Lady Connie

Author's note-I've submitted two series of stories to this site, and both have been dark, violent and frankly pretty unpleasant. I wanted to write a BDSM story with people that were happy, content with their roles and getting what they wanted. This is the result. Feedback, votes and comments are always greatly appreciated-even negatives!

*****

JIM closed his eyes and inhaled deeply, struggling not to moan or buck his hips as the beautiful 'downstairs maid' slowly stroked his aching cock. Lady Connie was watching, and she preferred him to stay still and quiet during his arousal sessions.

Mandy smiled, one dainty hand resting on his firm ass, feeling him throb in her other hand as she caressed his throbbing member. She slid her fingertips over his swollen head on every stroke, adding to the sensations.

He clenched his teeth and felt his balls tighten. More than anything, he wanted her to keep going until he shot his load. But discipline-and the thought of how much he could lose-forced the words from his lips.

'S-stop,' he managed to gasp.

Mandy finished her stroke, then moved her hand to his stomach and turned her head to look at Lady Connie.

'Five more, I think,' the handsome woman said, amusement in her voice. 'You can take five more, can't you darling?'

A shudder ran through Jim's body, but he took another deep breath.

'Y-yes maam,' he answered quietly.

Mandy giggled musically as she wrapped her fingers back around his rock hard cock.

'One,' she whispered, drawing the word out as her hand slid up and down the full length of his erection.

'Two,' she continued to tease him with her voice as well as her soft hand.

Jim's knees nearly buckled as the count continued, each soft stroke making his cock throb. When she finally got to five and released him, he let out a long sigh of relief.

'Well done, my pets,' Lady Connie praised.

'Thank you my Lady,' Mandy said, smiling as Jim stammered 'th-thank you maam.'

Mandy retrieved the icepack, her large backside twitching under her tiny maid's skirt. She moved back to Jim's side and pressed it gently against his groin.

He balled his hands into fists as the cold softened his erection. In moments, he was flaccid, and the girl wrapped the chastity belt back around his hips, trapping his cock in the clear plastic tube.

Lady Connie lounged on the couch, her eyes sparkling.

'A good job Mandy,' she smiled, and the girl gave her a little curtsey.

'Outdoor clothing today Jim,' she continued. 'You'll be helping William with the shrubs.'

'Yes maam,' he said respectfully.

The Lady's smile widened. 'Of course, first you need to thank Mandy.'

'Of course maam,' he replied. Mandy smiled eagerly and lay down on the plush carpet, her skirt lifting as she spread her legs, exposing her naked pussy.

With a sigh that was half pleasure, half agony, Jim knelt between the girl's open legs. He slid his hands under her, cupping and squeezing her plump buttocks, and tongued her pussy with all his skill. As he licked her to orgasm, his cock twitched, futilely trying to harden in its plastic prison.

xxxxxxxxxxxxxxxxxxxx

IT ALL started for Jim when he met William in a BDSM chatroom.

He'd been a reg there for about a year, occasionally having cybersex or a sex-related chat, but usually just hanging out in the rooms joking with the people he knew, when he got a message from *William_LC*.

Give me 5 mins of ur time. I swear it will be worth your while

So he opened a private chat window, and the two talked.

William began by assuring him he wasn't gay, and wasn't interested in him sexually. That was fine. Jim wasn't homophobic, but he had never been interested in sex with other men.

read your profile. i may have the perfect RL place for u

Jim read that message over and over, his heartbeat quickening.

I'm listening, he typed in return.

Jim had put in his profile his desire to be controlled sexually. Ever since he'd been old enough to have sexual fantasies, the best and hottest ones had revolved around giving up his power to a woman-not as a victim or a brutalized slave, but because he wanted to.

The idea of being obedient-of sometimes being denied, of being told when he could and couldn't orgasm, of putting another's pleasure way above his own-drove him crazy. Unfortunately, every time he'd tried to broach the topic with a real life girlfriend, she hadn't been interested.

He read excitedly as William continued. He worked for a rich, sweet, eccentric older woman in California. It was a great job, good pay, fantastic fringe benefits-and the Lady was looking for one more male servant.

theres sex but not with her or me. shes got 3 realy pretty girls that work for her n she likes to watch & direct.

Jim was rock hard by this time, and intrigued by the whole setup.

she sent me to the chat rooms to look for someone just like you, William finished.

