One more thing. He likes using the Shunga massage oils. Could that work? Or is oil a no no for anal?

My wife and I found out that the thicker lubes work best for anal. If the lube starts getting him soft, just manually begin to masturbate him with your hands and a whole lot of lube - he'll get hard pretty quick.

We actually found that the easiest position of anal entry was actually doggy from behind. It put the least amount of straqin on my wife's anus as she was ablt to relax better that way (with no anal tightening). Your partner just has to be careful when he enters, not to go to deep right away as the doggy position kinda makes it real easy to go deep.

The last thing is - take is very slow. Hope this helps!

When we were first trying, I found it easiest to be in a missionary-like position. It doesn't seem to allow for as deep of penetration. We used (and still do) lots of lube and progressively larger toys until I was able to handle him fairly comfortably.

My two favorites are lying on the back, legs up and doggy. I'm not a newbie anymore, but both of those seem to allow you to relax pretty well.

I don't know why I never thought of missionary or any variation of it. Thanks all!

If anyone else has any other suggestions that would be great.

Also still wondering if massage oil works well as a lube for this.

There are many positions but I would suggest that you lie on the bed close to the edge, perpendicular to the floor, raise your legs, holding them up and let your partner penetrate your butt while standing on the floor. Also your ass should be warmed up, the Jolly Jack is good as are a number of butt plugs and dils with wide bases. Also use a vibe or his or your fingers on your clitoris prior to anal penetration. Relax. An orgasm prior to anal sex always helps.
I would forget the massage oil and use a thicker lube such as Maximus(be generous with the lube on your toy, his penis and your butt hole.
Also go slow and direct him on how you feel. Anal sex should not be painful but an area to find new sensation and satisfaction.
And never switch from anal to vaginal but from vaginal to anal is ok.

I've only recently been able to fully enjoy anal sex with my boyfriend. It took quite a bit of prep work! We used a bumpy glass probe that started out small and grew larger to warm me up. Then we slathered on the lube and started inching him in. We've only ever used doggie style for anal. It gives him slightly better aim and I feel like I have more control over how deep he goes.

Massage oil (or any other sort of oil) doesn't work very well for anal. It's too fluid, so it doesn't stick around where it's needed. Invest in some good quality thicker lube - you'll never regret it.

I usually start off either missionary or a variation of that on my side. I feel that doggy is the worst to start off with since it tends to be deeper. Also, facing your partner they can tell if you're in discomfort by your face before you can even need to say anything.

For a first position I'd recommend something where you're supported by furniture or the bed. That way you don't need to use your muscles to hold yourself up and you can really relax everything. Another positive (at least at the beginning) is that it's hard to get at your genitals (clit or penis)

WHAT???

Yes, I said hard to get at your genitals can be a good thing. Often when people are stimulated they tighten their anus, so at the beginning you shouldn't stimulate yourself. Later on in the session you can move to a different position and throw in some genital stim as well.

Doggie style works best for us. And we warm up by him fingering my ass.