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I know that the "s" becomes "z" when it comes after a voiced sound. And it is pronounced as "s" when it comes after a voiceless sound. I also know rules about possessives but I don't know how natives pronounce a word when it ends in S and "apostrophe S" is added to it.

For example: "Stannis's army".

Do you add another syllable to it? Like Stannisiz? or just Stannis and ignore the possessive S?

I really have difficulty in pronouncing words that end in S and possessive S is attached to it.

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Yes, an extra syllable is added to its pronunciation, so it's pronounced Stannisiz ([stænəsɪz]*).

Whenever a word ends in a sibilant or an affricate and you add the 's to it, the 's is pronounced [ɪz]. The pronunciation without the extra syllable is also common.

  • Sibilants: /s, z, ʃ, ʒ/
  • Affricates: /t͡ʃ, d͡ʒ/

I have explained why add an extra syllable for the 's in another answer to a question asking Why are there three pronunciations for the plural “-s”?, I'll just copy-paste the relevant bit:

Sibilants + S

  • [ʃ] or [ʒ] + S

When a word ends in a sibilant [ʃ], it's voiceless and when we add the [s] then we get *[ʃs] cluster, which isn't permissible, so we insert a vowel between both the sibilants in order to break that cluster and conform with the rules. After inserting the vowel, we get [ʃɪs], now we already said that the -s is [z] after a voiced sound, and the vowel is voiced, so we change the [s] back to a [z] and get [ɪz] therefore the word bushes is pronounced bush[ɪz]. When a word ends in [ʒ], we do the same as above.

  • [s] or [z] + S

[s] and [z] are sibilants, but I'm going to explain them separately. When a word ends in a [s], it's a voiceless sound, so we add the [s] form of the -s ending; bus + [s] → *[bʌss], here we have a geminated s and as we read in the rules that tautosyllabic geminates aren't allowed, therefore we insert an epenthetic vowel [ɪ ~ ə] to break the geminate: [bʌsɪs], we change the terminal [s] back to a [z] because the sound preceding is a voiced (vowels are always voiced): [ˈbʌsɪz].

The same goes for words that end with a [z]: when a word ends in a [z], it's voiced so we add the [z] form of the -s ending: rose + [z] → *[ɹəʊzz], here we have a geminated z, so we need to break it, therefore we insert a vowel: [ˈɹəʊzɪz]

  • Affricates + S

Affricates—[t͡ʃ] and [d͡ʒ]—are complex segments. The second segment in both the affricates is a sibilant. So we get Sibilant + Sibilant, which isn't allowed. Therefore we insert a vowel between the affricate and the [s] or [z] to break that cluster. Beach + [s] → *[biːt͡ʃs] + [ɪ ~ ə] → [biːt͡ʃɪs]

It holds true for possessives and present singular -s too.

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  • You will sometimes hear people say something more like Stannis army, but yeah it's supposed to be the extra syllable. Also when you're speaking quickly, the vowel can become a schwa or disappear entirely, and the z can just become a s, so you get a quick ss-ss sound. That's the key part really, adding a z/s sound to the end of a word to make it possessive - if the word already ends in that sound, you need a distinct extra one so you can hear the difference. Just in case that makes the pronunciation a bit easier! Sep 16, 2020 at 13:09
  • Ill-formed constructs are marked with a preceding asterisk.
    – Void
    Jan 8, 2021 at 20:08

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