Tomboy Island

Alex awoke exactly as he had been told he would.

“Do you ever need sleep?” he groaned, drowsy but by no means displeased. His morning wood was presently being enveloped by his prime slave’s cunt. He didn’t have to open his eyes to know who it was, though he did it anyway. No way would he deny himself the sight of Selana gliding down his cock.

“Not as urgently as I need your cum, Master,” the cow tomboy purred seductively.

Turning ever more gorgeous by the day, Selana sat on his cock with all the confidence of a seasoned sex slave. Her pussy, its brown colour darkened by the rush of excitement, stretched around his girthy rod. The womb tattoo glowed a soft pink, reflecting the mood of the one she had, after proper thought, given the right to call her ‘my woman’. Her arms were raised, pulling up and emphasizing her absolutely enormous tits.

They were, each, an ocean of softness, located above the toned midriff of an Olympic athlete. With their size and almost impossible firmness, just witnessing them was like observing a pair of gravity wells. They certainly held his stare, especially when her morning milk started to pearl from the large, excited nipples.

“You’re so young, dumb and full of cum in the morning,” Selana joked, lips curving into an even broader smirk as she glided further down. Pre-orgasmic shudders went through her sculpted form.

“You’re so fertile, merry and full of dairy in the morning,” Alex returned instantly.

“HAH!” Selana laughed loudly, immediately following that up with a loud moan.

Lips latched onto her left nipple, he squeezed and tasted the sweet ambrosia squirting from her milk bag. Alex had never called himself a lactation fetishist. He still didn’t. It was a simple matter of her being delicious and very much appreciating the bit of draining. Her tits needed the relief every bit as much as his balls did.

Selana came, shouting without an ounce of shame while he sucked on her tit. He gulped down what one tit had to offer, then switched to the other. A second orgasm closely followed the first. By the end of it, even Alex, whose prestigious size came with a matching appetite, was filled up completely.

There still were reserves in her tits, there always were. It would take starvation for her not to produce any milk and Alex would not let her go hungry any day in her life. He had drained her enough, though, that her nipples no longer secreted additional milk without being squeezed.

“Master, you’ve done it now!” she put a hand on his chest and pushed him flat on the mattress. “I’ll be riding you until your balls make that empty cartoon sound!”

The challenge had Alex smirk. “Go for it!”

And she did go for it - hard. The up and down of her wide hips revealed nearly all of his cock on each repetition. Obviously that was always immediately followed by her plunging back down, impaling herself on his full length. Her enormous tits moved up and down, slightly delayed after the rest of her torso. Hard nipples drew ovals in the air. They were was never still, always rippling, and shone with his saliva.

Alex grunted in bliss. From the moment he had claimed her virginity, Selana’s cunt had been perfect for him. She was tight enough that her folds dragged perfectly over all of his sensitive spots, wet enough that she could move fluidly, and, best of all, her own most erogenous spots conveniently were located right where his cock naturally stopped when her fat ass slammed against his thighs.

The smack of his skin against his, the clap of her tits against themselves, the screams of a cocksleeve going from orgasm to orgasm - all of them were the sounds that stirred the wider harem awake.

No one did more than stretch and begin to masturbate to the sight. Grumbles about volume were playful. Sapphic good morning kisses were plentiful. The orgy of the previous night found its echo in their newfound wakefulness.

Selana stopped exactly when she was supposed to stop. It was borderline precognition, to cease with his manhood all the way inside her sheathe just as his balls tightened. Tensing again and again, he delivered the first load of the day to the entrance of her womb. Feeling his seed pool inside her, the cow tomboy’s eyes rolled up. Her scream turned silent, her eyes rolled up, and she marked his groin as property of the harem with her squirting love juices.

It was only proper that he was known as theirs. What kind of man would he be if he did not allow his women to have a stake in him?

“Master… how I wish… I was fertile…” Selana groaned, the last of his orgasm getting milked by her twitching folds. “Fuck… I am completely down with the baby rabbies at this point. I’m talking to Evelyn too much.”

“There’s no such thing as talking to me too much,” the haughty dragoness chimed in.

