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I think when two people care about each other and trust each other, and also feel physically attracted to each other, that initiating sex should just come naturally.
It shouldn't be contrived, where you're thinking, I want sex, so I'm going to do x. When people want each other that way, it just follows more or less naturally.
I'm not sure I could pinpoint specific things guys might do...perhaps one of the clearer advances might be to stroke her breast, or pat her bottom, through her clothes...if you're lying down, wrap your legs in hers and thrust a little...kiss her neck or bite it a little more purposefully...all these are harmless and if she's not in the mood she'll just let it fizzle out. If she is, she will likely reciprocate and it's on! Sometimes, a lustful look is all it takes.
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Whether we write or speak or do but look
We are ever unapparent. What we are
Cannot be transfused into word or book.
Our soul from us is infinitely far.
However much we give our thoughts the will
To be our soul and gesture it abroad,
Our hearts are incommunicable still.
In what we show ourselves we are ignored.
The abyss from soul to soul cannot be bridged
By any skill of thought or trick of seeming.
Unto our very selves we are abridged
When we would utter to our thought our being.
We are our dreams of ourselves, souls by gleams,
And each to each other dreams of others' dreams.
Fernando Pessoa, 1918
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