Dream Girl Pt. 02

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Get the girl... or become a girl for BBC.
23.4k words
4.73
49.5k
116

Part 2 of the 2 part series

Updated 06/10/2023
Created 08/02/2021
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Hi all

I know a lot of you were clamouring for this second chapter, so here it is!

Hope you all enjoy - TSG123 x

-

"Hey, good morning stranger! Or should I say, afternoon."

Steph hobbled down the stairs, and as he did his full look came into view.

"Oh Wooww, look at you babe!" gleamed Grace.

Steph's skin was crawling, and he wanted desperately to go back up to his room and change, but the only thing Andres had allowed him to wear was....

He didn't want to think about it

"You look so hot, like I would totally fuck you," giggled GRACE, fawning over the huge 'BIG DADDY' t-shirt that Andres had lent him, and nothing else.

He threw her a poor attempt at a smile.

"Hang on, are you wearing any...?"

She looked down slyly, bending to check under his T-shirt, and Steph whined, pulling the shirt lower, crouching down.

"Oh my God!" she crowed.

It looked like Christmas had come early for Grace, as she cupped her hands to the side of her mouth so Dee couldn't see.

'Did you...?' she mouthed, and mimed two fingers going through a large ring.

Steph shook his head violently, going white.

"No... no just I..... I didn't have a place to sleep," he said quickly, "so Andres lent me his stuff, and... and let me sleep in his bed."

"My room was open," she said, peering at him with a knowing grin.

Steph's legs quivered with each step after last night's pounding, and he realised with a horrendous flip of his stomach that something was trickling down his inside leg.

"I... was drunk," he said in a high-pitched voice, pacing over to make some toast, subtly manoeuvring to wipe some of Daddy's jizz from between his legs as he reached for the bread.

"I'll have some as well sis," said Grace casually.

"I'm not your sis."

"Well if you're not my sis, I guess I won't tell you that someone re-arranged your face last night."

He froze.

Steph hadn't looked in the mirror this morning, and had completely forgotten about the makeup.

He went to check his reflection in the silver fridge and nearly screamed.

Even though the surface wasn't completely reflective he could see he was an absolute mess. His hair was everywhere, mascara had run all over his cheeks, and it looked like he had been profusely making out with someone all night as bright-red lipstick was now spread across his face in the most whore-like manner imaginable.

"Were you getting into character..... Stephanie?" asked Grace teasingly.

Steph's forehead burned as he threw bread in the toaster and opened the tap to full, drowning his face in water as if it could wash away what he had done last night in the process.

A few tissues managed to wipe away most of the offending substances, although the mascara was still thick around his eyes.

"No, I was drunk, and... I must have wiped it on my pillow," he lied, not able to bring his eyes to meet hers.

"On Andres' pillow?" Grace asked casually, grinning, and Steph for the first time felt genuine anger at Grace.

"Nothing happened!" he snapped.

"Sorry... it just seems like you enjoyed your night," she said pointedly, taking a bite of her toast.

"No, I didn't."

"You sure? I could have sworn that you were enjoying 'Daddy' in the limousine.."

"Shut up!" he spat, and they fell into silence, Steph eating his toast quickly so he could go somewhere and try not to think about the soreness of his asshole.

After barely a minute he finally managed to squeeze the last piece of toast into his mouth, swallowing with a long glug of water.

"Bhhy." he mumbled with his mouth full before walking carefully to the stairs holding the back of his shirt as far below his ass as he could.

***

'Fuck.'

Each step made his thighs ache, having been stretched into so many new positions last night.

'Don't think about how he destroyed me.'

He whined as he sped up, limping to his bedroom door.

Still locked.

'Come on.... Please.....'.

He tugged at the handle, desperate for somewhere to feel safe from the humiliation lodged in his chest, and in a fit of pique he shrieked and slammed the door with his foot.

"OW!.. ow ow ow...."

His toe hurt like hell, and now he needed to wipe away a new batch of cum leaking down his thighs, that and try to forget the knowledge that he'd lost his virginity to a man last night.

Steph began to sob, limping into Grace's bathroom because it was the one place he could go that nobody would follow, and when he locked the door he fell back against it and cried.

Tears ran down his cheeks, hot and wet, and cathartic. After a few moments of blubbering he took some tissue paper and tenderly wiped away the white splooge leaking from his anus and flushed it away.

'Best holiday ever.....'

