Crossdressing And Loving Men
Written by kevin
I have been crossdressing for nearly all my life. I had my first of many encounters with men when I was about 25. The first guy I was with was really nice. I was scared to death the day we met. We had talked for days about all of the things I wanted to do. The day finally came when we were to meet.
I got up and shaved and cleaned up really good. I did a full make up, combed out my blonde wig and got dressed in a the sexiest clothes I owned. I wore a black mini skirt with a red top and a matching white bra and panty set with thigh high stockings and my 3 inch heels. I had lit some candles, had some music playing on the stereo and had some wine to help me relax.
Paul showed up right on time. He was a few years older than me and he was very good looking to me. We talked for a few minutes and we sat on the couch. His cologne was intoxicating. We kissed for a few minutes, it was the first time I kissed someone else other than a girl, and it was weird. Paul began to touch my legs and rub his hands all over my thighs and it was driving me nuts. I started touching him and feeling his hard member through his pants. His hands were busy under my skirt touching me teasing me through my panties and making me breath very hard. We moved from the couch to the bedroom and started really fooling around. I found my self undressing him. Whipping his shirt over his head, and kissing him down his chest until I was kneeling in front of him and then I slid my hands up his legs and massaged his bulge before undoing his pants and pulling them down with his underwear in one jerk. He bobbed in front of me. I licked my lips as thousand of thoughts went through my mind. I leaned forward and tasted my first man. He was salty and tart and very hard. I slowly inched my mouth down as far as I could go without gagging. I licked and bobbed for several minutes and I could taste little squirts of precum that made my head spin. He was moaning and all and he pulled me to my feet and kissed me.
Then laying me on the bed he began to kiss me and lift my skirt up and reach into my panties to play with my throbbing manhood that was as hard as a steel pole. He lowered his head to my swollen shaft and began lick and play with my balls. He sucked and sucked and drove me crazy. He slowly started playing with my backdoor while sucking on me. He first found the lube that he brought and slowly smeared some around down there. He worked one finger in and started slowly screwing my backdoor with it, then he added a second and then a third until I was so out of my mind. He then slipped around so that we could sixty nine for a few minutes while he continued to play with my backdoor.
After he was really good and hard he had me get on my hands and knees and he lifted my skirt over my hips and slid a rubber all the way down his manhood and slowly started to part my cheeks. The first inch was very hot, the next several inches were a little sore, he was gentle he let me get used to it and then he gave me more and let me stop until I had the whole seven and a half inches of thick man in my backdoor. What a feeling that was. He held my hips still for several minutes while I adjusted to what I was feeling and then he slowly withdrew and slowly slid himself back in. He added a little more lube and then he picked up the pace of doing me and OMG did he make me feel wonderful. He did me for almost fifteen minutes until he filled the condom.
I lay panting on the bed with the feeling of having a orgasm without having one. I know it doesn’t make since but I felt a glow. He was more than ready to have me do him, I said I would do that but I had never done it with a guy, and since I couldn’t say no I did. He was very tight back there just like I must have been. It wasn’t as long as what he did me but I did manage to fill the condom and lay back on the bed to rest. We spent several hours laying there touching and talking. It was a great first of many times with guys. By far one of the best until lately. Im know 38 and found a stud that is around 22 who took me to new heights. I guess you could call me a cougar...lol. The young man who will be the next in my stories told.
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