Name two English words ...

[ChrisGreaves]

Name two English words that possess five occurrences of the letter “s”.

[Leif]

I assume you don't mean something like George and Harry?

Spoiler

dispossessed
possessions

[Rudi]

Spoiler

How about: assesses

[StuartR]

Spoiler

Assassins
submissiveness

[Timelord]

Spoiler

Mississippi's?

[Rudi]

Spoiler

Mississippi's?

[Rudi]

    
How about 6 s's...

Spoiler

Senselessness

....and just found one with 7 s's...

Spoiler

Successlessness

[ChrisGreaves]

Name two English words that possess five occurrences of the letter “s”.

Is it too late for me to post the answer?

[HansV]

You're not satisfied with the solutions provided?

[John Gray]

I rather liked
POSSESSIONLESSNESSES (9 s's)
and
STRESSLESSNESSES (8 s's).

[Rudi]

Nasty!

(Can those actually be pluralized?)

EDIT: I can't even beat 9 with:

Supercalifragilisticexpialidociouslessness

[HansV]

And words that don't contain an "s" suffer from multiple S-POSSESSIONLESSNESSES

[John Gray]

Nasty!

(Can those actually be pluralized?)

EDIT: I can't even beat 9 with:

Supercalifragilisticexpialidociouslessness

I would agree that these words push the bounds of intelligibility.

[ChrisGreaves]

You're not satisfied with the solutions provided?

I'm speechless (3)!
I came across "possessions" and the like and was curious.
Once we get to 10-esses i think we should stop and leave something for the youngsters coming along behind us ...