Jim thought for a moment. He was done with college, his job was nothing special, and he wasn't in a relationship. Still, moving from his native Ohio to California would be a huge step.

what do I have to do? he finally asked.

few question 1st, William replied.

is ur profile true? are those recent pics?

They are. I just added some this month

ok sorry i gota ask this. are you pretty big when ur soft?

Sitting in his chair, his laptop on his thighs, Jim laughed out loud.

I think so. Judging from my time in locker rooms anyway.

can we chat sum more in about 2 hrs? ill talk to the Lady n show her ur profile

OK I'll see you then.

Two hours later, he found out Lady Connie approved of him. Three hours later, he logged off, having made arrangements to have a plane ticket waiting for him that Saturday at her expense, as well as a three night reservation at a really nice hotel and a rental car.

'If nothing else,' he thought, 'I get a little vacation out of the deal.'

And five days after that, he met the Lady, William and Candy at an expensive restaurant for what she called 'the initial interview.'

He guessed Lady Connie was in her early fifties. She was still an attractive woman, with a soft voice and an aura of easy confidence. Jim guessed the jewelry she was wearing was worth more money than he would make in several lifetimes.

William was a towering black man, several inches over six feet tall, well-dressed, with a quick smile and a booming laugh.

And Candy-damn! She was a quiet, demure little blonde, barely out of her teens, and achingly gorgeous in a flowery sundress.

The group enjoyed an excellent, leisurely meal as Lady Connie asked him a lot of general questions about his background, education, family-she had a gentle smile and was easy to open up to.

At last she got around to talking about the job.

'You will work for me,' she said, smiling. 'Don't kid yourself about that. You'll assist William with outdoor chores, gardening, and small repairs around the estate.'

She took a sip of tea and continued. 'If you don't know how to do something you'll learn-through books or the Internet. William is an excellent handyman-now.'

William laughed. 'I had a good teacher. I just hope as can teach Jim here as well as Matt taught me.'

When Jim gave a questioning look, William explained that Matt had worked for the Lady until a couple months ago.

'You'll kinda be taking his place.'

'Ahh,' Jim nodded.

That was when Lady Connie dropped the first bombshell.

'The pay will be $1000 a week. You'll live at the house, so you won't have any expenses. You'll have the use of a car, and be off-duty every week from 6 PM Friday until 8 AM Sunday.'

She looked at his raised eyebrows and smiled. 'If you stay for one full year, you get a one million dollar bonus. If you stay two years, you'll receive a five million dollar bonus.'

Jim was stunned. He knew his mouth was hanging open, but his brain didn't seem to be working right.

William laughed again, loud and cheerful, and Candy smiled sweetly.

'It's the real deal bro,' William said, laying a hand on his forearm. 'I've been with the Lady sixteen months. During that time, Matt and two maids have finished their time and I know for a fact they got their bonuses.'

He grinned. 'I got my first one when my year was up too!'

'Are you interested so far dear?' Lady Connie asked him knowingly.

'Uh...ummm...' he stammered, then felt his mouth widen in a grin. 'Absolutely!'

She smiled and nodded. 'Good boy.'

The Lady handed him a card. 'Come to this address tomorrow at 2 PM for the more...intimate part of the interview.'

She dabbed her lips daintily with a napkin and started to stand up. William quickly rose and helped her with her chair, and Jim had enough presence of mind to get on his feet as well. It was the right move-she gave him a smile of approval.

'Come Candy,' she said to the girl. 'We have some shopping to do.'

'Yes, my Lady,' the girl replied softly.

Lady Connie held out her hand, and Jim took it gently in his own.

'It was nice to meet you, dear boy,' she said smiling. 'William will tell you the rest.'

She turned to William. 'Be back at the house by dinnertime,' she told him.

'Of course, Lady Connie,' he said with a smile and a little bow.

The women left, and William finished filling him in.

'Lady Connie likes to be surrounded by smart, attractive, but obedient people. So be smart. Tell a couple people you trust where you're going tomorrow, and set up a time to call them when you're done.'

Jim's brow furrowed a bit. 'Why?'

William laughed heartily. 'We're a group of total strangers you met online, bringing you to a private residence to discuss sexual service. Don't you think you should protect yourself?'

'Well, when you put it that way...but I wouldn't be going if I thought there was a chance of trouble.'

'I know.'

William reached into his jacket and handed Jim an envelope.

