When scheduling a make out session, it is always important to place his needs above your own. If he has requested leggings that is a good sign, as it means his libido is of great health and vigor. Yes, you should wear them for him. After all, he has gone through the trouble of scheduling a make out session with you, certainly he is penciling you in between his important business cases and raising his children.
The king of shirts is a tricky one. I once knew a King of shirts but he was eventually arrested for climbing a mountain in a restricted part of a national park. Those were strange times in the Shah's Republic!
There are several kissing positions. One of the most popular with young people is called "The Frenchman". It involves having an underdeveloped taste in American tobacco while simultaneously resenting America for its role in the second World War. Another popular move is called "Granny Hopping" where the tongue gently sweeps the inside of the partner's mouth, as if one were working on a Werther's Original.
If you "go farther" you should shave "it" as you see fit. In the 1970s it was popular to go al naturale, as evidence by the 1979 documentary "Shaving Sharon", a film that follows four suburban youths as they go through their first shave. Does he have a mustache or a beard? If so, you should shave first by buzzing it with a No. 1 clipper because trying to use a razor on such thick hair will result in resentment and mixed feelings on his part.
Also when you "go farther" you should act confused and surprised. Constantly apologize and use phrases like "They didn't teach THAT in science class!" or "Will you replace my absentee father?" These are what is known in the make out community as trigger phrases, phrases that will certainly endear you to him. Whatever you do, do not ask him about his a.) wife nor his b) retired mother nor his c) outstanding medical school loans.
a lot depends on how far you will let it go. does he get boob access if he tries? if yes, then make it an easy bra if you have one, or one that easily stretches over your tits and lets them out but won't choke you. if your not against it be willing to fondle him because he will love it.
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If he told you to wear leggings, that's a hint that he wants to get in your pants.
a) wear what is comfortable, but be a little sexy at it too
b) there are no real kissing "positions"
c) shave your bikini line and that should be fine.
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