Well that’s not a very gentlemanly thing to do, not actually pay afterward if a deal was struck in advance.
Since I only see millie's posts second hand. An admission made while drunk is still an admission. No one in their right mind would brag about paying for prostitutes when they never do.
If I remember the context of the post correctly, which I have a high confidence in, he claimed to have been with two women and mentioned the paying. An ancillary memory is that it was at Red Rock Casino that he was doing this.
The time frame was probably while Heather was still doing her original dumpster fire of the podcast.