had regular sex for about three months before it caught up with us. By my count, I had nailed my boss 16 times by that point. Of those 16, nine were at my apartment and one was in the backseat of her car. The other six were in her office, and three of those were the first three times we fucked. It was just easier to bang her at my place, though the office sex was obviously hotter.

On December 19 we decided it was time to get a grip on ourselves. We both agreed that sex at the office was not only more fun but really the only reason there was any sexual element to our relationship. Yes, I respected Renee, but I wasn't looking for her to leave her husband for me or anything. As cheap as it sounds, we were missing the point. We weren't planning to have sex with each other forever, so we decided to fuck at the office one last time, though possibly leave the door open for the occasional session if we promised not to get carried away again.

To make this time special, we headed for the boardroom. In hindsight, I don't think either of us really considered the risk involved in relocating to another part of the building. Beside, it was 7:30 pm on a Friday; we'd waited extra long to ensure we wouldn't be walked in on.

It had long since gone dark outside when we walked into the boardroom. We decided to set up by the window where it was too dark in the room with the light off for anyone outside to see in clearly but enough light was coming in from the street lights so that Renee and I could enjoy the visual. Rene wore five-inch pink high heels, the same pencil skirt from our first time together and a bright pink, long-sleeve blouse. We shared no words and got right to it.

Renee unbuttoned her blouse, choosing to leave it on otherwise and just remove her bra instead, exposing her boobs. Next, as I likewise unbuttoned my shirt and left in on, Renee slid her panties out from under her skirt and stepped out of them, kicking them aside into a pile with her bra. By now, I had taken my pants, shoes and boxers clean off, so that I was wearing only the undone dress shirt and socks.

Renee motioned for me to get up on the table, and I obeyed my supervisor. I lay down on my back, inclining myself up by my elbows as I watched Renee climb up on the table with me. I had failed to notice until now that she had removed her skirt too. Despite her being 54 and someone I hadn't seen remotely as a sexual interest upon meeting her, I was taken back by how hot Renee looked in just those matching pink heels and blouse as the pale street light illuminated her small body.

Renee planted one shoe on either side of my hips as her anticipating pussy hovered over my erect, longing cock. All I had to do was continue to prop myself up and watch Renee guide my cock with her petite hand, holding my manhood in place as she lowered her body until my cock poked her vagina and then was entirely accepted into my boss's body for, by my count, the 17th time.

I scooted up the table to allow Renee a little more room as she stayed on her feet for now, squatting over me as her pussy tightened around the full length of my shaft. We were trying to be quiet, aware that we were more at risk - even if only slightly - in a more public area of the office. Renee began to slide up and down my cock, holding her own boobs now as I watched on in sheer delight to see my cock's being enveloped by the body of this woman who was exactly twice my age and also happened to sign my paycheck.

Renee's heels scratched against the surface of the polished table, certainly leaving marks as I simply lay still while my boss rode me. The juices left on my cock by Renee's pussy glistened in the light coming through the window each time Renee slid up. She began to pick up her pace until she leaned forward, slipping onto her knees and getting on all fours as she polished my knob deftly with her twat and started to pant. I finally lay back, moaning softly as I reached for her hips and began to thrust up into my boss, second-guessing if I really wanted to take regular sex out of this relationship.

Then the light went on. I didn't even hear the door open, but there was no denying what my eyes detected even if my ears had failed me. Horrified, Renee and I came to a dead halt and looked over at the door. My heart stopped for the first time since just before the first time I fucked Renee, but this time it was from dread. In the doorway stood a tall, black male dressed in a U.S Security uniform. I guess we should have stayed in the part of the building that the evening security didn't go.

"Ha, I knew it!" he exclaimed. "We all knew it!" Renee and I remained silent. Seriously, what do you say when you're caught screwing your boss in the boardroom? "You know, I could have you both fired if I told anyone," he said, threatening. We still said nothing, though Renee started to shift, as if she were about to dismount me.

At seeing the movement, the security guard urged us not to go anywhere. He uttered some things things I've since forgotten but finally offered not to tell anyone if he "got a piece of that ass," and he meant literally in her ass. I guessed I wasn't the only one who wanted to fuck Renee.

"Make it quick," Renee said, to my surprise. She began to get off me again as my mind raced, thinking I'd soon be watching my boss get nailed by a black security guard, which I supposed would be kind of hot.

Again, at Renee's movement, the guard barked at her to stay put. He then explained that he didn't want to nail Renee in the ass as much as he wanted to nail any older woman in the ass while another guy was in her pussy. In all honestly, my cock was fully erect inside Renee at these words.

