I am currently looking to increase the size of my anal toys.
The largest I currently use is the Titanmen No4 anal tool http://www.lovehoney.co.uk/product.cfm?p=25813 it is 8" at its widest point and it is no longer a stretch.
I am unsure whether to get the Titanmen Intimidator http://www.lovehoney.co.uk/product.cfm?p=17540 or the Titanmen Ass servant http://www.lovehoney.co.uk/product.cfm?p=17541
If anyone has expereince of either of these it would be appreciated.
Either of these would feel great and help stretch you: but neither will give you the feeling you get when something's all the way in (until you get to 12 inch toys, which I'm guessing will be a while). It's one thing being stretched and another feeling the current challenge getting nearer and becoming easier.
I've been at the same place as you, the titanmen no4 was a favourite for a good year, and I still use it occasionally, when I want to wear a plug all day.
I recommend getting whichever of these you pefer as a stetcher / warm up, unless you already have similar (tapered), and also get a plug with a 9 inch maximum that will nearly fit (on a good day).
The move from 8 to 9 inch toys is a lot easier than the move from 9 to 10. (At least it was for me).
Take your time and enjoy the process as well as the progress x
The intimidator or this http://www.lovehoney.co.uk/product.cfm?p=7234 would be my choice, the first has a nice long slow taper which is good for progress but is long so may cause issues, the two shots starts smallish and goes nice and large and has a very good base.
The ass servant is huge compared to no4 anal tool. It's about 3.5 inches bigger in circumference. If you've got average sized hands, make a "O" with your thumbs and index fingers and you have an idea of what you are facing. I've had the servant for several years and it's not very good for stretching from (no offense) beginner size. It would be a bit like sitting on a stool, pushing more than expanding.
I've heard that the Intimidator can be a bit long for comfort. I think that if I get one I'd cut it down a bit. Chop the first three off.
I see you have the perfect fit medium I have the large and I love it. Have you tried laying with your bum in the air and putting ice cubes in. It's so cool. Pardon the pun ;) butt again pardon the pun it feels awesome