First Time for the New Girl (Patreon)

Since I'm sure some of you aren't overly fond of crossdressing/gay content allow me to assuage your concerns: this is just one of many fetishes I enjoy. It's not gonna take over my patreon or anything lol. So if you don't like it give this one a skip and rest assured the next with feature some good old fashioned lady parts. But obviously if this is your cup of tea and you're at a tier to do so feel free to suggest more when the time comes!

“Well, well, well . . . you must be the new 'girl' the Madame took in. I can see her praise wasn't description wasn't exaggerated in the least!”

Aladdin blushed behind the wispy blue veil covering the lower half of his face. He stood in the center of the lavishly decorated private bedroom while the visiting sultan was still admiring him from the doorway. Despite knowing it would happen eventually the former street rat was still a touch nervous about finally serving his first client. His trepidation was made all the more palpable by the outfit his customer had bidden him to wear. Billowing sky blue satin leggings cut low enough to reveal his pubic hair, if he'd had any, but still riding high on his hips covered his lower half. Most of his chest was left exposed save a very low cut tube top with sewn in sleeves that really only served to draw attention to his lack of breasts. A pair of matching slippers with tips curling back over his feet along with a similarly colored headband embedded with a large jewel in the center, a plain golden necklace, and a pair of ornate golden earrings completed his copy of Princess Jasmine's well known attire. At the Madame's recommendation he'd grown out his thick black hair until it was well past his shoulders and kept every inch of his body save his eyebrows shaved to complete the look.

“Thank you your highness,” Aladdin said in an uncharacteristically feminine voice.

The sultan chuckled and stepped fully into the room, shutting the door behind him and saying, “It seems I'm not the only one enjoying how the Princess' clothes fit you!”

Following his soon to be lover's gaze Aladdin's cheeks darkened even further upon seeing the unmistakable erection swelling between his thighs. Evidently he enjoyed dressing as Jasmine and being ogled more than he even realized. With a laugh the Sultan strolled towards a pile of lavish pillows to plop down on the mound. He stretched his arms above his head, sighed, and grinned. Before Aladdin could approach his companion reached into his loose fitting breeches and pulled out the biggest cock he'd ever seen. Admittedly the young prostitute hadn't seen more than a handful in his time, most of them during lessons from the more experienced girls, but even with that small sample size he knew the sultan was above average. As thick as his wrist and about as long as his forearm the veiny monster pulsing expectantly only a few feet away filled him with a mix of excitement and trepidation. His legs actually trembled a little as he slowly approached and knelt down. His Madame had made it explicitly clear that he was to always start with oral unless otherwise specified and he had no intention of going against the grain. Well that and the thought of tasting such a lovely looking prick made his heart flutter in his chest.

The moment he reached towards the waiting cock the sultan released his hold. The weighty member instantly pitched forward and Aladdin was forced to catch it with both hands or risk being slapped in the face with it. His partner chuckled at the clumsily way he held the dick, his style clashing between inexperience and an attempt to appear skilled. He licked his lips behind the veil and leaned in close, gently stroking the thick rod with both hands as he did. The familiar stench of precum, sweat, and masculine odor overcame him. Aladdin couldn't remember the last time his body had produced such a smell. The special tea his employer had been giving him since he started working had all but shut down the more manly side of his bodily functions. Aside from his cock little about him could even be considered manly. Certainly not the perfumes that always clung to his bronzed skin. Thus suddenly being in the presence of a medley of odors so undeniably male was quite overwhelming. Without even realizing it his mouth fell open in a barely audible moan and his eyes slowly glazed over. He continued rubbing the sultan's dick with subtly faster motions, his libido more than making up for the sudden drop in intelligence. 

