Hailey Needs Help

Story Info
A girl never forgets her first time.
5.2k words
4.54
37.9k
22
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
HuckPilgrim
HuckPilgrim
438 Followers

"Kiss it, Hailey," the whore whispered.

Hailey glanced around the darkened theater. The boy who sat between her and the whore had his fly down, his erect penis jutting from his pants. The whore held him by the shaft.

Hailey grinned.

Smirking, the whore lowered her head into the boy's lap and his face suddenly crumpled into an expression of undisguised lust. His mouth fell open and his breathing came quick and hard. He was a good-looking boy with a square chin and smoldering eyes. He had looked so cool and aloof in the park. The whore raised her head. She mumbled something to the boy as her hand massaged his now glistening shaft.

He closed his mouth and nodded. He didn't look so aloof anymore.

A deep needy place opened in Hailey's chest. She was eighteen but didn't look it. A too-small frame and narrow hips.

"Ready?" The whore whispered.

The boy squirmed and made an impatient noise in his throat. The whore cut her eyes to him, a no-nonsense look on her face. Taking the head of his penis between her thumb and forefinger, she pinched.

The boy pursed his lips together.

Hailey looked to the whore for direction. Wild black curls framed her face. At this point, Hailey didn't know the whore was a whore. All Hailey knew was that her friend was mysterious and cool, a beautiful girl who always wore impossibly tiny shorts or minis that showed off her long legs. Hailey's brother had forbidden Hailey to hang out with the whore, so, of course, Hailey had begun to sneak. The whore raised her brows, her lip curling into a mischievous smile.

Hailey swallowed, wetting her parched mouth.

This was wrong.

She didn't even know this boy.

But his cock was the first she'd ever seen and it was such a beautiful thing: long and slender and ruddy, with a big fat knob at the tip. Her brother would kill her if he knew she was sitting next to a boy with his fly down. The whore had a boyfriend, but he didn't seem to mind who she hung out with, or what she did when she wasn't with him. These were the thoughts that were going through Hailey's mind as she tucked her hair behind her ear and lowered her head into the boy's lap. His cock warmed her face. Pressing her lips against its length, she gave him a dry kiss. Her mind screamed for her to retreat, to pull back, but just then a great pulse of heat swelled between her legs. Hailey gasped at the intensity of the feeling, her mouth falling open. Before she could think another thought, she put her mouth on that tasty prick, letting its silky warmth slide across her tongue.

The boy began undulating his hips.

Hailey changed her position to accommodate his movements. His cock slid deeper into her mouth. He took her head in both hands. As soon as Hailey felt his hands on her head, she regretted her choice, but by then the time for turning back had already passed. He came, hot semen filling her mouth. She tried to raise her head, but the boy held her fast. Soon something wet came trickling out the corner of her mouth.

He was making soft grunts.

Hailey stopped struggling and swallowed—again and again, she swallowed. Her entire focus was on receiving the hot juice hosing into her mouth. She knew he was finished because he relaxed his grip and began petting her head.

Hailey let the cock fall from her mouth, sheepishly raising her chin.

The whore was grinning at her.

The boy had a rapturous look on his face.

Hailey wiped her mouth. She hadn't expected things would go that far, that quickly. She wasn't sure how to respond. Tears were welling in her eyes, but she didn't want to cry. Her pussy was throbbing with desire.

The boy was fumbling with his pants.

Before Hailey could decide how to react, the whore was on her feet, climbing past the boy and grabbing for Hailey's hand. They dashed into the sunlight, leaving the boy in the dark. Hailey had time to compose herself, and she decided it was probably best to play it cool. The whore was a much different type of friend than anyone she'd ever known before—more adventurous, wilder. They spent the rest of the afternoon on the amusement pier, flirting with young ride operators and the old man concession vendors. They rode the Ferris wheel and the Rotor for free. They were given candied apples on a stick and spun bales of cotton candy, which they promptly threw away. The challenge was just in receiving them. Hailey steeled herself to suck more cock, but it never came to that. Later that night, she climbed into her bedroom window, stripped down to her undies, and slipped between the cold sheets where she promptly pressed a fat pillow between her legs.

The next morning, Hailey couldn't look her brother in the eye.

She'd sucked cock.

And she'd been ready to suck even more cock.

More than that, it was fun to be a cocksucker, and she'd thoroughly enjoyed herself. Maybe it was the most fun she'd ever had in her life?

