Esmie's Rough Night Out

Esmie stood before the full-length mirror in her bedroom, surveying her reflection with a critical eye. Her smooth, olive skin was flawless, and her toned muscles rippled beneath the surface. She had always been an athletic woman, and she took pride in her physical prowess.

With a deep breath, Esmie reached for her makeup bag, carefully selecting her tools as she studied her face. She wanted to look perfect for what she was about to do. Her husband had left town on a business trip, and Esmie was feeling restless. She needed a release, something to take her mind off of the monotony of her daily life.

Esmie's hands moved deftly over her face, applying foundation, blush, and eye makeup with practiced ease. As she worked, her thoughts drifted to a memory that had been nagging at her for weeks.

A few weeks ago, she had been walking down the street on her way home from work when a man had catcalled her from across the road. She had ignored him, as she always did, but then he had shouted something that had stopped her in her tracks. "Hey, pretty lady! How much for a night with you?"

At first, Esmie had been offended. She had always prided herself on her independence and her refusal to be objectified by men. But as she walked away, the thought had taken root in her mind. What if she did accept the man's offer? What would it be like to be paid for sex?

The thought had haunted her ever since, a guilty pleasure that she couldn't shake.

With a final touch of lip gloss, Esmie stepped back from the mirror to admire her handiwork. She was dressed in an outfit that she knew would turn heads - a tight, black crop top that barely covered her ample breasts, paired with a miniskirt so short that it barely covered her backside. She had chosen thigh-high boots to complete the look, knowing that they would make her legs look even longer and sexier.

As she stepped into the garage, Esmie felt a rush of excitement. She knew that she looked like a walking advertisement for sex, and she relished the attention that she was sure to receive.

Esmie got into her car, feeling a rush of adrenaline as she turned on the engine. She drove downtown, heading to an area where she knew that streetwalkers were common. She didn't have any specific plan in mind - she just wanted to sit and watch the women from her car.

As she pulled up to the curb, Esmie felt a thrill of anticipation. The women on the street were dressed even more provocatively than she was, and they moved with a confidence that she couldn't help but admire. She watched as they worked their corners, flirting with passersby and beckoning potential clients over with a sultry glance.

Esmie had never seen anything like it before. She felt a mixture of arousal and unease as she watched the women, wondering what it must be like to make a living by selling your body. She knew that she could never do it herself - the thought of being intimate with a stranger was too terrifying - but at the same time, she couldn't help but be fascinated by their lives.

As the night wore on, Esmie found herself growing bolder. She worked up the nerve to get out of the car and walk down the block, feeling the eyes of every passerby on her as she moved. Her outfit felt like it was barely there, exposing her skin and leaving her feeling both exhilarated and vulnerable.

Esmie leaned against a light pole, watching as cars drove by. Some slowed down to get a better look at her, while others drove by without a second glance. She could feel her heart racing as she stood there, unsure of what would happen next.

Suddenly, a car drove by slowly, circling the block before pulling up next to her. The window rolled down, and a man leaned out, eyeing her up and down.

"How much for a good time?" he asked, his voice oozing with lust.

Esmie's heart leapt into her throat as she realized what was happening. She had never been propositioned before, and the reality of the situation hit her like a ton of bricks.

"I'm sorry," she stammered, backing away from the car. "I'm not a prostitute."

The man scowled and rolled up the window, driving off in a huff. Esmie watched him go, feeling a mixture of relief and disappointment. She had come so close to crossing a line, but in the end, she couldn't go through with it. She knew that she wasn't cut out for this life, and that she needed to go home and forget about what she had seen.

As Esmie slowly walked back to her car, her mind was in a whirl. The encounter with the man in the car had left her feeling shaken, but there was still a part of her that was curious about what it would be like to be with someone for money. Before she could reach her car, another car pulled up beside her. The window rolled down, and the driver, a middle-aged man with a receding hairline, looked her up and down.

"How much for a blowjob?" he asked, his eyes lingering on her chest. Esmie's eyes were drawn to the bulge in his pants, and she felt her body responding despite her better judgment.

She hesitated for a moment before naming a price that she knew was too high. "Two hundred dollars," she said, her voice barely above a whisper.

