Trying Something New is a series of smutty stories I've been working on in which a post-Neverland Killian and Emma fall for each other and find various ways to explore their relationship. Lots of sex, role playing, and a few mushy moments here and there. But essentially smut.

Disclaimer: I own nothing from Once Upon a Time, though I really do think Hook and Emma make a sexy pair. Just sayin'.

3

Trying Something New: Movie Night

(Killian decides just watching porn isn't enough. He wants Emma to make some with him. There will be at least one more chapter to this. Masturbation, oral sex, exhibitionism)

He had tried to be good, but the days Killian lounged around the apartment while Emma was at work could be boring. Having amassed a veritable fortune via his many years of piracy, he had no need to work. He'd tried to convince Emma that she could quit her job too, but being the sheriff gave her a sense of purpose and though she'd never admit it out loud, he knew she secretly liked it. So, late in the afternoon after spending 3 lonely days fixating on just where she'd hidden that dirty movie and wondering what else she had squirreled away, he decided to take action.

He knew it came from her closet somewhere, and started to carefully pick his way through the small space's contents, finding everything from scarves to old Tshirts to a particularly mesmerizing pair of tall black pumps, but nothing else like the movie for quite a while. Then he discovered a box towards the very back under a pile of sweaters, and the pirate knew he'd hit the jackpot.

Pulling the box out and laying it on the bed, he began to explore its contents. Here was that dirty movie, along with 3 others that looked equally intriguing, and one that was called "Pirates" that he had to set aside. He found a book," 101 amazing sex positions," in which there were photographs of people having sex in all sorts of creative ways. Though he was pretty confident of his prowess in bed, even he had to admit that some of these positions would never have occurred to him, and he set the book aside for further study. There was another book of "erotic fiction" which sounded worth reading too. There were ties, blindfolds, and other restraints, which given how often she'd tied him up was hardly surprising. He found a small machine, something that looked kind of like a camera but bigger. He tried pressing buttons on it, but couldn't get it to work, so he decided to ask about it later. Another camera was stuffed in the box as well, something called a Polaroid, along with a few pictures of a much younger Emma posing in all sorts of suggestive ways and wearing a black bra and panty set that didn't exactly leave much to the imagination, seeing as how it was completely sheer. Those made their way into his coat, to be tucked away in his cabin with his most prized treasures. There were a few other machines too, different brightly colored wands that vibrated when he pushed buttons on the base. Some had a slightly odd shape, but there was one fairly large, pink, clearly phallic item that nearly rivaled his own cock. He had a pretty good idea of what that was, and what she used it for. He knew she'd be embarrassed and irritated with him when she realized he'd found it, but began to wonder how often she'd needed to use it since they'd began having sex several times a day. Was his Swan so insatiable?

He knew she'd be home soon, but Killian wanted Emma to catch him in the act, just so she could show him how all of this worked. So he arranged the more interesting items on the bed- the vibrating machines, the device he couldn't operate, a second movie. Then he laid down next to them, opening his leather pants for more comfort, and began flipping through the position manual.

When Emma arrived home, the place was unusually quiet- no TV, nothing cooking on the stove. "Killian?" She called, assuming he was in one if the other rooms. "Bedroom!" She heard him yell back down to her, and hanging up her coat she poured herself a glass of wine and headed upstairs to see what he was up to.

"Oh god I've created a monster," she dead panned when she saw him. "You couldn't resist, could you?" The mischievous glint in his eyes was all too obvious.

"I was bored, and knew there was treasure buried somewhere. How could I NOT go looking for it?"

"Pirate, right," she reminded herself. Ugh, Christmas was going to be impossible- he'd find every present as soon as she bought it.

She surveyed the items he had on the bed, then picked the box up off the floor and rummaged through it, mumbling," I assume those pictures are yours now, huh?"

"That was fine art, lass. Bloody priceless."

She rolled her eyes, even if his earnest expression did make her chuckle a bit. "Ok, so why do you have a video camera, the "pirates" DVD, and my vibrators on the bed?" Planning on making your own smut film?" She asked sarcastically, then grimaced when his whole face lit up. "Oh, no, no Killian..." She protested, realizing she just gave him what he thought was the best idea ever.

"I had wanted you to show me how these work, but I like your idea even better, lass," he purred, getting off the bed to pull her body against his, letting her feel his arousal through the leather.

"Really? You can't figure out what this is used for?" she responded, holding up the large pink cock-shaped vibrator.

"I know what it's for," he whispered, his breath hot against her ear as he began running his hands under her blouse and popping the button on her jeans. "I was hoping that you would show me. And, you do technically owe me for your night with Captain Hook, seeing that you obviously have a thing for pirates" he motioned towards the DVD with his head, "I wouldn't be surprised if you needed that favor again one day."

