Shorts do wear out. I recently had a similar problem. My tried and true terry t-shorts were starting to chafe. I think the foam of the chamois was so compressed it just didn't give me enough cushioning. I replaced them with the shebeest triple S short that I really like the chamois on, and I am waiting to try their longer elite touring short. If you didn't replace your shorts as you slimmed down that could also be the problem if it is bunching under you. Also, as others mentioned, you may find a high performance saddle more comfy than a so-called comfort saddle, because it will give firm support to your sit bones. I have used a terry butterfly for years. It is also important that the saddle be positioned correctly on the rails, so it really is supporting your sit bones and not soft tissues. It can take ~100 miles to break in a good leather saddle, so you may have to be patient. I also love chamois butter for long rides. Another issue, if you are perimenopausal, is that you may need to start using a vaginal estrogen cream. Another thought, maybe you have outgrown your comfort bike. As you start to do longer distances, you may prefer a less upright position to take some weight off your bottom.



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