It wasn’t from a peaceful sleep that Chaldea’s final Master awoke from.  The air was heavy with the scent of days old alcohol, sweat and body odor and he body felt heavy, covered in a warm mucus that stunk reminiscent of fish.  Cracking an eye open, instead of the ceiling of the dark and cluttered room he was expecting to see, he was instead staring up the crack of a round and soft looking backside with blonde locks of hair framing it from either side.  However, the rear and back her stared up at where broad and large enough to completely eclipse his entire field of vision, a few more feet forward and he’d have been buried under the plump feminine posterior, though the heavy scent of stale sweat and whiff of miasmic gas made him thankful that he wasn’t.  “What time is it?”  Unsure of how long he had been out for, Ritsuka was sure it was close to morning at least.

High above, with a playful smile on her face, the musket-wielding half of the paired summoned pirates noticed that her Master was awake and fine.  “See Mary, I told you Master would be alright.”  She chirped happily, wiggling her butt and briefly exposing the wet, puffy anus sparsely lined with thin blonde hairs hidden within.

“Hmph.  Master, you shouldn’t sleep so much then.”  The voice of the curvaceous pirate’s partner said in a terse but affectionate tone.

Tilting his head to look towards her, the silver haired girl, normally short enough to be mistaken for one of Chaldea’s children Heroic Spirits, was also towering over him as he laid flat on his back on some cushioned surface.  While harder to tell with her other half for the hair covering her back, Mary’s naked body was unashamedly displayed for the young Master to observe, and hopefully appreciate, with no attempt to hide the long, deep scars gouged into her flesh.  Most prominent was the one that ran diagonally from her right brow to left cheek between her gorgeous, azure blue eyes and the shorter, perpendicular scar on her right cheek that didn’t quite meet the bigger one.  However, catching his attention as it mostly blocked the view of the rest of her undeveloped body, was a proportionately massive cock, its foreskin peeled back and a thick, cloudy, whitish-yellow liquid oozing from the slit in it.

Breaking her gaze for the much smaller youth, she pouted at her partner.  “We’re almost out of time, Anne.”

“Oh, try not to be so hard on him, Mary.  At least Master is a real man.”  The busty blonde giggled, smiling down at Ritsuka with respect for the inept Magus evident in her crimson eyes.

“One day… that’s what the terms of the bet were.”  He thought, and from their conversation it seemed it was almost over.  But what a night it had been…

The Previous Day

Much to the envy of womanizers like Fergus or relief of those with relationship problems like Diarmuid, according to most of the female staff and Servants of Chaldea the most eligible bachelor of the organization was their only remaining Master, Ritsuka Fujimaru, hands down.  There might be Mages with better magic circuits, Demi-Gods with extraordinary physiques and kings and warriors possessing near bewitching levels of charisma, but each came with more than a few issues.  It wasn’t a matter of settling for someone less troublesome, Ritsuka, to most of the women, was just the best overall pick available.  This, however, came with no end of problems for the young Master, which only stacked higher the more Servants he summoned.  He was, after all, only human and there were only so many hours in the day.

And so, as is the case for most days he has off, Ritsuka found himself… ‘approached’ [read: cornered] by one, or in this case two, of his Servants, Anny Bonny and Mary Read in their swimsuits.  They both complained to him about not being summoned to fight in such a long time.  Unable to appease them with promises of calling on them in the future, Ritsuka was forced to accept a bet with them, win and they’d let the matter drop, lose and he would have to comply with their wish.

“Yay!  I win!”  Anne cheered, jumping up from the table.

“Good job, Anne.”  Her partner congratulated in her subdued excitement, drawn into the blonde’s chest as she hopped up and down.

Hanging his head and sighing, Ritsuka leaned back in his chair and smiled.  “I could have swore that you already played a King of Hearts though.”  He chuckled.

“Pirate rules, pirate tactics.”  The shorter girl replied, holding out a victory sign with a smug smile.

Cleaning up the cards on the table quickly so the suspicion couldn’t be confirmed, Anne giggled slightly nervously and winked at her Master.  “It’s not against the rules if there’s no proof.  Besides, Master, did you expect a clean game against outlaws like us?  Or are you trying to back out of the bet?”

