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A Very Good Friend

"Sometimes, you just need a little kick in the ass..."

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The local salon had been good to Caty. At thirty-seven, she had built up a nice clientele, and enjoyed the time with her customers. A down-to-earth soul, she enjoyed the conversations and idle chatter while she transformed ordinary soccer moms into PTA starlets. Occasionally, the conversation was therapeutic for stylist and customer alike.

Nearly one year removed from her divorce, she threw herself into her work, voraciously learning all the latest styling techniques and trends. Eventually, word spread and Caty was in high demand. Along the way, she had become pretty adept at forgetting her post-divorce loneliness.

Lynora was one of Caty’s original clients. A mature and striking brunette, she simply had presence that filled a room. Perhaps it was her success as an account executive at a Big Five consulting firm, or her brash confidence as a woman who knows what she wants, but those who knew Lynora were either impressed or downright intimidated. Rumor has it her ex-husband was the latter.

Over the years, the two formed a relationship beyond “client.” Caty appreciated Lynora’s tales of corporate politics, and was fascinated with the gossip out of the executive wing. Lynora, on the other hand, was struck with Caty’s ambition and passion for her craft, and had a soft spot for a recently-divorced woman trying to make it in the world. They were an unlikely pair, but it worked.

From time to time, the two would go out for drinks, mostly gourmet martinis. Inevitably, more intimate details of their lives would be shared after the third round. Lynora recounted a recent tryst with a former lover while on a business trip to Europe; Caty described a reunion with an old high school friend who turned out to have a really small dick (which was a deal breaker). They would crack each other up with their stories and sexual follies, and joke about giving up men forever and becoming lesbians. This was all just talk, of course. Nothing was better than the feeling of a good hard cock for these two ladies.

Speaking of good hard cock, it had been quite some time since Caty had been laid. It wasn’t as though she lost interest, she just lost interest in trying. To a point, she was a victim of her own success, putting in long hours at the salon and leaving little time for a social life. Although still a knockout, she simply had lost confidence in herself as a sexual being.

Caty’s situation had not gone unnoticed by Lynora. Indeed, she had gone through that dormant phase after her break up, but once she got back in the game, she was calling the shots. Her body was hers and she owned her libido, she thought. Just as she had done to earn her place in the hotly contested corporate world, she regained her sexual identity through her typical no-bullshit outlook on life. She had no problem exploring her sexuality with carefully chosen partners, and was direct about her intentions.

As was her custom, Lynora set up time with Caty in preparation for an important client meeting out west. As she was settling up after the appointment, Lynora mentioned she wanted to talk to Caty about something in private. The fact she had a slight smile put Caty at ease as they adjourned to an obscure corner near the front display.

“So here’s the deal,” Lynora began. “I won this cheesy ‘Chairman’s Choice’ award last month just for being super awesome. They’ll put me up in a swanky hotel and I get a spa treatment the next day. I even get to fuck the bellboy.”

“Oh wow, that so cool, Lyn!” Caty exclaimed, happy to her friend was recognized for her efforts.

“Yeah,” Lynora continued, “I guess it’s cool, but with all the travel, I just won’t have time to enjoy it. But, it is transferrable! And I want you to have it. In fact, I insist.”

Caty protested, noting how expensive the package must be, and that it was better given to someone else, family perhaps.

“Are you kidding me?” Lynora shot back. “I hate my fucking family.”

They both laughed, and Caty eventually accepted the offer.

“Hey, isn’t your one-year divorce anniversary coming up?” Lynora probed.

“Oh yeah, I’m counting down the days,” Caty sarcastically replied. “Thanks for the reminder.”

“Well you should use it on that day!” Lynora directed.” Just make sure you line up some man for the evening so you can stain the sheets.”

Caty’s divorce was finalized in early February, so a one year anniversary meant post-holiday blues tied together with pre-Valentine heartache. Yeah, Lynora was spot on.

###

Caty was in the process of packing for her weekend stay when she received a text from Lynora.

“Hey girl! I’m out west for a few days and wanted to check in with you on your big weekend. I have arranged for a limo to take you to and from the hotel for an extra splash of luxury!”

“Lyn!” Caty typed back, “You shouldn’t have!”

“Oh it’s nothing, shut up and enjoy it!” countered Lynora, leaving a wink emoticon to punctuate the playfulness. “The driver will be there at exactly nine o’clock, so be ready. And wear something hot, because I have an itinerary lined up for you.”

Caty was overwhelmed by the thought that went into this evening, and felt emotions rising in her chest.

“That so sweet, Lyn. I’m not sure how to thank you.” Caty replied.

“You can repay me by getting laid, and then telling me all about it in spicy detail.” Lynora retorted in her usual direct and deadpan style. “And I want pictures!”

Caty laughed out loud and signed off with her friend.

