“So sweetie”, Jake’s mother sat him down, “there will be hundreds of people at the show this weekend. Do you want them to know that you are a boy in your Lolita dresses or would you prefer if they thought you were a girl?” Jake swallowed hard. He didn’t want hundreds of people to know that he was a boy in petticoats and tights and frilly bloomers. Presumably there would be lots of photos taken and videos and maybe thousands of people would know by the end of it all.
“I don’t want people to know I’m a boy but I don’t know that I can act convincingly like a girl”, he eventually responded. “That’s ok honey. That’s why I’m keeping you in dresses this week and we can train you to walk and talk like a girl. We only have a few days so it will have to be intensive. You must walk and talk like a girl all the time – all day long – no faltering – otherwise you might slip up at the weekend and everyone will know.”
Jake sighed. Had he just talked himself into being trained intensively to be a convincing girl? What was the alternative? His bedroom was locked off limits. He had no boy’s clothes to wear. His mother had already altered two of the dresses to fit him perfectly so there seemed to be no going back.
His mother took his dejected silence as a ‘yes’. “So starting now”, she opened the dividing doors between the dining room and sitting room. “You can practice your cat walk.” Jake stood up and smoothed his petticoats down. He walked to one end of the room, turned and braced himself to walk the length of the two rooms convincingly as a girl.
His mother coached him, telling him how to hold his hands out daintily as he walked. She encouraged him to turn quickly at the end. “But then the petticoats swirl up and show more bloomers!” he protested. “Well duh!” was his mother’s response. “That’s what we want!” Jake cringed.
When his basic walk was somewhat satisfactory, she gave him the pink heart-shaped handbag and the cuddly bunny to hold. She tied his pink bonnet on and fiddled with the ringlets that poked beneath it until they rested prettily on the lace collar of his dress. She coached him to turn his head this way and that as he modelled so everyone could get the benefit of his pretty bonnet.
Jake was already getting tired walking in the pink high-heeled sandals but she wanted him to walk back and forth repeatedly, insisting that he wasn’t quite there yet. The phone rang. “Now keep it up!” she told him as she went to answer it.
Jake sighed heavily. He prepared himself at the dining room window end and minced along the carpet, clutching his handbag and bunny. He turned his head from side to side, imagining an audience admiring the lace on his bonnet. That made him cringe but he’d reached the other end so he swung around making his petticoats swirl and revealing several inches of his bloomers.
He heard laughter. He looked up and saw four boys looking in the dining room window, shielding their eyes against the daylight. “It is Jake!” “He must be wearing sissy dresses all the time!” “Wow did you see his frilly knickers!”
Jake desperately tried to push his petticoats down. He looked frustratedly at the pink handbag and cuddly bunny he had been holding and became acutely embarrassed at the lace of his bonnet framing his view of the boys staring in the window at him. He wanted to die, again!
His mother returned from answering the phone, her back to the window. “Why have you stopped?” The boys disappeared from the window and he could just about hear their laughter as they ran off. Jake couldn’t bring himself to say what happened he was so mortified. He just resumed on his cat walk.
Diane happily joined in on his training. She jumped on any slight faltering in his acting like a girl. Despite his best efforts, he couldn’t keep it up all the time. It was just so awful, having to flounce around like a girl.
His mother grew frustrated with progress. “We need to do something more to make this work.” “I think he should be spanked when he lapses”, Diane suggested, not entirely seriously but enjoying the image. Jake looked at her aghast. That only convinced his mother that it was a good idea. “Yes, that’s it. Any further mistakes and I’ll pull up your petticoats and spank you! Now practice your walk again.”
Jake did as he was told and was trying to figure out if it was an idle threat or not. He walked back and forth several times. “Place one foot directly in front of the other”, Diane told him in a raised voice. Jake swung around “I’m trying my best!” Diane smiled at him and looked to her mother.
“Right, that’s it!” She went over to him and took him by the arm. She made him bend over the dining table. “No mum!” She pulled up his petticoats and quickly started spanking him with her bare hand. It was pretty ineffectual but Jake was still mortified bending over there with his petticoats over his back and his bloomers on full view to the room.
He was surprised when Diane left the room. He’d have thought she would want to savour this. But she returned with a wooden spoon. “Ah good!” her mother thanked her, having been dissatisfied with the lack of effect of her hand. “Ow!” Jake protested with the first slap of the spoon on his bottom. “That’s better!” his mother was happier now with the effect.
After six slaps with the spoon she took her hand off Jake’s back and he was able to straighten up and push his petticoats down. He was sniffling. The pain wasn’t too bad but he was so humiliated.
“Now try again!” his mother ordered. Jake quickly walked down the room, placing each high-heeled foot perfectly in front of the other. “Now we are getting somewhere”, his mother smiled as she gripped the wooden spoon determinedly.
� Betty Pearl's Sissy Stories 20.1
Topic: A Model Son (Read 102577 times)
