Babysitting Emily

Emily stepped alongside Sam as he led her by the hand up the stairs. Her short skirt fluffed at each tread as she sashayed up the stairs, flashing her panties to the upskirt watchers in the foyer below. At the landing, they turned out of sight and traversed the short hallway to a spot where Sam motioned for her to enter one of the bedroom doors.

It was a fine bedroom setting with a girlish décor: pink bedspread on a broad queen-sized bed, pink sheer curtains, and lacquered ivory-toned wooden furniture.

"Your potential new home, Emily. Debbie has moved out and this could be your room now."

Sam let her view her likely new living space before turning her gently by the shoulders to face him. He plucked at her blouse buttons and spread open the lapels.

At her friend Debbie's advice, or rather insistence, Emily had come to this impulsive tryout braless and the man's eyes widened in admiration at the sight of her broad brown nipples on her well-rounded breasts. It seemed his hands couldn't help but return to cup and squeeze them, this time bare skin on bare skin.

Sam was pleased. Yes, her tits were real; a nubile firmness with just the modest sag, despite her age and feminine form, it was expected from such large masses,

She arched her back to let the blouse slip down her arms, the motions pressing her tits forward, helping him get more tactilely acquainted with his latest playthings. She really wanted to fit in here. Her scholarship and visa were at risk and she needed Sam's backing. She calmly let him misbehave as he liked.

He idly whispered for her to keep going. The skirt followed the blouse to the floor, and when she tilted forward to lower it, his hands followed their course and pattered her dangling boobs upwards and sideways, bouncing and swaying the fleshy masses. She watched his hands play before straightening upright.

She stepped back from his fondling caresses, moving to sit on the chair, intending to remove her mid-height heels. But he took her arm and kept her standing. She stood before him in half-naked splendor and heard his quiet command.

"Please kneel."

She did, which placed her face at his waist level. She watched as he unzipped his fly and extracted his cock.

Emily was no stranger to the male anatomy. Her Manila hometown was a hotbed of sexual caprices and her clique of girlfriends were regular disco club carousers. Seeking collegial adventure rather than money, she had mirrored her older friends' notorious mimes, and like them, on occasion, in dark corners or parked cars out back, astounded the curious worldwide tourists, gamely sucking some cocks and fucking others. She just wistfully adopted the deferential females' roles that were ubiquitous in third-world street cultures. The submissive mindset came back to her now, in Sam's house, in Sam's guest bedroom.

Without further guidance from him, she leaned in, kissing the tip with a slit poking tongue-tip, as he held the shaft in his hand. His other hand touched the back of her black-haired head and, recognizing this frequent maneuver, she obediently opened wide and engulfed the offered mouthful of man-meat.

Emily sucked him gently, achieving the activity's accustomed consequence of his manly muscle swelling in her mouth. She was a bit nervous about the bulk of this muscle that would presumably, sooner or later, be probing her cunt. She bobbed obediently, leaving him to decide whether to spew here or use her cunt.

Sam decided on cunt. He lifted her to stand and pressed her towards the bed. She turned to continue and kneed aboard; her ass rocked as she moved away from him. He grabbed her panties and pulled them off her legs and over her heels, twisting her over on her back by a firm grip on her shoed ankles. Her hair flailed out to form a wreath of black mane about her head.

He pocketed the thong panties, his 'first-time' souvenir, and then doffed his own clothes, noticing her watching him disrobe. Her face was stoic, calmly waiting for him to assert his male privilege.

Emily opened her arms and legs to accept Sam as he climbed on and boldly placed his saliva-slicked erection against her moist pussy. She braced her sharp heels into the bed as he paused to steady his knee-borne stance above her body. Ready to rumble, he dropped down and pressed in, stretching her to the core with one long slow glide to paradise.

She moaned urgently at the fleshy expansion; he paused at the bottom to let her strained vaginal canal adjust. She bumped his groin with her clitoris; a sign that she was ready to be taken. He knew the routine and, settling into a snug conformity, he stroked within as she assisted his pleasure by rolling her hips.

Sam set the rhythm and stroked steadily. He used her at his pleasure and gained a wonderful orgasm.

After he spurted, groaned, and collapsed, Emily felt his kiss on her neck and his nuzzle in her ear. Emily felt happy with those sure omens that she had earned her rightful place in her friend's mixed family.

