1. Jessie and the Office Girls


    Date: 10/16/2015, Categories: Crossdressing, Author: JessieCD

    ... wanted to have an office affair with. Just prior to the end of the day, I was cornered by Dan and Aaron. Dan had pushed me down to his crotch level, and placed his pants covered crotch at my mouth, while Aaron went behind me, grabbed my hips and mock-thrusted into me from behind. I was quite embarrassed as Dan and Aaron were making a lot of noise and jokingly commented about the weekend slut. I was red with embarrassment and quickly slunk away hoping no one saw my humiliation happen. The rest of Monday was uneventful, and I met Tracy at her office. “Dan and Aaron sure did a number on you this afternoon. Don’t worry, only myself, Karen, and Sue saw what happened. I feel bad that you were humiliated at work. Let’s go out and try to forget about what happened.” I felt re-assured as I walked out with Tracy hand in hand. We hopped into her car and drove to a local dive bar that was known for their burgers, fries, and tap beer selection. When we walked into the dive bar, Tracy got a smile on her face and yelled out, “Karen! Sue! Glad to see here! Mind if Jesse and I join you?” “Sure!” Karen replied. Tracy grabbed my arm and dragged me to where Karen and Sue were sitting. I was really unsure of this. It seemed too coincidental, almost like a set-up. I played along as I really wanted to see if anything would happen between me and Tracy. The time at the dive bar was a lot of fun, there was no mention of what happened at the office. I was totally relaxed and had enjoyed the evening so ...
    ... far. Tracy finally told the girls that it was time to go. I got up and followed Tracy to her car, fully expecting the night to be over. Instead of going to the office to get my car, I noticed a very familiar area, and realized that we were in Dan’s neighborhood. I started to become uneasy when Tracy seemed to read my mind. “Jesse, I’m sorry if this is making you uncomfortable, I am not ready for the evening to end quite yet. I just want to have a nightcap with you.” We got to Tracy’s house and went inside. Tracy excused herself while I sat down on the couch in her living room. After several minutes, Tracy walked out and I really thought I was having a dream. She was wearing a sexy pink babydoll that barely covered her crotch area. I was rendered speechless by the sexiness of her body. After a couple of moments of silence, Tracy finally said, “Kitty got your tongue?” I was still speechless because I was entranced by her pink babydoll and how it hugged her curves. “After the weekend you had, I think you deserve the attention of a hot and sexy accountant who has been the subject of many of your office affair fantasies.” Just then, she came up to me and gave me a kiss. I finally started to come out of my stupor and reciprocated with a gentle and passionate kiss. She replied how soft and sexy it was, and how it felt almost womanly. We kept kissing with more and more passion. Tracy grabbed my hand and led me to her bedroom. Once we entered her bedroom, she pushed me down onto the ...