Lady Connie Ch. 02

Story Info
Jim gets his chastity device.
5.2k words
4.59
32.9k
15

Part 2 of the 2 part series

Updated 06/07/2023
Created 04/29/2015
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JIM'S DUTIES included more than just yard work and maintenance. This morning, he was helping the downstairs maid, moving or lifting furniture out of her way so she could vacuum.

As he held up one end of a sofa, two thoughts kept bouncing through his mind. First, that the next day his genitals would be locked in a chastity device...and second that Mandy had the most incredible rear end he'd ever seen.

It was a true work of art. Plump, round, firm-she was truly Sir Mix-A-Lot's wet dream come to life. And the absurdly short skirt of her maid uniform did more to put it on display than cover it up.

He was erect again, his cock pulsing in his tight briefs. It was strange-he was having more and better sex than he'd ever had in his life, and it seemed like it just made him hornier. It seemed like any kind of stimulation, visual or otherwise, made him hard.

Mandy turned off the vacuum for a moment, and he gently lowered the sofa down onto the thick, plush carpet. Suddenly self-conscious about the way he'd been leering at her body, he cleared his throat.

'So,' he began awkwardly. ' Mandy, Candy and Randi-no way those are your real names.'

The girl laughed softly. 'No, they're not. Lady Connie has her maids take those names while they work for her.'

She gave him a bold smile. 'And you're allowed to look at my ass, sweety. It's not like you haven't seen it before!'

He shook his head, blushing and laughing. 'I'm sorry. This is just such a strange situation.'

Mandy continued to smile as she rolled the vacuum to the other end of the couch, her wide hips swaying delectably. 'Yeah it is, but it pleases the Lady-and for what she pays us, she can call me whatever she wants.'

Jim nodded and lifted the other end of the couch, enjoying the view of Mandy's barely covered rump as she ran the vacuum. This was by far the best job he'd ever had!

xxxxxxxxxxxxxxxxxxxx

THAT night, he got a special treat. He was just about to turn off the light when there was a soft tap at his bedroom door.

It was Lady Connie, flanked by both of her maids.

The Lady smiled at him with genuine affection. 'We want to make sure you are...thoroughly drained in the morning. The girls are going to stay in your bed tonight and service you any time you get become erect.'

Jim blinked in surprise, the blood already rushing to his organ. 'I...thank you ma'am,' he stammered.

She smiled again, and gently stroked both maids heads. 'Take good care of him, pets,' she said softly.

Mandy and Randi turned, kissing the Lady's cheeks. 'Goodnight my Lady,' they whispered in unison.

'Goodnight dears,' she answered, and left the three of them alone.

The girls were both wearing long satin robes. They looked at Jim and smiled as they untied the sashes at their waists and let them fall to the carpet.

His breath quickened as they came to him, stark naked, and his cock swelled to full erection, tenting his pajama bottoms.

'Come to bed,' Randi purred, and the girls took him by the arms. Mandy flicked off the light as he lay down on his back.

In short order, his pajamas were off, and two soft mouths went to work pleasuring his cock. They worked as a team, licking and kissing his shaft, then taking turns sucking him deep while the other stroked her tongue over his already churning balls.

It was the most incredible thing he had ever felt.

Even in the dark, he could tell which girl was blowing him. Randi had a much lighter touch, her mouth and tongue caressing him gently, where Mandy seemed to know only one way to give head-fast and hard.

The way the girls moaned and gasped and purred, obviously enjoying what they were doing, spurred his lust as much as their mouths, and even though he tried with all his might to make it last, soon he was groaning with bliss and spraying his load into a soft feminine mouth.

Twice more during the night, he half-woke up to the feeling of soft, warm mouths and wet tongues on his cock, like the best wet dreams he'd ever had. In between the fabulous double blowjobs, he slept like a rock.

The morning alarm rang, and he looked up to see Randi straddling him, her beautiful face contorted in passion as she slowly rode his cock. Her fantastic breasts jiggled sweetly as she panted with pleasure, her pussy a velvet vise around his shaft.

Mandy laid her head on his shoulder and nibbled his ear. 'Look at those gorgeous tittys,' she giggled. 'Play with them. Pinch her nipples hard. She's gonna cum all over your cock!'

Jim slid his hands up Randi's torso and ran his hands over her amazingly firm melons. His fingertips gripped the swollen nipples, feeling them throb as he squeezed and tugged.

'Ooooh...ohhh god,' Randi moaned.

'Harder!' the voice in his ear hissed, and he pinched savagely, bucking his hips to drive his hard rod even deeper into Randi's heated softness.

