Landlady Clare Ch. 01

"I only have about $500. I won't start work until Monday. I won't get paid for two weeks after that," he stated dejectedly.

Bill's pale blue eyes pleaded with Clare.

"There may be a way," Clare breathed out slowly after a lengthy pause. "Bring me all your money young man," she stated.

Bill's face lit with hope and he rummaged frantically through his backpack, emerging with a rumpled white bank envelope holding the sum total of his 'fortune'.

"I have some change in the car I could get," he suggested sheepishly.

Clare almost smiled at his obvious desperate eagerness to please, but retained her stern, business-like face as she quickly thumbed through Bill's money.

"I'll keep this for now and give you money as I feel you need it," Clare decided, retaining the envelope as she surveyed Bill who was relieved he hadn't been booted out - though now he was truly penniless!

"Here is the key to your apartment. Give me the spare key to you car and we'll register you at the community office," Clare said finalizing the arrangement.

She stood, handed the apartment key to Bill as he handed her his spare car key. She walked the few steps to the door connecting his apartment to her kitchen.

Bill rose to his feet and stared in undisguised lust at the rolling, firm, tanned ass of his new mature landlady.

"I have some things to attend to before we register you. I will be about half an hour. Be ready when I return, and do NOT masturbate!" she continued.

Bill's faced reddened brightly at Clare's remark and he simply replied, "Yes, Ma'am."

"There are homemade milk and cookies in your fridge. Enjoy them!" Clare invited as she stepped into her home leaving the door separating their two living spaces conspicuously open.

Bill stood in shock in the middle of his new home. He couldn't believe what he thought he just saw. Perched on the tips of his middle aged landlady's gorgeous nipples, were small drops of pale white milk!

His cock jumped at the possibility that this voluptuous matron was actually lactating.

As she walked through the doorway, Clare saw Bill stare in awe at her breasts and noticed his cock's reaction.

"Damn!" she said as she looked down at her breasts and saw the glistening drops of her milk there. She had not intended to reveal this particular secret to Bill just yet. On the other hand, he had reacted as she had hoped, with lust.

So far so good she thought. She moved to the staircase and climbed it quickly.

No need to check Bill's scanty references or do an internet search - Clare with her typical foresight had done her due diligence before ever accepting his interview.

But she did have two urgent matters to attend to.

The first was sitting at her desk watching Bill on her computer monitor via a camera hidden in his apartment. The second was attaching the suctioning cups to her now painfully distended nipples and starting the all too familiar milking process.

Clare did both expertly and quickly from long practice. She sighed in relief and pleasure as the machine began extracting her abundant milk and collected it in one of the clean glass bottles she preferred using. Feeling her warm milk flow through the dilated ducts of her mammary glands always produced this feeling of sexual contentment and arousal, though she admitted the pleasure was much more intense when an eager man was draining her wanting tits. Still, she could feel the familiar tingling in her juicing cunt. She hoped she - and her cunt - would be more fully satisfied later.

Her sexual excitement grew as she studied her new, young stud of a tenant attempting to make himself at home.

Bill stood for a moment holding the key to his apartment. He attached it to his keyring and began exploring his new home.

His prick tented the front of his pants noticeably, but barring masturbating to a quick ejaculation - an activity his landlady had expressly forbidden - there was nothing to be done for it.

It didn't take long for Bill to check out the desk, one straight backed chair, sofa bed, bathroom and kitchenette. His phone said he still had 15 minutes to wait for Clare's arrival and his formal registration as her tenant.

Bill couldn't stop thinking of Clare - her voluptuous, mature beauty and her confident manner. Her kindness in bending her rules to help him out in his moment of need (Clare would have chuckled at his naiveté). Her breasts! Maybe leaking milk! Bill knew he couldn't be THAT lucky.

Milk! Bill then remembered Clare's offer of 'Homemade milk and cookies.' 'Homemade milk?' Surely she had meant to say 'Homemade cookies and milk.'

Or had she? He suspected there was more to his new landlady then a middle aged widow looking to supplement her income.

Suddenly Bill realized he was hungry. He had been too nervous about his interview with Clare to eat lunch. So he opened his small refrigerator and extracted the plate of cookies and small bottle of milk.

