Gender: Male Age: Secret Location: N/A
|Introduction: Being part of a contingent sent to the company's annual convention in Arizona, my boss and I liven things up by banging multiple times throughout the event.|
“I can’t even imagine how hot Arizona is going to be,” I said.
“You and I won’t need the sun to make things hot,” replied my boss, who was seated beside me on the plane. The mischievous smirk on her face confirmed my assumption that we’d be banging on this business trip. My boss and I had now been having sex together regularly for about six months, and non-coincidentally, work had been a lot less stressful. This week, we, along with several others in upper management from our company, were being sent on a business trip: the organization’s annual convention in Arizona. While we were all expected to attend training seminars, my boss and I had every intention on sneaking away at least a couple times.
Since I had made it with my boss for the first time eight months ago, we had hooked up about a dozen times, all but one of which coming within the last six months. Most of those trysts occurred in her office (my office was much too risky), though twice I had fucked her on the conference room table and once in the women’s bathroom. This conference would be the first time we’d have sex off company property.
We wasted no time at all after checking in. We got separate rooms, of course, since no one knew we were banging, but as soon as I dropped off my bags in my hotel room, I headed straight to my boss’s room as we agreed upon when we landed. In fact, she had given me the copy of her card key in the lobby.
Arizona in June was, of course, hot as hell, but not as hot as what was about to go down in that hotel room. Nailing the boss was always risky, and this time was no different. We were supposed to be at some sort of orientation as soon as we arrived, but the schedule was so compact that my boss and I were going to have to blow off a few things if we were going to be satisfied. When I got to my boss’s hotel room, she was there as promised and ready to go. On the plane she had worn more casual clothes, but I was delighted to see that she had cleaned up for the occasion. Even though we were fucking on a regular basis now, the foundation of my lust for her lay in the fact that she was my supervisor, so it was important for her to play that role no matter what. So the button-up blouse, short skirt and high heels were really working for me when I set my sights on my boss, who lay seductively on the queen-sized bed. This experience was definitely going to be a different one.
As I shut the door behind me and made my way over to join my boss, she sat up and began to unbutton her blouse. I got up on the bed with her and pushed her onto her back while she reached around her back to unhook her bra. On my knees with my boss lying in front of me, I undid my pants to allow my already erect cock to breath while my boss exposed her firm tits. After completely undressing on the bed, I reached under my boss’s skirt and pulled her panties down her legs and off her body entirely. Without saying a word, I spread her legs and shuffled forward, pressing my engorged cockhead into the folds of her vagina, to which I had grown quite accustomed. With the tip of my dick wedged inside, I took hold of both of her ankles, holding one up by my head and pinning the other down on the mattress. As a sigh escaped from my boss’s mouth, I slowly thrust forward until my shaft was sheathed in my boss’s tight pussy.
I had never had this much ease of motion while screwing my boss before, since we had been confined to tight spaces and hard surfaces the other dozen or so times we had banged. It was a whole new shared experience for us as I began to stroke in and out of her pussy on that bed, moving slowly at first as I firmly grasped her ankles, my hands just above her sexy shoes. We moaned in unison while I plunged my cock deeper and deeper inside her, slowly but steadily increasing my pace as I fucked her. She held onto the bed sheets and encouraged me to continue while I drilled deeper and faster, going balls-deep inside her twat each time I pushed forward into her wet pussy, which was tightening around my member.
After several minutes of plugging my boss’s cunt, I let go of her ankles and, instead, leaned forward to squeeze her boobs while her one leg fell and rested on my shoulder and the other curled around my waist as I continued to fuck her. I really started to pick up the pace now, thrusting deep and hard into her tight pussy while we both moaned. Beads of sweat formed on my forehead as I exerted myself, bottoming out in her pussy only to withdraw and stick her again while I played with her tits. Her hands ran up and down my arms while she begged me to continue, wrapping her legs tightly around me, her one heel digging into my back while the other bounced on my shoulder.
My hands slid down to her waist and I really gave it to her, fucking her as hard and fast as I ever had. By now her hands remained motionless on my arms, her nails digging into my flesh while she cried out in pleasure. I pummeled her pussy for few more minutes, hearing the sound of my own balls slapping against her taint as I rocked her body. We continued to have sex on that hotel bed until we came at the same time. As her pussy twitched and tightened around my thrusting cock, I spewed out spurt after spurt of hot cum deep into her womb, both of us moaning as we climaxed. Once I was completely spent, I collapsed next to her, freeing myself from the cage of her limbs and pulling out of her wonderful pussy after once again successfully satisfying my boss.
