I had first met Mr. Bass my senior year of highschool during a career fair and he almost immediately offered me the summer job. He was a kind person and not bad looking for a middle aged man so I took his offer and came to work for him the summer before I started college.
The Job mostly entailed answering the phone outside his office and amusing him when he would come out and make small talk with me. I had just turned 19 and there was no question my figure had responded well in its development. I wasn’t unaware the way Mr. Bass would stare at me, sneaking a peak of my tits or ass whenever he got the chance. I never felt uncomfortable by his attention though, It was flattering and I assumed it couldn't hurt having my boss fancy me.
The work days all remained pretty straight forward the first several weeks, in till the companies 4th of July picnic in the park... Mr. Bass and his two other business partners had brought pretty alcohol to the party and they were sharing it with me even though I was underage, which I thought was really cool! We were all hanging out watching fireworks and barbecuing when my boyfriend Glen who I had brought with me ended up having a few too many drinks. He began getting a little loud and rowdy shouting at people who weren’t in our group, and even trying replace Mr. Willison as the grill master. When Mr. Bass came over and asked him to settle down, to my horror, Glen began mouthing off to my boss.
Mr. Bass kept his cool but told him he would have to leave if he didn’t get a hold of himself. I tried getting Glen to sit down but he had become angry at being told what to do and told Mr. Bass “He’d do whatever he wanted.”
With him being my ride and unable to safely drive himself home Mr. Bass decided he would drive him back to our apartment. After a joint effort of me and my boss settling him down he headed for the parking lot.
Mr. Bass was walking smoothly beside me while Glen, probably eager to get away from the embarrassing situation he had created for himself walked ahead of us.
"I hope this doesn't mean your done for the night" Mr. Bass said walking beside me. "We are only getting started here and I have some important business partners coming later I'd like you to be familiar with Jessica."
My boyfriend threw me an irritated look from up ahead. "I don't know, maybe it is time to call it a night." I replied
Mr. Bass unlocked the car and Glen jumped in the passenger seat. I got in the back and we pulled out of the parking lot. I could feel Mr. Bass staring at me in the rear view mirror but I kept my head down in my embarrassment of the situation.
Finally my boss spoke up glancing at Glen. "Son I hope you know this is nothing against you, it was a company event and we needed to maintain our professionalism." Glen continued to stare out the window as Mr. Bass continued. "But Jessica does work for the the company now and I need her to be at the companies events, You can understand that right?"
"It's already 9:30" He stated to no one in particular.
"Well we don't have work tomorrow, and I'll drive her home when it's over." Mr. Bass countered.
I sat in silence in the back seat while they discussed what I'd be doing for the night. They went back and forth till we were outside Glen and I's apartment. My heart actually sank a little when Glen reached for the door handle and told me to come on.
I looked up and saw my boss looking at me expectantly in the mirror. I found myself saying "I'm sorry babe it's a company event and I work there, I'll be home tonight though."
"Really Jessica?" Glen asked through clenched teeth.
I was really starting to get annoyed at how he was acting... Why was he embarrassing me in front of my boss like this?
"Yes Glen... It's not my fault you drank too much and got asked to leave, I'll see you when I get home."
Glen gave us both a glare before getting out and slamming the door.
"Oh my god... I am so sorry Mr. Bass he isn't usually like-"
Mr. Bass just started chuckling and shook his head. "No dear it's quite alright, boys will be boys. Here you want to hop up here?" He asked patting the passenger seat.
I popped out and got in the front seat.
"I'm glad you decided to stay it's going to be a fun night." He told me and gave my leg a squeeze. I didn't know if it was just the wine but it felt like his hand lingered on my thigh before putting the car into gear and pulling away.
We showed up back at the park and enjoyed another half an hour of fireworks before it began to die down. Mr. Bass told everyone not to worry and announced we were meeting back at his house for the after party. I glanced at my phone and noticed the time was 10:15 and I had three texts from Glen.
"Do you need to go home Jess?" I heard my boss ask as he walked up to me.
I thought about going home to an angry boyfriend, or drinking wine with my co-workers. "No I don't need to go home yet, in less you need to drop me off." I told him.
"I'll make sure to call you a cab whenever you need it." He said with a buzzed wink.
Mr. Bass's house was insane... It had its own gate and I got super excited when I saw his pool and hottub! I almost immediately talked Arianna, the office account manager, into joining me for a swim in our underwear. My boss's house was so big everyone was scattered throughout it and soon Arianna ventured inside to find her husband leaving just me and Mr. Bass in the hot tub exchanging small talk about the office while sipping on our drinks.
I didn't realize how late it had gotten till my phone started blowing up with calls and texts from Glen. I groaned as I saw it was already 12:30 in the night.
"Do you need to go home?"
I sighed, "yeah... I probably should." The disappointment must have been obvious in my voice. I had drank enough already my memory was getting fuzzy but I remember Mr. Bass sliding over to me in the hottub cause his leg brushed against me and I felt an unexpected shudder run up my body.
"I just don't get it you're such a bright young girl to be dealing with that." His leg was still brushing up against mine and I had the strong desire to reach out and stroke it. Just then my boss leaned in pressing up against me and he softly added "and so beautiful too."
I don't know what came over me but I looked up and bridged the gap between our lips in a pleading kiss.
The next thing I remember was waking up to the sunlight in a huge bed. I looked under the covers and noticed I was completely naked. Instantly I also noticed my pussy was throbbing from prior use. I rolled over and saw Mr. Bass laying beside me under the covers. I quietly sat up and located my phone on the night stand beside me.
Great... 7 missed calls and 13 texts from Glen. I signed and closed my eyes, he was too much to deal with this hungover.
I heard my boss begin to stir so I pretended to be moving in my sleep and rolled onto my side. He adjusted and rolled over towards me pressing his naked crotch against the small of my back. I found myself being spooned with his morning erection pressing against my skin and one of his large hands tenderly cupping my breast.
No wonder I'm sore... I thought to myself, he is massive! Involuntarily my ass began to sway against his manhood.
My movement must have woken him because he was now pressed firmly against me softly kissing my neck and claiming my tit for himself with his powerful caress.
Mmmm I moaned through a deep breathe. He took a pause from showering my neck in light kisses to whisper "Did you enjoy last night?"
I turned towards him so I could reach my hand around to explore the shape of his cock with my hand. I couldn't believe I had no memory of being fucked by the biggest cock I had ever felt...!
"It was the best sex I've ever had" I phibbed. I leaned toward him and kissed his lips while my hand massaged as much of his erection as I could grab.
And just like that he was on top of me and already inside me, giving my pussy assumingly a very similar pounding to the night before. My tits refused to stay still as they rocked back and forth with my boss's overwhelming thrusts. I began to get pushed against the bed frame as he drove deeper than I could handle. I moaned and cried with pleasure as my still half asleep body climaxed in a violent shudder.
I grabbed his back in my hands and pulled myself of the bed against his muscled body. I could feel my pussy fill with warmth before he even slowed down his strokes.
He stopped still inside me to catch his breath while I still vibrated from my orgasm. He gave my bruised vagina one last thrust and splash of cum before getting up and letting his seed seep out.
"Thank god I'm on birth control, holy shit boss that was unreal..." I gasped as I watched a waterfall drain from me and onto his sheets.
He gave me a knowing wink "You're welcome to stay here, but I should probably get you back to your boyfriend." He told me half amused.
I watched him put on a shirt and a pair of sweatpants while allowing myself one last glance of his glorious bulge before remembering now I had to go home and face my boyfriend...
