Gender: Male Age: Secret Location: N/A
|Introduction: Fucking my boss in the conference room was risky, and it finally backfired . . . except not really.|
It had been a full year since that one blissful evening when I bent my boss over her desk and fucked her for the first time. Not long after that first time, we began having sex in the office regularly and only very rarely off company property, which included occasions such as the organization’s annual convention, a couple times in her car and once in her house while the rest of her family was out of town. When at the office, we had always done pretty well with being discreet so as to not draw the attention of the evening security staff and, thus, jeopardize our jobs. The risk of being caught meant we almost always banged in her office, which was the most private. Every once in a while, though, we would venture into the conference room, which was a little more dicey because it was closer to the security office. However, after almost one year of delightful intercourse with my elder supervisor, we had been so successful in being inconspicuous that we took our good fortune for granted.
We followed a usual routine when it came to fucking. Actually, we rarely planned our trysts ahead of time – they were more or less spontaneous. Our line of work came with many taxing days, and it wasn’t a stretch to say that every couple weeks, particularly stressful days for each of us would coincide and we’d find ourselves both working late. Since we weren’t paid overtime, we found another way to compensate ourselves: vigorous sex.
Nothing inspired our banging quite like the tension of a long day at work. That point coupled with the fact that the rest of the white-collar workers were out by 6 pm resulted in some hot activity. In those instances, I would typically swing by her office in hopes of hooking up. Sometimes she would be on her way out to some other obligation or too inundated in work that I’d just have to hope for another chance soon. Usually, however, she was there waiting for me, and all that was left to do was pick a spot, often her desk. It was a wonder that desk hadn’t broken yet, given all the poundings I’d given my boss on it!
This fateful night went down according to the usual pattern, but on this occasion we decided on the location that presented more risk, which was the conference room. Once inside the room with the door closed, I lay down on the conference table, and we began to disrobe. I undid my pants while I watched my boss stand between my legs next to the table and take her top off, including her bra, to reveal her breasts. As I unbuttoned my shirt, my boss reached into my underwear, pushing it down my thighs while wrapping her small hand around my inflated cock. She grinned at me as she stroked me, slowly at first but increasing her pace as she bent forward, lowered her head and taking me into her mouth.
My boss didn’t suck me very often, so it was always a treat when she did. I probably moaned a little louder than I should have as she licked up and down my shaft and blew on the tip of my cock while rubbing my balls. I held onto the edge of the table when my boss’s head started to bob up and down, sucking my entire length.
I reached up and grabbed tufts of my boss’s hair as she pleased me with that blowjob. She sucked my cock for a good five minutes, allowing my dick to go as far as poking the back of her throat. I sighed happily as she eagerly blew me until she was ready to get on me. As good as her blowjobs were, I was always more than happy to get inside her pussy.
First, my boss slid her panties down to her ankles before kicking the piece of cloth aside. Then, wearing nothing but her short skirt and high heels, I watched as my surprisingly sexy, petite boss put her hands on my waist and climbed up on top of me, spreading her legs and planting her knees on either side of me as she hovered over my raging boner. I used one hand to position my dick under her cunt as she lowered herself down, lodging my tip inside her before slowly sliding down onto my balls.
We moaned in unison as my entire cock filled up my boss yet again. Despite all the times we had succeeded in having sex, I never grew tired of the thrill of plugging my stimulating supervisor or her startlingly tight pussy. This time she began by grinding on my hips, propping herself up with her hands on my chest while my hands ran up and down her hips and thighs, underneath her skirt.
After she grinded on me for a minute or so, my hands went still on her hips and held her firmly in place as I began to thrust in and out of her tight cunt. We groaned even louder now that we were actually fucking, and I quickly increased my pace, shoving myself harder and faster into her. Before long, my boss was moving as well, bringing her body down on top of mine as I thrust into her. Within minutes, we were sweating as we moaned and banged.
After a few minutes, I decided my boss was more than capable of taking the lead here, so I slowed my thrusting to a stop and simply allowed her to ride my cock. She bounced on my shaft energetically as her flesh slapped against mine each time she came down. Her boobs and hair rocked with her body as she straightened herself out and fucked my cock, sliding up and down it as her pussy gripped it like a vice. Incredibly turned on, I moaned and started to assist her, lifting my boss up and down, over and over again while she heartily screwed me.
“Oh yeah, oh yeah, oh yes, oh yes,” my boss muttered as my cock slammed deep inside her twat over and over again. I was content to just rail her pussy like that until I spurted my jizz inside her like I had many times before and intended on doing just that as I nailed my boss. The room had grown hot from our sex, and our sweaty flesh slapped together, her tight pussy squelching around my hard cock as we fucked. Amid the intense enjoyment, we became a little rowdy with our yells of great pleasure. It was then that, after one year of discreet office sex, we were made.
