Crazy Uncle Mike

The Greatest Loss of Virginity Ever

Recently I received some bad news, a buddy from grad school passed away unexpectedly. He was a good guy and absolutely a character. He also had the greatest loss of virginity history.

Let me tell you a bit about this guy. In many ways he was the living embodiment of Charlie Brown, right at the moment Lucy pulls the ball away. He dressed terribly, always in old t-shirts with a flannel shirt over the top, baggy sweats and sneakers. He always had just out of bed hair, even at 5 o’clock in the afternoon and had a 5 o’clock shadow every day by noon time. He also had allergies, and was constantly honking mucus with a sound that sounded like someone strangling a Canadian Goose. Not exactly an undergrads dream boy.

As such, and this will come as a surprise to know one, he didn’t have great luck with the women. He was an absolute consummate nice guy, he’d help anybody out, do anything for anyone in need. Of course this meant that he was really susceptible to being played by attractive women. Where we went to school, there was an unusually large number of really attractive undergrads. As grad students it made things especially interesting when teaching classes and we often had women come on to us hoping to find a way to get a better grade. And some of these women would play my friend, and while he was smart enough not to give away grades, they would work him for free meals or drinks, lead him on then blow him off.

Computers were in their early stages and we had computer classes in the computer labs on campus. One of the cool new features was the ability to message other people on the system in any of the labs. So my friend struck up a bit of anonymous friendship with a women who was often in the labs at the same time that he was. They would chat from time to time and even flirt a bit. One really rainy night there were very few people in the lab and he was happy to hear the ping that he had a message and he started chatting with her. She was upset, her ride was abandoning her and she was going to have to walk home in the rain and it was absolutely pouring. My friend asked what building she was in, turned out they were in the same building. So he offered her a ride home, and she said yes.

They agreed to meet out in the hall at 7PM and he was out their early and more than a bit nervous. She came down the hall and asked if that was him, she was absolutely gorgeous, 19 years-old, and a complete hard body. He was absolutely stunned and stumbling over his words and he noticed she looked like she’d been crying. They got out to his truck and in the truck she broke down, her boyfriend had abandoned her, she thought he was cheating, the whole college girl relationship drama. As they were leaving campus he asked her which way to go, she got quiet for a second and then said, “let’s go to your place.” Ok, so he started driving to his place, a bit confused, he didn’t see what was coming at all.

His studio apartment was a complete shit show, messy, old, peeling wallpaper and he had a screwed up parrot that he let fly around the apartment. Which of course meant that the bird shit everywhere, so when he left for school each day he covered the entire apartment in newspaper. So it’s a messy, old apartment with shit stained newspapers and an insane parrot. So when they get there, he tells her he has to go in and get his bird in the cage. Which is true but he also had to scoop up all of the soiled papers and make some attempt at straightening up the apartment.

Once in the apartment she sits on the bed and not the couch, again, he doesn’t catch the hint. He offers her a beer and they sit on the bed drinking the beer and she’s talking about how awful her boyfriend is and how she’s angry at him and it’s over. He still doesn’t get the hint. Finally, and I’m sure frustrated with a ton of hints she’d been dropping, she stands up, takes his beer, sets it on a coffee table and is on him. She starts kissing him, they fall back onto the bed. He’s of course wearing his sweat pants, he’s turned on, this is the first girl he’s ever made out with and she’s smokin hot. He’s really turned on, they start bumping and grinding and given the situation and the thin material of the sweats, he explodes.

Now this is the living Charlie Brown, at every moment in his life this turns into massive embarrassment, a screaming woman, total chaos. But in this moment genius strikes, he leaps up and rips off his sweatpants and underwear and she likewise undresses. He’s of course still turned and jumps back in and she tells him she wants him inside her. He fumbles through it and there he is, having sex for the first time.

Now, I learned about this event about a month after it happened when he decided to tell me and a friend about it. We were giving him a hard time, we couldn’t believe he’d kept this quiet and he explained that it turned out the boyfriend was on the football team. A huge and apparently angry man and my friend had been hiding from him for the last month because the woman had continued to call him. He was telling us because he was concerned and had a question. He wasn’t truly sure why she’d kept calling him, but finding out who the boyfriend was he had been completely avoiding her and she’d finally stopped calling.

So the question he had, was that he wasn’t sure how good the sex had been, he was actually afraid she might be angry about it. You see, he was confused, he’d just orgasmed right before they had sex, and he was of course nervous as hell, so it had taken him quite a long time to finish. He was also incredibly excited and so the sex was quite vigorous and he was afraid that he’d hurt her. We asked why and he explained that there were two things. First, she’d been screaming and moaning and he thought maybe she was in pain, but he was so excited he couldn’t stop. And secondly, after it was over and she got up, there was a huge wet spot on the bed. What he had thought was potentially bad sex was most likely the best sex she’d ever had. His first time and he’d come off as a monster porn star level stud, that’s why she’d been calling him. So while it was the greatest loss of virginity ever, Charlie Brown’s normal operating mode ended up making it a one-time thing.