I randomly received a text from a previous boss the other day, and invariably this is where my mind wandered to pretty quickly. A few years after I graduated college I ended up working at a medical education firm. It was a pretty typical job, required some late nights and a little bit of travel for conferences.
Elizabeth (not her real name) was not my first manager at this company. I was on another team initially and ended up getting switched over to hers after a few months. The first time we interacted in any detail was at the company Halloween party. Our conversation started off innocent but gradually became more flirtatious and interesting as the night progressed.
The more we drank, the more we danced and the more "handsy" we got with each other. I was dressed as a Spartan soldier from the movie 300 and Elizabeth was wearing a referee costume that was sexy but not over the top. We danced a lot that night and I certainly did not mind the way her hands explored along the edges of my costume and her fingernails grazed along my chest.
Elizabeth bore a resemblance to one of the actresses from the movie old school - Sarah Shahi. I was immediately attracted to her and was getting extremely turned on by her advances. Apparently, she had hooked up with a younger guy at a company party a few years prior and someone made a comment to her about it. Elizabeth seemed embarrassed and her whole entire demeanor changed and unfortunately, nothing happened that night.
A few months after Halloween I ended up getting my accounts switched and began working on Elizabeth's team. Neither of us brought up that Halloween party, and we developed a very good personal/professional working relationship. Occasionally we would go to happy hour after work, sometimes with colleagues from our office, other times with colleagues from different companies, and maybe a combination of both. The tipsier we both got the more noticeable our flirtations became, often saying things like we wished we could go back to that Halloween party.
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Several months progressed and it turned out that we worked really well together. I'm not sure how much of that can be contributed to the palpable sexual tension. That following May, we had a work function that brought us down to Hilton Head, South Carolina for the weekend. One of the partners was also supposed to join us but wasn't able to at the last minute.
Elizabeth and I got down to the location a few days early so we could set up for the conference. There was also a good amount of free time for us to relax and take advantage of the awesome amenities of the resort. We spent a good amount of time at the pool, on the beach, by the hot tub, and by the bar during the nights.
Spending all that time with my manager, in those capacities, just the two of us, really intensified the sexual tension between us and reached its peak on the Sunday before the conference was going to take place. That night we were at one of the more secluded hotel bars - just the two of us. The flirting, conversation, and exchanging touches really suggested that something was going to happen that night.
Elizabeth even pointed out one of the members of the hotel staff who she said was looking at and flirting with me earlier in the day by the pool. She kept teasing me saying things like that she would find out just how good I was since our hotel rooms were right next door to one another. I quickly replied saying something along the lines of "well we certainly don't need her to figure that out," I replied in jest, looking directly at her with a seductive grin on my face, to try and make things as clear as humanly possible.
Elizabeth and I finished our drinks and began making our way to the elevator, Constantly exchanging glances and flirtatious giggles. We got into the elevator and it almost was completely shut before another hotel guest obnoxiously threw his arm through the elevator doors so they would open back up. I was a few seconds away from throwing Elizabeth up against the elevator walls and passionately kissing her. And to make matters worse, the other guest was on the same floor as us so we didn't have any time alone in that elevator.
Once we got off and began walking toward our rooms, I could tell something was off. Elizabeth was much stiffer, wasn't smiling or laughing anymore, and was hardly even looking at me. It seemed like all the air had been taken out of the building. She barely even glanced at me as she fumbled with her room key and then muttered "good night" under her breath as she scurried into the room.
So after the events that just transpired, I felt devastated. It seemed that everything had been trending to that exact moment, all the things that transpired over the previous few days. What went wrong? Did I completely misjudge the scenario? Was there something I said that completely fucked everything up? As I agonized over these questions and headed into the bathroom to take a shower, I heard my phone start to ring. Elizabeth's name showed up on my caller ID which was extremely confusing to me. I was barely able to mutter "hello" before I heard her frantically asking me to come next door. Apparently, there was a huge spider in her shower which was completely freaking her out. She asked me if I could come over and kill it for her.
I said of course I would and then headed over to her room. When I went to knock on the door, it was already open so I went inside looking for Elizabeth. I faintly heard her shout, "it's in the bathroom in the shower! Please take care of it for me, it's really freaking me out!" I grabbed a few paper towels and walked back into the bathroom, Elizabeth being nowhere in sight. "Are you hiding from this tiny little spider?" I asked amidst a few chuckles.
After I killed the poor thing and flushed it down the toilet, I gave Elizabeth the all-clear sign and she cautiously emerged from standing on a chair in the back room. "OMG thank you so much!" Elizabeth said with a huge sigh of relief as she threw her arms around my shoulders and gave me a super tight hug. "I would have never been able to fall asleep knowing that thing was in there."
