Halloween & Pool Party (TG story) Commission

Halloween & The Pool Party

The drinks had been following all night! Derek was astounded that he was still even able to stand. Swaying gently back and forwards in his girlfriend's high heels, he’s secretly pleased with how much fun he’s had at the party!

See, he’d planned to dress like Iron Man, but after his order never showed up, they had to think of something quick on the spot.

Being a makeup artist, Vale worked her magic on Derek. Coupled with a lush curly blonde wig and some super real-looking breast forms, Derek had been completed transformed.

“Have you enjoyed yourself?” Vale asks, pushing up against him and holding his hand.

Turning to look at Vale, Derek swipes hair from his eyes and smiles. He had really enjoyed himself. Even though everyone knew who he was, he’d been getting so many compliments from everyone. Most just couldn’t believe how convincing he looked.

“….I have to say…..,” He pauses and looks down at his white & gold patterned dress. “I think I did.”

Vale smiles and leans to peck him gently on the cheek.

“Shame we have to go….right?” she replies, looking up and down the road for the taxi they’d ordered.

Still looking down at his feminine-looking figure, he looks past his large plump feminine chest and looks at the high heels he was forced to wear.

Holding out his legs, he understands how sexy they make him look, but they are starting to pinch at his feet.

“These are starting to hurt…,” he comments, pointing down at the black pointed stiletto

Vale giggles and holds him tighter.

“Honestly baby,” he cheers. “I’m so proud of you wearing them all night. When I suggested you wear them, I thought you’d take them off five minutes into the party!”

“Oh yeah…?” Derek asks, puffing out his feminine-looking chest. “I make a great girl…huh?”

Moving to stand in front of him, Vale looks him up and down and smiles.

“Oh sure!” she says, touching at his dress and long curly hair. “I was worried tonight you’d get drunk and let some boy touch you up.”

“No way….!” Derek answers, tucking hair behind his ears. “Although, do you still find me attractive looking like this?”

Derek pauses and once again looks down at the silky tight white dress wrapped around his feminine-looking body.

“I mean….,” he continues, putting his arms around Vale’s neck and leaning in close. “I thought I’d be more embarrassed about fitting and looking good in your clothes. I just thought you’d hate your man looking so ……girly”

Vale smiles and the pair share a kiss.

“So….,” Vale giggles as they stop kissing. “….my boyfriend is a hot chick. I’m ok with it. I’m the one getting to take you home tonight!”

Derek blushes and looks away.

“Don’t be shy!” Vale laughs, gently moving his face back to look at her. “I’m actually really turned on right now. I don’t know if it’s the drink…. or the fact you're rocking my high heels!”

Kissing again, Derek feels Vale put her arm around his back and squeeze his ass.

“Well…,” Derek playfully moans. “Maybe I should dress like this more often…?”

Vale looks up at him and goes bright red.

“….Yeah….,” she bashfully answers, looking deep into his eyes. “I-I would like that! Just the thought of you wearing my skimpy thong and I start getting all wet!”

Biting her lip, Vale waits for his response.

“I think we’ve found a new turn on your for Vale,” Derek smiles, flicking his hair back playfully.

As they share another kiss, the bright headlights of the taxi light them both up. As the taxi pulls up, Derek pulls his skirt down, nervous his tackle might be on show.

Awkwardly getting into the car, Vale does all the talking, and the journey back is a little uncomfortable for them both

All Derek wanted to do was kiss and fondle his girlfriend, but knowing he looked like a girl, he was worried about what the taxi driver would say. He had to settle for secretly holding her hand.

As they pull up outside their apartment block, the two slowly make their way home.

By this time, Derek was really struggling with his heels and the staircases didn’t help.

“Argh,” he whines, taking another agonizing step. “These heels!”

Vale, coming up behind, pats him on the ass.

“Come on girl!” she cheers. “Nearly home!”

Now feeling the chill of the night on his smooth legs and barely covered body, Derek begins to wonder why women wear so little.

Folding his arms tight, they scurry to their front door.

“Jeez!” he whines, bursting into the door and instantly feeling the heat against his shaved body.

