Looking Ahead

After enduring his whining and whimpering for a full seven days, I told him last Friday that he was staying in his chastity belt for another week. If he had a tail, it would have been wagging happily. I mentioned my holiday plans for the upcoming Friday; we’ll finish our Christmas shopping together. As a reward for being good, I’m taking him along with me while he stays in his feminine role. The forecast predicts rain and cool temperatures here over those five days, so I advised him to choose an outfit that fits. If he behaves this week, he gets to wear what he picked; if not, well, tough luck. He’s already selected a red lamé catsuit paired with a black thong and corset, along with knee-high boots in black and a leather coat that hits three-quarters down his legs. It looks quite fashionable, so I hope they let him dress like that! I’m also planning for some serious bondage by Thursday night. My idea is to use an armbinder made of leather, plenty of straps, a posture collar, and a penis gag. We’ll keep everyone updated on how it all goes.