So we tried again with the smooth side, but she said it still wasn't comfortable, mainly she thinks she doesn't like the silicone. She doesn't get real wet anyway, but when she is just doing it for me (or trying something out) it takes more lube. Even back when we used condoms she said that if it went on too long it got uncomfortable. She said not to completely discount it, we'll try again when she is more into it. I was glad to hear that. She didn't seem to have any trouble at all with the girth, which kind of surprised me. When she is into more and more naturally wet, that should help.
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