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In the Johnlock parts of the Sherlock fandom, at least the corners of it I've seen, there seems to be three main theories about Sherlock's virginity. Specifically:
- He either had past romantic relationship(s) that didn't work out well, Victor Trevor being the most common example,
- Or he had romanceless sex as an experiment to see what all the fuss was about but didn't really do romance until John came along,
- Or he was completely a virgin and his and John's first time was his first time, full-stop.
Of these, my personal headcanon is (2). Quite a lot of crimes are connected to sex, even the ones that aren't really sex crimes in the literal sense, like spousal abuse or murder out of jealousy. Plus it's such a huge part of the human experience, so I have a hard time imagining Sherlock just not having any interest in exploring this part of human nature, even if he wasn't sexually driven for the usual reasons. It's not that I have any problem with someone rounding thirty and still being a virgin; it's that this particular person, with his intense curiosity and drive to understand and without any obvious moral objection, I struggle to see him choosing to abstain.
I'm also, I have to admit, a little put off by the idea that virgin!Sherlock has been "saving himself" for John, or that his virginity is something special he can "offer" John. This is a bit odd in a way, because I'm a Christian and I still accept the sexual morality I was raised with. That doesn't mean "gay sex is bad" for me these days, but it does mean at some level the ideal is sex within lifelong monogamous relationships if not institutionalized (or sacramental) marriage. I recognize it's a little odd that my ethical beliefs don't really match up with my intuitive headcanons and expectations for this character here.
It also should be said: there are some fan authors who have done wonderful things with this trope and who have convinced me that it's a good start to the relationship, at least within the confines of that story. Usually when it works with me, it gets turned into a tool for showing that for Sherlock, sex and particularly orgasm has meant the loss of control and the giving into sentiment - and that with John he can let go of that inhibition a bit. There's quite a bit of Doyle canon to back this reading up, e.g.Sherlock's reaction to Watson's falling for Mary Morstan in The Sign of the Four, in particular his comments about love meaning the abandonment of reason. I think what bothers me with this approach is the assumption that virginity is somehow a thing that must be be preserved, that cannot be recaptured, and that Sherlock in particular should have in his possession. John is the man who's allowed to leave a trail of women across three continents, we're allowed evidence of his (pre-wedlock, even) sex with Mary through the pregnancy - and yet Sherlock must be a virgin or he no longer has something important to offer to John. The idea plays into purity culture ideas in a way I am not at all on board with, and while certain authors can certainly overcome that prima facie discomfort, it's something that must be addressed in specific fics. Out of fairness, many do. It's just that when this happens, it corrects the problem for a certain fic, not for the category as a whole.
(Also out of fairness, I have no problem with the idea that Sherlock was functionally asexual or demisexual until he met John and it was the first time he fell in love and so the first time he wanted to have sex. The problem is I'm yet to read fics that do a good job explaining what about John (or Sherlock's life generally) that flipped that particular switch, so those stories haven't felt authentic or convincing to me in the past.)
There is one option people seem to overlook quite a bit when they're doing this kind of issue, which I find both troubling and fascinating, all at the same kind. At least in Doyle canon, Sherlock doesn't seem to have finished university. He also has a drug habit, in the BBC verse enough of one that he's resistant to sedation and that the police seem to assume he'll just have drugs around his flat. While in some ways he's not hurting for money, he doesn't seem to have what you'd call a steady career. No real nest egg, and even if he had one a serious drug habit can blow through a savings account quite easily I've always suspected his lifestyle was supported by a combination of Mycroft supporting him and/or family inheritance, combined with fees from private clients. If either one of those sources dried up (which an even-slightly-out-of-control drug habit could easily do) he might find himself hurting for money. Very, very quickly.
I've seen enough police procedurals to know (at least in that fictional world) a lot of people get into crime and particularly prostitution because they need drug money. Sherlock being Sherlock, I don't doubt he could go into robbery and even half-high get away with it; but I also think that might seem like a bridge too far for him. I can see Sherlock not wanting to risk an actual police file, and not wanting to connect the "bit of burglary" he would have to do for his investigations with actual burglary he committed himself. Plus, I can see it actually flattering his ego. People are so stupid, they're so hormone-addled and he's so gorgeous they'll pay him to use his body and it wouldn't necessarily mean anything to him. Except it would, in time; or perhaps it really wouldn't. What would Sherlock think of that period in retrospect? How would it shape his view of sexuality, if his first real initiation into it was in the context of using and being used so he could get what he wanted, drug-wise? What would John think of it all?
It's not exactly a pleasant possibility to think of and I can see why people wanting to write fluffy Johnlock might prefer not to go there, but I think it is a fascinating one, and one more or less free of those gender norms and purity culture hangovers that bother me with the whole Sherlock-is-a-virgin-before-John idea. It could give you a Sherlock who's sexually experienced at a technical level but still rather emotionally virginal while scarred at the same time.