My Best Friend’s Boss

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I often stopped to visit Madeline at her job for a couple of reasons. One, because she gave me free drinks and snacks when I came in and two, because her boss, Oliver, was drop-dead sexy. He was this mysterious Italian man with a perfect head of dark hair and deep tan skin. I knew he had a crush on Madeline, even though she denied it. She was the type of person who didn’t read cues very well, but I could see the way he looked at her while she was behind the bar.

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It was a Tuesday night, so the place was closing early. There weren’t a lot of people in the bar anyway.

“It’s just you and Oliver here?” I asked, stabbing my last olive with a toothpick and putting it into my mouth. 

“Don’t get any ideas, Lizzie,” she said, rolling her eyes at me. She pulled her apron off from around her waist as she got busy wiping down the bar. “Are you sticking around until I’m done?”
Before I could answer, Oliver appeared from the back of the bar, looking as handsome as ever.

“Lizzie, hi,” he said warmly, smiling at me. “I knew I’d see you here.”

While Madeline was out of earshot, I pulled Oliver aside and grilled him about his love life. I made sure not to make it too nosy, but Oliver seemed like an open book. He was single and living a bachelor’s life, he said. Madeline really shouldn’t have been so surprised when she came around the corner to find us making out.

“You guys! What are you doing?” she cried, sounding affronted.

“Your friend is a very persuasive woman,” Oliver said, grinning at Madeline. “Are you sure you don’t want to join in the fun?”
Madeline glared at me, but I had known her long enough that I could recognize something else behind her eyes. She was excited.

“Let me shut the drapes,” she said, heading over to close the big velvet curtains that lined the bar. 

The bar was one of the nicest ones in town, with ambient lighting and the most beautiful, dark décor. It made sense for us to all file into one of the huge leather booths on the far wall of the bar, as it would have the most space for the three of us.

Madeline and I sat side-by-side as we pulled our shirts off over her heads.

“How did I get this lucky?” Oliver said breathlessly, observing our bodies. His dark eyes were wide and astounded. “You two are both so gorgeous.”

He reached around to undo both of our bras at the same time, with one hand, and he did this so deftly that it made me wonder how many threesomes he had had before. Considering he said he had been living a bachelor’s life, I figured he’d had quite a few.

Madeline and I started to undress Oliver at the same time. His body was exactly as I had imagined: slim, toned, and tan. He picked up the table that sat in the center of the U-shaped booth and moved it aside. This gave my best friend and I space to start sucking his cock.

“Fuck!” he hissed, as we stuck out our tongues and began to slide them on either side of his shaft. “That feels amazing, girls.”

Madeline and I took turns sliding our mouths down his thick length, bobbing our heads before letting the other have a chance. Oliver put a hand on each of our heads, running his fingers through our hair. Already, my pussy was throbbing.

Oliver slid his cock out from between her tongues and told us to take off our pants. He watched us get naked before his eyes, and then he had us spread our legs. 

Madeline and I looked at each other, giggling at the same time. We had been best friends for years but had only ever briefly made out in college. We hadn’t done anything like this before. I was the one who leaned over first to grab her face and kiss her.

“Mmmm,” she moaned against my mouth, and suddenly, Oliver was down on the floor.

His mouth connected to Madeline’s pussy while he began to finger mine. I was sticky and wet as he parted my labia, slipping into my hole. I pulled my mouth away from Madeline’s, unable to control the loud whimper escaping my lips.

Madeline and I shivered and moaned beside each other while Oliver pleasured us both at the same time. I looked over to watch his tongue glide over my best friend’s clit. She was clearly enjoying herself just as much as I was. Oliver knew just what to do. His fingers were sweeping back and forth in my pussy, bringing me closer and closer to the edge.

I was the first to cum. I couldn’t hold it back. I bucked my hips against Oliver’s skilled hand, fucking his fingers as I came. My whole body was all shiver and shake, and I could hear him moan his approval against Madeline’s pussy. 

I pulled away from Oliver’s hand and began to suck on Madeline’s nipples while he ate her out. This added sensation seemed to do the trick, and her breath started to quicken. In just a few moments, Madeline was also cumming, and Oliver was there to lap up every drop of her juices.

Once she was finished, Oliver leaned over to my pussy so he could have a taste of me as well, and then he twirled his finger at us, motioning for us to turn over. Madeline and I leaned against the back of the booth with our asses sticking out as Oliver caressed us both.

“Two beautiful girls, two perfect bodies,” he said, sighing deeply.

Madeline and I looked at each other. She was flushed in the face and was biting her bottom lip. I was going to make a cheeky comment, but I was interrupted as Oliver pushed his cock into my pussy.

“Holy shit!” I cried out, my fingers tightening their hold on the booth. “You feel so big!”

Madeline watched with envy as I was fucked from behind. She scooted a little bit closer to me so she could brush my hair behind my ears and kiss me. Our tongues intertwined as I was filled up, again and again, by Oliver’s big cock. Every thrust filled the empty bar with the sound of skin hitting skin and my wet pussy. I couldn’t believe this was my best friend’s boss fucking me on a Tuesday at their workplace.

Oliver pulled out from me after a few moments, asked Madeline to turn around, and plunged his way into her now. I helped out by pulling her legs up and apart, giving him deeper access to her hole. It was mesmerizing to watch his cock stretch her out with each thrust. She was just as wet as I was, if not more.

“All these months working with you,” hissed Oliver, “and I had no idea you had such a great pussy.” He grinned at Madeline. 

“That’s how I feel about your cock,” she replied, her voice breathy.

Oliver took his turn with both of us. He fucked us from behind, then on top, then from behind again. We each had our turn of riding his cock as Oliver sat there and pulled us into his lap. I wasn’t sure how long we fucked for, but we were all covered in sweat by the time we were spent. Madeline and I had cum at least three times each. I couldn’t believe Oliver had that much stamina, especially at the end of a shift at work.

Finally, he stood in front of us and told us he wanted to spray us in cum. Madeline and I were excited about this, of course, so we sat on the edge of the bench with our hands in our laps and our tongues outstretched.

“I wish every day at work could end this way,” Oliver laughed as he started to jerk himself off. “Why don’t you guys move your tits for me?”

We did as he asked, still dizzy and weak from cumming so many times, and definitely eager to please him. We squeezed our breasts together and jiggled them up and down. I tugged at my own nipples, giving Oliver a good show that quickly caused his cum to shoot out of his cock and all over me and Madeline.

“Holy shiiiit,” he grunted, tossing his head back as he came. The cum never seemed to stop coming. It sprayed all over our faces and breasts, hot and thick.

When there was finally no more cum left for us, Oliver let out a low whistle and looked down at me and Madeline, who were completely messy now. He laughed. “Let me go get you girls some rags.”

Madeline and I looked at each other and began to giggle.

“Was this what you thought was going to happen when I came to visit you at work?” I asked.

“Not at all.”

Oliver came back with the towels, and my bestie and I began to clean each other off. I couldn’t wait for her next shift.

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