Underpass at Night

Jill was walking back home, after a fun night out with her friends, in the euphoric state of half-drunkenness. Her high heels clicked loudly on the sidewalk, as she hurried her steps eager to lay down on her bed and rest after a couple of gin and tonics and several free shots from the bartender and some guys from the table next to theirs.

She stood still for a moment at the descending path leading to the underpass allowing for a quick crossing of the city's main, and heavily trafficked, avenue.

However, the underpass, so late at night, was not a safe place to be; it was used as shelter by junkies and crackheads, most of them living inside the abandoned for years shops that once upon a long time thrived.

It was a 50-50 shot: either the addicts were already high on junk, in which case they'd be nodding on and off consciousness and hence would be practically harmless, or, they were desperately searching for their next fix, in which case they'd be highly dangerous.

Odds were, Jill thought, that most of them would have already gotten their fix and therefore it'd be safe for her to use the underpass; exhaustion kicked in, which made the decision-making process far easier for Jill, who decided, after a deep breath, to use the underpass. All she had to do was walk steadily and fast and not look at anyone who might be lying on the pavement, as well as ignore any derogatory comments thrown her way.

Easier said than done, however, since, as soon as she stepped into the underpass, she was met with catcalling from three young men sitting outside a half-open door smoking cigarettes and drinking beer. She hastened her step, keeping her gaze fixed at the underpass' end; in two minutes, max, she'd be back on the streets, on the sidewalk, out of the underpass...her lightheadedness was not very helpful, however, to her quick escape plans.

Her steps were uncertain, she stumbled once or twice; overly quick, one of the men walked next to her, sporting a wide, wicked grin.

"Are you lost, honey? The hookers' corner is quite a long way from here," he chuckled and his friends followed suit.

Jill tried to remain indifferent—definitely, she began regretting her outfit choice: a tight mini-dress with a deep neckline was more than appropriate for a fancy bar, but, certainly not for a late-night walk through dark streets, or, an underpass known for sheltering addicts and rough men.

"How much do you charge for a blowjob, huh?" The man insisted. "Come on, honey, don't be like that. You'll like the tool, don't worry. A classy bitch like you must have seen all sizes and shapes, huh?"

He groped her ass and laughed coldly; purely out of instinct Jill turned around and slapped him across the face with all her might. Aghast, the man held his reddened cheek; without, however, losing his smile.

Jill tried to run on her high heels, but, in seconds, she found herself with her back against the graffiti-covered wall and a sturdy, dirty hand tightly wrapped around her neck.

"You like it rough, huh?" The man said, his face mere inches away from hers. "Good; we, too, love a classy bitch that can play rough," he chuckled in her face, his breath reeking of cheap beer and even cheaper pot.

He shoved his hand under her dress, groping her bare pussy, "no underwear," he noted with a smirk. "Did you forget them at your client's place, honey?"

"I'm not..." she protested, her voice coming out hoarse.

"A virgin? We know," he rebuked. "Come on, how much for a blowjob?" He asked again, pushing her hard against the wall.

"Leave me alone," she pleaded, the words stuck in her throat as he squeezed.

"Not before you make me come, honey," he said coldly. "It's been a while and I've really missed a pair of nice, soft lips like yours around my dick."

Jill struggled to escape his grip, while he rubbed her pussy raw; suddenly, she noticed she had been surrounded, his two friends leaning on the wall sporting wide, sinister grins.

"How much for blowing all three of us?" The leader asked. "My friends haven't seen any action in months, either."

She couldn't move a muscle now, as the other two guys fondled her breasts and legs; a hand caressed her ass, her dress was lowered around her breasts, a warm tongue licked her nipple...she had no strength to fight back and quickly found herself unwilling to do so...

Foreign sensations overwhelmed her, as the tight grip around her neck loosened up just enough to make breathing slightly easier, while five hands were all over her body, turning up her body temperature and causing a wetness to rise down south...

"See, honey?" The first man said and shoved his moist fingers in her mouth. "I could tell you were a fucking whore...you're already wet and ready to serve us. I bet you taste like heaven, huh?" He shoved two fingers in her mouth.

"Maybe, she'll do us for free," one of the other men said. "Maybe, she's just a slut, man."

"Are you just a slut, honey?" The leader asked her, then thrust his fingers in her cunt. "Yeah, you are," he continued. "A used-up slut, sucking and fucking cocks everywhere you go."

"Let me go, I'm not..." she protested, albeit weakly, as the man fucked her with three fingers. "Stop, please, I..."

"You don't want us to stop, honey," the leader said grimly. "Why are you still pretending to be an innocent little virgin? We all know half the town has already been in you, honey.

"Quit the games. You love it; don't you, honey?" He brushed his lips against hers; Jill tilted her head sideways, desperately trying to avoid the stench emitting from his mouth.

