Today was the first day of jenpet's imposed anal training. Having anything inserted into her asshole, indeed just having her asshole as the focus of sexual interest, makes her clam up instantly. Thus, I expected a fair amount of resistance when I told her it was time.
she pouted, whined, dragged her feet, and was even openly argumentative. But I expected that and we managed to work through it. It being the first time in a long while, I went slow, used lots of lube, and eased the small plug into her ass. There was a lot of sharp intakes of breath, moaning, cringing, but she didn't openly fight it by kicking or clenching down on the plug. I was proud of her for that.
Now the training itself that I have in mind calls for her to be caged for an hour, locked away and drifting in that mindlessness that she so often finds to help her deal with the plugging. Shackles on her wrist and padlocked to the side of the cage to keep her from futzing with it. However, it being the first time, and there needing to be a lot of communication to keep her calm; I decided to leave her on the bed, covered with a comfy blanket, and a vibrator buzzing away at her clit. I also allowed her to have her hands free. I laid next to her, talking her through, asking questions at her discomfort, bringing her mind to where she needed it. I rubbed her breasts, massaging and watching as her pupils dilated, her lips parted, her breath rose.
I let her cum, twice on that side while I rubbed her left breast and once more on the other side while I rubbed her right breast. I made her think about the plug still in her ass, like a splinter of my intent. Finally, I took the plug out of her and fucked her saturated cunt, reminding her of why she was so wet. I made her thank me for the experience while she came again.
Then, I asked her how she was and she said she was none the worse for wear. There was, of course, the ache left behind by the small intruder, but she was otherwise fine. Then I reminded her that this will happen every day till she went back to school. Suddenly, she was less okay. I smiled and let her shower, eagerly awaiting tomorrow...