Oct 192015

So, my first time was a mix between fucked up, funny, and kinda sweet.

Some background: I had been dating a girl for a while in my senior year of high school. I was pretty firm against sex because I didn’t want to accidentally end up with a child that young and miss out on going to school. At any rate, things ran its course and, by the end of the summer before college, even though there was a connection between us, it ended badly. Anyway, I get to college and in my free time in my first semester, I found myself talking to one of her friends quite a bit. Whenever I was back home for a weekend, we would hang out. I wouldn’t call it dating or anything, but I suppose it could be construed that way; I KNOW some others thought as such and got pretty pissed. Well we got to talking more and more and more. Sometimes about sex and whatnot.

One weekend, I had talked to some buddies going to college near her and decided to come up to visit them. When I arrived (on bus), I could not get hold of them. Desperate not to sleep at a bus terminal, I called my ex, hoping to find a place to crash. As expected, I get a big “Fuck you” followed by an ended call. So, then I called the friend and she begged her mother to let me have a place to crash and I could go to my home in the morning to pick up my car (it should be pointed out that they were a year younger than me and I lived about an hour or so away from there). The next morning, her mother had to go run some errands but made sure she put the guy bumming a bed to use by doing chores around the house until she got back (don’t blame her really). At any rate, during a break, we were both sitting on the couch watching something or other on tv.

It was one of those teenage moments where everything is kinda awkward but exciting. A moment where your heart is beating out of your chest in anticipation of what may come. It was almost as if stars and planets aligned: we both leaned over and kissed. It wasn’t the best kiss, wasn’t the worst either, but it was tender and somewhat passionate. A kiss that expressed a longing and a desire to explore. As I was a big dummy 18 year old, speechless and caught up in the moment, she took the lead. She grabbed my hand a looked me right in the eyes, saying “I’m really nervous but I think I want to do this. Is that ok?” If my heart wasn’t beating out of my chest already, it had took a turn and was clear in my throat. I mustered up a “Yes, I want to do this with you as well.” We then go upstairs into her room and begin to make out in one of those awkward yet loving (well, not *really* loving but I am struggling for a better word here) manner. In a few moments, we built up the nerve to finally undress each other. Everyone remembers this and you are lying if you don’t: the first time someone sees you naked in this manner is an experience like none other, you are totally exposed and laid bare. It is a powerful thing.

We begin the process of fumbling each other in what we thought was foreplay (looking back its kinda cute and comical because we both had no idea what to do and were just kinda winging it). Now came the big event: it was time for intercourse. I put on the condom, gave her kiss, and went inside. Now, I went to high school in one of those real conservative areas where sex ed was generally not taught. People thought I was lying, but I didn’t know how to masturbate and never had masturbated (very odd, but very true).

It looked like it was painful for her, poor girl, but my God, it was the height of pleasure for me. I had never felt anything like that. Its embarrassing now, but I was a 2 pump chump. Not knowing what else to do, and seeing her still very much in pain, I just kinda rolled off, flushed the condom, washed up, and then laid down next to her. We said nothing but we stared into each others eyes, kissing each other every so often. We decided to try to make a thing of it after, but it fizzled. No hard feelings, it just wasn’t going to work and we both knew it. We kept in touch for a while but time passes, life goes on, people drift apart. Looking back it wasn’t the best idea to do that with my ex’s friend (LOTS of drama after that) but it was a pretty cute story to tell and, overall, a positive experience with someone that I won’t forget.

I hope she came away with a positive experience (I heard so, but never actually asked). I have gone on to get married and have a kid and love my life but I do look back so often and just remember. Names have been left out, mine included. However, if this story is ever come across, everyone involved will recognize it immediately and will get to understand what happens. I may not be the best writer, but hopefully I have conveyed the events in the most accurate manner.

  • Name: Guy
  • Gender: Male
  • Age of Virginity Loss: 18
  • Current Age: 32
  • How would you categorize your story?: Friend
  • Country: USA



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