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 hurt for the guy, he, too, can back up a little bit.
The other position is the spooning position on the bed. This works very similarly to the doggy position, but with the added friction of the bed (since the body is pretty much in full contact with the bed), it becomes a little harder to manipulate your body as gingerly as you can in the doggy position.
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 angles involved in achieving penetration and the relative awkwardness of trying to get it in when you’re doing it for the first time. You wan to make sure the first time is as easy as possible so ensure that things go well, and 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 plugs 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.