Even though it was nothing to do with poor sissy Jamie, that his Mistress' delivery had been delayed, Jamie knew his Mistress' view was that someone had to punished for any mishaps, even if they were totally innocent.

deviantart.com/sarahch677/art/CEO-to-Secretary-1339036703

deviantart.com/alice-albert/art/The-soldier-and-her-sissy-1333048189

Such a simple scene can bring so much joy to so ma y sissies.

They used to be happily married but their relationship had become boring for her in recent years. So she decided to spice things up a bit. A perfectly reasonable solution to a stale marriage. Don't you agree?

With a very long weekend ahead what further humiliation is in store other than being paraded through the mall? Don’t let that pouting face fool you Sissy’s panties are tight and slippery wet. She is likely to wager foolishly again every Wednesday just to see how degrading her friends imagination can get weekend after weekend.

21-year-old Gemma had always been the domineering one out of her and her older brother James. Their mother had allowed this dynamic to develop over the years, and she often used to smile as she heard Gemma bossing him around. Usually it was harmless things like fetching her a drink or tidying her room. But recently she had noticed she had him doing more intimate things, like being Gemma's footstool and acting as a stool on his hands and knees while she did her makeup. Gemma even had him clean her shoes with his tongue, right in front her. She was planning to have a word with her, and say things had gone far enough, but that night she arrived home to find Gemma berating James in the kitchen. And this time he was dressed in a pink maids outfit. Taken aback, she watched the scene unfold and allowed things to play out, as she thought James looked adorable in his sissy dress. She might join her daughter in bossing him around, and having a maid would be a godsend.

After observing the telling off Gemma gave James, their mother watched James hurriedly finishing the floor, then dutifuly reporting to Gemma in the living room. Gone were her concerns about Gemma taking things too far, replaced now by intrigue. She was fascinated watching her son, wearing a pink sissy dress being totally dominated by his younger sister, and now rushing off for what will undoubtedly a severe telling off. Possibly more. She didn't have to wait long to hear the muffled voice of her daughter,berating and chastising her son. Then to her surprise, it went quiet. But only for a minute, she then heard the unmistakable sounds of a hard spanking. After about 15 minutes it went quiet again, only hearing the odd muffled comment from Gemma. Just then the door to the living room opened they both emerged. James now red faced with tears still in his eyes after the spanking. Now with a gag to ensure his silence.

And that was a perfect fit too

I would love to be dressed like that in pink frillies surrounded by butch girls in jeans.

With apologies to prissy!