Alana collapsed on her bed after packaging up the cold dinner she made her and her husband. He called, just as he should have been leaving work to let her know it was going to be another late night, which Alana knew meant he wouldn’t be coming home until sometime after midnight. For the past twenty years, Stewart had to work late, maybe a dozen times. In the last two months, he had already surpassed that number. It was cliché and obvious. He barely put any effort into hiding his affair and Alana put in a similar amount of effort into pretending she didn’t know. On some nights, Alana would get dressed up and head to her favorite bar. There she would flirt, hoping to have a debaucherous one-night affair. But she was no longer twenty-one and picking up men at the bar was a skill that had faded with disuse.

On the nights she did not venture out, Alana found herself alone in her bed with a small vibrator and a vivid imagination. Her fantasy revolved around a particular bartender. He was tall and classically handsome. He had thick brown hair with lots of volume that gave him a youthful look, especially paired with his clean-shaven face. He had a square jaw with a quick, easy smile. He wore black or white shirts with jeans and filled them out nicely.

Alana preferred his conversation to most others. He was a man of few words, but with a quick wit. They didn’t spend much time on small talk or personal questions. Instead, they guessed about the lives of other patrons in the bar. 

That was as much as Alana knew. But, in her head, he was a grad-student at the local university, bar tending to make ends meet. Between work and his studies, he had no time for a girlfriend, even though he had numerous women throwing themselves at him. That, of course, all changed when Alana walked into the bar. It was a slow night; they would chat and flirt effortlessly and just as the night was about to end, he would invite her to his apartment above the bar.

Alana undid her robe and slipped her hand underneath her night shorts, past her neatly trimmed bush, and found the bud of her clit. She rubbed herself slowly, imagining herself kissing the young bartender in the entryway of his apartment, too eager to make it to the couch. The buildup was slow, passionate. They took turns peeling off each other’s clothing, kissing, and exploring the other’s body as they did. Her hands grazed along his chest and defined abs while his fingers tenderly toured her curves.

Imagining that it was his hand, she reached under her nightshirt, grabbed her large breasts, and teased her nipples. The foreplay lasted an hour or more. During which time she took his large manhood into her mouth, sucking his tip and licking his shaft from base to head. He then returned the favor. She lay down on the sofa as he kissed her thighs and found her clit with his expert tongue, bringing her to a blissful orgasm.

Alana grew hotter and wetter as her fantasy continued. Her fingers slipped easily inside her pussy. She allowed a brief moan as she imagined her partner leaning forward and giving her a kiss before positioning himself at her opening.

Alana grabbed her vibrator, and it hummed to life. With three fingers, she penetrated and stroked her pussy as the vibrator worked her clit. Her body immediately tensed with pleasure, and she sped up her fantasy to meet her imminent orgasm. She imagined him on top of her, thrusting his large cock deep inside her in fast, rhythmic movement. His hands gripped her sides, and she threw her head back in both her fantasy and reality. An orgasm washed over her body as she pinched her thighs together, hoping to keep that moment forever.

As always, the moment passed and Alana was left alone in her room, facing the harsh reality. In her fantasy, she was twenty-one again, not nearing fifty. While she still had many of the assets she did when she was younger, a firm, heart-shaped ass and toned legs. She also had a softer stomach, and her large breasts hung a little lower. She could scarcely imagine a man that much younger being interested.

The following weekend, Stewart had a sudden business trip and wouldn’t return until Sunday. Alana, not wanting to waste another night on fantasy, decided to try her luck at the bar. She slipped on a slim purple and white dress with thin straps and plunging neckline. She decorated herself with a layered silver chain necklace and thick bangle bracelet. She wore her favorite white gladiator pumps which wrapped delicately up her legs. She put on bright red lipstick and mascara to complete her smokey eyes. She misted herself with Valentin’s Donna Born in Roma Intense Eau De Parfum. Lastly, she slipped her gold wedding band from her finger and left it on the nightstand.

The bar was far busier than in her fantasy, with barely a place to sit and several bartenders working. She found a stool near one of the bar and claimed her spot. She searched the crowd for a potential match when, as luck would have it, her favorite bartender came to take her order.

He leaned casually on the bar and cast a quick glance at the crowd. “Lots of people in here tonight,” he said. “Unfortunately, I doubt most of their lives are of too much interest.”

“That’s hard to say,” Alana replied. “We haven’t even begun inventing them yet.”

“I don’t normally see you here on the weekend.” He turned away from the crowd and focused on her.

“Trying something new,” she said. “I’ll have a Vodka Cranberry, please.”

“Trying something new,” he repeated. “Yet you order the same drink. No, that’s your weekday drink. I’ll make you something special for tonight.” The bartender grabbed several fancy bottles from the shelves and mixed them expertly in a tumbler before presenting it to me.

