FEMINIZED! First Time Crossdressing

Chapter 1

“This place looks amazing!” Ashley exclaimed as the coach pulled up outside the gates to our resort.

“Oh my god, we’re going to have so much fun!” Becky laughed.

“Let’s hit the beach like immediately,” Kelly chimed in.

And even though I had to admit it did look pretty cool, I couldn’t join in on the girls’ enthusiasm, instead just sinking further into my seat at the back of the coach, their voices grating on me yet further after our eleven-hour flight.

“Your dad is so cool, Ashley,” Becky added, as the engines cut off and the passengers at the front started to file out to collect their luggage and check into their rooms. Cool was one word for it.

Another would be asshole. You see, Ashley’s dad was the whole reason I was here on this stupid trip – chaperoning three eighteen-year-old girls on the ‘vacation of a lifetime’. Let me explain. My name’s Paul, and a couple of years ago, just as I was starting college, my mom remarried. My real dad passed away when I was still a kid, but my memories of him were all of a kind, gentle man – slim and soft featured, a little like myself. But Frank, my mom’s new husband, couldn’t be more different.

He was a real hard-ass, a man’s man, always going on about his time in the army, or the cutthroat world of business, shit like that. Luckily, I didn’t have to see him too much, already being away at college most of the time, but when I did come back to visit it was hell. He was always making little jokes and jibes about how, if I’d been his son, he wouldn’t have let me study such a sissy subject as Graphic Design, which I was currently majoring in. And the way he spoiled Ashley, my new step-sister, was insane.

Always buying her whatever she wanted, always lending her money; in his eyes, she could do no wrong. So when she’d asked him this summer if she could take a couple of friends away on a ‘girls beach holiday’ to Europe, he’d agreed of course. But even though he did anything she asked of him, he was also pretty strict about her safety. Which is where I came in.

He’d taken me aside one night, dropping the news that I was going with them – telling me, rather than asking me, leaving little room for negotiation. It was probably some alpha male business technique he was using on me, and what’s worse, it worked. I had little option but to mumble, “Sure, Frank,” as he laid out his plan for the holiday. I was to accompany the girls at all times, to make sure that they didn’t drink any alcohol even though the drinking age was younger over there, and most of all to make sure they didn’t get involved with any boys.

Ashley had wrinkled her nose up in disgust when he’d told her the news that her boring geeky stepbrother was coming along on her awesome summer vacation, too, and I had to bite my lip, to stop myself from announcing that actually it sounded like hell to me, too. Because unlike bratty, annoying Ashley, I just yearned for a quiet life – didn’t want to cause a scene – especially knowing it would upset my mom if I complained. Which is how I found myself here. Chaperoning three eighteen-year-old girls on some stupid-ass beach holiday.

But what I didn’t know back then was that this really would be the ‘vacation of a lifetime,’ not for Ashley and her friends, but for me …

“I’ll take the bed in the middle!” Ashley announced, racing into the large room that the three girls would be sharing and dumping her bag down on the crisp white sheets.

“I’ll take this one!” Kelly laughed, claiming the bed by the patio windows, that led out onto a large sunlit balcony.

“I guess I’ll take this one then,” Becky said happily, gesturing to the final bed which was next to the door to their fancy-looking en-suite bathroom, complete with a large whirlpool bath and one of those state-of-the-art shower pods.

“Paul, I think your room is, uh, the one across the hall?” Ashley announced, a weird tone to her voice, like she was trying to keep from laughing about something.

It was the first words she’d spoken to me since we’d arrived at the resort, and I looked down at the key in my hand, the number on the plastic fob sure enough corresponding to door across the hall. Does Ashley know something about my room that I don’t? I wondered, as I left the girls to it, walking the few steps across the hall and fitting my key into the lock.

I turned the handle and felt my heart sink yet further. Because my room looked like it belonged in some totally different hotel. It was small and dingy, with just a tiny window letting in a small shaft of sunlight above a flimsy-looking single cot, the adjoining bathroom containing nothing more than a crummy looking shower and a dirty little washbasin and on the wall next to it, a large rectangular mirror – perhaps the thing in the whole room that was of a decent size.

“Hey, Paul? How’s your room?” Ashley called from the distance in a cruel sing-song voice, and a moment later I heard all three girls burst out in raucous laughter.

