Due to my shyness my high school encounters with girls never got beyond kissing stage. After graduating high school I took a couple night classes at the local technical school. In one class there was a girl named.Carolyn who was a couple years older. She had long dark hair and an average body from what I could tell. Her face was pleasant with a sly smile. We talked together a few times and hit it off quite well. One day I gathered the nerve to ask her out and she said yes. We went out to eat at a Mexican restaurant and when I brought her home she invited me up to her apartment.
Before long we were kissing. She was having her period and didn't want to have sex but did remove her top, revealing soft medium sized breasts with small pink nipples and quarter sized areolas. I got my first feel of bare breasts and was not disappointed. Then she jerked me off and I had my first orgasm in someone else's hand. I mentioned in earlier stories about my masturbation buddy Jim in my earlier teens; we had jerked each others penises a few times but not to orgasm. And that was practicing for when we had girls but this was the real deal with Carolyn!
We had a second date a few days later that ended up at her apartment again and her period was over. We were soon completely undressed and I got to feel my first naked woman. It was every bit as great 1as I thought it would be. I ran my fingers through her pubic hair and slid my fingers between her lips to feel my first pussy. She directed me where to rub her and in a couple minutes invited me to fuck her. Of course I accepted and slid my cock into her. The feeling was amazing. I was surprised how warm she was inside. My hand wasn't nearly as warm nor as good. I didn't last too long before cumming in her. My first time was not a disappointment in any way. I jerked off several times to the memory until our next date.
Carolyn and I continued to have a long relationship that I'll tell about in future stories.
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