It’s funny how being a grown woman somehow gives a new perspective on your adolescent sexual experiences. For instances, if we all knew how strange the mechanics of sex can be would we have dared to even try having sex during the those gawky, self-conscious times in our life? No matter how much sex education one gets in school and how much gossip they hear from their friends I don’t think anyone is completely prepared to successfully navigate these experiences during their teen years.
Take for instance my “first time.” It is not the thrilling story I always dreamed it would be. I had been dating my boyfriend Jerry for about 18 months when the “big night” happened. Despite a lot of intense flirting Jerry and I had never discussed having sex. We never asked one another about our sexual histories. The topic of when it would happen, where it would happen and what kind of protection we would use just never came up. Don’t get me wrong, Jerry and I spent hours on the phone every night. We talked around the topic of sex like it was the proverbial elephant in the room, but despite making many suggestive maneuvers and logging hours in calls it was obviously a topic we both wished to avoid like the plague.
Jerry and I got together every Friday and Saturday night. For the most part our evenings were pretty tame. Hanging out with friends, making out, listening to music. Normal teenage behavior; nothing out of the ordinary. We started dating when I was about 15 and continued dating right up until that fateful night.
The “big night” came in January. I was 16, soon to be turning 17. Sometimes we would all go roller skating on weekend nights, but this particular night we decided to hang out at my friend Jennifer’s house. Jennifer had very little supervision so her house was a popular choice for our group of friends when it came time to make plans. That night it was myself and Jerry along with Jennifer and her boyfriend Donny.
Jerry and I were alone in Jennifer’s bedroom making out. Fast-forward a few hours and hands started to wander farther south than normal. Typically, Jerry and I kept our activities above the waist, but on this night I guess we were feeling bold. After the touching over the clothes got boring one thing led to another and we tried to have sex, but it didn’t work.
How, you ask, does one fail at having sex? I direct you back to the beginning of this yarn. The mechanics of sex are complicated. Jerry and I being the novices that we were didn’t take our underwear off. We tried to just push mine aside and he just used the hole in his boxers to free himself. More experienced lovers may have been able to navigate these sexual hurdles, but for us it wasn’t in the cards. Penetration took place so technically it counts, but when I say the whole experience lasted for roughly two minutes before it popped out I am being generous.
After the technical difficulties occurred we both simultaneously stopped our session of passion. To this day I am not sure if I was alone in the feelings of awkwardness and inadequacy I felt in that moment because I broke up with Jerry about a week later. Being young and naive, I was too embarrassed to face him. Years later we reconnected, but I never had the guts to ask if it counted for him.