The man's eyes widened in surprise, but he quickly recovered and nodded. "Get in," he said, unlocking the passenger door. Esmie hesitated for a moment, her mind racing with conflicting thoughts. She knew that she should walk away, but the lure of the money was too strong to resist. She climbed into the car, feeling the man's eyes on her as she closed the door. As he drove off into the night, Esmie couldn't help but wonder what she had gotten herself into.

Esmie's heart was pounding in her chest as the car pulled into a dark alley. She glanced nervously at the man beside her, taking in his features for the first time. He was older than she had originally thought, with deep lines etched into his face and a gut that hung over his belt.

As they parked, the man handed Esmie the wad of cash, and she couldn't help but feel a twinge of guilt as she stuffed it into her purse. He leaned his seat back, and Esmie took a deep breath, mentally steeling herself for what was to come.

"Go ahead," the man said gruffly, gesturing down at his crotch. "I'm paying you for a service, so get to it."

Esmie's eyes were drawn to the bulge in his pants once again. It was bigger than she had expected, and she could feel a thrill of excitement mixed with fear coursing through her body.

With trembling hands, she reached out and unbuckled his belt, pulling down his pants to reveal his erect member. She had seen pictures before, of course, but seeing it in person was a completely different experience. It was thick and veiny, pulsing with desire.

For a moment, Esmie hesitated, unsure of what to do next. But the man's impatience was clear, and he let out a grunt of frustration.

"Just do it already," he growled. "I don't have all night."

Esmie couldn't help but stare in awe at the sight of the man's hard shaft. She had never been with a man other than her husband, and seeing the thick, veiny penis in front of her was both exciting and intimidating. She took a deep breath and wrapped her small hand around the base of his member, marveling at the way it pulsed with desire. As she began to stroke him tentatively, the man let out a low groan of pleasure. Esmie could feel his cock growing harder in her hand, and she felt a rush of excitement at the thought of being able to give him pleasure. She leaned forward and took the tip of his cock into her mouth, flicking her tongue across the head as she continued to stroke him with her hand. The man groaned again, his fingers tangling in Esmie's hair as he pulled her closer. She could feel the weight of his member on her tongue, and she bobbed her head up and down, taking more of him into her mouth with each movement. As she relaxed, she found herself enjoying the taste and texture of him in her mouth, and her movements grew more confident and purposeful. As she worked her mouth up and down the length of his shaft, the man's breathing grew heavy and labored. She could feel his body tense as he approached the brink of orgasm, and Esmie redoubled her efforts, determined to bring him to the edge and over it.

Esmie continued to suck on the man's cock, her head moving back and forth as she took him deeper into her mouth. She used her tongue to swirl around the head, teasing him, and felt him start to twitch and throb in her mouth. She knew he was close. With one final, desperate thrust, he pushed his hips forward and let out a loud groan. Esmie felt the first burst of his hot, sticky cum hit the back of her throat. She swallowed reflexively, eager to taste more. The salty, bitter liquid filled her mouth, coating her tongue and teeth. She continued to suck and lick, milking every drop out of him. The man's body went limp, and he leaned back in his seat, panting heavily. Esmie pulled back, wiping her mouth with the back of her hand. She could feel his cum still on her lips and tongue, and she swallowed again, savoring the taste. It was salty and slightly bitter, but not entirely unpleasant.

Esmie leaned forward and kissed the tip of the man's softening member as she pulled up his pants, zipping him back up. He grunted in response and handed her the agreed-upon payment. Esmie took the money and got out of the car, closing the door behind her. The man drove off, leaving her standing alone on the dimly lit street. Esmie wiped her mouth again and took a deep breath, feeling a mixture of excitement and disgust. She knew that what she had just done was wrong, but at the same time, it had been exhilarating. Esmie decided to keep walking up and down the street, the thrill of the experience still coursing through her veins.

Esmie watched as the young man drove up to her in his beat-up sedan. He looked like he was barely out of college, with his shaggy brown hair and nervous eyes. As he rolled down the window, Esmie leaned in, catching a whiff of his cologne.

"How much for sex?" he asked, his voice shaking slightly.

"Two hundred," Esmie replied warmly after thinking for a moment.

"Okay, okay, that's fine," he said. "Now, or after?"

