A lot of variables, and Craigslist features both strictly therapeutic, therapeutic + sensual massage, and full-on prostitutes with no massage training whatsoever. Can be exceedingly difficult to tell from the ads. Sometimes you'll see clues in the ads such as "full body massage" or "head to toe massage." The pricing structure can also be a hint. Massage that is well above the going hourly rate probably includes something extra.
Many of the clues come from draping during the actual session. For example: a therapist that uses two-layer draping (sheet + blanket) and only uncovers one small portion of the body at a time....will probably not be open to undraped massage. Doubly so for a therapist that looks away or leaves the room as you turn over. And that means she likely won't be open to happy endings, either.
At the other extreme, a therapist that allows a small towel or pillowcase-sized drape, and removes it completely while working the legs/glutes, and is a bit more careless with keeping things covered, more liberal about nudity, is more likely to offer at least undraped massage.
The middle ground is the tricky part - therapists who use a light sheet for draping, uncover the glutes mostly, and massage the thighs without actually touching the genitals. Those experiences can go either way.
My advice is to build a rapport with the therapist. I never ask for anything "extra" or different on the first visit. If the therapist offers a choice of draping, I choose the least amount of draping she offers. If no choices offered, I simply go with what is there.
On the second or third visit, I will approach the subject if I feel she is open to it, and ask for undraped massage; or tell her she can leave the towel/drape off if she removes it from my glutes. Sometimes a therapist will leave it off on the flip, often times it will be replaced over the genitals.
You're very unlikely to be the first person who wants a happy ending; either the therapist provides them or she doesn't. It isn't possible to "talk someone into" giving one if they don't provide them, so be polite & don't pressure.
If the draping is minimal/absent, and if your arousal is obvious, she may offer. If she doesn't, she may toss up a softball question to you at the end of the massage, something like "did you need massage anywhere else?" Or she may "accidentally" touch your crotch, watching for your reaction.
Some therapists, even if they provide happy endings, may need 4-5 visits before they feel comfortable enough with you. And, for whatever reason, a therapist may not ever feel comfortable enough with a particular client. Don't forget, they're vulnerable to legal liability as well.
Be polite and respectful. And if she says no, drop it. And if you don't get the "vibe" after 4-5 sessions, realize it probably won't happen. Keep seeing her if you like the massage otherwise; or else, move on.
I would say that a therapist presses her breasts against you (even clothed) for more than an occasional brush-by, especially against your face/head, might have some extras to offer. But like everything else in life, there are no guarantees!!
How can you tell when selecting a massage therapist off craigslist if they are legitimate or not? Obviously some of the really bawdy places are giveaway happy-ending salons, but some advertise themselves as licensed with private studios. Is ANYONE on craigslist legitimate?
What signs would there be once the massage starts that it wasnt 100% legit? Curious because my therapist openly massaged by butt with no draping (but draped me when I turned over) plus she seemed (and I don't think is my overactive imagination) to lean over so that her breasts were right in my face (she was dressed appropriately, and not asian btw) when she was massaging my stomach and chest. I thought normally they come from the side when massaging those areas? Anyways, just curious what I am dealing with here.