[TG/RC] MILF Cruise - Part 2 (Patreon)

Commissioned Anonymously

~

Ned was beginning to suspect there was something odd going on. As he walked back to their room after Peter was escorted out he was so deep in thought he was barely paying attention to where he was heading. As he turned the corner another body collided with his and he came face to face with a startled looking middle aged woman teething on her heels to avoid falling right on her ass like he just did.

Normally, this would have sent him into a stuttering apology spiral but when he opened his mouth that strange indignant rage from before began to flare and instead what passed his lips was;

“Watch where you’re walking!” Followed by a quick huff.

The woman sneered and shoved past him while Ned was paralysed in shock by his own actions. Had he just said that? Him? He said sorry when people walked into him standing ramrod still at the very edge of a hallway! Who did he think he was talking to that poor woman like that? And to add even more confusion he heard her whisper the word ‘bitch’ under her breath.

No bastard, not dick head or fuckwit.

Bitch.

An insult almost exclusively for girls and well, less than masculine guys. Now Ned wasn't the most confident in…well anything about himself but if there was one thing he could say with confidence, it was that nobody would ever mistake him for a woman. At least, that had been the case yesterday.

His fingers brushed against his lips, still swollen from his biting earlier…or were they? Surely he hadn't actually bitten that hard and even if he had they would be sore being this much fuller than normal. No, something odd was definitely going on here and he had to get to the bottom of it.

He pushed open the cabin door, ready to announce his suspicions to Peter only to find the man sitting on the edge of his bed…crying?

“Oh, you’re back.” Peter muttered, wiping his eyes clean.

“What on Earth?”

“I know!” Peter howled, “I couldn’t help it, when they escorted me back I looked at myself in the mirror and…and…well just look at me! One day and I have turned into a potato!”

Ned blinked in shock; he’d never seen Peter in this sort of state. Normally he was the epitome of ‘harden up’, he never cried, he certainly never wailed. Then again, now that Ned had stopped denying that something odd was going on he could see that his friend might not have been overreacting.

The toned, muscular body had changed. The muscles were far less defined, his belly had taken on a slightly more rounded shape and most noticeable of all his abs had gone from hard slates of muscle to pudgy and soft, his nipples now prominent and dark against his pale skin. Those were changes that couldn’t be chalked up to a lack of exercise and extra food; there was just no way!

“Peter, I think something weird is going on.” Ned said slowly, “Have you noticed how people seem to think we’re women?”

“Well with these,” Peter cupped his man tits, “Who could blame them.”

Ned felt his temper flare and he snapped his fingers twice in Peter’s face.

“Hey, focus, bigger issues than your self esteem here! I’m trying to tell you something fucky is happening.”

Peter sniffed.

“Since when are you such a dick?”

“Since you turned into a sobbing mess because you put on a few pounds. Now, dry your eyes, get dressed and we are going to sort this out.”

“Fine.” Peter pouted, “But I am going to shower first.”

He slammed the bathroom door as much as the cabin would allow and Ned found himself rolling his eyes and enjoying the newfound sense of pride filling him. What good would crying do anyway? He was right, they needed to take charge here; that had always been his problem, too meek to do anything himself. Well, he drew the line at whatever it was that was happening right now. He wasn't about to let a magic boat or something turn him into a pansy.

Peter stayed in the shower for a good long while and when he finally emerged he was dressed in another outfit from his case, this time a long skirt and flowing long sleeve shirt that strangely enough was starting to fit him better. At first Ned’s eyes slid off him but then his rational mind caught up once again.

“Why did you put on those clothes?” he asked suddenly and Peter shrugged.

“I dunno, just did. It felt right.”

Ned could practically hear the gears turning in his brain.

“I think this boat is turning us into women.” He said after a moment, eyes widening as the idea dawned on him. “To fit these clothes! Think about it, you’re a more heavyset woman with a big ass, so that’s why your body is changing so much!”

Peter’s face went through a range of emotions; mostly incredulous and shocked but then slowly Ned could see understanding forming.

