Anal tips - guy is LARGE.

Keleios

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I have found that the shape of the head is going to make a HUGE difference in the ease of entry. However, as others have said, your own comfort, arousal, and relaxation are the most important factors, and so is the application of something nice and slippery first. Lastly, a friend of mine swears by something called AnalEase, but I personally don't like the numbing sensation. if you can get it in without being totally numbed, it feels fantastic!

Thanks Altered!
He figured that the shape/size of the head made a big difference and he's certainly blessed there too. The initial entry has been the most difficult part for me to relax through so I'm hoping that if I put all the great advice I've been given here to good use and once I find the right lube, we'll be on our way to anal heaven.
I've amassed a collection of trial sizes for the most recommended lubes, don't think I've got AnalEase but I've got a couple that numb so they might come in useful for personal training purposes. For actually getting down to it though, I'd want to avoid numbing lubes as the guy in question already has the stamina of a robot bull and anything that could further delay the achievement of total pleasure probably wouldn't be a good idea.