As you might have surmised throughout the courses of my stories, my work requires lots of travel. I attend lots of trainings, conferences and exercises. I love my job but what makes it all the better are those times I’m met with unanticipated sexy surprises. It was an annual week-long work training event. There were well over 100 people in attendance from all over the organization. I had been there a few days. Now, you should probably understand something about my personality. I do not actively work at putting myself out there for attention. I am naturally a social individual. I make connections fast. And sometimes those connections develop into something I never saw coming.
His name was Sebastian. And he was one of the employees of another branch of the organization I work for.
What was unique about Sebastian is that he was technically a subordinate in our organization’s hierarchy. Nevertheless, we hit it off early during the informal gatherings the training hosted. Picture a well-built, rugged, funny guy. I didn’t mind the interest he showed but I also didn’t expect more than a bit of subtle flirting.
As the days went on, I started to look forward to our communications, first in person and later via text, once we eventually exchanged numbers. Obviously, it was there we could get a bit more playful. I tested the waters. One thing I pride myself on is my flirt game. For his part, Sebastian was no Romeo but he managed to hold his own. We hit it off quite well and I was intrigued by how things might progress.
Unfortunately, the training, itself, did not help things. It was a busy mess of meetings and last minute requirements that needed to be met. These often bled well into the evening hours. It also didn’t help that Sebastian was heavily invested in every little thing his supervisor wanted. Not much possibility to sneak away for play time. The training was coming to a close and I was just about ready to write Sebastian off as a fun distraction.
But then he surprised me with an invitation to come to his room during our final evening social in the hotel later that evening. He’d flaked before when we tried to make plans because his supervisor needed him, but Sebastian promised this time it was going to work out. He had some things to wrap up with his supervisor but he was definitely going to see me. I wasn’t holding my breath. Maybe he was intimidated and the closest Sebastian could muster to testing the boundaries was some flirty texts? That was fine, of course. I wasn’t about to hold it against him. One thing that drives me crazy is a failure to follow through when plans are made (more on this later).
I sent him a quick text at the agreed time.
“I’m on the way.”
My heart started to beat faster as I walked down the hallway I didn’t technically belong.
I knocked on the door.
He pulled me in quickly, to keep from any accidental eyes.
There was something new and thrilling in the clandestine way our evening happened. We sat and talked for a while, me on the edge of the bed, him on a chair nearby. I could tell he was nervous and wasn’t sure when or how to make a move. Sure I had experienced my fair share of exciting sex. This was different. He was the young, eager employee. I was the hot boss. The environment and the roles sparked the air between us with an electric kind of urgency. Mid-conversation he had worked up the courage to practically leap across the room and kiss me. It caught me off guard but was definitely welcome.
As we kissed, he slowly leaned me down, laying on the bed, his body pressed against mine. It was the final realization of days of teasing and tempting one another. I felt it in the press of his hips and gently opening of my legs with his own.
I was wearing jeans and a t-shirt. Him, shorts and a shirt. Everything came off quickly. I love when a man first takes in my body. There’s an almost appreciative hunger in the way Sebastian stared at me for a moment then slowly allowed his fingers to roam my skin. At first, I could feel his hesitation and I thought maybe he was a novice in the realm of sex, but I was quickly mistaken. For his part, Sebastian had a decent grasp on how best to please a woman. I shut my eyes and plunged my senses in the heady sensations of his touch, his kiss, the quickness of his breath.
I decided to return the favor. He was rock hard, throbbing for me. I had his shaft in the palm of my hand and stroked. Eventually, my own lips traveled down to take his head in my mouth. I have been told by multiple stallions I give some of the best blowjobs. Judging by Sebastian’s groans of pleasure, I had another positive opinion.
I slowly circled his tip with my tongue, desire and control obviously at war as he struggled to keep from exploding too soon in my mouth. I gave his cock a sweet, little kiss before releasing him from the agony of waiting. It was time to test Sebastian’s worth in bed.
I laid back and spread my legs. My pussy was already so wet and aching with want. He wasted no time slipping his primed cock inside of me. Our hips met in the rhythm of his thrusts. Deep, powerful, demanding. I had my knees up and back, feet crossed across his back, opening myself up best to fully take every driving inch. Sebastian groaned. I knew he wanted to cum but I wasn’t done yet.
Leveraging the strength in my hips, I easily sent him to the bed and swung up to straddle him. I eased myself down, feeling his shaft fill me. My head dropped back to revel in the pleasure. My hands at his chest. I rode Sebastian comfortably for a few testing lengths before picking up depth and speed. There was little strategy or intent to build any further tension. It was simply about enjoying the moment.
I did.
Through gasps and moans, I alternated between short pulses with him deep inside and the long ups and downs of the ride. Eventually he flipped me back over and took me doggy-style. His thighs a pounding slap against my own. We fucked longer than I’d originally expected. He definitely wasn’t a jack-rabbit or three-thrust wonder.
When he did finally cum, we collapsed back in a deep, shared ecstasy. It was late and the buses that would take us back to the airports in the morning were coming in a few short hours. I decided to stay the night and fell asleep wrapped in the arms of a fully satisfied man. I woke early to head back to my room for a shower and finish packing. I could tell Sebastian had enjoyed the experience. He wasn’t the only one.