The thought made him chuckle absurdly.

'Wow, if I could have told myself what was going to happen on this holiday, I would have run a mile, screw Grace, screw Andres.... screw it all.'

He put his head in his hands and breathed.

'Just... take it slow.'

He decided to take a shower to try and cleanse himself, wipe everything away.

Stepping in and turning the heat up, he flinched as the hot water hit his forehead, steam rising as he began to rub away the last vestiges of last night's shame (at least, on the outside).

The feeling of Andres' thick cock sitting in his rim, stretching it wide, crept into his head as the heat of the water spread cathartically on his skin.

'The way he kissed me.... Pulling my panties aside.....'

All too quickly he had wrapped two fingers around his penis and begun jerking, and his high-pitched moans were just like a girl's as he fired a few long ropes of cum over the frosted glass.

"Fuck," he murmured, staring at the lines painted across the surface before wiping away the evidence as quickly as possible, his head burning again as he turned the shower off and towelled himself down.

Clothes.

Huffing, he put Andres' shirt back on and opened the door. Grace was still downstairs... at least she'd given him some time alone, which he was grateful for.

'Maybe I could ask Daddy for clothes.'

He felt physically ill at having automatically thought of Andres as Daddy, resolving to be stronger.

'I'm a man. I am on holiday with my future girlfriend, that guy just tricked me with alcohol. Never again.'

Now, clothes.

He searched around the room for anything that might work.

'Jesus, does she have one pair of underwear that isn't lace or silk panties!?'

His eyes passed dozens of them, red with delicate embroideries down the sides, frilly white numbers, purple ones composed mostly of stylised gaps in the material....

'Ooooh....'

He stopped at two sets of garter belts and stockings, one black, one white. He had always had a thing for girls wearing these.... Somehow just seeing them was enough to put him on edge....

'NO, just find a normal pair!'

Begrudgingly he placed the set of underwear carefully on the bed and continued his search.

Thong, more panties.... bikini bottoms.... Wow, that's it!

'What the hell Grace... Maybe I could just go commando?'

The thought of more cum leaking down his legs was enough to dissuade him of that notion.

'Guess I'm going to have to pick....'

His eyes roved over the treasure trove of slut-wear. They stopped on the black garters.

'They look soft...'

Before he could understand why he was doing it, Andres' shirt was off and Steph was sliding the lace stockings up his legs.

'And they feel soft....'

It was like his body knew what to do even as a tiny part of his brain hated him for it, but the stockings were soon clipped to the garter belt, and without hesitating he attached the accompanying bra firmly to his front. It was a shame they weren't push-up, but his body otherwise looked sensational, his legs good enough to salivate over. He looked like a playboy cover girl. He flashed his ass to the mirror and pouted, wishing he had his lengthened hair back. If he put makeup on he could look very convincing regardless, now he had caught the bug.......

'For now, I'm still a guy. Kind of.'

Steph pulled out a pair of Grace's jeans and managed to fit them on, moulded to his ass and legs, and a blouse that kind of looked close to a shirt. There were t-shirts in there, but he was enjoying how good the garter belt felt that the blouse needed to be tried out.

He looked in the mirror and found himself looking quite delicate, which pleased him.

'I'm strong enough to show my feminine side.... Yeah, I'm a strong man... inside.'

Calling himself a man didn't feel as comfortable as he had thought it would, smiling as he enjoyed the cuteness on show.

'I'm a bad bitch.'

Then he noticed the makeup arrayed on the bathroom counter.

'Well... if I'm going to be Stephanie again today.... I won't do this ever again right? Maybe I should make the most of it...'

He paused, caught between his fragile masculinity, and the heat building in his body.

'I'm on holiday. I should be able to enjoy myself!'

Steph sashayed into the bathroom.

***

"Hey,"

Grace looked up from the L-shaped sofa, and gave a huge smile as the girl-next-door figure made her way gingerly down the stairs.

"Oh DAMN!.... How are we my 'not-sis'?"

Steph hobbled down a step at a time as she eyed up the ass-squeezing jeans, pink tank top and girl-next-door prettiness.

"Shut up, the guys expect this..."

"They never told you to look like a hot piece of ass though!" she said, fighting back laughter as Steph settled down next to her gingerly on the couch.

Steph's cheeks went nearly as red as the bright, glossy lipstick he was wearing, the same barbie pink as the top.

