Also forgot to mention I just use the AstroGlide Gel lube you can get at any pharmacy. Works well for the purpose, but it's a bit sticky in application so make sure towels are handy. Haven't tried experimenting with anything else.
Did you guys ever end up trying pegging? Best advice I can give is don't let your eyes be bigger than your asshole. Just start off with a normal sized toy and see if you need to go bigger. We have a CalExoticSophia Red Rider: https://www.amazon.com/CalExoticsSophias-Red-Rider-Harness-Dong/dp/B001RNI8SA. I really like this one and it's a normal size. It's only real downfall for me that is that it seems to work best in doggy style or reverse cowgirl because of the way it curves.
Other things to be aware of is try to stay clean. I don't enema or anything like that but I try to watch what I eat a day before. I also did solo practice with the toy for quite a while until she used it on me.
You'll probably both be nervous about it the first few times, but this is normal and you'll get over it.
I found a new type of strapon that actually fits in me and works in against giving it to someone else. I actually bought it for our female fuck buddy but works as well on him! He orgasms much harder with thst stimulation!
Other things to be aware of is try to stay clean. I don't enema or anything like that but I try to watch what I eat a day before. I also did solo practice with the toy for quite a while until she used it on me.
You'll probably both be nervous about it the first few times, but this is normal and you'll get over it.
Good luck!