"It's really no big deal, don't worry about it!" I shouted back to her as she walked back into her bedroom. "Of course it is, I owe you big time," Elizabeth said as she came back out of the bedroom, wearing that long, fluffy, white bathrobe that comes in all the rooms. She walked right up to me, slowly peeling off the robe, asking me, "are you ready to take what you're owed?" while standing there wearing an insanely sexy black negligee. Without saying a word, I pulled the rest of her robe off her shoulders, pressed her up against the wall, and began enthusiastically kissing her.
After several minutes, any inhibitions that may have existed were completely melted away. It was very evident that there had been a build-up of sexual tension between us over the past few months. I grabbed Elizabeth's hips and lifted her up in the air as she wrapped her legs around my waist so I could start grinding into her. I quickly noticed she was not wearing any panties as her pussy was dripping all over the place.
After not much longer, I felt Elizabeth's hand slide down my torso and start to rub the outline of my cock through my pants. I was moaning in her ear as I was sliding my tongue all over her neck and looking for that erotic spot on her ear. She confirmed for me that I had reached it by letting out a huge gasp, throwing her head back, and starting to moan nice and loud.
Also contributing to her sensations was that she had slid down my pants freeing my cock, which she had in her hand and was firmly rubbing against her clit. Now usually I am a huge proponent of foreplay - and lots of it. I absolutely love to go down on a woman and eat her pussy relentlessly for pretty much as long as she will let me. I also love having my cock sucked for a while also, before we have penetration sex.
However, the tone of her voice, the expression on her face and the way her hand felt stroking my cock made this a not-so-normal situation. So when she looked directly at me and said, "Please, I NEED to feel you inside of me RIGHT NOW," as well as the fact that she was in a dead bedroom situation at home and hadn't been touched by her hubby in years. That just didn't seem right to me.
I stood there and teased her clit for a little while, slapping the head of my dick against it and rubbing my shaft along her labia. Then I moved to slide my head inside of her super tight pussy, thrusting it in and then pulling back out. After a little while of this, her pussy juices were starting to pool on the floor under us; she was getting so wet. I was starting to thrust into her painstakingly slow, getting a centimeter deeper each time, before pulling out completely and slapping/rubbing her clit with the head of my cock.
I kept up with the teasing and shallow strokes until her moans got more and more desperate, which was when I leaned forward and whispered into her ear, "tell me exactly what you want to feel baby."
I felt her nails dig into my back as she answered, "I need to feel you deep inside me, as deep as you can go." Each word seemed to come in between a set of moans. But I kept up with the same pace and the same depth - for the moment.
The frustration and the teasing were getting more and more obvious by her moans and the language she used. Finally, I heard Elizabeth shout out loud "OMG PLEASE, I need it so badly. PLEASE slam your cock deep inside me!" Right after that, I took several more shallow strokes and again started to slowly pull back out, until just the slightest bit of the tip was still inside her. I hesitated for a brief second, and then slammed my cock all the way inside her, in one hard, fast, strong thrust. I stayed there bottomed out inside her, keeping her pinned between me and the wall, as her entire body began trembling and are screamed out that she was cumming.
After she started to come back down from that, I adjusted my weight so that my pubic bone was pressed firmly up against her clit. Then I started to gyrate my hips around in different directions. All the while my cock stayed buried as deep inside her as she allowed it, and her clit felt the constant pressure of my weight up against it. A few moments later Elizabeth again cried out that she was going to cum, this time looking straight at me as she did.
Soon after that, I began thrusting and stroking deep inside of her. Gradually increasing the speed and force of my strokes until I could tell from her moans what felt the best for her. At this point, my own moans started to get deeper, louder, and more guttural.
"Your pussy feels so amazing engulfing my cock like this baby. You're gonna make me cum so hard!" I said to her in between thrusts. That's when I noticed her start to wrap her legs around my waist tighter and tighter, and I knew then exactly where she wanted me to cum. Soon after, I felt her hand reach down and begin caressing my balls. It didn't take too much longer until I felt my balls tighten up, my cock throb like crazy, moaning at the top of my lungs until I started exploding like crazy.
No exaggeration: this was one of the most intense orgasms I have ever experienced. My legs began to tremble and collapsed on top of her on the couch next to us. And as we laid there in a shared state of post-coital euphoria, I felt Elizabeth start to graze her fingernails along my back, my neck, and the back of my head - as softly and slowly imaginable. That honestly felt almost as good as the actual orgasm.