That bitch, I thought – not for the first time – as I dumped my bags onto the creaking bed. I knew she’d had a hand in planning this holiday, choosing the resort because apparently it was next to a ‘really cool’ beach. And of course, her father had let her do whatever she wanted, just as long as she had some supervision. But even so, how the hell had she planned it to this level? Was it just bad luck? Or had she actually searched the web until she’d found the one place that had a luxury dorm right next to the world’s worst hotel room?

I shook my head, suspecting that it was just bad luck. Some people got dealt shitty hands, while others like Ashley got all the breaks. But what I didn’t know back then was that my room contained a secret; a secret that would change my life forever …

 

Chapter 2

“Let’s hit the beach!” Ashley exclaimed a short while later.

“Paul? We’re ready, let’s go.”

As I looked up from my place on the uncomfortable bed, where I’d been sulking, fiddling around with my cell-phone, trying to log onto the wifi, the sight that met my eyes still caused a weird lurch in my stomach. Because all three girls were dressed in what looked like the world’s skimpiest bikini tops and matching denim hot shorts. They might have been annoying as hell, but damn, in that moment I felt it fully dawning on me just how hot they were too; all three of them toned and petite, with perky little tits.

“Yeah, uh, gimme a moment,” I croaked, hoping the embarrassing boner that was starting to grow in my pants didn’t show as I jumped up off the bed, ready to accompany them to the beach.

Unlike the girls, I hadn’t changed outfits – still wearing the same jeans and t-shirt I’d worn on the flight, and I grabbed my laptop, stuffing it into its carry case while the girls waited on impatiently, figuring I’d find a patch of shade nearby and get on with some work. I’d never really been much of an outdoorsy guy, and the idea of laying in the sun for hours on end with nothing to do seemed boring as hell.

“Uh, I don’t think there’s plug sockets on the beach, Paul?” Ashley teased.

Back home, I would have immediately shot back some kind of witty reply, but for some reason, outnumbered by the three girls in their skimpy sexy outfits, I just felt my face flush red as I mumbled something boring about having enough battery life to work for a few hours.

Once ready, I followed them out through the resort and down the long dusty path to the beach, trying to keep my eyes off their pert little butts that seemed to wiggle at me, teasing me as they walked, not wanting my half-boner to grow any bigger.

But even though I was trying my hardest to ignore their asses, I couldn’t help but notice that they were wearing thong bikinis beneath their denim hot shorts, the thin strips of colorful fabric poking up from beneath their waistbands. There were signs pointing the way to the beach, with lots of extra writing in various languages I didn’t quite understand. But I could pick out something about perhaps there being a segregated or nudist area or something. And as the path led us closer and closer to the peak of a hill of sand dunes, where I assumed the beach lay beyond, I noticed something else. All the other people who were walking up and down this path were women, and all of them were giving me weird looks, looks I hoped were just to do with the fact that I looked a little out of place in my jeans and laptop.

Finally, I saw another guy, tall and bronzed, clad in only a pair of criminally tight bright red speedos, some kind of lifeguard, I guessed. I sensed the girls murmuring about him as we approached, giggling amongst themselves, obviously checking him out, and he smiled back at them with a set of bright white teeth, his shaggy sun-bleached hair fluttering in the slight breeze at the top of the dunes, as our first glimpse of the beach came into view – and wow. Even though I’d never been much of a beach person, I had to admit, it did look pretty amazing. Pure white sands, sparkling blue water, and an area with loungers and a beach shack that seemed to be serving cocktails, soft upbeat music pumping out from its sound system.

“Hey, women only,” the lifeguard said sternly in a European accent, holding up his palm at me, communicating in no certain terms that he wasn’t going to let me pass.

The girls had already strode right past him and were making their way happily to the beach.

“Wait, what?” I said, still confused.

“You heard,” the lifeguard said, his blue eyes turning cold as he stared me out.

“This whole beach is women’s only. You can’t come on.” I knew there was no use arguing with him.

He was built and strong-looking, way more powerful than me; there was no way I could just push past him.

“Ashley!” I called out, my voice sounding high and pathetic, like a whiny child’s, as I tried to get my stepsister’s attention.

“What’s the problem?” she inquired innocently as she padded back up to where I was standing. But something about her goody-goody act suggested that, just like the hotel rooms, she already knew exactly what was up.

“This whole beach,” I explained, frustrated, “it’s women’s only. I can’t come on.”

“Oh no!” she laughed. “What are you gonna do? I guess you’ll just have to go back to the resort and we’ll see you later then!”

“God damn it,” I sighed, as Ashley’s devious plan came into clearer and clearer focus.

