Giving It Up

Everyone remembers it. Some of us remember it fondly, some of us have traumatic memories of it, and some of us have no feelings towards it whatsoever. I speak, of course, about losing our virginity. Almost everyone can tell you where they were, how old they were, and who it was with. Some people wish it had happened differently, some people wish it had been with someone else, and for some people, it wasn’t at all what they had expected.

I was 17 years old, and it was May of my Junior year of high school. I had previously dated someone for about 4 months, and while I was comfortable enough to give him blow jobs, I wouldn’t do anything else with him. I wouldn’t even let him in my pants in any way, shape, or form. Very soon after we broke up, my best friend since the age of 12 got his braces off and for the first time I noticed how damn cute he was. So, I did what has now become a pattern for me and asked him out. I guess I have always been an assertive kind of girl.
Things moved much more quickly with him than they had with my previous boyfriend. Not because I had more experience (because beyond kissing and blow jobs, I still really had none) but because the two of us already had an emotional connection. We were best friends, so we already knew everything about each other. We had already bonded and had already established a connection. So within two weeks of dating I gave him a blow job (which had taken 2 or 3 months with the previous boy) and he had fingered and gone down on me (which I had never let anyone else do). He hadn’t had much more experience than me, so it was a learning experience for both of us. This was kind of nice because I never felt intimated or that I wasn’t good enough or that I was doing it wrong.
Three months into our relationship, my parents went out of town. And we all know what that means to a couple of high school kids! It created the perfect opportunity for us. Not only would we have privacy, we would also have as long as we needed. No rush, no worry about what time parents were coming home, and no chance of someone walking in. Perfect. He bought the condoms. I don’t remember what was on the TV.
There was a lot of foreplay because we were both concerned about it being painful for me, which was pretty smart for a couple of teens who had never had sex before. In fact, he had been so concerned about sex hurting me the first time that he had been “preparing” me for it for some time. He did this with intense fingering sessions that involved inserting as many fingers as he could. Not that I minded; it was during one of these that I first learned that I was capable of female ejaculation. But I digress, as that is a story for another day.
By the time we decided to go for it, I was very, very wet. He had been fingering me for quite a while. Because of this, it didn’t hurt me at all when he went in (and he was not small by any means). I had expected so much pain and it ended up not hurting at all (though because of this, we figured the second time that we could just go for it with hardly any foreplay and that was a different experience all together), which was a total relief. In fact, it felt kind of good. The sex itself was awkward and clumsy as we both tried to figure out what worked best. We were in the missionary position and he was just trying to get the hang of the thrusting thing. I vividly remember that we were both sweaty and at one point our chests were touching and made a silly farting noise.
The sex was not over in minutes like I had expected it to be. The nerves, the condom, and the awkwardness of not know what he was doing had eclipsed the excitement of simply having sex for him. In the end, he never came. And after it was over, he did the most teenaged thing possible. He went to Wendy’s to get us food (romantic, no?) and had all his friends meet him there for a high-five (even more romantic, no?). He was, after all, the first in his circle to get laid.
Our relationship continued on and off for the next 2 years. He was, without a doubt, my first love. He remains, to this day, some of the best sex I’ve ever had (we slept together a few years after we broke up and the sex was just as good as I remembered it being). He recently got married and wrote me a letter before the wedding thanking me for helping shape him into the person that he is today. I would lose my virginity to him again in a heartbeat. So I guess that I am one of the lucky ones that has no regrets about how it happened or who it was with.
For what it was, it was perfect.
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  1. KBear
    Posted November 19, 2008 at 8:51 am | Permalink

    My first time was with the man I married. We were both 19, and I think it was the only time we both finished in

    Now, it just takes longer for both of us, which doesn't bother us one bit!

    Sweet story! loved it!

  2. April
    Posted November 19, 2008 at 10:59 am | Permalink

    My first time was so bad that I thought that sex was not all it's cracked up to be. I guess my reaction to what was going on was very telling because we never spoke after that. It could've been the fact that when it was all done I said, "Well that sucked." But who knows.

    My second time was very romantic and special, so that made it better.

    Love the picture. You guys looked very cute together.

  3. Apollo Unchained
    Posted November 29, 2008 at 4:29 am | Permalink

    That is so sweet, I love it.

    April, you crack me up. But my first time was even worse: we had to stop when she said, "You're disgusting." oooo, sad face :-(

  4. Greg (& Sheryl)No Gravatar
    Posted July 1, 2010 at 8:47 pm | Permalink

    This is one of the best virginity-losing stories I’ve ever read. Thanks for sharing

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