I don’t believe most people’s “first times” were as magical and wonderful as they always dreamed them to be. At least mine wasn’t. In fact, it was so bad and unsuccessful that I don’t even think I can technically call it my first time.
My then-girlfriend and I had been in a relationship for quite some time, and both of us were virgins. After talking about having sex for a while, the day came when we thought it would be good to try it out and do away with our sexless selves.
We were in her bed and doing all of the usual foreplay things. Thoughts of the coming experience were swimming through my head. I had nerves. Oh boy, did I have nerves.
On top of that, I am very self-conscious and have a shy bladder. I can only pee at a urinal if there is nobody else in the bathroom. This does not make for the most confident man the moment he is going to have sex for the first time.
When we felt we were ready, we got into the missionary position, and I tried to awkwardly fumble my way into this girl. I wouldn’t call my penis small by any means, and I was having a hard time getting it in. I tried shifting my body and coming in at different angles. It just wouldn’t go in. Any confidence I had was gone. I immediately lost my erection, which made it even more difficult to guide in. It was like trying to blindly maneuver a strand of spaghetti through the eye of a needle while also holding myself up with one arm.
After rolling over and trying to get me going again, and then failing to get it in a few more times, I finally sort of got my mostly flaccid tip inside and immediately came.
It still stands as one of the worst sexual experiences of my life.
I’m just glad I dated this girl for a while before doing it; I can’t imagine the horrific embarrassment of going through all of that with a stranger. Luckily she didn’t immediately break up with me, and we were able to try again another day.
Unfortunately, when we went to try again, the past failure had only set me up for more failure. The pressure was too much and there was nothing we could do to keep me hard. We tried a few more times over the next couple weeks and the same thing kept happening. I was very embarrassed, and she was understandably frustrated. After the fourth time, we decided that we should just not try it and not even think about it for a few weeks until my mind could get far enough away from my inadequacies.
About six weeks after the initial disaster, we agreed to have another go. We were having fun and kissing when I felt that I could do it. I managed to block out all of the things that were weighing me down and got on top. I slowly and carefully found my way inside. It wasn’t the best sex, or even close, but I did it. I think the struggle of getting there made the triumph that much sweeter. I felt very accomplished, and now we could confidently say that we were no longer virgins. I can proudly say that I have never had an issue since.