Hailey could see where all this was headed. She knew straight away what she had to do. To be worthy of her brother's love, she would have to fight her way back to being a good girl. As soon as she thought it, her heart sank. She would be abandoned by the whore. At the very least, she would make fun of Hailey, the same way she'd mocked the boy in the theater, or those old men who ran the concession stands on the pier.

The sky outside turned dark and grey.

The whore texted Hailey but she didn't respond. She plodded ahead, alone.

In the middle of the night, Hailey's mind would go to the beautiful prick she'd seen in the darkened theater. Sometimes she would forget that she no longer wanted to be a cocksucker and would put her thumb in her mouth for comfort. On nights like those, Hailey would clamp a pillow between her thighs and try to tame her libido by grinding herself to the very edge. It was self-indulgent. Occasionally she would catch herself and race to the shower, cold water beating against engorged nipples until she emerged from the stall, shivering and indifferent. More often, though, she would simply fling the warm pillow across the room, lying on the bed with her knees spread lewdly. Hot, panting. Guilty.

Hailey needed help.

Summoning all her courage, she shared her plan to stop sucking cock with the whore. To Hailey's great surprise, the whore responded warmly. Hailey's heart soared. The whore even offered to stop sucking cocks herself.

"Good girls," the whore said.

She invited Hailey to her house to play dress up games. They wore button-down shirts, with plaid, pleated skirts, and saddle shoes. The whore produced a camera and the girls took turns making indecent poses. Hailey sat Indian style with her crotch exposed, the whore's cigarette burning between her fingers. In another pose, Hailey got on all fours, her skirt bunched up on her hips, grinning over her shoulder. It made her panties wet, but it was all okay because it was just a little good-girl fun. So much better than the tortured nights alone in her narrow bed.

A few days later, the whore put her forehead against Hailey's.

"Don't hate me," the whore whispered.

Hailey was shocked. Hate? How could she hate her coolest friend?

The whore hid her face. Tears were rolling down her cheeks. Hailey had never seen her friend in such a state. The whore began a sad story. Her boyfriend wasn't really her boyfriend. Instead, he was her pimp and she was his whore. Hailey's brow knotted, her mouth falling open. A whore? Her friend was silently sobbing. Hailey reached for the girl and held her. Both girls wept for a long time in one another's arms.

Finally, the whore pushed back and blew her nose.

She gave Hailey the box of tissues. Both girls dried their eyes and composed themselves. Hailey was still reeling from the shock of her friend's admission when the whore asked Hailey for help. "Anything," Hailey blurted.

"There is a man," the whore whispered. "He's willing to give me enough money to move away from this town, to escape from my pimp. Only . . ."

Hailey tilted her head.

"He wants to sleep with me and with someone else."

"Oh," Hailey said.

Her face flushed with heat. The whore was asking Hailey to join her with the man. Hailey pressed her thighs together. Her pussy throbbed with want. It was all she could do not to touch herself. She took a deep breath to steady herself. It would be wrong. Terribly wrong. But she would be doing it for a good cause, she reasoned. This logic made the warmth from between her legs rise to her tummy and then to her chest.

Hailey held her breath. Could she do it?

She nodded.

The whore grinned triumphantly.

Almost immediately Hailey regretted her choice. She remembered how she'd felt in the theater when the boy had grabbed her head. A sick panicky feeling welled up in the back of her throat. The wetness between her legs muddled her thinking.

"What will I have to do?" Hailey whispered.

Hailey pretty much already knew the answer to her question. She'd only asked because her spirit was wavering and she needed help. The whore did not disappoint. She put her head near Hailey's and whispered.

"Fuck."

Hailey shuddered with forbidden delight.

"It's easy," the whore laughed. "You just take off your pants and spread your legs."

Later that night, as Hailey lay in bed, she straddled her pillow and replayed her friend's response again and again in her mind: Fuck.

FUCK.

Fuck, fuck, fuck.

For the first time in her life, she was going to fuck.

Two days later, the whore laid out some clothes for Hailey on the bed. A slinky black tube dress, a thong, and a lacy bra. Red heels. Hailey grinned. She'd never worn clothes like these before and it made her feel strong. Her brother would be so upset if he knew.

Hailey showered.

Afterward, eyes shimmering with excitement, she stared into the mirror.

