Mr. Sterling's Dilemma Pt. 02

"You can take my shirt off," she said, wiggling her fingers in the air as she waited for him to follow her instructions. She couldn't have been clearer.

"Ah," Mr. Sterling said, grinning and tugging her powder blue high school t-shirt over her head. She resisted the urge to cross her arms over her chest as he dragged his warm, heavy-lidded gaze over her rosy torso.

She wasn't all that insecure, and she hadn't really been since middle school, but it wasn't every day that a man was closely examining her body like this. She was nowhere near fat and had been relatively confident in that fact since she was 14, but she was certainly bustier than average, and her belly wasn't exactly flat. Mr. Sterling didn't seem too concerned about this, though.

"Look at these fucking tits," he said fondly, cupping each of her breasts in his hands. His hands were huge--and extremely appealing in her opinion--but even he couldn't quite fit one of her breasts in his palm. This fact seemed to delight him, however, as he ducked his head to mouth at her nipple through her bra. "All mine, huh, sweet girl? How many people have seen you like this?"

Even though he knew the answer, Janie supplied him the "Only you" that he was looking for. It was true, and it was unbelievably hot that this man, this perfect man crafted from her fantasies, would be that concerned about her sexual history. The thought of being his was one of the warmest sensations she'd ever felt, and she'd missed it in the long six months of its absence.

"Damn fucking straight," he grunted, pulling the cups of the bra down under her tits to bare them. He kissed all across her chest, drawing sighs and smiles from her, and she curled her fingers in his hair, stroking the soft locks between her fingers. The rush of fondness she felt for him sharpened back into desire once he drew her left nipple into his mouth.

"God," she breathed, tipping her head back and tightening her grip on his hair. She held him close to her as he licked and sucked before switching promptly to her other breast.

"It is so fucking hot in here," Mr. Sterling mumbled when he pulled away for a second. Janie hummed in agreement and flashed a coquettish smile at him.

"Why don't you take your clothes off?"

She was kind of kidding because she'd never seen him naked and wasn't sure that he would even want that, but to her surprise, he stood right up, unbuttoned his shirt, and tossed it onto the floor with hers. Her jaw dropped, but he wasn't done. Next to go were his pants, and then finally his plaid boxers. Janie sat there topless, feeling silly and completely overwhelmed with desire as she let herself stare at the man in front of her.

Mr. Sterling was utterly gorgeous. She'd known that even when he had clothes on--it was impossible to truly hide such a strong and broad frame--but it was even more apparent now. He didn't have an eight-pack or anything absurd like that, but he was firm from head to toe, and seemed to be made up of more muscles than she thought a human being could possess. He was easily twice her size, and so sturdy and masculine that her knees would probably buckle if she weren't sitting.

He was hairier than she expected, too, with a relatively thick matting of dark hair all over him, but especially on his chest, arms, and legs. In contrast to her own body, he was so overtly male. Her stomach tightened as her gaze dropped to the most male part of him--it was huge. Well, she didn't really have much to compare him to, but it certainly seemed proportionate to the rest of him, and he was not a small man.

Clearing her throat, she lifted her eyes to his face. He seemed oddly wary, like he wasn't sure how she would react. This confused her since he was evidently the perfect man.

"You look kind of like a werewolf," is what she opted to say in an attempt to reassure him. He choked out a laugh, and she rushed to clarify, "I think werewolves are extremely hot, Mr. Sterling!"

"Please, for the love of God, call me Richard," he managed through laughter. Janie was irritated that she'd made a sexy moment into a funny one, so she stood up and took her pants off, too.

That shut him up.

She was still wearing her underwear, so it's not like she was naked, but her bra was mostly off, and he could most definitely see the damp crotch of her blue cotton panties. He licked his lips and took a step towards her.

"How far tonight?" he asked, perfectly serious now.

Janie gazed up at him as he closed the distance between them, placing his hands on her waist. He reached up and unclipped her bra, tossing it to the clothes pile, and then drew her fully against him, skin to skin. Janie released a ragged breath at the feel of his warm, hard body against her languid softness. He was made for her.

She tipped her head back to look at him, and he put a hand on her cheek, dwarfing her face.

