The Challenge
“I don’t want him to have a point,” Dean said.
She smiled sadly, her mouth quivering. “We’re a pair, aren’t we? You’ve got someone you’re not sure you want, I have someone who doesn’t seem to want me.”
To her chagrin, because Dean didn’t want to be the reason Katie cried, her tears spilled over her lower lids and traced their way down her face.
“Hey,” he said. “Don’t, okay?”
He swiped the tear with the pad of his thumb and Katie shuddered, turning her face to press her mouth to his palm, holding his hand close to her face for a moment before looking up at him with still-sad eyes. A lot of women had cried on Dean’s shoulder over the years, but Katie never had. Looking at her now, all he could think was how good a friend she’d always been, and how much he didn’t want her to be unhappy.
She murmured against his mouth when he kissed her but made no protest. Her mouth opened. She tasted sweet, the way she had the other day. His hand went naturally around the back of her neck to cup it, her hair a soft, thick weight on his fingers. Somehow she ended up on his lap, straddling him, their kisses turning from soft and slow to hard and demanding.
She’d tricked him before, with the blindfold, but he didn’t need it this time. His mind put together the taste and smell of her with the memory of pleasure, and his cock responded. He pulled her closer, kissed her deeper, put a hand on the small of her back to grind her down a little harder against his dick.
“Dean,” she murmured into his mouth, but his kiss stopped her.
Dean favored men close to his size and build. Compared to that, Katie was so much smaller and softer, he had no trouble putting his hands under her ass and lifting her. She let out a small, strangled gasp but didn’t stop kissing him. Their tongues twisted, tangling, and fuck, it felt good. Really good.
He didn’t try to make it to the stairs, much less up them. Her rug was soft and thick and deep, and he laid her down on it, settling between her thighs as he closed his eyes and sank into the sensations. The semi-desperate surge of pleasure coiling in his gut surprised him, making him think his cock really did have a mind of its own.
Somehow she got him undressed, a feat he could only admire since they never stopped kissing and he was fumble-fingered about her clothes. In her bra and panties beneath him, Katie laughed softly as he tried to figure out how to unhook her bra and got it off herself.
“You really never have done this,” she said.
“Of course not.” Dean slid his hands up her sides but stopped just below her breasts to look into her eyes. “Did you think otherwise?”
She got up on her elbows to look at him. “I guess maybe I thought I wasn’t that special.”
“Shut your fucking mouth,” Dean told her before kissing her again and saying against her lips, “you’re special.”
She laughed again into his kiss, and that was better than her tears had been. She lay back with him between her legs. Her hand found his dick and stroked it from half-hard to fully erect, and Dean shuddered at how good it felt. When she stroked her fingertips over his balls, he drew in a breath, holding it for a moment, before opening his eyes to look at her.
“Oh no,” he said. “The challenge was to get you off.”
“Sweetie, seeing you enjoy yourself goes a long way toward that.”
Dean couldn’t argue with that, since he was a fan of such tactics himself, but he shook his head. “I’m going to make you forget anyone else tonight, Katie. I promised.”
“Already done,” she breathed, eyes gleaming, and ran her hands up over his thighs. “Touch me.”
He slid his hands up her sides again to cup her breasts. Her nipples tightened against his palms and she drew her lower lip between her teeth. She liked that, he thought, trying to imagine what a woman would like. The same things as a guy, probably if only he could figure out the right parts to focus on. If only he could find them, he thought as Katie parted her legs a little and arched her back.
Fuck, this might be harder than he’d thought.
He bent his mouth to a nipple, sucking gently. Not flat like a man’s, Katie’s nipple peaked and grew as he stroked it with his tongue. And wow, she bucked her hips up against his belly. Dean did the other nipple, too, until both of them were rosy red and hard.
Dean had seen plenty of hetero porn–his college roommate had been addicted to the stuff, leaving skin mags around and playing a nonstop collection of VHS tapes he rented from the video store. It had all seemed sort of vague and mysterious, unlike gay porn in which everyone had erections and came in great, spurting jets of jizz, on camera. Katie wasn’t acting like a woman in a porn video. Aside from the lack of Lucite platform shoes, she was squirming only a little when he touched her.