“An Aviation Cocktail. It’s a bit darker than you’re used to. A little bit but I think you’ll find it more satisfying.”

“I didn’t know you could get such sophisticated drinks here.”

“That one’s off menu,” he said before turning towards a couple flagging him down.   

Alana sipped on her drink and made flirtatious conversation with several men. There was a gentleman around her own age in a suit and button-up shirt with the top three buttons undone. He was sweet and complimentary but a little nervous. She thought he was probably there for the same reason as herself, but he reminded her too much of her husband.

“Let me guess,” the bartender asked as swapped her glass for a full one. “Door to door bible salesman?”

“Accountant,” she replied.

“I think a bible salesman would be more interesting.” He then returned to his duties.

A younger man approached her as well, wearing a colorful t-shirt and shorts. He was confident and openly commented on her dress and how it flowed on her body. He ordered her a drink before whispering in her ear a few sordid details about the night they could have together. While his youthfulness made it a tempting offer, all Alana could picture was herself in the dorm room with a passed-out frat boy.

“I heard the pizza joint’s registers are broken,” the bartender interjected once the frat boy had overstayed his welcome. “They’re just giving away slices.”

“No way!” the frat boy slurred before rushing out the door.

“Thanks,” she said with a sultry smile.

“I could never ignore a damsel in distress.”

After no more noteworthy encounters, they announced last call. Alana hoped to spend the last few minutes of her night in fun conversation, but the bartender was nowhere to be seen. She ordered her last drink and stayed until they closed and locked the doors. Alana was then outside in the cold, fishing her phone out of her purse.

“I’ll call you a taxi, if you’d like.” The young bartender from her fantasy emerged from the alley next to the bar. He looked much the same as always, handsome, and casual, only now he wore a black denim jacket with a cigarette held loosely between his lips.

“What if I’m not looking for a taxi?” Alana asked, taking a few steps closer to him.

“I’d rather you didn’t walk home alone,” he said, lighting up the cigarette with a spark from his lighter. “It’s cold and dark and lady like yourself shouldn’t be walking alone.”

“What if I didn’t want to go home?” Alana replied, growing bolder. “What if I didn’t want the night to end so early?”

He took a drag from his cigarette, stepping towards her, careful not to blow any smoke in her direction. “I’m not what you came here looking for tonight,” he finally said.

“You seem to know what I want better than I do,” she replied, now less than a step away from him. “I mean, you did scare away two potential dates.”

“They weren’t what you were looking for either,” he said confidently.

“Then what do I want?” she asked.

He shook his head. “I don’t know what you truly want. What you desire. But I’ve bar tended long enough to know what a woman, dressed the way you are, coming to a bar alone at night is looking for.”

Alana’s eyes darted to the ground. For a quick moment she felt ashamed, transparent. As if everybody in the world knew she was there looking for a pity fuck because her husband was spending the weekend with his mistress. She thought about asking him to call her a taxi or just turning around and walking home. Perhaps it was the alcohol or the fact that this was the closest she had ever gotten to her fantasy. Because, instead, she said, “What if I told you I’m searching for I what I desire.”

She then slowly pulled the cigarette from his fingers. She took a slow, seductive drag like she would have in her twenties and blew the smoke into the air between them.

The bartender removed his jacket and slung it over her shoulders before taking out another cigarette and lighting it for himself. Without another word between them, He led Alana up a few blocks until they arrived at his third story apartment. It was small but open, almost a studio. They walked directly into the kitchen, with the living room directly behind the counter. The bedroom was off to the right, the door already open. It looked surprising like the apartment from her fantasies.

He took his jacket from Alana and hung it next to the door. “It’s alright if you want to leave.” He tucked a piece of hair behind her ear, grazing the side of her face. “But you’ll regret it.” He took her chin in his hand and kissed her in the kitchen, just like in her fantasy. “Follow me.”

He walked towards the bedroom. Alana stayed silent, not wanting her shaky voice to betray her confidence as she followed. A king-sized bed was situated in the center of the back wall with luscious red sheets and large pillows. On the left side wall was a door to the bathroom and on the right was a mahogany dresser next to a matching chest, from which the bartender retrieved a purple bit of cloth that almost matched Alana’s dress.

She stood at the end of the bed when he stepped in front of her. His penetrating brown eyes looked deeply into hers. “Do you trust me?”

Alana nodded, not breaking the intimate eye contact between them. The bartender brought the folded bit of cloth up and placed it around Alana’s eyes, securing it tightly behind her head. Her breath quickened, uneasy with the loss of one of her senses. In the now black void, she felt his gentle touch on the top of her neck and followed it down and across her shoulder until it reached the thin strap of her dress. He slowly pushed it from her shoulder. Her dress slunk at an angle, revealing her white bra beneath. Alana suddenly felt exposed and reached out with her other sense, only to hear the bartender’s steady breath and the creaking of floorboards as he moved. This had never been part of her fantasy.