“No, no.  You beat me ‘fair’ and square.”  The dark haired youth surrendered the point, shaking his head.  “So, what did you want for your prize?”  “Probably lots of skinship and light molestation like usual I bet.”

Smiling at each other, a twinkle of longing and mischief in their crimson and azure eyes, Anne Bonny and Mary Read flanked their prize on either side.  “Oh, it’s not too much, right Mary?”

“Mm.  Simple is best, Anne.”  The loli agreed.

Signaling each other as they had practiced, the two took a deep breath and said in unison, “Spend a full day with Anne Bonny and Mary Read.”  Claiming Ritsuka as their prize, the two seafaring women activated the magecraft designed by the most proficient Casters at Chaldea’s disposal to alter Ritsuka’s size, shrinking him out of his clothes.

Before the shrunken Master could even begin to fall, Anne snatched him out of the air and Mary collected his clothes before they left and headed towards their room.  Passing several of female Servants and getting looks of envy as they sensed their Master in the blonde pirate’s hand, the two made it to their room without incident.

Opening the door to their dimly lit room, the two had been warned on multiple occasions to not keep their room open if they weren’t going to clean up properly.  Rarely a more cleanly-minded Servant like Cat or Nightingale would come by to clean up for them or Kiyohime might incinerate all the trash, and furniture, but neither outlaws minded as they would just mess it up again anyway.  Half empty bottles of rum knocked over on the floor, discarded swimsuits and Mystic Codes ‘borrowed’ from other Servants scattered on the furniture.   The bed was left in a messy state, the sheet discolored from stains and grime and stiff from sweat.  With the ventilation switched off, the stale air was laced with strong booze, potent body odor and a faint whiff of sea water.  While most turned up their noses at the odor emanating from the two’s room, fellow seafarers understood and found a nostalgic comfort in the smell Anne and Mary purposely endeavored to recreate.

“Their room is as filthy as their Rider form’s.”  He thought, peeking out through Anne’s fingers as the two closed the door.

“Uhuhu… Master, do you realize how long we’ve waited for you to come visit our room.”  The busty blonde asked, opening her hand to hold Ritsuka between two fingers.  “We behaved ourselves in the past, but you’ve neglected us for so long, we can barely contain ourselves.”  Pulling the waistband of her tight jean short-shorts and black bikini bottoms out with her free hand, she licked her lips in anticipation as she positioned him over the gap.

While the atmosphere of the room was heavily laced with alcoholic fume and lingering sweat, the overwhelmingly potent odor that was trapped in Anne’s clothing almost caused Ritsuka to gap immediately, and he was still level with her chest!  He could see her sweat practically steaming up from the thick blush of golden hairs she didn’t bother to trim, carrying a strong smell of acidic ammonium with a sweet scent he couldn’t identify.  “Whoa, whoa!  Anne, hold on a second!”  Clinging to her fingers the young Master knew where the situation was headed now, the lust in the taller pirate’s eyes was almost scary.

“Yeah, not so fast, Anne.”  Mary said, catching Ritsuka’s attention and for a moment he thought there was hope!  Mary was a bit more level-headed that Anne, though she was a bit more clingy.  “You’re always flirting with Master so much.  I want to go first.”  Ritsuka didn’t like the sound of that, but when he turned to ask the silver haired pirate for help he was shocked to see her pull the crotch of her white one piece bathing suit aside to free an almost adorably small phallus!  “Hmm?  Oh, you didn’t know, Master?  Despite being recorded in history as a woman, because I pretended to be a man for so long I have one.  In fact, it’s more common than you’d think.  Captain Drake has a pretty rugged one as well.”  Blushing at the memory, Mary pulled the top of her swimsuit down to reveal her petite chest and erect, pink nipples.

“What!?  Mary, no fair!”  Anne bemoaned, handing Ritsuka to her partner with a pouting face.  “When did this happen?”

“A while ago I guess?  You weren’t there Anne, and we drank a lot.”  Explaining her night with the boisterous, charismatic, beautiful captain, Mary pressed Ritsuka into her chest and groped tightly around him, flopping down on the bed.

