DT Maggie would do this for me regularly. I haven't seen her in quite a while, but have been thinking about going back. Personally, I think leaving her finger in there while cumming in her mouth is a bit too much going on at once. My cornhole starts involuntarily clenching, making it slightly uncomfortable, thus detracting a little bit from the orgasm. Although having said that, even a so-so orgasm is still an orgasm. If theres a next time, I'll tell her to pull out when I'm ready to cum.
Also, in my experience, I found that DTM's regular massage skills are actually not bad. Somewhat overlooked due to what she's known best for.