Chapter Ten - Administration of Oral Sex

A/N: Thanks to Cat (holdingoutforapiratehero) for helping me jump start this chapter and as always special thanks to my betas zengoalie and kliomuse for their support/advice. Thank you to my readers that message me, write me reviews and send love for this fic. It absolutely brightens my day. If you want to ask questions and see any teasers, come follow me at my Tumblr (justren21)

Bright and early the following morning, David and Killian took to the Boston bike paths for their morning run. "How did it go last night?" David asked, pulling one leg backwards in an easy stretch. They were in their usual starting location along the Charles River with majority of the Boston running population. The river was their usual place to get in their five mile run with the added bonus of watching the Harvard crew team practicing. It was a popular place among college students to run and save their money by not buying fancy gym memberships.

Killian couldn't keep the grin off his face as he rolled his neck gently, as his muscles stretched from the light exertion. "A gentlemen never kisses and tells." He started to jog in place lightly, feeling his muscles loosening from the light exertion. A part of him hated getting up so early, but he remembered Emma trailing her hands over his body and her enthusiastic response made the early hour workouts so very worth it.

David smirked. "Since when have you been a gentleman? Maybe a gentleboy!" he said with a laugh as he jogged backwards away from Killian.

"Oy!" Killian shouted as he gave chase to David, his legs pumping to lessen the distance between them. Once he reached his friend, he allowed himself to gradually adjust his pace to match David's. They jogged in silence for awhile, each lost in their own thoughts as the sun quietly rose, streaking the sky with a variety of oranges and pinks.

Finally, David spoke again. "So, spill," his breath puffed out into a small cloud from the cool morning air, the sound of their feet pounding the worn dirt path the only other noise in their secluded run.

Killian glanced sideways at David and couldn't help the small grin that tugged at his lips briefly. "Brilliant." He dragged one hand to wipe the sweat forming at his brow as they circled the river, feet crunching on the dirt below.

David chuckled lightly and clapped Killian on the back. "So, I'm guessing you were successful in your quest then, mate?"

Images of Emma's naked body stretched out before him, her hair mussed and sweaty on her pillow as she moaned through her orgasm flashed before his mind's eye. "She was certainly… satisfied." He couldn't stop the smile that spread across his face.

"Did you go all the way? Shall I have Mary-Margaret bake you an 'I'm not a virgin anymore cake' tonight?" David asked him.

"No." Killian told him, a slight disappointment coloring his words. "We couldn't even if Emma wanted to. Neither of us had any condoms on us," Killian admitted.

David stopped up short at his words, glaring at him lightly. "Killian!" He took a moment to walk over to the nearest water fountain, taking a long drink before continuing his glare.

Killian raised an eyebrow as he stopped in front of David. "What? We didn't have sex." He dipped his head down, letting the cold water from the fountain pour over his face and neck. Running his fingers through his now damp hair, Killian shook his head, lightly spraying water drops all over before straightening back up.

"Yeah, but you gotta have condoms on you from now on buddy," David said, a frown gracing his face. "You can't get into those situations and not be protected from here on out."

"We weren't…" Killian started, but David cut him off, a hand raising in frustration.

"Yeah, maybe last night you weren't. However, there might be another time and neither of you might have the willpower to hold back. Do you wanna get her pregnant?"

Killian chewed on his lip, lost in thought, the idea of pregnancy never even really occurring to him in the mix of all this sudden heady sexual pleasure.

"By the look on your face, that answer is no," David shook his head and resumed his easy jog. "Trust me, just go, pick some up and be prepared. Come on." He started back up on the trail, while Killian followed a few steps behind him, deep in thought.

"Liam?" Killian's stressed voice easily transmitted through the thousands of miles separating the two brothers.

"Aye, I'm here little brother. What has you so worked up today? How's the darling Miss Swan?"

Killian stared at the vast array of condoms displayed before him. He had walked to the local CVS pharmacy after his classes, wanting to be certain that he was carrying a condom on him at all times. David's talk with him earlier had been insistently nagging in the corners of his mind all morning.

However, upon reaching the store, his hesitation came back in full force. He didn't know there were this many options. "I'm at the pharmacy," he said his distress palpable in every syllable.