While among some of the smallest in Chaldea, Mary’s breasts were still incredibly soft and capable of expanding around Ritsuka’s body to a small extent.  However, the pleasantly warm and squishy sensation of the girl’s chest was overshadowed by the absolutely disgusting stench that emanated from her underarms just a short distance away!  The jiggling motion of his Servant playing with him didn’t help the nausea onset by the terrible smell and rather than focus on escaping her grasp, Ritsuka futilely tried to block it out by covering his nose.  “N-Nope… No, I can taste it!”  It was unreal how potent of a smell she could have and yet it was unnoticeable before.

“Mmm… Master, you feel so good on my nipple.”  Mewing happily, Mary continued to use her Master like a toy and rubbed him firmly into and around her hardened nipple.  While she would have preferred him at his full-size for their first time together, taking advantage of his vulnerable state excited her pirate nature in a way she didn’t realize she needed in her life.

Pouting as she watched her other half’s small member begin to grow and expand, Anne reached her limit from all the cute moans Mary was trying to suppress.  “Hey, don’t leave me out of the fun!”  Crawling on the bed over the silver haired girl, tossing her black bikini top onto the floor without a care, she dragged her breasts over the smaller girl’s slender stomach before lifting them to dangle just an inch over Mary’s.  “You might have made for a great pirate yourself back in the day, Master.  We would have run through and shot anyone before sharing each other with them.”  Giggling happily, she lowered her colossal chest, completely burying not only their Master, but Mary’s underdeveloped breasts as well.  Cupping her cutlass wielding partner’s face softly, she pulled her into a passionate kiss as they rubbed their chests together.

Trapped between the two, Ritsuka’s air was limited at best and once he had to start choking back foul tasting, salty perspiration, Chaldea’s last Master wasn’t sure if his vision was starting to blur from the lack of oxygen or the stink.  Neither Servant seemed to be bathing regularly, and together their sweat and body odor mixed to dominate his senses.  Mary’s nipples poked up into Anne’s along with the shrunken Magus’ body as he had been dragged and folded over the smaller girl’s excited nub.  Consciously knowing he was naked between two beautiful women, Ritsuka’s body reacted as a horny teen’s body would, but at his crotch was being pressed into the entrance to Mary’s swallow breast, his erection slipped into a tight opening!  “Wh-What was… Am I…?”  Unable to fully process what was happening, Ritsuka felt his butt slip into a particularly deep fold in Anne’s breast as the rough movement of the two’s love making forced him to likewise, though unwillingly, make love to the tiny opening his manhood had found.

“Ahn!  Anne, I think Master’s thing is…”  Feeling the intrusion of her Master’s member, a jolt of pleasure she had never experienced before raced from her nipple.  Gripping the blonde’s massive breast with both hands, she forced herself onto their Master until she felt a rush of Mana enter her teat cause her to have a mini-orgasm and flop back onto the bed.

Sitting up to allow Mary to catch her breath, Anne could only see a milky white liquid seeping out of the loli’s nipple with no sign of Ritsuka… that is until she felt squirming against one of her inverted nipples and giggled.  “Heehee, are you stuck Master?  Or did you want to have some fun with my boobs too?”  Bouncing her hefty breast in her hand, she couldn’t even see him over the curve of it he was so small.  “Maybe later though.  There is so much more we need to do.”

“M-More!?  Anne, wha-!?”  Not sure how much more he could take, Ritsuka could barely notice the odor of the room anymore, almost completely masked from the sweat of the two women.  However, as Anne crawled backward down Mary’s body he froze when he saw the silver haired girl’s formerly adorably small penis had grown into a monsterous cock that was reaching up towards her sternum!  “How?!”  Suddenly feeling vastly inferior to the small framed girl, even if he wasn’t small enough to literally penetrate a nipple, he’d come nowhere near Mary’s length or girth.

“I know how you feel Master.  I was surprised when Mary first showed me how big she could get, but she always was better at being a ‘man’ than the rest of our crew so it makes too much sense.”  Carefully pulling the shrunken youth from her nipple, Anne slipped him into her cleavage and used an arm to hold her breasts together while firmly grasping Mary’s girthy meat rod.  “But you have nothing to worry about.  Just try to play nice together, okay?”  Piercing the underside of her cleavage with her other half’s erection, a gap opened up under Ritsuka as she slid down its length causing him to fall deeper into her sweat-filled valley.  “Uhuhu, any pirate worth their salt knows you have to bury your treasure in a chest.  If you don’t want to fall through, grab Mary tightly, Master.”

