Wouldn’t these look cute on you? They look cute on Jack!

Jack The Panty Boi

After his Masturbation Monday Marathon…and his ruined orgasm! – Jack woke up pretty horny Tuesday morning. Now, normally Jack is not a sissy. We’ve played sissy games before, and he does have this cute slutty outfit I like to put him in from time to time, but that was for another time. Of course, I thought that if he was going to be a horny, desperate bitch, I wanted him to feel like that all day – being my pantied submissive!

Putting Out The Panties

I sent him off to the shower, and told him I’d lay out his clothing for the day. He has this cute pair of sexy boy shorts. They look like a pair of cut-off Daisy Duke jean shorts – so slutty and sexy! They were laid out on the bed when he came naked out of the bathroom. His cock – no sissy clit on Jack! – started getting hard as he slid them up his legs and over his crotch. I gave it a little rub…and got a small wet spot in return! Then he put on some shorts and a t-shirt and off we went for the day to explore Cozumel!

Teasing My Panty Boi

I teased him all day, asking him how those panties felt against his skin, if knowing he was my panty boi was making him hard. A couple of times, he had to bend over to pick something up for me that I had “accidentally” dropped, and I’d quietly whisper to him, “I hope that shirt doesn’t ride up…everyone will see those cute panties you’re wearing!” His face was beet red the entire time – and he hadn’t gotten a sunburn- so it must have been the humiliation and embarrassment. Then, most embarrassing of all? When we got back that night, I rubbed his hard, throbbing cock through his panties and had him fill them with his jizz! And my, oh my, was there a lot for him to clean up….