The Right Kind of Girl for Him

"OOooowww, what are you doing?!" he'd exclaimed when she'd stuck one little finger up his ass.

As she sat at the bar alone, Lindsay recalled bitterly how her last conquest had failed the weekend before. Everything had been going well; she'd gotten him on his back with his pants off. His legs spread. His dick hard in her hands. Like with most of the men she'd fooled around with, it had been surprisingly difficult to get him in this position. When she'd first palmed his crotch as they made out, he put his hands on her shoulders and tried to guide her down to her knees. Many men, she assumed, liked to see their women kneel below them as they stood or sat to receive head.

Lindsay had found the best way to avoid that was to be direct with what she wanted while making it seem like she was catering to them: "Lay down for me, baby. I'm gonna take such good care of you. Let's get that dick out." That had done the trick. She had felt powerful and horny, standing over him fully clothed, while he lay there naked from the waist down, his stiff cock pointing up at her expectantly. She liked to savor this part, soaking up his vulnerability as she moved onto the bed between his legs.

She'd smiled down at him like a lioness stalking its prey as she took his erection into her hands and squeezed it gently. She watched his breath quicken in a little gasp, a little moan escape his lips. She moved one hand to his balls, carefully fondling his delicate parts. He liked what she was doing to him. He wanted her. She was in total control of the situation and she felt confident that she'd be playing with his asshole soon. She knew that a lot of guys felt weird about ass play, but if she could just get her finger in there, she knew he'd love it.

But as soon as she'd grazed his anus with the middle finger of her ball hand, he'd tightened up and physically moved his pelvis further up the bed. He'd said nothing, maybe hoping it had been an accident. When she tried again, he jerked away again and started to say "Um, what are...".

Not wanting the situation to unravel, she'd quickly moved her head down and taken his glans into her hot, wet mouth. That shut him up. He'd moaned again, clearly wanting more. As she lightly sucked and licked at the head of his cock, she worked up as much saliva as she could and let it leak down his shaft. She used this to wet her middle finger and then, right as she allowed another centimeter of dick into her mouth, she pushed her fingertip into his butthole up to the first knuckle.

"OOooowww, what are you doing?!" He grabbed her hand and pulled away from her.

"C'mon baby, just a little ass play. Just give it a chance. I promise you'll like it."

"I'm not gay," he barked at her as he moved to put his clothes back on.

"Of course not. This has nothing to do with being gay. I'M A WOMAN!" she pleaded with him but could see she was losing the battle. "You're leaving?!"

"You're a strange girl," he'd said. And then he was gone.

Now, as she sat at the bar nursing her 3rd drink of the night, she wondered what was wrong with her approach. Maybe she shouldn't have surprised him with it. Maybe she should have told him from the start that she wanted to finger fuck his tight little asshole. But she'd tried that approach twice before and it had also failed.

She'd had a great time with one guy in college who had squealed and came hard when she'd stuck it up his ass. She'd loved feeling his little hole rhythmically contracting on her finger in time with the contractions of his dick in her other hand. It had since become something of a fetish for her. But she'd been unable to recreate it with another guy since.

"Maybe I need to let this go and get on with my love life?" she thought to herself. But she was obsessed with the act. It made her wet to imagine herself on top of him, spreading her man's legs, controlling his orgasm perfectly, penetrating his most private, dirty place. She wanted a man who was willing to be that vulnerable for her. No, she wanted a man who longed for it the way she did. But how to find such a man...

Suddenly an eruption of female laughter came from the corner booth behind her and to her left. She looked back and saw what looked like a group of attractive women of similar age chuckling over their drinks. She turned her head to try and eavesdrop on what had been so funny.

"Dodged a bullet there, girl! That sounds like some pervert shit," one of them said.

"Yeah Megan, sounds like he's probably a closet homo," another joined in.

"Wait, wait, wait, let me get this straight, he actually begged you to fuck him with your vibrator? Like a lesbian?!"

At this point, the girl who seemed to be named Megan resumed control of the conversation, "I'm telling you girls, it was fucking weird. I'm giving a world-class blowjob, and he was like 'please play with my balls,' which I thought was a little weird, but... I did it. Then after a while I'm thinking to myself, 'when is this fucking guy going to come?' when he says 'please play with my ass.' I was like 'excuse me?"

"No one's ever asked me that, Megan. Guy was a fucking fag for sure."

"Right? He's really hot for it, trying to grind his butt towards me like a bitch in heat, 'just finger me a little or maybe a toy if you have one.' I was like 'Dude, you need to leave now.'

"So you just kicked him out right there?"

"Well yeah...after I had him eat me out! Haha!" she bragged, high-fiving her girlfriends.

"....Um...excuse me, ladies..."

The group of girls stopped and turned around to find a young woman standing awkwardly a few feet outside their booth, giving them a weak wave.

Lindsay hadn't thought this through. Her heart was pounding as she tried to think of her next move. "I'm so sorry to bother you, but I couldn't help overhearing your story and...you said you broke up with him, right?"

"I'm sorry?" Megan asked, looking incredulously at the interloping woman.

"You broke up with him? You're not dating him anymore?" Lindsay repeated hopefully.

"No. I'm finished with him," Megan said slowly, still trying to figure out what this woman's deal was.

"I see. Is there anyway you could give me his name and number?"

The girls blinked at each other for a moment.

"20 bucks" Megan finally said.

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Two weeks later, Lindsay was there, seated in the cafe, waiting for the boy to show for their blind date, hoping that her $20 was well spent.

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This is my first story attempt. Let me know if you would be interested in reading further.