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How Do You Press A Fruit?

Depends on the fruit. Small fleshy fruits can be pressed with the rest of the plant, as can small dry fruits (e.g. capsules or other botanical fruits that wouldn’t be colloquially considered fruits). Obviously pressing small fleshy fruits means that they’ll get squashed and deformed; there isn’t really a good way to deal with this.
For large fruits, most herbaria will have boxes at the beginning of a genus where fruits can be stored separately from the pressed specimen (you’d need to note on the specimen label that there is a seperate fruit collection). There are a lot of tropical plants out there with large non-fleshy fruits that would just need to be air-dried.
For large fleshy fruits, you might be able to put them in a plant drier loose (not in a press) to dry them; I’m having trouble thinking of anything that this would work well for, but there might be something for which this would be appropriate.
None of the above will really work for plants with the kinds of fruits you might buy in the supermarket. For these, you’ll want to section them, possibly remove some of the pulp and put them in the press (or maybe loose in the plant drier). For an apple (or other pome), I’d make a cross section slice through the middle of the fruit, and maybe additional slices including the top (peduncle) and bottom (flower) of the fruit. A small drupe (like a plum), I’d just cut in half (longitudinally) and put both halves in the press. A larger drupe (like a mango), I’d cut in half longitudinally, discard (or eat) the half that doesn’t have the seed, and put the half with the seed in the press (maybe also scooping out some of the pulp). Cactus fruits should be cut, with a good deal of the pulp removed. For large “berries” (pepo/hesperidium/etc.) like a grapefruit or a canteloupe, cut a cross section out of the middle and put that in the press.