Where it happened: someone's apartment
Langauge: English
Sex: Male
Rating: 4
Category: Straight
My first time was a huge experience for me. First let me set the stage for you. It was the very beginning of 1997, New Year’s day actually. I had attended a new years party with a, well we didn’t quite know what we were in high school, but anyway I was with a girl I ran around with in high school. We had gone our own ways in college. She left the state I just went to Chicago for school.
When we were in high school she was a scared prudish girl. She never let me kiss her. Not at prom, not at graduation, never. Though we did have mixed feeling about each other. Well any way she gave me a call and invited me out for the evening. She sent her sister, only a year younger than me to pick me up. She looked like the Cheshire cat when she saw me and said. “If you stay with us tonight you are going to have the time of you life.”
When I finally saw MXXXXXXX She was not at all like she had been in high school. She had undergone what I now fondly refer to as the freshman freak. The common syndrome of young girls getting away from her parents for the first time and asserting their freedom. So the nice girl who had belonged to the youth group in high school had transformed. Her hair was shorter and styled and wore form-fitting clothes.
As we left her parent’s house she lit a cigarette and spoke through pursed lip. “I have changed a lot JOE. For instance I smoke and drink. Does that surprise you?” Well I have to admit I hadn’t expected this but I really wasn’t surprised. At the time I thought I had been exposed to some pretty gnarly shit during my first year of art school. I mean I saw entire class take breaks to go get high. So I was just like whatever.
So I endured a party full of strangers sober as I wasn’t comfortable getting drunk around any of them and I was the designated driver. I dropped MXXXXX sister and her boyfriend off at the flop earlier and was waiting for MXXXXXX to finish her flirting and drinking at the party. All in all it had turned out to be a pretty weak evening.
Finally we left and she was all over me. I had a hard time dealing with it because I had been rejected so many times previously. Finally we arrived back at the flop where MXXXXXX sister was fucking with her boyfriend. As he paid no attention to us as we entered the room MXXXXXX addressed her sister in a lilting voice,”Watch ya doin sis?” which was quickly replied,”Fucking..”
My tragic flaw being a gentleman asserted itself, as I was a bit embarrassed. MXXXXX continued her assault on me. A half an hour later she had finally coaxed my clothes off of me though I protested I didn’t want to take advantage of a drunken girl. Somehow all of us ended up on the bed as the sister talked to each other. They reached out and said,”lets give these guys something to really look at.” As they lightly caressed each other breast and brushed lips.
As the time to copulate came near I admitted my virgin status to MXXXXXX. Who was surprised and told me not to worry she would take care of me. The sex wasn’t good for either of us I don’t think. I was completely uncomfortable with the whole situation and unable to say no to someone I had wanted so badly in high school.
Though we occasionally still speak, it is usually brief and uninvolved. We shared one night together and moved on.
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