Dream Girl Pt. 01

Her jaw bounced for a bit before finally assembling some words.

"You look.... GORGEOUS!" she squealed, springing up and giving him a long hug, breasts squeezed into his chest, and Steph's cheeks were like two radishes as he eagerly wrapped his arms around her.

It was too short and sweet, because she quickly pulled back from his embrace, feverish with excitement.

"Honestly, this is like, PERFECT... That ass, it's like.... You're HOT!" she said, checking out each and every angle of his body as he tried not to let his excitement get the better of him.

She smacked his ass and gasped as it rippled, not noticing his instinctive moan because she was too busy watching the buns jiggle.

"Oh my GOD your ASS!!! Hey you know what? We should totally do a double date! I've never been able to do one before, and I just know the guys would love it!"

He coughed in surprise, trying not to show his discomfort.

"Excuse me, but there is zero chance I'd ever go on a date with those guys."

"Aw, come on Stephanie, I've never had a girlfriend before!"

"Well, why do we need men then?" he asked in a moment of inspiration.

She giggled.

"Oh, you are funny Stephanie."

The next hour or so was spent tanning, splashing each other in the pool and laughing a lot. Grace relaxed around 'Stephanie' to the point where she even removed her top to get a full tan on her chest. Steph gazed, mesmerised by her luscious pears as she settled back, nipples peeking from the white mounds as she closed her eyes.

After far too long staring he began to feel guilty and tore his gaze away, lying forwards on the tanning bed to explore the combination of sun and lace on his skin.

Steph couldn't help enjoying the bikini material on his body; in fact, he was loving how the bottoms wedged into his crack, and wondered if Grace had any spare thongs, before feeling deeply troubled at having even considered it. The reflection staring back at him whenever he went near the pool was so hot, and he imagined what the girl in the yellow bikini would look like sucking a big cock like in the porn films he had seen, slutty lips choking on a big black stick, before he remembered he was the girl and shivered, forcing the images from his mind. It was quite tricky trying to tan his back whilst keeping his hips up to stop his erection pressing into the sun bed and dribbling cum on his towel.

After an afternoon spent splashing around, tanning and admiring Steph's booty, they sauntered inside as the sun crawled towards the tropical skyline.

"Well, I think it's time for the next part of our bet," she said slyly.

"Oh yeah?"

'Would this be the time to kiss? Okay it might be weird with me in a bikini but...'

"Yeah.... It's DRESSUP TIME!" she yelled, and Steph's face fell, unnoticed by Grace who was dragging him up the stairs to her room with the full intention of doing whatever she wanted to him, which in any other scenario would have been exactly the plan.

"I think red for you... I mean lady in red right?! Stephanie's a passionate woman...."

He couldn't help feeling like a barbie doll, something Grace could mould the way she wanted. It was humiliating, and he drew the line at her ordering him to get naked in front of her.

"What? No, I'm not stripping off in front of you."

"But we're girlfriends Stephanie!"

He glowered at her.

"No."

She sighed but relented.

"Okay... well.... Take this dress, these panties and this bra, keep the wig because it looks perfect, and maybe some heels as well.... We should go the whole hog right?!"

She was so brazen and overcome with excitement that he couldn't say no, and miserably allowed himself to be forced into the bathroom to put on his outfit for the evening.

"How could you let this happen," he muttered to himself in the mirror, before a flutter of excitement hit him when he saw the sexy girl talking to him.

"Jesus, get a grip," he muttered, although his spirits were significantly lifted as he stepped out of his bikini and took the silk panties, riding them high between his cheeks. He loved how slutty they were; even with his tiny little bulge at the front, it really showed off his perks.

He wiggled his tush like he needed a good spanking and tittered.

'Stop it, just put the clothes on', a voice in his head said, and he managed to pull his eyes away from his girly butt long enough to slip on the push-up bra and red dress which rode tantalisingly high up on his thighs.

'Wow, I'd fuck me', he thought to himself as he did a whirl around.

He looked like a girl dressed for one thing: to find and wrap her lips around a thick cock (strangely no matter how hard he tried, he couldn't imagine the cock as anything other than black).

"Oh, the heels!" he whispered excitedly, grabbing them from the floor and slipping them on.

'Wow.... Now I know why girls wear these... I feel so much taller!'

He couldn't believe the stream of thoughts running through his head, but it would be a sad occasion when he had to change back into boys' clothes... he'd gone from a worthless virgin to a sexy, gorgeous blond in twenty minutes!

