On the contrary, feeling at ease and having confidence is usually the most limiting thing when it comes to men relating to women and establishing long (or short) term relationships. Read any dating advice for men; the biggest thing pushed is how you carry yourself and how comfortable you are with the women you interact with.
I know from personal experience that, for a guy at least, retaining your virginity longer than “average” tends to make the insecurity and nervousness increase exponentially and can really make you put extra pressure on yourself to be like everyone else… this of course comes across to women as being uptight, not relaxed, insecure, etc. Leave it too long and you can devellop a real mental problem as described above by the 50 year-old guy story further up.
My reading of the OP is not that he’s trying become accomplished in bed by hiring a tutor (agreed that won’t happen), but is more looking for a way to get over a personal self-limiting psycological condition that’s probably holding him back from being more relaxed and open to women in general. If that’s the case then I’d say go for it, but do some research first.
You don’t need to go to a foreign country; every country will have a long standing home-grown prostitution industry; just get to know it a bit. If your goal is to confirm to yourself that getting laid is really no big deal, then don’t go applying for a passport, book plane tickets, and spend thousands of dollars on what will end up as a 30 min session that will boil down to 5-10 minutes of actuall play-time). IOW, don’t make it a big deal - because it’s not. Also, unless you live in a very heavy-handed religious or otherwise legally-uptight country, the legal risks are pretty low if you use a bit of common sense. STD-wise, always use protection but don’t get too hung up on the fact she’s a hooker; there’s a large proportion of non-hooker girls that take far more risks and sleep with complete strangers who they can’t even remember… and the off-putting thing is they look identical to any other woman; regular girls are risky too and I’ve never met a woman who presents a confirmed list of previous partners and STD tests they’ve had performed. At least an escort will use a bit of discretion with who she has as clients, will use protection and safe play, and get tested regularly. That’s a lot better than the girls-gone wild chicks who get wasted and hump their way through highschool and college & spread 'em for any guy who happens to be stumbling around the same house party they are at.
In general, you should stay away from street walkers - they are out advertising on the street corner because they need the money right now and take a lot more risks; usually to feed some sort of addiction or abusive relationship. Escort-level girls are generally safer, but read through the ads carefully, and do search the reviews (a modern day convenience offered through the internet). It’s probably worth following the ads for a couple months and go more for escorts with consistent presence and good reviews. Those girls treat what they do as a real job and take proper precautions. I’d avoid escorts who are just in town for the weekend, who offer a lot of cheap specials, or change their names and numbers a lot.
If the OP is considering this for the reasons I’ve hypothesized, then he’d only do it once or twice maybe - to get over the “never did it” mentality. After that, go on and establish more normal relationships… keeping in mind that “normal” covers a very large spectrum. I’d just not mention it to anyone that I banged an escort; the stigma is so strong and IMO overblown. You could still mention that you only hooked up with 1 girl a few months ago for the first time if you want to convey a bit of honesty to a girlfirend - just leave out the part where you slipped her $100 first :). You have no real way of telling that her stories are true either, and an aweful lot of girls have an experience or three they feel really embarrased about themselves that you probably never will hear about even if you marry them.