well I ended up with a 2" and yes.. cock first, then my balls. luv the feeling of them being popped thru the ring. also makes me really horny and I gain about 1/2 inch in length sometimes from being so horned up and full of blood..
If you're really donning that 2" ring cock first and then the balls you should be able to easily get into a smaller ring the right way, i.e. balls first and then the cock. And remember, the tighter the fit the more the cock ring will enhance your erection. Going cock first, followed by the balls, the ring has to be big enough to accommodate the flaccid shaft and one ball. But balls first, followed by cock, it only needs to be big enough to accommodate the flaccid shaft and the scrotal skin above the balls. If I put my flaccid dick in a 2" ring there's not even remotely enough room left to pop one of my balls through. But if I go balls first I can relatively easily get into a 2" ring, as illustrated in the attached pics.
I first pull enough scrotal skin through the ring to accommodate one of my balls and then gently press it through the ring. I then pull as much of the remaining scrotal skin through as I can to accommodate the second ball. In the first attachment here my right testicle has so little room left that it's trying to retract back up into my groin. But with a little pressure it will pop right through the ring where there's plenty of scrotum available to house it. Finally I work my dick head under the ring. As previously mentioned by enzia35 and zero_ga lube helps. But in this case I'm doing it dry because the Teflon is so slick that I don't need lube. Once my dick head has started through the ring I just gently rub it forward with my thumb until it's all the way through. At that point I can grab my dick head and balls with one hand and pull the ring(s) up the scrotal and shaft skin to snug up against my groin. To the uninitiated this process can seem somewhat gruesome, but it's really no trick at all. Removing the ring is just the reverse process, i.e. pull the ring forward along the scrotal and shaft skin far enough that you can push your cock head through into the shaft skin behind the ring, pull the rest of the shaft skin through until the ring is just hanging on your balls and then one at a time pop your balls to freedom.
Because a 2" solid ring is pretty tight for me to get on and off when I ordered a stainless steel ring I got the 2-1/8" i.d. That's still tight enough to function well but there will never be any doubt about my being able to get out of the thing. I'll have to disagree with vibrationzzz about having a small set of bolt cutters handy. If you can create enough room to safely use the bolt cutters you'll have no trouble getting out of the ring in a normal fashion. But if the ring is so tight that you can't get out of it you'll risk doing grave damage to your genitals by trying to use the bolt cutters. I suppose if you could slip a lubed up piece of bull hide under the ring it might be safe to use bolt cutters but I sure wouldn't try it. It's better to
know that the metal ring is large enough to remove easily. And, again, I highly recommend using the Teflon rings in various sizes to determine what size rigid ring is safe in that regard. With the Teflon it would only take a small pair of diagonal clippers to cut your way out. And that's a helluva lot safer than using bolt cutters.
I know such a novice question 
