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

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

... going to bed I headed to the garage and grabbed my special box. When everyone was asl**p I dressed in stockings, garter and my favorite panties. I pulled a t-shirt tight exposing my belly and looked at myself in the mirror. I have a thin build, long legs and kind of a perky ass. What very little hair I have I've shaved to make my dressing experiences feel more feminine. I slowly rubbed my hands on chest and ass, squeezing my cheeks and spreading them just enough to see my hole. I couldn't stop thinking about what Bob said and what this would really feel like if it were him doing this. I positioned my dildo so I could ride it watching my limp cock bounce around and then eventually becoming hard, I was whispering "yes Bob, do me" "mmmm yess baby take me" and eventually spurting all over my bedroom floor, imagining Bob cumming in me as well. A few days past, and it was Friday the company Holiday party. My s****r dropped me off at the party and told me to give her a call when I needed to her to pick me up. Joey was already there with a big smile, so we headed to the warehouse and drank a few shots laughing about school and just having a good time. I had put on a pair of my s****rs newest victoria secrets panties which felt amazing to me. Joey and I headed to the party in great spirits mingling and having a great time with the others. Bob came a bit late too with his wife and was introducing her to the company. He made his way over to us, said hello, made a quick introduction ...

... and walked away. Just as he walked away he looked back at me quickly, viewing me from head to toe with a little smirk. Joey quickly looked at me and said "what the fuck! what an asshole! what a weird look!" Joey and I grabbed some punch and poured the rest of his vodka into the two cups. We were both buzzed at this point and having a great night. Bob had already left with his wife but said he would be heading back to make sure the warehouse and office's were locked up. We didn't think anything of it, but both Joey and I knew we were closing the party down. It was about 12 am and Bob was back telling everyone to head home. In the nice guy tone he asked if everyone was okay to drive, if not he'd be happy to give them a ride. Joey took him up on his offer, so I quickly texted my s****r and told her I'd be joining Joey and Bob. Beside this would give me a chance to hang with Bob a bit more to see what he had meant by all of these weird comments to me. Bob locked up, loaded up his SUV with a few others along with Joey and myself and headed out. The drive was quiet for most of the trip and based on the direction he was taking it looked like I'd be the last dropped off. As Joey jumped out of the car Bob yelled hey Adam jump in front. I was in the third row of seats sitting uncomfortably so I jumped at the chance for comfort and yelled "Later Joey!" I was last to be dropped. We hit a red light and there was total silence with the exception of a faint holiday song on his radio. Keeping ...