The girl arched her back, groaning and trembling, and Jim felt her cream soak him as she climaxed, grinding down hard on his cock.

'Mmmm yessss,' she purred, smiling down at him and licking her lips sensuously as she slid up and off him.

'My turn!' Mandy giggled as she rose to her knees. Randi lay on the other side of him, wrapping his arm around her quivering body.

'Damn that was good,' she mumbled as Mandy swung her leg over his body. She was facing his feet, teasing him with a spectacular view of her oversized ass, and she wiggled and corkscrewed her hips as she fucked him slow and deep.

'Tell me when you're gonna cum,' Randi whispered. 'It's my turn to swallow.'

'Fuucckk,' Jim gasped, his hands roaming all over Mandy's luscious cheeks. She was wonderfully tight, milking every inch of him as she slid exquisitely up and down.

'Look at that fat ass,' Randi moaned seductively in his ear. 'It's so beautiful bouncing on your big dick!'

'Ahhh shit! I'm, I'm gonna...' he started to say, and Mandy slid off him with a wet slurping sound, turning quickly between his legs as Randi moved to take his throbbing cock head into her mouth.

He lifted his head weakly and moaned at the erotic sight. Mandy wrapped a soft hand around his shaft and jacked it fast and hard, and Randi looked up at him as she nursed and suckled on the sensitive head.

He flung his head from side to side and blew his load, spraying ropes of cum into the girls mouth, and she swallowed thirstily. Mandy kept squeezing and pumping his rod until it went limp.

He collapsed, panting blissfully, and the girls snuggled against him.

'Five minutes-then it's shower time,' Mandy whispered as they nuzzled him. His hands caressed their soft backs.

'Thank you both for the best night of my life!' he said with a weak smile.

xxxxxxxxxxxxxxxxxxxx

JIM stood in the center of the daily room, hoping his legs wouldn't give out. The moment he had dreamed of for so long was here at last.

Lady Connie smiled warmly. 'This is your last chance to back out, dear boy,' she said softly.

He didn't trust his voice, so he just shook his head.

The Lady's smile widened, and she nodded to the two maids flanking him. They gently but quickly undressed him completely.

When he was completely nude, the two girls knelt at his feet. They began to wash and clean his cock and balls with wet wipes, and incredibly, he stirred back to life.

Lady Connie chuckled softly. 'Oh dear, we can't have that. Candy my pet, if you would be so kind?'

Smiling, the little blond girl knelt between the maids and took his stiffening dick into her mouth.

Jim gasped with pleasure as the other two girls added their tongues to the mix. Lady Connie watched and smiled.

'I'm glad his happened. Now you've had he chance to sample all of my girl's charms!'

She turned, and William moved from the corner, a wooden box in his hands. The Lady took it from him with a nod, and lifted the lid, showing Jim the chastity belt within.

He groaned deep in his throat, and Candy picked up the intensity of her blowjob, her mouth eagerly devouring his cock.

Jim realized it was all staged, a little show for his benefit to increase his excitement-and it worked. With an animal moan, he grabbed Candy's head and thrust all the way into her soft mouth, shuddering as he shot his load down her throat.

The three kneeling girls beamed up at him, and Candy nursed on his softening prick until it slipped from her mouth, limp and spent.

She rose and kissed his cheek, whispering 'thank you' as the other two maids resumed cleaning him. Finally, Lady Connie softly said 'That's sufficient, girls,' and they stood, moving to the side.

Her eyes filled with warmth, the Lady put the device on him. A thin strap wrapped around his scrotum, just below the base of his organ. Another strap went around his waist, and two more framed his buttocks, almost like a jockstrap.

Finally, she carefully slid the clear, curved plastic sheath over his flaccid penis. Moving around him, she adjusted the straps until it fit snugly around his hips.

'How's that feel, dear boy? Not too tight?'

'It-it's fine ma'am,' he managed to gasp. His head was swimming as his wildest fantasy came true.

Lady Connie stood before him. Taking both his hands in hers, she smiled her indulgent little smile.

'I'm very proud of you, Jim,' she said softly.

'The first few weeks will be the hardest. After that, I think you'll adjust to the routine.'

Jim nodded, his mouth dry, his heart pounding in his chest.

'Do you trust me?' the Lady asked earnestly, looking straight into his eyes.

He met her gaze, and nodded slowly, realizing that yes, he did indeed trust this woman.

'Yes ma'am, I do.'

'Good. I want you to know, I'm very good at pushing to the edge of your limits, but not beyond.'

She leaned and kissed his cheek softly. 'I promise you will suffer exquisitely, dear boy-and in the end you'll be grateful,' she whispered.