"I think you should fuck me," she whispered, blushing. She felt his cock twitch against her stomach, and another wave of desire rolled through her.

Sure, he might change his mind about her again in the morning and decide she was too young or too whatever, but some part of her had spent their six months of ignoring each other wishing that he had at least fucked her before he changed his mind. At least now, if he left again, she would have something more solid to remember him by.

He was still searching her face. He seemed to decide that she meant it because he eased her onto her bed and spread her legs. Tummy turning, she glanced up at the popcorn ceiling and tried to remember how to breathe again. She had kind of always pictured herself losing her virginity in her college dorm room. It was nice to know herself.

When he began kissing down her torso, hooking his thumbs in her panties as he went, she released a soft sigh and lifted her arms above her head, rolling her hips in what she hoped was an inviting fashion. She was unshaven down there, but that had been the case the last time they'd been intimate, and he'd seemed unbothered. She watched his face carefully, though, as he eased her panties down her hips and legs, baring her to him. She noted a kind of hungry satisfaction in his gaze that made her stomach twist, but there was no disgust, so she relaxed back onto the mattress.

"My pretty girl," he whispered, stroking her hips and sinking to his knees. The sight of him kneeling before her was nearly too much, and she abruptly shifted her gaze back to the ceiling. But when he pinched her thigh and said, "Eyes on me," she just gave in to the overwhelming sensation of watching her dream man love her.

He drew her legs over his shoulders and used his grip on her ass to close the distance between his mouth and her pussy. She gasped at the first touch of his lips on her, closing her thighs around his head and shoving her fist into her mouth to muffle any noises. He chuckled or spoke or something, she couldn't quite tell, but the noise he made reverberated along her sensitive little pussy and sent her arching off the mattress. This seemed to please him because he held her tighter and slid his tongue inside her. Her gasps and moans encouraged him, and all of the teasing and laughter was gone; he just held tight to her hips and ate her clean out. It had been so long since he'd been close to her, much less close to the place she wanted him most, that it was no surprise to Janie when she came in five minutes. What was a surprise was the liquid that rushed out of her and into his waiting mouth. She had squirted the last time they were together, too, so she really shouldn't have been shocked, but she never did that when she was alone, and she'd been alone for months.

The urge to apologize to him arose, but he looked so delighted to be licking her juices from his chin that she decided not to spoil his fun. When he stood up and leaned over her for a kiss, she halfheartedly turned her face away, grimacing at the thought of tasting herself, but he held her jaw in one hand and tangled his fingers in her hair with the other, forcing her into place.

When he kissed her, she thought she might come again just from the depravity of tasting herself on him and the weight of his giant body holding her down.

"So sweet," Richard said, grinning. "I can't wait until you learn to last longer, baby. I could fuck you with my tongue for hours, I swear. You're so fucking perfect for me. My sweet little slut, aren't you? Waiting for me all these months like a good girl."

Janie blushed and tried not to find his words arousing, but there was only so much she could do. She was satiated from her orgasm, but every time he spoke or looked at her, which was constantly, she felt herself get wetter and wetter.

"How sturdy is this thing?" Richard asked, heaving himself off of her and eyeing the iron bedframe warily. Janie sat up on her elbows and followed his gaze.

"Um, I don't know. Not very?"

Wordlessly, Richard lifted Janie to her feet, wrapped her throw blanket around her shoulders, and sat her back in the desk chair she'd been in earlier. She crossed her legs, feeling somewhat useless, as he moved the comforter and pillows from her bed onto the floor. Anticipation built in the pit of her stomach as she watched him lay back and roll his shoulders, testing the makeshift bed. He was still naked and hard, and his cock looked unbelievably large when he was laying down like that. It was hard to imagine that thing fitting in her, but she was desperate to find out.

"Come here, baby," Richard ordered, sitting up and opening his arms. Shedding her blanket, Janie shyly crept over to him and sank into his lap. He slid his hands over her hips and squeezed appreciatively, looking like he might eat her. He really did look like a werewolf.

When he reclined onto the pillows, Janie found herself straddling his torso. She felt another rush of dampness from her pussy, and Richard's eyes darkened. There was no way he couldn't feel that.

