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Open communication is key. If everybody in the relationship is talking through the issues, the main issue (jealousy) should be avoidable.

Is there any advise on what position to do first?

I've got one word for you: vegetables. That's where I started with anal play. Wander through the fruit and veg section of your supermarket… all sorts of shapes and sizes  :cool2:

@ckslad: is brother in law incest? Nope Go for it

Every answer so far has been exactly what I would have said.

@slimsf888: Jealous of the 13% who have it daily! Newlyweds or professionals. 

I'm of "a certain age" and came out just as the health crisis was hitting panic mode in the early '80s.  As a consequence, I've had relatively few partners and less sex than one might think of a healthy gay male.  Sex has been fun when it happened, but there was considerable worry and angst associated with it as well.  (Frankly, I harbor a lot of jealousy over the life I should have had: I paid the price for being gay, but didn't get the supposed benefits.) Within the past year, I started PrEP.  I can't say that I've become particularly slutty, but I can say that the worries I used to have have been greatly reduced.  I love to bottom and it's made all the difference in the world for me.  I still check my partners' statuses and play safe if bottoming for a positive guy; but I'm more inclined to bareback for a guy who is also on PrEP. Does that make me a slut?  I don't think so, though your mileage may vary.

Avoid regular use of medical enemas as this can lead to lasy bowel syndrome. Instead, go for water or saline enemas/washes.

Highly recommended for solo play and with friends/partners.  :cheesy2:

Catfishing is evil. I know people of all kinds, gay, hetero, etc who manage to have relationships, so there's no excuse.

"Without" is great but have to make sure the safety. Just mentioned STD and STI can be infected even you use Prep. Just make sure the one you want to do bareback is totally trusted. Do not recommend unsafe sex.

I'm 33 and more passive/submissive, so I'm not really looking for too young or inexperienced. Though I've had several recent encounters with guys in the 21-24 range. I wouldn't go under 20 and is usually looking for 28-ish and up. Biggest age difference is when I was 16 and he was 45. Oldest guy I've been with (that I knew his age) was 57 and I was 30 at the time.

I like those.

Don't assume anal sex is gonna hurt!  I mean, it can, a bit, depending on your tension level, anatomy, etc., but it can also be completely pain free and pleasurable.  Take it slow, only go as far as you're comfortable.  99% chance you'll get the hang of it soon enough.  It's a dick, not a dagger, so don't worry too much.  ;D

If porn stars count, then yes…. Marc Dylan