She had a tiny padlock in her hand. She stepped behind him again.

'From this moment on, dear boy,' she whispered, 'your penis and testicles belong to me.'

Jim heard the soft 'click' of the lock, and his chastity was complete.

She circled in front of him again and touched his cheek with a soft hand. 'I'm very happy you joined our little family, dear boy. And I'm very proud of you. We all are.'

She made a little ceremony out of putting the key in a little wooden box on her desk as the others surrounded him.

William approached and stuck out his hand. He didn't say a word, but nodded approvingly.

The girls each kissed his mouth sweetly, murmuring words of encouragement.

'I chose to do this on a Wednesday because I know it's usually the lightest chores day of the week,' Lady Connie announced, 'and I assume after last night you three are a bit sleepy.'

She smiled her indulgent-parent smile at Jim, Mandy and Randy, who chuckled, nodded, and blushed a little.

'So. An easy day today, complete with a nap. Would you like to take it now, or after lunch?'

Jim looked to the girls, and it was Mandy, the bravest of the Lady's maids, who spoke.

'I think after lunch, my Lady,' she answered.

'Good enough. And Jim,' Lady Connie added, openly admiring his imprisoned genitals, 'I think you should remain undressed today. It's such a lovely sight!'

Jim's blush deepened. 'As you wish, ma'am.'

'Do let me know if you get cold, dear boy.'

They went to breakfast (Jim put on a robe to eat, to avoid shocking the cook), and afterwards the maids did a little dusting and sweeping while William and Jim watched a lot of ESPN.

'You made the Lady very happy today buddy,' William told him at one point. 'I'm grateful.'

Jim just smiled. 'She's an amazing woman.'

'Yes, she is.'

They had a light lunch of turkey slices and fruit, and around 12:30 Jim went upstairs and took a leisurely two hour nap.

When he came back downstairs, the girls were watching some tear-jerker movie he had no interest in, so he went to the library and found a book about plumbing to study.

As the clock neared 4, he felt himself trying to stiffen. His body was so used to its four o'clock 'relief' that the arousal was automatic. He realized he wasn't sure if he was supposed to go to the Lady's office today or not. He decided not to risk disappointing her, and knocked on her door promptly at four.

'Dear boy,' she smiled widely, coming out from behind her desk to hold both his hands. 'No, we won't have any kind of session today, but it pleases me that you checked.'

Jim smiled and kissed her cheek.

'We won't have one tonight either, but do come say goodnight at the usual time.'

'Of course ma'am.'

xxxxxxxxxxxxxxxxxxxx

THE CHASTITY device took a little getting used to, but Jim was able to pee without any problems, and once he found a comfortable position, he slept reasonably well-although he noted that he wouldn't be sleeping on his stomach for a while.

He woke the next morning a few minutes before his alarm went off. His cock strained futilely against the barriers around it. It wasn't terribly uncomfortable, and the realization of what lay ahead-and the realization that he didn't *know* exactly what lay ahead and had no control over it anyway-made his pulse race with excitement.

Lady Connie had assured him he could shower normally with the device on, so he showered and shaved like any other morning.

He dressed in his loosest slacks and a polo shirt, leaving his feet bare, and precisely at eight, he entered the daily room with the rest of the staff like they always did.

The Lady was in a cheerful mood, greeting them all with tender cheek kisses.

'The usual routine today,' she announced. 'William, is there anything that needs my attention?'

'No ma'am,' he answered. 'Just regular outdoor maintenance.'

She nodded and continued. 'Regular uniforms as well-with one exception. Randi?'

The upstairs maid stood in front of her.

'Remove your top please, dear. William, if you would be so kind?'

'As you wish, ma'am,' he replied, and stepped behind Randi, wrapping his arms around her. His big hands slid up to her huge breasts, tweaking and pulling her nipples until they stuck out stiffly.

Randi moaned and shuddered as William fondled her, and Jim realized her breasts weren't just big, firm and fabulous-they were also extremely sensitive.

Lady Connie opened a box on her desk and removed a pair of gleaming golden nipple clamps. They weren't the cruel, harsh kind used for punishment-they had small, round paddles, lined with silk, that would hold the girl's nipples in a lover's caress for as long as she wore them.

Randi moaned again, her eyes smokey with arousal as the Lady attached the clamps to her swollen nipples.

'No top for you today, pet...obviously,' Lady Connie said softly.

Randi kissed her cheek. 'Thank you my Lady,' she said with genuine affection. Then she linked hands with Candy, and the two beautiful girls left the room.