Kissing her, though, was getting better and hotter. She pulled him to her mouth, her soft body wriggling under his. She was an amazing kisser, knowing when to pull back and when to suck his tongue just hard enough to get him moaning.
She shifted against his cock, hard on her belly, and ran a hand down his bare chest to tweak one of his nipples before pushing her panties down and wriggling until she got them off. She lay back, naked, her gaze bold but her chin lifted a little.
Dean wasn’t stupid. “You’re beautiful,” he assured her.
She raised a brow.
He kissed her, hands stroking over her sides and hips, over her belly, then up again to cup her breasts so he could use his mouth on her nipples again. “You are.”
“That feels good,” Katie murmured, laying back onto the rug and running her hands through his hair.
It wasn’t going to give her an orgasm, he knew that much. Dean might not like pussy, but he wasn’t ignorant about anatomy. All those hours of trying to study while porn ran in the background might pay off now–at least he had an inkling of where to find her clit, something his college roommate never seemed to have managed if the sounds his girlfriends made in their bunk after lights out were any indication.
He rolled onto his side, kissing her mouth again, as his hand slid down her soft belly and through the tangle of curls covering her pussy. His fingers stroked down. This was utterly foreign, completely unexpected…and absolutely erotic for all that. She was soft and hot and wet, and when he found a small, hard bud with his fingertips, she cried out.
Bingo.
Katie opened her eyes. “Right there. That’s good.”
She put her hand on his wrist, shifting him a little, slowing his pace, but letting go as soon as he adjusted. Fascinated, Dean watched her sink back against the rug, her cheeks flushing as she closed her eyes. She bit her lower lip again before breathing in, lips parted.
This was so unlike anything he’d ever done. Cocks came in a lot of sizes, but they were all big enough to grip. To stroke. Beneath his fingertips was the one small spot he had to keep his attention on. This was the real challenge, and Dean wasn’t going to fuck it up.
His cock ached, his balls heavy, as he stroked her, but he didn’t move to do anything about it. He couldn’t afford to lose track of what he was doing. Female orgasms, to his knowledge, could be tenuous and easily lost.
They kissed forever, and he didn’t care. The longer they went, the better it got. He found a rhythm that turned out not to be so different than what he was used to, and the way Katie reacted–moaning softly, rocking her hips, he thought she was enjoying it.
She stiffened, her hand going to his wrist again, her mouth open beneath his but no longer kissing. “Oh…”
Dean paused, fearing he’d somehow done something wrong. “Katie?”
“Oh, god, so close,” she whispered, and looked at him. “Just…slow down a little. Make it last.”
Dean grinned, slowing his circling finger. “Like this?”
Her eyelids fluttered. “Oh, god…”
The sound of pleasure suffusing her voice sent a throb from the root of his cock all the way through it. She moved against his hand. The flush on her cheeks had spread down her throat, across her breas
ts, and without thinking too much about it, Dean bent to suck gently at her nipple again.
Katie cried out, something wordless and ecstatic. The feeling of her moving, the sound of her–fuck–the smell of her arousal sent slickness oozing from the head of his prick. His balls tightened. When she kissed him, he felt her clit pulse under his fingertips. She moaned into his mouth.
“Fuck me,” Katie said, not like a command but more like a plea.
He wanted to, but there was the matter of logistics. Katie blinked again, her gaze clearing for a minute, and she pushed at him to roll him off her as she reached into the drawer of her end table to pull out a box of condoms. Just as she’d figured out how to get them both naked before he could, now she pushed him to sit up as she opened the box, tore open the package and sheathed him in latex before he could do more than shift his hips. Straddling him, her thighs gripping his, Katie put her hands on his shoulders. His cock rubbed at her belly and then lower as she looked at him.
“You sure about this, sweetie?”
