Very simply: Riley (handjob) and Aubrey (fingered) should always offer to help when you tell them about the list.
The condom can be taken from Ryan during the second free roam and the underwear should be found after either Riley or Aubrey's scene.
Amber (bj) requires you to have told her to get clean.
Penelope (oral) requires you to have been on her path since CK1 (ie won her case so that she goes to Europe; took her to the concert and went backstage) and not have messed it up in CK2 (ie take her on the dinner date, don't let her get distracted by the other diners, next morning don't tell her you'd have preferred sex, save her from the conversation with Chris at the party).
Autumn (making out) requires you to not be dating Lauren (which means you can't have had sex with Lauren in Paris).
Lauren (sex) will, as you can't be in a sexual relationship yet, require you to have kissed her before (or possibly just be friends) and have a loyal kct at the end of the party. Don't buy her the giftcard.