"Well I don't have clothes...."

"Yeah," said Grace mockingly, "And I guess you couldn't reach your makeup either... First world problems am I right?"

Steph felt anger rising in his chest and he turned away from the girl who had got him in this mess in the first place.

"Look, I'm just getting through this, it's YOUR FAULT I'm here with those... those.... Dicks," he finished lamely, remembering Daddy's specifically, swallowing some saliva.

Grace raised her eyebrows, lazily swinging one leg over the side of the sofa.

"Okay, you're right, sorry... but I mean come on, last night was fun, right?"

Steph thought it best not to respond, but he couldn't help enjoying the memory of being sat on Andres' lap, or being picked up and carried.... of being fucked by a huge black cock.

'No Steph, stop THINKING about it!'

"Uh yeah ha... it was kinda fun..."

"Right?! I mean the Limo, the dress up, the atmosphere..."

"Yeah.. yeah it was pretty cool."

Grace snuggled closer, placing a hand on his knee.

"And it was even better because you were with me."

His chest warmed as she squeezed his knee.

"Ha yeah..."

She moved closer.

"And I don't want to piss you off but... you actually do look hot, hell I would totally kiss you!"

"Yeah?... well... you still owe me one kiss.... From yesterday..."

She toyed with her hair.

"Oh.. the bet...yeah... I guess I do!"

She scooted up to the point where their legs were pressed against each other, and suddenly the room was very warm.

"I've never had a lesbian kiss before," she whispered with a grin.

Steph wasn't sure about the wording, but it didn't matter as she moved her lips closer, her voice a light breeze, barely touching the edge of his ear.

"We could do it now... Shame, if we were drunk who knows what might happen?" she giggled as they closed in.

His chest was heaving, blood flowing to his crotch.

"What.. might happen?"

"Well, I mean probably nothing, you know...."

"A-Actually... I'd like to keep my kiss for later!" he blurted.

She paused, confused, inches away from him.

There was a tiny dimple in her left cheek which he could just about make out this close to her. He wanted to brush it with his lips.

"Oh.. really?"

"Yeah," he said fervently, "now is uh... not the right time yet.... gotta get into character... Stephanie.. you know, if it's a-uh.... lesbian kiss."

"Right," she said, eyeing him carefully.

Steph tried to cool his arousal, placing his hands on his belly as he tried not to imagine him and Grace drunk and removing each other's clothes. For some reason in his head they were both wearing stockings and garters just like the ones he had on at that very moment.

"So uh...... What's the plan for today? Wanna go to the mall?"

"Oh uh... Sorry Steph, I was actually going to go with Dee to the beach."

His insides turned into a swamp-like sludge.

"Oh... cool..."

"Yeah... he wanted to show me somewhere, just the two of us... But it's okay because he said Andres could keep you company while we're away!"

Now it felt like his insides were exploding.

"Ah, no worries... yeah."

"Is... is that okay?"

He tried to pass off his gut-wrenching nerves with a simple nod, jerking his head like he was being puppeteered by an orangutang.

"Absolutely! Of course... Sounds great."

"Cool."

She gifted him a smile that made his soul ache.

"It's fine though... because we can still get you looking perfect while Daddy is asleep!"

Steph's whole body felt like it was being stretched on a torture rack.

"Yeah... just perfect," he muttered.

***

"You sure you don't need me to come along...?"

"No, we'll be fine," smiled Grace, stepping into the taxi.

Dee leaned in close enough that Steph could feel the impeccable minty freshness of his breath.

"Have fun, Stephanie."

A large hand came down and spanked him, and Steph whooped like a girl, just catching himself from falling over, ass-cheek burning where the man had struck him.

"UUHN!"

By the time he had got his bearings, red-faced and huffing, the taxi was already reversing.

"SEEYA LATERR!!!" whooped Grace through the open window as it sped off, towards the beach, Dee's infuriating smile beside her as his arm came over her shoulder.

"Bye," uttered Steph, standing crestfallen on his own, ruffling the hem of his blouse with long nails.

He hadn't expected them to look so good, but the pink nails, top and lipstick combined to make him feel stunning, and they softened the blow of being left with..... Andres.

The dust plumes fell to the ground as the car wound its way down the long entrance, and then it was gone. Steph was struck by the thought that he needed to find a way of wooing her fast, if he was going to remain in competition with Dee.

