Middle school and high school weren’t my time to shine. I was a scrawny, ugly child with a giant head. Kids called me inflate-a-head and told me I looked like Rocky Dennis.
Girls didn’t find me attractive. My antics and attitude didn’t help my situation either. I didn’t get laid until I was 18. I was a late bloomer.
At the end of my senior year of high school a girl finally noticed me. She was a pretty, petite blonde girl who also happened to be one of the more experienced girls in my class. To be blunt, she got around.
We would flirt with each other during sixth period computer class. She had a boyfriend, but that didn’t seem to matter. She was my only prospect, so I liked her.
One night we ran into each other at a party. She was drunk and I wasn’t. It seemed like a perfect opportunity to seize the moment. We kissed and she offered me a blow job to drive her to her house because she was too intoxicated.
As much as I appreciated the offer I had to decline. I had gotten a DUI more than a year prior and lost my licence for 18 months. I was about to get my license back and I didn’t want to risk losing it for longer if I was caught driving without a license.
My friend stepped up and offered to drive her car. Her and I got into the backseat of her Suzuki Sidekick. My friend and another girl got into the front seats. Within a few minutes she was blowing me in the back seat. The other two people in the car started to laugh with disgust as they realized what was going on.
I wanted to keep this night going so we went back to my house because my mom wasn’t home. I took her downstairs to my bedroom and took off her clothes. I had no idea what I was doing. I wasn’t even sure how my dick was supposed to work in this process. Could I stick it in her limp? I tried and she laughed. She told me it didn’t work that way.
Once I figured out the logistics of sex, I slipped inside her for the first time and it felt magical. Well, maybe not magical, but I was thrilled to finally lose my virginity. I pumped away for what seemed like an eternity. Finally I was about to cum and I told her. She grabbed my ass cheeks, held me inside of her and told me not to stop because she was going to cum too.
I was afraid to cum inside of her and she could sense it. She looked at me as I was about to cum and said “Don’t worry, just cum in me. If I get pregnant, I’ll tell my boyfriend it’s his baby and make him pay for the abortion.” I came and then instant sadness rushed over my whole being. I had lost my virginity, but I couldn’t get her words out of my head.
I laugh about this now, but at the time it was disturbing. This was the springboard into a long line of awkward sexual experiences that still, fortunately or unfortunately, continues on today.