-----------

Sam's head rested on a plumped-up pillow, looking down across his bare belly. Emily's dark eyes, peeking beneath the eyebrow length straight cut black bangs, peered back at his; her lips and tongue actively caressed his orally embedded cock.

She had been resident in his house only a week but had taken well to her designated function of worshipping her Daddy's cock.

Sam blew her an air kiss and twitched his head, his way of telling her to slide up his legs and mount up on his sturdy hard-on. She sat upon his legs and waddled her crotch forward, contacting his belly-flopped erection with her juicy labia, smiling at her next intention. She liked to tease and tented her pussy lips back and forth along his exposed genital rod, each time grazing her clitoris on his under-vee.

Sam had become fond of this particular initiative, letting her soft wet labia tease him but only for a while. With a growl, he hauled her body down on his, pressing her boobs to his chest. She wiggled her ass around until she found his knob, pressed down, and glided his cock inside her cunt.

As his rigid cock lay emersed inside her, she kissed his lips, suckled his neck, and found his ear, moaning in her own pleasure at the intimate connection and its inevitable sensual summit.

Sam felt her stiffened tongue probe his ear canal and his cock jumped at the reflected stimulation. She snickered on feeling the flex, whispering in his ear.

"I felt that."

He mumbled his acknowledgment and she pressed his ear canal again. Another jump thrilled her core. She untangled from his hug and sat up, gaining her balance for the impending vigorous cowgirl ride.

She humped his hips as he played with her swaying tits. He was amazed that she was so petite in body and yet so big in boobs. She had a snug cunt but it was long and deep; incredibly she always managed to stuff his huge erection all the way inside her.

Her ass and hips moved with adroit dexterity; her fabulous energy unrelenting. As always, her efforts rose to their finest and he came hard. She continued her carnal stimulus throughout his euphoria, slowing to a halt only when he fell out, happy to have made him happy.

And the weeks melded into happiness for all the home residents. Unfortunately, money reared its ugly head. Sam liked his strip club bouncer job but he had always intended its salary to support his modest solitary lifestyle. He tried but it was a stretch to support himself and three feisty female housemates.

During a post fuck cuddle in Emily's bed and arms, Sam asked her about school.

"How is school going? Getting good grades?"

"They're fine. I do the classes and homework just like the rest but Mr. Jones can be a bit of a drag. So, I worked for extra credit to improve my marks."

"Extra credit?"

Emily leaned up to his ear and whispered with a giggle.

"I let him score my pussy..."

Sam was a bit alarmed by the revelation. He had assumed with Emily being home every night, including weekends, that she fucked exclusively with him. Now he learned that she resourcefully advanced her interests as she saw fit. Not a bad thing, just a surprise. And an idea began to percolate in his mind.

"Tell me about it."

Emily related how she had sought an office-hours visit with the grey and balding stodgy professor. Inside his closed office, she had sat across the desk from him. He watched from behind his desk as she stumbled through a plea for curriculum leniency. Her animations gave her the opportunity to garner his attention with surreptitious flashes of her panties, girlish giggles, and a coy nip slip. When she saw him flush and wipe his brow, she knew he was vulnerable and crawled up and across the desktop to plop into his lap. He weakly protested until her hands tunneled between their legs and dug out his cock.

The senior man was too smitten to resist any further and she rode his modest erection to a quickie ejaculation. In post-coital recovery, she whispered suggestions of periodic sexual frustration deflations in exchange for periodic classwork score inflations. He wearily agreed to the deal with the added mutual assurances of secrecy.

Over the next few days after hearing her story, Sam pondered his financial situation and sought advice from his friend, Tony, the city alderman. Could he find some extra side hustles for Sam to supplement his income?

The wheeler-dealer politician knew everyone who was anyone in his circle of influence and happened to have a dilemma for which Emily, rather than Sam, might be a perfect solution. A development he was invested in needed permits and the mayor was stalling. The mayor also had a penchant for out-of-town junkets and had hinted to Tony about procuring him a suitable willing escort for the coming weekend.