"She thinks we're too dirty for her, man," one of the guys said. "A classy slut like that, she probably only goes down for suits and rich folk; she thinks our cocks are beneath her, man."

"Is that true, honey?" The leader asked her, feigning sorrow. "Do you only let rich boys use your body? Don't you know that rich guys can't properly fuck? They all secretly fantasize about having their asses fucked by their butlers...

"Come on, honey, don't tell me you're one of those gold-digging bitches; you're far too pretty to be a rich kid's flavor of the week."

What's wrong with me? Jill thought sullenly; she writhed, when a finger teased her asshole. Why's this turning me on so much? I didn't...was it a subconscious desire, when I chose to go through the underpass? Was I half-expecting...secretly wishing for it?

"Come on," the leader dragged her away from the wall and pushed her, forcefully, toward the half-open door of a former kiosk, "let's get away from indiscreet eyes; we don't want passersby to ruin it for us; do we, honey?"

Jill managed to keep her balance—as the three men surrounded her, their hands still all over her body—and stepped inside the former kiosk; a ransacked small room with a dirty mattress in the middle, amid the rumble of what once used to be a thriving business.

"There you go," the leader pushed Jill down on the worn-out mattress; she looked up and they whipped out their hard cocks. Her eyes popped wide open, as they towered over her, erect and ready; her heart leaped up in her throat, yet, her body was warm and her pussy wet, not only ready, but, overly eager for the next act...why? was the sole question ringing in her mind continuously, still unable to comprehend the reasons behind her excitement and anticipation.

"On your knees," the leader pulled her up by the hair. "Good girl," he caressed her cheek with a smile, before slapping her cheek with his cock.

All three cocks rubbed on her face, slapped her shoulders and breasts; are they right? she wondered silently, hungrily accepting them down her throat, blowing them and stroking them in rotation. Am I really a slut? Did I choose the underpass, secretly hoping something like this would occur? Why do I so thoroughly enjoy being in this position, in this abandoned place, with...

They slammed their cocks down her throat, brutally pounding her mouth; Jill stared straight into their eyes lustfully. Hands were all over her exposed breasts, fingers rubbed her clit, her asscheeks were spread...she had no power to control the action, she was body and soul at their mercy and that, inexplicably to Jill, only further increased her wetness.

The leader pushed her down on her back and put her legs up on his shoulders.

"We better use these," he produced a pack of condoms from his jacket. "We don't know what this fucking slut may carry." They all guffawed.

Jill moaned loudly, when the leader of the pack went down on her, his warm, sticky tongue licking her labia, teasing her clit. The other two were on their knees next to her head, twisting and pinching her erect nipples, slapping their cocks on her lips and face.

The leader flapped his tongue rapidly inside her, one finger inserted in her ass...Jill's moans grew louder and louder, unable any longer to control herself, having resigned from her effort to conceal the great enjoyment that had overcome her.

"That's it, man," one of the guys said to the leader. "The bitch is in heat and ready to get slammed!"

"I told you," the leader addressed a heavily moaning Jill, "you were going to love it. And you didn't believe me, honey, did you?"

Jill did not respond; her mouth stuffed with a thick cock fucking the inside of her cheek, the mushroom head stretching her lips wide. Her body tensed, when the leader penetrated her, unceremoniously driving his cock balls deep in her.

The leader kissed and licked her calves, as he fucked her hard; suddenly, one of the other guys sat on her face, shoving his balls in her mouth.

"Lick them good," he demanded, "or, it'll be my asshole you'll be licking next...and I haven't had a shower in weeks, love."

The third one played drums on her breasts with his cock, sporting a beaming smile.

Jill twirled her tongue around the hairy, smelly balls, sucking them off to the best of her abilities, while her entire body rocked under the hard penetration of the leader.

Once more, she found herself questioning her morals and desires; she'd never been in a situation like this, all her previous sexual encounters consisted of simple, vanilla positions, and were always one-on-one. Never had anyone sat on her face, never had she had three guys surround her and treat her like a mere plaything.

Granted, she enjoyed dressing provocatively on occasion; she adored the attention it garnered her, she thrived on guys buying her drinks, or simply staring lustfully at her...but, that was it. She'd do it maybe once in every blue moon, simply to boost her self-confidence.

And now she questioned all her choices and what she believed about herself, as she found herself close to climaxing while being roughly fucked by a nameless homeless man and sucking the balls of another nameless thug...

The leader spread her legs wide, increasing his tempo and howling in sheer satisfaction.

The man on her face climbed off and tilted her head over the edge of the mattress; he shoved his cock down her throat, holding it in until Jill slapped his thighs in desperation. In he went again, balls deep, jerking his cock off over her throat; Jill could see nothing but his hairy balls, while he rubbed her neck and, consequently, his cock.

