[TG] MILF Cruise - Part 1

Commissioned Anonymously

Three college guys accidentally book themselves on a cruise aimed at middle aged women; and then to add insult to injury the crew misplace their luggage! Or do they? The three friends find themselves each in possession of a suitcase filled with women’s clothing and nobody seems to notice that they are really men. To the point where their bodies start to change in order to fit their new wardrobe.

~

Ned had to admit; he was surprised. When Harry had told him he’d gotten them a cruise package for a whole week for basically nothing he’d been sceptical to say the least. He’d gone along with him, packing his suitcase, half expecting that when they arrived at the dock a half-sunk clanker of a ship would be waiting for them and that he’d have to get a hotel. Yet here it was, The SS Queen, resplendent in the sun without so much as a chip in her paint.

It was obviously one of those ‘classic’ cruise vessels, designed to appeal to a slightly older crowd judging by the age of the others lining up to board but that didn’t matter. Harry was flicking through the pamphlets excitedly, pointing out the luxury dining rooms, casinos and spa available.

“Just don’t ask me to play shuffleboard.” Peter sighed, standing on the other side of Ned, looking somehow disappointed.

“Come on, Pete, cheer up.” Harry grinned, “It may not be quite as wild as we hoped but I am sure there will be fun events for young people too! And even if there isn’t, we can make our own fun. I am sure there will be some ladies at the bar we can entertain…”

“Don’t we all have to share a cabin?” Peter raised an eyebrow, “Might make bringing ladies home a bit hard, especially considering I haven’t seen anybody here under forty.”

They did sort of stick out like sore thumbs, being half the age of almost everybody they had passed in line so far. It didn't help that Harry wore half a dozen piercings on any given day and was bound to stick out regardless. In his thick leather jacket and combat boots he looked distinctly out of place in this crowd; which seemed to be made up mostly of what Ned assumed was middle aged mums finally getting a break from pee wee soccer.

“Come on, Pete.” Ned groaned, “Try to be just a little less dour for once would you? We have a balcony cabin on a luxury ship for basically nothing. Only you could find something to complain about.”

“Oh, like you weren't complaining to me last night about how sure you were that this was going to be a bust.”

Ned blushed.

“Well, I was wrong, let’s try to have a good time.”

“I will, even if you negative nellie’s refuse.” Harry announced as he handed over his suitcase to the person scanning tickets.

“Thank you sirs.” The straight backed man said professionally, “Your bags will be brought to your cabin within the next three hours.”

“Can’t we just take them with us?” Asked Peter.

“It is to ease congestion on board.” The man explained stiffly, “And to ensure that the moment you step foot on the Queen you are ready to enjoy your holiday. No guest on board is to lift a finger. With our excellent staff you will never have to work or want while on board.”

“How many times do you think he practised that speech?” Ned snickered to Harry who shot him a sharp look, best behaviour, right.

“And sir.” The attendant added, “I am afraid that ball is not allowed on board.”

“I told you.” Ned sighed and Peter practically pouted.

He never packed his basketball separately, when Harry had informed him that no, in fact, the ship did not have a basketball court he had been insistent on bringing one to practise his dribbling on deck.

“I can't go a whole week with no practice!” Peter whined, but the attendant merely stared at him.

People in the line were starting to mutter and get impatient so Harry snatched the ball from his mate and handed it over. Several people behind them seemed thankful and honestly Ned couldn’t blame them, Peter had a horrid habit of dribbling it without thinking and in this big, echoey room that got old fast.

“Maybe you need to work on your guard.” Ned chuckled as Peter blinked in surprise at Harry’s swiftness before grumbling, “That’s soccer.”

They all handed over their suitcases and made their way up the gangplank into the ship and immediately, the three men found themselves in a whole new world. Titanic, the film, was one of Ned’s guilty pleasures; he knew it was supposed to be a girl movie but he’d always loved it. Now he felt like he was stepping foot onto the real thing. Plush carpets, hanging chandeliers, polished metals and dark woods were everywhere.

The ship's entire aesthetic seemed to be classy and refined, trying to recapture the glory days of ships that sailed across the Atlantic ocean. Or maybe that was just his love of the film talking. Then again, as they made their way through the wide public corridors he did notice there was a ball room aboard; complete with an events list outside that boasted several formal dances and even ballroom dancing lessons.