"Look at you, sweet girl," he cooed, running his hands over the curves of her waist and hips. She flushed and tentatively rolled her hips into him. "So fucking wet for me. I'm going to destroy you."

"Well, show, don't tell," Janie murmured, grinning down at her perfect precious man. He was absurdly handsome, and his body couldn't have felt better wedged between her legs. She thought she might die.

The feeling intensified when he used the leverage he had on her hips to begin to lift her a little. He placed her over the tip of his cock, and she held her breath, shooting him a panicked look.

"We don't have to unless you want to, honey," Richard assured her, brushing his thumbs over the swell of her hips.

Janie shook her head and resolutely began to sink onto his cock. Richard swore under his breath and kept his grip on her steady. She knew she would have bruises the next day, and the idea was oddly comforting.

"I'm just gonna sit," Janie announced, a determined set to her face. Richard nodded and clenched his jaw. Gathering her courage, Janie sunk all the way down, a sharp gasp leaving her as she went.

It hurt. He was big, and she was small, and she had been a virgin, so of course she knew it would hurt. But it really hurt. Against her will, her eyes filled with tears, and Richard swore, reaching up to cradle her face in his hands.

"I'm sorry, sweet girl. Just breathe, honey. We can sit here all night, or at least until it feels good. No rush, Janie. It'll feel better once you relax."

"Okay," Janie said quietly, curling her hands around his wrists as he continued to hold her face. She was crying, and she felt deeply embarrassed by it, but there was a niggling feeling of delight at finally having him inside her. This was what she'd been dreaming about for months, what she'd been thinking of at night with her fingers between her thighs, and she finally had him.

Sensing the change in her, Richard slid his big, rough hands from her face to her shoulders, then down to her hips and thighs. She shivered, already stimulated from the feeling of his cock wedged inside her, and he grinned.

"You're really mine now, honey," he told her, cupping her tits in his hands and fondling them. Janie gasped and shifted a little, feeling the tiny movement deep inside her. She clenched in response and felt Richard's cock twitch inside her. Another gasp, another twitch.

"Roll your hips, sweet girl," Richard instructed gently, "like you did on my thigh, remember?"

Of course she remembered. And the reminder of that afternoon in his classroom made her blush, and she felt her pussy relax around him, welcoming his intrusion finally. She followed his instruction, feeling the twinge of pain again once she moved, but she didn't stop.

It was nice, really, the pressure, the too-full feeling, the stretch of his cock inside her. She felt dizzy and completely, entirely owned by him. His jaw was tight, and it was clear he was holding back, trying to go at her pace. She thanked him silently and put her hands on his abdomen for support as she continued to rock back and forth on him, adjusting to the sensation of him inside her.

"Look at you, baby," Richard murmured, grazing her nipples with his thumbs and making her clench around him. "Fucking made for my cock, aren't you? Your tight little pussy was designed to take me, and only me, right, slut?"

Janie had never been so red in her life, and she'd never felt so good either. She thought she might die. The feeling of him was so intense that she didn't know how she was supposed to keep breathing. She was his, though, so unbearably his now.

"Yeah," she said breathlessly, barely registering what he was saying but knowing that it was true, whatever it was. She was getting tired, too, and he must have sensed it because he grasped her hips in his hands and began lifting her up and down onto his cock, filling her over and over again. Janie was making obscene noises that she'd only ever heard in porn, but it felt too good for any sort of attempt at self-control. And when she glanced down at Richard, prone on the pillows with the darkest, headiest look in his eyes, she suddenly couldn't imagine a world where this perfect moment would ever be embarrassing.

She came ten minutes into the guided riding, with a loud shriek and another gush of liquid from her pussy. She fell forward onto Richard's chest, but he grunted and flipped them over so that she lay on her back and he was between her legs once more. She realized dimly that he was still hard as he wrapped a hand around her throat and fucked her for a few more minutes--until he finally came deep inside her, with a low, throaty groan.

"Good fucking girl," he growled, slapping her on the ass. She gasped and blushed, feeling humiliated and delighted as he pulled out. She watched his face as she felt his cum seep out of her, shivering at the look of utter satisfaction in his eyes. He looked downright feral, but his gaze softened when he met her eyes.

