You can encounter Ms. Woods on the Main Square while doing some people watching. You will spot her struggling with some bags after a shopping trip.
If you decide to help her out she will dump all her bags on you and expect you to carry all of them to her car. If your attitude is dominant you’ll just toss her bags in and she’ll throw you some change but if you’re more submissive and you’ll go as she asked she’ll give you her number if you want to accompany her on another shopping trip.
From this point on you’ll be able to call Ms. Woods.
If you decide to call her she’ll ask you out on a shopping date for the next day at noon.
On the date Ms. Woods will ask you to carry all of her bags for you while she goes on a shopping spree. The bags will start to pile up and your strength will determine how long you can last.
If you are on the weaker side you won’t be able to carry all of the items and Ms. Woods will get mad at you for being so weak. She’ll ask a security guard to help her out. You can decide to leave at this point, but if you stick around and follow the two of them to the garage you’ll be asked to thank the guard for helping you out. Once you do this Ms. Woods will be impressed enough by your determination to ask you if you’d like to be her sugar baby.
If you are somewhat stronger you’ll be able to carry every item she picks out and once she’s bored with shopping she’ll ask you to pick the last store: a boutique or a lingerie store. In both stores, Ms. Woods will pick out an item and head towards the changing room, but it’s not her who’ll try on the item. Once you tried on the pink lacy lingerie set or the cocktail dress she’ll come in the changing room after you and give you a reward for doing so good. She’ll buy the item and hand it to you. After you escort her to her car and pack everything in the trunk for her, she’ll ask you if you’d like to become her sugar baby.
If you decide to accept her proposal you’ll meet the next day and she’ll take you out to watch a play. She’ll pick you up, but she won’t walk in with you if you are not wearing elegant clothes.
Once inside, Ms. Woods will quickly get bored by the play.
If you’re smart enough you can explain the play to her, which will make her get in a better mood.
If you’re just as confused by the play as she is, you’ll spend the first part of the play in awkward silence.
Once the first act is over you’ll notice that other audience members got quite inspired by the play and Ms. Woods invites you to do something for her too. You can choose to please her with your fingers or with your mouth.
Before you could really get into it the second act starts and since you came to watch the play she’ll ask you to sit with her. Once in her grasp, she’ll play around with you before the play ends.
At the end of the date, you’ll take a taxi home, while someone picks her up and you’ll receive your envelope with your allowance inside.
If you managed to gain Ms. Woods’ favor for the next date she’ll invite you to her mansion just outside of Hornstown.
If you did something she didn’t like you’ll have to work a bit more to get the invitation. You can repeat both the shopping trip and the theater date once to get all the favor you need, where Ms. Woods will be much more forgiving of your possible shortcomings.
Once you get the invitation to her mansion you’ll need to take a taxi the next day to go and see her. She’ll greet you and she’ll proceed to show you around her mansion, where you’ll meet her assistant Jay.
After showing you the first floor and part of the garden Ms. Woods will invite you inside for dinner. If you’re smarter than most you can impress her with your knowledge of fine dining, if you’re lacking in this department Jay will help you out.
After the dinner, Ms. Woods will lead you to the lounge where you can ask her a few questions or you can just listen to what she has to say.
Either way, you are going to end up making out on the sofa, then she’ll invite you upstairs to spend the night with her.
On the way there you can decide if you want to also invite Jay to join the fun or if you’d rather spend the night with Ms. Woods alone.
After this, you can keep going on different dates with Ms. Woods to the places you visited before and the option to invite Jay along will present itself every time.
As long as you don’t wait too long between dates you can keep getting your allowance envelopes from Ms. Woods. Every 2-3 days seems like the best with her, but you can wait a bit longer if you find yourself too busy.