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Pleasure Through Pain

Summary:

“I want Izzy to pierce my ear,” Stede blurted out one morning while he and Edith were getting dressed for the day. “Do you think he would do that for me?”

“Yeah babe, I know he would,” Edith replied, glancing at Stede in the mirror she was hunched over to apply her eyeliner. “He did all mine ya know.”

(part of a series, but its not necessary to read them in order if you don't feel like it)

Notes:

Here's some more, just like I promised. Again, thank you for reading!!!

Work Text:

“I want Izzy to pierce my ear,” Stede blurted out one morning while he and Edith were getting dressed for the day. “Do you think he would do that for me?”

“Yeah babe, I know he would,” Edith replied, glancing at Stede in the mirror she was hunched over to apply her eyeliner. “He did all mine ya know.”

“Yes of course, I know that,” Stede confirmed, they tried to say it casually, but failed. When Edith turned, she found Stede staring out the window while anxiously tapping their fingers on the window sill. “I want it to be a special… thing for us…” Stede muttered.

“Aww babe,” Edith cooed. “We can definitely make that happen.”

“Are you sure? I know he enjoys receiving pain in the way I’m thinking, but what if he doesn’t want to give-”

Edith cut off Stede’s rambling when she placed her hands over his, when their eyes met, she could see just how much this meant to him. There was a deep blush on his face and his eyes were wide and vulnerable, the expression revealing just what he meant by ‘special’.