While sweaty, because so much of the blonde musketeer’s chest is open to the air from what she normally wears, the sweat coating Anne’s breasts isn’t as bad as the other scents and odors from the other parts of her body.  It was a bit stuffier between her assets, but it was nothing compared to the dizzying stench from Mary’s erection.  Like Anne’s crotch, the musty atmosphere the behemoth was normally confined to actually impeded Ritsuka’s ability to think straight and the pressure the busty blonde was applying as she bounced up and down its length was enough to force his mouth open.  But if the foul mixture of stagnant cock sweat, slimy precum and stuffy boob sweat draining down his throat wasn’t bad enough, Ritsuka was starting to get his erection back!  “Why!?  It smells horrible and tastes so bad!”  Confused but without time to consider his state of arousal, Mary started pumping her hips in time with Anne’s bounces, causing more of her shaft and even parts of her head to grind against Ritsuka’s body.  “Come on, you two.  Time out for a second.”  During the short reprieves he got at the extreme crests and falls of the two’s efforts at the world’s most unique threesome, Ritsuka tried to pull himself free of Anne’s hold or away from Mary’s cock but inadvertently got his hands stuck in a fold of flesh at the top of the massive member!  “Time ou-!”  Jerked free of the tight embrace of Anne’s chest, the young Master’s hands were nearly crushed in the tight crevice of Mary’s foreskin and dangled from her cockhead helplessly.

“Oh my.  Mary, look at this.  I think Master likes your dick more than my boobs.”  Anne teased, feeling Ritsuka get pulled from her cleavage.  “Can’t say I’m not a little hurt.  I though all men liked big, bouncing breasts… though Master is very accepting.  Uhuhu.”

Sitting up, Mary sees their tiny Master with his hands stuck in her foreskin and giggles at the sight.  “Do you really like my cock that much Master?  Or are you just envious it’s so much bigger than you?”  Mary asked playfully, lifting up his body so he was hanging vertically over the twitching behemoth.  “Normally I only let Anne play with it, but since I love you too I guess I’ll let you play with it as much as you want.”  Pinching the edge of the protective sleeve of flesh, she smirked a bit as she pulled and made a gap.

There was a visible haze of heat and moisture that rose from the opening, accompanied by a chokingly thick wave of cum-tainted air.  Coughing from the revolting smell, Ritsuka covered his nose to attempt to block it out as tears formed in his eyes.  At the extreme edges of what he could see, clumps of what looked like slimy mashed-potatoes poking up from the darkness but they were neither sparse nor did he believe they’d be shallow seeing how high up they were reaching.  Turning white as a sheet, he met the small pirate’s gaze and shook his head.  “M-Mary!  Waaaaaaaaaaaai-!”

“Nuh-uh.”  letting her foreskin snap back after releasing her Master, Mary giggled at his barely visible on the underside of the shaft's neck.  “Hey, hey, look Anne.  Master’s getting covered in my dick’s filth.”  Thrusting her member in the blonde’s face, she triumphantly showed off the nigh imperceptible lump that was slowly evening out as the foreskin tightened over the inept Magus.

Ritsuka could have hurled at the intense, stomach-turning stench inside of Mary’s foreskin, but forced himself not to for fear of some of the squelching mush around him entering his mouth.  The temperature and consistently weren’t helping matters either, but worst of all was the fact that his nose was clogged up with the gunk!  Being short on breath before getting dropped in, his lungs were crying out for oxygen.  “No… No, no, no!”  Feeling his will slipping to his body’s need to breath, on the cusp of blacking out he opened his mouth and pockets of smegma-tainted air rushed down his throat as the fermented semen/filth mixture coated his tongue.  “I’m gonna be sick!”  Feeling his diaphragm convulse in an attempt to empty his stomach, Ritsuka gritted his teeth to stop it… involuntarily chewing the cultivated slop.  However, he couldn’t spit it out and the minuscule amount of air he got before wasn’t enough to satisfy his body’s needs.  “I can’t believe I’m doing this…”   Forcing down the mouthful of wet, pulpy gunk, tears flowing into the surrounding mess, Ritsuka opened his mouth once more.

“This little bump?”  Anne asked, pointing to where she could barely see a deformation in Mary’s foreskin.  “Maybe we made him a bit too small.”  Giggling, it was entertaining all the same.

