The Crush

He couldn't remember a time when Delilah Finnigan wasn't overtly flirting with him. Perhaps sometime before she was eleven or twelve, though he wouldn't bet on it. As long as he could remember her, she was batting her eyes at him and saying extremely inappropriate things. But he was never receptive to them. He wasn't interested in having anything to do with his best friend's little sister.

Most of the time, he just ignored her, rolling his eyes and avoiding looking at her directly. There were a few times when he'd snapped at her, telling her to cut it the fuck out. Other times, when he felt especially mature and like he had his shit together, he'd try to explain to her exactly why nothing would ever happen between them.

"No, Del, I don't want you to take your top off," he explained to her calmly, as she sat on the edge of the pool in her backyard. It was the summer after he and Collin had graduated from high school and Delilah was barely fifteen. Her string bikini left very little to the imagination to begin with and now, when Collin went inside to get some drinks, she had offered to show him her boobs. "Please don't take anything off, this is really inappropriate."

"Geez, I don't get why YOU are always so appropriate. There are probably a ton of guys your age who would jump at the offer," she told him, squinting against the sun.

"That's fine and what you do with them is your business, but nothing is going to happen between you and me. This is really fucking uncomfortable! I don't see you in this kind of way, do you understand?" He tried to explain to her. She pursed her lips, placing her hands on the concrete behind herself and leaning back on them. Possibly, she was trying to push her non-existent breasts further out, but it did nothing for him. Chris never saw Del as anything sexual. She was just this girl.

He saw less of her when he went away to college and wasn't hanging out as much at the Finnigan house. And yet any time he was around, at winter break, over the summer, she was right back to the same games as always. Del was nineteen when he and Collin graduated from college and she was once again trying to seduce him at the graduation party that their parents threw for Collin.

"I think you just keep getting hotter and hotter the older you get," she told him, sipping from a bottle of Mike's Hard Lemonade that she wasn't old enough to drink yet.

"Why don't you have a boyfriend, Del?" He asked her, trying to understand why her interest seemed to lie solely in him.

"Umm," she licked her lips, sticking a hand into the back pocket of her short denim cut-offs. "Sometimes I have a boyfriend, just not at the moment. I'm not a virgin, if that's what's holding you back," she winked at him.

"No, that's not what's holding me back," he replied flatly, just as Collin approached them.

"What's holding him back is that you're like his sister from another mister," Collin delivered, laughing at his own joke. "You don't dip your pen in the family ink." Collin was probably half in the bag at that point and was the only one who cracked up at his jokes. Del rolled her eyes at her brother.

"I think you're missing out Chris," she smirked at him. "I actually know what I'm doing."

Once Collin had his own place though, there was really no reason to hang around the Finnigan family house anymore and he hadn't seen Delilah in several years. He never asked about her, though Collin sometimes volunteered information about his little sister without being asked. Besides being a relentless and unyielding flirt, Del was apparently also super smart. She had finished undergrad a year early, had her Master's Degree at 22, and quickly climbed to project manager status at the software company where she worked. All that Chris had to say about that was 'good for her.'

He didn't recognize her right away when he got the first glance of her at Collin's wedding. It's been years since he's seen her. Her honey brown hair was long and styled in loose waves, the strands from the front pinned back with a jeweled clip. She wasn't in the wedding party - Collin's fiance had a slew of sisters and cousins and friends and she had enough trouble choosing among them, without getting Collin's sisters involved too. Del wore a short, strapless cocktail dress that accentuated her breasts and narrow waist and flared out into a full skirt over her hips. Her makeup was done in that perfect 'barely there' way that made her look fresh and glowing. He only recognized her in context because she was standing with her two much older sisters, Annie and Bevin.

He watched her from afar for a bit, pondering over whether he'd actually be into Del now if she weren't so intense and overbearing. She was definitely beautiful. Her long, toned legs looked amazing in the strappy heels she wore, disappearing under her short dress. And then she spotted him and the old flirty grin was spread over her face.

"Oh my god, Chris, being all grown up totally agrees with you," she peeled away from her sisters to come closer to him. She looked up at him, placing her hands on her hips and blatantly ogling him head to toe. "Man, you just keep getting hotter. You fill out that suit as if it's been made for you." She reached a hand and smoothed it down his lapel.

"It's tailored," he replied curtly. He wore suits to work daily so it made sense to invest a bit more into them, since he was able to afford it.

"Damn," her gaze shifted down and he felt super uncomfortable for a moment until he realized she was looking at his hand, not his crotch. "How has no one snagged you up yet and gotten a ring on that finger?"

"I see you haven't really changed, Del," he stuffed his hands into his pockets. Her mouth dropped open in a mock shocked expression.

"What are you talking about?! I take offense to that! I have grown at least two cup sizes since college," she cupped her boobs in her hands, over her dress to accentuate them.

"Geez, Del," he shook his head, rolling his eyes. Obviously, he's noticed that since she had previously been entirely flat-chested, but it wasn't the kind of change he meant. Delilah has grown into a beautiful, sexy, woman, but she was still the same girl who had hit on him as a teenager and this just didn't seem appealing to him.