“He’ll love it, I’m certain,” Edith assured with a smile.

~~~~~~~~

Later that night, Ed and Stede had the cabin lit with candles and incense was burning on a side table, filling the room with a soft smell of frankincense. All the piercing tools were laid out on the table, the chair Stede usually sat in was pulled out and ready.

The man was absolutely vibrating with anticipation, it had been an easy day on the ship and Izzy was in a good mood; some horrid voice in the back of Stede’s mind was terrified of ruining that. When Izzy entered their cabin, he found Stede standing stiffly by the table, Edith draped over the back of Stede’s chair. When he noticed the piercing tools on the table, his brain took off in a billion different directions.

“What’s all this?” Izzy asked with a flirtatious smirk. “You two got plans for me?”

“Well uh… sort of,” Stede stammered. “I, uh, have a request to make of you… but if you don’t want to take part, I completely understand and- well it wouldn’t have to be sexual if you didn’t want it to be…”

“Stede wants you to pierce their ear while you sit on their cock,” Ed explained, cutting Stede off from rambling himself in circles. Edith would be the guiding partner in the trio tonight, caring for her lovers and making sure everyone was comfortable and getting the pleasure and pain they desired.

“Is that so?” Izzy mused, his sultry voice making Stede’s blush deepen and spread all the way to the tips of his ears. “Do you require my services in that way, Captain?”

Oh and he did, he needed the weight of Izzy on his lap and the heat of his cunt around his cock. He needed the sharp pain that the piercing would bring. He needed, he needed, he needed…

“Israel, I would love nothing more than to have you warm my cock while you mark me in such a way,” is what Stede meant to say, but they hadn’t quite gained their footing here yet. What they actually said made both Edith and Izzy chuckle fondly and a brilliant burn of vulnerability go straight to Stede’s hardening cock. “Please Israel, I need it more than I can say, I want you to mark me as yours. Please love, I need you to do this for me- to me…”

“Captain,” Izzy addressed when Stede trailed off, his embarrassment clear. “It is my duty to serve you, and if these are your orders, I will happily comply.”

Izzy made his way in front of Stede, the captain’s confidence growing with each step his first mate took towards him, as soon as he was within grabbing range, Stede pulled him in for a deep, passionate kiss. With gentle guiding hands, Stede spun them around and lifted Izzy so that he was sitting on the table, his legs spread to allow his captain to step closer.

“Edith darling,” Stede called, only pulling far enough away from Izzy’s mouth to get the words out. “Will you come help me undress our first mate? I know how much you enjoy this bit.”

Edith was beside her lovers in an instant, deft fingers beginning to undo the straps of Izzy’s prosthetic so that Stede could pull it free and set it aside. Izzy was already wet, had been since Ed blurted out Stede’s desire, but the feeling of both of his captains’ hands on his made him absolutely gush. Conversely to Stede’s confidence returning, Izzy’s suave facade melted away as soon as he was given an order. He was never more content while at sea than when he could please his captains and feel their hands on him.

Edith’s callused fingers dragged delicately across Izzy’s stomach under his shirt causing him to gasp into Stede’s mouth. The captain stepped away for a moment to set aside Izzy’s prosthetic, Edith took this chance to scooch herself up onto the table to sit behind her beloved first mate.

Piece by piece, she handed Izzy’s clothes to Stede, who in turn carefully folded them and set them aside. Edith kissed along Izzy’s shoulder as she waited for Stede to finish unlacing the fall of Izzy’s pants. Her hands roamed further than her lips and the fingers of her right hand slipped under his glove, the scarred skin beneath was soft and sensitive and the feeling made a shiver run down his spine.

When Stede was finished untying Izzy’s trousers, they tapped him on the hip as a cue to lift himself up. He leaned back against Edith for extra leverage, the hand not currently caressing under his glove wrapped around his waist, her hand gripping his tit.

“Captains,” Izzy moaned.

“Almost ready darling,” Stede assured. “I want this to be special for both of us. Can you be patient for me, Israel?”

“Yes sir,” Izzy promised, though at this point he was clinging to the shreds of his composure, the promise of the activities to come making him desperate to move things along.

“Good boy Iz,” Edith praised, her breath tickling the shell of his ear and reminded him of all the piercings she had put there. Just to be a tease, Edith pinched one of the barbells she had put in Izzy’s nipples, his hips jolted up in response.

“Yes, quite,” Stede agreed with a little huff of a laugh. Finally, finally, they pressed their fingers against his cunt and dragged them in a line from his hole all the way up to his clit. Izzy had to hold himself back from whining, the tempting fuzz of subspace beginning to creep into his brain.

“Now, Israel, I want you to cum at least once before you pierce me, I won’t have you being all jumpy with a needle anywhere near my neck,” Stede explained nonchalantly.

“Smart,” Edith mused. She had pulled Izzy’s glove free now and had their fingers intertwined skin to skin.

“Thank you sweetheart,” Stede said with a smile. He leaned around Izzy’s head to give Edith a quick kiss, his fingers never ceased their petting motion against his cunt.

“You’ve got this all planned out don’t you?” Izzy teased, though his tone was soft and his voice was breathy with arousal.

