I understand the joke part of it. But for the OP's original statement, which doesn't sound like he's joking, he makes it sound like his virginity has anything to do with being arrested or what his time would be like in jail.
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Provided he tells no one, no one will know. And even if they DID... unless the crime he committed was severe enough that he won't get out of jail for decades, and he's experiencing a fear of missing out I guess
Well, yes. If you've never had sex before and your first experience is being anally raped, I think it would be quite terrible. Rape in itself is already terrible, but to be stuck in a situation where you lose your virginity by an almost certain prospect of rape, lots of people would consider offing themselves. You still had hope of having sex one day, and then boom, you're in prison, you might contract an STD, and both being a prisoner or an ex-convict and having an STD significantly reduces your chances of getting to be in a long-term wholesome relationship with copious amounts of happy sex. You'd probably require therapy at the very least.
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Provided he tells no one, no one will know. And even if they DID... unless the crime he committed was severe enough that he won't get out of jail for decades, and he's experiencing a fear of missing out I guess