One hand momentarily left the sultan's cock to lift his veil so he could lean in and tenderly wrap his lips around the sticky head. An immediate and rewarding groan emerged from his lover's mouth and Aladdin trembled with excitement. He let his silky shroud fall back down to partially obscure what his lips were doing and slowly pushed his way further down. The first few inches slid into his mouth without any trouble whatsoever. He might not have been experienced at riding men but her certainly knew how to suck them off. His efforts slowed a little about a third of the way in as the tip neared the back of his mouth and his gag reflex started to kick in. Aladdin ignored it as best he could and continued unabated. But his body had never tackled such an impressive specimen before. The walls of his throat tightened around the sultan's shaft, providing a new level of pleasure for him but making the relatively inexperienced prostitutes job that much harder. Spit started to leak from the corners of his mouth as his body went into overdrive. Tears welled in the corners of his eyes and he was forced to pause for a moment to gather himself. Or at least that's what he would have done if his horny brain hadn't bidden him to keep going as fast and hard as he could. Almost as if he wasn't in control of himself anymore Aladdin suddenly threw himself forward with enough force to shove the sultan's dick most of the way down his esophagus. He stopped just shy of three quarters, his gagging body all but forcing him to concede that the sultan was simply too big to completely fit.

In truth it was a little disappointing that he couldn't take it all like the other, actual women he worked with. But in practice it simply meant he'd have to try that much harder. Slurping noisily around his cock to try and suck up some of the errant saliva trickling out Aladdin slowly lifted himself off the sultan's prick. Wet gurgles filled the air as every inch that passed through his convulsing passage rubbed against his soft walls. In the short time it took him to reach the top copious amounts of saliva had dribbled all the way down the sultan's rod to pool around the base. Blushing slightly in embarrassment at the mess he was making Aladdin paused to look at his customer with wide, unblinking eyes. The sultan nodded after staring at him for a few moments, an impressed and satisfied grin spread across his face. More eager than ever he slammed himself back down on the cock before him it all but vanished from sight in an instant. Though stymied towards the bottom as he had been before, as well as his own wildly protesting gag reflex, Aladdin didn't hesitate for a moment to pull back up. Or slide back down at the apex of his movement. Soon the room was filled with the sounds of slurping dick sucking as his head bobbed up and down as much of the cock as he could. He refused to slow down long enough to take a breath, loving every moment of his oral demonstration like he had all the others, even when his vision started to dim and his body cried out for air. It was all far too enjoyable for him to worry about such trivial things as breathing, not when he had such a weighty challenge to overcome. Or more likely to submit himself wholly to.

Going for as long as he possibly could Aladdin only pulled up when the threat of suffocation was too great to ignore and his body all but forced his actions. He gasped and moaned in a very feminine way, his eyes practically sparkling with excitement. Spit and precum drenched his veil, making the already clingy fabric stick to his face like the wet rag it had become. His nostrils filled with the scent of his messy blowjob and Aladdin was torn between peeling it back so he could continue and breathing in the amazing smell. His hands picked up where his mouth had left off and stroked the sultan as fast as they possibly could. All the lubrication from his deepthroating made it impossibly easy for his fingers to glide up and down his full length, though his nerves prevented him from squeezing it much harder than a tender grasp. He was just about to dive back onto the sultan's shaft for another go when his authoritative companion spoke up.

“Stand up, it's time I put you to the test!”

Despite the sultan's words Aladdin kept sucking for a few more seconds, his newfound addiction spurring him to continue. Something in the back of his mind eventually bid him to stop however, mostly when it reminded him that that beautiful dick would be inside his ass if he did. Pulling away and rising to his feet Aladdin quickly grabbed a bottle of sweet smelling oils from beside the bed. As the sultan stood up he poured a generous amount onto his hands and quickly grabbed his partner's swaying dick. Stepping in so close they could have kissed if not for the veil Aladdin spread over every centimeter of cock his hands could reach. Despite the man's size it didn't take him long to make sure the whole thing was dripping with oil in just a few seconds. He couldn't stop himself from rubbing it even after he was done, savoring the feel of it and the tease of what would come next. The sultan allowed him his fun for a time but eventually his twitching cock got the best of him and he grabbed Aladdin's shoulders. He spun the slender prostitute on his heels and pushed him to the edge of the bed. With one hand he cupped his nonexistant breasts while the other pulled his leggings down to reveal the bubble butt he'd glimpsed earlier. While his now useless bottoms slid past his knees Aladdin fell forward onto the bed and buried his face in the sheets. He would have crawled onto the soft bedding for a better position but his partner didn't have any intention of wasting another moment.