“Of course I do,” Stede scoffed as if it was the most obvious thing in the world. “I’ve been thinking about this for a very long time now. I know exactly how I wish this to go and it’s your duty as my loyal first mate to help me realize this vision.”

Before Izzy could even think of an ‘aye captain’ or even a ‘yes sir’, Stede sunk his middle and ring fingers deep into Izzy’s cunt. Stede brought their other hand down to rest on his pelvic bone, their thumb and forefinger reaching down to rub at his cock. As Stede set his pace, Edith continued to pinch and pull at Izzy’s nipple piercings.

“Quick as you can Iz,” she whispered against his ear. “You don’t wanna leave your Captain waiting.”

“Mm, fuck, yes ma’am,” Izzy whined, he was beginning to float.

The sensations given to him by his captains’ fingers pumped and pulled him rapidly towards his orgasm, the only thing his brain could comprehend was the pleasure.

“Ca-ah-ha, captains!” Izzy pleaded. “Please.”

“Go ahead my sweet pup,” Stede granted. “Whenever you’re ready.”

Izzy was already so close to the edge that when Stede shoved a third finger in his hole, a wave of white hot pleasure rolled over him. His moans flowed freely as he came, legs flexing tight around Stede’s waist and he threw his head back to rest on Edith’s shoulder.

“There you go Israel, what a good boy you are for me,” Stede praised, his hands slowed to a stop and pulled away. Izzy laid bonelessly against Edith’s chest, her hands had transitioned to petting lovingly up and down his arms. Stede stepped away to start undressing himself and Izzy suddenly remembered the larger goal of the evening. The thought went straight to his cock and made his cunt clench.

“Shall we continue with the plan?” Stede checked in, the tenderness of the gesture made Izzy’s heart swell and the hand his captain laid on his hip brought him back into his body a bit.

“Lead the way Captain,” Izzy confirmed.

Stede obliged, taking Izzy by the hands and pulling him upright so he could stand in front of Stede's chair as the captain got settled. Izzy hadn’t noticed Edith moving behind him, but as soon as Stede was seated, she was there ready to help him lower into his captain’s lap and onto their cock.

The stretch of Stede’s cock was delicious as ever, the extra wetness from Izzy’s recent orgasm made it an easy slide. Izzy groaned deep in his chest as he sank down, the captain underneath him letting out a matching moan.

“There you go,” Edith singsonged when Izzy was sitting completely down. “Ready?”

“Aye Captain,” Izzy breathed, Stede just nodded, their eyes never leaving Izzy’s face.

“Wonderful,” Ed mused.

As she stepped away to do the final preparations for the piercing, a little bratty part of Izzy’s brain awoke and jumped at the chance to tease his captain a bit. He rolled his hips, trying his best to make it seem as if he was simply settling down, and not just trying to rile Stede further.

“Israel,” Stede growled in warning. “Don’t forget your place dear, just because you are piercing me this evening does not mean you hold the power here.”

“Yes Captain,” Izzy confirmed, he wasn’t done yet though and after a moment or two clenched hard around their cock. Stede’s hand immediately flew up to grip Izzy’s throat, not squeezing, just resting there as a reminder of the captain’s power.

“Israel,” he snapped. “Behave yourself.”

“Do I need to intervene?” Edith checked in, her tone was humorous, but she was ready if need be.

“No thank you sweetheart,” Stede replied, not letting go of Izzy’s throat. “Our darling Izzy just needed a bit of a reminder of who’s in charge, but surely our sweet little pup is ready to be a good boy again.”

Izzy nodded quickly, teasing was always fun for a bit, but as usual, it was a fleeting moment. “Yessir,” he whined, the grip around his throat tightened before releasing entirely.

The two captains smiled at their first mate, he was slipping back down into subspace, perfect. He was incredibly sweet while in that headspace, wanting nothing more than to be close and care for his captains, so eager to follow orders.

“Alright Iz, here you go,” Edith said and handed Izzy the clean piercing needle. “Ready Stede?”

“Entirely,” Stede smiled, his eyes shining bright with anticipation.

“Good,” Edith praised. “They're all your Iz.”

Izzy held the needle in his scarred hand, his touch was gentle when he tilted Stede’s head to the side. His gaze locked on to the needle and Izzy felt the cock inside him jolt, pressing lightly against his spot for a moment.

He smiled sweetly down at Stede and nodded once before pushing the needle through their earlobe. The two men moaned in unison, the sharp pain Stede felt was blending with the warm, safe feeling of having their cock buried in their first mate’s cunt. Their cock twitched again and all the muscles in his lower body were tense, they felt high with arousal and adrenaline.

“Izzy,” Stede moaned. “Hurts so good pup, you’re doing such a good job, making me feel so good.”

The first mate whined at the praise, his cunt clenching tight around his captain’s cock. In his focus, he hadn’t noticed Edith moving until she was right up next to him, her hand on his shoulder. She held out her other hand, waiting patiently as Izzy took the gold earring from her grasp. Slowly, Izzy pulled the needle from Stede’s earlobe and carefully guided the earring into place, handing the needle off to Edith to be set aside again, Stede moaned and twitched his way through the whole process.

“Well, Edith dear,” Stede addressed, his voice was ragged, obviously a breath away from losing control and fucking into Izzy’s cunt. “How did our pup do?”

Neither man looked at her as they waited for an answer. Edith leaned in close to Stede’s opposite ear, her hair fell over her shoulder and tickled the sensitive skin of his neck.

In her sultriest whisper, she simply said, “Lovely.”