"Come on, guys," the third man protested, "I'm tired of being on the sideline!"

"You're right," the leader acknowledged his presence and pulled out.

He flipped Jill around on her stomach, then slithered down under her. "Hi," he winked, as he grabbed her waist and lowered her down on his cock.

She rode him hard, taking him all in, grinding her body on his crotch; the other two momentarily simply looked on, stroking their shafts. Then, one of them crouched behind her and Jill's jaw dropped, when he spat on her ass and spread the saliva with his finger, gently using it to stretch her tight asshole.

"No, no, not there...please," Jill mumbled, horrified of having her ass penetrated for the first time...it was too little too late, the man went in, slowly burying his inches deep in her.

The pain at first was unbearable; Jill cried out in the dark room, tears streaming down her eyes. Her body stiffened and contracted; the leader moaned, as Jill had become even tighter, her pussy having a firm grip around his tool. Gradually, the pain subsided and, as both men slammed her, it was completely eclipsed by the wild sensations of pleasure that swarmed her mind and body.

"We better shut you up," the third man said and shoved his cock down her throat, "or, someone will hear you and call the pigs."

It was one of the most (if not the most) intense moments of Jill's life, as she found herself pounded airtight in a dusty little room; the strange men continued their vicious assault on her holes, pounding away hard, stretching her out. Their heavy grunts was the sole sound echoing within the empty walls.

She was rendered perfectly still, trapped between the three bodies and it was precisely that sense of utter helplessness that pushed her mind over the edge, with orgasmic waves traversing her spine after every long, deep, synchronous thrust reached deep down her throat, pussy, and ass.

There was no room anymore for questioning, for wondering...Jill had wholeheartedly embraced the fact she immensely enjoyed the situation and all she cared about was the oncoming climax that had her toes curled and her stomach contracting.

The first to come was the man in her mouth; a stream of cum was released deep down her throat, forcing her to gulp down every drop...he remained in her throat and Jill could feel the hot cum gliding down...she sucked him clean, staring straight into his eyes gratefully, while he smiled sardonically and slapped her with his dick.

The other two pulled out almost simultaneously, leaving her gaped; Jill finally erupted in a strong climax, which had her squirting all over the dirty mattress already covered with dried-up sex.

They shoved their pricks in her face, both heads finding their way inside her mouth, as she licked and sucked them both, down on her knees and rubbing her gushing cunt; they were stroking fast, heavily moaning, and in seconds they both unloaded.

It was more cum than she had ever before encountered, both men shooting a seemingly endless stream of thick spunk. A thick layer cum drenched her face and chest and the sensation of being thus covered further numbed her mind and body, while she finger-fucked herself to a second orgasm.

"Shit, man," the leader of the pack said befuddled, after Jill had sucked him clean, "the whore wants more!"

"I'm all emptied out, man," one of the other said.

"Yeah," the third one agreed. "I'd much rather have a beer now," he lit a cigarette and the blue smoke lingered on in the small, airless space.

"I don't know, guys..." the leader replied thoughtfully, staring intensely at Jill. "Keep playing with yourself, slut," he prompted her, patting her head, "you might get lucky and get us horny again."

"Sorry, I'm out," the smoker said and stepped out of the former kiosk, quickly followed by the other.

"Looks like it's just the two of us now; huh, honey?" The leader smirked at Jill, who looked up at him with exhaustion and satisfaction.

"Yes," she replied in a shaky voice; then, she bit down her lips, as she brought herself to a third orgasm, with cum still drying up on her skin.

"Good girl," he nodded approvingly and scratched his chin. "Though," he sighed theatrically, "I'm afraid I'll have to side with my friends...seeing you all used-up like this doesn't do it for me, honey...you were far hotter, when you were uptight and acting the prude virgin.

"Don't worry, though," he told her with a wink from the doorway, "there are more of us down here; and many are far too desperate for a nice piece of ass to give a damn about how used up it may be."

After the door was closed, Jill found herself alone in the dark, still rubbing her dripping pussy; she looked about, panting, at the half-broken shelves, the broken register...she had finally time to take in the atmosphere wherein moments ago she was fucked by three nameless men...

Her excitement once more increased, despite her three climaxes; she stopped playing with herself and remained on her knees, panting heavier and keeping her gaze glued to the shut door.

Was she truly eager for round two? The question rang in her head thunderously, tormenting her thoughts, while she rocked back and forth in both anticipation and nervousness, trying to listen for any footsteps from the underpass...she fixed her dress, cum still drying on her skin, and decided to linger on for a little while longer, not yet ready to give up on the chance for a potentially even more exciting round two.