“I knew it!” we heard as the door swung open. My heart stopped, and I instantly ceased from thrusting into my boss. “I knew you two was fucking!” Standing in the doorway, as my career flashed before my eyes, was a tall, black security guard who was on duty that evening. We had been caught.
My boss and I were speechless as she rested on my hips, my hard cock still secured deep in her tight pussy. “Now don’t worry,” he said, beaming from ear to ear. “I won’t blow you in if I can get a piece of that ass.” It seemed the only hope we had of keeping our jobs was giving the young man (he was younger than I was) a chance to have sex with her. My boss was reluctant to agree, but we really didn’t have a choice.
“Well,” she finally managed, “I suppose you can have a turn tonight.”
“I’ll just leave you two alone, I guess,” I murmured as I started to lift my boss of my cock, which had yet to be satisfied.
“Oh hell no,” said the guard, and I stopped raising my boss. “I want some depraved shit. You stay right where you are, and lemme get in that ass.” I personally knew my boss could do anal but I didn’t think she could take double penetration. I had actually never ever entertained the thought of her in any type of group sex – our intercourse was based simply on the lust of screwing my supervisor. I wasn’t sure I wanted to be part of sandwiching her, but it didn’t look like I had a choice if I wanted to keep my job.
I looked up at my boss, who was visibly nervous but understood, as did I, the dire nature of our situation. “I mean, I can just let ya’ll boss know what you been up to. I ain’t the only one suspecting something with ya’ll, but I’d be more than happy to stop those rumors if I can get up in that bitch.”
Out of options, my boss sighed and invited the guard to join us. She and I were both nervous, but a part of me thought it was hot. I wasn’t much for group sex, but I had helped sandwich my ex-girlfriend on a couple occasions and, as awkward, debauched and shameful as it was, it was a ton of fun. The nature of this situation was uncomfortable, but if I were going to be blackmailed in order to keep my job, I might as well make the most of it.
As these thoughts ran through my head, the guard freed his long and already rock-hard cock, stroking it in his hand as he stepped up behind my boss and ordered her to spread her ass. My cock had softened a bit during the exchange but was getting fully erect again as I prepared to be part of a devil’s threesome with my sexy boss. My boss, taking the orders for once, obediently reached back with both hands and held her butt open as the black man poked the tip of his dick into her tight, dark hole. As soon as he wedged and inch or so of it inside her, he put his hands on her hips and began to slowly sink inside her.
My boss screamed, and I reached up and squeezed her boobs as I felt that long, hard dick fill her up on just the other side of the membrane that divided her ass from her pussy. Her already tight cunt grew more constricted around my engorged phallus, which felt wonderful. In my limited experience of DP, I had never gotten over being able to feel another cock’s thrusting while being barely separated from my own, but to maintain focus, I just squeezed my boss’s tits harder and looked up at her as she closed her eyes and gritted her teeth while she adjusted to the new pressure.
“You ever been fucked in the ass before?” the guard said.
“Yes,” my boss groaned.
“Ever been DP’d?”
“No!” she whined.
“Well, it’s about time you tried it,” he said. “I bet you like it.” With those words, he pulled back and thrust again into my boss’ ass, harder this time. Then he began to steadily fuck her butt, sliding back and forth, in and out of her shitter.
I didn’t need to be reminded of my part in this endeavor. Most of me just wanted to comply with the demand in order to remain employed, but part of me was wildly turned on to double-penetrate my boss on that table. While the guard started to fuck my boss’s ass harder and faster, I thrust up into that blissfully tight pussy before pulling back and slamming up into it again. As we two men began to saw in and out of her, my boss cried and screamed.
“Oh fuck!” she yelled. I was unable to tell if it was from pain or pleasure, but my bet was more of the former with a little of the latter, since it was her first time in a sandwich. Like I implied, I wasn’t an expert at double-stuffing a girl, so I was a little rusty, but it didn’t take me too long to get into stride with the guy in my boss’s ass. Soon we were plugging her effectively like a fully functional sex machine. As the guard pulled back from my boss’s ass, I bottomed out inside her pussy and then pulled back in time for the guard to slam himself to the hilt back in her shithole.
Back and forth, in and out, over and over again, our cocks fucked both her holes, stretching her taint and making her cry out in passion. The guard stood up straight as he drilled my boss’s ass, holding her waist as she straightened her back a bit, her knees still on the table and her hands still on my chest as she was double-stuffed. Meanwhile, my hands travelled all over her sweaty flesh, rubbing up and down her arms, her shoulders, her sides and her boobs. We were all moaning together as cocks fucked my boss like two pistons. I could tell from the altering tone of my boss’s cries that she was beginning to enjoy the double penetration.