Shutting the door behind them, Vale unties her hair and starts unzipping her Catwoman costume.

“Tell me about it,” she groans, pealing the leather suit from her body.

As Derek watches his stunning girl gets slowly undressed, he can feel himself getting excited by the sight of her.

Feeling growth inside his silky panties, he’s worried he’s going to pop out.

Wanting to touch her, he brings his hands up to his blonde wig and starts to remove it.

“Wait!” Vale cries, kicking off her leather boots.

“What…?” Derek replies, quickly putting his arms to his side.

“Can….you….?” Vale says but stops short.

“Can I…?” Derek questions, getting impatient and desperate to remove his heels.

“Can you……,” Vale steps closer. Now only wearing the leather leggings of her costume.

Pressing her breasts against him, she looks him in the eye and smiles

“Please stay dressed as a girl for me tonight!”

Derek looks stunned for a moment.

“Can I at least take the heels off…?” he whines

Vale laughs and nods her head.

“Yeah, but leave the wig, your sexy underwear, and the makeup!” she commands.

Derek raises an eyebrow.

“Please…..!” she pleas. “I wanna pretend I brought the prettiest girl back from the party!”

Looking down at himself and the effort they’ve gone to, he can’t help but feel like it would be a shame if he did change straight away.

“I guess I did shave my entire body for this look…,” he mumbles, holding out the skirt of his dress.

Derek looks at the bright red face of his slightly drunk girlfriend and gives her a big grin.

“Ok!” he says, putting his hands on his hips. “I will be a girl for the rest of the night.”

“Great!” Vale cheers and claps.

After sharing a quick cuddle, Derek looks to start unbuckling his heels.

Helping, Vale gets to her knees and slides them off his feet. Looking at the red marks the heels have made on Derek's feet, Vale gently kisses them better.

“Hard work heels….aren’t they?” Vale comments, still tending to his feet.

Derek looks down and nods. He’s relieved to have them off.

“Nice that you can fit into my shoes though,” Vale continues, looking up with a smirk.

“I guess….,” Derek replies.

“I love how your feet our my size!” Vale giggles. “It’s like we are a proper lesbian couple. Wearing each other's clothes!”

“You do…?” Derek questions, feeling a little emasculated by the small size of his feet.

“Yeah!” Vale instantly replies. “I wish you’d be my girlfriend for the pool party tomorrow too!”

Derek shakes his head and imagines wearing one of her bikinis. He’s instantly put off at the sight of his package out for all to see.

“I don’t think that’s wise,” he softly answers, not wanting to hurt her feelings. “It’s all good to be crossdressing for a Halloween party, but to turn up at their pool party as a girl? I think I’d frighten a few people.“

Standing up, Vale pushes her half-naked body against his.

“Yeah…..,” he sighs in response. “I guess I will just have to wish for you to remain a girl for tomorrow.”

Leaning in and giving him a kiss, she squeezes his backside once more.

“Good thing you’re still my little blonde bombshell tonight,” she lustfully whispers into his ear.

Running her hands up his silky short white dress, she slowly unzips the back of it.

“Get into that bedroom girly!” she giggles. “I want to snuggle with you!”

Vale pushes him into the bedroom and almost rips the dress from his body. She exposes his freshly shaved body, fake breast bound in a lacy bra, and his privates wrapped in a stringy thong.

Kissing each other passionately, Vale takes the lead and pushes him onto the bed.

Drunk, dressed, and turned on, the two go on to enjoy a passionate time in the bedroom before laying on either side and falling asleep. Derek doesn’t have the energy to remove his female garments, he stays wearing her underwear, makeup, and the lush wig.

The next morning, Dale awakes early absolutely desperate for the toilet.

Moving carefully, trying not to wake Vale, he slowly gets out of the bed.

Noticing that he’s still got long hair and a bra on, he laughs at the memories of the night before. She was so desperate for him to remain looking like a girl!

Tiptoeing to the bathroom, Derek stands in front of the toilet and moves to relieve himself.

Reaching down to the thong he had one last night, he’s left instantly confused and concerned.