“Did you come yet?” Dean asked, voice hoarse at the pressure of her cunt pushing his cock against his stomach. Her ass was smooth under his palms.
Katie smiled and reached between them to grip his dick at the base. She bit her lower lip, looking down, as she shifted and then…oh, fuck.
“Oh, fuck,” Dean said aloud. “You’re so hot. And tight.”
Blinking, surprised, he let the pleasure wash over him as she sank onto his cock all the way. She was tight, and hot, and slick, too. Her cunt gripped him better than any fist ever had, and he had to breathe out, slowly, to keep himself from shooting off like a kid with his first strokebook.
Katie pressed her forehead to his shoulder for a second. “Oh. God.”
He’d never fucked in this position before, but it didn’t take him more than a second to figure out how to shift and thrust upward. His cock slid inside her without effort, and she bit down, hard, on his shoulder. Dean had never been one for painplay but that was too fucking much. His cock throbbed and he made a low, grinding noise.
“Yes,” Katie breathed into his ear. “Fuck me. Just like that.”
Soft, low, distinctly feminine, her voice was in no way like a man’s. Her body, soft and curved, not like a man’s. Nothing about this was like anything he’d ever even fantasized about, but Dean discovered it didn’t fucking matter, not then, not with her cunt wrapped around his cock like that. Not with her tongue licking at the sore spot her teeth had left. Not with her moving on him, riding him. Fucking him as pleasure built and built and built.
“Touch me,” Katie said into his ear. She took his hand, slid it between them, pressed his thumb to her clit. “Oh, yes. Right there. Like that, just like that…oh, god, Dean. Yes!”
Until this point, everything he’d promised her had been all talk. Until he felt her shudder and heard the soft sighing gasp of her breath as orgasm swept over her, Dean hadn’t really been sure he could make her come. But now Katie rocked against him and his own climax shuddered through him. Perfect timing.
She blinked rapidly and looked at him, then laughed. “Wow. Well, I guess I’d say you won. Very well done, sir.”
Dean blew out a breath, fingers tightening on her hips as his breathing slowed. “Saying I told you so would make me sort of an asshole, wouldn’t it?”
Katie kissed him lightly on the cheek and eased herself off him, stretching as she reached to snag up her panties and T-shirt. “Sort of.”
He watched as she got dressed without appearing to be the least bit embarrassed. He admired that about her. Not that he was embarrassed, exactly. Just more like wondering what the hell he’d just done.
Katie looked over her shoulder at him as she pulled on her clothes, then frowned. “You all right?”
Dean nodded, sitting there on the floor with a condom on his getting-limp dick, after having fucked one of his best friends. A woman, at that. It wasn’t his most shining moment.
But Katie, still frowning, crouched next to him and pulled over a small garbage can and handed him a box of tissues, then his clothes. “I didn’t think you’d be the one to get all emo, afterwards.”
“I’m not emo.” Dean frowned and took care of cleaning up, then pulled on his briefs and jeans.
Katie studied him. “Uh-huh.”
“I’m not.”
She smiled and stood on tiptoe to kiss his cheek again. “We fucked, Dean. And it was good. For me, anyway, and I’m pretty sure you enjoyed it. It doesn’t make you straight. Just…open-minded.”
Her smile urged his, even though none of this was as gratifying as he’d expected it to be. He’d thought it would feel like a conquest. Instead, he found himself hoping Jacob would forgive him.
“Damn it,” he said, suddenly miserable. “Remind me that I like sort of being an asshole?”
“Why? Are you going to say you told me so?”
“No. Not about that.”
She knew him too well, Katie did. “Ah. It’s him, huh?”
“Jacob.”
“Him has a name?” She looked impressed. “Wow, Dean. Wow.”
“Fuck.” He sank onto the couch and cradled his head in his hands. “Fuck, Katie, what did I just do?”
“Hey.” She sat beside him and took his hand, linking their fingers. “Seriously, you’re going to give me a complex, here. What happened…do you really think it was all just that stupid challenge? I mean, I know you don’t do pussy as a general rule, but…maybe that’s why you did it. Not why you suggested it, sweetie–that was all your huge ego. But…maybe it’s why you actually went through with it.”
