Best caption wins! Go!
Tonight was a rare occasion. Sissy was allowed to come with Mommy on her date tonight.
Usually when Mommy went our her dates Sissy was locked up and restrained in bed in thick diapers. Sometimes if Mommy was going be a while there would even be a feeding gag. Tonight though Mommy wanted to show of her cute and submissive Sissy.
Mommy let sissy pick out a dress. She usually let him pick from 2 or 3 outfits. The whole time he was being dressed Momy made sure to tease him both verbally and physically.
When he was drrssed&and straining in his cage from the teasing, Mommy had him stand so she could take a few pictures. Sissy was getting better at posing but not had a bit of ways to come yet.
Alright lets get your diapers on now! said Mommy as she put down the camera. Ill make sure to take pictures of your finished outfit so we can post them when we get home. Everyone always loves your cute outfits.