Looking through her closet, she found a black cocktail dress that fit her perfectly, her ample cleavage displayed with just the right amount of class, and inviting an extended gaze from men and women alike.

Damn, I forgot how good the twins look in this dress, she thought proudly.

She was also sufficiently satisfied her ass didn’t look too enormous. Completing the look with a pair of sharp and sexy black pumps, she was ready for her “itinerary.”

And it’s a good thing too, because minutes later Caty received a text from a number she didn’t know.

“Hello!” the cheerful text read. “This is Darryl and I’ll be your driver for tonight. I am out front and ready to depart when you are.”

A flush of excitement hit Caty as her evening was underway. She was ready to relax and be pampered for a change. Heading out of her condo, she was greeted by Darryl, dressed stylishly in a slim black suit, holding the door open. He was a tall black man who looked to be in his late twenties, very fit with a bright, flashy smile. He extended his hand to her, its size covering her hand as she offered hers.

“Ok Ms. Caty,” Darryl announced through the privacy panel, “we have a couple stops along the way. Just sit back and relax.”

She loved the reference to ‘Ms. Caty’ and his charming ebonic draw, which she found endearing.

The first stop turned out to be on the west side of town in the financial district. It was a swanky bar frequented by a lot of white collar criminals and inside traders, but that was during the week. On weekends, it was a bit more approachable as it catered to the theater going crowd.

“Ok,” began Darryl as he put the limo in park, “Ms. Lynora said to go straight to the bar and ask for Danny. He’ll pour you his signature martini.”

Well I’ll be damned, Caty thought incredulously, wondering how much planning went into this itinerary, not to mention the limo driver accomplice.

Being relatively early in the evening still, it was not crowded at all, and that was fine by Caty. As instructed, she made her way to the bar and asked for Danny, who turned out to be a stout Scotsman with a handlebar moustache.

“You must be Caty,” the jolly barkeep presumed. “I have a perfect martini for you.”

As Danny crafted the drink, Caty happened to notice a man at the corner of the bar. He looked to be of Mediterranean descent, with wavy jet black hair. The brief splashes of light from his smartphone would offer more teasing detail as he checked his messages. Caty figured he was making plans for a late-night interlude with an old flame. As her drink was being served, Caty was surprised to see him walking her way.

“Is this seat taken?” he asked.

Now that she had an unobstructed view, she was stunned. He was on the tall side, with a masculine jawline, hazel-green eyes and a sophisticated smile. His suit hung perfectly on his broad shoulders and trim waistline, framing him like a GQ cover.

Holy shit, she thought. This dude was top-shelf hot. Even the simple question regarding the vacancy of the seat was straight up sexy. This was a gorgeous man, and he was asking to sit next to her.

“No, of course not.” Caty managed to respond without stammering.

He introduced himself as Blake, and he was in town attending a conference on sewage and water purification technology.

What the fuck is that? Caty thought.

“Yeah, I’m a turd meister,” Blake offered, as if reading her mind. “That’s what we talk about at these conferences, what to do about all this shit.”

Caty laughed in half relief, and Blake laughed along with her. For the next hour, they traded questions about their careers, travels and even some life experiences. Caty was loving the attention of this handsome man, and was feeling a tingle of something she hadn’t in a long time. No, it wasn’t her vagina, it was confidence. She had forgotten not just how attractive she was, but that she made for pretty damned good company. The other tingle she was feeling was the buzz of Danny’s strong martini.

Just then, she received a text from Darryl. “Ok Ms. Caty, time for your next destination.”

She apologetically explained to Blake how her friend had set up this wonderful weekend, and that it was time for her to go. He understood. Turning to Caty, he took her hand and raised it to his lips, running a hand from her wrist to her forearm, giving her goose bumps.

Oh fuck it, she thought, I’m going for it.

Snaking her arm around from his broad shoulder to his neck, she pulled him down slightly to meet her lips. He did not resist, and in fact reciprocated as they gently explored each other. She had no idea how long they had been kissing, and she didn’t care. Eventually, they separated and she was on her way. There was a tingling now smack dab in the middle of her pussy.

###

“How was it, Ms. Caty?” Darryl energetically inquired.

Resisting the urge to say Um, I just basically tongue-fucked a total stranger, she instead replied, “Just wonderful.”

The next stop was a trendy, upscale bar on the other side of town, but closer to her hotel. As Darryl slowly coasted up to the curb, Caty couldn’t help but feel sexy. She could still taste Blake on her lips, and had been secretly rubbing herself in the limo.

Again opening the door for her, Darryl relayed the directive. “Ms. Lynora said to go see Edward, and he’ll pour you his signature martini.”

The bar had lots of glass, mirrors and silver; a good place for people watching with lots of reflections and angles to enjoy. Caty made a beeline for a cozy corner seat at the bar, and surveyed the surroundings as she waited to be served. She noticed a small group of twenty-somethings, a double date and a few couples. It was a cool place with a cool vibe.

