The Right Ind of Girl for Him

Ch 1 synopsis: Our protagonist Lindsay longs for a boy who enjoys having his ass finger fucked, but she keeps striking out. But as fate would have it, she overhears a group of ladies in the bar laughing about a pervert who actually begged for that kind of action. An awkward conversation and $20 later, she gets his number.

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Tom trudged towards the cafe, muttering to himself. His internal conflict continued to rage.

Better than likely this was some cruel prank. Or she'd be hideous. Or a psycho. Maybe she worked on a new spinoff reality show called 'how to catch a pervert.' Maybe she'd be some extreme fetishist and ask him to wear a dog collar out of the restaurant.

But every time this line of thinking made him pause and start to turn back, the alternative explanation pled its case. Maybe this is real. Maybe karma has finally come around to settle up. In any case, he'd eventually return to the same conclusion: he had little to lose and everything to gain. And then he'd continue walking towards the cafe where he'd agreed to meet her.

It had been an odd phone call, to say the least:

"Umm hello, is this Tom?"

"Yes..."

"Ah great. I'm Lindsay. I got your number from Megan."

"..."

Lindsay continued, "Sorry to call you out of the blue, but you see, I got to talking with her about your past relationship, and it sounded like you and I might really hit it off."

Tom felt a sinking feeling in his stomach, followed quickly by fresh anger at being kicked when he was already down. He took a deep breath and then slowly let his rage drip into the phone, "Listen...Megan and her cronies, you can go fuck yourselves. I don't appreciate...you should find something better to do with your time than making mean-spirited prank phone calls."

Lindsay was taken aback. This was not how this was supposed to go at all. She was fucking this up. She tried again, "I don't even really know Megan, I just heard about you from her and thought we could-"

Tom decided he was tired of hearing this girl try to bullshit her way into saving her prank. He was winning this one, and he wasn't about to be duped by some improvised backtracked story. "You bitches are all the same. You don't give a shit about other people's feelings. You just-"

"QUIET!!" Lindsay screamed. "Be...quiet," she seethed. Now she was angry, partly at him, partly at herself, mostly at how this phone call that she'd pinned so much of her hopes on was quickly turning to dog shit. She quickly decided to go with a more direct approach.

"I...want...to go...on a date...with you. I don't give a fuck about Megan, or prank phone calls, or any other shit. I am calling you because I think we might be particularly compatible. Do...you...under...stand?!"

Tom was confused now. She sounded really pissed. "Um...okay..."

"Say that you understand," she snapped.

Tom gulped. "I understand."

"Do you know the cafe at 5th and Main?"

"Yes."

"Can you meet there tomorrow at noon?"

"Um...I think so."

"Good. I'll be wearing a pink baseball cap. See you then."

And then she had hung up. He removed the receiver from his ear and stared at it for a few moments. What had just happened?

Tom was still unsure what was happening as he approached the cafe.

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Lindsay sat down at the table at about 11:30. She'd chosen one facing the door so that she could surveil each diner as they entered.

She still had no idea what Tom looked like, whether he was tall or short, skinny or fat, or really anything about him. All she knew was his name and that he reportedly liked to have his asshole played with. Some basis for a date, she thought. Maybe she was crazy. But she reassured herself that many dates were based on less.

She wondered if he would show up. And if he did, how should she play it. Should this be just sex or the possibility of a relationship? Should she let their roles develop organically or if she should be explicit from the beginning that she wanted to be the dominant one in their relationship? She felt her heart pounding, sweating slightly. She hadn't been this nervous in a long time.

Best to keep expectations low, she decided. She pictured a somewhat unfortunate looking man, overweight and slightly disheveled. She would not expect that they would have a relationship, or even that they'd be able to keep much of a conversation going. This would just be a learning experience for her, hopefully a sexually enjoyable one. She would take control, finger his horny butthole, and maybe have him lick her pussy. This was a believable scenario that she could clearly visualize in her mind. Her game plan decided, Lindsay felt herself settle down as she continued to review each new person who entered the restaurant.

There weren't too many single males coming in. A balding man with glasses who might be 40 walked in and looked around the restaurant. A moment of indecision struck her. Megan wouldn't have given that guy a blow job, right? She was considering trying to discreetly remove her baseball cap when the man chose a table at the other end of the restaurant. Phew!

Just then, a boy walked into the cafe and paused to look around. He was tall, maybe 6 feet, skinny, verging on gangly, but still with some visible muscle. Dark, curly hair rested atop an attractive face, which presently wore a look of concentration as it scanned the tables. His eyes roamed from left to right before locking onto hers.

Oh. There it was again, her heart rate spiking, her throat felt tight. Could this be Tom? Too much to hope for?

They held eye contact for a few seconds, staring each other down, searching for some kind of confirmation. Then, she felt a little smile involuntarily start to grow across her lips. His expression briefly registered shock, and then her smile infected him, and he felt himself grinning like an idiot as he slowly walked over to her.

He stopped a few feet away from her. She made no move to stand up, just kept smirking at him, holding his eye contact.

"Um...hi. Are you Lindsay?" he asked hopefully.

"Have a seat, Tom," she said with more confidence than she felt.

He took the chair across from her. They sat there a bit longer, smiling at each other, enjoying the moment before risking ruining it by saying the wrong thing.

"I'm glad you came," Lindsay offered.

"Me too," replied Tom. It was cheesy and simple, but it worked.

The rest of the meal passed uneventfully. The conversation flowed without effort. They quickly traded the basic small talk information, what they did for a living, where they were from, etc. More dangerous territory including past relationships, sexual preferences, and any mention of the queen bitch Megan was avoided.