Even with the offer of monetary influx, Sam had concerns but the alderman assured him the mayor was a pussycat and Emily would come to no physical harm, probably just carnal fatigue. They laughed off the latter as a passing inconvenience for the vibrant coed and agreed to the advantageous arrangement. Sam said he would vaguely brief Emily, hoping the impetuous caper would pique her sensual curiosity.

Towards the end of the week, Tony showed up at Sam's home. Upon introductions, the liaison broker saw the nattily dressed Emily and wholly concurred with her choice of flirty travel apparel. Set to depart with his deal-making gratuity, he accepted a small satchel from his friend.

"Some extra things for the weekend."

Tony took the bag unopened and nodded, trusting in Sam's affinity for temptation. Taking Emily's hand, he led her to his car, her other hand trailing the roller case. She was off on her impulsive jaunt to ply her skills for some fun-filled days.

During the intervening time, Sam busied himself with Maggie and Candi who enjoyed the extra attention. When Emily returned several days later, she looked somewhat tousled and worn, slowly recovering from her 'passing inconvenience'.

Sam wanted to hear the details of her adventure, but first things first. Maggie was magnificent and Candi was dandy but he still missed his sexy little Oriental plaything and eagerly took her to bed for a hearty 'welcome home' suck and fuck.

Partly assuaged of his sexual tensions, he laid in post-coital contentment, plumping Emily's fat boob, as she idly played with his flaccid cock.

"So, how was it?"

Emily took a deep cleaning breath and, with a bit of recollecting pause, launched into her narrative. Sam listened as she relayed the details and fingered his cock.

Tony had driven her to the airport. In the ticketing lobby, he introduced her to the mayor. The man was stiffly polite, still dubious that this long-anticipated hedonistic weekend was really happening. The last time Tony had stepped up for the mayor, he had hired an over-the-hill chain-smoking hooker. But not this time.

His 'date' was a knockout: nubile, fresh, busty, wearing well-appointed fashions and accessories. The bodycon dress with its cleavage keyhole cutout was a masculine eye magnet. If their eyes scanned elsewhere, they admired her perfect makeup and jewelry.

"Emily, this is our mayor. He's a VIP, so treat him well. Be a good girl, okay?"

"Okay, Uncle Tony."

The mayor's face shot a look of mild surprise. Uncle? Had Tony provided a member of his own family? He was aware of Tony's rumored condo-sited coed and had thought she might be the one accompanying him. But he knew Tony was not into willingly sharing his personal treasures; all the same, the mayor was just fine with this other fine-looking lady.

"Here's my club guest pass. One evening only, so make the best of it while you're there."

The men shook hands and the mayor lightly held the girl's hand, carried the 'extra things' bag in his other, and led her to the boarding gate.

The TSA guards queried her separately about the different last-named older fellow but she brushed off their concerns with a reasonable explanation: a civic-sponsored scholastic outing. The screeners looked at the quirky couple and shrewdly deduced that certain anatomical lessons would be part of the young lady's syllabus. They let them pass unhindered, wishing them well. Some guys have all the luck.

They boarded first-class and winged away to the distant private resort. The passengers and crew furtively gossiped about the VIP with his deliciously dressed much younger traveling companion.

They arrived late in the evening, and after a room service supper, Emily wanted to freshen up. The mayor waited until he heard the shower sounds. He crept to the bathroom door and peered inside. The rounded Pinay was visible through the glass enclosure, water dribbling down her fine figured form. She caught sight of his ogling face in the doorway and turned seductively to give him a full-frontal show. Her hands rubbed the soap suds over her breasts and pussy, decorating her assets with foamy bubbles. He smiled and nodded and left to wait for her in the main room.

She emerged in a bathrobe, her hair in a turbaned towel. There was nothing unclear about the purpose of her trip with the older chaperone and she proceeded to get things rolling.

She approached the mayor, untied the cotton robe belt, letting it split open for a coy exposure of her squeaky-clean cleavage and freshly shaved cunt. He sat on the edge of the bed and she took charge of removing his shirt, shoes, and pants. The boxers dropped away to reveal the first view of her weekend focus.

She dropped her cotton robe and sidled up to sit on his lap. She pulled his head to her breasts and felt the nice tickles as he kissed and bit her nipples. She pushed him on his back on the mattress. She would drive the action for now. Emily spent the night sucking and fucking her host, a get-to-know-you session that almost drove him into exhaustion.

