Trick or... No, Just a Trick

Here's another one-off story inspired by Halloween. As always, comments and feedback are appreciated. Enjoy.

*****

Samantha checked herself in the mirror. Her makeup was overdone; too much rouge, lipstick way too red, and eyes done thick with both mascara and blue eye shadow.

"Perfect," she thought to herself and felt an excited little charge course through her 22 year old body. Every Halloween through high school and college she had watched enviously as friends and roommates dressed in the sexiest (really sluttiest) way imaginable and went to parties, coming back with stories of drunken hookups with random guys. Samantha was far too reserved to let herself go like that, and when she was younger there was always her parents to consider.

Having graduated from college earlier in the year and found her first "real" job and first stand alone apartment, she had still hesitated when friends from work began to pressure her into coming to this Halloween party at a local bar.

"Oh," said her stunningly gorgeous and blonde friend, Nicole, "Just dress as sexy something or other, I'm going as a sexy nurse."

"Slutty nurse, more like it," Janet added and then giggled, "I'm squeezing into my old school uniform... I used to think it was very dour, but trust me when I say I have filled in enough to give Nicole a run for her money."

Samantha begged off, the butterflies in her stomach signaling both her desire to go and the shyness that had always kept her home. Nicole and Janet shrugged and let her know the address if she changed her mind.

Now she stood in front of the mirror, dressed in a make-shift hooker outfit, tube top that barely contained her breasts and left her stomach bare, an impossibly short leather micro mini, thigh high stockings and stiletto heels. Truth be told she felt as sexy and slutty as she ever had, but wasn't convinced she had the confidence to leave her small apartment.

"Okay," she took a deep breath, "I can do this. I want to do this. It's just a bit of fun on Halloween." She hesitated as she took her black woolen overcoat from the hook near the door and took another deep breath. Putting it on, she realized the coat, cinched at her petite waist, fell lower than her skirt and actually made her look even sexier. She unconsciously bit her lip as she turned right and left checking her profile in the full length mirror and then steeling herself, walked out the door.

Samantha's heels clicked along the wet pavement of the nearly deserted street as she made her way to a more populated area, increasing her chance of hailing a taxi. As she did, she noticed an increasing number of eyes turning her way, even with the overcoat, she realized, she was a bit of a spectacle.

Suddenly a taxi came up behind her, speeding by, and by the time she raised her hand to hail it, it was already past her. Miraculously, however, it slowed and stopped, and the click-click-clicking of her heels sped up as she did her best to move faster on the stiletto points under her feet.

Before she could reach the cab, however, a well dressed man reached out and, paying her no mind, opened the door and slid into the seat.

"Hey," she cried out, trembling with a desire to get out of public view as she reached the bright yellow car before he managed to close the door, "you stole my cab."

He gave her a curious look, glancing up and down her body, covered mostly by a coat that came to her mid thigh. Whatever she wore underneath, it didn't show at all. Just the black material of the coat, flaring out, met by her shapely legs in black stockings. Returning to her face he saw that she wore heavy makeup, blue eyes highlighted with blue eye shadow and thick mascara, red lipstick painted on a pert mouth. He guessed her to be about half of his 45 years, but maybe older. It wasn't raining at that precise moment, but the sky was threatening and a downpour would ruin her.

"Tell you what," he said, "I'll let you share it with me."

"But you stole it," she whined.

He chuckled, "No, I really didn't. And in any case, I'm in here and you're out there. There is little you could do to change that now."

Suddenly she felt very small, and not for the first time that night.

The cabbie grumbled about the delay and the nicely dressed gentleman looked up into her big round eyes with a confident if not smug smile, "Last chance, come with me, or stay out here in the cold and wet until another cab happens along. Could be a while, Halloween is always a busy night."

"Fine," she let out an exasperated sigh as she slid her body into the taxi and next to his. She noticed that he wasn't unattractive, for an older man, but then she always did prefer her men a little older.

"So, where are you headed?' His eyes wandered down to her where the hem of her coat laid across her stocking clad thighs.

