Lady Connie Ch. 01

He also found a pair of white slacks, a white dress shirt, and a black bow tie one a single hanger, and a pair of dungaree overalls on another-his indoor and outdoor work uniforms.

Sunday morning at 8 Jim entered a small room on the lower level of the manor. This was the daily room, where every morning the group would gather to receive their instructions and assignments for the day.

He met Randi, the upstairs maid, and smiled as he understood the Lady's pun. Where Mandy, the downstairs maid, was a bootylicious brunette and wore a uniform designed to show off her curvy backside, Randi was a tall, stacked brunette, who wore her hair short and whose uniform top was a tiny string bikini, with cups no bigger than quarters that just barely covered her nipples.

Jim tried not to gawk, but damn if Randi didn't have the finest looking breasts he had ever seen. Full, firm D cups at least without a trace of sag.

Lady Connie entered a few minutes after 8, smiling and nodding when she saw her servants lined up, hands demurely behind their backs.

Good mornings were exchanged, and then she called Jim forward.

'Everyone, Jim's first day is today. I trust you will all make him feel welcome and help him with any questions or concerns.'

She introduced him one by one to the others, even though he knew William pretty well by now-and had gotten a blowjob from Mandy!

'Regular uniforms today,' the Lady announced. 'Jim, you'll stay with William. He'll show you around the house and grounds and you can familiarize yourself with the usual schedule.'

She dismissed everyone except Jim and Mandy, smiling as she sat down in a comfortable chair.

'Now Jim, my dear boy,' she began. 'The first part of your training is to get your body used to having regular climaxes at regular intervals during the day. So for the next week, every day at 8:30, 4 o'clock, and 10 o'clock, one of the girls will pleasure you.'

Jim looked at her in surprise.

'Maam?'

She smiled gently. 'I know your role is chastity slave, darling. That will come soon enough.'

She looked at the downstairs maid. 'Mandy my dear, if you would?'

And again, the big bottomed, lovely girl undressed and gave him a fantastic blowjob.

As Mandy sucked his cock, the Lady explained her reasoning.

'After a few days, your body will be used to release at regular intervals. That will make it all the more delicious when your chastity training starts in earnest. Then you will still receive the stimulation at those times, but without the final climax.'

Jim shuddered and moaned, his hips bucking, thrusting his cock into the girl's sweet mouth.

'Do you understand dear boy?' the Lady asked.

'Y-yes maam, I think so,' he managed to gasp.

She smiled. 'Good. Then give dear Mandy her treat and we can go have breakfast.'

With a groan, he let himself blow in the girl's mouth, and she swallowed it all happily.

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Breakfast was spectacular-eggs Benedict, crisp bacon, fluffy waffles, fresh fruit, fresh squeezed orange juice, and coffee. Then he changed into his overalls and went out with William, who showed him around the grounds.

William pointed out the weekly tasks-moving, trimming, watering, etc-as well as a couple of longer term projects like painting one wing of the house and repaving a walkway.

'Let's get something straight,' he said as they checked a goldfish pond and strained out some of the surface vegetation. 'This part of your job is important too. I take it seriously and we expect you to do the same.'

Jim nodded. 'I intend to. I'm not afraid of working.'

William laughed his infectious laugh. 'Good man. This is a hell of a good gig. Don't mess it up by being lazy.'

They took a break about 1:30 for a light lunch of sandwiches and iced tea, then got a little more work done. About 3:45, Jim looked at his watch and smiled.

'Uhh-I need to go inside for a bit.'

William grinned at him. 'I know.'

He gave him a friendly clap on the shoulder. 'Enjoy yourself bro!'

Jim hurried inside and washed up, then reported to the Lady's office promptly at 4. She was at her desk, and Candy was sitting in the chair. The blonde girl turned and gave him a sweet, shy smile as he entered.

While the upstairs and downstairs maids wore sexy uniforms, the Lady dressed Candy, her 'personal' maid, like a young girl. Cute, flowing sundresses, flat shoes, her hair tied in a ponytail with a brightly colored ribbon-she looked beautiful and adorable.

Lady Connie smiled as Jim entered. 'You're very punctual dear. That's a fine quality.'

'Thank you maam, I do try.'

The Lady smiled and tapped her desktop. 'It's time again, dear boy. Time to have pleasure at my command.'

As she spoke, Candy stood up and bent over the desk, laying her upper body on the desktop. The girl reached back and lifted her cute dress over her hips, exposing her slim rump. She spread her feet apart, and Jim noted with pleasure that unlike the other maids, she was shaved smooth.