Jerking her erection with a gasp in response to a pleasant sensation, Mary accidentally slapped the blonde in the face with it.  “Oops, sorry Anne… It’s just… Master.  H-He’s… I think he’s eating some in there.”  She explained, poking Ritsuka’s tiny body through the thick foreskin to bury him a bit more so he made more contact with her more sensitive flesh.  “He’s really… devouring it.”

“Hmmmnnnn!  Master!  I’ve been waiting for over a month of Mary’s cock pap!”  Somewhat annoyed, Anne grabbed Mary’s member and squeezed around the head to gauge how much smegma had built up.  “Well… I suppose I could share some with you, but you’re going to compensate me for my loss.”

“Ahn!  Yes, Master.  Lick me a bit, will you?  Don’t just eat…”  Spasming in place, Mary was thoroughly enjoying Ritsuka’s struggle to breathe, not that she knew the reason behind his actions.  Already a quarter of her height in length, Mary’s phallus wasn’t even at full mast yet, and the shrunken Master’s efforts were aiding in reaching her maximum erection.  “Master!  Master, Master, Master!”

Sharing her coveted ‘Mary pap’ was one thing, but Anne was starting to get jealous that she was being ignored.  “Don’t hog Mary all to yourself!”  She pouted, trapping the gigantic member with her knees and peeling the foreskin down over the head, revealing their Master, stuck in the thick globs of smegma.  “Uhuhu, you look good enough to eat, covered in Mary’s cock pap like that Master.”  Seeing the state they had put Ritsuka in, Anne couldn’t help but giggle.  Bringing the exposed cockhead directly under her nose, she inhaled deeply of it’s pungent scent and instantly felt a warmth build in her crotch, her heart flutter and mouth water.  “Mmmm, aged to perfection!”  Licking up a glob of the yellowish paste-like substance, she held it in her mouth for a bit, letting her saliva build and partially dissolve it before swallowing.  Grinning from ear-to-ear she wetted her lips.  “Thanks for the meal!”

Finally able to breathe without having to swallow a moist cocktail of semen and penis filth, Ritsuka barely registered the sight of Mary laying in sweat soaked sheets breathing heavily.  He didn’t even notice the shadow fall over him as Anne’s face approached, but the next thing he did notice as darkness.

Mary watched as Anne’s full, plump lips slowly opened and spread over the tip of her erections.  The blonde’s tongue was already prodding the opening of her cockhead as she slowly took more of the meaty member into her warm, soft mouth.  She wanted to stop her at the crest of her head, if Anne continued too much more she’d lose Ritsuka, but she was too slow as Anne slammed her mouth down as far as she could!  Arching her back in response, Mary thrusted her meat shaft into the back of her partner’s throat, causing her to gag momentarily but not pull back.  Instead, Anne grabbed Mary’s tight tush and forced more of her erection down her throat, masterfully scooping Ritsuka off the heated rod and stuffing him into her cheek for safe keeping.  Her throat expanding to accommodate the pulsing member, Anne swallowed more and more, until her nose was flush with the base of Mary’s phallus and it bottomed out in her stomach!  Mary could feel Anne’s heartbeat against her rod and was close to cumming when Anne entirely pulled out and sat on the bed next to her, her breathing barely affected.

“Anne… Master…”  Not satisfied just yet, Mary poked the blonde’s cheek with her saliva soaked member.

“Yes, yes.  I think it’s just about time we start the real fun.”  Anne agreed, smiling.  Kissing the top of the silver haired pirate’s cockhead, she deftly pushed their Master against it with her tongue and continued to apply pressure against the back of his head until she felt it slip inside.

Only barely aware of the fact he had almost ended up in the stomach of one of his Servants, Ritsuka didn’t have the strength to fight was the slithering oral muscle caressed his embarrassingly erect member for a moment before shoving him onto a slightly spongy, warm surface.  Having breathed in so many of the two’s different odors, he couldn’t even tell that a different liquid was getting mixed into the saliva all around him, but when a tight opening constricted around his face, he attempted to pull himself free.  “Ow!  Anne, Mary, this hurts a bit.”  He pleaded, but neither could hear him currently.  Instead, Anne’s tongue scooped him up and angled his body to more easily enter the nigh crushing orifice she was feeding him to.