"And?" Liam's voice was decidedly not impressed with this information. "Killian. I've got fifteen minutes and then I have a meeting. Just spit it out!"

Killian heaved a giant sigh. "Look, I'm trying to buy condoms, okay? There are all these bloody options and I don't know what to buy," he whispered into the phone harshly.

Liam's amused laughter rang so loudly from the phone, Killian had to hold it further from his ear as he frowned unhappily. "I'm glad my troubles are causing you joy, brother," he snarled as he ended the call with an angry press of his thumb.

Ten seconds later, Killian's phone rang with Liam's return call. "Untwist your knickers, Killian," Liam told him as soon as Killian answered the phone.

Killian huffed angrily in reply, eyes still roaming over the display in front of him.

"I apologize for making fun of your distress. Tell me what you see."

Killian quickly described the condom aisle to Liam, pointing out the various brands, special sayings on each box. "I don't know what the difference between any of these things!" He looked up and noticed the additional selection of sex lube available from KY to Astroglide. Killian felt his old fears at his inexperience coming back with a vengeance, how was anyone supposed to navigate this?

"Well, I haven't seen the size of your cock since you were in diapers, brother. Do you need extra small or extra large condoms?" Liam teased him bluntly, his voice still dripping with amusement at Killian's predicament.

"I have no sodding clue! It's not like I wander about the States and compare my dick to other blokes! What the hell are all these options about?"

"Look, just get a normal pack. You don't need anything fancy yet."

Killian reached out and grabbed a random pack off the shelves, flipping it over to carefully inspect the writing on the back. He could feel his eyes slightly glaze over at the abundance of legal jargon written in fine print. His breath left in a small huff, "I'm just going to grab whatever, I guess."

"You'll be fine, Killian. Honestly, they are all just about the same. Same look, same function," Liam counseled from the other end of the line. "I'm just pleased that you're looking to safety measures. Have you and the formidable Miss Swan discussed taking the next step in your relationship?"

"It's not a relationship at the moment, Liam," Killian admitted distractedly, as he attempted to slip out of the condom aisle unnoticed. Suddenly, he recognized a familiar mane of golden hair standing in front of him. "Fuck it all to hell, I gotta go," he whispered, hanging up on Liam before he could get another word in.

Emma turned at the sound of his unique voice and her green eyes widened in merriment as she noticed him right away. She was dressed casually in a simple grey t-shirt and running shorts that displayed her magnificent tanned legs. "Hey there, sailor," she greeted him as she walked closer, her hips swaying ever so slightly as she made her way over to him.

"Good morning, love," Killian said as he attempted to tuck the box behind the other items in his basket. He hoped he wasn't flushing completely red with embarrassment as he did so.

Emma was too fast for him as she reached out to grab his wrist, looking over the package. Her eyes flicked downwards to the box, eyeing it carefully. "Good choice Jones," she murmured, her lips curving upward.

Killian shifted his weight from one foot to another as Emma grinned at him, the awkwardness of the moment making him wish he could fall into the nearest sewer and die.

"I'm glad you're getting prepared," she murmured. "What are you up to for the rest of today?"

"I have work at the Trident this afternoon. I have the four to close shift," he replied with a small pang of regret.

Emma's bright green eyes looked up at him wistfully, wheels in her head turning thoughtfully. "Well, I'm free the whole day. Do you want to hang out until you go to work? I drove here, so at the very least I'll drive you home."

Killian's heart leapt at the chance of spending more time with Emma. Sex lessons or not, he found that he missed her presence when they were not together. "Absolutely, I would be delighted to, Swan."

After they bought their various items, Emma was secretly pleased that Killian was already thinking ahead to the inevitable. He kept surprising her on a daily basis with his thoughtfulness and his ability to let her lead. She had dated enough trolls to know that the qualities he showed were few and very far between.

So, why are you so reluctant to call this what it is - dating? She thought to herself as they made the walk to her yellow bug. Emma shook her head at her own question, she didn't want to deal with the flood of emotions that internal question always brought.

"All right over there?" Killian called out as they reached her car. "You look troubled, love. I've always been told that I'm an excellent listener."