“What the….,” he moans under his breath, struggling to find his manhood.

Almost feeling like he’s in a dream, he realizes for a moment that he can’t feel it bulging out of his feminine underwear.

Thinking he must be hungover, he leans forward and tries to look between his legs.

His eyes grow wide with terror and disbelief.

“Whaaa,” he yells, pulling down the thong to reveal nothing but flat skin.

“It's GONE!” he screams, jumping back in fright.

As he jumps in the air, his entire body bounces and jiggles in very unfamiliar ways. His ass feels heavy and plump.

Shaking with worry, he turns to the mirror and looks at his face.

Doing little to calm him, he can see it’s still him, but he looks so much thinner and feminine.

Touching his face gently, he tries to look past the old makeup on his face to understand why he looks different.

Feeling how soft his face seems, he looks up at the wig on his head. He reaches up to take it off.

“Ouch!” he whines, with an increasingly feminine sounding voice.

The wig seems unable to move. It feels attached somehow.

“Ouch!” he cries, as he tries harder to pull the wig from his head.

Feeling the pain of his hair being pulled, Derek's heart is beating like mad.

“What's happening to me!?” he grumbles, still desperate to use the toilet!

“Vale!” he screams.

Bolting from the bed, Vale stumbles across the room half asleep, and bursts into the bathroom. Rubbing her eyes, she stares at him unimpressed.

“What is it!” she gripes, yawning.

“I-I…,” Derek pauses, unable to tell her he can’t find his own junk

“Derek,” Vale yawns again. “Just tell me why you’re screaming so high-pitched this early!

Derek looks down between his legs then instantly back up at Vale in worry.

“..So your still wearing my thong…?” Vale moans, annoyed.

“I can’t find it!” Derek quickly replies, standing with his legs wide apart.

Confused, annoyed, and tired, Vale stamps over to Derek and roughly pulls his thong down. About to point and get annoyed at his stupidity, she’s stunned by what she see’s between his legs.

“What….the actual..fuck!” she says, covering her mouth in shock.

“See!” Derek screams, now shaking with fear.

“Derek!” Vale says, getting to her knees to investigate. “You can’t find it….because…..”

“Because what!” he impatiently bellows, watching her between his legs.

“You’ve got a vagina!” Vale replies, looking up at him confused and concerned.

Gently reaching in, she touches one of his soft vagina lips.

“What the fuck!” Derek jumps back away from her, having it touched for the first time.

Standing, Vale looks Derek up and down. She touches his hair and bounces his breasts.

“I wished for this…,” she mutters, looking at him intently.

“Wish for what..?” he nervously asks, having felt her touching the boobs on his chest which are meant to be fake.

“Last night, when we got back. I wish for you to be a girl for today!” Vale cheers, excited. “I think it’s come true. Look at you! Stunning body with all the correct curves and equipment. Even your face looks more feminine!”

“Huh…!?” Derek grunts, still confused.

“Derek!” Vale claps. “The reason you can’t find it….is because you’ve transformed into an actual girl. You are a woman!”

“No..no..no…,” Derek replies, shaking his head. “That’s not possible!”

Vale puts a sassy hand on one hip and gives him a look.

“How else do you explain the tits and vagina…?” she asks, giving him a sarcastic smile.

Derek, lost for words, dances on the spot.

“I don’t know!” he gripes. “I just need to go to pee…! What do I do!?”

Raising an eyebrow, she looks at him and points to the toilet.

“Well Hunny…,” she giggles. “You are halfway there with your panties down. Just sit on the toilet and let the wee out.

“Ok..ok!” he nervously answers at speed.

“Come into the bedroom once you are done,” Vale commands. “We’ve got outfits to plan, makeup, and hair to do!”

Leaving the room to the sound of her boyfriend urinating like a woman, she has a smile on her face. Finally, Vale can introduce herself as a lesbian and not feel any guilt at all!

Quickly moving around the room, she pulls out swimwear outfits and other feminine items.

“Vale….?” Derek says meekly, moving into the room with his panties now pulled up and his hair thrown back. “I don’t like this. I don’t want to be a woman.”