The next day, the tuckered mayor paced himself. They lay on pool deck lounges, Emily wearing one of Sam's 'extra things', a white bikini that was at least one, maybe two, sizes too small. The packed swimsuit was bulged full of her big boobs and camel-toe crease.

The mayor tried to behave himself, avoiding overt staring like the other men in attendance. But he finally succumbed and took her to the room for a 'quickie nooner' relief break, judiciously saving his remaining vigor for their planned nighttime carousal.

As evening fell, the mayor informed his young guest that they were going disco dancing at a special local club. He wanted her dressed to impress and knew how to do it.

This time, he joined her in the shower. The bathing pair shared the soapy chores, working the scented lather into each other's skin. He advised her post bathing preparations, coaching her on facial and feminine zones cosmetics. She applied dark eye shadow and liner to deepen her brown eyes, an alluring look for the dark disco venues.

He denied her stockings but unexpectantly produced spiked dancer heels, drawn from the 'extra things' satchel, along with a shimmery silver lame sheath dress.

As he helped her don the sexy disco dress, she realized that she couldn't wear a bra or panties. The short hem, high leg slit, and side boob exposures of the loose draping fabrics barely concealed her body, only enough to avoid a major affront to public nudity laws. Lingerie would spoil the effect.

He stood her before a tall mirror, her bare back exposed by the openness of the dress pressed to his front. She watched the reflection calmly as he tested the dress's advantages by fluffing her tits from outside the dress, then tunneled beneath the sides to heft her boobs in bare hand captures. He cupped her tits and saw the telltale pokies dot the otherwise smooth fabric. He gave little bounces and watched the shimmery bodice ripple. Even Emily smiled at the sexy show, knowing any body movements would generate wavy eye magnets for all to see.

A modicum of silver jewelry, including a chain woven choker at her neck, completed her lascivious presentation. She looked one last time in the tall mirror at the total package. She knew she would attract the envy of ogling men which would boost the ego of her host. She would take advantage of his arousal when they returned from their dancing soiree for another night of passionate sex.

Satisfied with her appropriateness to their pending venue, the mayor walked her through the hotel lobby to a waiting car. As designed and expected, her high-heeled stride bobbled her pokie-adorned breasts, fluttering the loose shiny covering. The mayor's peripheral vision perceived her eye-catching display as she bobbed and shimmered past gaping guests and bellhops.

They rode through the street-lamp-lit avenues until the car pulled up to a modest marquee, announcing the Devil's Den Disco. The mayor produced Tony's guest pass and security passed them through. They entered the disco's neon glowing main room; some girls and boys were bopping on the dance floor t thumping disco beats under the flashing strobes. The mayor passed by the surrounding lounge booths, looking for an unoccupied space. On his circuitous route, he acknowledged the other men's notice of the prime piece of ass he was chaperoning.

Emily noted the similarly provocative attire of the other women, both on the dance floor and ensconced in the deep booths. Her mind flashed a moment to memories of the Manila clubs of her youth and those images rekindled her naughty sense of mischievousness.

Between drinks and finger food, she danced and discoed through the evening, drinking sparingly. The mayor couldn't match her energy and sat out many dances while she saucily bopped and boogied in her mini-outfit with a small group of likewise neglected companions.

A touch inebriated, Emily trifled her chaperone with flirty skin flashes, annoyed by his distraction to the other females. He seemed to enjoy her flaunting her beauty and vitality while he lecherously ogled the other women with a notable growing interest. He and his cohorts laughingly enjoyed the flirty side-boob and ass flashing spectacles.

At midnight, the neon strobes lights abandoned their staccato beats and the music turned to more easy-going tempos. The younger patrons left for livelier all-night clubs. Staying behind were a dozen or so couples, the majority of whom included the provocatively dressed women and older men.

The mayor danced with her in slow tempo, a hand clutching her ass with her hand in the other.

Emily, feeling the effects of the alcohol and vibrant dancing, was now mellow in his arms, ready to return to the hotel and find the sexual relief she wanted. She murmured in the mayor's ear.

"Please... Let's go now... I need to be fucked."

"Yes, you do..."

He unwound his arms and she stood next to her patron, ready to follow him out, sashaying lightly from foot to foot, impatient to be going.