It had been a few weeks since we had banged, so we took a few minutes to recover from the blissful sex we had just experienced. But then it was time to get up and moving because we couldn’t afford to miss the first seminar. Certainly our absence wouldn’t go unnoticed if we started skipping everything. We hurriedly got dressed while making plans to meet up again the following day. It was a four-day trip, but the last day would be a lot of packing and travelling, so my goal was to nail my boss at least twice more by the time we left Arizona
The following day was almost for naught, but we more than made up for it. Late that evening, I showed up at my boss’s room again, hopeful that she had stayed up for me. It had been a long, exhausting day, so she couldn’t promise me she’d be awake, but much to my delight, she was not only awake but wearing nothing but high heels and a skirt – not even underwear.
We hopped right to it. We had to be up early the next morning, but I would never pass up the opportunity to rail my boss. We started by the dresser, the top of which my boss held onto as I held her hip with one hand and stuck my dick inside her from behind with the other. Once I had forced my phallus up into her opening, I put both hands on her hips and thrust all the way inside her until I was all in. Scratching her heels against the carpet, my boss spread her legs farther apart, allowing me better access as I began to slide back and forth, in and out of her tight cunt. It blew my mind how tight her pussy was for a woman nearly twice my age, and I never got over how good it felt to fuck it.
My hands travelled up her stomach and to her bare breasts as my hips slapped against her ass with each thrust into her. I squeezed her boobs and fucked her harder, my balls swinging against her body each time I pushed up into her. Though we tried to be quiet so no one would hear us, we couldn’t help but moan in unison. Also, my shoves into her made her push the dresser against the wall each time I went to the hilt inside her, making a dull bang that most certainly could be heard in the other room. Fortunately, the room was either empty or the occupant was asleep or disinterested. Composed, I continued to rail my boss to my heart’s content.
After taking my drilling for several minutes, my boss began to push her body backward, meeting each of my pushes as my balls smacked against her. As we thrust into each other again and again, my cock slid all the way inside her pussy, as deep as physically possible. Our moaning got louder as we began to abandon our resolution to be quiet. We sweated and groaned as the pleasure grew more and more intense the faster and harder our bodies came together.
I began to plan on cumming in her pussy against that dresser, but then my boss ceased from her thrusting and told me there was something she wanted us to try in the bed. Not knowing what she had in store but excited nonetheless, I let go of her tits and pulled out of her pussy, allowing my cock to recover and stave off an orgasm for a little while longer while I followed my boss onto the bed. Once on, she got on her hands and knees and gave me a direct order: “Fuck my ass.”
I didn’t have much experience giving it to a girl in the ass and had never so much as thought of screwing my boss’s shithole. However, being the supervisor, she made the calls, so after just a brief moment of hesitation, I lubed up her asshole as she instructed me and then used one hand to push my dick into the entrance to her dark hole while using the other hand to spread said hole. Once I had managed to get about an inch of me inside her butt, I put both hands on her waist and thrust forward until I was balls-deep in her ass.
It was definitely a new experience for me, which thrilled both of us as we both gasped. I was completely inside my boss’s ass, and it was nice and tight around my cock. Without further hesitation, I started to fuck her, sliding in and out of her butt and increasing my pace as I grew more comfortable. Sharp cries escaped from my boss’s throat as I nailed her shitter, getting faster and faster with each passing moment.
“I bet you love fucking your boss’s ass!” my boss yelled as I gave it to her good. Her cries and comments were a little louder than I would have liked, but so far we continued on undisturbed.
“Oh hell yeah,” I moaned. I leaned forward, practically on top of her as I squeezed her boobs and fucked her ass hard and fast. Her shitter felt great, and I had every intention of drilling it again in the future. My boss panted, sweated and moaned, as did I, rocking her entire body as I fucked her.
I screwed her ass for a good 10 minutes before I felt her shudder in orgasm. She did manage to keep her reaction quiet, much to my relief as I was anxious that she wouldn’t be able to keep calm enough through an orgasm to prevent us from being caught. On the verge of my own satisfaction, I leaned back and released her tits, holding her ankles instead as I rammed hard and fast in and out of her shithole over and over again until I at last shot off deep into her bowels, filling her insides with my cum. I had never imagined that I’d cum in my boss’s ass!
It was about midnight when I climaxed in my boss’s asshole, so it was time to hurry off to bed. We had one more day left to bang and an early morning ahead of us. That day we decided to go for broke, skipping a seminar that was scheduled right before lunch and meeting in my room for a change. What I had noticed about my room was that, being on the first floor, the back porch was built into the ground and located in a rather secluded area of the resort. Over the first couple days, no one ever walked around back there, so I had run the idea by my boss, and she loved it. It was risky, but so was every other time that we had had sex.
