Reddit, what is your best teenage fuck-up story?

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61

I was a pretty serious kid. I loved working out, didn’t drink, played several team sports in high school and was kind of a dick overall. I didn’t socialize much outside my friend group.

Anyways, being an aesthetic sonofabitch, one girl eventually took an interest.

I had never drank, but she invited me to drink with her friend (a girl) and her boyfriend (my close friend). So… we invariably got shittered, all 4 of us. But me, being a complete newbie, got very affectionate with said girl - not that that was particularly a problem for anyone, as the other couple was also goin at it pretty hard.

Anyways, the night carries on, and our drinking transitions from a bar into a park near my friends house. With a bottle of vodka between the 4 f us we are all on another planet at this point.

My friend and his girlfriend go around the corner to a secluded part of the park and have sex explicitly, which is fine with everyone. But now my girl is getting rowdy and starts giving me a handie in the park. Anyway, friend comes back and puts his girl in a cab and offers me and my girl a place to “crash”.

Somehow we all end up in his bedroom sleeping (I was pretty drunk). I wake up to my dick being sucked by said girl I was hanging out with. Proceeded to bend her over and pound her silly - as my friend was “sleeping”.

Next day when we all woke up was awkward for her and heroic for me.

Here’s the kicker - his mother is the one that found the jizz on his wall the next evening when they returned from their trip. Friend had to clean it up.

Sorry bro.

62

First date with a new girl. She was 14, I was 15. Before the date we were chatting on MSN Messenger and the chat got a little “naughty”. For some reason I thought it would be cool to say I fapped over her the night before. She giggled and made the “blushing” emoticon. It seemed to go down well… We met up and went to the park to fool around. She then gets a passive aggressive call from her mother and was told to meet her at the parks entrance. Jumped in the car all innocent-like and got the death stare of the century! “Do you think it’s right to masturbate over our daughter?” “How old are you?” “Why do you talk filth to our daughter?” I was then confronted by her father and after a long “chat” I decided the only thing to do was burst into tears on her mothers shoulder. Seemed to do the trick as she made me dinner…

Turns out the PC she was using was her Father’s laptop and instead of shutting it down she put it to sleep with all the chat windows open. Her Father read all our naughty messages.

TL:DR - I fapped over a girl, told her and then cried on her mothers shoulder resulting in me getting dinner.

63

I was probably 13 or 14 when this happened, but one time my friends and I were walking down the sidewalk and out of nowhere my friend just softball pitches a honeydew melon right into the side of a passing cop car, I forget why he even had the melon in the first place. Anyways the melon explodes on the passenger side door of the car and leaves a huge dent in the door. We all take off running and the cop flips the most ridiculous u-turn I’ve ever seen across three lanes of traffic and takes off after us. Luckily, we were right next to my friends moms apartment complex so we ran to his place told his mom not to answer the door for anyone, shut all the blinds and hid in his room. After 10 min we saw three different cop cars drive past his apt., then 5 minutes later we heard a helicopter and peaked out the window just in time for the spot light to catch his window. Few moments later, a knock on the door, my friends mom answers and tells the cops that she’s the only one in the house and hasn’t left all day. They bought it, but it took another 45 min for all the cops to leave the complex and another 30 min for us to build up enough courage to leave his room. His mom was pissed but also thought it was hilarious.

64

Okay, so I was a pretty sheltered child. This is 8th grade One day me and my best friend decide to hang with the popular kids. We go into the woods and decide we want a little fire cus were bored and its a summer day. The two dudes leading the fire fight over whether or not to make a pit, then the more idiotic dude lights a pile of leaves. It starts to get big. Lacking the safety pit he panicks. He grabs a huge bed of moss and tosses it on top. That, was a bad idea. The moss begins to smoke, it all lights up. My buddies start trying to stomp it out with their boots. No success. Me and my friend run to the local corner store to get jugs of water. We come back and start pouring, we see the dudes run over “its too big its too big we gotta go”. We run to the local park, we look in the direction of the woods and guess what we see. A big ass smoke cloud.

