Every young man’s goal in life is to make their father proud, but honestly I could give two shits about my father. He was always there for me in a literal sense, but he was never there for me in a metaphorical sense. By that, I mean that I literally had to teach myself everything about becoming a man… or at least the internet did. This is an anecdotal story following my journey into manhood, sex, and some things best forgotten.
My story starts at 17. I’m a young white boy, top of my class, but bottom of my social circle. I wasn’t hated, I just wasn’t popular, and I didn’t have many friends after abandoning them all from my 8th-9th grade year to play bass guitar in a band. My band story is for another day, but lets just say it expanded my mind. I was tall, 6 footish, brown hair kind of guy, who was torn between a love for boobs and a love for booze. I began lifting weights towards the end of my sophomore year, and to my surprise they expected me to play football after making perfect attendance to every morning lift. I’d be damned if I didn’t have a clue what the fuck I was doing. Defensive end? Tailback? Cornerback? I had not a fucking clue what I was doing, but I stuck it out and made a few friends along the way. I’ve always been good at politics. Anyhow, after sophomore year, me and some of my newly founded best friends began breaking into the local party scene. My parents were still arguing out parts of their divorce, so they rarely spoke. This gave me and my buddies the perfect setup for not getting caught. I think my parents knew, but never really thought anything of it since I was so “smart”.
February of Junior year, we break into a cabin and throw this massive rager. I’m talking 2 feet of snow outside, but there’s 150+ people just getting shit face crazy. I’d drank a good amount at this point in time, so I was able to hang with most of them. I shotgunned a beer with my buddy Beaner and shortly after I’m talking to this total 3 on the hotness scale. I’ll call her “Lady Dipper”. Why? Because this girl was into chewing tobacco like no other. She was also studying to be a power lineman if that tells you anything… Needless to say she was practicing for her career that night. She managed to climb the “pole” of three different guys. I was allegedly one of them, but I don’t remember because I blacked out and pissed all over the wall. The next morning, I wake up to her across the room laying on the bed. I’m curled up on the floor in a room that was maybe 20 degrees. All the doors were busted off the hinges and there was a sea of bud light flooding the house. My buddies came, picked me up, and we got the fuck out of there before the cops showed up. This began my ongoing party life to perfect my social skills.
Fast forward a bit, it’s now April and I realize I need a prom date. I don’t believe any of the rumors about the Lady Dipper, and I feel like my friends were just saying it to fuck with me. I’m desperate and horny. I buy this $300 book on the internet about how to pick up girls. I read that fucker front to back 3-4 times, and listen to the audio book twice on the way to and from school. I start trying it out on this girl that hit me up on Instagram. Although the lines were kind of… sexually explicit, she is super attractive, so I knew that it worked. I was psyched! (I’ll call her Tammy from now on).
Tammy, is getting super turned on by my comments about her getting tied down and whipped. She even calls me Christian Grey, who believe it or not I thought was an actor??? I ask her to prom, and I planned on sealing the deal afterwards. Prom night rolls around, we get a bottle of Jager and get drunk as fuck. I drive a Polaris RZR and she gives me an over the pants handy. FUCK YES. We both walk in and we begin the 2014 season of Dirty Dancing. Holy shit I was getting a boner. Is this normal? Fuck? She’s going to think I’m some perverted fuck. I double down on it and began grinding my dick into her ass like I’m trying to crush up my addies before a long night of cramming… and boy was I planning on cramming. She ate that shit up. Of course, my dad was out of town and I was already sick of him treating my mother like shit, cheating on her while they were married, and a bunch of personal shit like never playing pass with the football, teaching me to hunt, or to work on cars. Fuck him. Party at his house! He is out of town, so I throw a 20-30 person party in his garage. I realize I left the liquor hidden at my mom’s house, so I down a couple brewskies with the broskies and ask Tammy to ride with me. (I do not condone drinking and driving, it is stupid and I am stupid forever doing it). We pull up to my mom’s house, and I ask her if she’d like the “grand tour” (I probably made a winky face or something, I can’t remember). Fast forward, we’re in the upstairs living room/kitchen, and she just blatantly asks “well, are we going to do this”. I couldn’t have picked an easier girl. With a random stroke of luck I was about to land it with a girl who was like the female version of Bill Cosby. She was the kind of girl who was super slutty and you’ll probably catch something, but I was somewhat buzzed and realized I didn’t want to be a 40 year old virgin so I took my opportunity. It was like I had a giant neon billboard flashing RAPE ME, so we began making out and that’s about the time I realized there was nothing in the book that prepared me for having sex. Woops.
