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Awkward Sex Stories: Laughter is the best medicine (after lube)

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It was the first night after I’d come back for my sophomore year. I’d convinced Stephen*, my unofficial boyfriend, that I needed him to stay with me during the first night because I would be alone in a suite that was meant for four.

He didn’t decline. Around 8 p.m., he arrived and we made the trek up the two flights of stairs to my suite. He sat on the couch in the living room while I rummaged for my HDMI cord, and once I found it we decided to watch “Luther.”

It was the typical “Netflix and Chill” anecdote. Five minutes into the show, his hands had found their way to my thighs. Ten minutes later, he gently turned my mouth to his, and we started kissing. This was the beginning of the end.

After a bit, I asked him if he was tired, and he replied yes. I suggested that we move to my bed, then, and we could go to sleep. He said okay. We went to my room, closed the door, and left “Luther” playing on the TV upfront.

We didn’t go to sleep.

I’m not sure if either of us were tired in the first place. But not too long after lying down, we were fooling around. On top of me, he whispered, “Do you want me to put it in?”

I thought about asking him jokingly what he planned on putting in and where, but I figured this wasn’t time or place. Instead, I asked him if he had a condom. He said yes. So, I decided I was finally ready to lose my virginity and said yes.

He went back to the living room and grabbed one out of his bag, while I lied on my bed awkwardly staring at the ceiling. I noticed some glow-in-the-dark stars stickers a previous resident must’ve put up. Sex under the stars, I thought. Romantic, I guess.

He came back with a condom, and I watched him open the packet with his teeth. After gliding it on, he hopped back onto my bed and we started kissing again. Next thing I knew, I felt a slight pressure between my thighs. It was finally happening. I was about to lose my virginity. I was ready.

I wasn’t ready.

For some reason, he could not get it in. He opened my legs wider, and my head moved towards the edge of my bed which was lifted four feet in the air. He straightened me up, and I giggled. Stephen paused.

“What’s so funny?” Stephen said.

“Nothing,” I said. And the truth was, I didn’t know what was so funny. But after that first giggle, I couldn’t stop.

I’m not sure if it was the odd movements that threatened to send me onto my bedroom floor or the awkward reality of my plight which proved that everything in my life had to be awkward, but I couldn’t explain why I was laughing. I still can’t.

We finally stopped. Everything we tried was either too painful or just didn’t work. Of course, I didn’t expect it to be perfect. But I figured since Stephen was more than experienced, he would know what he was doing.

I still don’t know if this technically counts as losing my virginity, but if I do know one thing, it’s that laughter is the best remedy to all awkward situations. At least I think it is.

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Student newspaper serving Tulane University, Uptown New Orleans
Awkward Sex Stories: Laughter is the best medicine (after lube)