Releasing Mary’s erection, Anne smiled seeing the tiny pair of feet protruding from the tiny leaking slit in the top of it.  Pulling down her jean-shorts and bikini bottoms, along with the rest of her outfit, and grabbing a half-spilt bottle of rum from the floor next to their bed, she took a hearty swing from and got on all fours facing away from her partner.  “Mary~... Lookie what I got for you~”  In a sing-song tone, the blonde pointed her wide rear towards the aroused loli and pulled her cheeks apart to reveal her tight, quivering anus lined lightly with some soaked, unruly hairs.

“Anne’s big butt!”  Reacting immediately, Mary’s engorged member jerked at the sight of the plump backside and juicy hole, slurping the last of their Master into her urethra with ease.

As copious amounts of precum flow past him, Ritsuka lets out a muffled, pained cry as the walls tightened around him, then he began to slip deeper into the heated tube almost as if he were falling into it.  “This.. This has to be Mary’s…”

Seeing as both her erection and Anne’s asshole were so thoroughly lubricated, Mary wasted no time plunging into her bowels.  “Anne’s butt!  So big but so tight!”  Slamming her hips against the blonde’s, Mary let the coiling walls tighten around her girth and then enjoyed the slimy secretions coat her before pulling back and thrusting as deep as she could again.

“Oh God!  It’s thicker than usual, Mary’s dick is the best!”  Mewling like a cheap whore, Anne’s arms and legs gave out as her insides were roughly violated by her partner’s massive erection.  However, she didn’t fall to the bed despite no longer supporting herself.  Suspended like a stuck pig, Mary was easily able to hold her up with her member alone, but grabbed her hips and started pumping in and out.  “Mary!  Mary, harder!  Don’t worry about me, I won’t break!”  Rubbing her sex as  it heated up, Anne found her strength again and began bucking her hips in rhythm with Mary.  As pirates, while they were afforded the luxury of gentle love with each other when they wanted, sex was typically a rough affair and they preferred it that way.  “Make me unable to walk straight!”

Tossed back and forth in Mary’s thigh urethra, Ritsuka couldn’t do anything but fight to breathe and stay conscious.  The rocking, violent motions were making him sick, but if he were given a choice between where he was and somewhere else on their bodies he reluctantly choose to be here.  “Choose to be a sex toy for two pirates…  That’s how far I’ve come.”  Self-deprecating thoughts aside, this was the most comfortable he had been all night.  Though there was one thing he wasn’t looking forward to…

“Master!  I’m going to shoot you out into Anne’s big butt soon!”  Mary snickered, slowing her pace a bit so she could enjoy the reverberations of her large, powerful thrusts.  Each one caused the blonde to moan louder than the last and watching the ripples spread though her butt cheeks was entertaining.  “Try to not get lost in there.  If you think our room is filthy…”  On the cusp of climax, the silver haired girl pulled back one last time and waited.  With this last thrust she’d spill over the edge and douse her partner’s rectum with semen and a tiny Master.  Relishing the heat emanating from the deliciously plump backside, Mary took a deep breath and rammed her hips into Anne’s as hard as she could, wrapping her arms and legs around her.  “Anne!  Master!”

Ever in sync with her silver haired counterpart, Anne was also one good thrust away from orgasm, and what a powerful one it was as her stomach deformed out in the shape of Mary’s cock.  “Ahn!  Mary, shoot Master deep, okay!”  Her bowels quickly filling from a single spurt of the immense member, her body quivered in delight and clamped down hard around the stiff rod.

Lost in the complete darkness and unbearable heat the only indication of the impending horror he was about to face was the tightening of Mary’s urethra around him and the loud moans of ecstasy.  While mildly thicker than water, the silver haired outlaw’s precum was easy to move in, but when she came it was like Ritsuka was hit by a wall of gelatin it was so thick!  He was pushed back a ‘fair’ distance, for whatever that means while trapped in a yuri futanari’s male organ, before it began to deform around him and force its way down his throat.  “I’m gonna die!”  Thinking it was the end, the shrunken Master was shot out of the tight tube into the blonde musketeer’s rectum and found it almost impossible to swim through Mary’s seed.  Breaching an air pocket he gagged on the miasmic air trapped in Anne’s bowel and watched in horror as Mary fully pulled out mid-ejaculation and the way out close behind her!  “How could it smell so bad in here?  I thought Servants didn’t have to…”

“We don’t have to,”  Anne answered, feeling a pleasant soreness from her anus as it sealed back as tightly as it could, but given how thick Mary’s seed was even a bit loose the spunk didn’t flow back out easily.  “But Mary says it feels nice.”  She couldn’t feel her legs, her entire body was numb but Mary wasn’t finished yet.

