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Hit Me Baby One More Time

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“Sugarpie, is it too tight?”

There was a bit of shuffling about, to test if the ties would cut into the wrists, then a shake of head. “No, it’s fine.”

“Are you comfortable? Be honest.”

This time, an affirmative nod. Elaine smiled - he had to be quite eager if he held his breath for once.

“Good, I wouldn’t want to hurt you…”, she bent down to give him a little kiss on the lips, before she added with a promising smirk, “…yet.”

Guybrush beamed back at her, now all anticipation.

(She still remembered him smiling guiltily, holding his reddening cheek, after she’d landed a well-deserved punch.
“Uhm, Elaine, dear, would you maybe…”, he’d started, a bit ashamed but hopeful. Elaine hadn’t exactly been in the mood to do anything, but then he had looked up to her with a rather sheepish grin and swollen cheek.
“Do that again, please?”

Elaine had smiled in response.
“Oh, that I can do. Hold still!”)

Well, she had been angry with him back then, and for good reason. While she approved of Guybrush’s kink, she usually preferred a more reasonable and enjoyable approach without any lasting damage.
It was worse enough that Guybrush had a tendency of getting into trouble. He was lucky to have her to take care of that – to take care of him, as well as his needs. Elaine could take the responsibility for him when he was at his most vulnerable, something she wouldn’t have trusted anyone else with, least of all Guybrush himself.

Now that his wrists were tied to the bedpost, lying on his back, his legs put up and spread at a nice angle, he was ready for action, but Elaine liked to appreciate her handiwork. She had tied his ankles to a thin iron bar, which, aside from exciting Guybrush a lot, made things considerably easier since it forced him to keep his legs in place instead of wriggling about.

While she kneeded the skin of his thighs down to his ass and up again, he closed his eyes, steadying his breathing, just like she always told him to do. She softly slapped his ass with the palm of her hand, playfully, causing him to catch his breath.

"Elaine", he whined, not all serious, but seriously pleading. Guybrush never had been good with patience.

"Shhh", she told him sternly, and he quickly shut his mouth.
Finally, Elaine took pity on him and now lifted his legs, pushing his bend knees back towards his chest.
"Now, keep your legs up like that, sweetheart."

"Yes, darling", he said, eager to comply. And for the moment, he didn’t seem to have much trouble keeping his legs sort of hovering mid-air, high enough to grant her easy access to his upper thighs and ass, and he kept them up while Elaine warmed the leather of the flogger by slowly pulling the strings through her hand. She liked to make him work for it a little - the greater the anticipation, the more fun they were going to have.

The first hit always came a little unsuspected, to make him gasp. Elaine started easy on him, of course, but she did appreciate the noise too much to warn him. Other light strokes followed, in a slow, regular pattern, until his thighs were reddened and Guybrush had closed his eyes, his breathing visibly heavier.

"Honeycake, how do you feel?", she asked, kneeding his now sensitive skin again to spread the soft burning a little.

It took him only a short moment to reply. “Fine. Yes, very fine.” His voice was a bit wobbly, but as he opened his eyes to smile at her, they were already glazed with desire. Guybrush easily entered this state of submission, maybe because he offered it so readily to her. How could one not fall for a guy who was so open and also so sweet about his kinks, Elaine mused, as she kissed him on the forehead.

His smile wavered at the first sharp slap, and the second red belt on his thigh caused him to groan - first softly, then louder as the strokes came faster. Once Elaine had found her rhythm, Guybrush’s eyes were half-closed and his mouth open as he let himself go. His legs started trembling, even more so as she stopped for him to get a break, and Elaine had to steady them with one hand.

He drew a few shaky breaths before he noticed. “Don’t stop”, he said, his voice failing him half-way, so that all that came out was a whisper.

Elaine gave him a look. “Come again?”

"Please", Guybrush breathed, very ready to plead. "Please don’t stop."

Elaine cocked an eyebrow, and Guybrush put up what he thought was his convincing smile. “Pretty please with sugar on top?”

Well, how could she resist that, after all, she was only teasing him right now.
With a few hard strokes, she had him back to yelling, moaning and, finally, quivering, especially as the leather strings caught his balls. Guybrush threw his head back with a loud moan - he had to be very close now, desperately close, so Elaine put the flogger aside.

Her fingers moved over his heaving chest. He was hot beneath her fingers, his breathing was irregular now. There was sweat on his brow and a few stray locks of his hair stuck to his face. As she was about to curl her fingers around his hard-on to make him come, properly, he interrupted her.

"Elaine", he breathed, "could you be a dear, please, and… scratch my nose?"

With a slightly theatrical sigh, she moved her hand upwards again and brushed the strands of hair out of his face, before doing him the favor. “Like this?”

"Yes," he moved a little to adjust the tip of his nose under her finger, "A tiny little bit to the right - yes - right there! Thank you", he added in all honesty.

What a cute little idiot, how could she ever resist him. Luckily, she didn’t have to, and they had still business that needed to be finished. “Now shush!”, she told him with a smile, before she unceremoniously put her fingers around his dick again.

A few strokes had him gasping helplessly, and as he came with a shudder and a loud moan, Elaine rewarded him with a long, deep kiss.


Guybrush was pretty much spent after this treatment, but that was fine, he’d pay her back later by putting his tongue to good use. For now, Elaine was content with stroking his sore skin, feeling him tremble slightly and listening to his calm breathing.

She’d have freed him from his ties, but Guybrush had begged for keeping them a bit longer, so Elaine had just loosened them up a little. They both liked cuddling afterwards, especially Guybrush of course, but Elaine didn’t mind at all. He was warm and she liked holding him close, watching his relaxed expression. There was a weak smile on his face, and all Elaine saw in it was a tired state of bliss.

She raised her head to kiss him again, this time more softly.

His smiled widened as he muttered, half-asleep: “Love you, sweetie.”

"Love you too, my little honeybun."