His mind was instantly filled with the image of the three of them attending ballroom dancing classes with a bunch of middle aged mums and he snickered. Yeah, that would go over great with the guys, Pete especially. And all those older ladies would just love Harry’s piercings.

Eventually, they reached their room, 306, and Ned held his breath; please be good. Harry swung open the door and Ned let the breath out with relief; the room was gorgeous. A little more cramps than a hotel room but that was to be expected. Three single beds lined one wall facing a wall mounted TV and mini fridge. A small desk and bench took up most of the remaining space as well as a tiny bathroom that had a fairly spacious shower for the space. All of them sharing one tiny bathroom for a week was bound to be a nightmare but he couldn't really fault the cruise for that.

Sliding doors opened up onto a white framed balcony with dividers to hide their neighbours from them and ensure privacy; something he was especially glad for.

“Hey, at least when the ship starts to sink we can jump out the window.” Peter joked darkly and Harry swatted him.

“This is going to be great! Food is covered in the cruise so we don’t even have to touch our wallets unless we want a drink or do any shopping.” Harry kicked back, selecting the bed right by the window. “I say we wait for our bags to get here, hit the pool then order room service!”

“Sounds great!” Ned grinned, secretly glad to not have to brave the busy buffet room straight away.

They set about familiarising themselves with the ship and activities on board. Ned did feel his mood dip slightly when he saw most offered activities were things like auctions and stand up by comedians whose names he had never heard of but he was sure they could make their own fun.

“The movie night selection is almost exclusively romantic comedies.” Peter pulled a face, “I guess we can just watch the pay per view.”

A knock at the door announced the arrival of their bags and Peter couldn’t move fast enough, clearly ready to get up on deck and check out the pool in the hopes that they would find some ladies their own age.

“What the hell, these aren’t my clothes!” Peter cried, the others joined him over at the bunk where he had flipped open the suitcase. Inside were a selection of brightly coloured, loose shirts and long flowing skirts, as well as bras, panties and two separate bikinis.

“They gave me somebody else's bag!”

Harry and Ned both shared a look, a sense of dread filling them; if Peter had the wrong bag, what about theirs. They both raced over to grab their own bags and opened them to find much the same thing.

“What the hell even are these?” Ned gaped, holding up a pair of leopard print tights that seemed far too large in the back, “Who the hell wears this sort of thing?”

“At least you can tell what yours is, half of these don’t even look like normal clothes.” Harry laughed holding up a dress, “At least I know whichever woman owns this stuff likes to party, this leg slit looks like it would go all the way to my damn hip!”

“That’s an ao dai.” Peter rolled his eyes, “I’ve seen the international girls wearing them back on campus, it’s a Vietnamese dress or something, or maybe chinese? Either way, you’re supposed to wear pants under it.”

Harry scrunched up his nose. No doubt imagining a week spent without his beloved punk aesthetic; the man spent more time putting looks together than most women honestly.

“Who the hell wears pants with a dress?”

“The Vietnamese apparently.” Ned shrugged. “Either way, we should probably stop going through other people’s stuff.”

He blushed, thinking about how somewhere on the ship some middle aged mother with no taste was probably going through his bag and judging him for owning nothing but graphic tees.

“We’ll go to the help desk and they will work it out.” Harry shrugged, “This will just be a blip on the radar.”

~

“What do you mean, ‘these are our bags’?” Harry cried, “I can tell you right now they’re not! I don’t care if they have our ticket number and names on them, I didn't pack myself a bag full of ladies clothes!”

The young woman manning the desk gave him a quizzical look as if she were momentarily confused by his word choice before she snapped back into her practised, professional tone.

“As I was saying, all other bags have been delivered and nobody else is reporting their luggage missing or replaced. Perhaps somebody repacked your bags without your knowledge?” She suggested kindly. “Either way if you are after a new wardrobe there is an extensive selection available on our shopping level.”

“Uh, yeah no. I ain't being tricked into spending a shit tonne of money on overpriced boardshorts!” Peter scoffed, “I’ll just wear this for the whole week, see how you all like it.”

