This is the story of how I, an eighteen-year-old man, became my best friend’s girlfriend. No, it wasn’t a joke or a prank. We weren’t secretly gay. I wasn’t in drag or merely pretending to be his girlfriend. No, I actually became a girl – and well, you know, one thing lead to another.
Mike and I had known each other since we were both high school sophomores. We took Biology together. Our teacher was this balding middle age man with a saggy gut the jiggled like, I kid you not, a bowl full of jelly. Although the hair receded from the top of his head, it seemed to grow out from his neck and chin. He was prematurely graying too – probably because he taught high school students every day for a living – which gave his bushy beard a grayish color. Add that to the saggy gut and Mike and I had no shortage of Santa jokes to entertain ourselves during the long, boring class period.
“Hey Santa, where are the reindeer? Yo Kris Kringle, what’s up with sneaking into children’s houses in the middle of the night? So, this is what you do the other 364 days of the year while your elves slave away?” Okay, in hindsight, those jokes really weren’t that funny. At all. To anybody. But for some reason – blame it on being idiot male 15-year-olds – we thought our jokes were hilarious. For the life of me, I can’t remember the teacher’s actual name. We, just between the two of us, liked to call him “St. Nick with the Short Dick.” Mike and I were relentlessly cruel in our younger years.
I say that like it was forever ago. Teenagers mature a lot over those few high school years. As freshmen and sophomores, all we cared about was music, movies, and video games. And, of course, girls. Yeah, Mike and I both started early. Most of our friends started noticing girls around 13 or 14; we both started at 11 and 12. By the time we were 15 and 16, we were insatiable. Neither one of us had actually had sex, even though we both adamantly claimed otherwise. Truth was, we didn’t know a thing about women. We thought we did. But how women were in real life was very different than how they came across in movies and video games. Mike finally got laid when he was 17. It was simply a numbers game for him. He kept asking out girls until someone finally said yes. Kept trying to go as far as he could with them until they gave him an absolute no. But finally, at 17, he and his girlfriend actually had sex. Like three times. Then they broke up.
As for me? Well, somehow, I made it all the way to 18 still a virgin. The official story was I’d slept with over 20 girls by then, including some really popular cheerleaders. But in reality, I spent most of my time hanging out at home watching Netflix or playing Grand Theft Auto with Mike.
Or working. I got my first part-time job during that time too. The pay sucked. The hours were worse. But hey, I had money. So that was something.
Anyway, we both did a lot of growing up and maturing over those few years. Mike went from being a total goof-off to actually being serious about applying for top tier colleges. I bought a car, had to make payments, and held down a shitty fast food job. I think I ate too much of our own product though. I started getting a little soggy in my mid-section too – just a little – but in hindsight, I was an ignorant jerk to St. Nick with the Short Dick. Whatever his real name was.
Live and learn, right? It’s easy to judge others who are different than you, until you, through no fault of your own, start to become just like them.
By now you’re probably thinking that’s all well and good, or you’re totally bored with my backstory, and are like, “So get to the part where you became Mike’s girlfriend. WTF? How did that happen?”
Okay, I’ll tell you. But you have to promise to keep it a secret. I’m never going back to the man I was. I feel I need to keep that life separate. So, if you’re ready, let me tell you how it all happened.
I should warn you though – it’s a weird story for outsiders, for people who “don’t get it.” Remember, it’s easy to judge until it happens to you too. It’s easy to criticize another’s decisions, until you have to walk a mile in his – or her – shoes.
So before I begin, there’s one small detail I think you should understand.
Ever since I was, I dunno, around 13 or 14 years old… I always wondered what it’d be like to be the opposite sex. I’m not saying I felt I was born into the wrong body or had to dress up as a woman or anything. I was just curious. Maybe “curious” isn’t a strong enough word. “Fascinated” is a little more accurate. I wasn’t about to make any major life changes, but yes, I admit – some part of me always wondered, even occasionally fantasied within the privacy of my own imagination when I was alone in bed late at night, what I’d look like, how it’d feel, what it’d be like … to be a girl.
Weird? Maybe. For me, it was just … me. Who I was. A part of who I was, anyway. I had nothing against being a man. I didn’t hate my body or penis or anything. But … sometimes, now and then, I just wanted to explore that feminine experience.
And that’s exactly what happened.
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