My First Time Pt. 1 - The Boss makes his move - Sex Stories

My First Time Pt. 1 - The Boss makes his move

... constantly made fun of him for being overweight. He stood about 6-0 and easily weighed 225 lbs. His belly poked over his belt a bit, but not too much. He was a hairy guy for sure as well, he was constantly scruffy but you could tell he had to shave his neck often. His chest hair would stick above his collar and was dark with some mixed gray and his forearms matched. He was serious guy, would joke around a bit, but a good guy as well. In my curiosity I had checked out Bob, looking him up and down. Trying to get glimpse of him in the bathroom. When he would have his team meetings he would sit in front of the team and I would constantly glance at his crotch, wondering if his cocked looked like my Uncles. I slid under the covers mad and confused, but let out a laugh. What a crack up! What if Bob was actually flirting with me? Holy Shit! No Way! I entertained the thought that night and ended up sliding my pj's off, grabbing my toy and fantasizing about Bob rubbing his big hands on me, pinching my nipples, grabbing the inside of my thighs and working his way to my ass. I slid a few fingers with lube and then worked my toy in. Picturing Bob at the end of my bed with his hands holding my legs up and sliding his cock in and out of me. I stuck the dildo to my headboard and fucked it like I never had before, ending in a loud whimper and massive cum shot and then collapsing on the bed. That morning before school I decided to wear jeans that weren't so tight and normal boxer style ...

... underwear to spare potential embarrassment at work. School ended and I headed to work. What the hell could the day have in store for me. It was the Holiday's and so the company Christmas party was that coming Friday. The Christmas decorations were everywhere in the office and warehouse. Last years party was a great time so I was looking forward to this one too. My buddy Joey in the warehouse told me he was bringing some booze this year. He and I would sneak out and drink all the time so I was up for it. I had to make a few copies of our shipping slips so I headed into the main office. I knew I would pass Bob at some point, but I was ready for it. And really didn't give a shit. I had about 20 or 30 copies to make so it had my full attention. "There he is!" Bob chuckled as he entered the printer room. "How's it going Adam?" "I'm good, you Bob?" I responded. "I'm good Adam too, ahh you changed your look, that's too bad" he laughed, "Pink is your color." he yelled before exiting. I quickly jumped to the hallway to confront him. Okay, now I know he knows and I know somethings up! He had closed his door to meet with our CEO before I could say anything to him. "DAMN IT!" I thought. I didn't see Bob at all the rest of the day, so before heading home Joey and I made plans on how we'd sneak booze into the party, so I agreed and told him I'd see him in a few nights. I had a few big tests over the next few days so a day off would serve me well. As soon as I got home I ate, studied but before ...