“Please no.” Ned whimpered, “I have to share a room with you and your BO.”

“Well, I’m not spending all my money on new clothes.” He grumbled again, stomping off down the hall while Ned blushed, everybody was staring now.

“Come on, let’s not make a scene.” He begged Harry, nudging him away from the desk.

“Have a nice trip, Ma’ams!” The woman called after them and Ned felt the irritation prickle of Harry in waves.

“Fucking bitch.” He cursed, “Does she think that’s funny?”

They wheeled the suitcases back to their room dejectedly.

~

They had their room service before stripping down to boxers to sleep. They all shared uneasy looks, the silent question hovering over their minds. Could they sleep naked? It wasn't like they were all sharing a bed, and wearing the same pair of boxers constantly for a week was hardly appealing. In the end, Ned waited until the lights went out and removed his under the sheets and subtly as he could.

In the morning they woke and grimly started to put on their old clothes; even after only one wear Ned felt uncomfortable. In cargo shorts and a graphics tee that would start to smell he was afraid he might be mistaken for one of those gamers who’d never heard of personal hygiene.

“We can't do this all week, we have to buy new clothes.” Ned sighed, “It’ll ruin a perfectly good holiday if we don’t.”

“Yeah, fucking sucks.” Peter pouted, “First no basketball and now this.”

“You and your basketball,” Harry rolled his eyes, “Fine, let’s go down to the shopping centre on deck 4…hey, that gives me an idea.”

Peter grinned and Ned groaned; Harry had that look on his face; the one he always got when he came up with something hairbrained that was bound to either be hilarious or humiliating.

“Wanna make things interesting?” Harry asked slyly, “If they are so insistent that these clothes are ours I say we weather them down to the shops.”

“What?” Ned gaped.

“I bet you both…fifty bucks worth of new clothing that I can walk around in public in full drag than either of you.” Harry grinned, Ned didn't doubt it, Harry was up for all kinds of shit, the dude had no shame.

“You’re on.” Peter grabbed his hand and shook it.

“What, Peter, why?” Ned asked, why did he have to always go along with this sort of stuff.

“Look at me.” Peter smirked, indicating to his broad, athletic physique, “I walk around in a dress, everybody knows it must be some sort of dare. Nobody who looks like me wears a dress without putting on a wig and lipstick.”

“That could be arranged if we can find them.” Harry added and then it was Peter’s turn to swat him.

Ned felt a cold sweat forming on the back of his neck; that old pressure of being forced into something out of a fear of missing out. Maybe Peter was right, maybe people wouldn’t laugh? Or if they did, it would be that whole ‘laughing with you’ situation his mother and Harry were so fond of mentioning. And fifty bucks could go a long way in shorts and shirts.

“Alright, you’re on.”

Harry punched the air.

“Let’s do this!”

“If I didn't know any better I’d say you were too eager.” Ned teased and ducked just in time to dodge Harry’s palm.

Ned reached into the bag and pulled out the leopard print tights; clearly whichever woman  packed this bag was going through a midlife crisis. Oh well, go hard or go home he supposed. He slipped his legs into the tight fabric, feeling his leg hair pull slightly as the lycra sealed it in place and snapped over his butt.

He blushed feeling how loose it was but then remembered that was a good thing; if there was one thing he was grateful for, it was that he didn't have a fat ass. In  fact, he was pretty reedy. These clothes belonged to somebody big in the curve department, making them a pretty bad fit. It brought a smile to his face; it would be just like Peter said, nobody would think he actually wanted to wear this stuff. It was obvious it wasn't even his size.

Nothing in the bag seemed to match the tights, in fact, nothing in the bag seemed to match much at all.  The best option he found was a black flowing singlet that was tight under the boobs and then loose. If he had any breasts to show off, he was sure the moulder cups of the dress would do it but as it stood they hung open, showing his flat chest. The sight made an odd pang of longing pass through him before he shook it away. It was a good thing he didn't have the double Ds to fill this thing with.

“Man, you got off easy, harry.” Peter groaned and Ned turned around to see him decked out in the red ao dai with a pair of flowing white pants. The neckline was high but the flowing pants hid much of his frame, the way they were cuffed at the button though seemed to suggest they were supposed to be a bit tighter; the woman who owned them clearly never skipped leg day.

