I hope things go as you want them to. My wife used to be very shy about sex, but that changed for her after 26 years of being married together. She knows what she likes and enjoys and openly tells people I have a small, useless dick.
I also have the same issue with the extensions. I am not big enough and my balls are too tiny for them to hold or stay on. We have tried many different types with no success. She bought me a strap-on that my cock fits inside, but while it stays in place with the straps, I don't touch the sides of it. She gave it to me on my birthday in 2021 and said she wanted me to feel what it is like to have a "real cock."
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Are you hoping that your exploration into cuckolding will lead to you watching your wife enjoy a big cock?