He sat down to compose himself and sate his hunger with the thoughtful snack provided by his landlady and opened his laptop. The cookies were delicious - oatmeal, cranberry with a brown sugar glaze. He sipped the milk which looked like skim, but was surprisingly full bodied and sweet. It didn't take him long to finish the cookies and drain the bottle of milk.

Clare literally cheered quietly to herself as she watched Bill hungrily consume her proffered gift. Her milking done, she detached the suction cups from her relieved breasts, placed the collected milk in a small refrigerator she had upstairs and wrapped an elegant cream colored silk robe around her naked body, cinching it tightly with a red silk tie which accentuated her mature curves while leaving exposed an interesting expanse of cleavage. Slipping on red slippers she quietly descended her stairs, walked to the doorway dividing her apartment from Bill's and entered without a sound.

Bill snapped shut his laptop computer at Clare's abrupt and unannounced entrance.

Clare caught a momentary glance at its screen, chuckling inwardly, but decided to delay any comment on its content until later.

Instead she asked, "All set?"

"Yes, Ma'am," Bill replied, relieved.

"Did you enjoy my milk and cookies?" Clare asked innocently.

"Yes, Ma'am," Bill answered. "The cookies were great. But the milk was exceptional. It looked rather thin, but was very rich and delightfully sweet," Bill exuded. "Thank you. I'd like to have more if it's not too much trouble," Bill finished, smiling innocently.

"I think I can promise you that," Clare smiled warmly.

"Let's get you registered," she said, making for his front door with Bill happily in tow.

Crossing the parking lot and inspecting the well manicured grounds on the path to the Community Office, Bill noticed adults of all ages and sizes - variably clothed! Most were topless in the warm afternoon sunshine, including the women. Some were completely naked except for footwear, including the women. He tried not to stare, rightly believing it would be impolite. Young or old, men or women, clothed or naked they all seemed to know and like his landlady - smiling and waving at her.

Despite his best efforts, Bill's gaze lingered a bit too long on some of his now fellow inhabitants of El Dorado. Those he stared at were all voluptuous woman of middle age or better. His cock jumped slightly as he appreciated each one in turn. He noted with a certain pride - why he didn't know - that none of them were as attractive as the woman who was leading him thru the complex.

Clare noted his glances and his cock's behavior. She would instruct him on more 'proper etiquette' later. She was pleased however that his eyes always sought out women of her own age or older, not the many tempting 'young things' displayed through out the grounds.

Bill held the door to the Community Office for Clare. Inside he noted a dark haired, busty, middle aged woman behind a desk. The plaque on her desk read "Stacy", but Bill had a difficult time pulling his eyes away from her large, naked tits.

"I've found my tenant," Clare cheerfully announced as they approached Stacy's desk.

Stacy took a moment to appraise Bill, from top to bottom, conspicuously staring at his tented crotch before she responded to Clare, "Lucky you!"

Both women giggled like as Bill blushed crimson.

"Stacy, this is Bill. Bill, this is Stacy," Clare provided the necessary introductions.

Stacy extended her hand which Bill tentatively shook while he stared directly at her face, avoiding even a glance at her tempting breasts while he said in a quiet voice, "Pleased to meet you, Stacy."

"Polite isn't he?" Stacy directed her approving remark to Clare.

"And he better stay that way if he knows what's good for him," Clare added with a threatening laugh.

Bill just stood still, dumbfounded by his situation and the casual banter of the two middle aged, busty women.

"Clare, I assume you've outlined for young Bill here what will be expected of him in our community?" Stacy again speaking to Clare and ignoring Bill.

"Yes. And he agrees, don't you Bill?" Clare asked him.

"Yes, Ma'am," Bill replied, already being conditioned to automatically agree with his landlady.

"Good," Stacy responded. "Take this Permanent Resident Guest Contract to that desk in the corner, read it and sign it. Clare will witness your signature and I will notarize it."

Bill did as instructed, recognizing some of the provisions as mentioned by Clare, confused by others. He didn't bother to ask for clarification because he knew he would sign anything in order to become Clare's tenant.

Bill returned to Stacy's desk where the women were chatting as old friends - which indeed they were.

Bill handed the signed document to Stacy who said, "Because of the unique character of our community, I like to summarize what this contract means before finalizing it."

"Clare, as your sponsor, is responsible for your behavior and your possessions. You are, therefore, responsible to her. And therefore, you are allowed to remain in our community only so long as she approves. Do you understand and agree Bill?" Stacy asked seriously.

