Life pro tip: Maybe give her some pointers if it's her first blow job.

Don't give her pointers, she will delete them and leave you with a core dump

I have never, ever, understood the appeal of virginity. Who prefers someone who is uncomfortable, awkward, and doesn't have any experience?

This has always baffled me. This is one reason why I think sex workers should hold a high status in society: they provide an valuable service in training the uninitiated and unskilled. It's like taking tennis lessons, and all your future partners should be grateful for their lessons.

Virgins don't know that you suck at sex. It's an insecurity thing. Most people don't realize it.
- And then there's me. Who has been with one woman, who was actually appalled by the whole attachment thing, but controlled so much of my life that I became permanently awkward, uncomfortable AND stuck with super low self esteem.
  
  I don't know if I suck at sex, or just suck in general. If I survive this divorce I'll take that win right now.
Disclaimer: I am not holding or promoting the following.

But the meme is "if you're gonna eat a sandwich, you'd like it better if someone hadn't fucked it first"

I think the core of the meme revolves around possession. Seeing the "sandwich" as something to attain, and possess, and consume. Indeed, I would not like someone to fuck my lunch. But a person has an independent life where their value is certainly not graded in such a way. ( Or any way, in this context)

If you are obsessed with taking something pure, and only having your influence on it, for all time, then the virgin thing matters.
I want to stay a virgin because I don't like sex. If I wasn't a virgin, it would mean something very bad had happened to me.
- Worst case scenario, you lose your chance at wizardry at the age of 30. Keep it at all costs friend.
  
  The magic missile and fireballs are well worth it. Especially the spell "mend buttcrack".
- That's not how I meant it.
  
  There's a cultural value in virginity in girls. It's pretty common across cultures: for marriage, virgin women are more desirable than non-virgins. It's biased; the virginity only increases value for girls, and it probably stems from men wanting to be sure than any prodigy are actually theirs. Women can be nearly 100% sure a kid they have is theirs (not quite 100%, as there's a brief period when a channeling swap could conceivably be made), but the men can never be certain. The best odds you have is to get yourself a virgin. So female virginity has been valued through history (by men), and I think this is where the fetish of having sex with virgins comes from.
  
  That's what I'm taking about. I've never understood the appeal of "being a girl's/boy's first."
You are obviously not a germophobe.
- What do the germans have to do with it?

I recently had sex with a longtime friend who didn't really seem to know her way around a blowjob. I'm getting ready to have a playdate with a married friend whose husband wants to watch. As a result of the first and in anticipation of the second I made up an essay about what I like when receiving head and offered it to my married friend. She accepted and said that she was happy that I did.

Some of the best head I ever had was from someone who liked encouragement play and I just monologued what I liked about what they were doing the whole time till I came.
- That's awesome. I have Asperger's and always ask, "Teach me what you like. Show me how you get off." then, "Do you like this? Do you like this? More or less? Do you like this here?" If they can teach me what they like I will do it and variations on the theme.
  
  One thing that I think really benefited my technique was watching my wife and an old fuck buddy of mine go down on each other. I noticed that they both did the same thing so I tried it to very positive reviews.
- I read that Gordon Ramsey does the same thing.
- Misney makes 'em pay!
- It's weird seeing misney in the wild
The way you just casually discuss cuckolding people. It's like the banality of evil as they called it or in this case the banality of cucking
- He wants to watch and participate. Not cucking.
- Huh? It's not my jam but in their story everyone seems to know what's going on and consented. What's wrong with that?
- Sex shouldn't be this weird thing we make it out to be.
  
  If everyone is comfortable with this proposition, then go for it. It's not for everyone, but in this case, there is no shame and no hiding. OP even communicated in advance what are his limits.