004 OG: おれ…「毛」が薄くて困ってるんだ TL: "I...I'm having trouble with my 'hair'" ED: he's talking about it being thin (directly related to next few lines)
005 OG: おれもシゲちゃんみたいに TL: "I'm just like you, Shige-chan!" ED: he wants to be like him
006 OG: 鷹楽がジャングルなんだってさ TL: "He said Takaraku is a juggler" ED: his name is Takara and he's saying his hair is like a jungle
OG: で TL: "Pfft" ED: so
007 OG: 教えたんだしシゲちゃんも教えてよ〜 TL: "I taught you, so you teach me too, Shige-chan" ED: told
OG: どういう風にいつもオナニーしてんの? TL: "How do you always pull off that streak?" ED: he's asking how he masturbates
008 OG: そこをなんとか! TL: "I'll take care of that!" ED: he's asking him to do anything
009 OG: い、一回だけだからな… TL: "No, it was one time..." ED: he's not denying anything, he just stutters when confirming that he's only gonna do it once
012 OG: すっぽりだな…まだ剥けてねーの? TL: "That's all there...still no interest?" ED: this line makes no sense, he's talking about the foreskin still covering his dick
OG: あとちん毛は生えてんのな TL: "And you've got a dick" ED: he's talking about his pubic hair
OG: ちゃんと剥けるよぅ TL: "So that you can peel it properly" ED: made up line, he's replying to the MTL mangled question
OG: 折角だしおれも横で抜いていい? TL: "Can I pull it out on the side, too?" ED: missing detail, he's saying he might as well