“Take a deep breath.” The sultan commanded, “This will be a surprise!”

Aladdin tried to do as he was told but simply couldn't inhale past the lump in his throat. He was so worked up he jumped a little when his lover suddenly slapped his well oiled cock against his womanly ass, even letting out a little squeak. The warm heaviness of his prick was dragged across Aladdin's plump ass until it slid between his buttocks. As the tip pressed against his virgin hole he sucked in as much air as he could and grabbed the sheets. For a moment it simply pulsed against his asshole with only the slightest pressure accompanying the position. But soon the force started to build and his nubile little hole strained against the attempted intruder. He followed the lessons he'd been given as best he could: paradoxically pushing out against the cock and relaxing his entire body as much as was humanly possible. The effects were as immediate as they were surprising. In an instant the sultan's dick found purchase within Aladdin's ass, a small portion of the tip gently sliding past his opening to at long last enter his second hole. And as soon as that little bit made it the rest was soon to follow. The sultan kept his pace steady and more of his shaft slid inside. Pleasure and no small amount of pain filled Aladdin's body as his asshole was finally claimed by what was sure to be the first of many customers. The sultan had been told ahead of time he was the first customer to enjoy the young man's ass, a fact that had more than justified the additional cost. When all of his swollen head was buried inside the moaning slut's backdoor he was more certain than ever the price had been will worth it.

The smooth, warm walls of his ass clamped down around the sultan's cock in a flurry of uncontrollable spasms and twitches. It tried to push him out and suck him deeper at the same time, all while Aladdin squirmed. His own, vastly smaller cock was throbbing so hard against the bed it would have hurt if his mind hadn't been so preoccupied. For a moment he entertained the notion of trying to stroke it, perhaps making his own body a little tighter from the added pleasure. He didn't get the chance to however as the sultan suddenly leaned forward and slid a hand beneath his taut belly. Soft fingers closed around his impotently throbbing prick. At first Aladdin hoped his surprising companion would do what he'd been contemplating a split second before. Instead the sultan liften the whore's body off the bed just high enough to pull his dick out and over the side where it could freely twitch and release precum all over the sheets. The man's approving nod was missed by the still overwhelmed Aladdin, the latter's attention being yanked back to his once virginal ass and the huge piece of meat now sliding deeper. With all the oils that had been lathered across it his cock was almost effortless in it's journey into his deepest reaches. After the way had been bridged by the considerably larger head everything else that came afterwards felt almost normal in comparison. Especially to the newly discovered anal whore side of Aladdin that he'd barely been aware of. It all felt so perfectly natural and even completely satisfying he didn't even think about just how much was gliding inside him until he felt a cum laden pair of balls bump gently against his own. The moment he realized what he'd just accomplished Aladdin straightened against his companion, reaching behind him to grab the back of the sultan's head. 

“Are you sure you haven't done this before?” The sultan asked softly. Aladdin shook his head and whimpered a little as both their dicks throbbed, “Perhaps your body was made by Allah for my pleasure . . .”

“I-it was!” Aladdin whimpered.

“I know.”

