Transitioning in Love

III

"Guess who's team captain!" Ron yelled as he and Walter sat down at the table.
"Is it Walter again?" teased Dana.
"Ha ha, no it's not. It's me!" Ron replied.
"Hey man, good job." said Sophie as she pokes his cheek.
"Nice, it'll be easy to cheer for you." Jasper said and winked.
"Hey man, you've already got a date, I'm not gonna interfere with that." Ron replied.
"Yeah man, come on, I planned it all out, don't leave me like that all of a sudden." Walter said as he played with Jasper's rainbow fringe.
"Relax, I won't, just teasing."
"Speaking of the date, where are you going?" asked Sadie.
"I'm not gonna tell, it has to stay a surprise." Walter smirked as he said that.
"Aw, come on babe, just tell me. Please?" Jasper whined a little.
"Nope, you'll just have to whitness it, I'll pick you up at six thirty okay? And dress fancy."
"Ooh." said Sadie and Sophie in unison before sharing a knowing look.
"Okay, we gotta help you prepare for your date now." Sadie said while Sophie nodded.
"I'll bring my make up!" Sophie added.
"Wow, thanks girls, I'm exited to see how he'll look." Walter said.
"Yeah, yeah, you can send us the specifics later, we don't want to overdress him either." Sadie said.

As the group split apart Jasper walkee next to Milo again. "Can you come with me to my house after school? I wanna measure your chest so we can get you a binder, it'll flatten your chest, I'll teach you how to bind safely later."
"Are you sure? I don't want to interfere with your date." said Milo.
"Yeah, yeah, it's fine, there's plenty of time for us to do that and for the girls to show up and prepare me. And hey, maybe you can stay around, hang out a little. I'd like to have your opinion."
Milo smiled a little at that. "Okay, I'll come."

Jasper unlocked the front door and led Milo inside.
"Woah dude, your house is big." Milo said as he looked around the large foyer.
"Well, that's what happens when you have rich parents," Jasper shrugged, "sadly, it also means that they have a lot of important duties and thus are almost never around, it gets pretty lonely here."
"Ah, I understand, but at least your parents don't make you want to scream every night because of how horrible they make you feel." Milo said sadly.
"You know, we should have a sleepover sometime, just the two of us, or maybe the whole group."
Jasper walked into his room, and Milo started a little at what he saw. You wouldn't guess that Jasper's parents were rich from his room, it looked like a regular teenage boys room. Well, besides the full size pride flag that hangs above his bed.
"Okay, so, first things first, binder." Jasper said as he grabbed a measuring tape.
"Are you comfortable with me measuring it, or do you wanna do it yourself?" He asked hesitantly.
Milo fidgeted a little before he quietly said "Can you do it please?"
Jasper smiled. "Of course, I'm happy to help. But you will have to take off your shirt so I can measure properly."
Milo blushed at that.
"If you want to I can look away?" Jasper suggested.
"That would be nice, yeah."
Jasper smiled and turned around, giving Milo some privacy.
"Okay, you can look now." Milo said after he took his shirt off, averting his eyes. Jasper quickly took all the measurements he needed and turned around again, grabbing his laptop.
"I'm done, you can put your shirt back on."
Milo looked over Jasper's shoulder as they looked at gc2b binders.
"This is a good brand for binders, it's owned by trans people so they know how to do it good." Jasper said as he typed in the measurements.
"What color do you want your binder to be? Black, gray, white, or skintone?" Jasper asked as he went through the options.
"Let's go for skintone, I wanna be subtle with this."
"Okay, I'll order a couple for you right now." Jasper compared the different skintones available and chose the one most similar to Milo's tone.
"They'll arrive in a few weeks, but for now, let's hang, I've got Mario kart."
"Bring it on!"

