I had a similar issue start up in March, related (I think) to switching to a Selle Anatomica saddle. I loved this saddle - it really felt like it "disappeared", and I was very hopeful that I had finally reached the end of my saddle woes. But, after about 10 or 15 miles, I would start to feel pressure in the tail bone area when on the saddle, and severe pain when rising up off the saddle. After rides of more than 25 miles, the pain can last for a day or two, and is most noticeable when standing up after sitting down. (I'm still sore today after a 27 mile ride yesterday)
I did some research here on TE and on other sites and the consensus is that the tail bone pain can come from having a saddle that is too narrow (or from an injury, like a fall).
There are several threads here that discuss it - here's one:
http://forums.teamestrogen.com/showthread.php?t=15575 (See Thorn's comments specifically)
If you haven't had a fall, maybe your saddles are too narrow? Have you had your sit bones measured?
I went to a bike store this morning to get my sitbones measured on one of these Specialized butt-o-meters, and I found out that my sit bones are actually pretty narrow (120mm, more or less). Since the Selle Anatomica is a fairly wide saddle, I think the issue for me is the flexibility of the saddle, not the actual width. For instance, even if the saddle is pretty wide from side to side, if it slopes down to the sides, it will be effectively a more narrow saddle.
The guy at the LBS today told me that sometimes tail bone pain can be from position on the saddle as well of the position of the saddle. This makes sense to me to as a possible cause and/or contributor as well, so armed with a new saddle (Avocet 02 - flatter and wider at the back) and more attention to body position, I'm going to see if I can't get it corrected.
Good luck - it is a very uncomfortable problem to have!



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