He pulled back with those gloating words still ringing in Aladdin's ears. Not so long ago he would have bristled at the blatant arrogance. But after his transformation, and with a juicy dick stuffed up his ass, he found the confidence nothing short of intoxicating. The sultan's shaft retreated until barely a quarter of it remained inside his ass where it belonged. As soon as he stop pulling out he thrusted back in with a strong, smooth stroke. Aladdin gasped and his whole body tensed from the burst of stimulation. There was something different about the second time he entered his ass, something even more gratifying. It took a few more  thrusts for the former anal virgin to realize what. Even if he couldn't put a name to the feeling he knew the sultan was hitting something special each time his prick slid back inside. Almost like a special spot buried deep in his ass whenever his lover's weighty dick brushed against it a rush of pleasure filled his body and threatened to overtake him. As the speed of his movements increased the frequency of that sensitive place increased. In a little more than a minute it seemed as though the sultan was attacking that part of him directly and with great effect. He couldn't contain his pleasure even if he wanted to and the whimpers that escaped his lips encouraged his companion almost as much as his wonderfully tight hole. Every thrust, already a pleasurable experience on its own, was amplified and made nearly unbearable the moment his dick passed by that g spot. But perhaps best of all was the fact that the sultan's shaft always continued well past his button to glide amazingly deep inside his ass.  Which meant it was hit a second time when his dick scraped against it on the way out. With such a constant and mind altering source of pleasure flooding his body it was simply amazing he managed to hold on for nearly five minutes before it was all finally too much to bear.

Aladdin's increasingly girlish moans reached their crescendo after being pounded mercilessly for a full minute by the sultan's titanic member. He squealed so loudly every room in the building heard and shut his eyes as tightly as he could. The veil across his face fluttered madly from his ragged breaths while his flopping, half soft dick finally blew it's load. Without growing another centimeter thick, gooey strands of cum seeped out of his tip in quantities he'd never produced before. It was as though his body and mind had finally come to realize his true place was as someone else's cock sleeve. As the sultan continued to fuck him endlessly his unpredictably shifting dick sent streams of pent up semen everywhere, his spunk splattering across the bed, the floor and even the ceiling. The tighter his ass squeezed the source of all his pleasure the harder he was fucked in return and the more erratically his streams of jizz were flung. Much of it ended up splattered across his taut stomach or soaking into his once immaculate blue satin garments. After only a few seconds he'd unloaded more cum than the last three times he'd jerked off combined and the flow was only just starting to taper off. It didn't help, or rather it helped very much from a certain point of view, that the sultan was relentlessly pounding his g spot during the entire thing and all but ensuring Aladdin remained a whimpering, cock crazed mess throughout. By the time it was well and truly tapering off the entire room smelled of cum and his lower half was completely soaked with messy strands and stains, none more coated than his own, otherwise useless shaft.

Cum continued to drip from his prick in long, sticky strands well after his first big climax had come to a close. But with all the pleasure still flooding his body and a beautiful cock eternally hammering his ass there was never any shortage of ecstasy to go around. Aladdin probably could have gone on like that for hours. Part of him was even hoping it would. After such a powerful and amazing orgasm all he could think about was how long it would take to have another and what he could do to reward his kind benefactor for teaching him just how much he enjoyed and deserved getting dicked. The sultan clearly had other plans though as his thrusts grew more animalistic and powerful by the second. He fucked Aladdin like a man possessed and just in the brief frenzy following the young slut's climax he almost brought the black haired 'girl' to another orgasm then and there. Before he could lose himself in another wave of full body bliss his well endowed partner let out a telling groan and pushed his shaft balls deep inside Aladdin's perfect little ass. The entire thing swelled and his balls tightened immeasurably against his partner's much smaller sack. Both of them moaned in excitement as the first rops of what was sure to be a mighty cumshot flooded his ass.

