To answer the easy questions first:

Cockrings work to help keep a penis harder longer (and can also make it a bit thicker and more defined, depending) because they trap blood already accumulated in the penis, slowing down the reverse flow OUT of the penis. They should NOT restrict blood flow TOO much, just ENOUGH to give that extra "boost" to your dick's firmness, size and shape.

This answers your question about why some dicks are cold in cockrings: these guys are wearing them a bit too tightly, or for too long. However, it is not unusual or unexpected for even a properly fitted cockring to make a penis a little bit cooler to the touch. After all, the blood in there has been hanging around for a bit longer than it might otherwise normally remain, and the proximity of the blood to the surface of the skin cools it off. More or less, anyway...

They aren't harmful, provided you use them correctly and don't make them too tight as discussed above. If your penis feels TOO cold or starts to look blue or purple in color, you've got it on too tightly. Adjustable cockrings are good for newbies; you can use the snaps or Velcro or whatever fastening device to make it more loose or more tight, depending on what you need and what is comfortable. Steel rings can't change their size, obviously. You'd need to probably purchase a "variety pack" of different sizes (easy to find) so you can pick the one that is closest to what you need. You can certainly buy a single ring, but if you don't know what size will fit you, you clearly can't return it.

You can find out your size for a steel ring by either using an adjustable ring and then measuring the length and/or diameter of it, or simply wrap a piece of string around your dick and balls, mark where it meets, then measure that length and/or diameter. I once did this, taking the string to an ABS and surreptitiously holding it up to a steel ring in a package and seeing if it circled the ring at the right size.

I've never heard of cockring addiction, though I suppose anyone can take just about any toy or sexual preference or whatever and make it a habitual part of their sexual regimen. Just guessing here, but maybe it is possible to wear cockrings incorrectly and too tightly for too long and cause a bit of damage to erectile tissues, though this doesn't seem to be anything I've ever heard discussed before. I'd think if there's any sort of "addiction" involved, it would be psychological more than anything else, but this is also not anything I've heard discussed too often. I think guys who enjoy cockrings simply use them because it feels good...

The more difficult question you asked was about why it is that you don't stay hard when a guy asks you to fuck him. It's impossible to answer that in detail, since you didn't provide a lot of information. I think it is pretty safe to say that there is some psychological reason why, as opposed to any sort of physical problem. Since you get hard normally at other times, it isn't your dick that is faulty.

Are you placing a condom over your penis before attempting anal sex? I hope so. Sadly, however, a condom is an erection-killer for a lot of guys. This does NOT mean you should NOT use one -- it's just a possible explanation. Despite what others may tell you, you are not REQUIRED to fuck anyone if you can't keep it hard in a condom. Maybe you just aren't ready to fuck anyone right now. So wait. Practice masturbating while wearing a condom -- this could get you used to the feel of it.

Sometimes, men feel threatened by a condom, too. You have to get it on in time before you lose your erection. Anyone remember George Costanza whining about this, saying: "It's like 'Beat The Clock?'" If you lose your erection before you can get a condom on, just stop, mess around some more, get hard again, and try later. If a partner isn't willing to wait and accommodate that, he's an asshole and not worth your time, if you ask me.

Are you nervous about the REAL dangers of anal sex? Does the thought of STDs make you lose your erection? If so, once again, perhaps you are just not ready at this time. No big deal. No need to rush into it, especially if you would be putting yourself at risk.

Is it simply performance anxiety? Are you concerned that you might not be able to satisfy yourself and the guy who wants to get fucked? Again, why rush it? Find an understanding partner and establish at least a modicum of TRUST. This does NOT mean that having trust in someone is an excuse to NOT wear a condom, it just means that if you are more comfortable with someone, and more relaxed, maybe things will work out for you in time.

Maybe it's just a vicious circle -- it has happened a few times already, so now you just EXPECT it to happen again. So it does.

I think that deep down you have a pretty good idea of exactly WHAT is going on in your head when this happens to you, but you didn't share it with us. Just reflect upon what goes through your mind when this happens, or just before it happens. That should provide your answer.

Bottom line is that MAYBE a cockring would help, but I think it is much more important for you to get at the root of the problem and STILL have safer sex, using a condom. Additionally, keep in mind that the first few times you try out a cockring you might find the increased sensation to be so great that you cum quicker. You should practice through masturbation for a while first. Also, if you wear a cockring TOO long, you can go limp. Your penis NEEDS blood to circulate freely. Restricting it TOO much isn't wise. You may also LOSE sensation if you wear it much too long.

If I have a guy sucking me off for hours and hours, I always take a needed break and at that time I will remove the cockring. Some guys are nice enough to massage my dick and balls and let me relax when I do this.

And if it helps at all, when a guy begs me to fuck him, I also lose my erection pretty fast. For me, this is because I know I will NOT do it -- and I feel guilty that I can't give him what he wants. Yet the IDEA of fucking a guy that I LOVE turns me on a lot -- but not a stranger. This is why I make sure everyone knows in advance that they will NOT get fucked. Yet even so, even with advance warning, some guys don't care and they will STILL beg for it. This not only turns me off, it gets me pissed, too. Then we have to stop whatever we are doing and I have to tell him AGAIN that it isn't going to happen. Really puts a damper on things, you know?

If you care to share more of your inner thoughts and feelings as to what is going through your mind when you are put into this position of getting ready to fuck a guy and can't do it, I think it would be beneficial, even if just for you to type it out and be honest with yourself.

Good luck.

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