'My Lady's compliments,' he smiled as Jim looked in and saw the bundle of twenty dollar bills. 'Have a good time the rest of the day and night-but please go back to your hotel alone...if you know what I mean.'

He tossed three more twenties on the table for a tip, and left. Jim shook his head in amazement as he finished his coffee.

'Damn,' was all his brain could come up with.

xxxxxxxxxxxxxxxxxxxxx

He was there at ten minutes to two the next day. Her estate was incredible-big enough to be a resort, complete with a gate and a security guard.

Mandy answered the door before he could ring the bell. He found out later the downstairs made kept a wrap-around skirt on a hook right by the door, so she could greet visitors without exposing herself.

Jim tried not to stare at her fabulous, plump rear end as she led him to the Lady's chamber. Instead, he glanced around the rooms they passed through. Tastefully decorated, the whole place screamed of an economic status he had only previously seen on television.

'Wait here,' the girl told him, and first tapped on a closed door, then slipped inside.

Jim was wearing dress slacks and a striped polo shirt, just about the best clothes he owned aside from the suit he had worn the day before. He hoped he would make another good impression.

Mandy reappeared, holding the door open. 'Lady Connie is expecting you,' she said with a friendly smile.

He stepped into her office. It was done in white and pale blue, with big windows and a few photos of a younger Connie on the walls, posing with celebrities and even two Presidents.

'Jim my dear boy,' she said as she came around the desk. 'Right on time, that's a good sign!'

She took both his hands in hers and brushed her lips to his cheek.

'You look lovely, maam,' he said honestly.

She chuckled quietly. 'Flattery is a good thing, as long as it's not too thick.'

She returned to the far side of the desk. 'Sit, sit. Have some coffee-it's fresh.'

'Thank you,' he said, and poured himself a cup from the silver pot on her desk.

'Sugar? Cream?'

'No thank you maam,' he said and took a sip. It was as good as he'd expected it to be in this place.

After pleasantries, she laid an official looking document on her desk-a non disclosure agreement.

'It's mostly to prevent people who work for me making a cheap profit by writing one of those awful tell-all books,' she said as he read it over. 'Anyone will tell you-I reward loyalty very generously-and take an equally dim view of betrayal.'

'I don't have a problem with that maam,' Jim said, and signed his name. She thanked him and put the contract in a desk drawer.

She touched her thumb to the corner of her mouth, her eyes twinkling gently.

'Now, I'm sure you've been wondering about the...more scandalous aspects of your role here.'

He couldn't help smiling. 'Yes maam, I'm curious.'

'Without being gauche, I will tell you that I'm fortunate enough to have the money to indulge myself. My ideal personal staff consists of five people. Three maids-you met one of them coming in-and two handymen.'

Jim nodded, giving the woman his full attention.

'While I am never cruel or violent, I do expect both respect and obedience to the terms of your role. Too many failures and you will simply be dismissed.'

He nodded again. 'Of course maam.'

'Your role in the household would be,' she paused and pursed her lips for a moment, 'well I dislike the word slave but it's fitting in this case. Your role would be as a chastity slave. Do you understand what that means?'

'I have some idea maam, but there are a lot of variations.'

'Indeed there are. Your chastity won't be constant. You will be allowed relief once a week, every Thursday evening. Otherwise, you'll wear a chastity device most of the time. We'll measure you and have one custom made to fit as comfortably as possible.'

He gulped and nodded, both scared and aroused as he heard one of his greatest fantasies described.

She smiled again. 'From what I read about you at that site, this should be something you can not only handle, but find a great deal of fulfillment in.'

His mouth was dry, so he took a sip of coffee before answering 'yes maam.'

'There will also be times, at my whim, that you will be allowed' she chuckled, 'pleasure.'

'That's good to know maam.'

'Before we go any further. You're a good looking, well-built young man, but there's still one more thing I need to see.'

She looked at him boldly. 'Are you flaccid right now Jim?'

He blushed a little. 'No maam, I'm afraid I'm not.'

She smiled indulgently. 'That's to be expected.'

She pressed a button on her desk and spoke into the intercom.

'Mandy? Would you come in here a moment dear?'

He heard the maid answer, 'Yes, Lady Connie,' and in moments the girl was in the room with them. She had removed the longer outer skirt, and the outfit she was wearing barely covered her secrets. She smiled wickedly at Jim as she approached the Lady's desk, and stood with her hands behind her back, waiting.