I've always thought double penetration was hot, and I actually participated once in sandwiching a girl named Jessie, one of my very best and hottest friends, with her husband. It was almost a year ago from this day, in fact. That threesome was the most fun I'd had in my life, and I'd been obsessed with double penetration since then. I hadn't done it since, but while I was still waiting for another session with my friend, there was no reason, especially considering these circumstances, that I wouldn't happily share my boss with this other man now, even if he was a total stranger to both of us.

"You can't be serious," my boss protested. He was dead serious. Lacking the purest motives, I convinced Renee to go through with it, acting less excited than I actually was so as to not lose her respect. Ultimately, Renee decided that a cock in each her pussy and ass simultaneously wasn't as bad as losing her job.

My heart beat fast, and I breathed heavily with anticipation as the black guard undid his pants, revealing a very sizable cock, and stepped up behind Renee. My cock was firmly stuffed in my boss's cunt, fully inflated as the guard pushed my supervisor forward on top of me before spreading her ass cheeks.

"You ever been fucked in the ass before?" he said as his cock poked her asshole.

"Yes, actually," Renee answered as she held her breath and shut her eyes, bracing herself. Wow, she was hot.

"Ever been DP'd?" he followed up as he mercilessly sank about half his cock into her butt in one push. I would have loved for the answer to have been yes.

"No!" Renee shrieked as she took the black cock uncomfortably into her shitter. I remained still, balls-deep in my boss's pussy as I held onto her shoulders, kind of subconsciously holding her in place as our third wheel pushed more and more of his thick meat into my poor, petite boss until both he and I were inside her to the hilt.

Renee cried out in undeniable discomfort. Despite my boss's pain, I couldn't help but be immensely pleased at the turn of events. I felt guilty for having these feelings, as if I'd betrayed my boss and sided with the enemy, but hey, we were both in certain trouble if we didn't comply. At least one of us might as well enjoy it.

The guard ground up against Renee's ass, holding her hips firmly as he leaned forward to ensure he was completely inside her. I'll never forget how he looked at me, making me feel very awkward and even a little scared as he said, "You better not just lie there. You're in this too." He had no idea how little motivation I needed to carry out his demands.

My only response to the man at all was pulling my cock back as far as I could manage in these close confines and then thrusting it back in. I shuddered a bit, somewhat uneasy as I felt that cock on the other side of the thin membrane that separates a woman's asshole from her vagina. It wasn't a brand new experience for me, as I alluded to before, but my only familiarity with the sensation was one time a year ago and neither with this massive an instrument on the other side nor with a woman quite this petite. However, as with my other threesome experience, the stimulating nature of the activity outweighed any awkwardness so that I was never less than completely turned on.

For a second time, I pulled back as much as I could and pushed up into my boss, my cock eliciting a squishing noise from Renee's pussy as I fucked her. After that thrust, the guard began to go to work. With more room to breathe than I had, he began to slowly but steadily fuck my boss in the ass as he held her hips, making her whine as she clutched my shoulders, similar to how I was holding onto her in that moment. The guard leaned forward, pushing Renee closer to me until her boobs were almost touching my chest. All the while he was sinking in and out of her ass while Renee's being pushed forward somehow gave me better access to her other hole and allowed me to thrust in and out of her more effectively.

It wasn't long before I was dripping with sweat, to the point that my dress shirt was soaked. With Renee in such close proximity to me and the other man's sharing her, the air around me grew very thick. I was taking deep breaths as I continued to hold onto Renee and slide myself into her as steadily as my restrictions would allow, all the while feeling that larger cock going in and out of my boss's ass on the other side.

Renee let go of my shoulders and instead held herself up in between us two men with her hands flat on the boardroom table. I don't know if Renee was starting to enjoy the double-fucking, trying to get more comfortable or just complying, but the guard and I were able to really get going with double-penetrating my boss now. He and I thrust harder and faster into Renee, never really establishing a rhythm like I remembered doing with Jessie's husband a year ago. This time, I knew it wasn't about the girl, so there was no working with the guard to keep Renee's comfort in mind. I did my best out of respect for her, but the guard was eventually plundering her ass pretty hard, so I gave up and just pumped into her to my heart's content as well.

Beside some moans and cries, Renee was relatively silent as we two men sawed in and out of her on that table. The loudest sound was the guard's grunting and panting. Also audible were the creaking of the table and the sound of my boss's holes as they were both filled to capacity.

By now, Renee was pressed against me so that I wasn't able to see much beside the other dude, especially given how short Renee was, which sucked. I just turned my head to my left and was able to catch a decent view of my boss's body, clad with her bright pink blouse and high heels. I could see that black cock going undoubtedly into her ass as well, not that I couldn't feel that prick inside Renee anyway on the other side of the membrane.

