Alphabet People - Letter J

“J” was my first “first.” J and I were going out and both virgins. I was a junior in high school, she was a senior. The guys I played ball with on the varsity baseball team assumed I wasn’t a virgin and I never corrected them. I didn’t want to undergo the ridicule that our left fielder underwent. He was a senior AND a virgin. The guys ragged on him so hard for his virginity and they laughed at him. And I ragged and laughed right along with them. Judge me if you must, but the guys gave me an out and I took it. I was only a junior and feeling fine that the seniors thought I was a plundering stud with a hot senior girlfriend. J and I decided to have sex and it was storybook. Prom night, all dressed up, and her parents were away. So clichéd. We went to prom and then I didn’t even know where to buy condoms. I called a friend of mine at a party that I knew was going on and asked him where to buy condoms and he laughed and told me to go to 7-Eleven. We went and got some and went back to her house. I was on top and tried to ease it in, but there was much awkwardness and she was in so much pain and I just wanted to stop, but she insisted that I continue. She continued to scream and I just wanted to stop, but she insisted that I keep going and said she was going to have to get used to it sometime. It ended up being bloody. That was my first “first.” We had lots of great sex after that, but that first time was traumatic. J and I split after seven months. I broke up with her when she went on to college. I was a selfish prick and wanted to be single entering my senior year.