I [F] went on a business trip with my boss’ boss [M] and flipped the power dynamic for a night.

Note: Names have been changed, obviously

When I was 22 I was about six months into my first corporate job when I was sent on my first business trip. I wasn’t loving the gig for a number of reasons, but my biggest gripe was that I was the most junior employee and the only young woman on my team and I was treated like dirt. I’m a natural people pleaser so I always bent over backwards to accommodate everyone, but my resentment towards the team was growing and I saw the business trip as an opportunity to prove my value. 

Five of us were sent on the trip, including my boss’ boss, Bill. Bill was in his 40s or so, very tall, broad-shouldered, deep-voiced, well-dressed, and much more put together than the rest of the team. He carried himself with a quiet confidence that garnered instant respect from everyone around him. But despite his composedness I could sense that he was nervous around me. He avoided interacting with me one-on-one, and I could feel him staring at me whenever we were near each other. Even when we were in client meetings together I caught him taking constant passing glances, which turned into full-on stares whenever my ass was within his view. 

The trip sucked work-wise, and as per usual I was given the grunt work nobody else wanted to do and any contributions I had were ignored or dismissed. On the last night of the trip the five of us congregated at the hotel bar and had a few company-sponsored drinks. I was wearing a curve-hugging blue-grey pencil skirt that tended to elicit a lot of stares whenever I wore it, and I noticed that Bill was not-so-subtly trying to find any opportunity to ogle my ass – the more he drank the more obvious he became. We were in a city with a good amount of nightlife, so my liquored-up boss and teammates decided they wanted to go bar-hopping. Bill turned down the offer, and I couldn’t think of anything less appealing than spending even more time with my boss so I decided to stay back despite their urging. The rest of the team left for their night out, leaving Bill and I alone at the hotel bar together. 

Bill asked if I wanted to have one more drink with him before we headed to bed and I agreed and moved to the chair directly across from him. He made awkward small talk about our workweek, and I could see that he was nervous. I’d had a few drinks and was fueled by liquid courage, and that week had confirmed that I was going to quit my job soon anyway, so I decided to throw caution aside. I stopped Bill in the middle of some long-winded rant about a deliverable and asked him, point-blank: “do I intimidate you?” 

He was flustered. “What makes you think that?” 

“You’re usually so confident, but you always seem nervous around me. Is it because you find me attractive?”  

He paused. “I can’t deny that you’re a beautiful woman.”

“So you’re attracted to me.”

“I’m *incredibly* attracted to you. But I want to keep things professional.”

I was emboldened by one too many vodka sodas. “You didn’t seem too concerned about professionalism when you were staring at my ass all night.” I couldn’t help but notice a bulge growing in his pants, even in the dim light of the hotel bar. 

“Do *you* find *me* attractive?” he asked, his voice tinged with insecurity and his eyes filled with desperation and desire. At that moment I realized I had him wrapped around my finger.  

I dodged his question and smiled. “Let’s keep things professional.” I leaned onto the table and moved my face a bit closer to his, and he looked at me for a moment before awkwardly leaning over the table, grabbing me, and kissing me with way too much tongue. He moved to the seat next to mine and we continued to make out. I could sense his desperation, because every time I pulled away at all he’d frantically pull me back to him. After months of being disrespected and walked on at work the sudden power I had over my boss’ boss was intoxicating. 

A few minutes later he suggested that we go upstairs. I was staying at a cheaper hotel across the street so I was a little worried about getting caught and not having an excuse, but I hated my job anyway so I agreed. He beamed with excitement, immediately closed his tab, and left most of his glass of wine behind before guiding me to the elevators with his hand on the small of my back. 

We made some awkward small talk at the elevator bank, but the moment we stepped into the elevator he frantically pressed the ‘door close’ button before smashing his face into mine again. His poised, professional demeanor had been replaced with uncontrollable desire. His hands moved all over my body as though he had no idea where to start with me before settling on squeezing my ass so hard that he almost lifted me off the floor. When the elevator door opened he practically jogged to his room. Once he opened the door to his beautiful suite (a stark contrast from the small, airshafted room I was posted up in at the cheaper hotel across the street) he tried to immediately slam me against a wall, but I pulled away from him. “You need to relax,” I said. I took his hand, walked him to the bed, and sat down at the end, looking up at him.

He immediately tried to launch on top of me. “Slow down for a second. We don’t need to rush,” I purred. “Take off your clothes and lie down on the bed for me.” He proceeded to urgently and clumsily rip off his clothes. I licked my lips when his cock popped out of his pants. I couldn’t deny that it was gorgeous – 7 or so inches and girthy, with a full but proportional tip, round and taut balls, and well-landscaped salt and pepper pubic hair. I felt myself getting wetter, and my pussy suddenly felt heavy. He laid down on his back, his rock hard cock standing at attention. There are few things more wonderful in this world than the sight of a beautiful, hard cock waiting for you.