He wasn’t getting it, and she could tell.
“What I mean is, being with him scares you. I know why. But being with me isn’t scary. Right?”
“No. Of course not.”
She smiled. “Because you and I both know that no matter how stellar that living room rug fuck just was, and it was pretty delicious, it’s not going to lead to anything. Right?”
He gave her a cautious nod. “Well…right.”
“And for me,” Katie said, “I really just needed someone who was into me. Even if only for an hour.”
“I’m into you for longer than that,” Dean told her and squeezed her hand.
She laughed, sounding better than she had earlier, which made Dean feel better.
“You know what I mean.”
“Yeah. I do.” He leaned back against the couch cushions and stared at the ceiling.
“He makes it all seem so easy.”
“It’s not how he makes it seem,” she said. “It’s how he makes it feel.”
Jacob made it all feel easy, too. Dean frowned as Katie’s cell phone rang, vibrating the coffee table. She looked at it and sighed, but didn’t pick it up.
“It’s Jimmy.”
“Douchebag,” Dean said and picked it up. “Hello?”
“…Katie?”
“She’s busy,” Dean told the guy.
“Oh. Um, can I leave a message?”
“No,” Dean said, and hung up.
“Dean!” Katie looked shocked, but was laughing.
Dean shrugged. “Maybe he’ll think better of jerking you around.”
“Maybe he’ll never call me again!”
“Would that be a bad thing?” Dean asked. “For real?”
Katie frowned without answering, and Dean pulled her close to hug her. They sat like that for a while without speaking. Then she sighed and pushed away from him.
“Go to him,” Katie said.
Dean nodded and stood, then handed her the cell phone. “Call him back.”
Katie almost bailed.
She’d waited until the morning to call Jimmy, not sure if she wanted to go down that road, maybe waiting to see if he’d call her first. He didn’t. She wasn’t sure how she felt about that.
It didn’t matter how she felt now, though, since she’d already called him and asked him to meet her for coffee. He’d hesitated before saying yes, a pause th
at had lasted a thousand years while she forgot to breathe. She wasn’t, in fact, sure she remembered to now when he walked through the door.
He looked too damned good, she thought. It wasn’t fair.
“Hey,” Jimmy said as he slid into the chair across from her with a cup of coffee he put on the table. He shook his shaggy hair out of his face and shrugged out of his coat. His grin was at half-wattage.
“Hi, Jimmy.” Katie had a mug of coffee in front of her, but she hadn’t even sipped it. It was cold now, but she clutched it anyway as though the porcelain would warm her hands.
“This is nice. Meeting like this. Thanks for asking me.” Jimmy sounded hesitant, uncertain. Not his usual self at all.
But what was his usual self? Did Katie even know? She had to admit she probably didn’t. Everything about Jimmy was late-night conversation, and just because she’d bared her soul to him didn’t mean he’d done the same.
“Thanks for coming. It’s nice to see you.”
They never talked like this. Even the first time he’d called her, they’d slipped into a loose back-and-forth that had only gotten easier over time. Now it was as though they’d only just met and had no reason to get to know each other better.
Jimmy’s smile amped up a notch, still far from his usual bright grin, but noticeable. “Yeah. Two times in one week, that’s some kind of crazy, huh?”
Katie had always believed honesty to be the best approach, but facing Jimmy across the tiny café table, all she could think of was how she wanted to make up some lame excuse for why she wanted to see him instead of just telling him the truth. “Yeah. Super crazy.”
Jimmy seemed to relax a little bit, his long fingers turning his cup around and around on the table. His knee nudged hers. “Sorry.”
“It’s okay.”
This was going nowhere. Katie hated it. She wanted to ask him if he liked her, or if she was just some myth, a story he liked to tell over the phone. She wanted to tell him about how she smiled at the sound of his voice. Of how she wanted more.
Jimmy glanced over her shoulder toward the counter. “I’m going to grab a refill. You want one?”