“Caty, right?” questioned a warm but gravelly voice, snapping her back to reality.

It was Edward, an older gentleman with silver hair smoothed back, a pock-marked face and pudgy nose. While he certainly didn’t possess leading-man good looks, there was something about him that Caty found attractive. Not really in a sexual way, but in a paternal sense. Maybe he reminded her of someone from her childhood, but whatever it was, she felt right at home with him.

“Yes, and you must be Edward,” Caty confidently countered. “It’s nice to meet you.”

Edward began pulling out a number of bottles and bar accessories to prepare his signature drink. It was like watching a fine craftsman in action; swift, confident movements carefully honed over many years. Some of the other patrons were observing too, with a hint of curiosity and envy.

As it was getting later into the evening, there was quite the pedestrian traffic throughout the establishment; people making their way to the restrooms or greeting accidental acquaintances with insincere hugs and sanitary cheek kisses. Caty silently reveled in the people watching, devilishly spying on the small personal stories unfolding before her.

“Ok, here you go pretty girl,” said Edward, as he gently placed a gorgeous martini in front of Caty with a thick calloused hand. “This is called ‘The Edward’ and is named for a handsome bartender I knew many years ago,” slipping in a quick wink.

Caty instantly fell in love with the old man’s charm, and winked back as she held up the fragile cocktail class towards him in homage. The drink was simply exquisite, bursting in her mouth with flavor and decadent potency. It buzzed her instantly.

“Enjoy,” said the tenured bartender, as he turned his attention to others who were in need of high-quality cocktails.

She continued with her observations when an attractive, curvaceous blonde sauntered by, maintaining eye contact with Caty. Although it made her feel awkward, she was also intrigued by the moment and the sheer sexiness of the women. She was in her thirties and had a striking face, with high cheekbones and slightly slanted eyes. Like Caty, she was wearing a form fitting cocktail dress that tried to keep up with the curves of her body.

Well look at you, Mrs. Thang, Caty thought, catching a fleeting scent of the woman’s perfume as it whipped about on tiny jet streams.

Caty was surprised when the awkward feeling soon dissolved into muted arousal, humming below the surface and begging for a chance to emerge. Although she had never considered a bi-sexual experience, she couldn’t help but allow this woman’s raw sensuality to serpentine through her thoughts. A few minutes later, the women reappeared and approached Caty.

“I saw this same dress online and put it to my wish list,” the woman said, adding, “You look so gorgeous in it.” She gently brushed Caty’s arm and let her hand briefly touch the garment, as if taking tactile inventory of the fabric. Even though the woman’s hand was warm, the gesture caused a chill that ran through Caty and produced goose bumps.

While it was a compliment, she did not say it in a cheerful, girlie way. It was delivered with deadpan, but just enough warmth to be sexy. Caty stammered, very surprised by it all.

“Oh, thanks,” Caty replied with an unassuming laugh. “The style definitely seems to do wonders for my ass,” she added cheerfully.

“Well ‘the girls’ look to be well-represented too,” observed the woman, angling down with her eyes towards Caty’s full cleavage with a sly smile and cocked eyebrow.

Extending her hand, she introduced herself as Gwen. She told Caty she arrived a little early for a girl’s night out with two friends, and hoped she didn’t mind starting a conversation. For her part, Caty enjoyed the blunt opening repartee and was quite happy to continue talking with Gwen.

The girls quickly warmed up to one another and were soon discussing topics such as men, fashion, body image, celebrity gossip and more men. They even talked about Edward, with Gwen suggesting they abduct him into a backroom and have a surprise threesome with him. They shared a string of giggles and chortles as Gwen attempted to detail pushing a senior citizen into a meat locker for a reverse gang bang, his eyes wide in disbelief. Her deadpan style had Caty cracking up.

Just as their laughter began to subside, Caty’s phone lit up with another text from Darryl.

“Time to go, Ms. Caty!” exclaimed the text.

Caty was slightly disappointed as she was enjoying the time with Gwen, but she wanted to honor Lynora’s itinerary as the thought and effort invested was apparent. She explained the situation to Gwen and said she enjoyed the company and fun conversation.

“It was all my pleasure, honey” said Gwen warmly as she gracefully slipped off the barstool to hug Caty.

The two women shared more than a topical embrace, pressing into each other and letting their hands wander down to their waists. But it was not an overt display, and if anyone in the bar had seen, they wouldn’t have given it second thought. Again, the warmth of arousal spread throughout Caty’s pussy like flood waters over a river’s delta.

###

“Ms. Caty,” Darryl announced through the privacy panel, “this will be your final destination for the evening. It has been a pleasure to be your driver tonight.”

“Awe Darryl,” Caty responded sentimentally, “this has been a wonderful experience, and you were a big part of it.”

Darryl relayed one last instruction from Lynora, which was to have a nightcap at the hotel bar and turn in for the night so she would be well-rested for her day of pampering.

