Chapter 15.
Saturday. Bobby Tucker not happy. Woke late, and stayed in bed until his aunt came to see why he wasn’t up.
“Come on, Bobby. It’s your big day, today.”
“Aunt… I don’t feel well…”
“Let me feel…. Well you don’t have a fever.”
“My tummy’s hurting…”
“That’s because you’re excited about going to Sarah’s and dressing up in your maid’s outfit.”
“No it’s not!”
“Well everyone else is. So get up and have breakfast, quickly. I’ve made pancakes with honey and lemon juice. Don’t let them get cold.”
“Pancakes… Is there anything else to go on them…?”
“Well, only raspberries and ice-cream and chocolate sauce…”
“Okay,” he said, grumpily. “I’m coming. Don’t rush me.”
But he was downstairs and stuffing pancakes with two minutes.
Nicole had cleared the weekend. She had no appointments until Monday. She dressed casually – a black cotton top, black faux leather leggings and the obligatory thigh-boots – vinyl, not too high but enough to keep Bobby in line in case he became rebellious. After breakfast she took him out to buy wine and anything he felt like to eat or drink at Sarah’s. That quietened his objections and made it difficult for him to protest too much. They had a light lunch, and headed off about two-thirty.
Sarah had laid everything out on the bed in the spare bedroom. The spare things – pink panties, stockings and gloves – she popped in a drawer.
“Well, his outfit’s all ready, Lavvy. I just hope we can get him in it.”
“I’m sure Nicole will be able to persuade him.” There was a ring at the bell. “That’s probably them now.”
Sarah opened the door. “Hi Nicole…Bobby. Cheer up, sweetie….”
Bobby was hanging back, looking sulkily at the ground. He was about to make some sarcastic remark, but when he looked up at Sarah he did a double-take. Nicole had suggested that her friends should also dress “a bit sexy” for the occasion, to exploit Bobby’s vulnerabilities. Both Sarah and Lavinia were in their early thirties, and knew how to dress to kill. Sarah was wearing spike-heeled ankle boots, fishnets, and a little figure-hugging black latex dress she had borrowed from Nicole. Her black hair was combed back and pinned in a tight bun. She wore bright red lipstick, a spiked black leather collar, black leather bangles, and her nails were painted black.
“Hello, guys! You’re nice and early. Welcome!”
Bobby’s heart sank. It was impossible to defend himself against such a show of feminine power. His first sight of Lavinia was not reassuring, either. She had chosen a more traditional outfit, but one no less intimidating. She was sitting on the sofa, wearing her newest pair of beige riding breeches with a tan leather belt, blonde hair loose, a plain white shirt with rolled-up sleeves knotted above her waist, and tall, gleaming rubber riding-boots, moulded in the Spanish style with high tops, with little silver spurs. A riding whip and a pair of fine latex riding gloves lay on the coffee-table in front of her. She smiled a dangerous-looking smile.
“Nicole…Bobby…this is so exciting, isn’t it. Bobby – I should call you Bobbi with an ‘i’ now you’re going to be my maid, shouldn’t I? Bobbi then – your clever aunt has got you such a pretty uniform! I bet you can’t wait to see it – I certainly can’t.”
Bobby made a sour expression, but didn’t dare to protest. In any case, he was a little distracted by Lavinia’s riding-boots, trying to work out if they were really made of rubber, since he, something of a boot expert, had never seen any quite like that before – professional Spanish boots were normally made of leather. Lavinia registered his curiosity.
“Do you like my new boots, Bobby? I had them specially made. I somehow prefer rubber boots, don’t you?” She picked up her gloves and slipped them on. “Come and see – come on, don’t be shy!”
With the aid of an encouraging push from Nicole, Bobby approached Lavinia. She patted the sofa next to her.
“Sit with me for a moment.”
He sat, hesitantly, cheeks reddening.
“That’s better. Yes, these are classic Spanish riding boots. Rubber’s so nice and glossy, don’t you agree?
Without warning she threw one leg across Bobby’s lap, and waggled it about. He jumped in surprise, but she made sure to keep him pinned in his seat.
“Feel how nice and smooth they are. Go on!”
She raised her left knee a little so that her blunt spur dug into his flank. It felt like a threat, so he tentatively ran his fingers over the rubber. The scent of warm rubber filled his nostrils. He breathed deeply. He could feel his boyhood stiffening and his cheeks burning. His hands were trembling slightly.