'Dear, we need to inspect young Jim here, and probably measure him for his chastity device. Please disrobe and see to his satisfaction.'

'Yes my Lady,' the girl replied, and with little ceremony or modesty she undressed. Jim's mouth hung open in amazement, and his cock throbbed as the beautiful girl turned his chair to a 90 degree angle to the Lady's desk and knelt between his feet.

Mandy didn't hesitate. She unzipped his pants and freed his erect penis, giving it a couple firm strokes before gripping it gently at the base, holding it straight up.

Lady Connie half rose from her chair and looked openly at his hardon.

'Very nice in that state,' she purred, and nodded to the kneeling girl.

'Go ahead dear.'

Mandy made soft humming sounds as she took him into her mouth. There was nothing teasing or loving in her technique. She was giving him head with the sole goal of making him cum. Her head bobbed over his lap as she sucked him fast and hard, her tongue caressing his shaft as it slid in and out of her mouth.

'Oh god,' he groaned, his hand lightly touching her head, not impeding her movements. She sucked and sucked until she felt him swelling hugely in her mouth. Then his cum spurted, and she gulped down every drop.

He panted and gasped as he softened in her mouth, a little embarrassed at how quickly she'd been able to bring him off.

'Thank you Mandy,' he heard the Lady say, and the girl rose, licking her lips as she gathered her clothes.

'It's my pleasure to serve, my Lady,' she said, and slipped from the room.

Lady Connie came around the desk again, a measuring tape in her hands. 'Can you stand up dear?' she asked.

He pushed himself to his feet, his slacks pooling around his ankles, and she measured his hips, waist, his thighs both individually and together, and finally his spent cock.

'Over five inches when soft,' she murmured. 'Very nice!'

She wrote all the numbers down on a small pad. 'You can get dressed now dear,' she said.

He pulled up his pants. 'Don't worry about how long that lasted, dear-or rather didn't last. Young men need to learn control.'

He blushed a little, but nodded. 'Yes maam.'

She handed him a business card. 'I think you'll be perfect, dear. This is a testing lab. They'll check to make sure you don't have any nasty diseases or anything. You have an appointment at 4:30. They will rush the results for me, so I should be able to call you tomorrow before noon.'

'I'm pretty sure I'll pass maam. I hope so. I'd really like to work for you.'

Her smile was wide and genuine. 'You're a dear boy. I hope you come work for me too.'

xxxxxxxxxxxxxxxxxxxx

The tests came back clean, and he was officially welcomed to the 'family.' Then he flew back to Ohio and spent two weeks settling his affairs and packing what he needed to bring back to the west coast.

'While you're away dear, please don't sleep with anyone. And I would ask that you...relieve yourself as little as possible,' Lady Connie had told him just before he left.

Blushing, he had agreed, and she touched her lips to his cheek. 'Such a sweet boy,' she murmured.

While he was home, he did a little research about his new employer. She came from old, OLD European money. Her family had moved first to Canada, the to the US in the aftermath of World War I. She had two daughters who lived in France, and had been married and widowed twice-the last time a dozen years ago.

She was a well-respected patron of the arts, owned homes in at least five different countries, and her charitable foundation raised as much as ten million dollars a year for various causes.

And in a few days, he was going to be her chastity slave. All he could do was chuckle and try to swallow his nervousness.

At last, everything was ready. He had agreed to donate all his furniture and everything he wasn't taking with him to his two roommates, so they helped him pack his clothes, books, and sentimental stuff like photographs in a small moving van for the two day drive to southern California.

He arrived, as planned, on Thursday afternoon. That gave him a couple days to settle in with no duties until Sunday morning, when he was expected to join the entire group for breakfast at 9 AM.

William had explained meal rules as they drove home after returning the moving van. The Lady employed a cook who prepared breakfasts and suppers Sunday through Friday. He was not one of her 'sexual' employees, so discretion was necessary if you happened to see him-which wasn't common as he never ventured outside the kitchen and dining room.

Lunches, weekend meals and snacks were up to him. He had a refrigerator in his room, and was welcome to use the kitchen as long as he cleaned up after himself.

And yes, Lady Connie did expect you to dress up for dinner-to the point that as he was unpacking, he found four very fine suits in his closet-black, navy blue, white, and pinstriped.