We were both going completely inside her as we railed her ass and pussy. Our balls slapped against her taint each time we slammed into her, stuffing her to capacity. The room had grown nearly unbearably hot from all the sex, and we were all sweating profusely to the point where my back was slipping on the surface upon which we fucked. The squelching sounds of my boss’s ass and pussy got louder and louder, and the table rocked and creaked as we sawed in and out of my boss for another 15 minutes before my boss growled from orgasm through clenched teeth. Her hair fell into her eyes as her body shook, and my teammate and I carried on through my boss’s orgasm, fucking her holes firmly as the bitch squirmed between our thrusting bodies.
Our jabs became more deliberate and forceful after my boss came, and we were on the verge of orgasm ourselves. My boss collapsed on top of me while I held her sides and fucked her pussy harder and harder until I was ready to cum. The guard was really giving it to her ass as well until he decided we should cum on her. With that suggestion, he stopped banging my boss’s ass and pulled out instead while lifting her off my throbbing cock as well. My boss then dutifully, still wearing only a skirt and heels, kneeled on the floor, tilted her head back and reached her arms behind her to the ground as the security guard and I beat off over her. As weird a turn of events as this evening turned out to be, I grinned devilishly at the thought of watching two loads cover my boss.
I came first, spurting my man juice onto my boss’s chin, cheek, neck and tits. While I was still cumming, the guard blew as well, plastering her forehead and hair before aiming the remainder of his sizeable load at her boobs, which heaved as she caught her breath. By the time we had both finished ejaculating, cum trickled down my boss’s face, neck and breasts, even reaching her stomach.
“Don’t worry, ma’am,” said the guard. “I won’t be bothering you again. You two carry on. You wanna bang on my shift, go at it. I won’t say nothing.” He fixed his clothes as he said those words and then returned to his post without our saying anything. Once he was gone, I looked down at my cum-covered boss, who appeared shocked and mortified. We really couldn’t think of anything to say as we cleaned up and got dressed. It wasn’t until several days later that we even talked about it. My boss revealed she ended up enjoying being sandwiched but didn’t think it was something she’d do again.
Unfortunately, we got spooked from getting caught, and it was almost three months before we had sex again. Incidentally, what got us out of our dry spell was a night we were both working late and that same security guard was on duty. We were in my office this time, which was literally two doors down from the security office, and my boss was discussing a change in policy with me as she sat down on the other side of my desk. When the security guard went by during rounds, he said, “Seriously, if ya’ll wanna bang, don’t mind me. I’ll stay away for about an hour while you two get busy.”
There was a brief, awkward pause after he left. We hadn’t even spoken of our sexual relationship in weeks, but the frustration not coming together had been becoming evident to each of us. At that point in time, I was overwhelmed with the desire to plug my boss. “It’s been a long time,” I said, “and we’ve never done it in here before.”
To my surprise, there was little hesitation from my boss. “Yeah, what the hell?” Delighted, I stood up from my desk and closed my door as my boss stood as well. I placed her on the side of my desk and laid her on her back before reaching under her skirt and pulling her panties off her legs, careful, as always, to leave her high heels on. My boss was grinning as I undid my pants and exposed my cock, which had been sorely missing my boss’s cunt over these few months. With just our genitalia exposed for this round, we both grinned as I slipped in between my boss’s legs, which lifted up and rested on my shoulders as I guided the tip of my cock into her pussy before putting my hands on her waist under her skirt and sliding forward.
I pushed ahead until I was completely inside my boss, finally, after all these months. I sighed happily, relieved from all the built-up frustration within me. My boss held the sides of my desk and moaned, delighted to be having sex at work for the first time since being double-penetrated on the conference room table three months prior. My desk, at long last being used for plugging my boss, creaked beneath the bitch as I started to thrust in and out of her tight pussy, which I had missed incredibly much.
We sighed and moaned uncontrollably as I lunged forward again and again. I picked up my pace rather quickly until my balls were slapping against her ass as I slammed inside her deep and hard, over and over again. My boss’s ankles bounced on my shoulders while she took the steady pounding, and we were sweating in no time as our moaning, the desk’s creaking and the wet squishing of my boss’s pussy filled the room.
We fucked the entire time in that position. I held firmly to her hips as her heels thrashed over my shoulder while I nailed her pussy, thrusting in and out in rapid succession, hard and deep. I fucked her for close to half an hour until she came, legs kicking straight out and pussy tightening as she moaned. Then I fucked her some more until I came inside her cunt for the first time in what felt like ages. I gave her slow but hard thrusts until I was completely spent within her, filling her womb with my cum.
Once satisfied, I pulled out of her used twat and helped her off the desk. We then fixed our clothes before I opened the door to let some air in and went back to my discussion with my boss as we calmed down and caught our breath. As my boss got up to leave, we agreed to hook up again soon. I left that night more satisfied than I had been in half a year. As I left, the guard asked me, “Was she good?”
“Best boss I’ve ever had,” was all I said.
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