Male, 17, New York
We’ve only been dating for two months. Apart from a few make out sessions, I was quite inexperienced — a novice in both sex and relationships. Jane already had four “serious” relationships by the time we met. Before I met her, I was quite addicted to masturbation. I was so used to my hand that I was worried no woman would ever live up to the high expectations of my non-conforming way of self-pleasure. To put it bluntly, I would pinch. I didn’t start to use the typical stroking technique until college.
I had three days to prepare. The day I was going to lose my virginity was set for Saturday afternoon. I was too shy to actually buy condoms, so I asked my friend Eric to lend me some of his. He gave me three of his leftovers he had hidden away in his gym locker.
That Saturday morning I was in the kitchen when I got the brilliant idea to test out my sex moves. This essentially involved me dry humping a pillow for fifteen minutes in my parent’s bedroom. Because they had a pretty big mirror in front of the bed, I had a clear view of how my body would look. Everything seemed normal. After the dry humping, I left the apartment and headed straight to the bus stop where we would meet.
I had initially arranged for a movie date, so that I wouldn’t have to face any awkwardness afterwards, but we ended up going to Starbucks and having some hot chocolate instead. As we were making our way to my apartment, she became silent. For a girl who had sex before (multiple times), I thought it was quite strange. I took her to my room where we kissed for what seemed like hours. I started to unbutton her shirt and caress her breast. Things were looking great, that is, until the actual sex.
She and I were both naked on my bed. I was on top. I took the condom out of my bag and tried to rip it open. I tried and tried and tried. I went to the drawer and got scissors only to realize that I could have used my teeth. My hands were so drenched in sweat that it felt like every finger was glued together. Back in bed, with the condom in my hand, I kissed her a few times; I was finally ready to use it, but there was a problem. The second the head of my penis touched the condom – it died. Romance over.
She asked what was wrong and I told her what happened. She jerked me off and we were back in session. I attempted to use the condom again but my penis, like a turtle, went back to its shell. This is when she screamed out a combination of words I wish to never hear again in my life: “You have a naked girl on your bed and you can’t get hard?!” I told her I was nervous. She went back to jerking me off to regain my manhood. This time I was ready. I was successful in putting it on. Though there was a problem – I put the condom on the wrong way. I took the condom out and it fell to the floor, she immediately said, “Get a new one; I’m not letting you put that thing in me.” I got out the second condom only to repeat the turtle dick technique once again. I punched the wall in anger and she told me to calm down and that maybe we can try again another day.
In addition to all this, I struggled to find the hole where the supposed magic would happened, even with my fingers. After a slight pause, I suggested we change positions. I was successful in holding my erection and getting the condom on while laying down in bed. I finally got inside her, or maybe I should say she got herself inside me, and in three quick pleasant strokes of her skinny body, I finally came. I was no longer a virgin. I smiled, but then realized she didn’t get anything out of it. Happiness was solitary for only a brief moment.
We’re looking for stories about the first time you had sex. Email firstname.lastname@example.org with 500-1000 words. (Don’t worry, we won’t print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.