I've been trying to get into prostate play for a few months except the most challenging part so far is just getting the thing in there. I have a set of the Doc Johnson mood naughty 1 plugs. The smallest is very easy to get in no matter what. The medium takes a little bit of warm up with my fingers and the small plug but goes in pretty well. The large one is a little challenging and takes around 10 minutes of the medium sized one being in there for it to be comfortable. Usually I play with the medium a little bit and hold the thickest part at my sphincter. I've read from previous posts that regular play is a good to way to get accustomed to larger sized toys. I've been using these plugs consistently for a 4 weeks where the longest time I hadn't used them is 3 days. Even then it's still very tight. Are there any suggestions for a way to make larger sized toys fit more easily? I use coconut oil for lube and always use an excess amount.

Thanks for your suggestions!