My First Time

My First Time: Male, 18, California

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I started my first relationship halfway through my senior year of high school. She was a year younger than me — an outgoing theater type who loved that I could express myself with writing, and I was an awkward weirdo who loved that she could have boobs while wanting to talk to me. Before her, only one other person had that distinction.

I was insecure as a person, and she was insecure about our relationship. Before I left for college, she asked if there was anything I wanted to tell her about how I felt about her — clearly trying to yank the L word out of my mouth. All I could muster was, “I do really like you and I care about you a lot.” It probably would have hurt her less if I just went ahead and ran over her kitten.

When I went to college, her insecurities got even worse, but my feelings got stronger. I don’t know if it was the distance, or loneliness, or something real, but I started to feel like I was ready to honestly tell her what she wanted to hear. Eventually, we decided that the first time I came home from school, we’d lose our virginities to each other.

We fantasized about it together constantly — everything from that moment where we looked in each other’s eyes as I first entered her to that magical mutual climax. We both knew the first time together would be a perfect, incredible experience.

Three weeks later, I was telling her I loved her as I unzipped my pants.

She knew it was coming and it still hit her like a heart-shaped ton of bricks. From that moment on, every movement, every sound, every breath felt more intense, more meaningful. We both knew something special was about to happen.

Finally, we both fully disrobed, and the time came. It took me the length of the Roman Empire to open the Trojans, and an additional bronze age to put it on the correct way.

My heart began to race as she placed her knees on either side of me. Knowing what was about to happen, I began to shudder. I became so nervous that, in this warm room, with a very attractive girl naked on top of me, my penis wasn’t only flaccid; it was shrinking. It was incredible. I’d never seen it do it to that degree outside of the water before. It looked like one of those mushroom bad guys from Super Mario.

You’d think this would make insertion impossible — especially with a virgin girl. But test out your penis sometime when you just get out of a cold pool — when it’s at its absolute smallest. So there I am, sliding all 1 1/2 inches of what I’ve currently got inside of her. The look on her face didn’t convey that, though.

“Go slower. Put it in slower.”

“Sweetie, if I went any slower, I’d be going backwards.”

“Okay. Go backwards.”

I pulled out, and she decided to try lying on her back. At this point, I was no longer shrunken, but still flaccid, making any kind of insertion impossible.

So there I was on my knees in front of her, looking at her naked body, while holding my dick at the base, like a makeshift cockring and swinging it around in a circle, trying to get some kind of bloodflow. I guess that didn’t turn her on more.

I got on top in missionary, and after jamming my half hard penis into two thighs and a clitoris, she directed it in for me. I started to get a rhythm, and things finally seemed like they were working really well. This was the feeling I was waiting for. This was the magic I could never truly imagine in my wildest — and then she started to sob.

“Oh God, baby. I’m so sorry. I’ll stop, ” I said.

“No,” she said. “Keep going. I want you to finish.”

I wanted her to think I was enjoying it, too — to feel like this “perfect experience” was at least okay. So I kept pumping. “Maybe she just cries and says ‘ow’ when she’s about to climax?” Ultimately, like always, I wasn’t able to outthink my dick. It softened again, and I pulled out and tried to convince her that it was okay. “I’ll just finish myself off. I promise I’m fine, baby.” “Fine,” she said between sobs. I was relieved I’d at least be able to bring a definitive end to this disaster.

So there she was, staring at the ceiling naked with tears in her eyes as I pounded away at the dead snake in my hand. Now I was a swimmer and a teenage boy. I had yanked myself to completion several times. This wasn’t my first rodeo.

But I had never done it next to a crying woman. So five minutes went by, then ten minutes. I pulled off the condom. Fifteen minutes of nothing but faps amongst dead silence until finally, I willed some semen out of me. At this point she had stopped crying. I cleaned everything up, and laid down next to her. She curled up next to me, wiped her tears away, looked at me, and said, “That was perfect.” Then she hugged me tighter than ever and let out a satisfied “Mmm I love you.”

I looked up at the ceiling and thought, “Love is fucking weird.”