This will probably be a TL;DR, so I have provided cliffs at the bottom.
Back when I was 16 or 17 I met a guy online who played poker professionally and he agreed to coach me which never ended up happening, however I did end up getting my brother to make an account on an online gambling site so that I could grind poker. I deposited about $300 which was almost all the money I had at the time and I didn't have a job or anything so I really didn't have anyway to get more if I busted.
I started out playing $0.02/$0.05 and of course after awhile I thought I was crushing the games so I moved up stakes. I was obviously a total donk at the time so I couldn't really beat anything. After awhile I played higher than I should have and would lose like $50 or $60 in a session so I would then play BlackJack to get my money back, which only lasted so long until I went busto.
My grandmother lived with my family at the time (She has since died) and she would let me use her credit card for online purchases since I didn't have access to anything else at the time, so whenever I had money or thought I had money coming I would deposit another $20 or $30 and lose it all of course.
Note:she never actually knew I was using it to fund my gambling. Also, at the time they had a casino promotion going on that was actually +EV and I could get about $20 a week from it, but I would usually gamble all my money and have to deposit more so I would have enough money to do the promotion, always resolving to leave enough in the account to not have to deposit again.
So it wasn't really that degen, but I gambled pretty much all the money I had at the time.
Fast forward a little bit and I started getting more money through various sources and I also put a lot more study into the game so I was actually turning a reasonable profit at $25nl and because I was making a couple hundred each month I decided to buy a horse. I needed to buy hay for it, but I had money in my account that I was going to use for it so I thought I was fine.
I don't remember how much I had in my account at the time, but it was somewhere around $700-$800 and I needed about $500 for hay. Also keep in mind poker was my only source of income.
I don't remember why I didn't cash out the money immediately, but I didn't for some reason and obviously I kept playing poker.
I also don't remember all the details of what happened, but I basically had a bad session and got tilted and blew it all on casino games trying to chase my poker losses. I don't remember if I deposited more, or if I left a few dollars or what, but I ended up having about $10 left in the account.
After I lost all that money I was pretty sick because I had no idea how I was going to get money to buy hay. My mom was pretty much broke at the time and I really didn't want to have to ask my dad for money since I obviously should have had the money for hay before I bought the horse.
The next day when I got up in the morning I decided I would enter two $5 tournaments and try to grind it back. I busted out of the one after an hour or two and then ended up shipping the other one for around $140 or so. I was obviously pretty stoked after that and went on to win a few more tournaments after that and was able to cash out all the money I needed for hay.
I was feeling pretty good about things after that and kept grinding poker. I started to play higher stakes and got my roll up to about $6000 and I didn't really have any expenses at the time so this was all just free money for me and was probably more than I had ever had all the rest of my life combined.
I was about to turn 18 at the time so I was planning to use it to get some kind of business going or something.
I decided to start cashing out a couple thousand each month so the first month I cashed out $1000 then the next I cashed out $3000 and by that point after I had cashed that out I was sitting with about $6000 in my account.
I should also note that I was still playing casino games and at this point I was starting to bet a lot more on my gambling binges. I kept trying to stop and at one point I got really tilted after losing a few hundred playing roulette and I put $100 on the second row and $100 on 35 which was a pretty big bet for me at the time. I had gone up to $500 BlackJack bets awhile back and busted the account, but I think I only lost about $1000. Anyway, the 35 hit and I really couldn't believe that I had just won $3700, which put me ahead for my lifetime gambling. So I pretty much swore off gambling at this point which unfortunately only lasted for a couple days.
I also won a $2000 Jackpot in there somewhere.
After that I then started gambling in the casino and basically stopped playing poker.
I would usually just start with about $100 of chips and just do small bets "for fun" but would then get tilted about my losses and buy more chips until I got back to even or got ahead.
The last day I did any serious gambling I started small like normal, but then got to the point where I was betting the max on roulette which was $500 inside and $500 outside. And betting max on BlackJack which was $500 a hand. I don't remember entirely how it went, but at one point I was down to about $2000 from starting at $6000 and I was like starting to get all sweaty and panicky and felt kind of like I had a caffeine buzz or something. It got to the point where I was like pleading that I could get back to even and then I would never gamble again. Amazingly I ended up having one of my big numbers on roulette come through and I got up to even with about a $300 profit. At that point I was like. Whew, Thank you God. But I couldn't bring myself to stop so I told myself I would just do small bets with the extra $300 "for fun" since it was extra money anyway.
Long story short I kept gambling and went way down.
At one point I was playing two hands of BlackJack at $500 a hand and got a 9 and a 10. Of course I had to double them for the rest of my money, but I got two low numbers, however, to my surprise and great relief the dealer actually busted.
So now I was up to $4000, so I went to roulette and started losing a bunch or money on there. It got to the point where I was betting the max which was $100 on five numbers.
I couldn't get anything going to and after a little bit I was completely busto.
After that I felt a strange sense of relief that it was all over.
I just sat there staring at my computer and after a minute I got the urge to punch myself in the head, so I walloped myself a couple times and then went outside and wandered around for a little bit.
I don't remember completely, but I may have moaned a little too.
I felt pretty depressed for the rest of the day.
It's kind of weird, but I felt like a sense of both relief and deep regret at the same time.
After that I gave up poker/gambling.
Now I can look back and say that in some ways I'm glad this happened to me then before I got a job and got married and stuff because it really didn't do to much damage to me at the time.
I have also since then become a winning poker play and am happy to say I never touched casino games after that, although it has been a struggle at times.
I am actually pretty ashamed of what happened and have never told the entire story to anyone and have only mentioned it to one or two people.
Hopefully some of you can get a little bit of enjoyment out of this and my advice would be that if you don't have much self control, never get into gambling.
Cliffs:
Got my brother to make an account on a gambling site and gambled all of my limited amount of money on poker/casino games.
Went busto numerous times and redeposited using my grandmothers credit card.
Got a horse and gambled all the money I needed to use to buy hay for it, but then got lucky and won a tournament with my remaining $10 and ground that up to $500 in a week which I then used for hay.
Got good at poker and started to win decent money at $25nl then started playing casino games a bunch and stopped playing poker so I could gamble more.
Won a Jackpot for $2000
Put $100 on 35 and won $3500
Lost it all during a big gambling spree
Gave up poker/gambling
Grew up a little and got back into poker and became a winning player, but stayed away from casino games all of this time.