Hailey Needs Help

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HuckPilgrim
HuckPilgrim
438 Followers

Hailey felt her ears go hot.

He pulled out and warm semen oozed from her fuck hole. He took the camera from the whore and pointed it between Hailey's legs. He asked her to push out the semen that he'd just deposited. She obliged. She didn't want to tangle with him anymore. This wasn't how she had imagined the night would work out.

While he showered, Hailey dressed.

The whore had brought the clothes Hailey had worn from home. Somehow her familiar clothes seemed foreign to her now. The slinky black tube dress went into a bag, along with the shoes, thong. Bra. Everything. When Hailey looked in the mirror, a stupid little teenager with smeared makeup gazed back.

The man gave the whore a plain white envelope.

He sat with Hailey at the foot of the bed. He said he'd enjoyed meeting her and wanted to see her again. She wanted him to know she wasn't a whore, but she didn't know how to present it. He took money from his wallet, a lot of money, and he put it in her hands.

She exhaled noisily and grew agitated.

The man comforted her, talking carefully about the money. Instead of talking about money directly, he talked about her needs. He said he just wanted to help meet her needs. He seemed to understand that she needed to hear him talk about money in this roundabout way. He went on and on. Soon he talked about his daughter, her needs. He joked with the whore about the amount of money he spent on his daughter's needs. He said she was worth it.

Hailey folded the money into her palm.

He spoke with the whore.

They stood right near Hailey, but she'd retreated inside herself and couldn't follow their conversation. The whore put her hand on Hailey's shoulder, squeezing reassuringly. Finally, the man knelt before Hailey and wrote his phone number on her hand. He said he really wanted to see her again.

He promised he would make it worth her while.

Hailey looked away.

The money complicated things. She felt certain she wasn't a whore, but she wasn't able to pass up the money. These were the things that were going through her mind as she rode home in the taxi that night.

Hailey climbed into her bedroom window and slipped into bed still wearing all her clothes. Some things were just too horrible to think about, so her mind did its best to block those things out, like a redacted government letter. She didn't think about the mean way the whore had tricked her, or that the man had wanted her to pretend she was his daughter. She didn't think about how delightfully dirty he'd made her feel. But her mind's eye wasn't perfect about the things it scratched out, either. She regretted her decision to allow him to shoot the video. She found herself obsessing over little things, like the way she'd almost knocked over the TV trying to get his tongue deeper into her bottom.

To comfort herself, she focused all her mental energy on finding proof that she wasn't a whore. She kept thinking about the humiliating exchange where he'd pegged her for a whore. She cycled through that exchange in her mind, convinced that if she could have somehow come up with better answers to the questions he'd posed, he would have seen her as she saw herself: a good little girl, a wholesome friend.

It was an exercise in self-indulgence, but she didn't know that yet.

She hung out with the whore for another six months. They never discussed her moving to another town or escaping from her pimp boyfriend. It was as if those things had never been said. Hailey comforted herself with the knowledge that while she might or might not be a whore, the whore certainly was a whore.

This thought was a huge source of comfort for Hailey.

School was hard.

The girls from school were definitely not whores, but Hailey's own chastity remained in doubt until she could finish the proof in her mind. Despite furiously cycling her mind, Hailey was never able to come up with an adequate exchange that proved to herself that she wasn't a whore. Eventually, she gave up thinking this way and started to date. Unfortunately for Hailey, dating was a mistake, an escalation of her unhealthy thinking. Instead of pursuing a single conversation in her mind, she began role-playing a similar conversation in real-time. She didn't realize any of this, of course. In her mind, she simply thought she was dating. In practice, she ended up picking only guys who would fuck her over. At school, she got a reputation for being easy. So, she stopped dating guys from school and started meeting guys who were a little older. These men invariably had girlfriends or wives at home, so she had no choice but to suck their cocks in cars or darkened movie theaters.

She started drinking. Soon she started drinking a lot.

Ten years later, Hailey went to rehab.

In a few weeks, she finished the in-patient portion of treatment and began looking for work. Her counselor made her wear business casual attire and drag herself from interview to interview. She was a good-looking woman, but she had no marketable skills and felt like a fraud in her capri pants and loose-fitting blouse. She arrived at a big liberal cause company and waited in the lobby.