“I suddenly realize,” she stammered. “I don’t even know your name.”

He placed his fingers on the opposite side of her neck and spoke as he moved them downward. “It’s not important now. You will only refer to me as Master.” He pushed the second strap from her shoulder and the dress slid off her body and crumpled to the floor. A quick gasp escaped her throat, and she instinctually reached to remove the blindfold, but quick and forceful hands stopped her before she could.

“The blindfold stays on until I say otherwise.” His voice was steady and commanding. “If you would like the night to end at any time, you only have to say so.” He paused for a moment before continuing. “If you want to stay, you should know that I will push your boundaries and you will experience things I am quite sure you have never experienced before. However, you must follow the rules.”

“I’m not sure.” Her voice quivered. She knew about BDSM in only the most general context. She knew enough about what was happening, but too little to know what to expect. “I’ve never been a… uh.”

“A submissive,” he finished her sentence. “I didn’t think you had. Certainly not what you were looking for tonight, but perhaps it is what you desire.

Alana hesitated for a moment. Her head swam with intoxication, anxiety, a little fear, and as much as she may not have wanted to admit it, arousal. She could not deny the sensation. Her skin flushed warm with excitement at his touch and the smooth control in his voice.

“Okay,” she agreed.

He ran his hand across Alana’s stomach. “Here are the rules. You do not speak. You do not gasp. You do not moan unless I give you permission. If you do, you will be punished.”

The bartender paused with a finger just under the strap of her bra, waiting for a response. When none came, he traced the edge of her bra around her body until he came to the clasp at the back. “You will be obedient and do as you are told. You will comply the first time you are told, and you will do so quickly. You will say ‘yes Master’ if you are able. If you do not, you will be punished.”

He undid the clasp of her bra and pulled the straps over her shoulders and down her arms. Her large breasts fell freely, revealing her long brown nipples and wide areolas. Alana twisted and yielded to the urge to cover her exposed tits.

“Arms at your side,” the bartender commanded. She hesitated only for a moment before obeying his command.

“And what do you say when you acknowledge my command?” he asked.

“Yes, Master,” Alana said. Although she could not see it, she sensed the smile spread across her Master’s face.

He reached out with both hands and cupped her breasts, teasing her nipples with his thumbs until they poked forward eagerly. “You’re absolutely stunning.”

He stepped away, only to return a moment later. “You’re going to feel a little pinch.” Then Alana felt cold, rubber tips clamped onto her nipples. With a sudden shock of pain followed by a wave of pleasure, Alana let out a sharp gasp.

“Did I give you permission to gasp?” the bartender asked.

“No, Master,” Alana breathed.

The bartender played with the small weight that rested at the bottom of the chain connecting the nipples clamps, pulling slightly at her swollen nipples, causing Alana to twist under the sensation and focus on keeping her breath even and controlled.

“Turn around and face the bed,” the bartender instructed as he once again went to retrieve an item from the chest. “Bend forward and lie face down with your hands at your side.”

“Yes, Master,” Alana replied as she clumsily found the foot of the bed and pressed her chest flat against the soft satin sheets. The bartender took his place behind her and looped his fingers into her the waistband of her panties and lowered them down her legs, leaving them wrapped around her ankles.

Alana waited; her body hummed with anticipation. She started to bring her legs together but froze, not wanting to upset her Master. She then waited for whatever form of punishment she was about to receive. To her surprise, without any touch from her Master at all, she could feel her pussy getting wetter and her arousal rising. She had no clue what to expect, and that made her breath hot.

After moments of waiting, Alana felt a sudden sharp sting across her back, which was followed by the light tickling of feathers and rush of pleasure. Her body writhed in response to both feelings. Her tits, still clamped, rubbed against the satin sheets, intensifying the pleasure. She bit down hard into the sheets to keep from calling out. She took a few measured breaths to calm her senses just as another strike landed against her bare back.

Alana twisted and turned even more. Not only had the pain intensified, but so had the pleasure. Tears welled up in her eyes and once again she bit into the sheets. When the third strike was about to land, Alana moved her hands to cover her back, not entirely sure whether it was the pain or pleasure that had become too much for her. Even though the strike landed on her arms, the waves of competing sensations plunged through her body, anyway. Caught off guard, she let out a load moan, followed by a breathy, “fuck!” It wasn’t until afterwards that Alana realized she broke a rule.

The bartender dropped the flogger next to Alana and held her hands behind her back by the wrists. “Care to explain yourself?” he asked.

“It’s too much,” Alana whimpered. “It’s just too much.”

“What is?” he asked.

Alana shook her head, not knowing the truthful answer to that question. “All of it,” she finally said.

He let go of her wrists and replied, “If you want the night to end, you have to say the words.” His voice was still firm, yet softer than before. It was not an order and Alana understood that she could end it right now.