She’d obviously chosen somewhere where I wouldn’t be able to chaperone them, and there was little I could do about it.

“Don’t worry,” she added, “I won’t tell Daddy you fucked up.”

I wrung my fists, the familiar frustration I felt whenever Ashley opened her damn mouth rising up inside me once again. For a start I hadn’t fucked up! I hadn’t chosen this damn beach! I didn’t even want to be here, and I was doing all this just to keep my mom happy. But I knew there was no use arguing with her.

“Just don’t do anything crazy and I’ll see you back at the hotel this evening, I guess,” I sighed.

“See you later, Paul,” she grinned back, before turning and skipping off back down the hill to join Becky and Kelly who, I noticed, had already pushed off their hot pants, their pert little butts now on full display in their matching thong bikinis as they set out their towels on the soft white sand.

“Time to go now, man,” the lifeguard said sternly in his halting European accent.

As I turned and began to head back down the path towards the hotel, I couldn’t get the image of the girl’s cute, sexy bodies out of my head – even Ashley’s. Was that creepy of me? I’d never really seen her in such skimpy clothes before, and I had to admit, she was smoking hot – exactly the kind of girl I’d always secretly lusted over back in high school, but knew I never had a chance with.
Great, I thought to myself with a shake of the head. Now I want to bone my bratty stepsister, as well as throttle her. Can this holiday get any worse?

Chapter 3

After exploring the hotel resort a little, I spent the rest of the afternoon sitting on my bed in my room on my laptop, getting a little work done. I’d managed to figure out the hotel’s wifi system, too, which wasn’t particularly fast but was sufficient for checking emails, Reddit and so forth. And actually, as my frustration at Ashley began to subside, I started to look on the bright side. Okay, so my room was pretty basic, but I wasn’t the one paying for it – the whole holiday had been covered by my stepdad – and if the girls wanted to hang out on some stupid women’s only beach, then so what? It wasn’t like I was her babysitter or anything.

I think Frank just wanted me on the trip to stop her from getting any totally crazy ideas, like bringing boys back to the room or whatever. And in the meantime, I should just enjoy myself – take advantage of my summer break from college. Who knows, perhaps there’d be some cute girl my own age here, who I might have a summer fling with? Yeah, right. Who was I kidding? Girls had never been particularly interested in me, probably due to my plain looks and skinny, androgynous frame.

When there were guys around like that lifeguard, with his tousled blonde locks, toned muscular body, and impressively bulging speedo, why would they give someone like me a second look? I slumped down further on my bed, deciding to knock work on the head for the day and catch up on a little Dr. Who instead.

But before I could even load up the latest episode, my laptop started to flash its battery warning notification –telling me I only had a few minutes left before it shut down. Just like everything else in my room, the plug socket situation was basic at best. In fact, I’d had a quick check earlier and there didn’t even seem to be one anywhere I could see. I’d brought a plug converter with me in my luggage, but I still needed to actually find a plug socket in my room. So I closed my laptop, got off my bed, and started searching my room in earnest, getting more and more frantic, the more it seemed like there simply wasn’t a plug socket anywhere.

“God damn it,” I murmured beneath my breath, as I got down on my hands and knees to check the last place I could think of: beneath the bed. Which was when I saw it. A large black suitcase, pushed right up into the corner. I stayed there for a moment, crouched by the bed, wondering what to do. It had obviously been left by the previous occupant, perhaps accidentally, and I knew the right thing to do would be to just take it to the hotel reception desk and leave it with them to deal with.

But for some reason, another idea started floating through my head. I tentatively reached out and slid the suitcase out from under the bed, uncovering a single plug socket behind it, set right into the corner of the wall. But I barely registered the socket now, my attention fully trained on this mysterious case instead, as I wondered what might be inside it. I lifted it off the floor, surprised at how light it felt, wondering for a moment if perhaps it might be empty inside. But as I moved it up onto the bed, I felt something shifting inside, my curiosity increasing as I started to search for the way to open it.