I am so masturbating tonight, Caty thought. How’s that for a nightcap, Lyn!

Her only regret is she didn’t bring her ‘toolbox,’ her reference to an impressive array of sex toys meant to get her through a long dry spell devoid of quality fucking. She had no idea the evening would turn out the way it did.

The limo cruised into the front entrance of the hotel, a gaudy homage to the hospitality industry. Darryl opened the door and a porter hurriedly whisked her bags to the lobby.

Standing on her tip toes and reaching up, Caty placed her hand on the side of Darryl’s face and gave him a quick peck on the cheek.

“Thank you again, Darryl. You’re a good man,” Caty said with some finality, but in hopes they might meet again someday.

Caty made her way through the opulent lobby and entered a ritzy corridor that smelled of lavender. Two men, dressed to the nines and looking impressive, passed by and interrupted their conversation to acknowledge Caty with you-look-fucking-hot nods in her direction. She was certain they kept leering as she continued down the hall, and she loved it.

Even though the hotel was new, the bar had an old nostalgia; deep, rich mahogany and weathered leather dominated the decor, with golden sconces dotting the walls. It was as if the entire hotel had been built around the bar, like a coveted archeological dig protected from heavy machinery and demands of impatient investors.

Caty was surprised there was not a soul in the bar, but didn’t mind. In fact, there wasn’t even a bartender in sight, but that didn’t stop Caty from plopping down on a stool and kicking off her heels. The sound of the black pumps hitting the wooden floor caused the bartender to shoot up from behind the bar, startling her.

“Oh wow, I’m sorry ma’am,” apologized the bartender, holding up his hands. “I was just restocking some things.”

He was a good-looking man: wavy dirty-blonde hair, chiseled face and smattering of facial hair. He had light hazel eyes (Caty’s favorite) perfectly set atop a slender nose that pointed to thin lips and a chin with a slight dimple. Although he looked to be in his early thirties, he had a weathered countenance suggesting he climbed Mt. Everest in his spare time.

He was wearing traditional bartender attire, a throwback to an era when the cocktail was king. A gray pinstripe vest covered a crisp white shirt and tie, which was loosened and slightly crooked. The sleeves were rolled up in workmanlike fashion, exposing muscular forearms and a tattoo. The pinstripes continued to his pants, which were straight and slender. Overall, this barkeep was put together.

Damn, thought Caty, what is up with tonight? The question alluded to attractive people just appeared before her, like a carefully orchestrated script with gorgeous sprites. If this were baseball, she’d be 4-for-4 and leading off for the Yankees.

Perhaps it was because she had a few high-quality cocktails, or the sudden infusion of confidence, but Caty was feeling good and assertive. Leaning over the bar to get a better view of his silver nameplate with Times New Roman engraving, she saw his name was ‘McGregor.’

“McGregor?” she asked. “Is that your first or last name?” A big smile setting across her face as she was in full-on flirt mode and didn’t give a fuck at this point.

“It’s my first,” the man said. “You see, my parents are Irish, a hundred percent. In fact, the story goes my great grandfather was in the IRA and hid from the authorities in a cave for a couple years.”

McGregor went on to explain his great grandfather was aided by a local blacksmith during this time, and promised to honor him one day by passing his surname through his bloodlines.

With a hint of pride, McGregor added, “And that’s how I got my name.”

“Well that’s some story, ‘McGregor,’” she said, with emphasis on his name out of respect for its lineage. “I’m Caty and I would like your signature drink for a nightcap.”

McGregor could sense Caty was feeling a quality buzz, and wanted to preserve it. He poured Caty a tall glass of water and said he would prepare a special cocktail only when she finished it. Caty groaned like a petulant teenager taking advice from her father, but eventually downed the contents. Letting out a playful Ahhhhh, she thrust the empty glass on the bar.

“Are you happy now?” she asked rebelliously.

McGregor laughed in retort and said, “You’ll thank me tomorrow, trust me.”

How ‘bout I thank you right now, Caty thought as she let a sly grin dance across her face. She hoped he heard this racy inner thought through some sort of bartender telepathy, just so she could deny it and admonish him for playing Jedi mind tricks on her.

McGregor began making Caty’s drink, a light aperitif called a Tres Jolie. Although it didn’t appear to be a complex mix, she was nonetheless impressed with his skill and precision in making it. She followed his masculine hands as he filled the mixing glass with ice and added the other ingredients. He stirred everything vigorously as if trying to coax the very best flavor, and then strained it into a classic cocktail glass. She was actually getting turned on watching him ply his craft.

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McGregor added an orange twist to complete the drink and presented it to her as if it were an extension of himself.

Caty took the drink and sipped gently, letting the contents fill her mouth with flavor. She instinctively closed her eyes as the taste went to her brain and made her mouth experience something like an orgasm.

