Why is my script not working?

My random music player is meant to play random music constantly but it only starts to work when a player joins but it doesn't start until the permitted players say the skip command and even then it only plays 1 song once and not again until the skip command is said. Please help me fix this!

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--                            Script Made By UndiscoveredLimited                            --
--                                 Put This Script Anywhere                                 --
--                            Change The Variable Below's Values                            --
--                          DO NOT LEAVE BLANK SPACES, DELETE THEM                          --
--                             WILL NOT WORK WITH ONLY ONE SONG                             --
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SoundIds = {"142397652","154309298","154764197","161006106","144635805"}
Permission = {"UndiscoveredLimited"}
SkipCmd = "skip"

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for i,v in ipairs(SoundIds) do
    game:GetService("ContentProvider"):Preload("http://www.roblox.com/asset?id="..v)
end

Sound = Instance.new("Sound",game.Workspace)
Sound.Volume = 0
Sound.Looped = true
Sound.SoundId = "http://www.roblox.com/asset?id="
Skip = false

function Skip()
    Current = SoundIds[math.random(1,#SoundIds)]
    Last = Sound.SoundId
    wait(4)
    Sound.SoundId = "http://www.roblox.com/asset?id="..Current
    while Sound.SoundId == Last do
        Current = SoundIds[math.random(1,#SoundIds)]
        Sound.SoundId = "http://www.roblox.com/asset?id="..Current
    end
    Sound:Play()
    wait(1)
    for i = 1,10 do
        wait(0.25)
        if Sound.Volume ~= 1 then
            Sound.Volume = Sound.Volume + 0.1
            end
        end
        wait(110)
        for i = 1,10 do
            wait(0.25)
            if Sound.Volume ~= 0 then
                Sound.Volume = Sound.Volume - 0.1
            end
        end
    Sound:Stop()
    Skip = false
end

game.Players.ChildAdded:connect(function(Player)
    Player.Chatted:connect(function(Chat)
        for i = 1, #Permission do
            if Player.Name == Permission[i] then
                if string.lower(Chat) == SkipCmd then
                    Sound:Stop()
                    Skip()
                    Skip = true
                end
            end
        end
    end)
end)

while Skip == false do
    Current = SoundIds[math.random(1,#SoundIds)]
    Last = Sound.SoundId
    wait(4)
    Sound.SoundId = "http://www.roblox.com/asset?id="..Current
    while Sound.SoundId == Last do
        Current = SoundIds[math.random(1,#SoundIds)]
        Sound.SoundId = "http://www.roblox.com/asset?id="..Current
    end
    Sound:Play()
    wait(1)
    for i = 1,10 do
        wait(0.25)
        if Sound.Volume ~= 1 then
            Sound.Volume = Sound.Volume + 0.1
            end
        end
        wait(110)
        for i = 1,10 do
            wait(0.25)
            if Sound.Volume ~= 0 then
                Sound.Volume = Sound.Volume - 0.1
            end
        end
    Sound:Stop()
end