I literally cannot buy things for myself

Does anyone else go through this or am I going insane?? Like today I found out that a game called Stage Tour, which is basically like a new Guitar Hero game, is coming out soon, and with that comes a bunch of new peripherals for the game, including a drum kit. I've been wanting to learn how to play the drums for a long time now, and I've also had a big interest in guitar hero in general ever since I was young, so it's like the best of both worlds in terms of me being able to have fun and learn the drums at the same time without either a) making my room impossible to walk around in and/or b) getting 500000 noise complaints from my neighbors.

In total the drum kit + the cymbals and an extra kick pedal (just in case a bitch wants to hit some double bass parts,,,,) would be around 280 dollars, and I would end  up getting it sometime during December, which is rlly cool!! However, again, it's 280 dollars. And here my spending anxiety kicks in...

For a long ass time I've been honestly rlly bad with moneySSJSJSJS,, a few years ago the only money that I would get were from birthday gifts from family and the money that i would get from Student Aid, which I would pretty quickly spend on food at uni, personal stuff and hobbies. Add to that the estrogen for my gender transition and like the weekly 20$ I would spend on therapy and I barely had any money for anything, sometimes having to resort to asking my mom for a weekly allowance to cover food and my discrete gender transition. To say that it was ROUGH would be an understatement. 

Now tho, I have a job that pays me enough to spend on stuff that I like and through my friends I realized that I should consistently save up money both as a backup in case anything happens and to like, pay for big things in the future (Like a few months ago my partner and I paid for a weekend long vacay in New York which I still can't believe we did LMAO). This is gonna sounds rlly cringe but for a while it was kinda nice to save up money and leave a small part of my paycheck torwards it, it was like I was working torwards smth greater which is nice. Now tho it's like,,, I don't wanna spend anything anymore, ESPECIALLY if it's for myself. All my friends say I should treat myself and get stuff that I like, but anything that I wanna get has to be super budget friendly, otherwise I feel like im wasting money on shit that I don't need and I won't have it available in case of an emergency or for my neccesities. It's reached the point where I can't even get new clothes for myself anymore or go to shopping malls and buy tons of stuff with friends. The only things I'm able to get for myself guilt-free at this point are like, DVDs patches and used books, because they're less than 15$ dollars for the most part. And it all kinda comes back to the Drum Kit. Like it would be awesome to get it, but my brain imediately jumps to "What if u get kicked out of the house?? Or how r u gonna pay for ur estrogen next week"? Even tho I have the money saved for it. And in the end I just end up overthinking my potential purchase for days until I eventually give up and don't buy anything. 

It feels like I'm featured on that one TLC (i think?) show about extreme cheapskates, and it's fucking me up rlly badLMAO. I wanna be able to spend money on fun hobbeys and do whatever the fuck guilt free, but everytime I try i like guilt myself into hating it before the thing I bought even gets hereeee :'( If anyone has any advice on how to work on this plssss let me know because I wanna be whimsy again...