I put my hands to my sides and grabbed Renee's thighs as I held onto her. I thrust up into her as hard as I could, slamming into her over and over again while the guard plugged her ass, really getting into it too as he smacked her rear end, pulled her hair and talked dirty to her, degrading her.

Renee and I, and probably the guard, were slick with sweat as Renee continued to be helplessly double-penetrated. She was taking it well, even if she wasn't enjoying it. Her glasses slid down her nose but remained on. Her blue eyes were shut throughout most of the session, occasionally opening, usually when she was inhaling deeply. Despite my boss's obvious discomfort, I selfishly reveled in the fact that not only was I finally joining in on a double penetration again and not only was it with a different woman, which I'd never expected, but I was double-penetrating my boss. My wildest fantasy involving Renee never dared entertain such a dirty twist.

As I grew closer to cumming, the guard now leaned forward, practically lying on top of Renee. His feet were still planted on the floor, I presumed, but his head was now uncomfortably close to mine as his big hands enveloped Renee's shoulders. His legs, also, were touching mine, something I'd successfully avoided during devil's threesomes, to the best of my recollection, until now. I kept my head turned away, trying to ignore the guard's loud panting near my ear, focusing instead on Renee's grunts and on the fact that she was really getting sandwiched now. I successfully managed to stay focused and fucked her even harder as her sweaty body was pressed against mine while her hole was pitilessly pounded on the other side. Before long, I was over all the awkwardness of the other man's close proximity. Renee continued to be stuffed in both holes and we simultaneously slid in and out of her for just a few more minutes. Just as I entertained the thought of exploding inside my boss, the guard announced that it was time to cum on her.

Rene let out a loud sigh of relief as the guard finally pulled out of her now ravished asshole. The guard then rolled my boss off me, onto her back, as she heaved on the table. I quickly stood up as the guard stood between Renee's legs, which dangled toward the floor, and he stroked his cock until he was shooting long, thick streams of cum all over my boss. It was quite a delightful sight for me, actually.

Once the guard was done, he ordered me to follow suit. Again, he didn't realize how on board I was. I too stood between Renee's helpless legs as the guard stepped back. Still wearing her glasses, blouse and heels, my boss now had cum splattered all over her, especially on her stomach and boobs, but a couple shots hit near her mouth and on her neck.

It took me a minute, but at last I was standing in my company's boardroom, cumming on my boss as she lay sprawled on the table while a near perfect stranger watched. Jets of semen shot out and plastered my boss from her chin to her belly button and everywhere in between. Once I was finished, loads of cum were streaming down Renee's tits mostly, but sizable amounts pooled on her stomach as well as dripped from her face.

It took us a few awkwardly silent moments to clean up. The guard left as soon as he'd straightened out his clothes, only telling us to go home, leaving our future at the company in the balance. There was no guarantee that he'd keep his word, but we had no choice but to trust him.

Once we'd cleaned up the room and got dressed, Renee and I headed back to her office to grab our coats and head out. We didn't want to discuss what had just happened, but I think our feelings differed for sure. Renee understandably seemed a bit traumatized, not that I wasn't a little too, but surely I thought the experience was a lot hotter than she did.

As I drove home, I thought about how throughout the double penetration, I flashed back to my first devil's threesome experience with Jessie. She joined Renee on my mind that night, and I realized it had been a while since I'd talked to Jessie, so I figured I'd send her a text. But that story is for another time.

Renee and I didn't talk again until after the weekend, but such was normal for us, even though we'd been fucking regularly these past few months. On Monday, we interacted professionally but still didn't talk about what happened. In fact, it wasn't until right before we left work on Christmas Eve, right before a long weekend, that we discussed it briefly and agreed to do as we said and stop being involved sexually.

Over the next couple months, we'd see that guard occasionally, but he, for the most part, acted as if nothing had ever happened. A couple times he'd grin, and one time he made a comment about our "party," but it seemed, at least, that he'd kept his promise and that he wasn't asking for anything more - not that I would have necessarily minded.

Meanwhile, Renee and I abstained from relations for as long as we worked together, which shockingly ended up being only a couple months, actually. She was terminated abruptly and never given a reason. Perhaps the guard let the cat out of the bag, but, four months later, my job was still intact, as far as I could tell.

Just last week, I answered the door of my apartment to invite Renee, no longer my boss but now just my significantly older friend, inside. Well, "just my friend" may not be the most accurate description of our relationship.

"How's the new job?" I said, leading Renee toward a familiar spot.

"I really like it," she said, "but don't worry; there's no handsome young buck lined up to take your place." With those words, she pulled off her top and walked in front of me into my bedroom. I followed her in, shut the door and proceeded for the first time in six months to fuck the woman who was formerly my boss.