“Since I’ve met you I’ve gotten hard every time I’ve looked at you,” he said.

I crawled on top of him, hiked up my pencil skirt so just a thin pair of panties was separating my pussy from his cock, and lingered just above him. He could feel my soft (facial) lips just barely grazing his. The moment he felt the graze of my lips he grabbed my face, shoved his tongue down my throat, and started thrusting his hips up at me. I jerked away from him. “Slow down. Easy,” I said. He eased the movement of his hips and I brought my face closer to him again. He was breathing heavily and I started to slowly grind my clit against his cock. He struggled to stop himself from thrusting more.

Still on top of him, I peeled off my turtleneck. My tits were spilling over my bra and one nipple was popping out, which I could tell was driving Bill absolutely mad. The feeling of my sensitive nipple grazing against the fabric of my bra made my pussy pulse. Bill must have noticed how hard my nipples were and the look of pleasure on my face, because he took the opportunity to fondle my tits and gently suck on my nipple. His gentle sucking and nibbling felt incredible, and my pussy was throbbing, with just a thin piece of fabric separating me from his gorgeous hard cock. I continued to grind my clit against his hard-on and savored one last moment of his teasing before I pulled away.  

I slid off of him, pulled my skirt back down so I was wearing it normally, and stood next to the bed. My shirt was already crumpled on the floor. First I removed my bra, and he couldn’t stop himself from starting to slowly stroke his cock as my tits spilled out and settled on my chest. Then I turned away from him and bent over. His breathing became heavier and his stroking sped up as I arched my back and showed off my ass in my pencil skirt while knowingly looking back at him. I slowly started pulling my skirt down, shimmied the waistline past my ass (always a daunting task), and let it fall to the ground, revealing my bare ass cheeks in my panties. I was turned away and distracted by the clothing removal process so I didn’t notice his movement, but I suddenly felt two cold hands on my tits and a hard cock rubbing against my ass. “Didn’t I tell you to relax?” I asked as he leaned down (awkwardly due to the height difference) to kiss my neck and very lightly twisted my nipples between his fingers.

“I couldn’t help myself.”

I turned around and gently pushed him onto the bed. I noticed that precum was dripping from his cock, so I climbed on top of him and gently licked it off. Then I took each of his balls in my mouth, very lightly sucked on them, and swirled my tongue around them. He moaned and quivered. 

“I don’t know how long I’m gonna last,” he confessed. 

“Let’s see how long you can control yourself,” I replied. I slipped off my panties and climbed farther up on the bed so my ass and pussy were hovering directly over his face. He begged me to sit on his face as I teased him for a moment before putting my full weight on his face, my hands teasing my nipples as I grinded my hips. He lapped at my clit with firm, long, rhythmic strokes. I was already close. 

I told him to play with my nipples, and he obliged as he continued to lick me. The grinding of my hips was perfectly timed with each stroke of his tongue so I could put more weight on him as the fattest part of his tongue pressed against my clit, adding just the right amount of pressure. My head was spinning and I let go for my first orgasm. It was so unbearably intense that I instinctually started to lift my pussy away from him, but he grabbed my ass and pressed me down on him so I couldn’t escape the full pressure of his tongue. I couldn’t hold myself back from screaming over and over as my soaked pussy gushed and pulsated with waves of overwhelming pleasure. It was so intense that it almost hurt, and I tried to pull away, but he kept pressing my ass to his face and licked me until he’d drained everything he could from me. 

For a moment I blacked out and leaned my head against the headboard. When I came to I raised my hips away from him and moved down to lick my juices off of his lips. 

I slowly moved down his body before hovering over his cock, which was twitching and soaked in precum. He marveled at my naked body and begged me to sit on it. In the heat of the moment we hadn’t realized that we didn’t have any condoms, but I told him that I was just going to tease him and then I’d give him a blowjob when I was done with him. I rubbed the entrance of my soaked pussy against the tip of his cock, finding it harder and harder to resist taking all of him in.  He thrusted his hips up and begged to fuck me.

In a lapse of judgement I lowered myself onto his cock. I’d never had bareback sex with someone who I wasn’t in a relationship with, but at that moment I was completely overwhelmed with desire and his raw cock felt like heaven. I felt my entrance gripping him as he let out a moan and grabbed my ass. After pushing his cock through my tight entrance I slowly lowered more and more until every inch of him was inside of me. I bounced up and down for just a few seconds before feeling his cock twitch and stiffen and his breathing speed up. Then I stopped and raised myself completely off of his cock, letting his tip rest against my entrance. “We should stop. We don’t have any condoms.”