“Don’t be nervous. Tell me what you think. Here…”
She shifted sideways and swung the other leg across his lap. He felt as if he was choking. He fought against his arousal. Lavinia straightened her left leg, and her boot descended on Bobby’s erection. Even through the thick rubber she could feel it pressing against her calf. She knew then that he was theirs to command.
“I think he’d better get changed, don’t you girls?”
“The sooner the better.”
“As he’s technically my maid, I’ll go with him and help.” She swung her legs back onto the floor and stood up. “Follow me, Bobby.” She took his hand and helped him up, then led him out of the room. Nicole and Sarah looked at each other as they heard their steps retreating upstairs.
“Looks like Lavinia’s taken charge,” remarked Sarah.
“Yes. He never had a chance, did he?”
Upstirs, Lavinia was implacable. She ordered Bobby to take off everything, turning her back to save his blushes.
“Now, panties on first, young man. I believe you know how to…arrange yourself.”
Reluctantly, Bobby pulled on the little panties. “Miss Lavinia… Why must I be a maid…?”
“Because.”
“Yes, but why? I mean I’m still doing my boot boy training.”
“You need to be versatile. Cleaning boots is one thing. But you need to learn how to serve ladies in other ways too. That’s why I asked if you could be my little maid this weekend. Don’t worry, I’m going to be a fair and caring mistress.”
“Will you?”
“Of course, darling. It’s not a punishment, you know. And you’ll be paid properly. And if you do a good job…”
“Yes?”
“You can be my boot boy too, and polish my lovely new boots. Would you like that?”
It was an attractive prospect. “Y-yes… If you want...”
“Good. Then we have a deal. Now, are those panties on properly?”
“Well…they’re different… They have another loop thing…”
“I know. Can you see where that goes?”
“Er…I’m not sure…”
“Shall I help?”
Without waiting for a reply, Lavinia turned round and walked up to him. He was standing holding open the front of his panties uncertainly. She didn’t hesitate.
“That’s it – hold them open while I attend to this.”
She reached down, and before he could move, took his erection in one cool gloved hands, and held open the upper loop with the other. In an instant she had slipped it over the shaft and let is snap firmly in place.
“There. Nice and neat just like a maid needs to be. Now, stockings next, I think…”
On went his stockings, the double-thickness tops gripping the tops of his thighs. Then the garter on his left leg, and his new shoes. As he stood there, balancing on his heels, Lavinia put his latex dress over his head, threaded through his arms and then his head, fastened on his cotton apron, his bell collar and his headband, and stood back to appraise him.
“You look gorgeous, Bobbi!” she exclaimed. “Now, put on your gloves. Pretty, aren’t they? Little hearts to match your stockings. Then before we let the others see you, I think a little makeup would be in order.”
Bobby was too overwhelmed to demur. In any case, the smell and feeling of the latex uniform was making him heady and a little dazed. She sat him down at the dressing table, and applied powder, a little mascara, peach lip gloss, and a little blusher to make his cheeks rosy like a cute little girl’s. Her proximity, her own scent, and the thrilling feeling of her touch on his face, induced a sort of euphoria, both mental and physical. He wondered vaguely how he could feel so happy all dressed up as a little maid, while at the same time the double grip on his erect pen-is was immersing him in a pool of sensual pleasure. He watched his face in the mirror, fascinated by his transformation from a sulky boy into a pretty, amiable little girl. Once she had done his makeup, Lavinia briefly removed his headband to brush his hair, then took his hand again.
“Shall we go and show the others? They’re going to gobsmacked, Bobbi!”
Any reluctance he had felt has evaporated. He jumped up – and gasped.
“Are you all right?”
“Oh…no, it’s nothing…”
The sudden movement had had the effect of tightening the second loop. He could feel it gripping the shaft just beneath the bulging head. It wasn’t uncomfortable, but he realised that now his erection was going to be permanent. And as he followed Lavinia to the door and along the corridor, he also discovered that at every step, it shifted provocatively back and forth against his tummy. He took little steps, but even then it was being cheekily twitched at every stride.
They stopped at the top of the stairs.
“Girls? Are you ready? Bobbi the maid is coming down to show you her uniform.”
“We’re ready, darling! Send her down!” Sarah called back.