Bareback Bar

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A young woman shepards three milfs.
4.5k words
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The Proxy

It was a steamy night in the city when Anna happened to spot Lila sitting at the bar of a crowded nightclub filled with so many handsome strangers. Anna and Lila had forged a friendship a year or so ago, during a steamy night out, the first time Lila went out since her breakup. Since that breakthrough night the two of them, even though almost two decades apart in age, became inseparable every time they met.

It was clear that Lila was waiting for company but that did not deter Anna from being mischievous. Anna, ever eager to tease, approached the first cute guy and suggested a playful prank on Lila. She told him to stand behind Lila and press his member against her. Anna promised that she would come right behind to clear the situation up.. She wanted to set the scene up for a playful reunion with Lila - who she had not seen for weeks.

The guy, amused by Anna's suggestion and excited by the prospect of "meeting" Anna's intriguing friend, agreed to be part of the prank. She broke the stranger's dormancy with a pat on his cock and a push on his buttocs! He reached Lila and pressed his member against her, the shock and confusion on Anna's face were evident in her sudden turn of her head and the widening of her eyes. However, true to her word, Lila quickly jumped in, laughing and hugging her friend as she revealed the playful setup. Anna, surprised by Lila's bold prank, couldn't help but laugh along and playfully scold him for the mischief, invitingly slapping his member with her palm for the second time tonight!. The initial shock melting away, Lila shared a knowing smile with Anna; this playful encounter only made her more eager to spend the night catching up and having fun with her adventurous friend. Anna's graduate studies were of great interest to Lila, sharing the same subject that she had studied; she was some kind of mentor to her.

It was amazing how Anna could jump from her graduate studies to the carnal on a dime! This is one of the reasons Lila was so attracted to Anna, for her energy, for being so full of life. Anna turned to Lila, a playful glint in her eye, and explained that since the club was packed, a little innocent penetration would hardly be noticeable - and might even prove to be quite pleasurable...

With the memory of the stranger's slightly engorged member pressing against her derriere still alive Lila agreed with Anna:

"If you bring him, I can be ready"

said Lila sitting at the bar, the crowd now pushing the two friends together, the space becoming denser and to the two friends the right field for their planned escapade. Without much ado Anna captured the guy's attention again and somehow convinced him to make the daring move. Lila, thankful for the mini skirt she wore tonight, mentally rehearsed lifting it to provide access. Sitting on the bar stool made for a perfect setup. And perfect setup for this crowded space meant opening up her forbidden entrance. All she would have to do is lean forward a little (maybe reaching for her drink on the bar?), lift her skirt, part her lace panites and allow him to breach her anus. The crowd and the placement of Anna would provide the necessary cover. Lila ordered two glasses of Sauvignon blanc, coyly parted her panties with her skirt providing the necessary coverage, leaned against the bar top and waited.

Meanwhile, Anna approached the guy once again with a sultry smile. Intimately leaning in close, she whispered their plan, her breath tickling his ear and igniting his curiosity and desire. Surprisingly intrigued, the guy agreed to the proposal, watching Lila delicately perched on the bar stool. To prepare him for the encounter, Lila skillfully unzipped his pants and gently stroked him, ensuring he was sufficiently hard and ready. Meanwhile, she discreetly searched the bar for a suitable lubricant, and her gaze landed on a small bottle of coconut oil used to prepare exotic cocktails. She grabbed it and, with a sly wink, applied a generous amount to the guy's engorged member paying a lot of attention to his head.

All this time the three of them engaged in playful conversation, laughing, asking questions, being downright social. Underneath the surface of the crowd, Anna took a little more of the oil and lifted Lila's skirt, depositing it on the entrance to her clenched anus. A slight spasm of Lila's to her touch spoke volumes of what was to come

In the meantime, Lila decided to attract the attention of a nearby group to provide some distraction and cover for the situation unfolding at the bar. She engaged them in conversation, laughing and sharing drinks, all the while keeping a watchful eye on Lila and the young buck. With her skirt lifted just enough and a slight parting of her lace panties, Lila subtly angled herself, giving the guy the access he needed. As the hum of conversation and music filled the air, he cautiously moved behind her, pressing the tip of his lubricated member against her well-oiled entrance. The anticipation sent a shiver down Anna's spine, this thrilling adventure already surpassing her expectations. Feeling the pressure, Anna slowly relaxed and allowed herself to be breached, her body enveloping him in her warmth.