"Yes I understand and I do agree," Bill replied with equal seriousness.

"Good," Stacy said as she retrieved the contract from Bill.

She had Clare sign as witness and then affixed her notary seal.

"You'll both get copies in a moment. Now, let's take your picture Bill, get your photo ID, your 'regulation' El Dorado black COVID mask, your parking sticker and your internet information and we'll be all squared away," Stacy quickly continued, having registered owners and guests many times in the past.

Almost as quickly as she ticked off the list, all was finished.

"Thanks so much, Stacy," Clare said.

"Yes, thanks," Bill followed suit.

"You're both welcome. Come back anytime if your have problems or questions," Stacy offered Bill.

Clare and Bill then walked back to their home.

They entered through the screened in porch which served as the front entrance to Bill's apartment.

Entering his apartment, Clare locked the door and commanded Bill, "Strip and sit!" indicating the one chair in the room.

Without hesitation, Bill complied, slipping off his shoes and placing his clothes on the top of his dresser.

Sitting in the hard wood chair his face was level with Clare's tits, barely concealed by her silk robe.

Clare stared with apparent displeasure directly at Bill's pulsing, leaking, rigid member.

After a disturbingly long look Clare stated, "You must learn to control yourself if you are to live with me, in this community."

Bill looked with dismay at the rampant evidence of the sexual arousal he felt for the woman, some thirty years his senior, only a few feet away.

Returning his eyes to the sexy, stormy face of his new landlady, he pleaded, "But I can't help it."

"You can't control your own cock?" Clare asked with astonishment. Her own vaginal slit, now slick with the slimy juices of her own aroused pussy, suggested a certain level of hypocrisy in her question.

"Not with you Ma'am," Bill continued pleading.

"But you will be with me a lot," Clare stated the obvious. "Didn't any of your foster mothers teach you control?" she asked.

"One tried, but I guess she couldn't anticipate anyone as sexy as you," Bill responded sorrowfully, hanging his head in defeat, sure his indiscipline would torpedo his hopes at the last minute.

'Wait for it,' thought Clare as she watched Bill wrestle with his despair. He must think this is his idea.

The eureka moment finally hit him.

"You could teach me!" Bill excitedly blurted, jumping quickly to his feet in front of Clare.

"I could teach you what?" Clare asked innocently.

"You could teach me to control my cock," Bill continued in explanation. If Clare accepted his solution he was sure she would allow him to stay. And he so desperately wanted to stay!

"You want me to control your cock?" Clare deliberately distorted Bill's proposal to quickly reach the agreement she needed. She looked up past the rigid column of sensitive flesh which she was sure would provide her endless pleasure into his pale blue eyes. Please just say 'yes', she thought. She was impatient for her dominance of this handsome young man to truly begin.

Even as Bill said "Yes," he knew he was agreeing to a proposal subtly but substantially different from the one he had suggested. But Clare seemed on the verge of accepting him back into her good graces. He wasn't about to blow it now by quibbling over details. Besides, his sexual need was now so acute he knew he would agree to almost anything she demanded.

Clare too was tired of talk, wanting to move quickly to the training of this handsome, naïve young man.

But there were still some important details for Bill to agree to.

"I can be a strict, even cruel teacher," Clare warned, "I will require total honesty and complete obedience from you, Bill."

Pressing her advantage and not allowing Bill to ruminate too long on her demands, Clare quickly grabbed Bill's throbbing cock just below its now slippery head with her right hand and closed her left around his aching nuts as she declared, "OK. At YOUR request. I accept control of your cock, your balls and your sexual behavior. Is this what you want, Bill?"

A strangled "Yes" emitted from the aroused and relieved young man.

Clare scraped her right middle finger nail across Bill's bloated cockhead, collecting a dollop of his glistening precum. Locking eyes with the amazed young man, she slowly raised it to her mouth, inserted it deeply, and closing her generous lips tantalizingly sucked it clean.

Bill moaned. He had never seen such a deeply depraved yet sexy action.

Clare could feel his balls tighten. She released Bill's scrotum and said, "You will not cum without my permission."

"Yes, Ma'am!" Bill affirmed.

"Sit, Bill!" Clare commanded.

