My Dad's Boss

Hey guys. This is my first story here so please forgive the mistakes if any and enjoy!

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I just celebrated my 18th birthday a few days ago and was finally looking forward to losing my virginity to someone. I always had fantasies about an older man taking my virginity but i never thought it would come true.

I was at chilling at home when my dad came back from work with his boss in tow. I discreetly checked him out. He was definitely in his mid fifties with salt and pepper hair that made him look hot. He was also very muscular and towered over even my dad who was 6 foot. He was insanely attractive and had a dominating presence. I was so busy staring at him that i got startled when he introduced himself to me.

"I'm Shane. It's a pleasure to finally meet you. I've heard great things about you from your dad." His gaze roamed over me and there was an appreciative glint in his eyes.

"Nice to meet you too. We're happy to host you. Please make yourself at home." I replied.

All throughout the dinner i could feel Shane's gaze on me like a physical caress. I liked the attention and basked in it.

"Alex, you are free these days right?" Shane asked.

"Yeah. I'm kind of looking for a job right now."

"That's perfect actually. Would you like to do a paid internship with me? It will be a great opportunity to broaden your horizons and gain a lot of knowledge."

"That is a wonderful opportunity. You should take it Alex." Dad chirped in.

I've had some difficulty finding the right job for me and this was an amazing chance for me to earn some job experience. Also the cherry on the top was working for this hot older man.

"I'm very grateful for this opportunity Alex. I promise i won't let you down."

The smile he gave me was downright sinful and gave me goosebums.

"So, I'll see you tomorrow at the office at 9 am sharp."

The next day I was already at the office at 8.45 am wanting to make a good impression. Soon i was called inside where he gave me certain tasks to complete throughout the day including shadowing him on meetings and jutting down notes from those for now.

During the first meeting I nervously stood behind my boss jotting down notes as people talked about big plans for the company. When boss asked for my opinion on something my heart raced but I managed to share my thoughts. After the meeting ended I was assembling my notes when Shane called for me.

"You were a really good boy today. I liked your input on the situation. You should keep participating like this." Shane said.

Hearing boss call me a good boy made me hard. I was embarrassed at my state and tried to hide my boner. I mumbled a quick thank you boss and was about to leave when he noticed the bulge in my pants. He looked a little surprised but his eyes darkened with lust.

"You liked that didn't you? Me calling you a good boy." Shane taunted.

"U-uh no boss it's not like that."

"Then why are you so hard?" He smirked.

I was really ashamed and said something incoherent looking down at the floor. He stood up and walked towards me stopping a breath away. I could smell his spicy aftershave this close and my mouth watered. He grabbed my neck and made me look into his eyes.

"Do you like this baby?" Shane asked.

"Uh yes" I whimpered.

"Good." He said then kissed me. The taste of him and the feel of his tongue sweeping across mine was complete bliss. His continued kissing me while he palmed me through my clothes. I groaned at the contact. He continued palming me and i was soon a whimpering mess.

"Please." I begged.

"Not now baby. The fun is just starting."

"You ever been with a man before?" He asked.

"No."

He seemed really turned on by the fact that this was my first sexual experience. He commanded me to strip for him and show him my virgin asshole.

"You are so beautiful baby." He said and started rimming me. The sensations were strange but felt so good. I moaned loudly and he licked harder. He pulled away and spit on my asshole. I was a little scared but also excited to pop my cherry.

"You ready my little slut?"

I nodded not being able to say the words.

He took out his cock and it was really big. He was hung and had thick veins and a big mushroom top which was already leaking precum. I got scared looking at it. He positioned his cock at my entrance and he slamed in thrusing his entire length into me without warning. I screamed at the blinding pain in my asshole. It felt like my asshole was being split apart. Shane murmered soft words and encouragements and started thursting into me in long strokes while his hips bounced against my asscheeks.

"Fuck you are so tight. You are mine. My slut taking my cock like a good boy." Shane moaned his pace increasing.

Each stroke spread the pain like jolts of electricity. But slowly the pain subsided and a different sensation replaced it. It started to feel good the pleasure increasing with each thurst.

"Aaahhhh fuckkkk." I moaned loudly.

"Look at my slut taking this cock so good." He pounded me harder groaning.

Shame burned my cheeks but my cock hardened loving the degradation.

"Aahh ahhh yess i am your slut ah fuck"

"Fuck yes baby. You love this don't you? Taking your boss's cock in your virgin ass filling you up and stretching your asshole."

"Oh goddddd yesss i love it ahh i love taking your cockkk"

He groaned, his pace increasing "Such a good little whore! Beg for my cum. Tell me how much you need it."

"Oh god boss please breed me. Give me your cum. Fill my belly with your seed. Cum inside me please. I beg you."

"You have been such an obedient slut. So greedy for my cum. This time you will get what you want." He fucked me hard till he came deep inside my ass. He then took my cock and jerked me off till i came on my belly.

He gave me a kiss on the head and started cleaning up our mess.

I finally lost my virginity and looked forward to more such days working under him.