My boss and I were dressed for the seminar but sneaked away to my hotel room. We headed straight out onto the porch to check out the area, and sure enough, the concrete, trees and lack of any sort of footpath all but ensured we would be undetected. Now, I had never fucked any girl in 110 F weather, but if I were going to do anything in this miserable heat, I was going to do my boss.
Since it was risky nonetheless, we kept as much clothing on as possible, despite the heat. Wearing a sleeveless top, short skirt and the usual high heels, my boss dropped her panties down to her ankles and kicked them aside while I freed my cock. My pants fell to my ankles, but I was otherwise dressed as normal as I watched my boss lift her leg over the railing of the porch, keeping the other heel planted on the ground. Looking over her shoulder at me, she beckoned me to get a piece of her in the intense heat.
As I had done multiple times already this week, I guided my cock into my boss’s wonderfully tight pussy, which she had spread out nice and wide for me. I immediately began to thrust in and out of her as she held herself up on that rail. My hands slipped under her shirt and clutched her boobs, which were supported by her bra. As I held her in place, I steadily stroked in and out of her cunt, over and over again, going faster and faster as I built up steam. The heat alone was enough to make us sweat, so once we really got into the sex, sweat was pouring from our bodies and soaking our clothes. I hated the heat but I loved that tight pussy, so I had no trouble with continuing to plow my boss from behind on the balcony of my hotel room.
After fucking my boss over the railing for 15 minutes or so, I was drained by the sun and needed my boss to take the wheel. Pulling her away from the rail while my cock remained stuffed inside her twat, I backed up and sat down on the lawn chair that was close by and asked my boss to ride me. She had no qualms with my suggestion and, as soon as we were in position, instantly slid up and down my hard shaft while I leaned back in the chair, moaning as I held her petite body in place.
Up and down, back and forth, over and over again, my boss rode my cock, her ass slapping against my thighs as we both sweated and moaned. She continued to fuck me for several more minutes before I came inside her for the third time that week. Perhaps it was the temperature outside, but something about that orgasm was really intense, and I moaned loudly as I filled my boss’s cunt with my jizz.
My boss rode my spent dick for just another minute or two until she achieved an orgasm as well, her pussy shuddering and tightening around my dick as she came. Soaked with sweat, we put our clothes back in place and hurried out to get lunch with the rest of our group, which was none the wiser that I had just deposited my load inside her.
The two of us figured three times in three days – especially since we had never fucked twice in the same week, except for the one time when we banged back-to-back – was a satisfying achievement and were happy to leave it that way. But as it often does, lust crept back in that evening, and we decided we had enough opportunity to give it another go. It was going to be an early morning again to make the flight, but that night when I was beginning to thrust into my boss doggystyle on her bed as she wore nothing but high heels, we both were content to catch up on sleep on the plane.
That last time for the week was pretty straightforward but still hot as hell and a ton of fun. Her tight pussy clung to my dick as I thrust hard and fast into her over and over again while holding her hips in place. The bed creaked beneath us as I plowed my boss from behind hard and fast while she slid back and forth into me, meeting my thrusts. I did her on her hands and knees for a good 20 minutes as we gleamed with sweat and moaned uncontrollably before she opted to roll onto her back and have me get on top of her.
Our sex was always shallow and dirty by design, so I had hardly ever lain on top of her before as I fucked her, but this time I did so upon her request as our business trip came to an end. My boss wrapped her arms and legs around me, digging her heels into my back as I powerfully thrust into her pussy over and over again, burying my head in the pillow beside hers and wrapping around the same pillow as I supported my boss’s head while fucking her pussy hard. The bed creaked loudly underneath us as I pushed in and out of her tight twat, fucking her deep.
Her tight pussy squished and my balls slapped against her taint as our sweat mingled together throughout the finish of our intense week of intercourse. I nailed my boss relentlessly, hard and fast for several more minutes, bringing her to a moaning orgasm. As her convulsing pussy tightened around my cock one more time, I began to lose control and pushed back away from her hard, breaking free from her legs which had been locked around me and pulling my cock out of her cumming pussy just in time to jerk off all over her tits. By the time I had finished cumming, my man juice had plastered her boobs and was trickling down to her stomach and neck while her chest heaved up and down. I exhaled deeply, collapsing next to her in the bed and, against my will falling asleep beside her.
I woke up in the middle of the night. My boss was fast asleep. I would have to be packed and ready in just a few hours, so I hurriedly got dressed and bolted for my room, hoping no one would notice. My boss was beaming when we reconvened on the plane, telling me how much she had enjoyed the week. Typically, we managed to have sex once every couple of weeks or so. This week we had managed four times in just three days. There was no way we would be able to keep up that pace with the pressures back home, but it was a fun and wild few days while they lasted!
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