"Um," words caught in her throat as she noticed him checking her out. Her body flushed at the thought and her voice became quiet, "A Halloween party."

He gave her a funny look. "Halloween party?" he asked, "Don't you need a costume for one of those?"

"I, um," she was suddenly very self conscious. Of course she had planned to wear her costume out, but it was supposed to be around an entire party full of people where she would blend in with the other scantily clad young women. "It's under my coat."

He gave her a wry smile, "Can I see it?"

She felt her entire body flush. "Um, no," she replied holding her hands high up on her coat holding it together in a defensive fashion. "I don't think so."

He glanced up and down her body again, as if appraising her. "Okay," he said turning toward the window, adding a dismissive, "I see."

"What?" She asked defensively. "What do you see?"

He let go a sigh turning back toward her, "I get it, pressures on young women such as yourself, make you self conscious about your body. I mean, you're very attractive, but I can see how you might have dressed in a provocative costume only to decide to never show it to anyone." He patted her knee lightly, condescendingly. "It's okay if you're not all together confident in your body."

"Excuse me?" she said suddenly enlivened and defensive. She sat up and leaned toward him letting go of her jacket and as it parted he could see that her top was necessarily cut low since he couldn't see it in the space the coat had opened.

"Look just because I don't want to show you my costume doesn't mean I have body issues. How full of yourself are you?"

Through her abrasive response he remained stoic. "So if it's not shame keeping you back, what is it?"

The comment left her dumb for a moment. "Fine," she said rolling her eyes and moving to unbutton her coat. "It's not a big deal; it's just Halloween."

She opened her coat and shrugged it off revealing the tube top and micro mini that ended remarkably high on her thighs in her seated positions. The stockings she wore were thigh highs, which he could see because the stocking tops and the garter that held them in place were clearly visible an inch below the hem of the skirt.

He glanced from her legs back to her face and held her eyes as he said flatly, "So you're a prostitute."

"Dressed as a prostitute," she corrected him and folded her arms in front of her chest falling into a pout.

The taxi stopped at a red light and a car full of college aged men pulled up next to them. She turned toward them. Looking out her window without her coat on, they could see her tube top, combined with her hair and make up, and one of them said too loudly, "Holy shit, that rich dude in the cab picked up a hooker, look!"

Next thing they knew, the young guys were hooting and hollering at them, shouting "How much?" and encouraging her to "do her job."

She tried to look straight ahead and ignore them, but couldn't help glancing back their way several times. She was embarrassed, and her cheeks burned redder than the rouge she wore, but if she were honest, she'd admit to herself a little thrill about that entire car of young men thinking of her as a sex worker. Somehow, it proved she got the costume right, but mare than that, despite her shyness it had always aroused her to know that men were thinking of her sexually.

As a cheerleader in high school, she caught the looks from both her classmates and the older men who came to the football games. After a friend had teased that every man in the stands imagined fucking her, she couldn't get the thought out of her mind. On game nights she would race home and bring herself to orgasm thinking of the looks she got and what the men behind them were thinking.

But that was a little different. All women know what it's like to have men stare at them with sexual intent. The guys in the next car thought of her as somehow worse, someone whose body they could buy and use without care or concern. It was so depraved, but she found herself biting her lower lip at the thought.

"You should put your coat back on," the older gentleman next to her in the cab advised, and motioning with a nod of his head added, "people could get the wrong idea."

Turning to him, she smiled smugly believing she had the upper hand, "Now who's ashamed? What's the matter? Don't want people to think you'd pay for sex?"

The corner of his mouth turned upward in a smirk, "Oh, I've hired an escort or two, so no, it's not that."

The admission caught her off guard. "Really? Why? You're not..." She stammered, "I mean, you don't seem like the type that has to..."

"Oh, it's not that I have to do anything," he explained calmly. "Look, you're young, but maybe you'll understand. You ever just want to fuck?"

He waited for a reaction but she just stared at him blankly so he continued, "I mean look, even the most casual affair carries with it an exchange of names, the possibility of a second meeting, a follow up phone call, emotional neediness. That's all well and good, and important, but sometimes I just want to fuck, empty my stress into her, and not have to worry about being followed home. You understand?"

