Another oval ring question

I use the oval ring in my Jailbird and you are absolutely correct. The tightest ring that I can slip a fingertip under works great. It does hold my balls forward which makes sitting down a lot easier since I do not accidentally sit on my balls. Like you I was led to the oval ring after wearing the HT v.2. Been wearing my JB for years and it is comfortable with the oval ring.

 

Everyone is different - you need to find out if you are round or oval!
And more importantly, if you are oval, is the long axis from side to side, or from back to front?
If your shape is oval, then an oval ring orientated the wrong way, even if the correct dimensions, would be much more uncomfortable than a round one.

The penis isn't symmetrical, and even round ones aren't round:
http://ueu.co/wp-content/uploads/2014/09/loadBinaryCAKOVG7R.jpg

When I ordered my latest device, I opted for an oval ring, but I was very careful to measure myself multiple times before ordering.
To work out what would suit you best, then do the following measurements when both flaccid and erect, and I can't repeat often enough, measure multiple times, at different times of day.
You'll normally get a range of different measurements, you can either average them, or judge whether the tighter or looser end of the range would suit you best. If in doubt, do more measurements. To do it, just get two pencils and hold them parallel one each side of your member where the ring would sit, then use a ruler to measure the gap between. Do both for front to back and side to side. (or if you have the right tool, a vernier gauge, use that!)

In my case, I found that the critical measurement that caused pain if too tight was side to side. The front to back measurement was more important for the security of fit and the tendency of the cage to move. The other thing I discovered was that while the 'standard option' for an oval ring for my custom made device was with the oval long axis front to back, in my case I needed it going side to side. As it was a custom device, it only took a quick exchange of emails to establish the measurements I needed before the device was made. If you're getting a custom device made then the front-back and side-side measurements will be the ones needed by the maker. An oval ring will be based on a standard size circular ring, which will then be 'squashed' to make the oval, one axis dimension increasing the other decreasing. The average of the two dimensions will be nearly the same as the diameter of the starting circular ring, and a tolerance of one or two millimetres shouldn't make much difference to your fit.

 

I recently purchased MM's locking cock ring. I actually ordered two base rings, one round and one oval, so that I could test comfort, etc., before purchasing a jailbird later. It turns out the difference in dimensions on the oval is not that significant. The oval ring is shorter vertically (as one is wearing the ring) than horizontally. On a 2 inch ring, the vertical measurement is about 1/8 of an inch less and about the same addition horizontally. I assume this difference will be the same on smaller rings. I was comfortable enough in the round chastity devices so I haven't noticed much difference in the comfort level with the oval ring. The advantage from my perspective is that the slightly shorter vertical measurement reduces the bottom gap between the bottom of the penis ring and the base ring. This is important for keeping one's balls from popping through--or mine anyway. MM refers to this as added "security" in talking about the oval rings.

 

I have worn oval ring with my queens keep and now round ring with my watchful mistress, and
for me personally , the round ring is both more comfortable and more secure