There was no lock to decipher, no code to crack – just two simple clasps that held it shut. Was I really about to do this? Was I really about to lift the lid off some mysterious suitcase? I paused, looking all around me, even though I was totally alone in the room, my breath held in my chest as I listened for any signs of life nearby. And only then, when I was totally sure I wouldn’t get caught, I reached out and popped open the clasps, and lifted the lid …

 

Chapter 4

At first, stupid as it sounds, I thought I was staring at a dead animal. Because all I could see was a mass of dark black curls. But of course, a second later, I realized it was a wig. A glossy, curly black wig. I tentatively reached out to touch it, registering with a surprise just how real it felt – so real it must have been made for genuine human hair, my fingers stroking through the mass of silky black curls for a moment before I reached in and lifted it onto the bed, wanting to know what else this weird suitcase contained. The next thing that caught my eye was what looked like a silver makeup bag, and I lifted it out and unzipped it. Sure enough, it contained a whole bunch of makeup – mascara, eyeliner, lip gloss, nail polish, and the like. Next to the makeup bag was a black card box, and I lifted the lid to reveal two oval lumps of what looked like pink jelly or silicone, each with a pert little nipple molded onto the top. Fake breasts, I guessed.

There was only one other item in the case, lying at the bottom. Some pieces of black, shiny clothing. With hands that were now shaking a little, I reached in and lifted it out, holding it up before me to inspect it. It was a black one-piece swimming costume, that at first just seemed like any regular women’s one. It was only as I started to inspect it closer, turning it inside out, that the truth became clear. Because it had fitted pockets in the bust, obviously where the fake breasts slotted in to keep them in place. And at the crotch area, there was some kind of formed, molded padding, that I assumed was some kind of attempt to hide your junk and make it look smooth.

I dropped the costume back in the case, feeling a weird mixture of curiosity and disgust running through my veins. What the hell had the previous occupant of this room been getting up to in here?! I thought, quickly slamming the lid of the case closed and clicking the clasps back into place. Again, I considered taking the case to the reception, maybe even complaining. But what if it looked like the case was mine, and I was some kind of pervert who’d come here on a crossdressing holiday and then had second thoughts? What if the girls caught me as I was handing it in? I’d never heard the end of it from Ashley. So instead, I decided to put it back where it belonged, stuffing it deep under my bed once more, pushing it firmly out of my mind as I set about doing what I’d initially intended and finally plugging my laptop in to charge.

But as I climbed back onto the bed and set the episode playing, I found I couldn’t get the thoughts of that suitcase and its previous owner out of my head. They’d no doubt brought all that gear as a way of trying to sneak onto the women’s only beach, probably to creep on all the girls. But would that really work? Would they actually look real enough to pass it off? Probably not.

If anything, they probably got laughed off immediately, their creepy plan going so badly they’d left all their weird, kinky shit behind in disgust at themselves. But what if it had worked? I found myself thinking a moment later. What if they had actually got onto the beach? All those cute sexy girls in their bikinis – some probably even topless or fully nude … Before long, I’d started getting horny, the image of Ashley and her friends tugging off their skimpy little bikinis flashing through my head. Sure, she was a stupid little brat, but she had such a hot body. And so did Becky and Kelly, too.

Man, what I’d give to see them all naked, fooling around together. Again, I paused, listening to the silence of the hotel, checking I was alone, and when I was sure nobody was about to burst in on me, I pushed the laptop off my lap once again and started unbuckling my jeans and tugging open my boxers, freeing my already hard cock, my mind dancing with images of Ashley, Kelly, and Becky – their toned little butts and cute perky tits – as I stroked my dick, closing my eyes, feeling the first rushes of my orgasm already building up inside me. But as I stroked my dick harder and faster, some other thought entered my mind. Because now in my fantasy, I was there with them on the beach – dressed in that weird swimsuit, the long silky hair of the wig tumbling over my shoulders and the fake breasts pushing out from my chest, my cock snug and tight, my face done in full makeup and my legs smooth and hairless, as I lay on a towel, watching my bratty stepsister and her friends frolicking naked in the sand before me.

And it was this final image that stayed fixed in my mind as I came, my orgasm hitting me way more powerfully than I’d expected. I quickly tugged my shirt up around my pecs, just before my cock spurted out a series of thick creamy jets, high up onto my abs, my whole body shivering and quaking. The whole thing had taken me by surprise a little. Normally when I jacked off, it was to the same boring old girl-girl porn I tended towards, the actual moment of orgasm kind of dull and something of a let down.

But this? This had been way more intense, way quicker and hotter than normal. I lay there reeling on my bed afterwards, the gooey load starting to cool on my chest, the image of me dressed up like that amongst the girls still whirling around my head, and even though I knew it was probably wrong, and even though I’d just cum and it should be out of my system now, I felt my mind lingering on it afterwards, starting to toy around with a strange new idea. An idea I just couldn’t shake free no matter how hard I tried …