Virgin No More

Okay, so this is the unfortunate story of how I gave up my ass-ginity to some random dude from Hot or Not. 

So, this was way back in 2014, it was like the summer between Junior and Senior year, and holy sh*t I was so ready to just get f*cked, and get all this virginity nonsense taken care of. I thought I was like this huge loser because a dick hadn’t slid up my butt yet, and I was already 17 years old, which is like 35 in gay years! I had a serious case of FOMO, and I desperately wanted to be grown-up already, so I irrationally downloaded that stupid Hot-or-Not app that everyone had back then.

Hot-or-Not was like the predecessor to Tinder, where you still swiped left or right, but you also rate people on their looks. Super great app for a teenager to have, right? Like all of your self-esteem based off of a rating by complete strangers. Anyways, that’s where I met Robert, and he was like 21 years old, so I was totally like ‘F*ck yeah, got myself a daddy’. We messaged back and forth for a couple of weeks, and I was under the impression that he wasn’t a complete freak, so we made plans to meet up and get down.

I’m a small town boy, was raised up in the mountains, where the closest city, where Robert lived, was an hour drive through a winding, treacherous canyon. So, that being said, I decided that I should stay the night down there with him so that I didn’t have to go through that sh*t twice in the same day. The only thing is that I was still a minor, and still under my parents control, and obviously they’re not going to just let their darling baby boy go off to the big city to be alone with a stranger, so I called up my friend Baylee.

I had covered for Baylee when she went off with some dude to lose her virginity like a few months earlier, so it was totally her turn to assist me. So, I told my Mom that I would be staying the weekend with Baylee, and then immediately made the journey down the canyon over towards Robert’s house. I was an idiot, and forgot my toothbrush, so I texted him to meet me at the local Walmart, and that’s when sh*t started to get weird.

So, I’m in Walmart grabbing a toothbrush, and he comes around the corner, and he’s cute, not like super cute, but cute enough to get the job done. I notice that he’s like extremely f*cking awkward though. Like he comes up and gives me this really weird side-hug, like the kind that’s really uncoordinated and lasts a little too long, and doesn’t look me in the eye, or anything. 

Obviously the vibes are already not that great for me. Like, I’m being my normal bright sunshine-y self, and he’s just this big ball of cringe, like I wanted to just shake him, and tell him to stop making things so weird, but you can’t just force someone to not be socially-handicapped. So, I just told myself that his weirdness was endearing, and tried to get the hell over it. 

Flash forward to where we’re finally at his house. His parents were gone for the night, and he had to watch his little brother and sister, which was no biggie to me, or so I f*cking thought. I mean, the kids were nice, like a lot more sociable than their older brother, but they were also like really annoying too. 

Like, I was there to get my bussy pounded, yet I found myself being forced to f*cking clap to some third grader’s super lame magic tricks, and literally watch an hour and 45 minutes of goddamn Tinkerbell. The whole time I’m like glancing over to Robert, who’s on his f*cking phone, desperately trying to subliminally message him to save my ass from all this bullsh*t.

After the movie, Robert finally suggests we head to the bedroom. You know, like the thing THAT I CAME THERE FOR?? So, halle-f*cking-lujah to that. We get into bed, and he puts on Kill Bill, which I really like, but it’s like a 2 hour long movie, so I literally just fall asleep. Like, I’m so over it by that point.

I wake up, and it’s the next morning. Robert says that he tried holding me last night, but I pushed him off me, which is like really f*cking weird, because anyone who knows me knows that I’m like the biggest cuddlebug ever. So that should’ve been like the most critical red flag of all. I start to laugh, but he stays dead silent, so I just like slowly stopped. Like, jeez, learn to f*cking laugh, huh?

5 minutes of silence later, he turns and kisses me. Now, I’d seriously never kissed a boy before, so my heart was THUMPING hardcore. He chuckled and asked if I was nervous, and I just told him this was all a new experience for me, then he turned and asked if I wanted more, and of course I nodded like a total complete virgin.