But I’m smart, so they say. I begin improvising by trying to take her bra off. Seems like a good start. Boy was I wrong. That shit is like trying to solve a rubix cube blind folded. I fumbled aimlessly at her bra until finally she gave up, took it off and revealed her luscious breasts. I’m no math teacher, but I was probably looking at a C cup. I coped a feel, grabbed her hand, and ran it down my chest toward my bulging cock. It obviously wasn’t her first rodeo, within a couple seconds she had my belt ripped off, fly down, and cock in her mouth.
As my dick slid into her mouth, I realized I had made a grave mistake. Her molars were like jagged icebergs destined to sink my Titanic. SOS. God. Make it stop. She felt me jerk back in pain, and stopped seconds later. I firmly grasped her arm, and threw her over the kitchen table. She obviously was prepared for a warm dicking as she wasn’t wearing panties under her yoga pants. This is the moment I had been waiting my whole life for! I grip my dick, and go to stick it in. Nope… nope… wait…miss… try again… OUCH! And at this point I made up some bullshit excuse so that she wouldn’t know I’m a virgin, “oh damn I’m kinda drunk”. Luckily she was a horny little slut and found the whole for me.
With each successive thrust, I remember thinking “damn my hand is tighter than this” before quickly having to reach down and try to find the hole again. It was an endless game, but right before strike 3 she threw the curve ball. Right. In. The. Pooper.
There are a few things in my life I vowed to never do… anal, meth, and heroine. I had unwillingly broken through the gateway into a much more euphoric high. Yet, I had an eerie feeling I wasn’t the first to venture into this barren wasteland. Oh no, I may have been a pioneer, but I was the first of many to come. I was paving the way for the international highway system. Before I could finish my though, I quickly pulled out and spilled my load all over the kitchen floor. I casually wiped it up with my suck before suggesting that we move over to the couch. Who would have thought that I was too out of shape for sex?
Miraculously my cock was still hard. Call it beginners luck? Before I could stop her she began sucking me off again. I thought for a moment I was going to die. I thought of every attractive girl I could possibly imagine as she ground away at my cock with her diamond sharp teeth. After feverishly trying to maintain my boner for a good 30 seconds, I was right back in the saddle trying all kinds of new positions. A good 40 minutes had passed, she was moaning hard, but quickly bucked me off. I guess I had hurt her? Oooops.
I asked if I had hurt her, and went to touch her and she freaked the fuck out and slapped me. Then she asked why I hadn’t gotten off yet. I guess that’s something I’m supposed to disclose? I told her that I did, and she started freaking out. I imagined the next 18 years of my life in hell. She tried to kiss me, I swerved, she slapped me again. God damn, this wasn’t what I had expected but little did I know that it would only get worse.
I had sex with Tammy one time a week afterwards, we were both blackout drunk and neither one of us really remembers. I guess I would prefer not to remember as she was allegedly high on meth? Damn. I called it.
The next girl I had sex with was in January of 2015. She had pseudo raped me in the streets of a small town after a bomb ass new years party. My friends all urged me to stay away, but two rapey kind of girls within a year? No way I was taking this for granted. She was overall a 4, had red fiery hair, and breath that smelled of rotten cucumbers. Sure, one could argue that my standards were incredibly low, but beggars can’t be choosers. I wanted nothing more than a high quality blowjob her exboyfriend had told me about. I took her back to my friends house, and I guess the liquor really did her justice because rumor has it I fucked her in the bath tub and almost drowned myself after passing out. Luckily, I didn’t have to worry about catching anything from this soon to be slut master as I was only her second guy (yay me). The next time I ran into her was on complete accident after my stoner friend invited me to his girlfriend house to drink. One turned into 13, and low and behold fire crotch showed up and I evidently took her to a random bedroom before defiling some 14 year old’s blankets. I guess it looks like Elmer’s glue when it dries? Needless to say I hated my life at this point.
A few weeks later, I ran into fire crotch again. Cock blocking is one of her finest skills and had no hesitation for attempting to make out with me in public. And of course, drunk me couldn’t resist. My friends decided to be dicks that night and leave me to drive her home… (again I don’t encourage drunk driving). My parents were a little hot about finding out about the party at my dad’s still, so I couldn’t go back to my house, and I couldn’t drop her off at my house. We ended up breaking into a random healthy’s that my friend worked at and went to the back couch to sleep.
Sure enough, she begins trying to fuck me as soon as we get through the door. At this point I’d already hit it twice, and I wasn’t about to miss the opportunity to have sex in such an off place. I took her to the back room and we had at it until the sun came up. I slept off my buzz, doctored the rug burn on me knees, and drove her home. Once again, I hated life. I had sex with her on two more occasions after that. Once at her house, after my friends ditched me there after a party, and again at my dads house after she snuck in unannounced after I got home from a party. That’s when I realized this bitch was crazy. I made for the fucking hills and never looked back. Afterwards she had a mental breakdown and went on a fucking spree with at least 10 random dudes.