But there was a bit of an elephant in the room. Towards the end of the meal, it was Tom who broached it.

"So you said when you talked to um...Megan...that you thought we'd hit it off. Uh..was it anything in particular?" he inquired a little nervously.

Lindsay regarded him across the table in silence for a few moments with the same smirk and intense eye contact she'd had when he'd first approached the table. She saw he was a little uncomfortable. Vulnerable. He squirmed slightly in his seat as he awaited her reply. She felt giddy. This is what she had come for.

She turned to the window, gesturing vaguely with her head. "Let's take a walk in the park there, and I'll tell you exactly why I called you." Lindsay broke into a wide smile as she said this, and Tom felt warm as he felt himself smiling and blushing. He was quite sure that he'd never met anyone quite like Lindsay. Of course he would follow her across the street to the park. He would have followed her anywhere.

They crossed the street and started down the path between two wide strips of freshly cut grass. Lindsay walked next to him, a half step ahead, choosing their route. It was warm out, and there were only a few other people in the park. The air felt charged with electricity in the way only a first date can cause.

As they strolled, she looked over at him and took his hand in hers, watching his face for any hesitation. Their palms were sweaty. He swallowed his saliva and looked away, but didn't let go of her hand. He was somewhat surprised to feel his dick go rock hard in his pants. As they walked along in silence, he wondered if she could see his erection. He tried to subtly adjust his posture to make it less obvious.

Lindsay for her part was having the time of her life. This boy seemed to be exactly what she wanted. She'd never been the one to take a boy's hand, to initiate contact, to set the pace. It seemed like a small thing, but it made her feel in control. It made her feel alive. And Tom seemed to be eating it up. She'd noticed the sizable bulge in his crotch that had appeared when she took his hand. He seemed to be embarrassed about it, flushing and looking away. It made her wet. She wanted to fuck him right there.

Lindsay pulled him off the path towards a shady oak tree. She tugged on his arm, spinning him around between the tree trunk and herself. She took a step towards him, their bodies almost touching. But it wasn't quite right. She'd imagined pressing him up against the tree and taking the first kiss from him. But he was taller than her, and pulling his face down to hers wasn't the geometry she wanted for this moment.

She paused and looked around. There was a picnic table on the other side of the tree.

She looked back at him. He looked like a deer in the headlights. Unsure what was happening and why she hadn't closed the distance between them. Poor boy.

"Come sit over here," she said as she pulled him over to the picnic table. He started to enter the table's bench, but she said, "No, face out, face me." Now he was sitting on the table's bench, facing her as she stood before him. She smiled and slowly moved towards him. She slid her right leg between his, straddling his right leg but still standing up.

Tom looked nervous as hell. He looked down as her leg moved up his thigh, brushing firmly against his obvious erection, before pressing against his crotch, her right leg now simultaneously touching both of his. She put her hand on his face and raised it back to look up at her again.

Her heart rate was jacked, but her hand was steady. Lindsay felt fully and deeply that this is where she was meant to be. She forced herself to enjoy the moment, to enjoy the unguarded expression on his face, to listen to their breathing, more rapid than it should have been at rest.

"You wanted to know why I thought we would hit it off?" she asked him.

Fully entranced in her eyes, he nodded slowly.

"I'm a dominant woman," she said out loud for the first time in her life. She smiled even bigger as she confessed to him in a whisper, "I get really horny. Do you know what really makes me wet?"

His mouth fell open slightly in shock. He seemed unable to respond.

"You've been a good boy, Tom, so I'll tell you. My pussy gets really wet when a man spreads his legs for me and lets me finger his asshole."

And with that she smashed her lips into his, taking their first kiss. She thrust her tongue into his mouth and he moaned into her. He tried to push his tongue into her mouth, but she broke the kiss and said "suck on my tongue" before attacking his mouth again.

She crawled on top of him, fully straddling his right thigh now, dry humping him as they made out. She pressed her chest into his as he reached his long arms around her, embracing her, holding on for dear life. He pulled back from their kissing to gulp a breath of oxygen and then tried to kiss her neck. She ran her hand up the back of his head, gripped his hair tightly and pulled his head back before shoving her tongue past his lips again.

She was so turned on, she wondered if she had soaked through her panties under her skirt. She could feel his erection throbbing in his pants against her right leg. Suddenly, he moaned hard into her mouth and his grip around her tightened, crushing her into a desperate hug.

She pulled back and looked down at him in wonder, an unspoken question in her eyes. His face was red and it looked like he had tears forming in his eyes as he looked away sheepishly.

"Did you come, Tom?" she asked incredulously and slightly playfully.

His head started nodding as he brought his eye contact back to hers, "Yeah." He searched her face now to see if he had blown it.

She laughed and threw her hands around his head, pulling his face into her chest. "Oh Tom, that's perfect. That's so perfect," she squealed as she rocked back and forth on him a few times.

Lindsay dismounted and sat next to Tom on the bench. As they both sat there panting and catching their breath, she looked over at the wet stain on the right side of Tom's crotch. She chuckled as she finally remembered that they were in a public park and looked around to see if anyone had observed them. A couple were walking their dog at the far end of the park. The man did not seem to have noticed them, but the woman seemed to be giving Lindsay a dirty look.

Lindsay took off her jacket and laid it over Tom's lap to cover him up. She smiled over at Tom and he gave a little smile back.

"So you want to buy me dinner tonight, Tom?" she recommended.

He looked over a her, now grinning openly and said "Yes. Yes I do."

"Good. I'll pick you up at 7. Text me your address. You can give me my jacket back then."

She leaned over and gave him a long, deep kiss. Then she stood up, turned, and walked away without looking back, with the most satisfied, devious smile of her life carved into her face.