“So maybe if we just spend the time naked it’ll stop?” He said hopefully.

For some reason the idea left a bad taste in Ned’s mouth which was all too easy to rationalise away. If that were the case, they would have no choice but to spend the rest of the week in their room, together, totally naked. Not going to happen.

“No, I think it’s the ship itself.” Ned said slowly, “I think we’re just going to have to grit our teeth and bare it and when once we get off the cruise hope it goes away.”

“That’s easy for you to say.” Peter grumbled, “With your sudden confidence and pretty, pouty lips!”

“You think my lips are pretty?” Ned blinked in surprise and Peter’s cheeks went pink.

“Well…yeah but they are women’s lips and I’m attracted to girls. Y’know because I am a man. A man who likes girls and you look a bit like a girl so that’s it. Stop reading so much into this God. I’m going to the gym.”

Ned could only gape as Peter raved before walking out the door without even bothering to pick up his room key. Alone at last he turned to the mirror by the wall and ran a finger over those lips once more.

They really were quite pretty actually.

~

Peter couldn’t believe his luck, or what Ned had just suggested. Grit his teeth and bare it? While the Adonis like body he had worked tirelessly to build and maintain melted away before his very eyes? Not to mention, they had no idea if this was reversible at all! What if they got off the ship in a week and he was stuck as a big bootied woman for the rest of his life. How would he play basketball? How would he get girls?!

The very idea of life as a middle aged MILF made him shudder. No, he wasn’t going to take this lying down, he was going to do something about it. If his body wanted to betray him he was going to make it work ten times as hard.

He thanked God for modern cruise ships as he stepped into the gym aboard. It lacked several of the usual items; dumbbell weights for obvious reasons but there were still treadmills and ellipticals at least as well as a few other machines. He would spend the whole crew here working off the extra weight he was putting on. It was almost soothing really; coming to a gym. WHile he preferred the basketball court this was at least familiar to him. The sights and smells gave him a sense of calm; he could work this out.

He stepped up onto the elliptical machine and started working, feeling the familiar burn in his calves…a little earlier than he was expecting but that was fine. He tried to call into the rhythm of the workout but it was difficult for several reasons. The first being the stupid skirt. It was too long and kept catching on the machine, like a constant reminder of his slowly feminising body. Then there was his body itself.

It wasn't that it didn't feel right; it was that it felt far too right. He could feel his glutes moving, rubbing together and gaining a little bounce as he sped up. He was used to the muscle there being taut but instead now he swore he could feel it shifting by the second. The loose fabric of his skirt brushed against it, getting caught in the cleft and then squashed between his cheeks.

Peter could feel his cheeks starting to burn, not from the work out but from embarrassment as he glanced at the mirrored walls of the gym. He could see himself, see the clear outline of his ass with the skirt stuck in his cleft as he bounced up and down on the machine, pumping his legs desperately.

His eyes felt like they were glued to his butt and the longer he watched the more enamoured with it he felt himself becoming. Yes, it was big but it was also shapley, lovely and peachy despite its weight; the kind of ass he'd always liked on women. Not so much himself but well, if he was going to be stuck with this body he could at least try to see the good side, right? Or at least not hate every second of it.

He was not sure how but Peter was sure that no matter how much he worked out, he wouldn’t be able to stop these changes from coming. And yet, he kept moving, but his eyes never left the mirror.

~

Harry sat by the pool feeling melancholy. This was supposed to be an amazing guys trip but here he was on the second day; alone. Peter had been escorted off and Ned had left to check on him soon after. Sure, he could have gone with them but frankly, Harry knew better. They were probably back int he room having a good bitch about him and how he fucked everything up by booking them on a women’s cruise.

Unlike most people, Harry didn't really mind when people spoke behind his back. Yeah, people being two faced was annoying but at the end of the day; it wasn't as if he actually wanted to hear people say terrible things about him. He’d rather Peter and Ned get it all out of their system together and then they could focus on actually having a good time.

