My First Time

My first sexual experience is a difficult thing to pinpoint. I spent my teenage years with the same boyfriend, starting at 14 (March 2002, freshman year of high school), up through 18 (August 2006, sophomore year of college). I wasn’t exactly a late bloomer, but I certainly wasn’t ready to lose my virginity at fourteen. Fifteen, still no, but maybe I can try a handjob, and I guess you can finger me. Sixteen, no, but let’s learn oral sex. Let’s give me my first orgasm, my first mouthful of cum. Seventeen, almost, so close, then two weeks before my eighteenth birthday ok sure, let’s give this thing a try.

Those three years leading up to this moment, Alex (my high school boyfriend) and I had a totally sexually fulfilling relationship. We had a delightful track record of orgasms to offer one another, with our hands, our mouths. We were wild children who fooled around in the back of his van (Oh! What a crying shame when he traded that van for a PT Cruiser! Oh the humanity!), in dressing rooms of department stores, in parking garage stairwells and the back rooms of my church.



This is me, around the time I’m talking about, curled up with Alex. His face is cut out, though I don’t know that he would know it if I failed to respect his privacy.

At this point in my life I was so wrapped up in stereotypical ideas of sex and virtue that, I shit you not, I gave my boyfriend my virginity as a birthday present. It was his 20th birthday, and about two weeks before I turned 18.

When we finally decided to “go all the way,” something changed. I can’t tell you if it was wearing a condom, or anxiety, or just one of the mysteries of the universe. But once his penis started spending time in my vagina, Alex lost the ability to maintain an erection. Over the final eight or nine months of our relationship, I could probably count on one hand the number of times we completed the act of copulation. Sometimes I think this was a big part of why we broke up.

Sometimes I also wonder if “losing his/my virginity,” in big official culturally acceptable terms, was just too much for him. Because up until that point, he could negotiate with his Catholic brain that he was maintaining our virtue, that we were going to wait until we were married. By teen logic, we were both still virgins until penile-vaginal penetration occurred. But once we transgressed that, maybe it took things too far for him.

Virginity is a big deal in our culture, but for me “losing it” was mostly about being afraid of being penetrated. Alex wasn’t exceedingly large, but anything bigger than two-fingers was a big step for me. I was right, it did hurt the first time, but that was brief and really not major for me. What was major was trying to figure out what it meant when my partner suddenly couldn’t maintain an erection anymore. Was there something wrong with me that wasn’t pleasing him? I had no idea, and neither of us had the ability to communicate freely and openly about our sexuality, because no one ever told us we were supposed to. Sex was a thing that you did or you didn’t do – it wasn’t a thing you discussed in a frank, objective manner. His guilt was immense, and I was confused.

Sex with Alex never got better. And that’s a shame. It’s not a great “how I lost my virginity” story, it’s just a true one.


4 thoughts on “My First Time

  1. Hi Star,

    This is beautifully written. And I am so thrilled you started this blog. I linked you from mine. 🙂

    I waited until I was 23 to lose my virginity…can you believe it? And it hurt like hell.

    I’m working on a story, so stay tuned! I also want to read up a bunch of your entries. I have some reading material for a while.



  2. I lost my virginity thanks to Monty Python.

    I was 15, with a 16 year old girlfriend. I was, as any boy can tell you of that age, horny all the time. I don’t remember making any decision to “give it away”, rather, it was basically “Opportunity Knocks, GET IN THERE.”. My girlfriend was already sexually active previous to our relationship, so there wasn’t much in the way of discussion or even a feeling of it being “special”. It just was. I will say that I wasn’t unprepared.

    We had met up at school and talked a bit, but hadn’t really spent time together. I used to take advantage of her car ownership to get the hell off campus for lunch. Monty Python was a well known theme of our friendship, with a lot of quotes and jokes tossed around. One afternoon, she asked if I’d like to come by to her house that evening to watch Monty Python’s Meaning Of Life. I said yes, shot my Dad a call after school and went home with her. We sat down in the living room, not even really together, her on a lounge chair, I on the couch. The movie finished, and there were some predictable jokes and select movie quotes. A few hi-jinks later, I’m sitting on the arm of the chair and it just seemed to happen that we were kissing. I looked at her and said, “Well, this seems to be foreplay. Now, we all know the purpose of foreplay.. BIGS?”
    She said, “Oh.. uh.. don’t know, sorry sir.”
    I said, “Well, the purpose of foreplay is to cause the vagina to lubricate, so the penis can penetrate more easily.”
    Then I started to undo her pants and she said, “No NO! You don’t just go rampaging for the clitoris! I had better show you how it’s done… in my bedroom.”

    And at that point, we adjourned to the bedroom. As a 15 year old, I had no idea if or when I’d have another opportunity, so I decided to do ALL THE THINGS. There was both cunnilingus and fellatio, several flavors of groping and fondling and a good three or four actual penetration positions. I exhausted the entirety of my knowledge of sex… and myself.

    She was under the impression for many years that at that point I was already an accomplished man-slut. In fact, she didn’t know it was my first time until nearly 15 years later, we met up again as adults and I told her. She was shocked.

    So, that’s my first time story. Hope everyone enjoys. 🙂

  3. Pingback: Cheating Confessions, Part 2: His Best Friend’s Penis | A Certain Star

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