TL;DR first time hanging with now best friends, start forest fire.

65

I wrecked my father’s company vehicle when I was twelve. He was with me…

66

When I was about 14 I went to a party and got shitfaced. Since I wasn’t able to walk home, some of my friends carried me. When they arrived at my house (with me on their backs), they realized they didn’t want to get in to trouble with my mom, letting me get this wasted ect. So they decided to leave me outside in front of the door, ring the bell, and leave the crimescene.

After my mom found me, she carried me inside, took off my clothes and sat me in the shower. She then proceeded to shower me like I was some kind of toddler, while I was desperatly sobbing, trying to get her away. Covered in vomit.

The following day I woke up in my bed, naked and clean. Not clearly remembering what happened the night before, I walked out in the livingroom and sat on the couch praising the lord that the hardship finally was over. My mom then turned off the TV, looked me dead in the eye and said: “Sweetie, are you having intercourse since you shave your private area? Also, you have hickeys on your breasts. Cover them up, we are going to grandma’s”.

And that’s the story of me not looking my mother in the eye ever again.

67

My mom took me to a baseball card show when I was fourteen. As she waited in the hotel lobby, I bought myself some forbidden fruit: the infamous 1989 Fleer Billy Ripken card.

On the drive home, I begged her to give me a driving lesson. She hesitated at first, since we were in my dad’s company car but I eventually wore her down and we headed for the backroads.

I took to driving like an American Idol hopeful takes to melisma. Forget the 10 and 2 position, I got cocky and trilled “Look ma, no hands!”. Bad idea. Car Wheels on a Gravel Road? Not anymore. I flipped the car into the ditch and felt exactly like that dirty word written on the knob of Billy Ripken’s baseball bat.

68

My “friend” wanted some weed so I sold him some for a cheap price. He then brings it to school the next day, gets caught with it, then tells the school I was the one that sold it to him. I got in more trouble than I ever have been that day.

69

On a rainy day, a couple of friends and I were sitting on the top row of our gym. Jokingly, my friend said I will give you 5$ to throw this apple at our VP at the time.
After a min of thought I was all in, but not until I pulled some more money out of my “new friends” who started to mingle as they overheard my mission. The pot has reached 50$ and by now there was no backing out, I grabbed the apple reared back and let lose, now mind you I was starting catcher on my varsity baseball team and was darn near 80% throw out rate so I was accuatly lethal with my right arm, as I gripped the apple I realized it felt just like a baseball. I saw female VP start walking toward a trash can, alas I had an out if they question me about throwing the apple at her I would just say I was throwing it at trash can. After I released the apple it flew threw the rafters, and was headed directly towards my target 75-90 feet away, it hit the VP in the neck shoulder area she dropped like she has been shot by a sniper. A hush came over the gym, you could literally hear a pin drop, my friends began to assemble in small groups leaving me as the only person sitting by themself.
One student pointed me out to campus police and I was arrested for assault with dangerous weapon and put in Juvenile hall for the weekend.
I was a So in HS at the time and never played varsity baseball because of this incident. Still the best story at all of the reunions, and that was 26 years ago.

70

Not me but a friend of mine.
He came home after a heavvy night of drinking.
The next morning his dad woke him to ask wtf he did last night and asked him to follow him to the living room,
Where he got confronted with a turd on the sofa.
Basically he shat on the couch then went to bed

71

So I am still a teenager and just hit drinking age last year:

  1. Shot silvester rockets into a dustbin. Cought fire. I felt bad and was the only one to put the fire off ( there was a barrel with gritting material nearby)

  2. Decided to meet a girl who I really loved. Friends told me to “drink alcohol” to make the interaction way easier. She is absolutely anti-alcohol. I drunk way too much alcohol, which resulted in me being drunk as hell. She started ignoring me afterwards.

I stopped drinking alcohol.