So, we’re kissing, and then he starts weaseling his slimy tongue past my lips, and I’m like quietly hyperventilating because I hadn’t even practiced making out before, and now it’s literally being shoved down my f*cking throat. To make it even worse, the dude’s mouth was like suuuuper f*cking nasty. All I could taste was cigarettes and sour morning breath, and he just kept wiping his tongue-sludge inside me again and again. I wanted to scream so f*cking bad, my stomach was literally churning with disgust, but I just sat there like a dead fish, waiting for this absolute torture to finally end.

I was in complete shock. I could feel the rotten bacteria swarming and multiplying on my teeth. Robert moved down to my dick, and tried sucking me off. What was supposed to be a pleasant experience, my first blowjob, was completely and utterly ruined. That same gross-ass mouth was now touching my penis, and Little Chase wasn’t having it. I tried to think of sexy thoughts, but I couldn’t fly over the rainbow into Bonerland, so I was stranded in Flaccid City. If that wasn’t embarrassing enough, Robert looked up at me with this weird look on his face, and pulled one of my pubes out of his mouth. Which, in retrospect, he can just f*ck off, he’s lucky I didn’t puke in his mouth after that disgusting oral assault earlier. 

Then, Robert get’s up and grabs condoms and lube. Meanwhile, I’m thinking WTF, when did I ever say that I’m ready? After everything, I’m like the opposite of horny, like the furthest state from aroused that someone could possibly be. But, back then, I was kinda a pussy when it came to breaking bad news to people, and I didn’t want to hurt his feelings by telling him that my butthole is totally off the table now. Which is a trait that put me in soooo many f*cked up situations in my life. So I let him between my barn doors, and thus I was ushered into the world of post-virginity.

He was pretty small in the cock department, so I wasn’t like in tears or anything, but holy sh*t it’s not fun. Just imagine the constant feeling of a turd that’s begging and pleading to get the f*ck out of your bowels, like I’ve never been so uncomfortable in my entire life. Everyone says it gets better, but they’re liars, you totally have to be some sort of masochist to find this REALLY pleasurable.

So, there I am in missionary position, with a dick in my ass making me feel like I really have to sh*t ASAP. I just want to disappear, but instead I’m having to listen to a stranger’s loud grunts and moans of ecstasy. God, his facial expressions made me feel so uneasy, he was trying really hard to be sexy, and it was so f*cking obvious, it wasn’t cute at all. He stared at me the whole time, wide-eyed and like a hawk, like he was trying to look into my soul or somesh*t. I couldn’t handle it anymore, so I just squinted my eyes and looked the other way. 

As he did his job, I gazed around his room. He nailed a f*cking skateboard to his wall, like who does that sh*t? It was seriously the only decoration he put up. I couldn’t tell what was worse, the sex or his terrible interior decorating skills. 

Then, it happened. He shut his eyes, threw his head back ever so slightly, and let out a deep wale. He finally came, so we got up and got dressed. I walk out into the living room, and I’m greeted by his f*cking parents. They apparently got home at like 3AM, and I imagine they heard literally everything that just went down. They make me sit at their dining room table, and cook breakfast for me. I was just sitting there thinking, “You know your son just dumped a load in me, right?”. We all ate breakfast like a big happy family, with me masking the grueling experience that just occurred with a big fat smile.

Robert wanted me to stay another night. I was buggin’ out, like a repeat of all of this sh*t was completely dreaded. But, both luckily and mortifyingly, Robert got a voicemail. He said it was from some chick named Sherry at a hospital. And, I was thinking to myself what a coincidence, because my Mother works at a hospital and name’s Sherry. But that couldn’t be possible, I’m like an hour away from home, with a dude that has no connection to my small town’s local healthcare facility. But, I was horribly and stupidly wrong.

You see, Baylee sold me the f*ck out, so my Mom went ape-sh*t crazy and went online to see my last phone calls, like some nutcase stalker. I was so f*cking embarrassed that my Mom would even do that, and after she interrogated Robert, I was ordered to come home immediately, which happened to be the lucky part of the whole entirety of this horrendous situation.

So, I did. I told Robert I had a fantastic time, which was a complete lie. I wish I would’ve had some self-control, and just waited for the right person.  I couldn’t believe I let myself do that. It was my first time, and I gave it to a basket case with morning breath and a serious staring problem. Lucky me, am I right?