Dress-up Doll Punishment (3)

Hey there dudes and dudettes! I am back with a new cap, this time around a caption trade with Ugu-Deviant-2, who wanted another sequel to my Dress-up Doll Punishment caption! I hope that you all enjoy this cap, and until next time stay happy and healthy!

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"Oh, this is so great!" Mandy said, her hand busy turning Tiffany's hair into a long braid. "It probably has been ages already since we last had a proper sleepover, I can't remember!"
"It has been years!" Zoe agreed, busy painting her nails a bright pink. "The last time was when we were what, 12 years old? I still remember you wanting us to stay up all night that day, Tiff."
"Yeah, those were some great memories" Tifanny laughed along, happy that everyone was having fun. "And we are just making more good memories. Don't you think so too, Brittany?"
Said the feminized boy in question didn't say anything and instead decided to pout, making all the girls laugh at the feminine action, making Brian just lower his head in shame.

And to think that just hours before Brian would have no clue in what kind of situation he would find himself in as his clock began to ring at 5 in the morning, making him wake up groggily.
Ever since his little outburst a few days ago and the day at the pool things have only gotten downhill, both Tiffany and Sarah now demanding that Brian learn more about being female.
So from now on they put him on household duty, meaning that it was now his sole responsibility to cook and clean around the house, while the other two females took a backseat and watched.
Normally he just had to get up at 7am to cook breakfast for his step-family, but for some reason today they wanted him to get up bright and early, not telling him why this was.

But with no choice he just did as he was told, donning 5-inch heels and an apron over his underwear as he cooked french toast and pancakes for them while he got to spoil himself with some yogurt.
After breakfast Sarah forced him to clean up the house immediately, a course that was usually reserved for the afternoon, making him just more confused at the change of routine.
However in the afternoon he finally found out why the two females changed up his normal work routine as the doorbell suddenly rang, and before he knew it his sister was sprinting down the stairs.
"I got it!" she shouted shortly before opening the door, and to his shock Brian saw Mandy, her best friend, and Zoe, her other best friend and his crush, standing at the door.
"Oh my god, it has been so long!" they all gushed, the two non-family members entered the house with duffle bags, and Brian tried his best to disappear as quickly as possible, not wanting to be seen.

"Oh Brian, no need to run, Tiffanny told us everything" Zoe's voice rang out, stopping Brian in his tracks as his eyes went wide, and all the girls giggled at the shocked look on his face.
"Yep! And we can't wait to have you be part of our sleepover!" Mandy continued, making Brian just more shocked. "But first I think we need to get you dressed appropriately!"
And with that the three girls grabbed a still shellshocked Brian, and as quickly as his high-heel-clad feet would allow they dragged him upwards to the bathroom where they started their work.
The trio began by removing the pink polka-dot dress he was wearing alongside his heels, before finally removing all the underwear he was wearing, leaving him completely naked.

"Oh my god, I didn't want to believe Tiffany at first, but holy hell, you really are looking like a girl!" Zoe exclaimed with a laugh, looking at Brian's hairless body, his glued privates and tiny waist.
"Of course Britanny does look like a girl" the step-sister huffed, feeling insulted. "We did our best to make her as beautiful as she is! And outside the ass and chest it is all natural!"
This of course made all the girls laugh at Brian's misfortune, none of them feeling sorry for the situation he was in, while the guy in question could only burn up in shame and try to hide.
"But anyway, I think we agreed to have a sleepover, right? So I think it is best to get our newest member ready, don't you think so too, girls?" Tifanny said after she calmed her laughing down.
All the girls nodded in agreement, either with evil smirks or big smiles on their faces, and Brian could only gulp as the girls approached after grabbing clothes from their duffle bags.

