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Cock Rings of any sorts
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Messaggio Cock Rings of any sorts 
I've tried many of the 'through the mail' types and found most to be wholly inadequate, painful, cheap and/or useless. The only one that I really like is the Rocks-off Figure Eight.
Most of the 'rings' are made of cheap, soft, elastic material and most, in my experience aren't good for more than a couple of uses. Then they break. And if they 'snap' when they break...ohhhh, damn, do they hurt.
Others are too 'thin' and cut into me unmercifully. On top of that they are often very difficult to 'dig under' to pull them off - and that hurts.
In my experience, the 'noose,' or 'tubing and slip-tie' type usually pinch really hard at the pinch point on them.
In my opinion, anyone who would put a metal ring on themselves is insane. After you 'trap all the blood out there' and everything is too big to get back out, there's no way to 'loosen it' to get it off.
My Rocks-off is just big enough, just tight enough, just soft and pliable enough to put on, stay comfortable, and do the job. I've got three now - one in the headboard at home, one at the cabin and one in my travel bag - and my oldest one is at least three fault-free, regularly used years old.
If anyone can point me toward another, equal or better product, I'm willing and anxious to try it. I want the best experience I can get.

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I want to get my roommate a nice prostate massager/stimulator something like this [url=https://top10sextoys.com/toys-for-men/]https://top10sextoys.com/toys-for-men/[/url] or some other kind of anal toy for his birthday. His birthday isn't until spring, but I want to have a toy picked out so I can save up for one and order early.

Anyway, although I myself enjoy anal, I know nothing about the specs for anal toys, especially not anal toys for men. He's never had a toy before, but he does enjoy anal, so he's a beginner to toys, but not a beginner overall.

What kind of specs should I be looking for? Also, if anyone has any toy recommendations with a max price tag of $40, the help would be greatly appreciated.

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