When I stopped by the office Saturday afternoon to pick up the iPod I had forgotten there the day before, I was surprised to find the door unlocked. I walked in and said "hello" into the empty room. I heard my boss, James, say, "Hello?" back from his office.
I started to walk over, saying, "Hey James, it's Evan. I'm just stopping by to pick up..." I trailed off when he came into view. He had turned around in his chair to face me. I'm used to seeing him buttoned up in nice shirts, but today he was just wearing a black tank top and jeans. He's 43 years old, 20 years older than me. He's tall and dark haired, and I'd developed a bit of a crush on him since starting to work there a few weeks before. Now I was rendered speechless by his muscular, hairy arms, his firm pecs, and the thick, dark hair showing over the collar of his tank top.
"Picking up what?" he asked me. I looked up at his scruffy face and realized he was smirking at me.
"Oh, uh, just my iPod. I left it in my cubicle yesterday," I said. I realized I was blushing.
"Were you just checking me out?" he asked, smiling.
"What? No!" I said, too quickly.
"It's okay. I've been checking you out for weeks," he said, standing up.
"Really?"
"Yeah. Come over here." I walked into his office towards him. When I got close enough, he grabbed the front of the tight white t-shirt I was wearing, pulled me toward him, and started kissing me. I loved the feel of his beard and mustache on my face as he kissed me deeply.
He pulled back and smiled at me. "I've been wanting to do that since I first met you," he said. Then he started kissing me again. I reached out and starting rubbing his chest, particularly his nipples. He moaned and starting rubbing my chest too. I moved my hand down and rubbed his cock through his jeans. He was clearly hard, and thick.
Suddenly, he broke off our kiss, sat back down, and pulled down my red basketball shorts. "Nice," he said when he saw the jockstrap I was wearing. He rubbed my dick as it strained against the fabric of the jock. I moaned. Then, he leaned down and took my dick in his mouth through the jock. I moaned louder as his warm, wet mouth moved up and down my dick. He pulled off of my cock and moved the jockstrap aside so it stuck straight out at his face. "You've got a beautiful dick," he said. I knew it was just average, but the way he said it, I knew he meant it. A second later, he dove on my cock, taking it all in his mouth and sucking it hard. He grabbed my ass and pulled me closer to him, then started moving his lips up and down on my dick.
Clearly, James knew what he was doing. He was amazing. After about five minutes, he stood back up and started kissing me again. He stuck his hand up my shirt and started rubbing my chest and stomach, making me groan. I undid his belt and opened his jeans, pushing them down around his ankles. He was wearing gray boxer briefs, and his thick, hard dick was clearly defined through the fabric. I grabbed it and he moaned loudly into my mouth.
In one swift move, I dropped to my knees and pulled his boxer briefs down. I took a long, admiring look at his dick. I leaned in and licked up the shaft from the base to the tip, then took his head in my mouth. "Oh, yeah, please, suck me," James moaned. I looked up and made eye contact as I slowly worked my lips down the shaft. It wasn't very long, but it was thick enough to make me have to stretch my jaw. I fondled his balls in my hand as I worked his shaft up and down with my lips. He leaned back against his desk, put his hand on the back of my head, and seemed ready for a long blowjob, which is just what I gave him.
After what felt like half an hour, my jaw was starting to get tired. I pulled off for a second, and he immediately pulled me up on my feet and kissed me deep. Then he turned me around, bent me over his desk, and shoved his face into my ass. The scratching of his beard on my cheeks complemented the warm, wet feel of his tongue on my crack. "Oh, James, don't stop," I groaned. I couldn't believe the boss I'd been fantasizing about was actually eating my ass. I was feeling very grateful that I had taken a long, thorough shower before coming into the office.
Without moving his attention from his tonguing, he pulled open his bottom desk drawer and groped around for a minute until his pulled out what I realized was a condom and a small bottle of lube. He pulled off my ass and said, "I wanted to be prepared in case this ever happened." I looked behind me and saw he was grinning broadly. "Can I fuck you?"
"Yes, please," I said. He tore open the condom packet with his teeth, stood up, and rolled it over his dick, which he then lubed up. He also covered his fingers in lube and started to open me up. By now I was very eager to feel him inside me. I didn't have to wait long. He lined up his dick to my hole and slowly started to plunge it in. I moaned deeply. He grabbed my chin and turned me face so he could kiss me as he started to slowly move in and out.
James grabbed onto the straps of my jock as he picked up speed. He began grunting rhythmically and he pushed his thick cock in and out of my hole. I realized that I was moaning loudly as well. I started to worry that someone else would decide to stop by the office and hear us, but a deep thrust quickly refocused me on the amazing pleasure James was giving me.
"You're so tight," he whispered in my ear between grunts. "I could fuck you all day."
He did fuck me for the next hour, leaned over his desk, then me on top of him on his chair. I was worried it would break, we were bouncing up and down so exuberantly. He pushed all the papers off his desk and fucked me on my back, his desk repeatedly banging up against the wall. He leaned down and made out with me frantically as he fucked me, and his hairy stomach rubbed against my rock hard dick. It was in this position that he shouted out, "I'm going to cum," then pulled out of me and tore off the condom. I grabbed my dick as he stroked his own several times and shot and shot a huge load all over me. Seeing my hairy, butch boss cum and feeling it on my stomach and chest was enough to send me over the end. I shouted out as I came, adding my load to his. He smiled at me, started rubbing it in, then leaned down and kissed me gently.
"That was amazing. I hope we can do it again," I said when he came up for air.
"Hell yeah we can do it again," he said, grinning. "In fact, I might need to add this to your job description."
This is the first story I've submitted to nifty, so I'd love some feedback. PLEASE email me if you liked it, if you have any suggestions, or if you just want to be email penpals. If people liked this one, maybe I'll write another chapter. Thanks for reading.