"Are you staying at the hotel?" She cocked her head to the side, the flirtatious look not leaving her face.

"Yep," he confirmed. The wedding was at the hotel so it made sense to stay. The smile on her face widened.

"Maybe this will be my lucky night and I'll finally seduce you," she winked at him.

He didn't know what to say to that. Collin approached them at that moment and pulled Chris away for some photos with groomsmen, which he was thankful for.

"Listen, man, you're both adults now, Del's 25, she's got her shit together, I'm not going to be offended if you want to go for it with her. Don't hold back on my account," Collin told him during some downtime before the ceremony. "If anything, you know, it could be a good thing knowing she's with you and not some asshole."

"She's not really my type," Chris stuffed his hands into his pockets. Collin gave him a look, his forehead creasing.

"How so?"

"I don't usually go for these pushy, aggressive girls. It's kind of a turn-off for me." Chris didn't want to go as far as to admit that he preferred the quiet, submissive type. He preferred to make the first move and he usually made the move on that girl who sat quietly off to the side, listening to her friends being loud and obnoxious, but not engaging herself.

"Ah, right, I can see that," Collin nodded. "I just don't think you should use me as an excuse, that this would somehow be against the bro-code or something. Like I said, she's not a kid and she could do a lot worse than you."

Chris let that affirmation sit with him, that Collin was ok with this. It changed the outlook on the situation a little bit. Yes, they were adults now and their three-year age difference wasn't as big of a deal as when Del was fifteen. Now she was an attractive, grown-up woman who was really into him. And she wasn't letting him forget how into him she was.

"Dance with me," Delilah grabbed his hand and dragged him out onto the dance floor during the reception. He went along with her, not wanting to make a scene. It was a slow song and she wrapped her hands around his neck, swaying right up against him to the music. She wasn't exceptionally short, but even with heels on, she was still looking up towards his face. Her expression was so full of lust that the air between them seemed charged. "Do you go to the gym like every day, or just five times a week, or what?"

"Four days a week," he replied, feeling pretty good about himself that Del had noticed that he was in great shape.

"Do you have any tattoos?" She bit her lip at that one, her eyes looking wide and round.

"Which answer would disappoint you more?" He smirked in response. She seemed to give it a moment of thought.

"Both are hot in different ways. If you don't have any, it's a clean-cut kind of sexy and if you do, it's a little bit more rugged sexy," she smiled. Fuck, she was starting to stir something up inside him now, being so close and saying these things.

"Do you have any tattoos?" He thought he was changing the topic away from himself, but immediately regretted it as soon as the words were out of his mouth.

"Yeah. I'd love to show them to you, Chris, but it's kind of inappropriate out here in front of all the people." She winked. And now that the seed was planted, he couldn't help but wonder exactly where she had the tattoos.

When the song ended, she took his hand into hers and pulled him out into the outdoor area. He moped along involuntarily as she seemingly looked for an area that would lend some privacy. There was a speech forming in his head, telling her off, explaining to her as gently as possible what it was that he was looking for in a woman, whether it was a random hookup or a relationship. He planned on being blunt, he felt like curing her of this weird obsession she had with him.

She found some corner obstructed by bushes and backing him up against the wall reached up to kiss him. Her lips landed on his soft and determined, pressing in, parting, her tongue flicking out to lick his lips, but Chris pulled away. His hands came up to cup her face and he held her gently away from himself.

"Del, listen, this isn't going to work for me." She looked up at him with her big, blue eyes, biting her lip. "I'm not into this whole 'take what you want' kind of thing you have going on. I'm glad that you are this confident, successful woman who knows what she wants and goes for it. That's great and good for you, but it doesn't do it for me." She narrowed her eyes at him, calculating.

"The fact that I am confident and successful is a turn-off to you?" It was possible that she was getting offended, but Chris was glad that for once it appeared like she was actually listening to what he was saying to her. It seemed he could talk to her about this, explain things to her, and that perhaps she'd understand that they just weren't compatible.

"No, that's not it. It can actually be a huge turn-on for me when a confident and successful woman who takes no shit from anyone else submits to me. That's... God, that's actually fucking hot. But Del, I'm not into getting backed into a corner like this. I prefer to be on the other side of this." He turned then, still holding onto Delilah's face, switching places with her. He just planned on putting himself in the position to exit, but there was something in her look that made him hesitate.

"I can do that," she looked serious and determined. He let go of her face and she didn't move. Her hands clasped behind her back while she continued to stare up at him. He considered her for a moment.

"I'm not sure you understand what I'm saying here," he kept his voice calm and even. "It would be completely out of character for you. I don't think that is what you'd like or that you'd get off on it."

"You're saying it would be hot if I submitted to you and allowed you to be the aggressor and initiator. And I think I can give up control like that, I think it would be interesting to try." Their eyes stayed locked in on each other. She wanted to try it his way and he found his cock straining to half-mast at the thought. He reached a hand out along Del's neck, up underneath her hair, lacing his fingers with the strands as he cupped the back of her head. This would probably work out, he thought, she'd either get completely scared off or he'd get what he wanted. Either way, this would be a good thing. He'd lay it all out there for her.

