by D. L. Savage
I’d never live it down.
But even as I was thinking these negative thoughts, another part of me seemed to be taking control, her arm reaching out, her slim hand clasping the door handle and turning it, her hips softly swinging as she strode confidently into the corridor, her smooth hairless legs transporting her down the hall, as if with a mind of their own.
I did as the video suggested, making sure to keep my head up, my shoulders back, and my stomach tucked in, feeling my breasts softly bouncing as I walked, the long hair dancing around my shoulders.
I’d done my makeup, too – it had taken me about an hour, at least, and I’d scrapped it and started again more than once, wanting to get it just perfect. Luckily, I had a lot of good products and brushes to use; the previous owner of that suitcase obviously knew what they were doing, and there was everything I needed to create a natural ‘beach look’ complete with waterproof eyeliner and a lipgloss that gave my lips a really juicy yet natural look.
I couldn’t believe the difference the makeup made! If I’d looked convincing before, then I looked totally stunning now, with subtle contouring around my cheekbones, nose and forehead to give my already feminine features that final touch.
In fact, it was the makeup that had convinced me to go through with my plan. I’d stared at my refection – at the sexy, confident girl in the mirror – and some part of me had known that Ashley would never see through it. She was too dumb, too self-absorbed to think much about anyone except herself.
And now it was time.
Head held high, shoulders back and beach towel clutched under one arm, I swung my hips as I strutted confidently up that same sandy path, where the very same lifeguard was waiting at the top of the hill.
Here goes nothing, I thought as I walked towards him ...
7
“Hey!” the lifeguard smiled as I approached, flashing me a big grin.
I could tell he was checking me out, his eyes quickly looking me up and down, and I found that I was checking him out too, taking in his toned tanned body and that big round bulge in his red speedos in a whole new light.
What the hell am I doing? I thought to myself. He’s a guy and you’re straight …
But somehow it felt different, dressed like this, here in my new feminine disguise, like I was playing the part of some cute, sexy minx, a girl who actually enjoyed male attention. And as I strolled happily past him, I could feel his eyes on my butt, and I gave my hips a naughty little wiggle, the soft sea breeze ruffling my long dark curls, a sweet throbbing ache between my legs as my cock stiffened a little yet stayed totally snug and smooth beneath the tight padded confines of the costume.
As I padded happily down the dunes, I got my first full view of the women’s only beach and holy shit – it was even better than I’d been imagining. There were girls and women of all ages, a lot of them wearing only bikini bottoms, a few even fully nude, just laying around sunbathing, reading magazines, some playing in the surf. And over to my right, just a couple hundred feet away, I made out three tanned teenage girls lying bathing in the sun, topless.
I felt a pang of horny nervousness as I approached, my eyes fixed on them as I drew closer, my cock throbbing harder than ever but still staying snug, as the view got clearer. There they were, lying on their towels, sunning themselves; Becky, Kelly and Ashley, their golden skin glistening from a sheen of sunscreen, their perky little tits on full display.
Ashley’s especially were perfect – even sexier than I’d been imagining. Small and firm, with cute dark nipples that looked like two delicious candies balanced on top.
When I was about twenty feet away, I came to a halt, laying out my towel and sitting down on it, all the while making sure I kept my movements feminine and graceful, my body poised, my back straight, my shoulders back, just like the YouTube tutorial had instructed.
And as I finally placed my butt down on the towel, I felt the tension I’d been holding inside me finally unwind, replaced by a powerful rush of euphoria.
My plan had worked!
I sat for a little while, just watching the girls as they lay tanning. At some point the three of them got to their feet to go paddling in the surf. And as they skipped down to the edge of the water, I checked out their butts in their cute thong bikinis again. But it was the weirdest thing.
Sure, I was still checking them out in the obvious sense, but at the same time I felt a strange pang of envy too. Envy that they could wear even more skimpy clothing than me, envy that their breasts and long hair were real, envy at the plump little pussies they must have between their thighs.
As they began to throw a pink plastic Frisbee to each other, laughing and squealing as the cold seawater danced around their legs, their pert breasts jiggling, I found myself starting to grow tired. Perhaps it was the euphoria of seeing through my devious plan, or maybe it was simply the fact that I’d stayed up practically all damn night learning how to apply makeup, but I felt my eyelids growing heavy.
So after applying a liberal amount of sunscreen on any bare skin, I lay back on my beach towel and allowed my eyes to close ...
I awoke with a jolt, as something hard and plastic bounced off my head.
“Oh my god, I’m so sorry,” a voice called a moment later.
A voice I recognized.
A flash of panic ran through me as I opened my eyes and sat to see Ashley skipping right towards me, bare breasts bouncing, her face fixed in an expression I’d never seen before – one of sincere apology.
Every nerve inside me was jangling now, my whole body poised as I waited to see if she’d see through my disguise. Hell, I’d only planned on watching them from a distance, not getting right up close to them. And Ashley was only a few feet away from me now, close enough for me to see the tiny water droplets on her golden skin and the soft twin bulges of her pussy lips beneath her pink bikini bottoms, not to mention the dark puckered skin of her hard little nipples, which looked no bigger than two pennies.