At six am, Sadie and Sophie knocked and Jasper quickly let them in and went to his bedroom.
"Hey Milo, how are you?" Sadie asked.
"Good, I've been busy completely beating Jasper at Mario kart." Milo said with a smirk.
"We agreed no rainbow road, you cheater!"
"Hey, it's not my problem that you suck."
Sadie and Sophie rolled their eyes.
"Okay, focus please, we're gonna need some time, you can maybe continue gaming when we're done, but we have to choose your outfit first."
"Alright." He smiled and led them to his walk in closet.
"Should I wear a suit, a dress, or something in between?"
"I'd say in between. I'm sure that he'll love it and you'll look great." Sadie said and Sophie nodded.
Jasper showed them all the options.
"You gotta try them on and show us, have a little fashion show." Said Sadie.
"OMG yes, that will be so great." Said Sophie.
Jasper smiled and pushes them out of the closet before turning back and choosing his favorite.
"I'm fucking gay." said Jasper as he came out of the closet wearing a dark red pair of pants with above that a lighter red dress that went all the way to the ground at the back, but went higher up at the front to show off his pants, the dress had no sleeves and showed off his tan arms and shoulders in all the right ways. There was a wide rainbow strip at the bottom of the dress, which got thinner as it approached the front and eventually stops, Jasper was wearing a matching rainbow belt.
"So? How do I look?" Jasper asked as he did a little twirl.
The two girls and Milo didn't say anything as they stared.
Finally Sadie seemed to snap out of it and rushed up to hug Jasper.
"It looks amazing! You don't have to try anything else, this is perfect."
Sophie then grabbed his wrist and pulled him into the bathroom, sitting him down and and opening her kit.
Half an hour later, Sophie walks out of the bathroom and proudly shows off the work she did.
"Okay, so, I started out with a foundation, than added his freckles again because they're adorable. Some eyeliner, red lipstick, and burgundy eyeshadow finish off his face. And because I couldn't help myself I also painted his nails rainbow."
"I look so pretty." Jasper said amazed as he looked at himself in the mirror.
"What about the hair though?" Milo asked. "Come here and let me try something."
Jasper smiled as he sat on his bed in front of Milo, who quickly began braiding his hair in a ring braid, making sure that it shows off the rainbow dye.
"There, done." Milo smiled as the two girls complimented him on his work.
Just then a car stopped in front of the house and Walter stepped out with a bouquet of flowers in his hand, he was wearing a gray suit and red tie, his hair gelled back.
Jasper opened the door and smiled at Walter, who couldn't stop staring.
"Woah, you look beautiful." He said.
Jasper blushed at that. "I had a very good team to help me."
Walter smiled and handed him the roses. "Here, I got you these, thought you might like them."
Jasper took them and smelled them before rushing into the house to put them in a vase.
"I love them, now, shall we go? I wanna know what this big surprise of yours is."
Walter smiled as he held open the door for Jasper. "You'll see, gotta keep you in suspense for as long as possible."
Jasper sat down as Walter got behind the wheel and drove off.

Jasper couldn't help but smile as they stopped at Olive Garden.
"This is your bug surprise then, Olive Garden." Jasper smiled.
"Yep, I didn't want to go overboard with a five star restaurant on the first date. Also, I kinda didn't want to be broke after one date."
Jasper laughed at that. "I would have paid for it anyways, don't worry."
Walter got out of the car and helped Jasper up, linking their arms together as they entered the restaurant.
"I love your outfit so much, it's so you." Walter said.
They sat down at a window table that Walter had reserved and ordered a bottle of sparkling water.
"So, tell me a little about football, I'm gonna be a cheerleader, I should know some more if I want to really support you." Jasper started.
"Really? Well, if you insist." Walter started explaining all the rules while Jasper just listened with a smile on his face.
"Wow, that's a lot of rules, how do you remember all of them?" Jasper said.
"With difficulty." Walter said and they both laughed.
The waiter brought them the bill and Walter grabbed it, and read the price.
"Wow, that expensive?" He said surprised.
"Okay, give me the check, I'll pay."
"No, I took you out so I'm gonna pay, it's only decent."
"Honey, I asked you out on the date, besides, I can afford it."
Walter looked at the price again and slid the check over, hanging his head in defeat.
"Fine, I didn't think it would be this expensive, so I can't even afford it."
Jasper just laughed as he paid the bill and left a 25% tip.
"Shall we go then?" Walter said as he held his arm out for Jasper, who linked arms with him.
"Yeah, we shall, it's getting late."

When Jasper walked into his house, he was almost instantly tackled by Sadie and Sophie.
"How was it? Where did you go? Tell us everything."
Jasper laughed as he squirmed out from under then and sat down on the couch.
"So, he took me to Olive garden, and it was amazing, he was a total gentleman and even reserved a great table. The food was very good, it was all just amazing. Too bad he couldn't afford the bill so I had to pay, but I don't mind, I have money to spare."
The two girls squeeled exitedly, asking Jasper about it for the rest of the evening before they had to go home.
Jasper couldn't stop smiling as he tried to fall asleep.

A/N: Hey peoples!
I'm really happy with how this turned out.

I'm so happy for all the comments you send me and just the fact that people read my stuff and like it.
Have a nice day further, I love you all!
♥️