Small breasts, a flat tummy. Slender hips.

The whore came in and swept her eyes over Hailey, a smug look on her face. Hailey tried to see what her friend was seeing, but she couldn't be sure. When she stared into the glass, all she saw was a skinny blue-eyed teen, with a small cleft in her chin.

The whore fixed Hailey's hair, her makeup. Painted lips, eye shadow. Lashes. The makeup combined with the outfit made Hailey feel sophisticated and alive. So alive.

The girls went downtown to a hotel.

The whore found him in the lobby, a man in his forties. Grey at his temples, clean-shaven. He looked and acted like the father of any number of Hailey's friends. He was soft-spoken and friendly. He shook Hailey's hand, holding her fingers lightly with his own. His hands were big and dry but soft. He had a pleasant smile. He reminded her of a priest she'd once known in elementary school.

"Are you hungry?" he asked.

Hailey had never felt less hungry, but she didn't say that.

The hotel had a fine restaurant off the lobby. Hailey swallowed when she looked at the prices. The whore and the man ordered wine, but Hailey wasn't old enough to drink. After the waiter left, the man leaned forward and whispered that he had a bottle of wine chilling in the room. It was the first acknowledgment of the reason they'd gathered at the hotel, and Hailey tingled with anticipation. She clamped her thighs together and squirmed in her chair. The man ordered food for the table and asked for permission to pay.

The whore laughed and said that of course, he was paying. The man's grin widened. Some of Hailey's apprehension faded. The man showed her a picture of his daughter, a beautiful blue-eyed girl with a cute dimple in her chin. The girl looked a lot like Hailey, but she didn't say that. It seemed like an inappropriate thing to point out. Besides, her libido was racing forward with the illicitness of the situation, the promise of what was to come.

In the room, the whore kicked off her shoes, slipped her dress over her head, and then sat on the king-size bed in her underwear. The man poured everyone wine, and then sat in a chair off to the side.

All eyes were on Hailey.

She sipped her wine. It tasted wonderful, warming her throat and making her whole chest throb. The man suggested Hailey get comfortable. She understood that he probably wanted her to undress. She intended to strip for him, but she lingered, enjoying the dynamics of the moment. She kicked off one shoe, then the other. The whore made small talk with the man. Hailey downed her wine.

The man refilled her glass.

He whispered that she was lovely, a beautiful girl.

Hailey held her glass to her mouth, blushing furiously. She rarely received this kind of attention from men. He complimented her body, the size of her chest, and the shape of her hips. No man had ever said such things about her before. His words were as intoxicating as the wine.

The whore produced a hand-held camera and pointed it at Hailey.

Hailey held her glass up to hide her face. The man chuckled. He asked her permission for the video. He said he wanted something to remember her by. Hailey wondered who else would see the video, but she didn't ask. He seemed like a nice enough man and a recording would add something even more forbidden to the night. The glorious tingle between her legs intensified to a nice throbbing hum. She lowered her glass.

"Can I check you out?" he murmured.

Hailey trembled with excitement. She couldn't bring herself to answer such a question, so she downed the rest of the wine and looked away. He stroked her sensitive breasts through the fabric of the dress.

Her breathing intensified.

He cooed praise about how brave she was.

A sudden terrible feeling of regret swept over her and she looked to the whore. She was grinning, looking intensely into the viewfinder. When she saw Hailey looking, she raised her head, cooing encouragements. Suddenly the man slipped his hand under Hailey's dress and held her cunt, making her gasp. The tingling between her legs transformed into an electric current, alive and pulsing. Nothing in her life experience so far had prepared her for a grown man taking hold of her cunt. Hailey grabbed for him, leaning into his chest.

"Yes!" The whore's eyes glittered.

Hailey felt as if she were making that first breathtaking plunge on a rollercoaster.

He held her ass. His fingers snaked into her panties, spreading the moisture on her lips. Nibbling at her neck, he whispered filthy things into her ear. His language grew more vulgar. Instead of talking about her body or courage, now he said she was a hot little number who could make a grown man's cock hard. His words made her start to feel differently about herself.

Maybe she was hot?

Maybe she could make a guy's cock hard?