After a few minutes of staring and daydreaming the bathroom door swung open and Steph turned round in shock, because he had been so focused on his appearance and imagining wicked scenarios between himself and tall, black men that he was hard as a rock. Grace was standing in the doorway wearing a black mini-dress, and her eyes lit up.

"Oh wow," she breathed, and Steph whimpered as he covered up the tiny tent in his lap.

"Hey, can you.... Just wait a bit," he uttered in a strangled sort of voice.

"Sure thing," she grinned, although the eagerness in her eyes was extremely worrying, not helped by the sly wink as she closed the door.

Steph grimaced, thoroughly confused with the turn this week was taking. 'I want to be Grace's boyfriend, not her girlfriend!', he thought anxiously, curling his long blond hair in frustration.

He should stop thinking about big black dicks too...

Steph shook his head and waited for his erection to go down whilst idly glancing over the mascara and eyeliners littering the sink.

'Hmmm...'

He picked up a bottle and checked his complexion. Maybe.... Maybe he could use a little definition to bring out his eyes?

Before it had sunk in what he was doing Steph was applying black liquid to his lashes, careful to keep it away from other parts of his face. It was painstaking, but Steph found his concentration becoming keener, enjoying the way the lashes made his gaze seem more vibrant.

By the time he had finished there wasn't a second thought as he grabbed the eyeliner, lipstick and brush whilst checking his phone for a full makeup guide... He wasn't quite sure how to make up his face completely but something inside was firing passionately to complete the look, and after some careful attempts he managed to get a nice depth to the eyes which now gleamed beneath long, fluttery lashes and sultry contours of his more feminine face.

It felt like he was sculpting rather than painting, bringing out features that were already there, hidden within the delicate lines of his face. The sharp eyebrows were darkened, his cheeks becoming a little rosier...

Finally, with a thrill of excitement, he realised the last thing he needed was lipstick, and picked out a cherry red. He found he didn't even need to go over the edges to make his lips look bigger... they were already whore-like to begin with, he thought with a swell of pride in his breast. He gave himself a long kiss in the mirror and made sure it was evenly applied.

The girl staring back at him was so sultry and flirtatious that he found himself feeling profoundly nervous to even think about approaching her, despite the fact it was just himself in the mirror.

He then had a realisation that if he really were the girl in the mirror, he would have wanted nothing to do with the pathetic boy that had been standing there earlier.

'So this is what hot girls feel when they look at guys like me.... Why would I want a worthless boy like that?... Look at me! I only get fucked by real men.'

His whole presence lurched as he tried to take back the thought 'I only fuck real men' and pretended it hadn't happened, hands shaking as he brushed back a blond streak which had fallen to the front of his shoulders.

The door seemed much heavier as he pulled it open and emerged, firmly into the light of the bedroom.

Grace looked up from picking out handbags and screamed.

"OH MY GOD STEPHANIEEEEEEE!"

She leapt up and grabbed Steph, beginning to dance in a circle with him, bounding with energy.

"LOOK AT YOU, OH MY GOD YOU'RE THE SEXIEST GIRL ALIVE, YOU FIIIIINE BITCH!" she sang gleefully.

"Yeah.. sure," murmured Steph, uncomfortable with how she was talking to him but also enjoying how soft her hands felt in his.

Her voice was breathless as she proceeded to look over every inch of Steph.

"Those LIPS babe, oh my..... I just can't get enough of that ass..... you're gonna slay tonight!.."

She stopped at his fingers.

"Erm, Stephanie, you missed something," she said knowingly, fluttering her pink nails at him.

"Oh, sorry," he mumbled. "I don't know how..."

She burst out laughing.

"I KNOW you don't babe, but don't worry, your saviour is here," she said fawning over him as she led Steph to a makeup table with nail polish and a bunch of other items that Steph had never seen.

"Cherry, cherry, cherry," she muttered, searching it.

"AH!"

She snatched the bottle and placed it on the table.

"Sit," she ordered.

He did so, and Steph was subjected to a torturous hour which felt like longer as Grace coloured the nails on his hands and feet whilst discussing 'girl problems', his 'perfect boyfriend', and the recent goings on in her favourite girly trash TV shows, all whilst absent-mindedly touching him across his body, putting a hand on his leg to steady herself, a stroke of his arm as she focused on a particularly tricky bit.... It ended up leaving Steph with a throbbing hard-on as she finally finished, plus a spectacular set of red nails on his hands and feet.