“I may have had the deck stacked in my favour.” Harry shrugged.

“Only a little, it’s still obvious that they are women’s clothes.” Ned pointed out.

“Not as much as yours.” Harry smirked, eyes dipping to his open chest.

“Yeah man, you got it the worst.” Peter agreed and Ned took in his outfit.

A red singlet, clearly a female cut with a neckline embroidered with little beads and a pair of jeans. The fabric hung off him awkwardly, clearly meant for a plumper, more heavyset woman but otherwise he looked pretty fine. No hanging cups to be found. He almost looked normal! Well, aside from the massive sag around his ass, Ned thought his clothes belonged to somebody with a lot of junk in the trunk but Peter’s was something else. Who could possibly fill up that much space?

“Alright then ladies.” Harry announced, “Let’s strut our stuff!”

Ned could feel his whole face burning as they started to walk, as soon as they set out of the room hallways into the public area’s he felt that head spread to his neck and shoulders as well. So not only was in a cross dresser, he was a bad one and red as a lobster. Going hard was wrong; he definitely wished he’d picked the go home option. But he couldn't let Peter and Harry win so easily.

He kept his eyes on the floor as long as he could until he started noticing other people’s shoes passing and forced his eyes up only to be met with…nothing? Nobody was staring, nobody was snickering, barely anybody paid them any mind save the odd polite smile.

It wasn’t awkward either; these were not the tight, uncomfortable smiles people gave when they saw something odd and didn’t know how to react. They were just the usual ‘hey, I’m passing you and acknowledging your existence’ smiles. Peter and Harry looked equally confused.

“Did we somehow walk onto the world's most accepting ship?” Peter asked, “That lady looked like the stereotypical conservative and she didn’t even sneer.”

“Yeah, I was sort of hoping for more of a reaction. Or any kind of ration.” Harry shrugged, “Oh well, I guess we can get our new clothes and be done with it then,”

Ned slowly felt his embarrassment fading; if nobody thought it was weird it must have been okay. They stepped out onto the promenade and were immediately met with lines of glitzy shops selling everything from swimwear and lingerie to everyday clothes. They headed for the least expensive looking store with a host of bikini clad mannequins in the window and started looking.

“Uh, do you have any board shorts?” Peter asked the sales clerk after a few moments, “I only see ladies swimwear.”

It was one pieces, bikinis and everything in between but nothing remotely masculine.

“No sorry.” The woman behind the register smiled, “We removed all the male stock for this cruise because of the theme.”

“Theme?” Harry blinked in confusion, “I didn't see a theme when I booked the tickets.”

“Oh well that was fortunate.” He laughed, confusing them further, “It’s the ladies classy cruise.”

Ned felt like a brick had just been dropped on his head.

“Ladies…classy cruise?” He echoed.

“Yes, a week away aimed at all those mature ladies who are looking to let loose and feel young again! We’re catering to the mom crowd especially, you know, the ones who haven't been able to go out to the bar for a few years because they're too busy with the kids.”

Peter and Ned slowly turned to Harry with malice burning in their eyes.

“But I am sure you can find something to your liking in the selection” The woman continued.

“That’s uh, very forward thinking of you, but no.” Ned replied, ignoring her confused look, “We’ll go check the other shops.”

Of course, that was a bust. This was a luxury cruise liner with clothing shops for every occasion; they found everything from sundresses to ballgowns, but nothing remotely manly. Even the pants, jeans and shirts were all of an obviously feminine cut. Ned tried in vain to fit into a pair of jeans only to find the legs far too skinny at the bottom and too wide at the top, leaving him with a saggy butt just like Peter.

“How could you book us onto an old lady cruise?” Peter hissed to Harry as they walked back to their room with sheepish expressions.

“It was so cheap and I mean really, who reads all that fine print?” Harry argued. “I am sure we can still have fun.”

“No wonder there was no speed dating…” Peter grumbled, “Our chances of getting any tail are now pretty limited, unless either of you have a MILF fetish you’re ready to reveal.”

‘Not reveal no…’ Ned thought to himself.

“Well, we’ll just spend time chilling, eating room service if nothing else.” Harry waved their concerns off and Ned felt his blood start to boil.