While it took a long time of teasing, pressuring and probing her portal, his head slowly pushing inside her, he suddenly breached her. In one continuous push he was inside her, enveloped, constricted, owned by her. As they began their discreet, public escapade, the pair moved in harmony, his movements timed with the beat of the music and the natural sway of her body, skillfully masking their intimate act. Lila continued to entertain their small group, a knowing smile tugging at the corners of her mouth as she relished the secret unfolding just a few feet away.

As Anna approached Lila, who had just stood up after her daring adventure, she couldn't help but notice the excitement still lingering in her friend's eyes. She walked closer to witness Anna delicately holding a napkin, catching the fluids left behind from their recent encounter. As she adjusted her miniskirt and lace panties back into place, she checked her makeup in her little purse mirror, her flushed cheeks a testament to the passionate moments they had just shared. Opening up her purse, Anna reached for the oil and put some on her friend's two fingers:

"Soothe your portal, you might have to use it again, tonight" she said to Lila with a wink

2+2

A few minutes later Sarah and Dalia, showed up for their rendezvous with Lila. They were in their mid forties, same as Lila; friends since they were studying for their MBA's. Lila in turn introducted them to Lila with a warm smile. The ladies greeted one another cordially, and as they were from different social circles and age groups, they started to get to know each other, asking the obvious and the naughty questions too!

Sarah's eyes, still fresh in the club, darted across the room and locked gazes with a handsome young man leaning against the bar. The flirtatious glances they exchanged brought a mischievous smile to her lips and, feeling a bit tipsy, Sarah proposed that youngling Lila show these three milfs how young people move on the dance floor. Sensing Sarah's interest in the good-looking stranger, Anna understood that just like Lila, Sarah too was seeking fun and adventure in this girls' night out. She could also tell that Sarah, being married, was hoping Anna, being young and free spirited, would take the initiative and help break the ice with the attractive man across the bar.

Eager to show them a good time, Lila guided the ladies onto the dance floor and began instructing them on the latest moves. Gradually, their movements became more sensual and provocative, drawing the attention, admiration and desire of others in the club -- including the handsome stranger Sarah had been eyeing. With the atmosphere more charged as they danced, Anna grinned conspiratorially at Sarah, subtly nodding towards the young man. Giving her a wink, she let Sarah know that she would help make her playful fantasy come true, if only for a night..

As the four ladies took a pause from dancing, Anna motioned for the handsome stranger to join them at their barstools. With Anna's arm wrapped around him, she guided him back to their little corner at the bar, where Lila, Sarah and Dalia eagerly waited. As they reclaimed their spots at the bar, the stranger found himself casually sandwiched between Sarah and Anna. The enticing combination of alcohol, music, and the vibrant atmosphere fueled Sarah's confidence who couldn't help but slowly and deliberately brush her fingertips against the stranger's forearm. Every time their eyes met, suggestive, playful, and secretive smiles were exchanged. The stranger, clearly enjoying his fortunate luck at being surrounded by such intriguing women, responded in kind by subtly shifting closer to Sarah as they talked and laughed. In an even bolder move, Sarah got up from her stool and began swaying her hips to the pulsing beat of the music, gently and intentionally rubbing her backside against the stranger's bulging crotch. She could feel his growing interest in her, and this titillating action only intensified the atmosphere of excitement and dash exhilaration among the group.

As Anna sensed the building chemistry between the handsome stranger and her new friend, she realized it was time to take the situation to the next level. Drawing on Lila's daring experience from earlier in the evening, she turned to her friends Lila and Dalia and mischievously whispered that perhaps they could encourage Sarah to escalate the encounter with the stranger; all of them surrounding the pair discreetly to protect their secret. In order to prepare Sarah for what she was about to propose, Anna subtly opened her purse, ensuring that the half-empty bottle of coconut oil was visible to their conspiring eyes.

