Lady Connie Ch. 02

At last, he stood up and smiled, sketching a little bow to the Lady.

'Thank you, dear boy,' she said, and air-kissed his sticky cheek.

'Don't forget to dress up for dinner.'

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JIM stood in front of the Lady's boudoir, hesitating for a moment before knocking. He'd only been locked in the chastity device for two days, and it already felt like agony. His poor, confused cock constantly strained to harden, only to be thwarted by rigid plastic, and his balls felt like they weighed ten pounds each.

He took a deep breath, steeling himself for more torment. Sure enough, Randi was there, still topless, the teasing clamps dangling from her erect nipples.

Candy took up the hairbrush and positioned herself behind the Lady, nonchalantly brushing her hair as the scene unfolded.

'Dear boy,' Lady Connie said tenderly. 'Poor Randi has been wearing those decorations all day. I'm certain she would appreciate it if you took them off and soothed her aching breasts with some kisses.'

Randi shuddered and looked at him, her eyes nearly glazed with need.

'Yes ma'am,' Jim said, and moved to where the upstairs maid was standing.

Gently, he opened the clamp on her right breast and replaced it with his lips. He licked and suckled softly as the girl whined with pleasure.

After a few moments, he moved to her other breast. He felt her hands on his head as he stroked the throbbing nipple with the flat of his tongue, drawing it deeply into his mouth.

'Hands behind your head pet,' the Lady chastised mildly, and Randi whimpered softly, lacing her fingers at the nape of her neck. The position caused her to stick her fabulous tits out even further for Jim to suck.

He slid a hand between her legs, ready to make the girl cum, but that wasn't part of the Lady's plan either.

'Please don't touch her with your hands dear boy,' she instructed, her voice soft but firm. 'I'm certain you can bring her to a climax solely by pleasuring her breasts.'

Randi let out a tiny moan of frustration and lust, and Jim let his arms dangle at his sides as his mouth roamed over her huge boobs. His tongue fluttered and swirled over each nipple in turn, his own discomfort and frustration forgotten as he concentrated on her pleasure.

Randi panted and moaned, her body shivering, and as her hips started to twitch Jim began to very carefully use his teeth, nibbling and scraping them on her sensitive, hyper-stimulated nipples.

Finally, the girl released a huge, shuddering sigh of bliss. Her knees gave out, and she sat back heavily on the bed. Candy giggled softly as she bounced.

'Ohhhh, fuck,' Randi gasped, 'that's such a cruel way to cum. It's so damn sloooow!'

Lady Connie smiled, her eyes sparkling with amusement.

'But you love it, don't you my pet?'

Randi looked at her adoringly.

'You know I do, my Lady,' she said in a husky voice. She stood on lightly trembling legs and bent to kiss the Lady's cheek, whispering 'thank you.'

Lady Connie stroked her hair with affection. 'Good night sweet one,' she murmured.

Jim leaned down to kiss the Lady's cheek as well, but she pressed her palm softly against his face, catching his eyes with her gaze.

'Just try to remember, my dear boy,' she said gently. 'Your torment, your suffering-they don't matter. The only thing that truly matters is that I'm pleased.'

Her words calmed and soothed him, and he finished the good night ritual, his heart filled with admiration for this wonderful lady.

'Good night ma'am.'

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HIS dreams that night were filled with wild, erotic visions of all the things he had done to, and with, the maids since working for Lady Connie, and he woke up panting, his balls throbbing, his cock fighting and failing to stiffen.

Jim took a cool, almost cold shower, and after getting dressed paced around his room, taking deep breaths, trying to steel himself for the day's torments.

It was a rainy, grey day outside, so he and William would be inside helping the maids. At the morning gathering, Lady Connie announced that the day's uniforms for the girls would be 'stockings variation,' and both Mandy and Randi looked at him and giggled.

Jim was treated/teased by another erotic show-Mandy giving William a blowjob that left him weak in the knees-and then after breakfast, when he went to help the downstairs maid with her chores, he discovered what the stockings variation meant and why the girls had giggled.

She was wearing a pair of sky-high stripper platform heels, mostly clear with just a touch of pink, and pink thigh high stockings-and nothing else.

The soft pink made a luscious contrast against her cocoa skin, and the sight made him want to fall to his knees and either worship her lovely body or beg for relief-or maybe both.

Mandy gave him an apologetic smile. 'I know it's rough being teased like this, but these are the Lady's orders.'

He smiled back weakly and kissed the top of her head.

'I don't hold it against you.'

