6 comments/ 47465 views/ 31 favorites Fucking My Boss By: dpingjessie 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. 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. Fucking My Boss Ch. 01 I walked into my office as early as 6 AM. That was the time I was supposed to be at work anyway. I reported to my boss's Mr. Ashton's office to give him his morning coffee. I made sure to pop the first two buttons of my shirt for him to get a clear view of my 34DD breasts and and added an extra sway in my hips. As I walked in, I noticed Ashton's eyes raking all over my body and landed on my chest. I inwardly smiled a devilish smile and walked up to him. "Here's your coffee, sir." I said bending over the table with my breasts almost in his face. His eyes were glued to my chest and I looked down to see he had a boner. I smiled sedition, dropped his coffee on his table and ran to my office cubicle. I immediately opened a browser and searched for porn pictures. My hand immediately went to my breasts and was squeezing them. My panties were very wet and sticky but i did not take my fingers down there. I wanted Mr. Ashton's hands instead. I got back up and slipped into his office with my buttons still down. "I'm done with my paper work." I said as i smiled devilishly. "Miss Brielle, come closer." I instantly obeyed his command and went to stand closer to where he was sitting. I faced him but he just turned me around so he was staring directly at my ass in my black pencil skirt. His hands started roaming my legs and caressing them. I felt tingles shoot up my spine. The contact of his hands with my skin made my clit throb and my panties damper. He reached the waistband of my skirt and pulled it all the way down to my ankles. Now I was almost naked from my waist down. The only thing left was my thong down there. Thank heavens I chose to wear my black lacy thong. He kissed both of my ass cheeks and sniffed my crack. I let out a low moan. I wonder if he'll fuck my ass. I sure wanted that! He turned me forward so my front was facing him now. I looked into his eyes and all i saw was pure lust and hunger. He read he'd down to my shirt and undid all my buttons and tossed my shirt away. Now I was in my underwear. He immediately unclasped the hook of my bra and I watched it fall to the ground. Now my tits were on display for him. He wasted no time in tugging and pulling my nipples. First he licked and sucked my hardened nipples in his hot sinful mouth. He grabbed my right tit and sucked on my pink nipples while squeezing the left. He coated it with his saliva. Fuck. I was sure my juices were dripping down my legs now. He swapped his licking to my left tut now. He came up to kiss my lips hungrily. He inserted his tongue into my mouth and explored my mouth. He sloppily sucked on my tongue and I reached my hands down to the outline of his cock in his trousers and started rubbing him. He moaned into my mouth as i rubbed him faster. He came up for air and I undid his shirt buttons and his trouser zippers. He removed his shoes so he could step out of his trousers. Now we were both in underwear. Me in a thong and him in his tight boxers which accentuated his huge bulge. "Get on the table." He instructed and I did just that. I climbed on his brown wooden table and stared at his boner. Wow he looked really big. "Spread your legs." I sat down and spread my legs as wide as i could, exposing my extremely damp thong and wet thighs. He pressed a hand against my clit through my thong and started rubbing me. I moaned loudly and bit my lips. "You're so fucking wet Brielle." I moaned in response as he continued rubbing my clit. After about five minutes of that, he tugged down my thong and sniffed it. I looked at him doing this. He seemed to love the aroma because he then licked it. He sucked my cream right from my panties. He almost stuffed it in his mouth. He crumpled it and put it in his drawer. My legs were still wide open and my pink and swollen pussy was all open to him. He gave my clit a long lick. I moaned. Fuck why was he teasing me? He licked all the way down my slit and back up, this time avoiding my clitoris. He did this repeatedly while I played with my tits. I was getting fed up so I reached my hand down to try to rub my clit but he pushed my hand away before I could get there and gave a pussy a loud smack. I whimpered. For some reason that made me even wetter. My lips were red now from the smack but i didn't mind. He pushed his chair forward, sat on it and buried his head in my pussy. He aggressively attacked my clit with his tongue. He was bow sucking my remote control. He flicked my clit with his tongue and ate my pussy like it was his last meal. I was squirming and pushing his head deeper in between my legs. I wanted to die from pleasure. I didn't ever want him to take his mouth off my clit. He plunged two fingers into my cunt and fingered me while eating me out.