She nodded dumbly but she didn't really understand. Cognitively she followed the sentiment, but her experience was limited and despite feeling somewhat hypersexual in her fantasy world, she only ever had had sex with men she knew well and trusted to call her the next day. She had never just fucked for the sake of fucking.

"You could do it, you know," his eyes were back to roaming over her scantily clad body.

"Do what?" Her question was meek, genuinely curious, and overwhelmed.

"Be an escort," he said matter of factly, "I mean most girls can street walk, but you're pretty enough to demand more than that."

She wasn't really sure what to say, caught between embarrassment and indignation, but somewhere she recognized his comment as a compliment and whispered, "Thank you."

"Have you ever thought about it?" His eyes were steely as he looked at her. He wasn't joking or teasing; he was feeling her out. She bit her lower lip again.

"No," she lied, "Of course not." The thought had never quite come to the point of fantasy for the young woman, but every Halloween she thought about how easy it would be to dress slutty and go to party and just some random guy. Since deciding her costume, she had pictured herself in the role of prostitute, wondered how easy it was, thought about how depraved it would be to take money to suck some guy off in an alley. Now she was thinking about it again.

"Pretty girl like you could make quite a bit, I'd think," he said idly as he turned his gaze toward the window and the wet pavement flashing by.

"H...How much?" her voice was small, but he could tell she was hooked on the idea.

"Oh, I don't know," he mused thoughtfully out loud, "Young, attractive... probably $100 just for a blow job."

"Oh wow," she breathed, "You think that much?"

"Well," he considered, "It depends on if you're any good. Do you have much experience giving head?"

She blushed fiercely and felt herself moisten further at the personal question. How on earth did she come to this point? Discussing her oral skills with a total stranger?

Lacking almost any confidence, but determined to prove her worth, she answered, "My boyfriends have told me I'm pretty good."

"Oh yeah?" he said calmly. Then with no sense of irony, only a firm stare into her over made up, but still pretty blue eyes, he produced a $100 bill, holding it up in front of her, and said, "Show me."

"What? Here?" She felt the butterflies in her stomach and the trembling of her hands; her thighs squeezed together sending a shudder through her lithe body. But they both noticed she hadn't said no.

Her eyes went wide, glancing from the bill to this stranger's face which remained stoic; she had let the conversation go too far and now she was being propositioned for real. She had only intended to dress as a whore, not become one.

Her pink tongue darted out and moistened her lips, and with eyes lowered, not in shame, but curiosity about what lay within his trousers, she reached out to his hand and grabbed the bill from it, shoving it in her clutch, before turning sideways in her seat.

Hesitating half a second to glance at him, her innocence and inexperience shown through the heavy make up of the costume and he smirked to himself about how easy it was to bring her to this moment. When the moment lasted a bit too long, he gave her another shove, "You took the money... now you need to do what I paid you for."

She swallowed hard and with no grace or dexterity, she reached for the belt of his trousers and fumbled her way to getting it open. Once undone, she continued by unbuttoning his trousers and lowering his zipper. So focused on her task, she didn't notice the furtive glances in the review mirror as the cabbie kept one eye on the road, but only one.

When she freed the man's cock from his pants, a man whose name she hadn't even bothered to learn, her eyes went wide at the size of it. In truth, while it was an above average seven inches, neither of her past lovers came close and she marveled at its size and thickness in her small hand.

She could feel it pulse and twitch as she took a firm grip and began stoking it up and down, watching it grow. Then, almost as if she were inhaling a deep breath before jumping into a pool, she breathed in and lowered her head into his lap, letting the head slip into her mouth even as her hand still jacked his base.

He rested his hand on the back of her head, lightly gripping her hair but not forcing her or controlling her in any way. No, as she began to slide her lips up and down his shaft it was all her doing. Somehow her lack of skill was a turn on itself and managed to make up for her unwillingness, or inability to take him too deep into her mouth.