Emma shook her head, her troubles were always hers and hers alone. One of the perks of growing up in the system, you had no one to lean on. "Nah, sorry about that. I'm good. You want to grab lunch on the way to your place?" She unlocked her door, got in, then leaned across the seats to open Killian's passenger side door.

"Only if we stop at Five Guys," Killian replied cheerfully, his long body gracefully slipping into the passenger seat.

Emma snorted. She was quickly learning that Killian could eat like a horse and it was a wonder that he never gained a pound. Her mind quickly leapfrogged to the sight of his trim, lean body laying in her bed and she bit her lip to stop the wave of lust sizzling through her veins. "I'm glad that you stopped and grabbed condoms today. It's probably wise to have them around," she admitted.

A red flush settled over Killian's cheeks as he scratched the back of his head. She couldn't help but grin a little at the gesture; it was her favorite nervous tell about him. "It is a bit of an adventure when you've never bought them before. I never knew there were so many different types," he admitted quietly, looking down at the bag still clasped in his hands.

The words rattled around in Emma's brain for a long moment. He was embarrassed, yet still went the extra mile because he cares about you, she realized. The gesture was so sweet that she looked over her shoulder, and then quickly signaled and maneuvered the yellow bug into a secluded location - a practically empty parking garage.

His eyebrows quirked upward as she killed the engine and looked over at him. "Change of plans here, Swan?" He opened his mouth to continue, but she cut him off as she leaned over, kissing him thoroughly. It took him only seconds to fist his hand into her long hair, his tongue darting out to tangle with hers, giving back with rivaling intensity. He held on to the bag of condoms as they kissed, clutched in his grip like a security blanket.

Emma moaned lightly, needing more of him. She broke the kiss, grabbing the bag of condoms from his hand, and tossed them over her shoulder as she climbed over the center console. The look on his face was priceless as she slipped into his lap, thighs wrapping around his waist as she straddled him.

"Yes," he breathed, reaching up, instantly threading his hand through her hair again as he pulled her lips down to his. Emma hissed lightly as she leaned fully against him, feeling the insistent press of his erection against her, sending a shiver of lust down her spine. She rolled her hips against him as they kissed, creating delicious friction that made her head spin.

Feeling him pressed so tightly against her made her head spin.

They continued to kiss and grind against each other, quickly losing themselves in the moment. She felt the warm pads of his fingers suddenly graze the skin of her stomach before starting to travel upward, sweeping over her rib cage before cupping her breast. "Gods Emma," he moaned giving her a gentle squeeze as his thumb brushed over her straining nipple. "Uh… are you okay with this?"

"Yes," she moaned, her lips sweeping around to his neck. She licked a long stripe to his earlobe, tugging the flesh in between her teeth before caressing it with her tongue as Killian buckled his hips below her in response.

"Bloody hell. That feels fucking amazing."

The act of wrapping her lips around his earlobe made her grin wickedly, there was something else she had been meaning to wrap her lips around. Maybe, right now was the perfect opportunity. Emma felt another shiver of lust wrap around her, there was something so sexy about blowing his mind every time she touched him.

Among other things.

Emma was so busy mentally planning her next move that she failed to noticed Killian was still pulling up her shirt to expose her breasts to him. She helped and pulled the shirt over her head. "Ah, now that's more like it," he sighed quietly to himself before his long fingers tugged down her bra cup and wrapped his mouth around her rosy peak.

So, so good.

She wove her hands into his dark, messy hair, pulling his mouth closer to her as her back arched in pleasure. His mouth sucked rhythmically at her, her hips grinding down on him in time with his caresses.

Suddenly, she felt his tentative hand on her upper thigh, fingers dancing lightly at the hem of her very short running shorts. The rough pads of his fingertips ran over the hem, then moved upwards towards her throbbing center. Emma felt her breath hitch in her throat, wondering if he would continue his path towards her, hoping that he would be bold enough to. His fingers swept the material of her running shorts to the side, exposing her dripping heat to him. He ran a careful touch over her lips, the slow deliberate strokes causing her to shudder and moan. Emma's breath caught in her throat as his talented fingers slipped shallowly inside of her for a brief moment.