Holding some bikini bottoms, Vale gives Derek a look.

“Why not…?” she questions.

“This is so weird!” he moans. “I don’t want this. I don’t want to be a woman!”

Vale allows herself to slump as Derek’s mood drains her excitement.

“What difference does it make?” she asks, pointing at him. “You were more than happy to wear heals, my underwear, and a dress yesterday. You said you enjoyed looking like a woman.”

Sitting awkwardly on the side of the bed, Derek hides his feminine features.

“I’m not me anymore!” he whines. “Even though I was seen as a girl yesterday, I was still me under all that garb.”

Kneeling in front of him again, Vale puts her hands on his supple feminine thighs.

“Think of yesterday as a test run!” she says, looking deep into his large blue eyes. “You passed as a girl yesterday, even though you had the wrong tackle between your legs.”

“So…?” Derek replies, looking away.

“So….imagine how awesome today will be now you’re actually a woman. How sexy you will look in swimwear. How cute you’ll be wearing heels with these long legs. How stunning you will be with your lush blonde hair wet from the pool!”

Turning to face her, Derek looks deep into Vale's honest eyes.

“Yeah….?” He softly questions.

“Yes!” Vale instantly replies. “You’re so fucking stunning. I can't believe how hot you are as a girl! I’m…..deffo no longer the hot girl in our relationship!”

Derek opens his body out and looks down at the breasts held in by the bra he wore last night.

“Please Derek…,” Vale continues, giving a smile. “If it is just for one day, I want to enjoy having such a hot girlfriend. I want to show my lesbian lover off!”

“Lesbian..?” Derek asks, focusing on Vale.

“Yes baby!” she replies, gently moving her hands up his thighs towards his vagina. “We are lovers…?”

“Yeah,” Derek answers.

“So then we are lesbians,” Vale cheers. “We are two sexy women in love!”

Giving it a moment, Vale and Derek just stare into each other's eyes. Vale gives him a smile as she sees the cogs turning in his mind.

“Oh fine…,” he huffs. “I’m your girlfriend today! …..What do you want me to wear?”

Jumping up with joy, Vale plants a big wet kiss on his lush feminine lips.

“Thank you!” she says, kissing softly.

Derek doesn’t hesitate to kiss back. He loves his girlfriend.

As she kisses him, he notices his body reacting in different ways. Gone was the growth of his package and in with the fizzing sensating between his legs.

Vale quickly moves away and holds up a blue two-piece swimsuit.

“For the pool party you can wear this as your underwear,” she says, placing them on the bed next to him. “The bra won’t give your new girls too much support, so try to bare that in mind. No running, otherwise, they will fall out!”

Picking up the very soft but string-like bikini top, Derek nods at the advice.

Moving around the room some more, Vale picks up a lacey-looking sheer top and a pair of denim shorts.

“This will be your outfit today. Shows off that sexy little booty, but remains classy!” she says, showing it to him.

“With heels…?” he asks, looking down at his feet that remain sore from last night's heels.

“No baby girl,” Vale giggles, moving to her closet. “You'll be wearing these wedges.”

Having shown him the outfit, Vale takes extra time to ensure Derek looks like a supermodel. She brushes and curly his natural lush locks. She expertly applies his makeup. She paints his nails like an artist working on a fine painting.

Then, helping him into the bikini and extremely revealing feminine outfit, she takes a step back and blushes with how gorgeous he looks.

Awkwardly standing in the wedges, Derek doesn’t know how to handle his fully grown female form. He looks uncomfortable with the tight clothing clinging to his every curve.

“Do I look ok?” he asks, bashfully tucking his long hair behind one ear.

“Do you look ok…?” Vale asks, going red herself at his beauty. “I’m worried you’re out of the league baby girl!”

“Really…?” he asks, going a bit shy

“Fuck yeah!” she continues. “I’m worried you’re going to leave for the first man who pays your any attention.

Shaking his head, Derek moves towards vale and grabs her still half-naked body.

“No way!” he says, giving her a kiss on the cheek. “I’m a lesbian….remember!”