Is there a best sex position for trying anal for the first time? Some say no, but that there are two that seem to feel better than any others, especially for first timers.
The first is the Doggy Position, with the receiver on all fours, and the giver thrusting from behind. This position works well for your first time because it allows the receiver to back onto the penis at her own pace. If it starts to hurt, she can stop for a second and allow the anus to relax some and accommodate it at her own pace. And, if it starts to become uncomfortable for the guy, he too can back up a little bit.
The other position is the spooning position. This works very similarly to the doggy position, but because of the angle, it’s a little more relaxed. That’s key for a first-time experience, keeping her relaxed, and for this reason, spooning is probably the best position to start.
Some people will recommend using the standard missionary position or a variation of it for your first time. I disagree with this because of the awkwardness of trying to get it in when you’re doing it for the first time. You want to make sure the first time is as easy as possible, right? That way, if things go well, you’ll want to do it again.
Whichever position you try first, you definitely will need A LOT of lubricant, and I suggest spending a good amount of time on foreplay.
An ass plug or a small vibrator are a great way to begin “feeling out” this area. Just stay relaxed, lubed and experiment when your sex drive is at its peak.