No, I just checked my bill and it does not show IMessages
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Regardless of how or why you sent a text message, once it is sent from your phone it is billed as a sent text message.
no.
there are parental plans that show all messages sent and receive in their siblings cell phones.
A toll-free number generally will not show up at all on a landline phone bill, because there is no charge for it. A toll-free number may show up on a cell phone bill, because you still pay for the airtime, even though there is no long-distance charge. It may or may not be specifically marked as toll-free.
I think it might show who you've been texting, but not the actual message it said, but yes, the amount of text messages does show up on the bill, but it sometimes depends on the company, as it may tell how many text minutes you have left, or something to that affect.