Sarah's eyes sparked with excitement and anticipation. As she caught sight of the coconut oil her heart started racing. Wearing a form-fitting, dark blue dress with an asymmetrical neckline that draped alluringly across her collarbone, leaving her other shoulder bare she felt sexy and desirable. The slit on the side of her short dress allowed for ease of movement while revealing her toned, tanned legs peeking under the hem, the atmosphere electrified as she sashayed around the bar stool.

It was time Anna spell out her daring plan, she knew Sarah would be more than willing to follow the course set before her. The flirtation between the ladies and the stranger intensified, making the air thick with desire and anticipation as they prepared to take their thrilling adventure to the next daring level.

Sarah sat on the barstool, while Anna quietly passed her the bottle of coconut oil. Lila and Dalia were tasked to keep the stranger, still oblivious to the upcoming surprise, engaged in conversation. Meanwhile, Anna cunningly and discreetly lifted Sarah's dress, just enough to gain access to her miniature silk panties and tight clenched anus. Starting to apply the oil, she surprises Sarah who turned slowly to face her, a look of owe and desire in her eyes, trying to relax her rear muscles for her new friend. She pushes more to the back towards Anna, noticing her friends making a circle around her, keeping prying eyes from what was unfolding underneath.

Once the preparations were complete, Sarah stealthily gazed at the the young man, his eyes caught her seductive glint, his curiosity and arousal peaked, as he found himself drawn deeper into the thrilling unfolding adventure.

Under the guise of playful banter, Anna coaxed the stranger to move around the bar while unbuttoning his pants. His gaze was fixed on Sarah, who charmed him with her flirtatious words and inviting seated pose. As Anna loosed the the stranger's pants loosened and caught hold of his throbbing erection, Sarah turned her back to him, it was time. Seated and provocatively angling her luscious derriere she glanced over at Anna, who gave her a knowing nod, signaling that the time had come. Feeling the oil on her hand, Anna carefully led the stranger's tip to make contact with Sarah's well-lubricated and tightly shut sphincter. As they maintained their conversation, the stranger's breath hitched for a second upon feeling the incredibly warm pressure against his cock. His eyes widened in surprise.

He felt her buttocs pushing against his pelvis, the tip of his manhood against her sphincter, her clenching, the small spasms, her first attempts to receive him. The pressure of his head against her anus was what was real now, what was connecting them. She relaxed, feeling him slowly opening her up, first the light at the end of the tunnel, then a little more and suddenly, effortlessly, she took him all in, he was hers, completely. The friends encircled the mating couple engaging in lively conversation while distractedly shielding the sensual act from the surrounding crowd. The stranger found it difficult to concentrate on their words as his partner enveloped him, constricted him, fueling his primal urges. As the friends continued chatting with the stranger, making a show of normalcy, his climax built inside him. Unable to contain his ecstasy any longer, he grunted softly and released his seed into Lila's welcoming rectum, leaving her yearning yet surprisingly content.

Back entrance revisited

Their wild adventure had not gone unnoticed. Across the bar, two men stood observing the group with intrigued expressions, clearly drawn by the group's daring acts. They smiled at Sarah, sending over martinis for her and her friends as a silent invitation to continue their risqué adventures. Anna, noticing the drinks and the men's appreciative gazes, decided to take on the role of the agent in this round of their thrilling escapades. She donned the most seductive smile in her arsenal and subtly gestured for the men to join their group. As Shara took a slow sip from her fresh martini during the brief intermission, the newcomers approached and whispered to her conspiring friends their intentions to share the same forbidden pleasures. The group of friends, excited by the prospect of expanding their daring encounters, discreetly surrounded Sarah once more, embracing the shared thrill of their unconventional evening. One after the other, the two new men indulged in her overflowing, cum lubricated rectum, each breaching her a little easier than the previous one, reaching their own climaxes, paying their dues to her womanhood.

