Wish he had cum inside of her ass, zero pregnancy risk and just knowing what comes out of that orifice, I mean why waste the opportunity? It's a human being's most intimate orifice.
Definitely not her first time. I used to meet many younger women through Craigslist back in the day who contacted me to get their ‘silver daddy’ experiences and also explore sex acts they knew should be explored with an older, married man. I had a few complete virgins who wanted to ‘lose it all’ at once and many, many anally curious but shy. Guiding a female through her first anal experience is no cakewalk and one encounter took over 3 hours! Although it may seem antithetical, I highly recommend women have their first anal experience with a large-penised male. From my many experiences, it appears to feel more intense for the female and they cum HARD! Don’t waste your time on small penises.