'William, Mandy,' Lady Connie said when the door closed, 'please, enjoy each other.'

They smiled and fell into each other's arms. The Lady passed by Jim on her way to her couch. Touching his bicep, she whispered.

'Stay there and enjoy the show, dear boy.'

Her eyes twinkled with amusement as she sat and sipped her coffee.

Jim stood riveted as the pair undressed each other. His eyes widened in amazement when Mandy took William's pants off. Damn he was enormous!

William sat in a love seat at the opposite side of the small room, and Mandy mounted him eagerly. Jim's eyes were glued to her magnificent ass as it rose and fell, stunned that she could take such a huge dick with such obvious relish.

The downstairs maid bounced on William's cock, gasping and moaning to two climaxes, before he pulled her close and sprayed his cum up into her. Jim watched the entire show, his own cock straining helplessly in its plastic cage, desperately trying to get erect.

The Lady waited a few minutes after William's orgasm, then clapped her hands softly.

'Let's get moving my dears. Breakfast in five minutes.'

Mandy and William kissed each other passionately and got dressed. He winked at Jim as they headed to the door, and the two men followed Mandy's fabulous rear end as she swayed to the dining room.

xxxxxxxxxxxxxxxxxxxx

The day was bizarrely normal. Working outside on a couple of projects with William, he forgot at times he was even wearing the chastity belt.

Around three-thirty in the afternoon, he headed in to take a quick shower and wash off the sweat before heading to the Lady's office for his four o'clock 'appointment.'

Again, as the hour approached, his cock started to pulse, trying to get hard to no avail. The sight that greeted him when he closed the door didn't help his frustrated arousal.

Lady Connie normally dressed Candy like a demure little girl, but not today. This day, she wore an outfit straight out of a schoolgirl-type porn flick. Thigh-high white stockings rose out of black pumps, their heels at least five inches high. Her tiny, red plaid skirt barely covered her secrets, and she wore a white, short sleeve blouse unbuttoned, held on by a knot between her small breasts.

She managed to look cute, sexy, adorable and scorching hot all at the same time. The effect was devastating.

It only got better-or worse, depending on your viewpoint. Lady Connie didn't say a word-she just sat in her chair, a content expression on her face, as Candy sashayed up to him, continuing her sexpot little girl act.

'Mmm daddy you look so handsome,' she purred, slipping her hands under his shirt. 'You make your little girl so hot!'

She rubbed her slim body against him, her soft little hands caressing his chest.

'Mommy says I need to learn how to give give good head,' she said in her cute, high-pitched voice, and Jim groaned in sweet frustration.

'Please daddy,' she kept going, and if her passion was feigned, she was doing a marvelous acting job, 'please can I be your little blowjob princess? I'm so hungry for you big daddy dick!'

She took one of his hands and guided it under her micro-mini skirt.

'Feel how wet I am daddy?' she asked, and it was true. Her smoothly shaved pussy was dripping.

'That's just from thinking about how good you're going to taste-OOOooohhh!' she gasped as Jim pushed a finger up into her soft, wet pussy.

She moaned and ground her mound against his hand, clutching his arm for balance. Then she grabbed his wrist and brought his slick finger to her lips.

Looking straight into his eyes, she slid the finger into her mouth, licking off her own juices as she sucked it like a little cock. It made Jim's knees tremble.

'Mmmm now I want the real thing,' she giggled, and her hands went to his crotch. She felt the hard plastic through his slacks, and frowned. She tapped it with her fingertip.

'Aww,' she whined, pouting adorably. 'I guess I can't suck you off today!'

Lady Connie spoke for the first time since he had entered the room.

'No pet, you can't. But I'm certain Daddy Jim would like to taste you.'

Keeping up her act, Candy clapped her hands and squealed 'Goody!' like a kid that had just been told she could have ice cream. She strutted over to the couch on her heels, her hips swinging beautifully, and Jim followed, mesmerized.

Candy spun and dropped onto the sofa. She didn't even have to pull up her skirt. It was so short that as soon as she spread her legs, the hem was above her slim hips.

Panting eagerly, Jim fell to his knees and drove his tongue into her wetness. She gasped and bucked her hips, smearing cream all over his face as he ate her hungrily.

He plunged his tongue in and out, pausing only to lick and nibble her stiff little clitty, savoring her soft whimpers of need before thrusting back into her flaming pussy. Candy tangled her fingers in his short hair and squeaked with joy as he brought her to the peak of ecstasy.

'Very nicely done-both of you!' the Lady exclaimed with obvious pleasure as Jim licked gently, bringing the girl down from the heights of her climax.

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