Head Games - Sex Stories

Head Games

One day at work a female coworker of mine who knew I had recently took a break and separated from my husband asked me for a favor. She had a friend who was very well to do and owned a prominent business within his community but he had recently divorced and was looking for someone to attend an awards ceremony with him. She asked me if I would consider it and even though I found out he was more than double my age I said, “what the hell, I’ve not got anything else going on that night.” The night came and I had only spoken to him on the phone thus far, but I had arranged to get dressed at his house instead of driving an hour back to my place after work, getting dressed and then driving an hour back to meet up with him. He eagerly agreed to allow me to prepare for our “date” at his place. Upon arriving at his place he met me at the door of an extravagant home. He appeared much older than I had even imagined, but I was already there and wasn’t going to back out on the guy. Besides, he was wealthy and I was bored. I brought my bag in and proceeded to the bathroom to shower and get dressed. He was a gentleman an didn’t bother me during the process. I exited the room, dressed and ready in a low cut dress that enhanced my already very full cleavage. I thought he was going to drool on himself. He was literally speechless which made me smile and eased the tension a bit. I was still skeptical about the difference in age so I needed some type of mental comfort at that point. We attended ...

... the ceremony and he received an award for his business or something. I really wasn’t paying attention and could have really cared less anyway. I was doing my friend a favor and that was it. The night ended fairly uneventful although he got a little handsy at the end, but I was a good girl and left as soon as we arrived back at his house. Needless to say he called the next day and requested a second date. I was still hesitant to be involved with this older man, but I reluctantly agreed. He picked me up in a very nice, high end car. He had sent me a HUGE bouquet of flowers for Valentines Day a few days earlier so I decided to give back by dressing in a short skirt, with a low cut top and heels. He couldn’t keep his eyes off me on the way to the restaurant so I knew I had his attention although I had absolutely NO intent on fucking this man. We went to a very nice steak house and had a wonderful dinner. I admit I may have had a little too much to drink which typically puts me in “the mood.” This was no exception. I was holding to my guns and I was not going to do anything with this man. I was literally afraid to. We got back into the car and he put his hand on my leg. I was trying to play it off but I was horny as fuck. Something about certain liquors just gets me horny as hell. I close my eyes as his hand rubs my leg. My pussy is soaking wet, mainly from the drinks, but wet none the less. As I opened my eyes he was leaning in to kiss me. I blocked the kiss and in the same motion ...