If you are new to pegging and are looking at the variety of strapons and dildos out there and wondering which one is right for you, below is a guide to help you get started:

Beginner:
Generally if you are first starting out with assplay than I would recommend something in the range of .75" to 1.25".  This puts you in the range of around the size of a large finger.  Click on the images below to see some examples.

Intermediate:
Once you decide pegging is for you and you have no problems taking the beginner dildo than it's time to branch out.  This puts you in the 1.5" - 2" range.

Pro: 
For those of you who can take intermediate sizes with ease and enjoy pegging or assplay on a regular basis, you my want to explore some wider and longer dildos.  Generally anything larger than 2" + is a great accomplishment.  By this stage you know how to prep your ass and have the patience it takes to dilate your ass for larger insertions.
 
 
Question 
We are kind of new at pegging. He loves the pain he feels the next day when he sits. First is this normal? We started with 1.5" diameter, then 1.75" diameter, now its over 2"s in diameter, so that his asshole hurts. How thick is to thick? Thanks

Answer
Congrats on delving into this wonderful new kink!  It sounds like you guys are doing it right…gradually working him up to a bigger size.  What he may be describing as pain could actually just be that twinge we all feel the next day after a vigorous ass fuck.  If you’ve never experienced it then I suggest you do too so you know exactly what he is describing.  :)  As far as what is too thick?  Well we all have our limits.  For some it’s 1″ and for others its larger than a fist.  The anus is wonderfully expansive with the right prep work, arousal and lube!  Many men crave bigger; they love the fullness that comes with larger dildos.  That being said anal sex should never result in true pain during or the next day…or it’s being done wrong.  I’d definitely get him to describe what he is feeling.  If it’s more than a twinge, i.e burning, bleeding, sharp twinges or raw tenderness then you need to back off the bigger toys until his ass is properly opened.  See below for how to do that! 

http://eroticpegging.com/1/post/2015/01/pain.html