"Perfect!" she squealed.

Steph's lukewarm "thanks Grace," was cut off by three booming knocks from the front door.

"Oh, the guys have arrived!"

'Fuck.'

She whipped the bedroom door open, looking exhilarated.

"Come on, let's go down and greet them!"

"Oh Grace no, please don't make me.... "

But Grace was positively beaming at the thought of showing Stephanie off to Andres and Dee.

"Oh come on, it'll be great. You said you were adventurous right?"

Her eyes were shining.

'Adventurous... that would be another tick in Grace's perfect boyfriend column....'

"Just.... FINE, okay!"

She grinned.

"Hell yeah sister!"

She grabbed his hand before he could protest at being called 'sister,' and skittered down the stairs, trying not to trip in their heels, and both scandalously dressed figures began laughing as they threw each other off balance through the hallway.

'Like a couple? Or two girlfriends...' Steph was no longer certain.

"Oh and babe, just make sure to do your sexiest pose when the guys first see us!"

"Shut up," he said, still heated from the intimacy and bustling.

She stopped for a moment and faced him with a genuine smile.

"You know... you seem happier than I've ever seen you."

Steph looked deep into his soulmate's eyes and worry filled his stomach.

"Ah... really?"

She nodded, and he tried to hide the anxiety that her comment had caused as she did a sultry turn to the door.

"Okay, ready?"

Steph smirked, pouting his sticky red lips towards the entrance, and threw his hips to the side.

Grace giggled, and unlatched the door.

Andres and Dee were revealed, both dressed to the nines in white suits with black shirts, sleek shoes and golden sunglasses. They seemed, in a word, imperious.

Steph was stunned. The guys looked even more imposing than yesterday... and nobody had mentioned suits. It looked like they were ready to hit the club with their bitches in tow. Steph's heart began beating a hell of a lot faster as his eyes snapped directly to Andres' crotch, searching for the subtle swell running tantalisingly down the leg, before wandering upwards to his cock-sure expression. Andres seemed to be observing Steph's new outfit, although it was kind of hard to tell if he liked it behind the glasses.

"Hey ladies," smiled Dee, who strolled in.

Andres walked up to Steph and slapped him on the ass.

Steph mewled and adjusted his dress so they wouldn't see his excitement rising as he rubbed where Andres had spanked him.

"So," smiled Dee, "Where do we want to go?"

Grace chimed in immediately.

"There's only one place we can go if we all look this good...."

"Wait, surely we're not..." Steph tried to interject, but Grace's excitement was feverish.

"White Ribbon!!"

The guys both nodded in agreement.

"Sounds good," said Dee. "Seeing as that was such a sweet idea, you may kiss the ring, girl."

Steph clenched his fists as he watched Grace simper and peck the man's golden ring, and his voice cracked slightly as he spoke. Everybody else smirked as he began subconsciously speaking in a higher, more girly pitch.

"Guys, I hate to interject, but you may have noticed I'm-....."

"Beautiful," said Andres, eyeing him up and down. "You're definitely my bitch tonight."

Steph felt his face growing hot.

"I... I don't..."

"I'm gonna treat you like a good girl tonight Stephanie."

A thrill ran through him. Well, two could play at that game. For once on this holiday, he wasn't going to be outcooled.

He adjusted his dress so that it fully played across his body, accentuating his subtle curves, and cocked his hips to the side so his ass was almost exploding out of it.

"Why thank you babe," he responded, throwing a kiss in the air.

Grace and Dee were both dumbstruck by Stephanie's change in visage, Grace in particular was mesmerised, staring at the way Steph was angling his body. Andres didn't say anything, but he.... Rippled. Like a tiger setting itself to attack mode, the mood shifted.

Before Steph could think Andres had closed the space, and the tangy musk of his cologne stung Steph's nostrils, so much so that he could almost taste it. It was not unpleasant at all, with hints of what smelt like palm trees and coconut, mixed with something else.... His large, dark lips were so close... that chest....

Steph froze, quivering as brand-new hormones coursed through his body, his brain screaming signals that didn't make sense, counteracting each other, so he continued to hold his sultry pose, and even brought his lips to Andres' cheek.

"Like what you see?" he murmured.

'What am I doing?!'