When he raised his hips to meet her downward motion she moaned and the vibrations rippled through his shaft causing him to grip her hair a little harder as a reflex. This in turn urged her down further on his cock until he felt his head touch the back of her throat, causing her to briefly gag, but to her credit she just kept sucking.

"Such a good little whore..." he groaned aloud, uncaring about the cabbie's wandering eyes.

Hearing herself called a whore evoked a muffled squeal of objection, but then she remembered, she was sucking a stranger's cock for money. She was a whore in every sense of the word, and somehow the thought made her moisten.

She redoubled her efforts, feeling him swell further against her wet, pink tongue, stretching her lips. He was close, and she smiled such as she could thinking about how quickly she had got him there. Maybe she was better at this than her previous experience had led her to believe.

"Fuck..." he groaned, feeling his orgasm coming, but trying to hold back. "I'll give you another $300 if you let me fuck you..."

She pulled her mouth off of his cock with a slurp and a pop, reveling in the idea that he wanted more of her and was willing to pay for the pleasure. "How about $400?" She said before encasing his cock in her warm mouth once again.

"Fine, " he groaned, "straddle me."

She lifted herself back up and pulled her tiny skirt up over her hips as she swung one leg over him. She ground against him, her thin thong in the way of penetration. "Money first," she said holding out a hand like a petulant girl.

He reached into his pocket and pulled four more hundred dollar bills out and handed them to her as her hips ground against his painfully erect cock without letting him inside of her.

"Condom?" She more demanded than asked. And while she acted purely business like, she could feel her own desire to have him inside her growing.

"No," he shook his head and bit his lip, holding himself back from forcing his way inside her, "no condoms."

She felt the shiver of denial when she replied, "No condoms, no sex." But she was still grinding against him.

"Oh fuck..." he groaned again, "please..."

"Ok," she said matter of factly, but secretly shivering at her complete embrace of the role she had adopted for Halloween, "But it'll cost another $100."

Without hesitation he slipped her another hundred dollar bill. Reaching between her body and his, she took hold of his cock and forced her thong to the side, lining his head wet into the opening of her slick cunt.

As she pushed herself down, impaling her tight little body on a cock bigger than any she had previously taken she moaned out, "Just don't cum inside me..." but even as she said it, she knew there was no way to enforce that condition.

He pushed up into her and felt her give way to accept his sizable tool. With three upward thrusts he had buried himself inside her and could feel her grip every inch of him. He placed his hands on her hips as she worked herself up and down, and with each downward turn, he thrust up into her, his need to cum only slightly stalled as a result of the brief negotiation.

For her part she had never felt so full, but more than that. Playing the whore to this nameless John made her feel both in control and out of it at the same time. She had taken agency for sex with no pretense to emotion or long term stability, but then she knew he was a stranger fucking her bareback in the backseat of a cab, and she had stopped taking the pill months ago after breaking up with her last boyfriend. It was insane, but felt so good.

The combination of the mental and physical was overwhelming, and as his thrusts got more wild, she could feel herself losing control of her own body. But no, she told herself, whores don't let Johns make them cum. Whores stay in control. Whores don't get turned on when they fuck strangers.

But then, which each thought she pushed herself closer and closer to the edge of orgasm. She was a whore, but not acting like one, because she was going to let...

And then she came, as hard as she had ever cum with someone else. Her lithe body shook and trembled as she let out a guttural whine as the orgasm washed over her.

Her body was alternately tense and limp, but she realized she was no longer moving up and down of her own accord. Instead the stranger fucking her had gripped her hips and was using her petite frame as little more than a tool to jack himself off, his movements becoming more insistent, more erratic, until finally he pulled her down hard and released himself deep inside her gripping cunt.

As she felt jet after jet of his hot seed spill into her all she could do was collapse forward and mutter, "Fuck..." feeling somewhere in between the pleasure of being used and resignation to the multitude of dangers that letting a stranger cum inside her young, fertile cunt offered.

He wrapped his arms tight around her as his orgasm finished filling her with his cum. And when he was done, they were both out of breath.

He directed her to slide to the side and off of him, and when she did, she could feel his ample cum slip out of her, soaking her thong and running down her thighs.