The pool was a lot smaller than he originally imagined but at least the view wasn't too bad. Yes, most of the bathers were older women but that didn't mean their bodies weren't nicer to look at. There were even a few younger girls and a handful of guys their own age here. They were the minority, but it was something. Once he'd given Peter and Ned their time perhaps he could suggest they try and pick some of the girls up tonight at the bar.

He smiled to himself; he could always see the bright side of things even if his friends couldn’t. A small pop of pain in his ear followed by a clicking sound broke him from his thoughts and he looked down to see one of his studs sitting on the edge of the metal bench he’d been relaxing on.

“Weird..”

They didn't usually come loose like that. After finding the backing he moved to replace it only to wince in pain as the metal rod poked into his skin. Confused, he felt around but couldn’t seem to find the hole. A second pain and another stud fell into his palm.

“What the hell?”

The hurt was momentary but it kept coming, like being pricked with a needle, one put one his piercing began to remove themselves. First in his ears, then his nose stud and eyebrow. Bewildered, he made his way to one of the public bathrooms just in time for the final one to fall into his palm. Harry could only gape at the small pile of silver, gold and faux gems sitting in his palms; not to mention his clear skin in the mirror.

Not only were the piercing holes gone, there was no sign they had ever been there. No tiny circle of light skin or scar tissue. If anything his skin looked smoother and more luscious than it ever had. Even the marks left on his neck from highschool ache were gone. Not only that, but his skin was a shade darker, growing more olive toned after just one more hour under the sun.

He ran a hand over his own face; marvelling at just how…good he looked. After a moment he looked down to his other hand, still holding all his piercings; had he really worn so many? They had all slowly added up over the years without him realising. Ever since he turned fifteen and decided to stop caring what other people thought of him he’d never felt insecure and yet…he’d hidden behind these tiny bits of glitzy metal.

Nobody paid attention to his face because they were so distracted by all the silver and gold and that sudden realisation made him feel so pathetic. With a sneer he tipped his hand to the side and let the piercing fall into the rubbish. He had no idea how they had magically removed themselves from his skin but he was grateful. He felt like he could see his face properly for the first time in years.

He felt a flutter in his chest; excitement, he couldn’t wait to show the guys! He made his way quickly through the ship, eager to return to the cabin even if it meant hearing a few more insults slung his way. WHen they saw how good he looked they would forget all about it.

A flash of something caught his eye as he passed the gym and Harry did a double take. At first, he had just wanted to check out the woman with the fantastic ass working out on the machine, then he realise that woman was actually-

“Peter!” He cried, feeling his cheeks flushed with embarrassment, he’d been about to check out his friend! His male friend!

Though, with an ass like that, all caught up in his ass crack so that the shape was shown off, who could blame him? Nobody would ever think a butt that lovely belonged to a guy. He must have yelled loudly because Peter turned, having heard him through the thick glass and immediately grabbed at his skirt to stop it bunching up behind him before jumping off the machine.

“Dios mio, you scared me ma-what happened to your face?!” He stammered.

“Looks good doesn’t it?” Harry smiled demurely, “I’m not sure how it happened exactly but I actually think I look better without them. What was that first bit?”

“You scared me.” Peter repeated, looking uncomfortable.

“No, the first bit. Was that Spanish? I didn't know you spoke Spanish.”

“It was just ‘my god’ , hardly a rare term.” Peter shifted uncomfortably, “I probably just saw it on tv or something, I dunno why I said it. Anyway, not important, what is important is that Ned had an idea, it might explain why your piercings fell out.”

“And why your ass looks so good, I mean uh.”

“I’ll pretend you didn't say that if you pretend you never saw my skirt riding up.”

“Deal.”

“Deal, and yeah that too.”

As Peter explained Harry felt shocked, not at the news itself but how not worried he felt. On some level he knew he should be panicking, she would freaking right the fuck out but he just…wasn’t.

“I think Ned’s right, worrying isn’t going to solve anything and well, what can we do? We can’t exactly get the boat to turn around and go back to shore.”