“I’m really sorry,” she said again, hands on her hips and an apologetic smile on her face.
But there was no hint at all that she recognized me, and I felt my heart leap with excitement again.
“That’s okay,” I replied, in the softest, most feminine voice I could muster, a voice which actually came surprisingly easily. I’d always had a thing for accents, making my buddies laugh as I impersonated various celebrities, but had never tried my hand at a woman’s voice before that moment.
“Oh, cool, you’re American, too!” Ashley grinned. “Where are you from?”
I couldn’t quite believe the transformation in her; she actually seemed warm and friendly, totally unlike the Ashley I’d grown to loathe. It was like I was talking to a completely different person to the spoilt, bratty girl who made my daily life a misery.
“New York,” I said, just blurting out the first thing that came to mind.
“Awesome,” Ashley exclaimed. “I’m from Chicago, but I’m actually gonna be studying at NYU next year! Do you study?”
“I’ve just graduated,” I said with a smile of my own. “I needed a little time to unwind afterwards. And isn’t this the most amazing place?”
I don’t know where the words came from, but they just came spilling out of my mouth, almost like I really was someone else now.
“Sure is,” Ashley grinned, as I finally handed her back the Frisbee, actually a little sad that our conversation was coming to a close.
“So, you’re here on your own?” she said, raising a hand now to her face to shield the sunlight as she looked down at me.
“I was supposed to be coming with my boyfriend,” I said, the words again just rushing up and out of me from some unknown place, “but we broke up just before we were meant to fly. Turns out he was cheating on me with my best friend.”
“Wow, that really sucks,” Ashley said, genuinely sympathetic.
She paused, casting a glance back at Kelly and Becky, then turning to me once more, saying something I never
thought I’d hear in a million years.
“You wanna come and hang out with us for a while?”
Again, I felt my heart begin to pound in my chest.
Talking to her for a few minutes alone was one thing, but could I really hang out with all three girls? That seemed like it would take a whole new level of skill.
But even as I was still debating my decision, I felt my mouth opening and heard the words, “That would be really cool,” come leaping out from between my glossy lips.
“Great,” she grinned. “I’m Ashley by the way.”
“Lisa,” I replied, the name like everything else just springing up fully formed from some weird part of myself I didn’t even know existed …
8
And so that was how I spent the afternoon: hanging out with Ashley, Kelly and Becky on the beach. The girls didn’t suspect a thing, and I found myself concocting a whole elaborate tale of heartbreak and woe, of how my shitty boyfriend Jared cheated on me with my best friend since childhood, Fawn, leaving me alone and heartbroken, days before I was supposed to take this vacation, but deciding to go anyway; the perfect opportunity to take some time out and have a little ‘me time’ as I figured out what to do next with my life.
The girls hung on my every word, offering occasional murmurs of sympathy and encouragement, and I just continued to talk and talk, the lie I span becoming more and more real with each passing second until even I started to believe it a little.
I really did feel more like Lisa right now than boring, plain Paul, and I was actually enjoying their fun, easy company. They seemed so different to the girls I’d travelled here with – smart, funny, compassionate – and I actually started to feel a little bad about how much I’d stereotyped them as ‘brats’, before remembering Ashley’s cruel trick again, which was the whole reason for my disguise in the first place.
“So are you off men totally for a while?” Becky asked, as I came to the conclusion of my tale.
“Oh, I don’t know,” I smiled, “that lifeguard back there could change my mind!”
As before, the words just seemed to leap from my mouth, and the strangest part about what I’d just said was that I meant it. Even though I was surrounded by three smoking hot babes, all topless and dressed in skimpy thong bikinis, it was his body I’d found my mind straying to, the honey gold of his skin, the taut ridges of his muscles, and of course the juicy-looking bulge in his speedo.
“Tell me about it,” Ashley laughed. “He’s fucking hot.”
“You should ask him out for a drink, Lisa,” Becky added, the girls all agreeing with the idea.
I could feel my heart starting to drum in my chest and I quickly shook my head, feeling like this silly little adventure was getting out of control. “I’d love to,” I said, “but I’m leaving tomorrow, first thing.”
“Perfect,” Kelly giggled. “One night of passion and then boom, gone in the morning!”
“One night stands are so fun,” Ashley added. “You can be totally slutty and not have to worry about the consequences.”
“I’m not that kind of girl,” I said, just wishing they’d change the subject, while at the same time the image of my bratty stepsister being totally slutty with some total stranger sent a charge of excitement between my legs, my cock swelling and straining against its padding.
“You mean you’ve never had a one night stand?” Becky gasped.
I shook my head, feeling a blush rising to my cheeks as all three girls looked at me incredulously.
“No,” I murmured, my head spinning, “Jared was my first ...”
And the thing was, it was true. Not the Jared part, obviously, but the one-night-stand thing. As Paul, I’d only had a couple of girlfriends, that whole sleeping around lifestyle somehow eluding me all through college, much to my frustration.
“And anyway, I’m shy,” I added. “I’d never have the guts to ask him out.”
