This was a really long joke I created in response to your post, "What the heck did i just see?" in response to Alih3434's post regarding a chain of images. It took me around 30 min just to research all of this to be sure I'm getting it right lol.
The 1st image is a screenshot of fictional Japanese idol Riamu Yumemi from THE iDOLM@STER series, who is known to be an otaku that has low self-esteem. The screenshot is of her preforming her solo recorded song, OTAHEN Anthem, which has lyrics referencing her personality and hobbies, in the image's case, the lyrics reference her low self-esteem.
The 2nd image appears to be fan art of a fictional demon by the name of Malina who appears in the recently released puzzle-adventure and dating sim, Helltaker. Malina is known to be "salty nostlagia gamer", playing old turned based strategies, and an alcoholic, further emphazing her cranky attitude.
The 3rd image is also fan art of Malina, with this one showing her down an entire bottle of vodka as a joke to her alcoholism.
The 4th image is fan art of characters Ami Aiba and Arata Sanada, both appearing in the RPG Digimon Story: Cyber Sleuth. The artist is possibly shipping the two characters, as at appears that Ami is teasing Arata for crossdressing, and is also appearing to be a dominant partner in perceived relationship.
The 5th image is fan art of, again, Arata Sanada, but shipped with the male protagonist counterpart of Ami Aiba, Takumi Aiba. The genre of this is known as yaoi, which is a Japanese media term referring to a male homosexual relationship.