She recovered, and setting the cocktail down in front of her gently, said, “Whoa, that is good.”

McGregor expressed dutiful satisfaction at her reaction -- not with arrogance, but like someone who expects his craft will satisfy.

“So how goes your night?” asked McGregor.

Caty thought for a moment. “Fun. Very fun.” She hoped he inquired further.

“Very fun? What was so fun about it?”

Caty let out a sigh of satisfaction and propped her chin on her hand while fondling the stem on her cocktail glass. “Well, it was just… sexy.”

“Sexy?” again repeating McGregor, following where Caty was leading the discussion.

“Yes,” she affirmed, her eyes widening for emphasis.

She went on to explain Lynora’s thoughtful itinerary, the limo ride and the day of pampering that was in store for her. She was feeling comfortable with McGregor now, and opened up about her failed marriage and subsequent lack of confidence as a woman.

“You know, Caty, I’m not supposed to make any specific observations regarding patrons, but you don’t seem to be lacking confidence. And besides,” McGregor trailed off bashfully, not finishing.

“What? C’mon, tell me!” Caty demanded.

“You’re gorgeous.” McGregor stated. “I mean, when you walked in, you were the picture of a sexy woman. That confident walk, your presence and that dress! I mean, fuck.” He had said ‘fuck’ with emphasis in a hushed tone, shaking his head and looking down at his task of drying beer mugs.

Caty was completely caught off guard at the compliment, but quickly recovered and let the arousal emerge again. Only this time, she intended to indulge in it.

What happened next was a shock to Caty. The words were hers, but they were not her own. It was as if her pussy detached from her body, jumped on the bar and took over the conversation.

“McGregor,” Caty began, deliberately pausing as she knew she only had one shot at an irresistible proposition, “I would rather not be alone tonight.”

Initially stunned, McGregor smiled and chuckled, incredulous but absolutely flattered. Caty instantly became horrified that her pussy had so bluntly propositioned a man she just met. Her genitalia had been serving hard time in sexual Siberia and was intent on making up for lost fucking.

Oh god, she thought, I’m an idiot! I didn’t even ask if he was involved. Maybe he’s not even straight! Maybe…

McGregor interrupted her self-scolding. “Caty,” he said softly, “hotel policy prohibits staff from getting involved with guests.”

Caty prepared for the let down and began nodding her head in understanding. Holding up an open hand, McGregor halted her before she could articulate her understanding.

“But, wait, just wait. That being said, I would love to spend time with you tonight.”

There was a pause, and then seizing an opportunity for levity, McGregor asked, “Wait, by saying you would rather not be alone tonight, you were implying you’d like to spend the night with me, right?” motioning to himself.

Caty threw her head back, laughing in a mixture of relief and anticipation. That lasted a moment and then the two discussed logistics. He lived a few minutes away in a loft he shared with two roommates and thought it was best to clean up a bit and return to her room. Caty gave him her room number and departed.

“See you soon,” she called back to McGregor with a wink.

###

Aside from making out and few other frustrating close calls, Caty had not been with a man since her divorce. She began to have doubts, and worried about her body image even though she had kept in shape and was blessed with good genes. Panic set in, and she thought about calling McGregor and canceling the rendezvous. Pulling out her phone, she realized they never exchanged numbers. There was no turning back now.

Just when the panic was beginning to swell, she recalled her evening. The compliments from Darryl and Edward, the sexual tension with Gwen and a passionate kiss with Blake. She also reminded herself that she rediscovered her confidence--even if it was only for the night. Finally, she reasoned that McGregor had accepted her proposition, so that was validation enough.

Caty had never been in a situation like this, and was unsure of protocol. She figured she would clean up, and change into something more comfortable such as a pair of faded jeans that fit her as well as the dress, and a basic top. She debated about going braless, and then she remembered a former lover had told her how great her tits look as they sway beneath her shirt when she walked.

Feeling incredibly nervous, Caty paced around the room, trying to think of any last-minute details.

Crap, she thought, I don’t have any condoms. Hopefully he’ll bring some or it’ll be hand job city tonight.

Just as Caty was checking her ass in the full-length mirror in the bathroom, she heard a knock at the door. A shot of excitement and adrenaline coursed through her insides. Taking a deep breath and then swallowing, she turned from the mirror made her way to the door. She declined to look through the security peephole because everyone looks like a goofy-ass caricature, and didn’t want to ruin the moment.

Her plan was to throw open the door and greet McGregor with a sensual smile and come-hither look. In her haste, she forgot to release the security latch, and the heavy slab made a loud thud that seemed to reverberate up and down the corridors of the floor.

You have to be fucking kidding me, Caty thought.

She finally negotiated the complexities of the door and opened it. McGregor appeared with a wide smile and twinkling eyes and they both shared in her embarrassment with laughter.

Like Caty, he was dressed in jeans and a t-shirt that read Get Lucky, Kiss an Irishman. Instinctively, she gave him a peck on the cheek.

