Positive one-night stand virginity stories? Curious if they exist

Throwaway for obvious reasons. I’m 30, and I’ve dated a bit in the past, but I’ve never been in a real relationship and I’m still a virgin.

Part of it is insecurity. I have a hard time being vulnerable physically, and I tend to avoid things I’m not immediately good at. I also haven’t prioritized dating in years. And now, I feel stuck. I want sex and intimacy in my life, but being a virgin makes me feel like I’m too behind and it’s hard to even start.

I’ve thought seriously about just arranging a one night stand and getting it over with. I’m comfortable with my body in private (though insecure), have experience with toys, and honestly I think it could be a fun, freeing experience. Maybe it would help me loosen up and start enjoying intimacy and dating more freely.

But every advice column says don’t do it. That I should wait until I’m in love, or at least tell the guy first, which I don’t know if I want to do. I was even thinking of being upfront on Tinder with an anonymous profile, just lingerie pics and honesty about wanting someone kind and patient to help me through it.

Has anyone lost their virginity through a one night stand and felt good about it afterward?

Or if you lost your virginity in your 30s, what was that like?

Also any advice relating to one night stands is welcome. I am. out. of. my. depth. over. here.