Update on my goals now that it’s been a few weeks!
Blow Jobs - I’m still gagging a bit when his precum starts coming out 
I got the LH cherry lube 
and that has helped a lot. I like the taste of it, so I ordered the LH strawberry lube too to compare 
(arriving later this week). I also saw in some other threads that a lot of guys like wet sloppy blow jobs, so I’ve been salivating more on his dick, and that’s making it a bit easier for me (and no complaints from him 
) Also, the last couple times have been in front of a big mirror so he could enjoy the view 
I was planning to let him cum on my face today (that would’ve been a first), but he sprayed straight up and then it oozed down the sides of his cock. It was funny, he was like, I’m about to cum, quick! Why don’t you have a tissue!?! Well, that spoiled that surprise for him 
Still working up to letting him cum in my mouth. I’m still worried I might gag and throw up on him (and he would feel terrible if that happened)… But I feel like my technique is getting better, and while he’ll turn me down sometimes when I want to masturbate together or have sex, he never turns down a blow job 
Anal - I had a couple days here and there the past few weeks that I skipped anal play, and man, my hole just shrinks back down if I skip a day 
I’ve been enjoying my beads and small plugs, but my biggest plug (4 inches at the widest point) hurts if I haven’t had anything up my butt the day before… He got two fingers in during foreplay this week (he had only ever put in one before then) so I’m feeling positive! I’m also starting to really enjoy climaxing with anal stimulation (combined with clitoral stimulation). I found another plug I want to get to wear for longer periods before our anal play together so that I can be stretched out a little more beforehand!
It will take some time, but I’m happy to see that I’m making some progress here and there 