"Is this okay? I can stop if you want," Killian breathlessly whispered as he released her nipple from his mouth.

Emma's eyes slid closed for a long moment as she rocked her hips into to his magical hands. "Back seat now," she gasped out brokenly, before tossing her body back into the driver's seat.

Questioning blue eyes burned into hers from the passenger seat before nodding briefly. "All right, Swan."

It was too tight of a fit for Killian to clamber into the back seat through the front, so he slipped out the door and nervously slid in the back of the bug, feeling Emma's eyes on him the entire time. "Well, uh… What now?" he asked, his knee bouncing up and down in the small space.

"Lie back," she told him, maneuvering her body through the seats to position herself between his legs. Emma placed one hand on his chest and carefully pushed him backwards to the seat, settling down in-between his legs. Despite the extra room, it was still an awkward fit. Killian was half propped up against the door, his long legs curled around her back for the extra space.

Her hands grasped the button of his jeans and through a bit of wiggling and arching, slipped the offending material past his hips. She could see his cock straining against the material of his dark blue boxer briefs, aching to be touched. Her hand palmed him through the material as she grinned wickedly when she noticed his eyes fluttering back in his head at her touch. "If you enjoyed that," she whispered, "then you're going to love this."

"Oh I'm sure I will," he moaned. "I love how your wanton, wicked mind works, Swan."

Emma curled her hands around the waistband of his boxer-briefs, tugging them down and allowing him to spring free. She gripped one hand around his velvet length, kept her eyes locked on his widening blue ones, and then she slowly lowered her mouth and ran her tongue over the tip.

She shivered slightly at the sound of his long moan, "Fuck!"

Unable to keep the smile off of her face, she wrapped her lips around his cock, sliding downward to take more of him in. Her tongue caressed and flicked against the sensitive underside of his tip as she bobbed her head slowly, getting used to the feel of him in her mouth.

One hand was clutched against his hip bone, anchoring herself to him while her other hand and mouth worked him over. Emma wrapped her tongue around the tip, licking off the drops of pre-cum that collected there before hollowing out her cheeks and sucking him into her mouth. Killian groaned at her actions, "Holy hell, Emma. You are divine, your mouth is amazing," he panted, his hips jerking in response to her teasing.

She grinned, enjoying his praise. It was such a turn on to bring him such pleasure, she clenched her thighs together to relieve the growing ache of her core.

After a few moments of her handiwork, Killian raised a cautious hand, tangling it in her hair as Emma sucked and licked his shaft. "May I?" She heard his careful question, his hand slightly trembling. Eyes flickering up to meet his, she winked.

He groaned, long and loud as he eased her head up and down in an easy rhythm on his cock. It sent a thrill through her body to have him take control. Emma moaned, knowing that the vibrations would drive him wild. "Damn," he moaned a second later. "I am trying to stay at a seven, you know."

"Maybe I like seeing you lose control every once and awhile, Jones," Emma whispered as she slipped free, instantly wrapping his throbbing member in her hand, stroking him languidly as she blew on the tip. She waited a moment before wrapping her mouth around him again and quickly swirling her tongue over the tip.

Killian's hips bucked up into her mouth, Emma's hand wrapped around his base preventing him from doing any damage with his thrusts. "Come for me, Killian," she whispered, sliding down around him, taking in as much as she could into her mouth. The small yellow bug was filled with the wet sounds of her mouth moving on him and his low moans.

"Oh fuck," he whispered harshly, the one simple word causing her to clench her thighs together for a blessed moment of friction. "Damn it, Emma. Your mouth, I've dreamed about it. It's fucking perfect on my cock. Don't stop, love..."

Emma moaned as she sped up her movements, her hand slipping around to cup his balls, massaging them gently.

"Yes, yes… that's it," his broken moan echoed through the car as his hips arched, forcing himself deeper into her mouth. Emma felt him throb under her tongue as he came, body tense from his orgasm.

She quietly swallowed down his seed before looking up at his eyes, pupils blown wide from his orgasm. Emma giggled as a slow lazy smile lit up his features. "Bloody hell, Swan," he swore, his hand reaching down to tangle his fingers with hers.

Emma smiled.