"Del, there's no talking back or flirting in this. There's quiet and obedience and maybe a little bit of pain," he tugged her hair back sharply, though not too hard, but she still sucked in a breath, drawing her bottom lip in between her teeth. But she didn't object or yell at him to stop, which served to turn him on more. "You're gonna be good with this?" She nodded, her chest rising and falling in a way that suggested a certain amount of excitement on her part. Yeah, that got him the rest of the way to hard. Time to test out how into this she really was and whether she'd bolt.

He tugged her hair again, pulling her down. Delilah sucked in another sharp breath, but went along, lowering herself down to her knees in front of him. He enjoyed the sight of her in this position, her face upturned, looking up at him expectantly. She really was a beautiful woman. Chris took his eyes off her for a moment, looking around real quick, just to make sure that they were still alone and well concealed. He widened his stance a bit, pulling his hand out from Del's hair.

"Why don't you unzip and take my cock out," she sprang right to it without hesitation. "You've been waiting to do this for years, huh," he smirked. She nodded, her face serious. She wasn't replying with anything cute or flirty. It was good to see that she understood how this worked. She stroked her hand over his hard length, looking down at his cock, then took the head into her mouth, licking and sucking it gently. His hand was back in her hair, jerking her back. She stopped, looking up at him. "Next time you're gonna wait until I tell you that you can suck it, understood?" She nodded. It looked like there was a sliver of a smile tugging at one corner of her lips and he shoved her head back onto his cock.

She was good. Her hand and her mouth worked in tandem and her tongue expertly swirled around his cock. She increased her speed, bringing him closer and closer to the edge, then backed off, circling the sensitive head of his cock with her tongue and licking the underside. He placed a hand on the wall behind her, leaning into her. Del seemed invested, as if she had something to prove, to rub his face in the fact that this is what he's been missing all this time. He didn't like this, although he absolutely loved the sensation of what she was doing to him.

"No hands," he growled the command, feeling himself reaching the point of no return. She moved her hand away from his cock and he used the hand that still grasped her hair to shove her deeper onto this cock, fucking her throat. She actually moaned at that! The vibrations sent him over the edge, with barely time to warn her with a single word "Swallow."

In the next beat, he felt his cock pulsing between her lips, sending streams of cum right down her throat while she calmly swallowed around his cock. He loosened his grip on her hair as his orgasm retreated and she inched her lips off his cock, looking up at him, as if for approval that this was ok to do. He exhaled heavily, tucking himself away and zipping his suit pants. Delilah waited on her knees, wordlessly. Her hands folded in her lap. She didn't seem scared or itching to get away from him. She was calmly playing along, her confidence still obvious, because this was something she chose to do. And he didn't hate it.

"Stand up," he instructed. She got to her feet, brushing off her knees. They were red and marked with the pattern of the grass on which she had been kneeling. She straightened up, obviously proud of herself.

Chris backed her up against the wall, his hand resting on it, blocking her in. His other hand touched her thigh, inching upwards, fingers caressing her skin. She breathed out relaxing against the solid surface behind her, not taking her eyes off him. That lust and electricity that he noticed while they danced were still in her eyes now. He leaned in and kissed her, rough and demanding, teeth scraping over her lower lip, just as his fingers reached the apex of her thighs. She moaned when his lips retreated and he felt the dampness of her panties, pressing them into her seam.

"Geez, Del, you really enjoy sucking cock, huh?" The fabric of her panties has gotten entirely soaked after a few passes of his fingers. He pushed them aside, rubbing her slick pussy unhindered by the small scrap of cloth that covered it. She whimpered at his touch. "I want you to answer my question for me."

"I really enjoyed sucking YOUR cock," she replied, her eyes closed now.

"And now you are really enjoying my fingers, huh?" He pushed two of them inside her and she let out a quiet yelp, then immediately relaxed again, letting him finger fuck her.

"Oh that's good Chris," she breathed out.

This seemed too easy somehow, like she shouldn't have just complied with his demands immediately. How far would she let him take it? She said she was interested in trying this out, but how long would she be able to go before demanding what she wanted?

"You know what else I get control over?"

"What?" Her voice was soft. She didn't open her eyes, lost in the sensation of his fingers fucking her pussy. He pulled them out sharply, making her eyes fly open.

"I decide when you get to come," he gave her a smug smile. Her eyes and nostrils flared, but she didn't say a word. He waited a moment for any other reaction, but she stayed still and quiet, glaring at him. "Open," he instructed, bringing his fingers that had just been inside her to her mouth. She complied. "Suck them clean for me, Del," he placed his fingers right on her tongue. Once again, she followed his directions without hesitation or complaint. There was just a bit of annoyance in her expression now, an obvious disappointment in not being allowed to get off too. He pulled his fingers out of her mouth, stuffing his hand in his pocket, and waited for a moment for her to say something. She said nothing and Chris felt impressed with her self-control. "I'm in room 327," he checked his watch. "Meet me up there in about an hour. And maybe I'll let you come then." He winked at her this time, before walking away.