Over Again a Milking Story
This page takes you through Diane's storyline which will see you get to know Diane while working in her garden and helping her out.
On Day 1 Debbie will mention you could do a little work for Diane to earn some money, this will unlock her house as a location on your map.
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WARNING: SPOILERS AND EXPLICIT CONTENT AHEAD
This game is explicit and features sexual acts and content. This wiki may show that content as well as reveal spoilers for the story. Don't say we didn't warn you.
You will need to have built up your Strength and Charisma Stat in order to complete Diane's Storyline.
Part 1
Go to Diane's house which is the purple building in the top center of your map and click on her garden area to start the questline.
She'll explain that you can't begin working as her shovel is broken, so you need to find a new one.
Go back to your house and into the garage and grab the shovel hanging on the wall.
Once you have it return to Diane and you can get to work cleaning the garden. Remove any bugs, weeds, or vegetables that are round. You pretty much only want to leave carrots, eggplants, corn, and cucumbers.
Go back home and sleep and return after a few days to work in the garden once more.
Part 2
When returning to the garden, Diane will ask you to make a delivery of milk to Tony's Pizzeria, which will unlock the area. Take the milk in the back, and enjoy Maria's little accident.
If you have bought the bike, you can now deliver pizzas for Tony and earn a little extra money.
When a few more days pass, come to work on the garden Diane will ask you to move a large wheelbarrow filled with waste. If you can't move it yet you can still work on the garden but you'll need to train your strength before you can progress the storyline any further.
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The next day, you'll come to work in the garden but find Diane drunk instead. Take her upstairs, then get her a glass of water before heading home.
Part 3
The next day, Diane will tell you her vegetables are infested. Clear out the entire garden - notice the new bug has pincers on it's back - then go to Consum-R at the Mall to get some pesticide.
If you talk to the clerk in the store and tell her the bugs have pincers she'll recommend the spray with the green cap so purchase that one (or whichever she recommends) for $100.
Go back to the garden and clear everything out once more and you'll get a scene showing you using the pesticide and fixing the problem.
Tell Diane you've taken care of her bug problem and she'll give you a raise.
Return the next day and once again Diane won't be in her garden. Go inside to look for her and you'll witness her masturbating in the kitchen using a cucumber. Leave and sleep before returning again.
Let another day pass, and Debbie will wake you up. Head on over to Diane's and talk to her in the Garden. She'll ask you to bring an item from the kitchen. Grab the breast pump and bring it to her.
Part 4
After a few days, Diane looks exhausted. She's just finished another milk order, this time for the daycare nearby.
You'll meet Annie's parents, Lucy and Richard. Deliver the milk to the mother, and head back to Diane's. She's already asleep in her room, though. Leave the money on the counter, then head out for the day.
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After a couple days pass, return to Diane's house. Diane still looks tired, so offer to help her out. First, head into the shed and transfer the milk from the breast pump to the jug.
Next, Diane will ask you for a drink, which is random each time. Head into the kitchen and use the notes to make the drink she asked for.
Finally, work on the garden. Afterwards, Diane will ask you to apply some sunscreen. You'll get aroused, but Diane doesn't mind. Enjoy the reward and head home after a hard day's work.
Part 5
The next day, you'll meet Diane's friend Veronica, who works at Consum-R. After the conversation, tend to the garden and let a couple of days pass.
Work on the garden again, but when you're done you'll hear Diane having problems in the shed. Rush in to find out the truth about her milk business--it's breast milk! That doesn't deter you much, though. As a result, you can enjoy some milk straight from the tap.
The next evening, you'll be able to listen in on Debbie and Diane in the kitchen. Diane is worried about growing her business, as demand for her milk has only grown. Head on to bed.
Part 6
The next day, Diane will ask you to drop a package off to the school but if you come on a weekend you won't be able to do it until Monday.
Grab the milk package from inside the shed and go to the school cafeteria on the second floor.
Annie will tell you she can't accept the delivery because you aren't authorized so you need to go up to the third floor to Mrs Smith's office to get her permission first.
Mrs Smith has some strange forms of punishment. After the scene plays out, untie Ronda and have her help you finally deliver the milk to the cafeteria.
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The next day, Debbie is worried about Diane over-working herself, and invites her over to dinner. Debbie asks you to buy a Sea Trout, so head to the pier and talk to Captain Terry to buy the fish. You can also catch it yourself if you have a fishing rod and the right lure.
Take the trout back to Debbie and she'll prepare it for dinner in the evening. Enjoy the food, and the teasing under the table.
Part 7
The next day, Diane has made a big decision--she's going to demolish her house and build a barn in its place! She'll also be moving into the house with you.
However, Richard, the carpenter can't start on the barn right away. Head to the Daycare and ask Richard if he needs help with anything in order to expedite the work.
It seems like Lucy has asked Richard to make some toys for the kids, so offer to make them in his stead. Head into the main part of the house to grab the hammer and handsaw, then go back outside to build the toys.
Afterwards, head back to Diane's house and tell her that Richard will begin work on the house! Take her back home, and she'll now live with you, sleeping on the couch in the living room.
Building the barn will take a week.
Part 8
After a week, head into the kitchen. Diane's barn is ready! Rush over to see the new building.
Richard will be there, and after a bit of conversation, he'll give you a piece of a statue, which can start Daisy's Storyline.
Diane still has a problem--she doesn't know how to up milk production to meet demand. Head on to Consum-R and talk to Veronica. She says that cows produce more milk when they're pregnant, but to head to the library for more details. While you're there, pick up a milk jug.
Go to the library, and speak to the librarian Jane to get more information about breeding cows. Head to the bookshelf and pick up The Breeder's Guide, then go back to the barn and hand over both the items.
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Two days later, visit Diane in the evening on the couch. She seems to like the idea of being bred like cattle... and she wants you to help her make a baby. Head back to your room, give yourself a bit of release, then get some rest.
Part 9
The next day, head into the kitchen. Diane has a doctor's appointment, and she asks you to come with.
Head to the hospital, and talk to Roz. She'll tell you to head on up to the second floor. Both you and Diane need to get fertility tests. Head into the bathroom in order to provide a semen sample. The nurse will offer to help you with the sample, if you need it.
Take Diane back home. It's almost time for the breeding, but not quite yet.
The next day, meet Diane in the barn. She'll ask you to pick up a package from Pink. Go to the mall and head into the store to find Veronica easing her stress for a bit, then return to Diane and deliver the package.
It turns out being a very sexy cow outfit. Diane is finally ready to be bred, and having sex with her finishes her storyline.
Up Next: Jenny's Storyline
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Source: https://www.ign.com/wikis/summertime-saga/Diane's_Storyline
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