She giggled again. 'You can't!' she joked.

The teasing, however, was constant. It wasn't just her nudity. The maid took every opportunity to bend over, to show off, to flaunt her prime assets for him.

And as Jim bit back helpless groans of need, and his cock strained against its plastic holder, he realized that, as bizarre as it seemed, he was loving his situation.

William and an equally naked Randi joined them for lunch. Her shoes and stockings were the same as Mandy's, just black where hers were pink. Having both of them together, looking so sexy and desirable, was both delightful and torturous.

As they were cleaning up after eating, Randi looked at him curiously. 'Can I ask you something? I'd really like to know.'

Jim nodded and made a little 'go ahead' motion with his hand.

'Why do you like this? I guess I don't get it. I'm not trying to insult you or anything, but why do you like being locked up and frustrated like this?'

Jim smiled crookedly and gave her an honest answer.

'I don't know.'

Everyone laughed, and he continued.

'Why does anyone really like anything? Some people are into feet, or spanking, or tickling. Some guys like big girls, some prefer little skinny girls, some guys like long hair, some guys like short hair-but I don't think any of them could tell you *why* beyond 'it turns me on' or 'I think it looks better' or something like that.'

There were thoughtful nods of agreement.

'You're right,' William said. 'I don't know why I like most things, just that I do.'

He winked slowly. 'But I gotta admit, I'm glad its not me!'

There was more laughter, and he scooped the naked Mandy up in his arms.

'We'll see you both in-oh an hour or so.'

Mandy squeaked and kicked her feet cutely as the muscular handyman carried her off to his bedroom.

Jim and Randi were alone in the kitchen. She really did have a lovely body, he mused-long legs, nicely curved hips, and of course those incredible breasts-and a very pretty face.

'Ok,' he began, 'now it's my turn to ask you something.'

She looked at him a little warily. 'All right.'

'What-what does Lady Connie get out of all of this? She rarely has visitors, the only time she seems to leave the house is to go shopping with Candy...I don't get it.'

He paused and swallowed. 'I know she doesn't do anything with me or William, sooo-what about you and the other girls?'

Randi's smile was sweet as sunshine. 'The Lady told me once, right after I started working here, how to answer a question like that.'

Jim looked at her and waited.

Randi's smile became a soft laugh. 'She said for me to say-I'm not allowed to say either way.'

He looked a little puzzled, so she explained.

'She meant I'm not supposed to say yes, and I'm not supposed to say no. I wouldn't tell you-I wouldn't tell anybody-either way.'

'I didn't mean to be nosey. I adore the woman, and she makes me curious.'

Randi laughed and ruffled his hair playfully. 'Don't worry about it. Come on, we got a bathroom to clean.'

He gave her a big mock scowl, but followed her dutifully upstairs to go back to work.

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CANDY rubbed and ground against him, stark naked, purring and whispering obscenely.

After spending most of the day with curvy Mandy and busty Randi, her slim body was a delightful change of pace. And the combination of her soft, high-pitched voice and dirty talking made his blood boil.

Again her hands found the hard, unyielding plastic of his chastity, and again she acted all disappointed and pouty. But this time Jim didn't wait. Smiling at Lady Connie, he wrapped his arms around the girl's tiny frame, his fingers digging into her cupcake buttocks as he lifted her off the ground.

'No little one, Daddy can't fuck you,' he said as he carried her to the couch. 'But I can do plenty of other things.'

He pushed her legs apart and thrust one, then two fingers deep into her soft wet pussy, pumping her relentlessly. He lowered his mouth and found her clit with his lips and tongue, sucking and licking hard, forcing the squirming girl to orgasm.

Her sweet gasps and moans were as satisfying to him as any climax he had ever felt, and he realized how well his mind and body were responding to the chastity training.

That evening, he got a surprise and a little bit of a break when he went to the Lady's bedroom. Randi wasn't there. It was just the Lady and Candy, already dressed for bed in their nightgowns.

Lady Connie greeted him as he entered, her smile warm and tender.

'My darling boy,' she said with genuine affection, putting both palms on his face. 'I know this is a strain. I'm so proud of you. You're doing so well!'

'Thank you ma'am. It's been both horrible and wonderful.'

Her smile widened. 'Which is exactly the point.'

She dropped her hands and turned her head, and he bent to kiss her cheek. As his lips brushed her skin, she whispered softly.

'Tomorrow.'

He looked at her quizzically, and her eyes sparkled with amusement.

'Good night, dear boy.'

'Good night ma'am.'