Alex offered her a good morning kiss. Swooning, she accepted, then played with his hair as he asked Selana. “I was told you’d ‘make my balls do the empty cartoon sound’?”

“Yeah… I would love to try to make that more than a spur of the morning thing…” Selana circled her hips, shifting his still hard cock inside her. “...but that’d take me forever. If we had a Hyperbolic Time Chamber, maybe…”

“We sort of do. I am convinced there’s some time shenanigans going on every morning,” Alex reminded her. “But you’re right, we shouldn’t spend that on you trying to drain me. You would lose that challenge, after all.”

“...You’re playing me…”

“Is it working?”

“...I’ll jump you one day,” Selana vowed, then moaned while relinquishing his cock.

It was time to clean the sweat of the previous night off of them.

As they moved from one room to another, Alex did his usual scan of who had changed over the course of the night. The first change, now that he was no longer distracted by Selana’s bouncing tits, stood out prominently.

Blair’s light red hue had turned into a clear shade of crimson. The strong colour harmonized with her hair, giving her a strikingly red form. The singular colour was broken up by a variety of jagged and swirling body markings on her collar, shoulders, lower arms, sides and thighs. The black womb tattoo nestled in between, its design fitting in neatly yet visually different.

Not only her skin had changed, however. Her hips were wider, a sinful addition that fit in perfect with the black, spade-tipped tail that curved with every sashaying step. A pair of swung, black horns sat above pointy ears, underlining what she was now.

“Blair… do you have no comment on turning into a succubus?” Alex wondered.

“Not really,” the crimson demon responded. “Everyone expected something like this. Though, Master, if you want to give this a try, just give the word.”

Alex wasn’t sure what ‘this’ was, because Blair posed to show off all of her assets. One hand cupped her medium-sized breast, another spread her already dripping pussy lips. Though, considering both of those had been there before, Alex had to guess that she was referring to the monstrously long and pointy tongue that extended from her mouth all the way to her cleavage.


Alex found himself gulping. Blair already had been THE blowjob slut of the harem. Making her a semen demon was entirely matching with her personality and it also was quite dangerous. Dangerous in a way that Alex would have to experience. “I am going to take you up on that in a moment.”

His eyes darted around, trying to spot any other changes. There was nothing else as overt, though that did not mean there was nothing else.

“Guess what, bro!” Astrid suddenly jumped on his back. She was an averagely sized Swedish woman, yet she could barely wrap her legs around his waist. Hugging him tightly like a sloth would hug a tree, the playful fae pressed her breasts against his back. There was more to them than he remembered.

“Did your tits go up a cup size?”

“You know my curves so well.” He heard the smirk in her voice, then felt the soft touch of her lips again the back of his neck. A pleasant shudder was closely followed by a second. The carefree tomboy whispered in his ear, her voice soft as velvet. “I graduated from the itty bitty to the medium premium.”

“It’d be a shame if all of you just get larger,” Alex said. “I appreciate all of the sizes.”

“Is it a shame that I went larger?” she asked.

“No.” There was no need to even think about that answer. He instinctively knew this to be what he had wanted. To begin with, his harem had been tilted towards the flat and small. In the broad strokes, the breakdown now was 2 flat-chest women (Niara and Sara), 5 small breasted loves (Jane, Sofia, Yahui and Ashley), 4 medium-breasted tomboys (Astrid, Charlotte, Janette and Blair), 3 largely-endowed females (Evelyn, Valeria and Amethyst), 2 huge-titted partners (Tess and Kiara) and 1 Selana-sized sex slave (Selana, obviously).

A bit of a trend of the small-boobed ones transitioning upwards, causing a general cascade towards medium being the average, was entirely fine with Alex. He would regard it as a loss though if his current, flat-chested women went upwards by any other means than pregnancy. He truly meant it when he said he appreciated them all, aesthetically, and he would only sacrifice that unique bit of diversity on the altar of feeding the young.

They reached the bath. Rather, they reached the bath closest to the bedroom. It was a whole complex, internally separated into facilities for cleaning and those of the private bodily needs.

