Bonus if there's a plot.
The Ed Walters stories would fit.
Are you looking for only milfs?
It could be Lubrican's Making of a Gigolo https://storiesonline.net/series/389/making-of-a-gigolo
If you don't mind a mix of teens and milfs in a VERY long story , try Six Times A Day by Spacer X. https://storiesonline.net/s/52707/six-times-a-day https://storiesonline.net/a/Spacer_X
The Accidental Gigolo by Marsh Alien (PREMIUM)
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