Covering her partner’s back and hair in with a couple more shots of cum, the smaller pirate flipped Anne over to finish, marking her face, breasts and stomach in her pungently fishy-smelling ejaculant.  Pulling her white one-piece bathing suit off, she quickly wiped the filth and semen from her still erect manhood.  Tossing the impromptu rag unto the floor she collapsed into the blonde’s cummy, busty embrace.  Their bed was soaked and the two slowly lapped up what was in reach of their tongues.  “Anne, how’s Master?”

“In my butt where you left him.”  She giggled in reply, wiggling her hips.  While she wasn’t able to keep Mary’s spunk from leaking out, her Servant strengthen anal muscles were too much for him to pry apart, though she did enjoy his efforts to.

Sliding down the more playful pirate’s body, Mary unhesitatingly buried her face between Anne’s legs and sucked on the sensitive, twitching anal sphincter.  The first mouthful was dense and chunky, but there wasn’t anything solid so she swallowed and tried again.  This time she felt her tiny Master squirming on her tongue.  Swallowing the mess around him, she climbed back up Anne’s body and slowly opened her mouth for the blonde to see.  “How does Master look?”  She asked telepathically.

Giggling at the sight of the handsome youth out of breath pressing himself back against Mary’s small tongue so’s to not fall out, Anne pulled her head down for a kiss and began softly stroking the still erect phallus sliding between her breasts.  “Like he could take a bit more before we take a break.”  She replied, as they enjoyed a passionate kiss between the three of them, passing Ritsuka between themselves.

Because of her increased sensitivity, Mary is much easier to bring to a second climax and feeling the smaller girl’s body tense up Anne quickly pulled their Master into her mouth.  While not as powerful or plentiful, Mary’s second batch of baby batter was enough to cover their faces and fill their mouths.  “Anne… Sleepy…”  She said, hugging her partner tight as her member began to shrink.

“Okay, okay.”  Anne cooed softly, patting Mary on the head like a spoiled child.  She was also pretty exhausted from all the fun and given the zero resistance from the man in her mouth they weren’t the only ones.  “Just let me put Master to bed, okay?”  Sitting up, she opened up a gap in Mary’s foreskin once again, it was lined with a heart layer of jizz which was perfect.  Opening her mouth, she drooled the tiny man into the fold of skin and released it.  Laying back down, she pulled Mary over her body so she could use her breast as pillows and inserted the mostly flaccid member into her womanhood.  If she concentrated she could just barely feel their Master’s tiny heartbeat.  “Rest well Master.  We’re not done just yet.”

Present

And so, with the hairy anus above him and leaking phallus below, both of which he had seen the insides of, Ritsuka could barely move and just sighed in defeat.  “Just a bit longer…”  At the very least he knew that the two were displaying their unique brand of affection towards him, so he couldn’t hate them for it.  “Could you two just be a bit gentler this time?  I feel like I almost suffocated so many times already.”

“Not going to run?”  Mary asked, bending over to look at him a bit closer, her manhood sliding forward as she did.  “You’re not angry?”

“Nope.  I promised you, right?”  He replied, smiling up to the two.  “How much longer is left?”

“Oh, Master!”  Turning to flank him on either side with her legs, her golden forest of her unmanaged bush almost touching his head, Anne smiled happily down to him.  “Heehee, well… about that…”

As she began to explain, there was a knock at the door, followed by another set of the paired Servants, Anne Bonny and Mary Read.  However, just seeing the two enter the room Ritsuka had a flash of clarity.  The Anne Bonny that walked in was wearing her brilliant, vibrant crimson coat, low-cut black one-piece bathing suit with skirt and stockings while the Mary that came in was in a white, two-piece frilly bikini!  “N-No…”

“Sorry to mislead you like that, Master.”  The Anne on the bed said, getting up and going over to stand behind her Mary, embracing her.  “But I’m the Archer Anne Bonny.”