72

Am I the only father of young children reading these and thinking, OMG, what have I got myself into?

Every single story, I can’t help but place one of my two children into it and thinking what would my response be?

73

Well here it goes…

Summer of grade 10 I made my first travel soccer team. I’m pretty cocky about it so I’m always wearing my team jacket and shirt around school. I went as far as to get a full DBecks mohawk with frosted tips, for good measure I added some racing stripes down the side. Anyways, we come back from an way trip after loosing a pair of games I’m in a crummy mood but luckily it’s my friends birthday that night.

For her birthday her friends arranged for her to do a ‘car rally’. Pretty much theres a list of tasks and you and a group of others have to complete them and document them with a camera (theres usually tons of alcohol involved)

I’m 16 at the time and none wanted to DD so my group decides to go on foot. Also… I totally got the short end of the stick and my group is made up of a larger girl (who I found out later liked me and insisted that we be paired together), another buddy and another girl I did’t really know. Anyways we end up going down to the beach and start completing the tasks, I should also note that my groups theme was pirate, so I look like a jersey shore pirate with my awful haircut. I figure the only way i can have fun is if I get absolutely black out drunk. Well a pint of vodka later I’m laughing, totally blasted and its only like 8pm, people and their families are still out enjoying the beach. The large girl pulls me into the public bathroom a the beach and we start making out, eventually a security guard comes in and kick us out. I notice my friend and the other girl are gone (hooking up at the time) so me and the big girls walk towards the party house.

On the way we stop at starbucks to use the bathroom, I’m still wasted drunk and sneak in with her… Well two drunk teens walking into a bathroom is pretty obvious from what I’m told, a few people knocked on the door and we ignored them. Eventually the manager starts opening it with the key, I’m just zipping up my pants as he walks in, he says he will give us 5 mins before he calls the cops. Luckily a cab drives by and we hope in and go back to the party.

I guess all my other friends knew that this girl had been planning on having me in her group the entire time, so I’m getting ripped apart when its only the two of us that show up. I decide to drink more, get my ear pierced with a home ear gun (for more points) and then go face first into the birthday cake which sparks a food fight (parents weren’t happy).

The rest that happens is what I’m told, I have no recollection. Apparently this girls brother (who I’ve known for a long time) invited me into his room and we take some bong tokes. He warns me about the broken bowl and I end up slicing open my thumb pretty bad, I bleed all over my shirt. At this point my friends decide to put me in a cab and I sneak home into bed.

I wake up to my mom yelling at me, I’m covered in my own puke, blood and piss and have an earring to go with my mega douche haircut… Anways my mom as punishment makes me keep the earring in for 2 weeks, to let the embarrassment factor stick before I’m forgiven.

TL;DR Get wasted, dress up as guido pirate, get caught getting bj in starbucks, green out, wake up in own fluids

74

My entire teen age decade was one big fuck up but this is probably the most movie scene worthy:

Freshman year friend and I had heard a rumor that you could get over the girl’s locker room through the guy’s if you climbed up through the ceiling tiles. Being the ambitious perverted boys we were we decided to find out for ourselves if this was true or not. So one day we didn’t dress out and sneaked back to our locker room and did in fact manage to get up into the ceiling by climbing onto a set of lockers and lifting a tile then pulling ourselves up.

As you might expect it was very cramped and dark up there and we didn’t have a flashlight but we came this far and weren’t backing down. So we’re making our way in the direction we think the girls are on this catwalk kind of thing but we come to a partition pretty soon. It seems whoever engineered our school building had considered perverted boys might try something like this eventually. The catwalk didn’t end here though it kind of went around and looked like we could follow it and then turn and keep going in the right direction.

Long story short this didn’t lead over the girl’s locker room but rather over the split office in between the two gender’s rooms where the gym teachers had their offices. We didn’t know this. What we did know was that we could hear a female voice and assumed we should be right on target. So we start to try to crack a tile and take a peak but my balance was off and I fell right fucking through that tile.