Andres spoke in a whisper.

"Hell yeah girl... Come with me."

This nudged Steph back towards reality, and he choked slightly.

"Andres, h-hang on, wait I can't g-ooOOOGHHH!"

He didn't have time to react, because Andres had picked him up and slung him over his shoulder, heels waggling in the air as he was unceremoniously lofted out of the door and into the cool evening air.

"Time to go ladies!" Andres chuckled, as the others tittered in the doorway.

"Andres!" Steph chided. It was frustrating how easily he had been picked up, but his heart was still pounding from the smell of the man's cologne, and besides, they hadn't even made fun of him for being in a dress, in fact they seemed to like it! Most jock guys would have crucified him for that..

"O-Okay, you can stop now," tittered Steph nervously.

The response was a meaty spank on his ass, which made him blurt out in shock.

"UGH!"

"You will call me Daddy."

"Stop it Andres, seriously!" he moaned, but Andres simply thwacked his open palm against the jiggling globes, which were completely unprotected by the thin satin material pulled tight across his skin. It was surprising how good it felt being aggressively touched by strong hands.

"Okay, that's...OH!" Another *SMACK*, and Steph was moaning now as Andres slapped his ass every few steps, all the way to the waiting limousine. By the time they were there Steph had stopped struggling, and was moaning each time that giant hand connected with his raw behind.

"Shit," he murmured as one last broad stroke found its mark, and then he was being let down, one hand tight on his butt. Andres didn't let go, sliding a thumb tantalisingly up Steph's crack which sent a ripple of pleasure and fear up his spine, before resting at his lower back.

"What's my name," Andres said, those lips so close to Steph's cheek.

"Daddy," he whispered, and the hand gave a squeeze as Andres slid down and pushed his rump past the stripper pole in the centre of the limo and into the corner, next to what looked like a drinks cabinet. This was followed by Andres himself entering and sitting next him, taking up nearly a third of Steph's seat, forcing his side against the man's powerful body.

Steph's mouth opened and closed like a goldfish as he saw the difference between their thighs.....

'Both my thighs could fit into one of his trouser legs.....'

It looked like a father was taking his daughter to school, except for the shocking contrast between Steph's pale, snowy complexion and Andres' deep ebony. The man's hand slid onto Steph's leg in a way that made it clear he was enjoying Steph's new demure countenance.

Steph's heart was thumping in his chest, and he was having trouble swallowing because so much saliva was now being produced in his mouth he was close to drooling.

'Relax... he's messing around, you're not into him, you're just excited, take a breath.'

Steph adjusted his red butt-cheeks. He was okay..... Andres was just screwing with him, and even if he did go to the club as a girl, no one would work out he's a dude. At this point Grace skipped out of the front entrance hand in hand with Dee, making Steph's brain plummet into his stomach. Her hand was not visible, encased inside the huge bear trap, and she had a tiny black handbag on her shoulder with another red one swinging from her free hand.

"Here Stephanie," she smiled, proffering it as she ducked in through the limousine door.

"Thanks," he mumbled.

"You're welcome sister" she said, sitting on the seat opposite with her legs crossed innocently in that way that still made her so perfect in Steph's eyes.

Dee made his way in after her, and something triggered him seeing how close Dee sat next to her.

"Okay stop now guys... this is really funny but I actually don't want to-"

Dee cut in.

"You don't want to let everyone enjoy their holiday?"

'You mean I don't want to let you steal the girl of my dreams!' he spat in his head.

"That's not what I meant...."

Andres smoothly cut across him again.

"We paid for both of your tickets, your Villa.... But it's cool, we can take you both to the airport now if you'd like? I'm sure there'll be no problem if you want to fly back looking like that."

Stephanie's cheeks went as red as his ass felt, and Grace's face fell in a way that broke his heart.

"Okay... okay fine.... look at least let me get changed!"

Andres sniggered.

"You should have thought about that before you dolled up bitch, besides we don't buy drinks for dudes. You're a pretty girl on a night out with everything paid for, why complain? You have to understand, that dude Steph ain't riding anywhere in a limo."

Steph tittered.

"But I'M-"

"Stephanie," interjected Grace. Her eyes were wide in a 'don't ruin it' kind of way.

"Your name is Stephanie."

Steph shrunk, visibly cowed in the corner. He had not expected Grace to openly admonish him. For the first time since he had been here, Steph felt a gap opening between the two of them.