Stede’s resolve snapped and he began lifting Izzy halfway up his cock before slamming him back down, the sudden change in pace and intensity had Izzy crying out and digging his fingers into the captain’s shoulders. Stede could feel their new piercing throbbing in his ear, or maybe that was Izzy’s fingers on their shoulders, or was it Izzy’s cunt pulsing around him? Suddenly overcome by the need to be closer, Stede stood, lifting Izzy along with him and setting him down on the table. The new angle allowed Stede to push in even deeper, but it wasn’t enough, they needed more.

Izzy let out a desperate whine when Stede lifted his good leg up to rest over their shoulder, their cock now hammering into his g-spot. Stede thrusted in time to the throbbing pain in his ear, lost in the intense pleasure it brought him. Leaning down, Stede pressed their mouths together in a graceless kiss, all tongues and teeth and shared moans; it was perfect. Stede’s hands traveled around Izzy’s body, rubbing his hands up and down his sides before coming up to rest on his tits. Their grip was tight and the newly formed calluses on his palms dragged roughly over the piercings there.

Edith, who had not strayed further than a step or two away, perched on the edge of the table. Her thigh pressed against Izzy’s side and she brought one hand up to rest on Stede’s bicep, a grounding touch for both of them. Once she settled, she began to hike up her skirt, her cock sat hard and neglected under the soft fabric.

When Stede pulled away from Izzy’s mouth to breathe, the two men turned their gaze to Edith. She was beautiful, her hair pulled out of her face and her bodice was unclasped in the front revealing the tattoos across her soft tits. She smiled slyly when she caught them staring, they were both so close to the edge and she knew exactly how to get them there.

“You two are such a vision,” she crooned. “Such good boys for making each other feel so nice. Especially you Iz, you did a wonderful job on your captain.”
The praise sent Izzy (who was deep in subspace now) crashing into his second orgasm, his cunt clenched impossibly tight and his nails dug hard enough into Stede’s shoulders to draw blood. The extra sting of pain blended together with the spasming of Izzy’s cunt and brought Stede to his own climax like the crest of a wave.

The captain collapsed on top of his first mate, letting the man’s leg fall from his shoulder on his way down. Both of them laid there panting, listening to the sound of each others’ breathing and the sound of Edith’s soft moans as she brought herself off from where she sat next to the pair.

Izzy tried to shift Stede’s weight off of him, but the motion made his cock rub against their pelvic bone and the sting of overstimulation made him freeze. Stede heaved himself up with a chuckle, gently pulling out before letting himself fall back into their chair, leaving Izzy splayed out on the table in front of them. Edith slipped away in search of warm rags to clean herself and her exhausted partners.

With delicate hands, Stede reached out and took hold of Izzy’s ankle and guided him so that his food rested atop their thigh. He hummed in contentment as Stede began massaging his calf.

“Thank you for doing this for me darling,” Stede said, just loud enough for Izzy to hear.

“It was my pleasure captain,” Izzy slurred. His voice was breathy and higher pitched than normal, his speech was almost sluggish as it came out. Stede hummed lovingly in response, lifting Izzy’s leg again, this time to place a kiss to the inside of his ankle.

Edith returned just then, her skirt back in place and two damp washcloths in her hands. She took a moment to press a kiss to the top of Stede’s head before turning to clean up the mess left between Izzy’s thighs. The first mate whined and tried to shift away as the cloth dragged up his oversensitive cunt.

“Sorry love,” Edith cooed, moving her hand away to wipe his inner thighs. She gave him a sweet kiss when she finished, one of her hands brushed the hair away from his face causing him to shiver.

When she turned back towards Stede, she found him lounging back in his chair, eyes half closed as he watched. A lazy smile was at home on their face, their hand still resting on Izzy’s ankle. Edith first took care of the nail marks on Stede’s shoulders, gingerly wiping away the specs of blood before doing the same to his ear.

“It does look quite dashing, babe,” Edith complimented. She folded the cloth over on itself before bending to clean off Stede’s now soft cock.

“Mmm… thank you sweetheart,” Stede moaned with a smile.

“Alright boys,” Edith addressed playfully. “You two ready for bed or do you want to eat first?”

“I can’t fucking move, so whatever you decide, someone’s gonna have to carry me,” Izzy piped up from where he was still sprawled on the table, he was slowly but surely coming back into his body and out of the clouds.

“I vote both,” Stede declared. “There’s no harm in taking the tray to bed with us.”

“Perfect,” Edith explained, this was clearly the outcome she was hoping for. “You two get settled, I’ll go get us some provisions.”

When she returned from the galley with a tray full of food however, she found Stede and Izzy curled around each other under the bedclothes, sound asleep. She chuckled quietly and her heart swelled with fondness. While trying to make the smallest amount of noise possible, Edith set the tray on the bedside table before climbing under the covers next to her lovers so that Stede’s back was to her chest and the man was sandwiched between his co-captian and their first mate.

Edith would wake her men up in a little while so they could eat and rehydrate, but for now though, they could sleep and she could bask in the comfort provided by her slumbering lovers.