Now I fell pretty hard but miraculously wasn’t injured just bruised up a bit. I did however scare the shit out of the female teacher who was talking on the phone in the office. Even luckier there were no girls in the locker room anyways and this teacher was pretty friendly with my friend and I so she found the whole thing hilarious in the end. She told us had there been any girls she would have been forced to discipline us but since we were really just stupid perverted boys she’d let it slip this time.

TL;DR you can’t get to the girl’s locker room by climbing over the ceiling tile’s from the guy’s side.

75

Had to get bailed out of jail night before commencement

76

I told a girl I barely knew that I had a huge crush on her. Naturally it didn’t go well.

77

When I was 17 my dad and I went down to Mexico. I knew that he smoked weed, he knew I smoked weed. I thought this trip was the perfect time to smoke together. So I had to find some weed, it wasn’t easy but I did it. That night I had it with me, and we were on our way into a club when I realized the bouncers were searching everyone. So very stealthily I dropped the weed on the ground and then bent down to tuck it in my sock. Well… they saw me do this- swarmed me, yelling in Spanish I was going to the Federales. I was terrified. My Dad has no idea whats going on but eventually steps in and calmly asks “cuanto cuesta?” He hands the bouncer a hundred dollar bill and they let us in the club. His first words to me afterwards: “we’re not telling your mother”

78

It is such a cringey thing, what I did, and it still makes me feel stupid when I think about it.

I was 13 and was hanging out with a few other kids, and one of their friends had autism, I think, and I was talking to his mom while I was waiting for a crazy carpet or toboggan to find its way back to me. We were, as you could have guessed by now, tobogganing. She told me that he can pick up a video game and beat it in like 3 hours without taking a break because of his condition…and my response was: “Yeah, I can do that too. But for him that’s, you know, really good.”

That was so rude and stupid of me to say.

79

Me and my buddies from middle school were going to this abandoned house that’s somewhere in the desert and check it out. When we arrived we saw a side of the fence that was ripped and entered through there. As soon as we entered we saw 3 crosses that were burned and thought they must have been used for some kind of KKK meeting. We saw a backside of the house and then found a small ATV which we tried to push home but was too heavy. I found this small white fat tube on a tripod which kind of looked like a telescope and my other friend wanted to take it home, so then we took a risk of opening this one metal door which I thought was risky, and as soon as he opened it. he yelled " Shh" after about 3 seconds we heard this small beep, and as soon as we heard it we all thought it was an alarm so we ran as fast as we can out the fence and back into the desert and were so scared that we didn’t know what direction to take since there was a small town near the desert. I heard sirens so I just went running back where I came from and since my school was near the desert I tried to act like I was walking home but then I saw about 2 or 3 fire trucks. and then I waited which seemed like a long time and they were gone. The next day some cops questioned me at school and I was shaking alot and stuttered but never told them that it was me and they tried to say they have evidence, but I kept saying it wasn’t me. My parents never found out about what happened. This was actually one of the times I felt adrenaline and ran for a long time without stopping.

80

Probably too late to the party… But it’s worth a go.

I was 15 and got real baked with a buddy before going to the movie store. Inside working is another buddies little brother. He informed me that the store is selling all it’s VHS porn videos since they are moving to DVD. So I cut him a deal on almost all the porn they had. I was thinking I’d be able to sell these to people at school or whatever… Ya know, solid business opportunity!

I went through and picked out the good stuff (lesbians, milfs, etc.) and left the weird stuff (insanely big nipples, midgets, etc.) there. Anyways, I got a great deal. I think about $2 a video. So I probably had 30 videos in a big green backpack and I didn’t even know where I was going to hide this, but I put it back in my basement crawl space, thinking it was safe there until I could offload them quick. Well, it didn’t take long and my mom came across the whole bag of em. Apparently she spent the night thinking I was some major porn freak, while she smashed every video with a hammer…

They were relieved when I tossed the business angle at them… But still not impressed.