"Mine, okay?" he said, running his hands down the length of her body once more. "No matter what, this is mine."

Janie managed something like "Mkay," but her eyelids were suddenly the heaviest objects on Earth, and she was rapidly losing the battle with sleep. She knew somewhere in the back of her mind that she should say something else to him, like "This was a mistake" or "Get out of my room" or "I love you," but that all felt too difficult.

Instead, she curled a hand around his bicep and pulled him down next to her. He came willingly, chuckling, and she wedged herself into his side and promptly fell asleep.

***

When Janie woke up the next morning, Richard was gone.

She tried not to be disappointed, but it was downright humiliating to be played by the same man twice in six months. She rolled onto her side on the makeshift floor-bed, burying her face into her elbow. She thought about crying, but really, this was what she'd expected to happen, somewhere in the back of her mind.

And even now, she didn't regret anything. She felt deliciously sore when she started to climb to her feet, so sore that her stomach tightened with arousal, and she blushed bright red alone in her room. Sure, it was a little embarrassing that she'd been fucked and ditched, but at least she'd been fucked!

She caught sight of her abandoned math assignment on her desk and groaned in exasperation. This could be her breaking point, honestly. She didn't regret what had happened, but to be blatantly used and discarded, on top of having unfinished homework--it was nearly too much.

Turning away from the offending paper, Janie found her t-shirt from the night before and tugged it over her head, followed by a pair of gray pajama pants with little lattes all over them. She was sitting at her desk, desperately plowing through the remains of her assignment, when her door creaked open.

Despite suspecting who was standing in the door, Janie reached for her pepper spray and cradled it in her hand as she twisted around in her chair to face the intruder. It was Richard, of course, and he was eyeing her with a mixture of mirth and confusion, a brown paper bag in one hand and two to-go coffee cups in the other. Before she could get too distracted marveling at the fact that he could fit two coffees in one hand, she stood up and put her pepper spray down.

He followed her lead, setting the breakfast items onto her future roommate's desk and then opening his arms tentatively. Throat dry and really on the verge of tears now, Janie shuffled across the tiny room and climbed up his body like he was a tree, until she could effectively bury her face in his neck and hold tight to him.

"Hi, honey," Richard said softly, rubbing her back with his giant hands and kissing the top of her head. "I thought you would still be sleeping."

"I thought you left," Janie announced, although she was sure it was clear what she had thought.

"Ah," he said, sighing heavily and cupping the back of her head with his hand, keeping her close. "I really fucked you up last year, huh?"

"Yeah."

"It won't happen again."

"I believe you."

He squeezed her impossibly tighter, and she relaxed her grip enough that he could finally set her down. He smoothed a hand over one of her flushed cheeks and dipped his head to kiss her. When she curled her arms around his neck and started to climb him again, he laughed into her mouth and broke the kiss, cradling her hips in his hands.

"Are you sore, baby?" he asked.

"Um, yes," Janie said consideringly, tilting her head, "but I think it's hot, so don't worry."

Laughing and letting go of her, Richard turned to the desk with the bag and the coffees and began to talk. "I saw that you have a toaster, and there was a Breuger's down on Franklin St. when I was driving in yesterday, so I thought bagels would be fun. I got everything and plain."

Janie toasted his bagel first and spread cream cheese on it for him. He kissed her wrist and stretched his back, wincing, while she prepared her own breakfast. The coffees he'd gotten were vanilla lattes. Richard said that he got both of them for her because they only had 8 oz lattes. She gave him a big huge grin, and he gave her the fondest look she'd ever seen.

He ate his bagel in maybe three bites before clambering onto her bed and groaning in relief when his back hit the stupidly expensive mattress topper there. It was four inches thick, made of cooling memory foam allegedly, and topped by her white mattress protector and plain green sheets. He looked huge laying there.

"I shouldn't have slept on that cold hard floor," he groaned, stretching his arms over his head. The hem of his t-shirt rode up, exposing a patch of hair on his taut abdomen.

"I'm glad you did," Janie said, climbing up next to him and wedging herself between his giant body and the cinderblock wall. She swung her legs over his torso and smiled happily at him. "I've always known you were old, Richard, don't be embarrassed."