Well, this whole anal training thing did not go according to plan. Surprise, surprise right? They say that no plan ever survives contact with the enemy, and the plug is the apparent nemesis of my girl's asshole.
We've been stalled by the holidays, colds, back issues, and more. Still, patience is a must when working on any training. To that end, I've decided to just extend the timeline through this next school semester. My original hope was to fuck her in the ass by the time she had to go back, but at this point we haven't graduated up in plug size or had the planned enema. So, we'll just have to keep at it when we can find moments. This of course means that the girl will have to deal with wearing the plug through normal day activity, chores and the like, which would be a good thing in general.
I'm thinking of using the inflatable enema plug as an intermediary step between the two plugs. The inflatable aspect would allow me to stretch her inner colon incrementally over a short period. Regardless, we're still working on it and the ultimate goal is still anal sex. We're just going to go about it slower without a structured timetable. Also, I think that it would benefit her appreciation for the whole experience if I were to attack her clit with a vibe each time, forcing her to have at least one orgasm during the plugging.
Stay tuned :)...