The massive tub had a spot that was clearly designated for him. It was a seat elevated from the remaining tub, submerging most of his shins while his erection remained above the waterline. That position might have made cleaning him difficult, had it not been for the steady waterfall, cascading down a light protrusion that went along that wall. It endlessly filled the bathtub with fresh, hot water, assuring that, no matter what debaucheries they got up to, they would always be clean.

A gap in the waterfall allowed his head to find a padded rest. The perfectly heated water fell on his shoulders, pearling down his toned figure in a manner that made the women around him drool. “Blair, this is your opportunity,” Alex said with a smile, “and my pleasure, of course.”

The redhead needed no invitation to approach him. She swam across the centre of the pool, too deep for anyone but Alex to stand in, then crawled across the shallows, where he and his woman could sit and soak, ultimately reaching the pulsing rod of her Master.

Blair licked her way up his shaft. Rather than dragging her tongue along, however, it extended as she smoothly moved towards the tip. Dextrous, the wet extension of her mouth wrapped around his manhood. Blair was hot in every sense of the word. The coiling tongue and the red lips that wrapped around the engorged head were both one or two degrees above his body temperature. It was a feverish embrace of hellish pleasure, setting his nerves alight in preparation.

Usually, Blair was one to make her mouth into a tight seal. The coiling tongue made this an impossibility. In the first seconds of her fellatio, Alex thought he preferred the traditional style of blowjob he was used to. After half a minute, he was grunting loudly. After a full minute, his eyelids were fluttering from the raw pleasure.

Blair had merely gotten used to her new tool. Her tongue was smoother than that of a human now and prehensile. The spiral of her tongue condensed into a sleeve of flesh, then stretched out again into a loose embrace. It was a repetitious pump, a secondary massage while she bobbed her head. Effortlessly, she took his girth into her throat, her heated insides undulating around the sensitive head.

Delivery desynchronized, she was stroking his shaft with her tongue and enveloped his tip with her throat. The coils of her tongue flexed in places as they moved, adding further stimulation to his sensitive spots. Her hands weren’t idle either, cupping his heavy balls in veneration and delivering tingling little scratches to the inside of his thighs.

Further testing her limits, Blair glided all the way down. Her tongue forms a twitching band around the base of his cock, a ring at which her upper lips stopped. The cumslut’s mouth formed a flawed seal around him, filling the air with the profoundly lewd sounds of her sucking him off. The undulations of her throat were clearly inhuman now, moving around him in an approximation of the folds of her cunt. She had been an eager comfort hole before, now she was developing a throat-pussy.

“Oh… fuck!” Alex was overpowered by the surge of pleasure. He grabbed one of Blair’s horns and kept her in place. The infernal succubus had held on as barely as he had. Cum surged down her throat, heavy spurt for heavy spurt, making her eyes roll up. Her whip-like tail convulsed, breaking the surface of the water repeatedly while her wide hips trembled.

They were locked in a shared orgasm, both of them rigid and twitching. Alex’s pleasure rose a little higher past the point of release. He reached the ultimate climax with a choked grunt. Dumping the entirety of the thick seed in her stomach, he kept her pinned down until he was done.

Blair was still twitching, entering the aftershocks while her tongue coaxed the last droplets out of the cock was slowly dragged up along. When his manhood left her, she mewled in the profound loss of her favourite feast. Her tongue remained extended. A multitude of strings connected them still. She was drooling a liquid too thick to be just saliva. Was her throat secreting love juices now?

“I actually have a succubus, not just as a lover but as part of a harem,” Alex groaned in delight, then guided her back down his shaft.

Instinctively, Blair knew to switch it up. Her inhumanely long tongue retreated back into her mouth and she served her Master the traditional way: tight lips and long ups and downs. It felt neither better nor worse than the new alternatives her transformation enabled. The clenching passage her throat had become, however, was a clear upgrade.

While Alex was holding onto his soul, Tess and Yahui took the liberty of cleaning him. Their hands and breasts rubbed him all over, cleansing him off sweat and other small impurities. Carefully, their hands moved around what remained of his wounds. He was healing at a clearly supernatural speed. All of the injuries he had sustained in the underground city had been reduced to scabs and fresh, pink flesh. Another day and, likely, none of it all would remain.

He came again, closing his eyes, and let the heat of their hands and Blair’s throat be all that he felt.