Normally he would just go along with this sort of thing but right now a new feeling was coursing through his veins; overpowering his shy, embarrassment for the first time.

“No, we are going to the buffet.” He announced matter-of -factly, “In these clothes and you are going to eat like that.”

“Wha-what?”

“You heard me.” Ned put his hands on his hips, “You got us into this mess and I’ll be damned if you manage to just wave it off like you always do. You’re going to dinner, in that ao dai in front of everybody.”

Harry shrunk in on himself a little, his cheeks turning pink.

“B-but I’m a white guy.” He whimpered, “Walking down a few hallways is one thing but I don’t want people thinking I’m some sort of…culture appropriating ass hole. They might think I’m making fun of Vietnamese women for something.”

“Too bad. This was your idea.” Ned only felt more confident as he kept walking. “Come on.”

Peter raised an eyebrow.

“Holy shit, it took putting on those tights for you to find your balls, Ned.” He said, sounding impressed, “Nice work.”

It did feel good, he had to admit, cowing Harry for once. The man was following on behind with his head bowed in embarrassment and shame. It was almost like they had switched positions and Ned felt his steps getting longer and more confident; he didn't even feel embarrassed by his clothes anymore. Especially when they stepped up to the dining level and into the buffet without anybody turning their head.

Well, that wasn't strictly true, plenty of people’s eyes dipped to his chest; especially the handful of men that they walked by. Each of them on the arm of a woman who seemed to tug them tighter as he passed. Almost like they were jealous that their husband was checking out a competitor. The idea was so laughable he had to bite his lip hard to avoid snickering. By the time they found a good table his lip was starting to swell from the pressure.

“Alright, I’ll sit here and hold the table, you two go get your food.” he told them and Peter gave him a sarcastic salute.

“Yes sir!”

Ned wasn't sure what possessed him but he stuck his tongue out and Peter snorted. Harry was still demurely standing with his head down looking nervous; despite the fact nobody was really paying him any mind. Perhaps he had been right though, nobody seemed to care about their clothes, perhaps they could just wear them without an issue.

Peter returned quickly with a mishmash of hes on his plate.

“Food is fuel.” He shrugged, shovelling pasta into his face, “Carbs and energy are all that’s really important, not taste.”

When it was Ned’s turn to hit the buffet he took his tray and started looking over the offerings and found himself suddenly hit with a craving for pasta. He looked over the offerings and felt his face twist in disgust; it was all so mass market. Pasta was a homey food, simple and delicious, all the options on display were so needlessly fancy. Not to mention the limp tomato paste covered paper they were passing off as pizza.

Italian food was his favourite and they had somehow butchered all the options. He was suddenly hit with the urge to call out the chef and explain to him that any five year old could make spaghetti better than this offering but he once again bit down on his lip. Telling Harry off was one thing but making a scene in front of all these people? No, he couldn’t do that. He was sure the chefs knew how to make something right, just not Italian food by the looks of it.

FInally he managed to find a roast and some veggies that looked edible and made his way back to the table. Licking his swollen lips on the way. They seemed to have almost doubled in size thanks to his biting; he’d have to put a stop to the habit. He could see his distorted reflection in the metal tray and to his surprise, found his lips didn't look all that bad. Pinker, more full yes, but not bad. Ned giggled to himself; it was almost like they matched his clothes.

~

Ned was lounging by the pool, hot women with MILF style bodies were parading around in skimpy swimwear, eyeing him with hunger. One leaned down over his chest and it was then that he realised he was naked. Her lips pursed around his nipple and she started to suck, drawing out the most wonderful, ecstasy filled moan from him as pleasure pooled in his stomach. It felt so lovely, his whole breast was tingling and-hang on, breast?

Ned blinked his eyes open and found himself hard against his mattress; that was the weirdest wet dream he’d ever had and he was thankful he’d fallen asleep on his stomach so the evidence wasn't standing up for his room mates to see. His face was warm and unlike most dreams, the memory of this was still crystal clear in his mind. All that cross dressing yesterday had really gone to his head. He tried not to read much into it.

With a groan he waited until his hard on softened and he rolled over. His chest was killing him, probably just the lingering memory of the dream though. At least he hoped, the last thing he wanted was to get sick in the middle of the ocean, miles away from a hospital.