Before he knew it the girls pushed him onto the bed before grabbing a sheer white lace thong and pulling it up his legs, followed shortly after by an equally sheer white bra clasped around his chest.
Afterward the girls grabbed a satin nighty that they pulled over his head, Brian not struggling at all since he knew it was pointless, though the shame made his face turn a dark shade of red.
Without any resistance the clothing was done quickly, the nighty just barely managing to reach over his ass while leaving his side completely visible and showing cleavage.
"Wow Brittanny, you really are a beauty! I never thought you would pull that look off!" Zoe praised, though her words did nothing but crush Brian's spirit as they led to heavy laughter.
"Though IO think it is kinda unfair that you are the only one looking ready for a sleepover, so how about we get changed ourselves?" she continued while the girls reacher for their own nightwear.

At this Brian's excitement grew, thinking he would at least get to catch a peak on his crush, though those hopes were quickly dashed as Tiffanny threw her jacket onto his head, blinding him.
"No peeking, Britanny" she teased, knowing full well what her brother hoped for. "I know we are all girls here, but we still want our outfits to be a surprise for you, you know?"
And so Brian could do nothing but listen as clothes were discarded and the girls giggled and joked a bit, and after a few minutes the jacket was removed, revealing the girls in normal pajamas.
"W-Why am I the only one wearing such an outfit?" he asked, disappointed to see that there was nothing for him to see. "Why are you asking us that, you silly ditz? It is your wardrobe after all!"
"Yeah, don't blame us for your own clothes" the girls replied, laughing silently at their own jokes at his expense. "But enough of this, I think it is time we finally start this sleepover, right girls?"

"Heck yeah! How about we start by doing each other's make-up?" Mandy suggested, and so Brian was forced to play along with everything the girls had planned for their get-together.
As the makeup was first the girls covered Brian's face in foundation, doing the same to their own faces, giving everyone a pale and smooth complexion, before they moved on to their eyes.
Brian's eyes quickly got the whole treatment, starting with newly plucked eyebrows, and lashes caked in large amounts of mascara to make them dark and to give them volume, followed by eyeliner.
And where Brian was given some heavy doe-eyes that made him give a girly and flirty look automatically the girls themselves stayed more neutral, not even plucking their own eyebrows.
After that came the lips, and while they just added some naked lipstick to themselves Brian got the full beautification, with lip plumper and a shiny lilac gloss, followed by some lipliner.

"Wow Britanny, I would die to be as sexy and beautiful as you!" Tiffany said, her statement actually being somewhat earnest as she admired her feminized brother, and the others nodded in agreement.
"Yeah, but I think it is time for some hairstyling now!" Zoe suggested, and so the girls found themselves doing each other's hair after putting Brian's into long wavy locks, talking to each other while Brian just sulked on the ground, hoping that this nightmare would end soon.
"Hey Britanny" Mandy called, bringing Brian out of his funk for a bit as she addressed him. "This question has been burning on my tongue the whole evening, so what do you look for in a guy?"
"W-What?" Brian squeaked out as his eyes opened wide in shock and alarm. "Guys. What are you looking for in a guy? What do you find attractive and want for a boyfriend" Mandy explained.
The girls all started giggling at the question while Brian just continued to stammer and turn red from embarrassment. "Oh, Brittanny likes them big and strong, someone that really can take control!" Tiffany said before fishing out her phone and showing pictures of Brian getting sunscreened.

Brian's eyes bugged out at that, not having known that his sister was taking pictures of this humiliating experience, the girls on the other hand started to squeal loudly at seeing the image.
"Oh my god, he is like such a hottie!" "Yeah, just look at those muscles! Truly a beefcake!" "Brittany, you are sooo lucky! So, when are you two going on a date?" the girls rapidly said.
Brian was barely able to follow the girls as they were speaking so fast, but he still managed to answer them. "W-Well, never. I – Yo- I mean, I don't even have his number" he mumbled.
This led to Mandy and Zoe to let out disappointed sighs, and for a second Brian thought that they would drop the subject, though those hopes quickly died as he spotted an evil smirk on Tiffany.
"Aww, is that the only reason?" she asked, and before Brian could react she took pictures of him in his revealing nightie. "Luckily for you, I asked for his number, so I can make a date for you!"
This comment made the other girls squeal once again, and in seconds they were all huddled around Tiffany's phone, typing away and sending Brian's picture, while the feminized guy could only sit in shock and ask himself how his situation just kept getting worse and worse.