Sure enough the toe curling spray of jizz that basted his inner walls felt all at once like a dam had burst inside him and as though some previously unknown missing piece had finally been added to his life. Aladdin screamed in breathless exultation as his body was filled with more cum than he ever dreamed possible. Not only did the sultan produce vastly more than he himself had released he produced more than what a horse could likely create. It flooded every part of his ass that it could, reaching so deep inside him he wondered if it might actually emerge from his mouth. Sadly nothing quite so spectacular happened but he was still treated to an entire belly and ass full of impossibly thick jizz straight from the source. He clamped down around the sultan's shaft as hard as his quivering body would allow, ensuring not only that every drop remained exactly where he wanted it but that he milked it all out like the good little whore he was supposed to be. The gushing wave of jizz was matched only in pleasure by his own body's complete acceptance of the role he'd been destined to play. Nothing in his entire life felt more right than having a big, fat dick pumping cum into ass. If it had gone on much longer he might have even had another orgasm, complete with a fresh wave of his own seed and not a single moment of attention paid to his almost pointless dick. But as impressive a specimen as the sultan was he was still a man and eventually the voluminous spray of semen had to come to an end. Thankfully that end didn't arrive until after a full thirty seconds of wild throbbing and the occasional thrust to emphasize a particularly strong jet of spunk.

At long last the sultan's balls were finally and completely drained. With a final shuddering laugh his dick slid out of Aladdin's ruined hole and the exhausted prostitute collapsed onto the bed in a puddle of his own cum. He knew his asshole was still gaping wide from the monster he'd just satisfied but in his post sex weariness he couldn't even begin to care. About all he could do was slid his knees under his prone body to make his ass stick out even more and give his companion a nice look at the mess he'd made. It was the least Aladdin could do to after receiving so much pleasure from someone he was supposed to take care of. Remembering some of the sessions he'd witnessed before he bit his bottom lip and started pushing as hard as he could. The walls of his ass momentarily closed and bubbling cum was forced out in a sudden, viscous river. It dribbled out of his stretched orifice and trickled down his shaved body, gliding across his sack to finally join the rivulets still clinging to his soft dick. He kept pushing until his body couldn't take the stress anymore and he dropped to the bed once again. More than a third of the sultan's jizz had been squeezed out and he could feel it slowly dripping down his member and onto the soiled sheets beneath.

“Ah what a beautiful sight,” The sultan cooed, “I make no exaggeration when I say you're the best I've ever had!”

“Thank you . . .” Aladdin whimpered, smiling and hiding his face in embarrassed pride.

“I guess it only makes sense the best woman for a man like me isn't a woman at all. At least not where it counts.”

Aladdin gasped and tensed as his cock and balls were unexpectedly groped by his partner's large, albeit soft hands. A little more cum dribbled onto the sultan's palms and he laughed. He gave the half naked courtesan's ass a wet smack to rid himself of the warm fluids and Aladdin moaned. Unable to stop himself he pushed his still jiggling butt out a little more in the hopes of another hit. The sultan was more than happy to oblige and another playful spank was administered to his other cheek. A powerful tremor spread down the young man's spine as his body instinctively tried to shy away from the contact, even though it savored every stinging second of pain and pleasure. Sadly when he turned around to look at the sultan the man had already tucked his cock away and looked about ready to leave. Aladdin licked his lips behind his veil and watched the man that had taught him so much in such a short amount of time. 

“I believe my time is up,” The sultan grinned, “Until next time my sweet . . .”

“Aladdin.”

“Until next time my sweet Aladdin!”

He sauntered out of the room after  one last roguish grin. A minute or so later the Madame of the brothel stepped inside and clapped her hands. “Well done!” She congratulated, “Sultan Almasi loved you. He even asked how much it would cost to add you to his personal harem.”

“W-what did you tell him? Aladdin asked in a soft, slightly hopeful tone.

“That he'll have to wait until I know what you're worth. If he's still interested when he returns in three months I'd be happy to negotiate a price. Until then, you have two more customers waiting in the hall.”

“Already?”

“Yes. They both have a certain fondness for going right after someone else. You're the freshest of all my 'girls' and they're eager to try out something different. I'll send them in now. Stay just as you are.”

“Yes Madame.”

Her soft footsteps retreated from the room and much heavier ones quickly replaced them, “Damn! The last guy really did a number on this little slut!” A gruff voice laughed.

“Yeah, guess we're gonna have to wreck him even more!”

Shivering in anticipation at their words while his cock started to harden below him Aladdin pushed his ass a little higher into the air and softly moaned, “Don't hold back . . .”