“Your shirt told me to do that,” said Caty.

“Oh yeah? I swear, I didn’t even know I picked this shirt.”

“Sure you didn’t,” Caty responded sarcastically.

The couple ventured into the posh living space in the suite, and sat adjacent to one another on a leather couch and loveseat. McGregor lounged back while Caty tucked her feet under her, playing with her mouth and lips as they made small talk. The tension was unbearable, and each was secretly getting impatient with the other while they waited for a move.

Finally, Caty rose from the couch and approached McGregor, bracing herself on his shoulders as she settled onto his lap. She looked into his hazel eyes for affirmation. He pulled her towards him and they kissed, lightly at first, gently exploring the wet creases of their lips.

Soon, the kissing became greedier, as they exhaled through their noses since each mouth was preoccupied with pleasuring the other. Caty ran her hands through McGregor’s wavy hair, while he forced her hips into his crotch. Caty stopped for just a moment and pressing her forehead against his, filled herself with breath. She loved the feeling of his hardening cock against her vagina.

McGregor took the opportunity to kiss the front of her neck, a sweet spot for Caty. She began to moan--quietly at first out of shyness, but soon she was articulating a year’s worth of sexual frustration through primal groaning.

“Oh fuck,” Caty breathlessly whispered in between moans. “Fuck!”

She was basically fucking him on top, and he even slapped her ass through her form-fitting jeans. She was into it, and began pushing his face into her large breasts. Taking her cue, he lifted her shirt to expose her full tits, and gasped.

“My god,” McGregor observed in a hushed tone.

Pushing her tits together, he greedily began sucking each nipple until it was hard. Licking first, and then tugging and lightly biting with his front teeth. He continued to massage the outsides of her breasts and push them together, so close he could suck both nipples almost simultaneously.

“Yeah baby, suck my tits. Suck my fucking tits,” Caty encouraged as she pressed into him. For someone who had lost her sexual confidence, she was doing pretty well. She even lightly whipped her tits against McGregor’s face, and he loved it.

They resumed kissing, and Caty enjoyed the sensation of McGregor’s mouth even more than before. She sucked his tongue and pulled his bottom lip into her mouth, biting it gently. Her mouth needed more.

Throwing her shirt in the corner, Caty slid off McGregor and positioned herself at his feet. Snaking her hands up under his shirt, she maintained eye contact as her fingertips found his collar bone, and worked their way down. McGregor lurched as her manicured nails found hard crevices and valleys to dig into, but then relaxed when she alternated the exploring with her palms.

Caty’s pussy had gone from tingling to full-blown throbbing at this point. She was sure her excitement was visible through her jeans, but she didn’t give a fuck. In fact, she was deliberately teasing both of them. She waited a year and was getting mileage out of this hook up.

Her mouth began watering even before she unzipped his jeans. She moved her right hand down onto his crotch, but didn’t find the usual hardness in the same place: dead center and standing up at attention.

Instead, it started on top of his left leg and continued down his thigh. Trying to conceal her curiosity, Caty smoothed her hand from that spot and followed the hardness like it was The Yellow Brick Road. She began to gasp as she realized the world’s sexiest bartender might be packing some serious heat.

She rose upright and was about to unzip his jeans when she stopped to look at McGregor. He was lounging back and had a crooked smile, suggesting he was about to let her in on a big secret. She smiled back, and slowly yanked on the zipper. Coaxing his ass forward, the first thing she noticed is he wasn’t wearing underwear as a small patch of public hair greeted her instead of the usual waistband of tighty whities.

However, the next thing she noticed is that the second thing that typically follows the first thing didn’t happen. Usually, the man’s cock springs forward like a trebuchet catapulting a giant rock at a fortress. Although Caty had pulled his jeans down quite a bit, his cock was still pinned to his left leg by his jeans. She could see the thick veiny shaft straining against zipper.

Oh my god, Caty thought, as if she had just discovered an endangered species of snake. Or Sasquatch.

She slid his jeans down to his ankles, but never took her eyes off his huge cock. She wanted to see the moment it sprang to freedom. Because of its size, it didn’t lurch forward; rather, it lay to the side as blood continued to fill the soft tissue.

Caty ran her right hand down the length, and McGregor’s dick responded by twitching upward. She lifted it, pointed it towards her face and sunk down to begin inserting the length into her mouth. She savored his member by slowly running her tongue up each side, detecting the veins as they passed by. Looking directly at him, she swirled her tongue around the mushroom tip, causing him to jerk again and inhale sharply. She smiled at his torture.

She gave his long dick a couple of strokes to ensure it was moist enough for initial entry. Next, she licked her lips and inserted his giant, hard cock into her mouth and over her waiting tongue. Even though she was kneeling, she became weak in the knees as she let a burst of sensation commandeer her palate.