Esmie let out a small smile as she climbed into the car, miniskirt riding up on her legs. "You can pay me after." As they drove to a nearby alley, Esmie decided to take the lead, climbing over the center console, pressing her body against his as she straddled him.

The young man's hands shook as he fumbled with his belt, the anticipation of finally having sex with a woman making him nervous. Esmie could sense his hesitation, so she took the lead, pressing her body against his as she straddled him. His hands found their way to her hips, gripping tightly as she ground against him, feeling his erection grow harder beneath her.

Esmie leaned in to kiss him, her lips parting as she deepened the kiss, her tongue exploring his mouth. The young man responded eagerly, his hands roaming up her back, pulling her closer as they kissed. As the heat between them grew more intense, Esmie broke the kiss and reached for a condom, ripping open the packet and rolling it onto his shaft.

Esmie's fingers trembled as she tore open the condom packet, her heart racing with excitement and anticipation. She rolled the latex sheath onto his thick shaft, marveling at the sight of him fully erect and ready for her. It was a beautiful sight, the head of his cock glistening with pre-cum, veins pulsing with every beat of his heart.

As she positioned herself above him, Esmie could feel her own arousal building with each passing moment. She placed her hands on his chest, steadying herself as she slowly lowered herself onto him. The sensation was intense, his shaft filling her up in a way that made her gasp.

"Oh, fuck," she moaned, feeling his hardness stretching her in the most delicious way. She began to move, sliding up and down on his length, her hips rolling as she found the perfect angle. The young man's hands gripped her hips, his fingers digging painfully into her flesh as he urged her on.

She quickened the pace, the pleasure building inside her with every thrust. The young man's body stiffened as he approached orgasm, his breathing ragged and labored. Esmie could feel him pulsing inside her, and she groaned in ecstasy as she contracted her walls around him, coaxing his cum out of him.

With a final shudder, the young man came, spilling his seed into the condom. Esmie collapsed against him, breathing heavily as the aftershocks of pleasure rippled through her body. She could feel his heart racing beneath her, and for a moment, she simply lay there, basking in the afterglow.

"That was amazing," the young man said, his voice breathless and filled with wonder.

Esmie smiled, feeling a sense of pride and satisfaction. "I know," she said softly, pressing a tender kiss to his lips. "I'm glad you enjoyed it."

The young man fumbled for his wallet, trying to find the right bills to pay Esmie. She could see the anxiety etched on his face, and decided to take pity on him. "It's fine, don't worry about it," she said, smiling at him.

"Really?" he asked, his eyes wide with surprise.

"Really," Esmie confirmed, nodding her head. "Consider it a freebie."

The young man breathed a sigh of relief, and Esmie climbed off him, adjusting her skirt as she got out of the car. "Thanks," he called after her, and she turned back to give him a small wave.

Walking down the street, Esmie felt the thrill of the encounter still coursing through her veins. She had always been drawn to danger, to the illicit thrill of doing something forbidden, and this was no different.

As Esmie walked down the street, she could feel the night growing darker and more dangerous. She quickened her pace, the heels of her boots clicking on the pavement. Suddenly, a car pulled up next to her, the headlights blinding her for a moment. As her eyes adjusted, she saw a large, overweight man in the driver's seat.

"Hey baby, how much for a piece of that?" he leered, looking her up and down.

Esmie shook her head, "No, I'm not interested."

The man persisted, "Come on now, I got cash to spare. Name your price."

Esmie hesitated, but the man threw out a couple of numbers, each one higher than the last, until he finally said a large amount that made her reconsider. Against her better judgment, she agreed and climbed into the man's vehicle.

Esmie felt uneasy as the man's hands roamed over her body, but she remained quiet. "You've got a nice little body," he said, his voice rough and unsettling. "I bet you're a real wild one in bed, huh?"

Esmie stayed silent, looking out the window as the car made its way down dark streets. The man continued his crude comments, making her skin crawl. "I'm gonna have some fun with you tonight," he said, reaching over and squeezing her thigh.

Esmie shifted uncomfortably, but didn't say anything. She just wanted to get it over with and go home. Finally, they pulled into a dark alley, and the man parked the car.

"Alright, let's see what you got," he said, grinning at her. "Get out of the car."

