Initial Crossdressing Adventures

Not sure what I was thinking, other than seeing my girlfriend making out and being felt up by another guy, but when Jim opened the door I allowed him to guide me into the backseat. He told me to scoot over and sat down next to me. He asked me if I was alright to which I wasn't able to answer. Jim had put his arm across the back of the seat which put it around my shoulders. My skirt had risen up to my stoking tops.

Jim turned and faced me all the time talking to me about how sexy, how hot, what a good dancer I was and how I was driving him crazy. I said something about having to get Sherry and go home and he responded "She's having a good time, so should you."

Jim had put his other hand high on my leg and was stroking from my knee to my stocking top. With his other hand he was massaging my neck and playing with my ear and hair. He turned my head to him and the next thing I knew was he was kissing me and trying to stick his tongue down my throat. I know the alcohol played a part but I was responding to his hot kiss. While he was playing tonsil hockey with me his other hand was working its way under my skirt. I guess he thought if his buddy was getting some that fast he was getting some as well.

When his hand hit my bare skin under my skirt, I snapped back to reality. I tried to pull my lips from his but he had a firm grip on the back of my head. I used my hand to grab his and pulled it out from under my skirt.

Jim got a little aggressive at this point and tried to go under my skirt again. I stopped him again. He broke the kiss and was clearly upset. He said, "What are you just a big cock teaser?" I was scared I was going to get found out and either be made a fool of or get the shit kicked out of me. I wasn't quite sure how to get out of this situation. I told him that I was embarrassed that I was on my period.

Jim relaxed a little with that and again kissed me. This time he took my hand and put it on his hard cock. He started working my hand up and down his jean covered rod. He kept working his tongue in my mouth and his hand that had been holding my head slide down and started rubbing my ass. Jim took my hand and brought it to his chest. I wasn't sure what he was doing until he brought my hand back to his cock which was no longer contained in his pants. He put my hand on his hard member and started jacking himself with my hand.

I had never touched another man before. Now I'm in the backseat of a car with some guy that I just met kissing him and beating him off. How does an all American boy wind up in this situation? Jim let go of my hand and I continued to stroke his shaft. His hand was now trying to unbutton my blouse; well actually he had already got a couple of button at the bottom unfastened. Once again I had to stop him before he found out I was not a woman.

Jim reacted unhappily again. We both had drank a lot and he wanted what he wanted. He again called me a cock tease. He grabbed my blouse and I was sure he was going to rip it off me. I was trying to push his hands off me and in doing so, slid down to the floor. This removed his hands from my top but hiked my skirt up to where my panties where showing and left me staring at his cock.

Jim took this as a good thing. He said, "Okay, if that is what you want, I'm fine with it since it's your time of the month." My alcohol dimmed brain didn't compute until he put his hand behind my head and pulled my face right to his dick. The lights went on when his cock head hit my lips. Jim was saying "Come on baby, you want to suck it, show me how good you are." I saw no way out. I stuck my tongue out and gave his head a lick. I then licked the entire length of his shaft, roughly 7 inches long. I was using my hand and tongue but that wasn't going to suffice.

Jim said, "Stop teasing and suck that cock baby." I opened my mouth and for the first time took a dick in my mouth. I sucked on the head and swirled my tongue all around it just like I enjoy it when Sherry does it. I then slid my lips down the entire length of his shaft. I was able to get it all in my mouth with gagging. I worked the entire length of his member bobbing my head. At the same time I was sucking as hard as I could and twirling my tongue around. After about 5-7 minute, Jim grabbed my head and drove his hips forward burying his cock into my mouth and started cumming. I hadn't planned on taking his spunk in my mouth but found myself with little choice as he pumped five or six squirts into my oral cavity. I couldn't hold it all and his cock so I was forced to swallow it as he was ejaculating.

After Jim was done shooting his load into my less than willing mouth, he stroked another 4-5 times before pulling out. He told me that I gave great head, really, has anyone ever had bad head! Jim tucked his cock back into his pants and said "We should get back inside."

With that he opened the door to climb out, leaving me half on the floor with my skirt over my ass and my panties showing. My blouse was untucked and had a couple of button undone. I scrambled out of the car pulling my skirt down. Jim said, "You've got a fine ass." Jim started for the club but I need a few more moments to compose myself and make myself presentable.

As Jim and I came to the entrance of the club I noticed the doorman had a smirk on his face. I walked in and immediately went to the table looking for Sherry. She was sitting there with Bill and when she saw me she went white. She got up and ran to me and said "Cindy are you all right?" She dragged me off to the bathroom and asked me what had I been doing, that I looked a mess.

When I got into the bathroom, I saw what she was saying. My hair was a mess, my blouse not properly tucked in, the seams in my stockings no longer straight, my lipstick smeared and a little bit of cum on the corner of my mouth.

I told Sherry what I saw her doing with Bill and what all had happened, well nearly all, of what happened with Jim and I. She told me that she was kissing Bill but stopped him from doing more and what I must have seen is just as she was stopping him from groping and fingering her.

After fixing our faces we decided to call it a night and made our way out of the bar. The doorman asked us, more me, if we had enjoyed ourselves tonight. Sherry answered with a smile, "I know I did and I think Cindy did as well."