She didn't know it, but this was the company where the man from the hotel worked. He rounded the front desk, hand extended. He was older, grayer.

She recognized him immediately.

He took her fingers in his hand the same as he did in the hotel. His hands were still big, soft. Dry. They went to his office, a big elaborate room with dark wood, bookshelves, couches, and tables. He didn't recognize her but seemed to understand that something was wrong. He went on about the program for underprivileged women just out of treatment that his company sponsored. He seated her in the chair opposite his desk. He went around the desk, but before he sat, he looked at her intensely.

"Do we know one another?" he asked, tilting his head.

She blushed.

"Hailey?"

She lowered her head.

No one said anything for a few seconds.

She rose, stammering an apology. She wasn't clear what she'd done that required an apology, but still, she said it. "I should go," she said, halfhearted.

He gestured for her to sit.

He crossed the room, opened the door, and said something to someone outside. Closing the door, he invited her to visit with him on a couch. Framed photos sat on his desk. Hailey saw a picture of a blonde woman her age, kids on her lap.

His daughter.

He offered Hailey a drink, then realized his mistake and quickly apologized. He sat next to her on the couch. He exhaled. "I can't hire you for obvious reasons."

Hailey fixed her eyes on the picture across the room. A sour taste rose in her mouth.

"Did you fuck her?" she asked.

His brows rose and he straightened his back.

Hailey crossed the room and took the photo from his desk. She wanted to hurt him. "Did you fuck your daughter?"

"I didn't," he said cheerfully.

He reached out, gesturing for the photo.

She gave him the frame, glaring.

He placed the photo face down on the end table and sighed. Sitting back, he opened his fly and fished out his cock. He was fully erect.

Hailey felt her mouth dry up.

He smiled at her amiably. "I'd like you to get over here and use your mouth to suck my dick."

She started sobbing. Softly at first, but then her sobs grew in intensity. She didn't want him to see her cry, so she looked away. But then a big heaving sob made her shoulders shudder.

He called out to her, his voice obliging and gentle.

When she looked up, he had his hand out. When she put her hand in his, he tugged her next to him on the couch. He scolded her for acting like a baby.

He took her neck in his hand, guiding her head into his lap.

The heat from his prick warmed her face. He held her head and rubbed his cock against her lips. A satisfying tingle rose between her legs. She would not have been a good cashier or hostess. She would not have enjoyed filing records or doing whatever jobs girls just out of treatment were supposed to do. He let her head go and shoved his pants off his hips. She sniveled, waiting for him to get his pants down. Taking his balls in hand, she sank her mouth over his cock. It was familiar work. She would need about five or ten minutes. Twenty tops. It was a given that he would finish in her mouth. He understood this, so did she.

Afterward, she sat on the couch, composing herself.

He fixed his pants, went to his computer, then tapped at the keys for a bit. He called her over, grinning. The video from her night in the hotel room was playing on his screen.

The man wrapped his arm around her hip. They watched together.

It was shocking at first for Hailey to see herself so young. Her baby face twisted with lust, trying to look sophisticated. A forbidden heat moistened her brow. He showed her more pictures, photos the whore had taken of Hailey in a schoolgirl outfit.

He said that her new job would be recruiting girls to satisfy his needs.

Hailey snorted.

She only halfway remembered those schoolgirl pictures. She hadn't thought about her friend the whore in a long time. Whenever Hailey thought about that time, she could only remember certain things. How stupid she'd always felt, how mysterious the whore was. A lot of the stuff her mind had redacted was now lost forever.

She believed the whore was the coolest, wildest friend she'd ever known.

The man stood, sidling close.

He whispered that this was an opportunity she was uniquely suited for. He said she would know how to turn a girl out because she'd been turned out.

Hailey knew he was right. Looking into his eyes, she grinned. For the first time in a long time, she felt confidant. It felt good to finally find a place for herself when for so long there had been none. She toyed with the idea of finding some stupid little slut that didn't matter much and then turning that sweet little thing out.

A deliciously dirty warmth rose between Hailey's legs.

HuckPilgrim
HuckPilgrim
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