'Go ahead, Jim,' Lady Connie coaxed. 'It pleases me to see you enjoy yourself with Candy here.'

He didn't need to be told twice. Hastily, he opened his slacks and moved behind the girl. She made delectable noises of passion and wiggled her butt eagerly as Jim pressed his hardness against her.

Jim gasped as he entered her. She was so wonderfully tight! He started to rock in nice and easy, but that wasn't the plan.

'Go deep and hard, dear boy,' the Lady commanded softly. 'She's a big girl-she can take it.'

He gripped Candy's slim hips and started to thrust, loving the way her tight pussy gripped and squeezed him. She whimpered passionately and wiggled some more.

'Fast and hard Jim,' Lady Connie said mildly. 'Candy, push back harder dear.'

He moaned as increased the speed of his thrusts. Lady Connie spoke casually as he fucked her maid, telling him he was going to get used to following commands to the letter.

'Soon, your greatest pleasure will come not from the act, but from the obedience,' she said, smiling as he bucked wildly and blew his load into Candy's soft body. The girl climaxed at the same time, her soft gasps and fluttering inner muscles adding to his enjoyment.

Supper was another amazing meal, and he got to meet Alexander, the Lady's cook, as they all sat down and ate together. Mindful of the fact that Alexander wasn't privy to everything that happened in the rest of the house, Jim stayed pretty quiet.

The conversation was friendly and easy, but impersonal-lots of talk about TV shows, movies, current events, but nothing about their private lives-which was fitting because aside from the cook, none of the Lady's staff *had* a private life.

They relaxed for a bit, then Jim and William pitched in to help the maids clean up the kitchen and put the dishes in the dishwasher. Then William took him to the exercise room for a short but intense workout.

A shower, a little television, and it was almost 9:00. Smiling, he reported as ordered to Lady Connie's boudior.

The Lady was lounging on her bed, dressed in a very modest blue nightgown. Candy apparently shared the room with her-she was curled up in a small, low round bed next to the Lady's massive four-poster, wearing (of all things) pajamas with feet, decorated with pictures of a popular cartoon character.

'Dear boy,' the Lady greeted him warmly. 'We hope you enjoyed your first full day?'

Jim blushed a bit as Randi, the upstairs maid, took his hand and led him to the bed, gently coaxing him to lay down on his back at the very end, his legs hanging over the edge.

'I have maam, thank you,' he replied honestly.

He watched, transfixed, as Randi stripped, then poured vanilla-scented oil over her magnificent breasts, massaging them sensuously. His cock swelled in eager anticipation.

From seemingly far away, he heard Lady Connie say 'We know three times in a day is a lot, dear boy, but you're still a young buck. We think you can handle it.'

'I'll do my best,' he said, panting as Randi knelt by his feet and tugged down his white slacks. Next to him on the bed, the Lady sat up straight, and Candy knelt behind her, nonchalantly brushing her shoulder length hair.

'Don't hold back darling,' the Lady instructed as Randi pressed her huge, firm breasts around his hardon, sliding them up and down in an awesome titfuck.

It answered one question that had been floating through his mind. Randi's breasts were far too soft and warm to be anything but 100% real. It was amazing to see tits that big be that perky.

Lady Connie continued to talk matter-of-factly about how his pleasure came at her whim, by her command, and Candy tended to the Lady's hair...and all the while he got harder and harder.

In spite of having already had two of the best orgasms of his life that day, it didn't take long before he was bucking and groaning, spurting his load into Randi's ample cleavage. Lady Connie smiled approvingly as her upstairs maid used her hands to press her boobs together, squeezing every last drop of sperm from Jim's balls.

'Very nice my dears,' she said tenderly as Randi wiped herself clean with a small towel, and Jim lay on his back, panting happily.

Randi folded the little towel carefully, and leaned over the bed. Lady Connie offered the girl her right cheek, and the tall maid kissed it softly.

'Goodnight my Lady,' she purred, and picked up her clothes, carrying them and the towel out of the room.

Finally, Jim blew out a huge breath and managed to get to his feet. He pulled his pants up, and saw the Lady was offering him her left cheek.

He was no dummy. He figured out the little ritual. He bent down and kissed her cheek softly.

'Goodnight maam,' he said respectfully.

She smiled with genuine warmth. 'Sleep well, dear boy. Tomorrow is another big day.'