I have experimented with anal masturbation since roughly one year, on average 2 to 3 times a month and I do enjoy it as a kind of "special treat" opposed to everyday normal masturbation. As I have gotten more curious and adventurous, I've tried out various silicone toys until I found the ones that really worked for me (which are the Tiger and the Magnum, both from FunFactory) and I also experimented with lubes.
This is where the trouble begins... I have few problems inserting the toys, but thrusting is nearly impossible without rubbing and pain or if I am lucky it just takes about two hours to "work it up" and even then I have to constantly reapply massive amounts of lube. While it is sometimes possible to enjoy it, all the work it takes is tedious and destroys much of the built-up tension/feeling.
Until now, I've tried three different water-based lubes, two silicone-based ones and one oil-based one. The water-based work fine all the time, but they are absorbed/consumed extremely quickly, so I have to add some more every 10 or 20 seconds of thrusting or else it will hurt pretty bad. The silicone ones didn't go well with the toys, were really hard to wash off and sort of sticky, so they are no alternative. Recently I bought the oil-based one from Yes, which has a pleasant smell, feels good afterwards and really lasts long, but the feeling is a bit sticky - OK for slow massage, but not really useful for fast and hard penetration. Oil and water in combination has all the advantages and drawbacks of water alone.
I couldn't find any helpful information on the net, I assume because the topic is only slowly leaving the taboo regions, at least on the majority of sites. So far I've had the following ideas for possible causes:
a) Fast thrusting doesn't work with silicone toys.
While I can't confirm or deny this myself, I've read numerous reviews which state that it is not a problem even with silicone (smooth one, to be precise).
b) I have tried the wrong lubes and there is yet a magic bottle of lube out there that will just work.
So far I tried Durex Play, Yes Water-based, FunFactory Toyfluid, Yes Oil-Based, Pjur and id Milennium (both silicone).
c) Not enough relaxation.
I use my fingers only to lube everything up and then switch right over to toys because I enjoy them more. I also tried with an orgasm before anal play, but that doesn't seem to make a difference. Insertion is always quick, easy and painless and slow motions are fine too, but everything else (that is, hard and fast thrusting for more than 10 seconds) just doesn't work like expected.
d) Hair... *eww*
Ok, this may sound a bit gross, but as I am a guy I have some hair down there. I've never shaved it because I like the pubic hair on the front and a shaved anus while everything else is hairy would look a bit weird to say the least... oh, and I also read terrible stories about the itching when all those hairs grow back. But as I tried everything else and nothing helped and considering that the majority of anally experienced people has few or no hair down there I assume that this must be be cause of my problems, although it doesn't really sound logical.
To sum all that up: what should I do? I really like the sensations of fast and hard anal thrusting (not just the feelings down there, but also the ideas and the "brain stuff" connected with it), it is heavenly and I would really like to have an easy, comfortable and efficient way of enjoying it. As so many people are having anal sex and enjoying anal masturbation, there must be a way to solve this problem... or at least I hope so. Any input and help is greatly appreciated!