A First Time For Everything

The other day at work I got in a conversation with a coworker on the topic of “firsts.” It’s amazing, looking back, at how much we can actually remember. I for one, can remember my first erection.

I’m not talking about morning wood. Morning wood was more of an annoyance as a kid. It isn’t until we become an adult that we actually realize the benefit of morning wood. Morning sex. My first erection, actually, was in 7th grade. I think I was a bit of a late bloomer. I say this because every morning at football practice I heard the guys in the locker room talking about a whole bunch of shit that I didn’t even know about. Jerking off, making out, fucking, etc. I mean, I knew about it, I just didn’t know about it. I was also one of the only boys running around without pubic hair…before we grew it out and then actually started shaving it off. Anyway, one day on the way to practice my dad stops at the gas station to get cigarettes, or cigars, or maybe just breakfast. So, I’m sitting there like always when this lady walks out of the gas station. ZING. I instantly looked down with this no doubt quizzical expression of what the fuck and said out loud…"shit." I thought I was broken, that something was wrong, and I panicked. Then it dawned on me. This was what the guys in the locker room are always talking about. I…have a hard on. My glorious moment into manhood faded when I realized my father was going to be coming back to the car. Quick. What do I do? I punched myself in the dick. That didn’t really work, but I tried it again anyway for good measure. I tried tucking it, but that hurt more than punching it. So…I simply crossed my legs…and prayed for the best.

I can still remember what that lady looked like to. Early twenties, shoulder length, straight, blonde hair. She was wearing blue jeans, flip flops, and a semi tight t-shirt. Ahhhhhh. The beauty of growing up in a college town.

He (the coworker) then told me the first time he got that boob grab. His was with the neighborhood slut. That older girl in the neighborhood that will let you feel her up…if you steal some of your parents alcohol. Hell, if she flashed you that was even better. Honest to god boobs, in front of your eyes. Without having to wait for that 28.8k modem. 30 second clip…3 minute download.

I honestly can’t recall which was my first boob grab (at least from memory, I can’t recall anything in my life that occurred before the 5th grade), it was either my 6th grade girlfriend JB, or my best friends (at the time) sister. If it was JB it was likely one of those instances where I kept crawling my hand up her shirt and she finally said, “It’s ok if you want to grab my boobs.” If it was the bf’s sister…well. Let’s just say the bf’s sister liked to have pretend sex. Which basically involved her sitting on top of me and grinding the holy hell out of my crotch until my dick was sore. We never kissed. No clothes were ever shed. There was no biting, or licking, or sucking. There were a lot of hands though, not on her part, on my part. I was constantly having to readjust, for one, so the same spot wouldn’t rub a hole in my cock. I can also distinctly remember my hands on her hips, feeling the motion…and the boob grab. She was easily an a-cup though, so I might have actually felt more if I grabbed my own chest. But goddamn’t…those were girl boobs.

Kiss? My first kiss? That was probably the single most romantic experience I have ever had in my life. It was actually with the bf. I was 15. 15? 15? I know some of you are probably saying…shit…I was already bone deep in some pussy (or handing out blowjobs like candy) by the time I was 15. Like I said, I was a late bloomer. Also, like I’ve been known to attribute to myself time and time again, I’m not exactly a ladies man. Anyway, where was I? I was 15, she was 16. We were at a park about a half-mile from my house. The park wasn’t secluded, but it kind of felt like that. It was around dusk. There was a slight rain falling. She was sitting on the back of her car. Glory be. I remember time standing still. Like there was no one else in the world but the two of us. I remember sliding my fingers along her wet face, tracing them through her slick hair. I remember the drops of rain splashing against my cheek, and it soaking my shirt and weighing it down around my shoulders. Her legs around my waist. I didn’t want that moment to end. Ever.

But it did.

We are not counting the little girl I apparently chased into the girls bathroom when I was in first grade and held down until she agreed to kiss me. At least, that’s what I’ve been told I did. Like I said, I can’t remember anything before 5th grade.

This is about the time we come to my first actual touching of a vagina. Here’s the thing. No matter how much porn we watch, no matter how much we brag as men, I don’t know a single man that probably fingered his first vagina properly. I was 16 this time, the day before I came to GA. This encounter killed everything but my first blowjob and first sexual penetration with a penis. I got to see boob, I got to feel boob, I got to bite boob. I got to finger a vagina. Finger…is probably not the best term. Prodding is more accurate. I got to prod a vagina. The first time my fingers crawled down the pants of a girl I was so goddamn excited I’m surprised I didn’t rip out her internal organs. My internal monologue went something like this:

Pubic hair! It’s soft, much softer than mine. Goddamn’t why won’t these pants give, I can barely get my fucking fingers down there. Wait. Wait. I think I’m touching vagina. I’m totally touching vagina! Where’s the goddamn hole? Finger search, finger search. There’s the hole! Isn’t it supposed to be wet or something? Isn’t that how people always describe it? Wet? Isn’t that what I always see in porn? Anyway. Fuck it. Slide the finger in and out. In and out. In and…wait…wet! Awesome!

Then it consisted of me…I don’t know…prodding at it with varying speeds for the next hour. I remember thinking, What the fuck! It takes me 3 minutes to jerk off. Why the fuck is this taking so long?. Ahhh, the ignorance of youth. She was a good sport though. I can’t remember if my penis ever even left my pants.

My first blowjob? I don’t even want to talk about it. Likely the most disappointing sexual encounter I’ve ever had (and likely the reason why I don’t like oral now) unless you count…

The first time I ever had sex? This…I…I don’t even know where to start. She was a whore, for one thing. Not a literal whore, mind you, I didn’t have to pay for it. Unless you count that half a bottle of Ritalin she stole from me. It wasn’t until later that I found out I lost my virginity, at 19, to a girl who had already lost her virginity…to 27 men. Yeah. There’s not much to say really. I didn’t get off (which I still haven’t), so no 15 second man for me. However, I did get to penetrate the pussy, therefore technically losing my V-Card. Woohoo! What a fucking waste of time.

So…there’s just a few examples of my firsts. I’ve been given the thought of doing this again in a less raunchy format. Something more along the lines of First Crush, First Love, etc. I might do that.

Anyone of you have any embarrassing/awkward firsts?