“Please, wait, don’t stop,” he pleaded. “I’m clean.”

I tried to resist but couldn’t stop myself from lowering onto him again. I took his hands and moved them to my tits so he could keep teasing my nipples. Then I reached beneath my ass and fondled his balls while I bounced up and down on him for just a few seconds.

“I’m gonna cum,” he moaned, and as I tried to raise myself off of him he grabbed my small waist and pushed me back down, then back up again, until he was bouncing me up and down on his cock. I grabbed his hands off of my hips and put them back on my tits before slowly raising myself off of him. I then went back to teasing his balls as I rubbed his tip against my clit and he teased my nipples.

“Please let me cum,” he begged. “You feel so good…”

“I will. I want you to cum down my throat. But not yet.” I slowly lowered myself back down onto him again. Instead of bouncing up and down I took him in as deep as I possibly could and grinded my hips back and forth so my clit rubbed against his pelvis and my pussy gripped every inch of his cock. The feeling of his entire cock twitching deep inside of me and his hands teasing my nipples brought me closer and closer to the edge. It was a race to the finish at that point because we were both on the verge of exploding.

“If you can wait for me to cum I’ll let you bend me over,” I said. His eyes lit up and he continued to tease my nipples and kiss my neck while I grinded my hips on him. “I’m so close,” I moaned, my head spinning. I could see stars behind my eyes. I started moaning more and more as my pussy got wetter and wetter and tightened around his cock. 

“I’m gonna cum,” he groaned.

“Don’t cum yet…” As the words came out of my mouth my pussy burst into wave after wave of pleasure as I grinded as hard as I could on his cock. I screamed and screamed as he teased my nipples with his fingers and stared up at me in ecstasy. My pussy gushed and I continued to ride him, feeling myself pulse and tighten around him until every last wave of pleasure had finally subsided.

I nearly collapsed, but instead of letting me rest he immediately lifted me off of him and bent me over. He was a lot bigger and stronger than me and he could throw me around like a ragdoll. He pushed down on my back so it was arched as much as possible and grabbed my hips. I was still too blissed out from my orgasm to resist, and the feeling of his cock re-entering me from behind was heavenly. My eyes rolled to the back of my head and I moaned as he slowly pushed his cock back inside of me. He pushed through the vice grip of my entrance and went deeper and deeper until his whole cock was inside of me. He grunted with pleasure as he started slowly thrusting. 

“You feel so fucking good,” he groaned. He tried thrusting faster, then suddenly stopped and pulled out so he wouldn’t finish too quickly. He took a moment to compose himself as he stared down at my ass. He slowly started again, entering me one inch at a time so he could adapt to the tightness of my pussy without busting. Then he strengthened his hold on my ass and started going faster and faster. I gripped my pussy around him, bringing my legs together, engaging my kegel muscles, and arching my back even more as he sped up. My ass bounced with each thrust and I could feel that my face was completely flushed. I felt deliciously stuffed by him and wanted nothing more than to feel his seed inside of me.

“You’re so tight. I’m gonna cum…” he groaned. “Can I cum inside of you?”

“I’m on birth control. Cum inside of me,” I moaned, feeling as though I was floating with pleasure. I wasn’t exactly thinking straight given that I’d just had two earth-shattering orgasms and was being gloriously pounded from behind, with the walls of my tight pussy being stretched out and each thrust sending shockwaves to my clit. He groaned loud enough to wake the neighbors and gripped my ass even tighter as I felt him pump his hot cum inside of me. His cock twitched as he completely filled me up. He stopped thrusting towards the end, but I moved my hips back and forth so his cock kept pumping in and out of me until his balls were completely drained. 

Thankfully despite our stupidity I didn’t wind up with any STDs and my birth control came through. I only stayed in that job for a couple more months, and because Bill and I worked on different floors we only saw each other a couple times a week. I didn’t want to make things more complicated than they already were and I started to get some indicators that he may have been in a relationship (although he didn’t wear a ring on his finger at work), so I rejected his countless future advances, although whenever we were in a room together you could cut the sexual tension with a knife. He still emails me on occasion, but I think I’m satisfied with our one memory. Although writing out this story is making me wonder if I should reach out…

Source: reddit.com/r/gonewildstories/comments/kf2cv3/i_f_went_on_a_business_trip_with_my_boss_boss_m