Caty was never adept at deep throating, and having had one bad experience, decided this was not the time to try to add to her sexual resume. Instead, she took what she could of him, and made the most of it. McGregor was writhing and undulating as Caty worked his cock, his hand on her head but not forcibly. Using the copious saliva produced from sucking him as lubricant, she stroked his dick in a twisting motion down to the base, which was a long journey indeed.

“Come here,” McGregor whispered, breaking the rhythm Caty had established so he could kiss her again.

It was as if a second act was to begin. Sweeping her up in his strong arms in a swift, singular motion, McGregor whisked Caty off to the large bed, and laid her out like he was getting ready to do some work. Hell, if he had sleeves, he would roll them up.

Instead of romantically working his way down her torso and stopping to slowly nibble every erogenous zone, McGregor went right for Caty’s damp pussy. He pulled her ass towards him as he knelt bedside, and pinning her thick legs back, began to lick away at her moist slit. Just as Caty had, he too experienced a complex mix of sensations, from her musky fragrance filling his head to the sweet taste of her clear cum on his lips.

“Ooohhhhh,” came the feeble groan from Caty, completely unguarded and resigned to what she was feeling. She was involuntarily swaying her head from side to side, the pleasure hitting some cerebral threshold. McGregor rolled her enlarged clit back and forth in his mouth, causing her to grunt and curse under her breath.

Venturing down, McGregor couldn’t resist running his tongue around her puckered asshole, which looked so inviting with her wide spread. The texture provided a sharp contrast to her fleshy pussy, and allowed Caty to experience new heights of pleasure. It was only a split second that McGregor had pressed his tongue into her that she experienced her first orgasm.

It started like a siren song beckoning to the farthest reaches of her body, areas thought to be long fallowed. The tingling pulled from all over--fingers, toes, nipples--and began traveling right to her cunt like an epicenter of a tectonic shift. McGregor continued to tongue fuck her in the ass as the orgasm wracked her body and mind, leaving her disoriented to the point of blacking out.

She lay there for what seemed like hours, but knew was only minutes. The orgasm had skewed her sense of time, slowing down her thoughts and blurring her reactions. Briefly, she was in a suspended state, completely susceptible to the perversions of a bartender she had met only hours ago.

Caty was gradually brought her back to reality by gentle tugging on her distended nipples. She lay there enjoying the attention, and could feel her libido recharging quicker than an iPhone (then again, everything charges faster than an iPhone). She reached to McGregor for more kissing, an expression of gratitude for how he made her feel.

“I need your big cock in me,” Caty demanded, and there was going to be no denying her.

She never thought for an instant about safe sex. That’s what a year without sex and an orgasm that will blow your tits off will do to a woman. She was crazed and she needed his gorgeous dick in her.

“Well then it’s a good thing I have a trunk full of these,” McGregor announced as he fumbled through his jean pockets, producing an ultra-thin condom.

Caty watched in rapt attention as he unrolled it like a Dead Sea scroll over his length, even giving it a few strokes to ensure it was in proper position. It barely covered half his manhood.

For some reason, McGregor had assumed they were going to fuck missionary, but Caty insisted on riding him. The momentary gap in communications caused them to bump heads, which made them both laugh while feigning injury.

“Ah, you want to work for a while? I’m cool with that,” said McGregor smoothly.

Caty pinned his sinewy shoulders to the mattress, maneuvering into position with one knee bended and supporting herself with the other foot. Because of his size, she had to jack her hips up just to accommodate his head, and slowly worked the tip into her pussy. She wasn’t concerned with being able to take his size as much as she wanted to tease herself.

Once she was confident he was firmly inside her, Caty took his entire length by forcing her hips to meet his. She let out a gasp and a soft whine as the sensation of his big dick spread throughout her loins. In no time at all, she worked up a good rhythm and was fucking him with authority. McGregor pleasured her big tits, trying to catch a nipple in his mouth as they swayed passed his face and bounced in multiple directions.

“C’mon Caty, fuck me,” McGregor challenged, slapping her ass for additional encouragement like a jockey using a riding crop. He let her control the tempo, which she varied from light grinding to violent humping, making them both groan in delight.

“You ready to let me work for a while?” asked McGregor as Caty’s pace slowed.

“Yeah baby,” Caty responded “but I want it from behind. Think you can do that?” she asked as she dismounted.

Not bothering to answer because it wasn’t a question, McGregor positioned Caty’s legs apart as she kneeled and held her ass high, presenting it to him. Just to torment her, McGregor ran the tip of his dick along her dripping slit. Inserting the first few inches, he pulled out to her protests. Finally, he braced her hips with his hands and began to push his length into her, slowly at first so she could receive it comfortably, but also so both could feel the slow grip of cunt on cock. She was completely filled now, her pussy stretched beyond anything she had ever imagined.