Esmie hesitated for a moment before obeying, shakily stepping out of the vehicle. The man grabbed her by the arm and pulled her towards the hood of the car. "Take your clothes off," the man growled, his rough hands already reaching for her.

Esmie hesitated for a moment, feeling a rush of anxiety, but she knew she needed to comply if she wanted to get paid. She slowly lifted her top, revealing her perky breasts, and slipped out of her skirt.

"Leave the boots on," the man said, tossing her clothes onto the passenger seat.

Esmie tried to ignore the man's crude remarks, but the way he touched her made her skin crawl. She kept her eyes downcast, trying to avoid his gaze as his hands roamed over her bare skin, feeling her up as if she were nothing more than an object to be used for his pleasure.

He ran his fingers over the soft curves of her breasts, pinching her nipples roughly until she winced. "You got a nice set of tits on you," he sneered. "I bet you love it when a man plays with them, don't ya?"

Esmie bit her lip, trying not to react as he continued to paw at her body, his rough fingers trailing over the smooth skin of her thighs and ass. She felt exposed and vulnerable, standing there naked except for the boots on her feet.

The man grabbed her roughly by the arm, pulling her towards the hood of the car. "Bend over," he growled, pushing her forward until her hands were flat against the metal. "I want to see that sweet little ass of yours."

As Esmie bent over the hood of the car, she felt the cold metal against her bare skin, causing her to shiver involuntarily. The man's rough hands traced over her curves, starting at her hips and traveling up to her back, his fingers digging into her flesh. She felt violated and disgusted, but she knew she had to endure it.

The man's voice was thick with desire as he leered at her, "Damn, you've got a nice little body, don't ya? Can't wait to use it." His hands moved to her breasts, groping them roughly and making her wince in pain. " You're gonna be my little fucktoy, ain't ya?" He continued, his breath hot against her ear.

Esmie bit her lip and nodded. She couldn't wait for this to be over, for him to give her the money and leave her alone. She closed her eyes tightly, trying to block out the sensations and the man's voice.

The man's hands traveled down to her thighs, spreading them apart and positioning himself between them. "You ready for me, baby?" he growled, his hands gripping her hips tightly.

Esmie nodded, not trusting herself to speak. She just wanted this to be over and done with, to get away from this disgusting man and the dark, seedy alley.

As he positioned himself, Esmie suddenly remembered to ask him to put on a condom. "Wait," she said, standing back up, "You need to wear a condom."

The man's annoyance was palpable. "You serious?" he grunted. "Don't be trying to pull any shit on me now."

Esmie stood her ground, trying not to let his aggression scare her. "I'm serious. I don't do anything without protection."

The man let out a frustrated sigh, but begrudgingly pulled out a condom from his pocket and put it on. Esmie took a deep breath, feeling slightly more at ease knowing she had taken that precaution.

As he rolled the latex down his length, Esmie couldn't help but look down and get a glimpse of his shaft for the first time. It was average-sized, but unappealing to her, with veins protruding from it and a slight curve to the left. She quickly averted her gaze, not wanting to look at it any longer.

The man started to thrust into her with force, and Esmie winced at the feeling of his rough, calloused skin against hers. His heavy, flabby stomach pressed into her backside with each push, making her feel suffocated and trapped. She tried to focus on anything else, but his grunting and the sound of his body slapping against hers made it hard for her to concentrate.

"Come on, baby, you like that?" the man grunted, his hands gripping her hips tightly.

Esmie didn't respond, just gritted her teeth and tried to endure it. But then the man's thrusts became harder and more aggressive, and he started to spank her harshly, leaving his handprint on her ass. She gasped in pain as he pulled back on her hair, lifting her head up and causing her back to arch, her nipples rubbing roughly against the cold metal of the car hood.

The man's rough treatment continued relentlessly, causing Esmie to lose all sense of time and space. She was lost in a haze of pain and discomfort, desperately wanting it to be over but unable to do anything to stop it. Finally, he pulled out suddenly, and Esmie gasped for breath, her body trembling with exhaustion and fear.

As the man took the condom off, Esmie's heart sank. She tried to protest, but the man only sneered and flipped her onto her back so she was lying on the cold metal of the car hood. He roughly drove back into her, his movements becoming even more erratic and forceful. Esmie felt like she was being pounded into the hood of the car, her body bouncing with each thrust.