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How I Almost Lost My Virginity

<Then Eventually Did>

So when you are a 16 year old kid you’re an idiot.

You  think you’re smart, and will fight anyone who says otherwise.
You know things but only when you look back do you realize that you were an idiot…

This is one of those stories.

So it’s the summer of Freshman into Sophomore year and I’m just turning 15. All my friends are excited because there’s a big party being planned at a girl’s house because her parents are going away for the weekend, taking the little sister, and letting her be alone in the house.

I was dating (or seeing or whatever your allowed to call that dumb —-) a friend of the friend hosting the part.
<sidebar>  in my high school at this time no one was really dating… it was all more about the label of “I’m seeing you…” and this whole stupid back and forth.

<double sidebar>
I went to the smallest public high school in NJ. So when you live in a heavily populated area but only have 60 to 70 kids per grade [small town in middle to upper class area w/ a lot of private schools] this stupidity happens.

Anyway me and this girl I’m kinda dating. We went out on a bunch of dates but there was always something weird about her {I later found out that she was both anorexic and bulimic} but I didn’t know at that time.

<Sidebar> Even if I did not sure I would have said anything bc she was a smokeshow with the secret nick-name of Stuff-Her-Phany <aka-Stephanie> my own little affectionate private joke among friends

*Back to the story*

At the time I rolled with the cool kids and was luck to have older brothers who could get my friends and I beer & liquor. So everyone knowing this I was the man who was able to come through with the alcohol.

Showing up to the party feeling good about life getting my drink on I’m loving the attention from everyone saying “I’m the man” bc of the booze.

Stephanie shows up and we’re playing this little cat and mouse game but finally we start chatting and drinking… the night progresses well

About 3 drinks in or what felt like an hour or so of time

She takes me up to the bedrooms. It’s the classic “you’re not supposed to go up there…” that area is off limits, but she knew the girl that was throwing the party.

<funny side bar I also had a crush on her but that’s a story for another time>I’ll just say high school politics + one of my friends liked her so you know the way that thing goes…

So we go into the party host’s bedroom and start making out.  We lock eyes and it turns into ‘oh snap, I  think this is gonna go somewhere…’

Not gonna lie I got a little nervous and say “let me just run downstairs and go get a couple beers, I’ll be right back” so I run down.

In doing so I also seek out one of my friends. At this point in my life I don’t know much so I’m scared by those health class videos of getting someone pregnant the 1st time you have sex.

I find my friend Sean who’s the only guy in my friend group who has popped his cherry. I know he would always walk around with a condom in his wallet because he was the cool guy.

I run up him and I’m like “Sean Sean Sean!!! Hey any chance can I borrow your condom” and he’s like “borrow? what do you mean borrow???” I’m like “um well… you know –  like idk… I might need to use it or turn into a water balloon…”

He looks at me and starts laughing. Then hands me a white plastic thing that just says in black lettering “CONDOM” on it. As I’m walking away, he goes “Are you sure you wanna use that?” I’m like “yeah yeah… worst case scenario I’ll give it back…”

The response was “don’t worry about it.”

So much like every other person forced to take those boring health classes I never really paid attention. I remember the condom on the banana thing but I was too busy thinking of jokes to say.

 I’m noticing that this condom is in a pretty large package but proceed upstairs anyway. Stephanie is sitting there on the bed listening to Radiohead (one of my favs at the time) and when I come in we immediately start making out. Within a couple minutes she’s like “hey let me go to the bathroom and freshen up.” I’m like “OK” so I’m quickly down my beer.  

Now I swear to you for a second I’m thinking she’s either sick or taking a nervous poo because she’s in there for like 10 minutes +

She eventually comes out and she’s in a cute little outfit and I’m just like “ohh, so let me freshen up for a sec.”

I’ve heard in the past other guys not being fresh down there. Also this was a time when we all just got pubes no one I knew shaved them yet, so everyone was rocking a Bush – very 70s chic.

Thinking about popping my cherry now, I instantly get hard.

I take out the condom and I’m thinking do I put it on now or wait?

I decide to unwrap it and the circumference of it is like 3”
That’s when I start freaking out. How does this thing work? Is it like vacuum sealed when you get it wet? or does it shrink when it gets wet?

I start overthinking things freaking out a bit. I’m like wait a minute I have a normal to slightly above average ====} …this doesn’t make any sense

Not to sound — but playing sports and after gym class I know what the rest of the crew is rolling with so I’m fine. In addition to that looking at dirty mags and porn in the past something is off. But I’m not willing to risk that so this turns into a full meltdown.

I go out and Stephanie is on the bed and says do whatever you want. I’m immediately say I’m not feeling well and run out. I go downstairs and bounce without saying anything to anyone.

I didn’t know what to do!

 I just went home and on the way I throw the condom in the woods.

Following day my friends are calling me up. They’re like “dude what happened Stephanie was all kinds of pissed off and doesn’t want to talk to me anymore. I just said I thought I was gonna get sick. We all meet up later that day and my boy Sean asks me “hey what did you do with that condom?” I tell him when I was going home, through the woods, I ended up throwing it out. He starts to laugh and says that was probably I good thing. I’m like “what do you mean”, he goes “well because I don’t think it would have fit.” I take a step back and I’m just like “wait what are you talking about???” and he goes “yeah dude, I don’t think it would have fit any of us – it was one of those condoms from Spencer’s”

“Spencer’s?” I reply.  “Yeah it was one of those joke condoms”

Sigh… WTF

I was never able to fix the situation with Steph. Sean and I still remained friends.

If you’re curious how it eventually happened I use this as a stepping stone to come up with the bravado of my 💩 doesn’t stink (mainly bc I’m good at sports).

I didn’t lose my virginity until much later. I wanted the 1st girl I banged to be so hot everyone else would pale in comparison. Let’s just say a good conversation with my two older brothers helped me realize that was stupid. A few years later it ended up being a friend of a friend’s girlfriend who was a couple of years younger than me.

We ended up hooking up watching ‘Varsity Blues’ and listening to Dru Hill. At first, I was a little bit shaky but because we were drinking I ended up being a rock star. She had to tap me out after about 40-45 minutes. Never thought it could hurt after the chick climaxes a few times.

The best part was her brother was upstairs and he knew me through baseball, as well as a couple of mutual friends. We were the same age. Best part of the whole this was him knocking on the door a bunch of times trying to ruin the mood. But once his girlfriend came over he got distracted and then it was game on for me. Kind of funny situation that we were both banging in the same house but in different unsavory ways.

Tell me how I’m doing! It’s okay to provide constructive criticism. I’m trying to get better at this.

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