“And I’m the Rider Mary Read.”  The nude, silver haired futanari added, standing next to her same Class partner.

“Which means, you haven’t even begun to fulfill your obligation…”  The naked blonde stated, and given how well he had taken their ‘fun’ with him last night she was starting to feel a bit guilty for tricking him now.

“What do you mean?  You said you just wanted me to spend the day with you, didn’t you?”  He asked, but seeing the lust hungry looks on the other pair of pirates he was starting to get really nervous.

“Wrong.”  Rider Mary said, also slightly conflicted now.  “We said ‘spend a full day with Anne Bonny and Mary Read’.  It was Anne’s idea.”

Sweating profusely now as the Rider Anne and Archer Mary crept closer to him in silence, he snapped his attention to Archer Anne.  “But I-”

“Sorry Master.”  She interrupted, sticking out her tongue cutesily with a playful giggle.  “This entire time you were with an Anne without Mary and a Mary without Anne.  That means you haven’t fulfilled your end of the deal… yet.”  Having come from a wealthy family with a better education, despite her air-headed mannerisms the blonde pirate was more cunning than most give her credit for.  “Next up is a night with our other halves, then a night with just Annes and a night with just Marys before we all can play together, uhuhu.”

“Let’s enjoy ourselves to the fullest, Master.”  Rider Anne said, winking at him as she took off her jacket and Archer Mary pulled her bikini bottoms aside to reveal an equally tiny, for now, phallus as her Rider counterpart.

“Anne?...”  The smaller girl asked as they each watched their other halves climb into bed with their shared Master.

“What is it Mary?”  The blonde asked gently, noticing the slight trepidation in her voice and wrapped her arms comfortingly around her.

The silver haired girl hesitated for a moment, but in the comfort of Anne’s arms asked, “... Do you think… If Master were part of our crew back then…”

She didn’t need her to specify anymore than that, and Anne tightened her embrace a bit.  “You know that would never happen.  If Master were alive back then, he’d have been a handsome and righteous privateer at worst.  Though if that were the case we could have taken him as our personal prisoner. Uhuhu.”  Just thinking of coming back from a successful raid to a delicately rugged young man was an all too appealing thought.

“Yeah… but if he was, on that day do you think…”  She knew, given his kind and goodly nature, that Ritsuka would never have been on a pirate’s ship outside of raiding it or as a prisoner, but hypothetically she still had to wonder.  That fateful day in October of 1720, on the waters of Jamaica.

It wasn’t a day either of them remembered particularly fondly.  As their cutlasses danced and flintlocks fired to drive off their attackers, the Captain and rest of the crew were hiding in the ship’s hold like dogs.  It was the day she had lost all respect for the man known as ‘Calico Jack’ and the cowards that sailed with him.  Though thinking of the scenario suggested by Mary, of a young, incorruptible boy from the Orient with hair black as the raven’s feathers and a smile so dazzling reacting to aggressors boarding their ship.  She could only picture such a reckless, brave pirate getting run through on a privateer’s cutlass or perforated by pistol and musket fire and left to bleed out on the deck.

Her heart tightened at the thought.  “Then I might have gone into the hold myself and shot each and every dog that left him to die.”  She answered, not knowing if she and Mary would have had the spirit to scream themselves hoarse if they’d have had to watch their Master die.

“Yeah.”  Mary nodded in agreement, not wanting to linger on the thought as her Archer counterpart sat on the tiny Master in question.  Turning in Anne’s embrace, she wrapped her arms around the blonde’s thin waist and buried her face in her large chest.

Feeling her partner’s member start to grow back to its monstrous proportions between her legs, Anne pressed her thighs together and giggled.  Their relationship was one beyond camaraderie or pleasure, but that didn’t mean they didn’t enjoy each other’s body.  Though the massive group orgy they planned in a few days would have to wait, they could entertain each other for now.  “Come now, no more dwelling on the past, we’re alive now, and I don’t know about you but I plan on stealing the greatest treasure around.  Master’s heart!”

Peeking up from Anne’s cleavage, Mary pouted and groped her plump rear.  “I’m not going to lose to you, Anne.”

Though ultimately it didn’t matter which of them won their little competition for Chaldea’s final Master’s heart, it was in their nature as pirates, as the Caribbean Free Birds.  Free to love, free to share and free to take… each other and Master.