Sarah couldn't help but feel the wetness from all of her previous encounters pooling on the leather stool beneath her, a messy, and erotic reminder of her recent taboo trysts, causing a wicked grin to play across her lips. After satisfying the desires of three men, after claiming all three of them, Sarah felt the need to freshen up. With a sly glance at her friends, she excused herself from the group and made her way to the bathroom, wobbling slightly from the intoxicating combination of alcohol and sexual euphoria. As she entered the restroom, she caught a glimpse of herself in the mirror. Her tousled curls framed her flushed face, her lipstick slightly smeared from all the heated encounters, while her dark purple dress clung to her body, showing off every curve. She couldn't help but feel incredibly sexy and empowered by her recent experiences. In the privacy of the bathroom, Sarah carefully removed her soaked lace panties, discarding them in a nearby trash bin. She then took some paper towels and, given the circumstances, cleaned herself as best as she could. Determined to return to her friends and continue their naughty adventures Sarah strutted back to the bar, her bare, gapping and leaking forbidden entrance hidden beneath her now damp dress.

Change of guard

As she rejoined her friends, she couldn't help but notice that Dalia had taken her seat at the bar stool. Without much explanation, Sarah watched as Dalia, married and all, wiped the mixture of men's cum and her own feminine arousal from the leather stool using her hand, licking her fingers clean with a devilish grin. The sight sent a thrill of forbidden excitement rushing through her. Dalia's dress, a sleek black number that outlined her voluptuous curves, provided easy access for anyone daring enough to try for an impromptu and illicit rendezvous. The v-neckline plunged just enough to reveal the lace edges of her bra, while a suggestive slit up the side of her skirt hinted at the sultry lace panties carefully chosen for this evening out. It was clearly her turn, she was yearning for it.

Catching the eye of an attractive young man who appeared to be just fresh out of his teenage years, Dalia couldn't help but feel a surge of excitement. With an air of authority and desire, she whispered instructions to Anna, asking her to bring him over. Dalia saw the advantage of using the young man's inexperience to satiate her thirst for another less time-consuming encounter. As she glanced around the room, she couldn't help but think that he wouldn't be the only one to fulfill her desires that evening.

Doing as instructed, Anna approached the young man and seductively lured him back to their corner of the bar. The moment he saw Dalia, his eyes widened with nervous excitement, realizing that this night held a daring adventure he could not possibly have anticipated. Dalia, forgoing emotion, all carnal and primal pleasure in her body, positioned herself with her back to him, setting her trap, ready to claim him. Anna fished the almost-empty bottle of coconut oil out of her purse and while the friends were distracting the young man she squeezed the contents in a most perfunctory way in Dalia's rectum, this was the business of women claiming men, devoid of emotion, guttural, full of desire, carnal.

Taking her turn, Lila, helped Dalia position herself on the barstool and discreetly lifted her dress, making sure her voluptuous form was accessible for the impending pleasure. With Lila's tight and eager anus exposed from beneath her black dress, Dalia guided the young man towards her. Though inexperienced, the young man was thrilled and eager to please Sarah. Filled with an anxious mix of excitement and nerves, he made contact with Sarah's well-lubricated entrance, unsure of what to expect. At this point, it was up to Dalia to take control and make the encounter the memorable and thrilling experience she craved. Feeling the young man's pulsating but unlubricated tip pressing against her tight passage, Sarah took a deep breath and slowly pushed back. She relished the sensation of him opening her in stages, her muscles pulsating, opening up a little at a time, clenching and releasing again, his head finding more and more of that enabling oil inside her until finally...his head puushed all of her defences aside and dove deep inside her, all in one slow steady motion. She began to rock against him, the motion protective and discreet. The friends continued their casual conversation, expertly shielding the pulsating encounter from the curious gazes of the surrounding crowd. As the secret tryst progressed and the young man struggled to maintain his composure, he couldn't help but notice Dalia's wedding ring as her hand gripped the bar. The sight only intensified the raw excitement coursing through him. With the reality of their forbidden encounter coupled with Sarah's alluring movements, the young man finally succumbed to his climax.

The excitement in Dalia's eyes was undeniable as the young man withdrew, leaving her filled with the thrilling sensation of their shared experience. It was her turn to fell the youthful energy and hunger for more adventures, separating her married self from her carnal sef. Her friends, eagerly in sync with her desires, glanced around the crowded nightclub, wondering who would be their next conquest of the evening. Lila, her unspoken aid for this part, discretely wiped Dalia's soaked area with a wet napkin, cleaning up any remnants of her latest exploits. The ladies whispered and giggled among themselves as they scoped out the next candidate for their friend.

12