The voice in her head told her to end it. It was nothing like her fantasy. Nothing like anything she had ever done. She could feel the many thin strips of pain on her back where the flogger had landed. Her nipples were raw and, like an exposed nerve, reacted to the slightest touch or movement.

“No, Master,” she finally said. “I broke a rule and must be punished.” Alana almost couldn’t believe the words that she had just said.

“Correct,” the bartender said. “But first, some preparation.” He wrapped a rope around her wrists, not soft like the fabric he used for her blindfold. It was rough and abrasive and chafed her skin.

“That’s because you moved your hands; they can’t be trusted.” He then lifted her head and placed a rubber ball between her teeth, fastening the straps tight behind her head.

“That’s because you spoke out of turn.” Finally, he wrapped her ankles in the same abrasive rope and tied them to either bedpost. Her legs were now spread wide open, her ass and pussy completely exposed.

Alana whimpered silently into her gag. In a few quick moments she had been subdued and restricted, barely able to move at all. With no access to her hands, and no ability to speak, there was little she could do to resist her Master. And that filled her with terrible excitement.

“This is called a crop,” the bartender said from behind Alana. “It’s going to sting, more than the flogger I just used. But I am generous, and I’ve given you the tools to behave yourself.”

“Thank you, Master,” Alana said unintelligibly into her gag.

Alana felt the leather crop slide up her left leg, pausing at the very top, grazing the lips of her pussy, before sliding down her right leg. She twisted against the restraints in anticipation of the pain with little effect.

The bartender then brought the crop back up the right leg and giving Alana a quick smack on the fleshy inside of her thigh. She twisted again, the pair sharper and more specific than the flogger, yet more bearable. The closeness of the pain next to her aching pussy made the pleasure more vibrant.

The bartender continued to run the crop across her body; inside her legs, outside her legs, across her buttocks, and every few moments, giving her a smack. Each time she writhed, whimpered, and moaned. The lower part of her body became covered in bright red marks and little mounds of raised flesh.

Alana’s mind was lost. The pain and pleasure no longer peaked and crashed like waves on a beach, but flowed through her constantly like a rushing river. The ropes that bound her rubbed her wrists and ankles raw. The gag in her mouth caused her jaw to be sore as she screamed into it. The nipple clamps caused a constant throbbing through her body. And the soft blindfold only served to heighten all these sensations.

After every few strikes the bartend would say, “Your punishment is nearly over, should I continue?”

Each time Alana nodded her face into the tear-stained blankets.

After what felt like several minutes, the bartender dropped the crop and rubbed his hands softly across Alana’s ass and thigh, his fingers a cool oasis against her hot skin. He then bent down and pressed his tongue against her clit.

The sensation flooded Alana with pleasure and emotion, like it was the first time she had ever been touched. Her back arched and she pressed as far backwards as her restraints would allow as her Master’s tongue ran the entire length of her slit. Her legs shook uncontrollably, twisting against her bindings. She was close to climax, an orgasm swelled inside her.

The bartender stood. “I haven’t given you permission yet,” he reminded her with a charming, sadistic hint in his voice.

Alana teetered on the edge, trying to hold off as long as possible to please her Master. She buried her face into the sheets once again, not finding any relief in its soft, cool folds. She tried to close her legs and stifle the growing orgasm, but her legs were still bound, and the struggle only made the feeling grow. Her Master pressed the tip of his member against her wet opening, making her whimper with restraint.

“You may cum,” he commanded as he pushed his entire length inside her inviting cunt. Her body erupted like fireworks before he was even fully inside her. Warm, delicious pleasure radiated from her center and spread to the tips of her fingers and toes. She curled and rocked her body, bucking against her Master and his massive cock. Her pussy clamped and released around him as she came, squirting all over her Master and his cock.

At the same time, she heard him grunt as he held himself deep inside her, pulsating and climaxing in harmony with her. She felt the warm fluid fill her and for a moment it was no longer pain and pleasure, but just a mind-shattering orgasm.

They then both collapsed onto the bed, breathless and spent. After a moment, the bartender pulled himself up and began untying Alana. He started with the gag, letting her suck in some much-needed air as he worked on the other bindings. He undid her wrists, then her ankles, before removing the nipple clamps, and finally the blindfold.

He helped her climb fully onto the bed and laid her head on a soft pillow. He pulled a gel from his bedside table and rubbed it along her thigh and ass cheeks where the crop had left its mark. Alana melted into the bed as the cooling sensation spread across her burning red skin. The relief was so great that she thought she might climax again.

Afterwards, he covered her with the cool satin sheets, holding her between his arms. With one hand, he brushed back her hair behind her ear. Once again, looking right into her eyes, he said, not in a commanding tone but soft and warm, “you were absolutely amazing,” before tenderly kissing her on the lips.