McGregor worked into an even stroke, not quite making Caty’s thick ass shake yet. She was totally submissive, content in letting him dictate the fucking. Gradually, he worked into a steady pounding, his hips clashing against her and making seismic waves of her ass. Caty gripped the bed sheets with two hands and fucked him back.

“C’mon you motherfucker, fucking fuck me!” Caty growled, not entirely sure where this voice was coming from and why it said ‘fuck’ three times in rapid succession.

McGregor loved the intensity, and placed his hand on the bed as to create more leverage. Caty let out visceral grunts with every thrust of his hips, his shaft filling her. Her cum had turned from clear to milky white, and it was all over the condom. Caty was sensing another orgasm.

“Lay me on my back,” Caty directed, and McGregor complied. Just as when he had given her oral, he pinned her legs back so he could get a good view of her pussy drawing him into her. And unlike earlier, McGregor didn’t need to ease into Caty, instead electing to slide his entire length in one, full stroke. Before long, he was pounding her at the same pace, making her breasts sway and heave. Caty wrapped her arms around his neck and locked her ankles around McGregor’s waist as she took his thrusting. Looking down at her vagina, she was so turned on to see such a display of genitalia in action.

That recently rediscovered chain reaction began again, this time starting at her clit because she had been fingering it. Spreading outward, it traveled up her torso and to the tips of her nipples. Caty looked to be in total agony as the orgasm paralyzed her, rendering her defenseless again to McGregor. Seeing her cum was a catalyst to him, and he began to explode inside her, his balls pumping numerous spurts of payload. Although he was still wearing the condom, the reservoir tip collected enough semen to provide warm pleasure for Caty.

Completely exhausted, they both collapsed. A well-earned deep sleep followed.

###

The next morning, Caty awoke to a text from Lynora.

“Good morning, sunshine! How was your night?”

Caty squinted at the message and smiled. McGregor was still sleeping next to her, and she wanted to wait before responding to Lyn. Just then, McGregor stirred awake and leaned over to give Caty a quick kiss.

“Wow,” she said quietly.

“Yeah, wow,” McGregor quickly agreed.

They weren’t sure what was going to happen next, but they agreed to keep in touch. They exchanged numbers and McGregor was on his way, hoping to evade the prying eyes of hotel management.

Caty turned her attention to the text message from Lynora and replied, “Can I call?”

Uh oh, Lynora thought I wonder what happened.

Minutes later, Lynora’s “Sweet Home Alabama” ringtone went off and she answered.

“Lynora,” Caty began “thank you so much for a wonderful evening. It was so awesome.”

“Great!” Lynora squealed in delight. “I’m so glad you had a great time.”

“And the itinerary with the limo--amazing! And I’m not sure what got into me, but I was getting compliments from all directions. I even had a hot woman hit on me!”

“Oh great, I knew they…” Lynora trailed off.

“What?”

“It’s nothing dear, really. Forget I said anything.”

“No, what? They who?” Caty insisted.

Lynora groaned in disappointment, knowing she had been busted and needed to come clean.

“Caty, please don’t be mad at me honey. I arranged for those people to approach you.”

Lynora continued, not giving Caty a chance to interject. “I see this beautiful, self-made and ambitious woman who doesn’t have a shred a confidence beyond that salon. I see a woman who is in danger of losing her sexual identity because some asshole ex-husband trapped her in a loveless marriage. I just wanted you to get your confidence back, to feel like a woman again. You deserve that.”

There was silence on the other end.

“Caty?” Lynora called.

“Well, I’m not sure how that’s supposed to make me feel,” Caty replied and then paused. “But you really put a lot of thought into it, and that I appreciate it.”

As Caty slowly wrapped her head around what Lynora had done for her, she became somewhat emotional. She quickly recovered and had to ask some questions.

“So,” Caty began, “you mean to tell me Blake was arranged? He doesn’t work with poop for a living?”

“No, he’s a male escort I call on from time to time.”

“What?!” Caty exclaimed. “A fucking escort! Oh my god, that’s hilarious!” Caty let the shock subside before moving on to the next question. “And what about Gwen, what’s her deal?”

“Blake’s girlfriend,” came Lynora’s matter-of-fact reply.

“And Darryl, Danny and Edward?”

“Those are some fine gentleman I have come across in my local travels.”

“Wow! Really? Well, that makes perfect sense.” Caty was almost embarrassed to ask about her lover, the hot bartender with the gorgeous cock.

“Ok, so what about McGregor?” Caty asked.

“McGregor?” Lynora asked back.

“Yeah, McGregor, you know. The bartender?”

“Who the fuck is McGregor?”

“Oh c’mon Lyn!”

“No, I swear, I have never heard of him. Is this someone you met last night?”

Just then, Caty realized the extent of what Lynora had done for her. She had helped her rediscover her confidence and reclaim her womanhood. And got her nicely laid in the process.

“Girl, have I got a story for you.”

Published 
Written by scottsmith1717
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