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Carl will explain some of the basics of Caligula Casino and its security detail to Woozie, when one of Woozie's henchmen (Guppy I believe) walks in - having seen the plans, that brings up the "Gang" to three so far.
He has brought Carl a gift from Zero - a Card Reader. The only problem is, getting a card to read - and that's where this mission will begin. Grab a ride and head out to Caligula Casino down the block.
The Croupier will leave the casino, enter her car, and drive off. Your job is to tail her. Again, the Spook-O-Meter will fill up if you're too close, and will empty if you quickly back off. Tail her in the "sweet spot" - not so close that she spooks, but not so far away that you lose sight of her - either of those cases will cause you to fail the mission.
Be warned your target WILL be stopping for Red Lights - so if there's traffic up ahead, be sure to slam on the brakes in time! The good news is, the light patterns seem to be fixed for this mission, so even if you fail it, the same Red Light pattern should apply.
Eventually the Croupier will head into a Sex Shop - go in after her. Be warned, she pulls a U-Turn here - if you're too close you'll spook her when she spins around!
Once inside, find the red marker and step inside it for a short cut-scene, then grab the Gimp Clothes in the open doorway. Remember... a little pain now, a LOT of payoff later, right?
The Croupier will then leave the shop, hop back into her car, and take off again. Chances are whatever vehicle you parked outside is gone - there should be a car nearby to jack. Quickly get one and hit her trail before it gets cold! Be careful of lights along this little stretch - there's lots of em.
Eventually she will hang a right into a residential area, then a left. Be VERY wary here - there is a bump up ahead on the train tracks, there's a red light ahead, and you'll probably slam into the Croupier, completely spooking her and failing the mission. Let off the gas here - or all you get out of this mission is to be someone's Sugar Daddy.
Another left and from here the Croupier will walk into her house. The tailing portion is over; your job now is to make sure her usual gimp doesn't make it inside - you want to take his place.
He'll be VERY incognito - walk up to the house and look for a guy on the left without a shirt on, wielding a dildo. Kill him in any way you please, take the Dildo if you want, then walk up and ring the doorbell.
Doing this "completes" the mission - but you don't have the card yet. Oh no, you got yourself another girlfriend, Millie - and you'll need to "wine and dine her before she will give you the keycard" as the game puts it. So... get on it. She should be available at her house starting at 12:00.
To woo her, drive around her general area. When you've successfully got her loving you enough, she'll call you on your cell phone and agree to your scheme. Walk into her house while she's not home and get the card to totally complete this mission.
- Clothing: Gimp Suit.
- New Girlfriend: Millie Perkins.
- Keycard required for Caligula Casino heist once Millie loves you enough (35% Progress).