Big Bottom Sissy Ass Was Too Tight! Stretched, Gaped and Opened by Mistress Jenna

As part of his regular anal training I love to fuck his ass with lots of different toys to keep that ass open and ready for a good pegging. Today he was particularly tight so I pumped loads of lube into his hole and gaped him open. I've already told this naughty sissy that I expect him to complete regular anal training so when we meet his ass is ready for bigger cocks. Clearly he had not been training as he was really tight. How do you think I should punish him? Let me know in comments and it might just happen if he doesn't improve his anal skills. A good sissy should be ready to open that ass any time the mistress requires it.