A few weeks have passed by this point. I’m just returning from my senior trip to Myrtle Beach when I catch wind of a bomb ass party. I pregame, show up, and immediately I’m greeted by a short brunette who asks me for my phone number. I party the night away and decide to text her in the morning. She seems super into me, which is nice, because I definitely needed to get laid to cleanse myself of such a terrible history.
I go to a party where I see her again. She’s super drunk, and so am I. She arranges to come back to my mother’s house and stay because by this point having drunks over really wasn’t a big deal. She sleeps in my bed with me, but I am too tired to have sex so I go to sleep.
My mother walks in that morning and sees her sleeping next to me. She freaks out and the only response I have is that she’s my “girlfriend”. It didn’t fly at first, but I reminded her it could have been a dude in which case I would be just luck my gay stepbrother. Luckily for my mom’s sake I love pussy… God damn that sounds awkward now that I think about it. Oh well, no edits.
So I let this girl pretend to be my girlfriend the following morning while I get hit with laughing gas and have 4 wisdom teeth removed. Even on the laughing gas, I start to realize my drunk goggles had deceived me. She bore the appearance of a naked mole rat with a fake mustache super glued to its face, but she was nice and took care of me throughout the week while I was doped up, so it wasn’t so bad. I had to keep her around for a while so my mom wouldn’t think I’m bringing home prostitutes. This was probably the worst of my ideas.
The money hungry mutt drained me for around $1000 of my bank account, and was begging me to have sex with her. I finally caved one night, and began to “do the deed” before she puked into my sink and I was forced to clean it out with my hands and go to sleep with blue balls. Worst night of my life.
To follow up this once in a lifetime event, I caught her sexting random guys, and she even managed to cheat on me, despite taking month long residence in my bedroom. I broke up with her, yet she still managed to find a way to crawl back into my life. (On a side note, this was my second “serious relationship” if you can even call it that).
One day, she came crying to me at steak n shake about how she tried to kill herself because she realized how bad she fucked up with me. Sadly I took the sob story hook line and sinker, and shortly after I was in Dante’s 9th Circle. The following week she freaked out in public about how I never have sex with her, and I ended up giving it to her one last time. I was slightly buzzed, maybe a beer or two in when it began. Surprisingly, it was pretty much over before it began. 30 seconds flat! A new record. At that point, I was so disappointed with myself that I quickly redressed and went back to bed. I vowed to never have sex sober every again. Not to my surprise, the cold hearted bitch cheated on me with my soon to be roomate 2 weeks later.
After all of this, I attended Ohio University, one of the top party schools in the nation. Surly I could leave my awful history in my hometown, but it followed me. As I began to settle in at college, reality settled in. My roomate was questionably gay, and happened to invite over a freakishly large woman that I accidently matched with on Tinder.
On the night he brought her over, I was passed out drunk. The girl, who I will refer to as Bertha, had unzipped my pants and began to give me what I like to call a “Louisiana Blowjobs”. What’s that you might ask? Well, right before I came she pointed my dick at me and I splurged all over my god damn face. Surprise! I promptly kicked her out and went into a state of depression until mid November.
So, people may ask me why I hate sex. I think I have every reason in the world to hate it. I’ve experienced it and it’s not my cup of tea so to speak. I would rather live a life of celibacy than live my life in disgust from sluts and wildebeests. I have too much respect for myself. You may be asking, “but OP, what about the girls that aren’t ugly. Surly you would enjoy sex with someone attractive.” I have thought this over many times through, and I have realized that this would bring forth a whole new batch of problems. See, after I had sex whilst semi-sober, my ego was killed which will result in my performance being even worse. This is simply unacceptable. Drunk sex is out of the question when I’m with someone attractive. When it comes to people who I care about, I hate for them to not be happy. That’s my biggest fear next to heights, and holding other people’s babies. Nothing can make me feel worse than that, and so I simply avoid it. To put this into a metaphor… There comes a certain humbleness with the ability to give anyone, especially the ones you care about, a free popsicle, yet refusing to do so. Even though it could be their favorite popsicle, you don’t want to see the disappointed look on their face should it happen to melt.
I hope you all have enjoyed my random collection of sexual experiences. I look forward to reading the hate comments. Keep it weird.
Source: reddit.com/r/sexystories/comments/42qma4/mf_antitranscendental_sex_chronicles