He knelt before her, shoving her dress up on her hips and mashing his tongue between her legs. She spread her legs, almost knocking the TV to the floor. He removed her panties and rubbed her clitoris. Delicious sensations flooded her body. He tongued her asshole. Hailey had never felt anything so intense in her life. Her face twisted in lust. She was aware that the camera was capturing her reactions and wanted to look sophisticated and cool, but then his tongue was always finding some secret spot, making her face crumple again.

He stood, taking her by the throat. "Ready for daddy?"

All Hailey could do was nod.

He gave her a deep soul kiss, exploring her mouth with his tongue. She hadn't intended to kiss him because he was so much older than her. But now that his hot tongue was thrust inside her, she tilted her head back and surrendered her mouth.

He pulled her dress over her head. Hailey stood before him in only her bra.

"Get on that bed," he commanded, pointing.

Hailey knelt on the bed, holding her tits, watching him remove his clothes.

He was not an unattractive man. He methodically undressed, carefully folding his shirt. His pants. He watched her with an amused expression. Hailey unclasped her bra and discarded it. Tugging her nipples, she pulled the sensitive little nubs away from her chest and asked salacious questions.

"Am I a hot little slut?"

"Do I make your fat cock hard?"

She had never thought of herself as a seductress. It was a new and powerful role for her, similar to trying on the dress the whore had provided, which now lay crumpled on the floor, or the lipstick smeared on her chin.

"Oh, yes," he said. "You're daddy's hot little number.

He cupped her cheek, slipping his thumb in her mouth. She suckled it.

He ordered her on her back and, like an eager pup, she complied. He climbed between her legs and rubbed his cock head on her slit. She was anticipating that big fat cock sliding between her legs when he caught her eye. "I'm sexually attracted to my daughter," he said.

Hailey furrowed her brow.

"I want to fuck her."

He pushed his hips forward, driving his meaty cock into Hailey's slippery pussy. She grabbed his torso, her cunt suddenly filled with cock. Her hips began an instinctive rocking movement, undulating against the big dick inside her. Her breathing changed too, coming fast and hard. She'd been on the brink of pleasure for so long that her hardwired instincts took over, dragging her forward. "It wouldn't be right for a father to fuck his own daughter," he husked.

Hailey twisted to look into his face.

"That's why I'm fucking you."

Hailey whimpered. The sex was the most intense thing she'd ever felt in her life, but he was making it all feel so dirty. He kissed her full on the mouth. Hailey regretted her decision to sleep with him, but it was too late now. His cock filled her pussy, his tongue her mouth. She began softly keening as he started his strokes. Big powerful thrusts that made her cheeks shake. His hands cupped her shoulders, his groin pressed against her clitoris. The worst part for Hailey was how deliciously dirty it all felt.

She crested the heights, sobbing.

He was using her as a surrogate daughter and her impending orgasm would make her an accomplice. As soon as the thought presented itself in her mind, a powerful orgasm rippled through her young body. A tidal wave of pent up sexual energy released itself. In the aftermath, shame washed over her, filling all the empty spaces in her psyche that the orgasm had swept away.

She'd finished, but he hadn't.

He kept plunging his cock into her. Soon she felt a burning sensation between her legs. Without the heat of an impending orgasm, she felt the ruined membrane in her freshly opened love tube. He didn't seem to notice. He affirmed that she was a hot little number, a girl that could stoke any man's passion. Finally, he spelled out their relationship in just a few words: "I don't mind paying to have a tight young, pussy at my disposal."

"Ohhhhh," Hailey begged. "Please don't say that to me."

He looked at her confused. Searching her eyes, he continued to work his hips.

"Does your boyfriend know you're sleeping with men for money?"

A fruity bile taste rose in her throat. Her face burned with shame. He was calling her a whore. She didn't think of herself as a whore even though she understood that—technically—she'd allowed him to use her pussy for money. All this went through her mind, while his cock speared away at her pussy, making it hard to think of a good response. She ended up saying the first thing that came to mind. "I don't even have a boyfriend."

He raised his brow.

It was an unsatisfactory reply. The skin around her eyes tightened. She wanted to shame him, to make him feel some of the horrible guilt that she was feeling.

"I'm a virgin," she spat.

His eyes widened and then he smirked. Nuzzling his head into her neck, he bit the delicate skin just below her ear. Eventually, he stopped thrusting, held her tight, and made an animal grunting noise in his throat.

After a bit, he kissed her cheek. "Not anymore," he whispered.

HuckPilgrim
HuckPilgrim
438 Followers
12