Bill plopped his ass instantaneously on the hard, wooden chair seat.

With a mischievous smile Clare knelt before the adoring young man, her robe opening slightly to expose more of her abundant tit flesh, her wet lips approaching Bill's aching dick. She began at its base and began to slowly lick its underside. The heat, wetness and sensation stunned Bill.

Clare continued to lave his turgid member slurping down noisily every drop of precum she could find.

Bill looked down in worship at the woman who was willingly giving him such pleasure. Then it increased!

Clare broke eye contact so she could concentrate on his prick. It was beautiful, hard, straight and thick. His precum seemed to flow like a small fountain from his cockhead's wide hole.

She raised up slightly and pulled his polished dome down slightly as she placed her lips on its tip. She began to slowly engulf his rod as Bill sighed. It was almost more than he could take. 'Do not cum,' he reminded himself as Clare's lips stretched to encircle his head at its base.

There she paused a moment to accommodate her jaws to his size. She also began to lick his entrapped cockhead with her tongue, sending a deep shiver of pleasure thru Bill's body.

Clare resumed the slow consumption of his cock, sucking more of it into her gaping mouth and widening throat in an undulating, rhythmic pattern which almost cost Bill his last shred of control.

Though no virgin, Bill's relative sexual inexperience had not prepared him for the exquisite pleasure Clare was so skillfully producing. He shivered. He moaned and even a rare tear welled in his glazed eyes.

Clare chanced a quick look up to gauge his reaction. She smiled around his now pulsing penis - she knew she had him trapped! His own increasing erotic bliss ensured he was bound to Clare.

Clare's entire head lowered even further into his crotch finally impaling her throat with the full length and breadth of Bill's manhood. She gagged slightly, then began a slow, rhythmic swallowing of his sweet tasting meat.

'Don't cum without permission!' Bill panicked as he recalled her condition - to which he had agreed! He looked down to see Clare fully engaged in giving him a full bore blow job.

Bill was in an agony of delight and conflict.

"May I cum, Ma'am?" Bill pleaded in desperation.

Clare heard the anguished request and would have smiled broadly at his dilemma if her entire face wasn't distorted by Bill's impaling member.

In answer, Clare opened her mouth and abandoned Bill's rigid pole, wet with his own precum and her spit.

She rose from her knees to stand before him and with a cruel smile answered, "No you may not cum. Stand up."

On shaky legs Bill lifted himself from the chair. Looking down he realized for the first time how he towered over this small, middle aged woman whom he adored.

Clare took his place on the chair. She spread her tanned thighs to reveal her wet, hairless pussy. She looked in Bill's pleading eyes and nodded her head slightly.

He fell to his knees before looking up into her deep, knowing large brown eyes.

"Kiss me!" Clare demanded as she further spread her thighs to accommodate Bill's body. His knees scraped the floor as he eagerly approached, raising his face to accept her kiss.

For Clare was the sexual aggressor. She held his head firmly in her small hands and attacked his lips with hers. She quickly pushed her tongue past his lips and deep into his mouth as he helplessly surrendered to his landlady. He tasted his own residual precum for the first time on her lips and tongue. After establishing her dominance with a single passionate kiss, she broke it off abruptly and pushed Bill back on his heels.

Clare leaned back and generously spread her legs further allowing Bill an uncluttered, open view of her pussy. She watched closely for Bill's reaction to her now exposed sex.

Bill had a vision of the smooth, shaved, puffy with excitement, glistening pink ragged folds of her flesh. Her lips were beginning to open in anticipation of his attention. He was ensnared by its heated beauty and entranced by her sweet musky fragrance. Beginning to emerge from the very top of her sacred sexual slit, from beneath its protective hood was her clit - pink, insistent and growing.

To Bill's amazement it continued to grow until it emerged deeply pink, hard, commanding and larger than her outsized nipples! His face reflected his astonished lust.

Clare gazed down with satisfaction - another man hopelessly ensnared by her cunt, her clit and her rampant sexuality. She allowed Bill the pleasure of a long, uninterrupted scrutiny of her pussy.

Bill took advantage by moving his face closer to her twat and noting the swollen, ragged lips moistened by her flowing nectar. It's folds were irregular, undulating in the palpable heat emanating from within its dark depths. It occurred to Bill that this was a used pussy - used well - used often - used for a long time - since long before he was born!