“I don’t see why not.” Peter pouted, Harry tried very hard not to think about how pretty his lips looked doing that.

“Well, imagine if three women, one of whom has already been dragged by security for walking around topless mind you, went to the captain and told him they were actually three college guys who were transforming and nobody else could see?”

Peter’s face scrunched up.

“Yeah okay, I get your point.” He sighed, “Better to spend the cruise with free reign of the ship than down in some sort of psych hold.”

“Exactly.”

Peter shifted his shoulders a little, seemingly unsure of how to hold himself.

“I suppose being a lady is better than being a crazy lady.”

“At least we can have fun wearing all the clothes from those cases without worrying about looking weird.” Harry pointed out and a look of relief crossed Peter’s face.

“You’ve been enjoying it too? I thought I was the only one.”

“Yeah! They feel sort of nice, don’t you think?”

“Yeah and way more interesting than my usual stuff…basketball shorts only come in so many styles.” Peter flushed with embarrassment and Harry giggled.

“Do you think Ned feels the same way?” Harry asked after a moment and Peter nodded without hesitation.

“Something tells me he is enjoying this more than either of us.”

~

Ned ran a hand over the curve of his ass, admiring the shape of it in the smooth pair of white, lace covered tights. They were still a little loose but if his theory about their bodies changing was correct, soon the fabric would be stretched thin over his shapley butt.

With the others off doing god knows what he couldn’t help but go through his entire suitcase to see what was on offer; as well as the others. He couldn’t help but smile smugly when he realised the difference in his own bag. His clothes were not only brighter but higher quality; the woman they originally belonged to obviously had good and expensive taste. Ned didn't know much about high fashion, but he knew enough to know not just anybody could afford Gucci dresses and Versace leggings.

After a lifetime of baggy jeans and graphic tees it was like stepping into a whole other world. It didn't matter how much he mixed and matched his old wardrobe; he always looked basically the same. With these options he could go from classy to sultry to sexy and sometimes all three at once! Just a single belt or different pair of shoes seemed to make all the difference.

Maybe these clothes were the cause of his new surge in confidence. He’d never felt so self assured as he had the last twenty four hours. The more he thought about it, the more angry at himself he became. Why did he let people walk all over him before? Why feel guilty for telling that woman off when really, she should have been watching where she was walking?

He’d always heard those mantras of ‘if you look good you’ll feel more confident’, maybe there was some truth to it after all. He remembered the looks he’d been getting; the ones from people appreciating his body or at least the one they saw. The body that, if he was correct and he was sure he was, he would soon possess.

The idea rather excited him really, made a warmth spread through his chest and down between his legs. He’d never felt desirable before; the feeling was new and addictive, he couldn’t help but want it more. Part of him felt a little embarrassed; he'd secretly always had a thing for older women. Not old, old, just…mature. There was something comforting about imagining a partner who already knew what she wanted and was happy to teach, rather than leaving him guessing all the time.

He’d never in a million years imagined he would find himself becoming one but since he had…he might as well have a little fun. He found a sophisticated looking black checkerboard dress to go with his lacy tights and the matching pair of black heeled sandals. His feet should have been too big, yet as he slipped them into the sandals he could almost see them changing before his very eyes, becoming the perfect shape to fit the shoes.

With a wide grin he grabbed the large white, broad brim hat and went to step out into the ship. Stopping to look at himself in the mirror as he went; maybe it was the hat but he was sure his face was starting to look different too. The pouty lips were still there but the harder edges of his jaw line seemed to have smoothed, as had his cheeks. Not a single piece of stubble to be found despite it being almost three days since he last shaved.

A glint of red caught his eye and Ned looked over to where a small bag he’d discarded from his suitcase sat. Clear plastic showed a number of make up items, including a bright red lipstick. It would be a startling flash of colour against his monochrome outfit; eye catching, one might even say daring.