“Oh, it’s on!” Ashley announced decisively. “Don’t worry, we’ll do all the work. You just meet us at Cheetas, this cool cocktail bar we found last night at ... nine o clock? And we’ll do the rest. You’re gonna have so much fun, Lisa!”
“How do you even know he’s single?” I muttered, just wishing this whole stupid episode would be over.
“A guy like that?” Ashley giggled. “Of course he’s single. I mean, if you were a guy, would you work at a place like this with a girlfriend?”
“I suppose not,” I said.
“So you’ll come?” Ashley persisted, her head tilting and her pretty blue eyes growing wide in that puppy dog expression I always saw her pulling on her dad.
“Sure,” I smiled, unable to resist.
“Awesome!” the girls all exclaimed excitedly.
“Anyway, it’s been fun but I’d better go back to my room and get ready for tonight,” I said quickly, deciding it was time to call a stop to this nonsense, once and for all.
But as I pushed myself up to my feet, Ashley said, “Yeah, I guess we should too. You’re staying at the hotel, right? We’ll walk back with you ...”
“Great,” I croaked, wondering how the hell I was going to get out of this.
And as I got to my feet, I almost forgot to move in the graceful, feminine way I’d practiced, just lumbering up for a moment, before remembering with a heart-stopping flash of terror and quickly correcting my movements. But luckily none of the girls had noticed, all too busy putting their bikini tops and hot shorts back on.
Once they were dressed, we gathered up our stuff and made the slow walk back up the dunes, where I could already see the lifeguard waiting, my nervousness increasing with each step we took, until I was practically trembling by the time we reached him.
“Hey!” Ashley called out to him, a flirtatious tone to her voice. “How’s it going?”
“Hello ladies, I’m good thank you,” he replied in his soft European accent, giving us all another flash of his dazzling white teeth, and I felt my gaze roving over his toned tanned body, despite myself, my bound-up cock throbbing and aching between my legs, the way I imagined a clit might, as my eyes flicked – just for a half-second – down to that large round bulge between his muscular thighs, before I quickly pulled myself back together again. “Did you have fun on the beach?”
“Sure did,” Ashley beamed, pushing her chest out a little, obviously enjoying flirting with him. “Say, it’s my friend Lisa’s last night here and we were going out for some goodbye drinks at Cheetas. You wanna join us?”
At this, everyone turned to look at me, including our sexy lifeguard, and I felt my blush increasing and the almost deafening boom of my heart in my ears.
“Sure, that’d be fun,” he grinned, again checking me out, just like he had done when I first arrived, an unmistakable flash of hunger in his big blue eyes.
“I think he likes you,” Becky murmured in my ear, taking my arm and gripping it a little excitedly.
“Cool,” Ashley said, turning to leave. “We’ll be there at nine!” she called over her shoulder.
“Looking forward to it!” he called back as we all headed off back to the hotel.
“See?” Ashley said to me with a proud smile. “Easy as pie. He’s yours.”
I didn’t know how to reply, and I just fell into stunned silence as the girls chattered around me, all of them talking about what they were gonna wear tonight. I knew I wasn’t actually going to go, and I felt my heart sink a little, knowing the fun was well and truly over. I even found myself getting jealous of them again, and wishing I too was a real girl – a girl who actually could go out tonight.
I was still puzzling about how the hell I was going to shake them off and get back to my room safely, when I saw my way out, just as we approached the resort.
“My room is this way,” I said, pointing to a hallway that led off to some apartments on the other side of the complex.
“Cool,” Ashley smiled back. “It was great to meet you, Lisa. And see you tonight!”
“Yeah, see you tonight
,” I replied, as the girls all waved and grinned at me, then headed back to their room.
I turned and walked away from them until I’d turned a corner, then just stood there, leaning against the wall, my head spinning and my heart drumming, marveling at the fact that I’d actually got away with my crazy plan. I’d taken it way further than I’d ever dreamed, but actually – it had gone pretty well.
I’d even enjoyed myself, and for just a little while back there, I truly had felt like one of the girls.
All I needed to do now was get back safely to my room and this whole crazy adventure would be over.
I hung around in the shadows of the corridor for the longest time, until I was totally sure that the girls would be back in their room, and then I slunk out again, padding on tiptoes down the corridor that led to my room, my heart drumming and my breath clutched in my lungs as I snuck past their door, hearing their happy voices chattering away inside.
My hands were shaking as I fumbled the key into the lock, then opened the door, and then finally I was inside, closing the door behind me, the adrenaline coursing through my veins.
Still trembling a little from the excitement, I quickly began to undress, tugging off the wig and swimsuit, bundling them into the suitcase which still lay open on the bed.
All I needed to do now was remove the makeup.
Which was perfect, because what I needed more than anything was a cold shower.
9
I could hear the girls getting ready in their room. One of them was blasting out pop music from a cellphone or laptop, and even from my place across the corridor, lying on my bed, I could sense the growing excitement of a fun night out building in the air. But so what?
I wasn’t going with them, was I?
I felt a sharp pang of frustration mixed with envy, as I imagined them primping and preening in front of the mirror – fixing their hair, doing their makeup, making themselves all pretty and sexy.
They were so fucking lucky.