'Maybe I could get her a gift... for when she comes back?'

After standing in place for what felt like an hour, he turned back to the villa, silent like a house of horrors. Somewhere inside was Andres... He had heard him getting a late breakfast whilst Grace was giving Steph the full salon experience in her room, which included plenty of nattering and gossiping. Luckily he had so far managed to avoid him.

But now... it would just be the two of them.

Steph wished with all his heart that he could run to his room, but that sounded awful, staying in a single room whilst not enjoying the rest of the huge, lavish villa, and the tropical island on which it stood.

Then the thought came to him:

'Fuck it. Why should I be intimidated by this asshole?'

He had been drunk, confused, scared....

'Yeah. Yeah that guy was just taking advantage! He's nothing but a coward.'

A sense of righteousness fuelled him as he marched faster up the driveway - If he saw Andres, he was going to give the man a piece of his mind.

He burst through the front door, and the wind got ripped from his sails.

Sitting on the sofa was Andres, naked.

Steph's eyes zoomed straight to the cock, drooping down onto the edge of the seat, lingering on it for twenty heart-stopping seconds, before sliding their way up his trimmed crotch, abs, and chest.

His posture was laid back, and he didn't move a muscle when Steph murmured, setting his eyes on that chiselled, movie-star face.

It was a long time staring before Andres' voice broke the silence.

"Want to watch a film baby?"

"N! N-no..."

"Why not?"

He was losing control of the ability to speak, and Andres smiled as he filled in the sentence for him.

"Ah, I remember... it's because we were going to buy some games for you at the mall."

Steph's brain had gone numb, and he was in need of any excuse that would make Andres put some clothes on and lower the tent rising in his panties.

"..y-yeah," he managed, cock continuing its steady journey until the sensitive tip was pressing against the soft interior of the lace.

"Good," said Andres genially, before standing up and walking to within a foot of him.

Steph stared straight ahead at the man's sternum, because moving his gaze up or down would only lead to God knows what.

"We're going to have a good time, right baby?"

"Y.... N-no..."

"You don't know?"

A blood vessel outlined on Steph's temple as he fought all-new instincts to suckle the man's lips, clutch his thighs, lick that perfect mushroomed head....

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

"What's my name?"

Steph's lower lip quivered.

"Daddy."

Andres brought a finger up and brushed his cheek, smiling as it brought out a blubbering whine from the boy, before turning and walking slowly up the stairs, cock swinging in front of him as his glutes rippled with each step.

"Get ready, we'll be leaving in ten," he called over his shoulder.

When Andres had disappeared, Steph moaned and fell to his knees, pre-cum forming a spot inside his panties where he briefly rubbed the tip through his jeans.

"F-uuck," he whined, as the intoxicating scent of his man dissipated.

When he finally stopped, chest rising and falling slowly, the reality came to him, like a biting wind that shirked no crevasse of the skin.

'You broke as soon as you saw him....'

Andres was like a drug that he couldn't quit; An addiction ensnaring him in its grasp. If he didn't get away there was no knowing how deep he might fall.

'But I don't have money.. It's all locked in my room.... My passport too.....'

Trembling hands ran through his hair and then Steph realised that if they were going out Andres would not accept the boy-ish style (although with his diminutive figure and ruffled blond hair that wouldn't look out of place in a boy-band, it didn't exactly push him into masculine territory.)

Steph was suddenly filled with energy, bounding up the stairs to grab the same wig he had worn yesterday, part of him wishing he could feel what it was like to have his hair pulled, and then whimpering as he loathed his brain for trying to force these weird thoughts on him.

At least if they went to the mall he could maybe get some flowers for Grace....

He checked inside his pants to see if the garters still looked good on him, and found himself biting his lip and touching the end of his penis through the material.

"Ooooh," he murmured, cock ramrod straight as he oscillated his fingers on the tip.

Funny, it kinda seemed like a clit when he teased it like this.

Another small spurt of pre issued from the tip, widening the wet patch on the black material as he imagined sucking Daddy's cock.

His clitty was getting so hard it was aching.

As he was playing with himself, all his predicaments fell to the back of his mind until the deep call of a man echoed through the house.

"Baby??"

"C-COMING!" he cooed, as he wiped the dribbling pre from his tip with a finger.

He briefly thought about putting it in his mouth before grabbing a tissue instead.

The pretty figure stumbled out of Grace's room.

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