“Man, I had the weirdest dreams.” Peter groaned, sitting up in bed before crying out in shock and causing both Ned and Harry to jump.

“What? What’s happn’?” Harry asked sleepily.

“Look at what this damn cruise has done!” Peter cried, looking down at himself, “One fatty meal with no basketball practice to burn it off and I am putting on the chub.”

“Nobody gains weight that fast.” Ned argued, “You’re imagining it.”

Though he had to admit, at first glance he could see what Peter was talking about. His friend put great pride into his physical prowess and Ned was sure his muscles didn't look as defined as usual this morning. As he swivelled his legs over the side of the bed Ned could even see a roundness in his belly that had certainly never been there before. Peter took any chance he could to be shirtless in order to show off his washboard abs, abs that were currently nowhere to be seen.

“You look the same as always.” Ned lied, a little confused.

He was right though, people didn’t gain weight that fast normally. Maybe Peter just had a slow metabolism or something?

“Well, you may be getting fat but I am getting tan!” Harry bragged, looking at himself in the mirror by the desk, “Check me out, I was only out on deck after dinner for a little bit and I am already getting a healthy glow.”

Ned’s brow furrowed again, Harry’s skin was definitely a slight shade darker, but it didn't look like any tan he’d ever seen. If anything it looked like a light olive colour; more akin to somebody of Asian descent than a white guy who stood in the sun too long. But it had to be a tan, surely, what other option was there?

He tried to put the thoughts out of his mind and focus on more important matters, like finding something to do. He grabbed the events pamphlet and scanned through it; they actually had shuffleboard, who’d have thought.

“Well, I don’t know about you but I am going to hit the pool.” Peter announced, “I can wear my boxers and dry them on the balcony, I need to work off this chub before it settles in.”

“A little sun lounging does sound nice, I’ll meet you there after breakfast?” Harry asked, it was obvious Peter would be skipping in favour of burning carbs rather than putting them on.

“I’ll come with you, but uh, then I might just come back here.” Ned said, trying not to sound too suspicious, after his dream last night he didn't trust himself by the pool.

He was halfway through slipping his legs into a black skirt when he realised just what he was doing. He’d not even thought about it, he’s just started putting on another outfit from that bag. His eyes fell on the clothes he'd worn yesterday, his only masculine set. The memory of the hot waiting room made his skin crawl, putting on those sweaty clothes wasn't exactly appealing.

Everybody had been chill about him walking around in women’s clothes yesterday…maybe he could do it again? Besides, he had to admit the way the panties cupped his front did feel quite comfortable. Maybe all those people who swore by briefs were onto something. The pencil skirt was rather freeing too, even if it was a bit tight around the legs.

I managed to find a blouse that looked enough like a button up shirt that maybe if people couldn't see my legs they wouldn’t notice anything was amiss and headed out to breakfast. Harry seemed to have taken a page out of Ned’s book and was dressed in a conservative button up shirt and long loose pants embroidered with little fish. They were actually pretty cute but there was no way Ned would tell him that.

Just like yesterday, nobody seemed to even bat an eye at two young guys wearing women’s clothes at the buffet line. And maybe it was just him getting used to things but Ned was actually starting to enjoy how they felt. He kept stealing glances at himself in his silverware, angling them so he could better see the outfit.

Suddenly, gasps echoed out across the room and people began to mutter. Ned looked up from his spoon to see Peter walking across the room in his boxers looking thunderous.

“They threw me out of the pool!” He exclaimed, “They told me I had to wear a top of some kind!”

People around them were staring, some were averting their eyes in embarrassment. Ned couldn’t help but think it was a bit strange; after how chill everybody had been with them walking around in women’s clothes, a pair of boxers made them uncomfortable?

“Ma’am, you need to put a shirt on.”

Security was right behind Peter, walkie talkie in one hand.

“Alright, alright I am going!” Peter threw up his hands in defeat.

Security followed after leaving both Ned and Harry in stunned silence; the whole room was acting as if they’d never seen a topless man before. It was only after he’d finished his breakfast and started heading back to the room that Ned realised the security guard hadn’t said ‘sir’, he’d said ‘ma’am’.