Frank was scrubbing behind the toilet bowl in the furthest bathroom when he was summoned by a bell from the sitting room. He sighed as he pulled off the rubber gloves and replaced them with his lacey white mittens.
They were all laughing as he tottered in before them in his pink maid’s uniform and ballet boots and curtsied. “So it was Angela’s idea to get him into the junior bridesmaid dress?” Mrs Polstead asked. “Yes, and she fixed it so it was so short he kept exposing his frilly panties.” They all laughed. “We have all the photos now. You should see him smiling awkwardly in his pink dress and cute white tights clutching his basket of flower petals!”
Frank was mortified as he stood on enforced tippy-toes in front of them. “And then we used the excuse of the acrylic nails to get him to go to the convent in a gymslip!” “He had no idea that they could be filed down and the pink colour removed”, Angela giggled. Frank wanted to cry.
“Where did auntie get that old fashioned tennis dress with the frilly knickers?” Angela asked her mother. “She found it at a jumble sale – same with the pink tutu.” His mother was laughing out loud now. “He totally believed that they had been her daughter’s!”
“When Mother Superior was told he was actually a boy, she was only too happy for us to keep him in the short gymslip”, Angela added. “And give him bigger boobs”, her mother recalled. “Yes it meant all the boys were ogling his long legs in those tan tights and his big chest in the push up bra instead of the real girls.”
“Madame Bouquet had great fun keeping him back for the extra ballet ballet lesson and then making him late for the bus so he had to go home in his pink tutu and pink tights!” They were barely able to talk now they were laughing so much. Frank could do nothing except stand uncomfortably in his ballet boots and listen to it. “I bet you are grateful for those ballet lessons now though”, Angela tittered, looking at the padlocks on his pink boots.
“It was actually Mother Superior’s idea to make him a cheerleader and give him the frilliest and shortest uniform of them all. She loved the idea of all the boys in town unknowingly ogling another boy dressed up in big boobs and short petticoats. If only they knew!” His mother put her hand to her chest to try to control her laughter.
“Remember him in his coc-ktail dress?” Angela recalled. “Oh yes! In those five-inch heels he couldn’t get away from the line of boys wanting to dance with him.” Frank could only WISH he was able to wear five-inch heels now, as he wobbled a little in his ballet boots. “It took me ages to find those stockings for him with the bright silver seams so everyone would know he was wearing stockings.” “Well I think everyone could see anyway when he was up on the stage. It was not surprising that all the boys wanted to dance with him.”
They settled down a little. His mother looked at him. “It took a while for him to realise that everything he did to resist only made the situation worse.” “I think it was in the new year that he finally seemed to accept that we were in total control”, Angela added. “Yes. Do you remember taking him to the park in his sissy pinafored dress?” “That’s right! I can still see him skipping along holding the big pink lollipop! Was that the first time we did his hair in pigtails?”
“He really couldn’t decide whether he wanted to be a sissy little girl or a perfectly formed maid”, Mrs Polstead observed. “As if it was ever going to be his choice!” Angela laughed.
His mother stood up and walked around Frank. “So do you like your pink maid’s uniform?” Frank curtsied. “Yes mother.” “You are too afraid to say otherwise aren’t you?” Frank wasn’t sure how to respond to that. There was a pause before he curtsied and decided the safest thing to say was “Yes mother.” “Because we can still make things worse for you, can’t we?” Frank wondered what could be worse than being trussed up in a tight corset, pink lacey stockings and suspenders and ballet boots locked on, wearing a short pink petticoated maid’s uniform, frilly apron and pink pettipants. But he didn’t doubt that they could find some way. He curtsied. “Yes mother.”
“So why don’t you politely ask Mrs Polstead to let you wear your pink uniform and ballet boots every day from now on?” Frank knew that this was going to happen anyway. He curtsied, holding the position with his petticoats held out while he said “Please Mrs Polstead may I wear this uniform and the ballet boots every day from now on.” She just gave him a questioning look. “And the corset, pink stockings and pink pettipants?”
Frank sighed. He curtsied again, just barely able to hold the curtsey while he uttered “Please Mrs Polstead may I wear this pink uniform with the petticoats, the corset, pink stockings and suspenders, the pink pettipants and ballet boots every day from now on.” “Well seeing as you asked so nicely, yes!” They all laughed.
“Now fetch a bottle of champagne from the kitchen and three glasses before you get back to cleaning the toilets.” Frank curtsied. “Yes Madam.” Frank tottered off to his future.
THE END
Many thanks for all the comments. Hope you enjoyed it :)
Betty Pearl's Sissy Stories 20.1
Topic: Got the measure of him (Read 28064 times)