It was oddly simple to apply, his lips and hands almost seemed to move without his input, smearing the red across his lips with ease. He looked…good. And what’s more he felt it too, he couldn’t even bring himself to feel embarrassed that he was a guy wearing lipstick, it just felt too right.

He cleared his throat, wiping the smile off his face and schooling his expression into something cool and almost bored. He wanted people to look at him of course but he didn't want them to know he cared. He wanted everybody to think he was too hot to even remotely care what anybody else thought.

As he stepped out into the ship he let his hips take on a natural sway, the slight heel on the sandals made his but stick out slightly as his back straightened and he walked with his head held high. Then a little higher as he passed several women wearing sweatpants in public. A sense of superiority flooded him; he wasn’t even really a woman and even he looked more sophisticated and classy than them!

“I could get used to this.” He smiled to himself, it wasn’t every day he felt above anybody.

He strolled through the ship with no real destination in mind, drinking in the looks from passersby. A few were jealous women, others their husbands who were quickly tugged away, he even spotted one or two guys his own age, or former age, looking on. His confidence soared with every glance.

With grace he never thought himself capable of he slid into a stool at the poolside bar and smiled at the young bartender. He gave Ned a friendly smile and moved straight for his spot despite having just sat down.

“What can I get you ma’am?”

“A negroni.” He replied without thinking, the word just rolled off his tongue, literally in the case of the ‘R’ sound.

Now even his voice was starting to sound more sophisticated! The cocktail arrived within a moment and he sighed happily as the alcohol coated his tongue. Something about the drink felt familiar, almost homey in a way. He sipped at the drink happily for a few moments, letting the heat sink into his belly only for it to start travelling further south.

His whole body was starting to feel electric and alive in a way it hadn't for a very long time. An older man, a silver fox type, walked by and stopped to give her a look up and down before winking and continuing on his way. Something about that look lit a fire inside him so strong Ned felt his old nerves start to return.

He swallowed down the last of his cocktail and started heading back to the room as he felt his cock begin to stir. Thankfully, the dress he’d selected was tight and kept the bulge from showing, not that anybody would likely notice but he didn't want to risk it. His mind turned traitorous; it filled with images of himself with that man, naked, pinned down beneath his frame as they kissed and he plunged deep inside the pussy Ned didn’t have. He wanted it though, those mental images were far too sexy not to tempt him a little.

By the time he arrived back at the cabin he was absolutely desperate for a wank but of course, that was not to be. Before he could scan the room card he heard it; voices. Harry and Peter were back and there was no way he could get off with them in the room, even if he jumped in the shower.

His tongue ran over his lips; not to mention the make up. The clothes he could explain away with necessity but the lipstick? He might never hear the end of it! Still painfully horny and starting to feel desperate he turned on his heels and started back down the hall. He needed to find somewhere to get off and fast. Playing at being a woman had started off fun but now he couldn’t stop thinking about it; how would it feel to have a man touch him? How would it feel to have a pussy that got wetter and wetter the more turned on he got?

He pressed his hands against his chest and groaned, feeling the small mounds that he was sure would soon be breasts. His nipples had gone hard, held in check only by the tight dress.

He could feel something inside him building, almost like his muscles were tightening without his consent. He was stumbling now, his face burning and his breath coming in sharp gasps as a strange pleasure rose.

He couldn’t stop himself; his brain kept imagining sex with a man in more and more detail. He imagined himself as a sexy woman, laid out bare on a bed with a man’s face between his legs, tongue brushing against the folds.

“Oh fuck…”

He stopped, leaning against a wall, one hand pressed to his chest the other already pawing at the front of his dress. A shiver went down his spine and to his horror and utter humiliation; he came. Hard. The pleasure was quick but it bought with it such changes.

As his body shuddered he felt those small mounds on his chest swell, almost like balloons being filled with air but so much softer. With each gasp of bliss they seemed to grow in cup size, A, B, C…D; before finally stopping. Even the tight dress couldn’t stop his nipples now, they poked through, clearly visible in the pattern of his dress and Ned swallowed nervously. Something told him that orgasm was just the beginning.