She wanted to hate him, but he was right. That DVD had been a total fantasy of hers back when she'd bought it, and though she'd been sore the next morning, that night of kinky role play had been more than worth it.

"Alright, alright. Let me get changed and set up the camera. And if you let anyone watch this, I WILL kill you."

He pulled her into him, kissing her deeply and working his hand into her pants to rub her sensitive bundle of nerves through her underwear. "Only me, love. I'm much too greedy to share the sight of you coming undone with anyone else."

A few minutes later, she was lying on the bed in a black garter belt and stockings, as he requested. She wondered how much she must love this amazing man, and how she had allowed herself to trust him enough to do something like this. After adjusting the angle on the camera to give him the perfect view of her whole body, he stripped off his clothes and sat next to her on the bed. "Ok, love, so I want you to start with your fingers, and then work up to fucking yourself with the mechanical cock. After you come, I'll ravish you properly, so make sure you're ready." He kissed her again, then made his way down her neck and throat, licking, nipping, and sucking at the tender skin until she moaned for him.

Getting off the bed, he turned on the camera with the remote, and she started by sucking on her fingers before trailing her hands down her body to her breasts, kneading and pinching until her pink nipples were hard. She worked her fingers lower, spreading herself open with one hand and slowly working the fingers on the other over her clit, drawing the wetness from her already moist slit up for lubrication. She looked at him, taking in hid heavy-lidded stare as he watched her, his own hand wandering down to his cock and beginning to stroke it. He nodded and licked his lips, urging her to continue. She locked eyes with the camera, licking her own lips as she stoked the flame of her arousal. She felt his hungry eyes on her the whole time, which only made her wetter, much to her embarrassment. As she started to get close, breathy gasps and moans escaping her lips, she turned on the vibrator and ran it over her pussy, across her clit, and up over her nipples before lining it up with her dripping cunt and slowly working it inside her. She let out a long moan as it stretched her, fucking the toy in and out slowly and deeply. She heard Killian whisper, "fuck" under his breath, feeling proud that she was getting him equally worked up with her actions. She started taking the cock deeper, allowing the little clit stimulation petals towards the base to tease and tickle her with each thrust. "Oh god, yeeees" she moaned, getting closer as she pumped her hips in time with the toy, spreading her legs wide to offer him and the camera full view of every movement. Her toes curled as she arched her back, vibrations rubbing her g-spot with each rapid thrust. With a few more pumps of the pink toy in and out, she exploded, panting and gasping as she struggled to maintain eye contact with the camera. She slowly slid the toy in and out a few times, drawing out the waves of pleasure before slipping it back out and turning it off.

"I'm feeling awfully lonely over here," she teased, again fondling her breasts and teasing her nipples until they ached. "And I'm so ready for you. You could just slip right in." That's a girl, Emma, she thought to herself. Give him a show he'll never forget.

Looking over at Killian, she could see just how much he'd been holding back, his jaw clenched and his cock rigid. He grabbed the camera and made his way over to her, attempting to crawl on top but pausing when she reversed their positions so he was lying on the bed while she moved between his legs. "I'm thinking you might want to record this, too," she purred before licking her tongue over the head of his swollen cock. He moaned, and she could tell he was adjusting the camera for the perfect view.

She worked her tongue over him, then began to take him into her mouth inch by inch, paying special attention to the head before deep throating him until her nose was pressed to his belly. Her emerald eyes flicked up to the camera whenever possible, and she heard his breath hitch as he struggled to maintain his composure while she sucked him. "Mmmmm" She moaned around him, adding thrilling vibrations to the already overwhelming sensations. His hips raised and lowered of their own accord, driving him deeper as his climax approached. "Oh, fuck, Emma." He grunted, clearly getting close. Her cheeks hollowed out as her swollen lips sucked harder, and for a moment he wondered where the hell she'd learned how to give such an amazing blowjob before pushing the thought away; he really didn't want to think about that now. He slowly raised himself up, moving gently enough that she never stopped her enthusiastic movements as he stood over her, ready with the camera to capture his release. As she tasted and felt him start to go over the edge, she pulled off with a wet pop and began jerking him off as she opened wide to let him blow his load on her lips and down her throat, then greedily took his cock back into her mouth to drain every last drop.

After she'd licked him clean, he shut off the camera and sank to the bed, needing a few minutes' reprieve before starting act II. Emma slid next to him, her hand running over his muscular body as she smiled contentedly to herself. "Bloody hell, woman!" Killian gasped. "I didn't...I mean, I'd wanted... But fuck, Emma."

"Oh, so I did a good job?" She teased, lust still shining in her eyes as she continued to caress his body with her fingertips.

"Lass, you're bloody brilliant, and you know it." He wound his fingers in her hair and she leaned herself into his touch.