I was going to comment on I don't get the need for it to be a milf, and if that actually is his preference, then so be it. I have seen young, legal men with a MILF fetish before, they're often sweet and beyond respectful, grateful someone is willing to take their desires seriously. They had to wait until they were legal to even be able to have access. It is them searching, not me. I don't see it any different than me being with an 80 yro who is looking to share time with me.
By the looks of it, it was only once they were legal that they were finally able to muster up the guts to lose their V-card with the aid of a pro. To a hopelessly virginal adolescent, something like buying/renting porno in secret (remember when we'd rent that stuff?) feels like a walk in the park after dark compared to climbing the mountain that is paying someone to get them laid. Under cover of anonymity, I have the freedom of revealing that I only lost my virginity at 23, to a lady of the evening. It seems young men are losing theirs at increasingly later ages, primarily due to how the ease of access to free smut greatly reduces the burning urge to fuck (as an anecdote: during the communist regime in the Eastern Bloc, I've heard testimonials that it was far more common for teenagers to go see "the girls", as smuggled porno magazines were few and far between so even after you and the other boys in class got your grubby hands on one, it wouldn't calm the biological urge for long until you were craving the real thing). To pro-abstinence sex ed types from the 80's-90's, I suppose this represents the best case scenario because hey, at least teen pregnancies are down.
Back on the subject of broken arms kid, from what I gather it was supposed to be a short-term fix while he was injured, but they both got too into it so it just kept going. Hiring a pro costs money for one, plus the hypothetical situation of hiring one "his age" (14) is the greasiest option by light years. Because well...child sexual trafficking. Given the massive popularity of MILF porn, I'd suppose more than one guy has asked himself the prickly hypothetical question of "man, if my mother looked THAT good, would I be tempted?". I prefer to stay the hell away from that question (my mother was a saint, we do not ask questions like that) but will admit that incest roleplay (could be as simple as me addressing my partner as "mommy") does feel weirdly satisfying. She has to be more on the mature side for it to really work tho.