Funny First Times

I’ve always been intrigued with people’s first time stories. They always seem to be funny and awkward or at least awkward in a funny sense.

That wasn’t my case, but hearing a bunch of first time stories recently got me thinking about a funny almost first time.

I met Fred* in the middle of my junior year of high school. We met at a friend’s party on a Saturday night. We went to different schools and he was a year older than me. I don’t remember exactly how we how we wound up hanging out with each other for the entire evening, but we drank and danced and I genuinely had a lot of fun with him.

When it was time for all of us to leave, he walked me to my car and asked me if I wanted to go out sometime. Sure, I thought. Why not.

Every Saturday night since then, Fred and I had our date nights. Usually, we’d go to a drive-in movie. I don’t remember most of the movies we saw, but we had fun and I always enjoyed his company. He always brought a six-pack of beer for himself and a bottle of Riunite white for me. We’d drink. Sometimes we’d get high and have ridiculous conversations that we thought were deeply philosophical.

And, yes, we made out. Hell, it was a drive-in after all. And, boy did we make out. He was fantastic. He was also respectful. He never tried having sex with me. If anything, he made a point of telling me that he wanted it to be special and that he definitely didn’t want to do it in a car. I really liked that about him.

Shortly after summer vacation started, Fred called me in the morning.

“Hey, my mom’s at work today,” he said. “Want to come over?”

Fred picked me up and we went back to his house. During the ride, he pulled out a box of condoms. He had a proud smile. Mine was a bit more devilish. We giggled and held hands and told each other how excited we were to finally have sex.

It felt funny being there in the morning. All the other times I had been there was in the evening when his parents weren’t around but his friends were. They were usually working on cars. Or drinking. Or both.

We wasted no time making out on the couch in the family room. Things got hot and heavy really quickly and soon my clothes were on a heap in the floor. It was the first time we had been naked together. It felt weird, strange and exciting all at the same time.

We got into some really wonderful foreplay as soon as we hit the mattress. Well, it was wonderful from the point of view of two teenagers of the age of consent that had been waiting weeks for the perfect opportunity to have sex. We had no idea what we were doing, but his kisses and his touches on my fully naked skin were a brand-new kind of excitement. I was getting hot, moist and tingly between my legs, but I wasn’t quite ready to give him my permission. I could see that he had gotten hard, but I was still a bit too nervous to hold it in my hand. Honestly, I didn’t know what to do with a bare, erect cock. I was sure that he would tell me what to do or that I’d eventually figure it out. I had to.

After a few minutes, we heard the door from the garage that led into the kitchen open.

“Oh shit!” he whispered in a panic. “My mom’s home! Hurry! Put your clothes on!”

A shade of chalk white fell over me.

“I can’t,” I said. “I left them in the family room. Remember?”

We scrambled in a panic not knowing what to do. He tried to think of a way to get my clothes and bring them back to me before she saw them. How I was going to get out of the house without it being an embarrassing situation for all three of us seemed like a long shot. I was more concerned about him catching hell from his mother than I was about giving her a very bad first impression of me.

Then there was a knock on his bedroom door.

“Fred?” said his mother from the other side of the door.

He didn’t and couldn’t say anything to me. He just pointed to the closet.

As soon as I slipped in the closet, I heard his bedroom door latch slip.

“Don’t come in, Mom. I’m sleeping and I’m not dressed,” he said.

There was a brief conversation in Ukranian between the doors. I had no idea what they were saying but it didn’t give me a sense of worry. It sounded like a mother and son who were just talking.

I stayed in the closet feeling more naked than I ever felt for a few minutes, but it felt like hours. Soon, he opened the door and let me out.

“My mom just went into the basement to wash some clothes,” he said. “I’ll get your clothes and get you out of here before she comes back upstairs.”

I had never gotten dressed in such a hurry. Fred tried to help me get dressed to rush the process before he hauled me through the house and into his car in the garage. He told me to duck underneath the dashboard in case his mom would see me. It turned out to be a smart move.

“Fred, where are you going?” I heard his mother ask.

He told her that he was going to a buddy’s house to help him work on his car.

I had never seen or felt Fred peel out of a driveway or anywhere so quickly. It wasn’t until we were half way down his street until he said it was safe for me to get up.

And then we breathed.

As it turned out, Fred’s mother had no clue that he had a naked girl in the house. A few days later, he suggested that I meet his parents and that it was about time that I did, but I couldn’t get myself to do it. I felt as if I would have this big scarlet “A” stitched on my chest.

We dated for about another month, but things just got weird for me after that close call. Fred was still the nice guy he always was. He hadn’t changed, but I found it awkward to be around him. We never consummated our relationship. I forgot what kind of bullshit story I gave him for not wanting to see him anymore. I felt bad about it. Guilty, even.

I never saw him again until about 17 years later a function at my sons’ elementary school. Actually, our kids’ elementary school. We shared quick “Hellos” and “Nice to see yous,” but we didn’t reminisce or going down Memory Lane. Not with our kids by our sides and his wife somewhere out in the crowd.

I still think of him with good, and even funny, memories.

What’s your favorite funny first time … or almost first time story? Write or post a link of your story in the Comments section.

*Name has been changed to protect the not-so-innocent.