Now that we've helped out Lemma and Erin and our Timber score is high enough, it's time for some hot sexy fun time!
So we need the Shroud of Urine to get the guitar, we need the Poolaroid camera to get the Shroud of Urine, and we need the Sleaze Wars figurine to get the Poolaroid camera. But how do we get the Sleaze Wars figurine when we don't have a way to make an easy thousand?
If you've talked to Waltraud at the pawn shop, she will mention that the sealed Sleaze Wars figurine is full of 1970s air. This is your only (vague?) clue that you're suppose to take the air out, exposing the figurine to the elements and forcing it to drop in price. To pop it, you have to throw a dart at it. Waltraud won't notice what you're doing, but she will notice the opening in the sealed packaging and will be forced to drop the price to a dollar. From here, you can use the dollar you've found in the bathroom at Lefty's Bar to buy the figurine. You know what to do from here: head to Prune Headquarters and give Kyle and Finley the figurine so you can take the Poolaroid, give the Poolaroid to Everett and Atticus at Salon du Lezard to take the Shroud of Urine, give the Shroud to Cébé for the guitar, and finally hand the guitar off to Lemma.
Interestingly, someone has broken out of the jail by the time you come back to Hell's Pawn with the Shroud of Urine.
When you hand the guitar off to Lemma, she will tell you she needs one more thing to make sure her show really rocks: artificial smoke. Thankfully, you've got the e-cigarette from Smokey Bear. If not, go get it. You'll get a Instacrap cutscene of Lemma in concert as well as the highest score on Timber from Lemma, then she'll invite you to Hell's Pawn for the afterparty. You'll also get an achievement ("Lemma").
At this point, you'll have 26 points - enough to enter Hell's Pawn - then you'll get a cutscene at the skyloft of Prune Headquarters where BJ and Faith notice that Larry is doing well on Timber and try to make sure he never gets near the new PiPhone again, as he confused the new AI. You'll also get new suggestions on Timber.
Now that you have the necessary amount of points, you can now enter Hell's Pawn. You'll meet Dick Ryder here, but you'll also meet someone else: Anu Singh. Go through the dialogue options, and you'll notice that she is waiting on BJ for some reason.
Lemma will be at the VIP entrance, but you'll need a ticket to the VIP area to follow her in. To the right is Becky and Lance. Talk with Lance, and go through the dialogue options. When you tell him about Dick, Lance is surprised that he is here. Becky seems more concerned about herself, and when you mention that you and Dick are heading to the darkroom, Lance admits he went out on a date with Becky just to make Dick think he was doing okay without him. Becky decides to look for another guy, and ditches the ticket to the VIP room on the table. At this point, it becomes apparent to Larry that Lance is gay.
Take the VIP ticket off the table, then use it on the ticket scanner near the fire gate. You'll go down into the dark room. Save your game in a separate slot once you go down here, as you'll be getting several achievements and Instacrap videos from this part of the game.
Talk to Lemma. It doesn't matter which options you choose, as the results will be the same. From here, click on the chainmail bra on the demon statue near the darkroom entrance. Pi will give Larry information on how to remove a bra via telekinesis, and Larry will be able to take it and put it in the inventory.
From here, talk to Erin. Go through the dialogue options, and when Erin mentions that she barely knows anybody in the nightclub when asked about going to the darkroom, tell her you would like to introduce her to Lemma. Erin says she would like to get to know her a little more personally.
When Erin and Lemma finally meet, pick the "..." option when it is Larry's turn to speak. Erin and Lemma will continue talking, and you'll get an achievement for it ("Bechdel Test Passed"). Afterwards, you'll be able to join them in the darkroom. If you haven't saved in a separate slot yet, do it now.
Once you're in the darkroom, hold the Space Bar to figure out where you can click to interact with things. There will be only two things to interact with: "Moist Hole" and "Floppy Mass." Poke around inside with the floppy mass before "sticking little Larry in it," then stick Larry's tongue and finger in the moist hole. Call something into it once you've done both, then you'll hear everyone else.
There will be three things to click on at this point: "Heaving Mass of Flesh," "Strangely Smelling Object," and "Hairy Thing." Interact with them all. You'll hear everyone else.
There are some new things to interact with: "Membrane Opening" (which you'll want to stick your head in) and "Seething Pool" (which you'll want to stick your whole foot in). There is also a "Strangely Familiar Silhoutte," and if you interact with it, you'll meet Lefty outside of his bar. It turns out he is here to find fresh ingredients for his brewing experiments. You'll also get an achievement for this ("Lefty's Dark Secret").
From here, you'll hear Lemma, Erin and Dick. If you pick "Lemma and Erin?," you'll get the "Going For The Girls" achievement. If you go for "Dick?," you'll get the "I Prefer Dick" achievement. Regardless of who you choose, the police will show up and arrest Larry after making a reference to Larry Lovage (Larry's nephew from Magna Cum Laude and Box Office Bust). There are two very similar Instacrap videos here, and the one you get depends on who you pick, with the only difference being what Larry does at the end of the video.
You'll end up in jail, with Anu Singh being outside of the cell. She is your public defender, and when Larry asks what he is being charged with, answer with "It was dark and I was drinking!" every single time. (This is the last option on every dialogue option.) You'll get an achievement for it ("Dark And Drunk!"). Anu will leave, and you'll meet a drag queen named Tuck. By going through the dialogue option, you'll find out that your PiPhone is on the safe and is yet to be processed, but you won't be able to reach it. Your entire inventory will also be gone, and the notebook will be back on the lower-right corner of the screen.
Click on the light beam, and you'll be able to look outside of the prison. There will be a whistle on the ground. Take it. Back in the cell, take the plunger next to the vanity mirror, the string of lights and the perfume bottle on the shelf. Tuck will let you have the perfume.
There is an ink pad on the desk near the cell walls, but you won't be able to do anything with it...yet. You also won't be able to do anything with the Lady Gag poster (a reference to Lady Gaga, obviously).
From here, ask Tuck how to get out. You'll find out that Tuck lives here on their own accord, and that he really wants a cavity search from the officer in the jail. The officer will open up the peephole on the door and tell Larry and Tuck to shut up or else he will go in there, and Tuck gets the idea of doing something really loud that will make him angry. Use the whistle you just found on the door, and Larry will use the whistle. Tell the officer that Tuck insists on a cavity search, and the officer will refuse and walk away. From here, talk to Tuck and choose "Then I'll search you." Tuck and Larry will do their thing off-camera while the officer is weirded out, then the camera will be back on Larry. You'll hae a new item: a cucumber. Combine the cucumber, the string of lights and the plunger and use it on the PiPhone on the safe, and Pi will call Dick Ryder. Regardless of which option you choose from here, Dick will bail you out.
Outside of the jail, Dick will apologize for not being over Lance, but Larry will be cool about it regardless of which dialogue option you choose. Afterwards, Dick will update your Timber profile picture before telling you that Lance is the guy for him, even though Lance has been trying to avoid him. Larry says he will help if Dick gives him the highest score on Timber, which Dick agrees to.
Dick mentions that Lance has a problem with publicly acknowledging his sexuality and their relationship, feeling it would put him at a disadvantage and make people think less of him, and asks Larry to help Lance open up. You'll get new suggestions of Timber, then you'll be able to explore New Lost Wages again...after finding out that your inventory has changed. You will now have a Gym Customer Card in your inventory, allowing you to go further into the gym on the New Lost Wages strip.
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