Transitioning in Love

I

"I'm here, I'm queer, and I wanna go home." Jasper said as he sat down at the table with his friends.
Jasper is an eighteen year old boy of medium height with light hazel eyes, light brown hair with the fringe dyed rainbow, a tan skin that's covered in freckles and some acne on his face. All in all, he looked cute. He was wearing some jeans and a bright green shirt, along with his rainbow bracelet which he always wore.

People around the table groaned a little and laughed.
"We all know you're gay, you've made it quite obvious dude." said Walter while he played a little with Jasper's rainbow fringe.
Jasper just laughed at that.
"Hey, rainbows are just pretty, it's just a bonus that they're gay."
Walter just laughed and ruffled his hair.

"Hey, guys, can I tell you something?" Jade spoke up, making everyone shut up and look at her. She was one of the more popular people at school. She had pale skin, dark brown hair, and deep blue eyes. She was about a head taller than Jasper, and all in all, pretty.
She looked down and fidgeted a little before quietly saying "I'm not a girl."
Everyone went quiet, so me, being the resident gay and having the most experience with being LGBT spoke up for all of us. "That's cool, what are you then? A boy, an enby, a mix, something else?"
They seemed a little relieved at that and said a little louder this time.
"I'm just a boy, thanks." He smiled a little.
This time Sadie spoke up. "It's so cool that you can tell us Jade, I wish I was so brave."
He cringed a little at hearing his name, just enough to be visible. "Could you guys call me Milo from now on?" he said.
"Sure we can Milo, it will take some getting used to but we will try, for you." said Sophia, patting him on the back.
He smiled widely at that and laughed a little. "Thanks guys, thank you so much, I was kinda afraid that you wouldn't accept me for who I am."
"What are you talking about," Jasper said, "you're a guy, why wouldn't we support you, you're still the same friend we've always known." He gave Milo a thumbs up.

"So, who wants to watch the football tryouts with me?" Jasper said, changing the topic. "I bet you are gonna run for team captain again, won't you?" He asked Walter.
"Nah, I think it's time to let someone else do that, I'm just gonna be a player this year."
"Are you even going to make the football tryouts? You have your own tryouts to attend to." Said Ron with a smirk. Jasper groaned and said "I was hoping you forgot about that."
"Come on, a deal is a deal, you lost fair and square, now you gotta be a cheerleader." He just banged his head on the table.
"Why did I ever agree to a pizza eating contest with you."
"Come on, cheer up dude, it's not that bad, we both know you don't mind being feminine."
"Ugh, fine, but if I miss out on the football tryouts I'm gonna be annoyed, I wanna watch you run around in skintight pants, full homo."
Everyone laughed at that.

After lunch, Jasper walked with Milo towards their lockers, which were conveniently next other each other.
"Hey dude, just wanna say I support you so much, and if you want help with transitioning I can give you information and moral support. We're brothers now in some sense."
Milo smiled. "Thanks, I think I'm gonna need it, it seems so hard to transition, I don't know where to start, what I can do even."
"Well, a good place to start is things that are easily changed, clothes, hair, and all that. We should go on a shopping trip together after school."
Milo smiled. "That seems good."
"The next steps would probably be binders and Packers, special clothing you wear to make you seem less female and more male. Or you could go right for surgery, but that costs a lot of money."
"I'm not sure if my parents would ever give me that money, they don't think well of 'the gays' as they say."
"We're still gonna go shopping today."
Milo just smiled and nodded before grabbing his books and heading off to class.

Jasper dragged Milo into Burlington that afternoon, going right for the men's section.
"Pick out anything you like, I'll pay."
Milo smiled widely and instantly started searching through a rack of hoodies.
"Really, hoodies? It's August."
"You can never have enough hoodies. And look, this one has a puppy on it."
"You dork" Jasper just shook his head while Milo continued to gather hoodies.
"Okay, now, let me introduce you to the wonders of men's jeans." Said Jasper when Milo had five hoodies in his arms.
"Unlike woman's jeans, men's jeans have actual pockets." Jasper pulled out a pair and stuck his hand in the pocket, which went in past the wrist.
"Try some for yourself, they're comfortable." He said as he took all the hoodies from Milo, who exitedly grabbed a bunch of jeans, ranging from skinny to tight, and in several sizes.
"You can try them on later, let's first look at some shirts. You might want to get the baggy because it helps you hide your body." Jasper said as he took all the jeans from Milo.
Milo smiled and grabbed a lot of different shirts with every color of the rainbow. Some even had actual rainbows on them.
"Thank you so much for doing this Jasper." Milo smiled brightly.
"It's okay Jade. I mean Milo! Sorry, I'm still getting used to it."
Milo just smiled. "At least you're trying. And you're helping me so much with this."
"Yeah, yeah, it's okay, like I said, we're kinda brothers now, I gotta help you out. Besides, I wanted to buy some more jeans for myself too, so this is just convenient."
"I'm still gonna thank you, let me pay for those jeans."
"Alright, deal. I pay for your clothes, you pay for mine."
They shook hands and walked towards the dressing rooms, Milo showing off every combination of jeans, shirt, and hoodie that he could. Jasper smiling at all of them and complimenting him.
When Milo had tried everything and decided to get it all, Milo went to the counter and quickly paid for everything, relieved that he could carry it around in bags now.

"And now you." Milo said.
Jasper smiled and led him back into the store. "I just need some new jeans, that's all."
He led them to the woman's section and grabbed a few jeans.
"The men's leans may have pockets, but woman's jeans really accentuate your ass, so the fake pockets are worth it, you could always expand those at home."
Milo just smiled. "Do you have any care for gender roles?"
"Nah, fuck gender roles." Jasper said as he grabbed a skirt. "Ooh, this is cute."
"Fuck gender roles indeed." Milo laughed.
"Honey, if you saw how I rock a dress, you'd understand."
"I'll get to see you in a cheerleaders outfit though. Please tell me you're going for the girls outfit, crop top and skirt and all."
"Of course, do you think I'd let these hips be hidden by jogging pants? No way." Milo and Jasper both started laughing at that.

"I can't thank you enough Jasper." Said Milo as they're walking out of the store, bags of others with them.
"It's really no problem, now, let's also het you a haircut to match your new masculine style."
Milo smiled as Jasper dragged him to a nearby hairdresser.
"Arlo! Get this man the manliest haircut you can do!" Jasper yelled as soon as he walked in.
"I'll be with you in a minute Jasper, calm down." Arlo said as he was finishing up a customer.
After they paid and left Arlo sat down next to Jasper. "So, what can I do for you this time, want me to redye your hair again?"
"Well yes, that would be nice, but this time it's not about me. I want you to give Milo here the manliest haircut you've got."
"Oh, no, you don't have to, my parents wouldn't approve of that." Milo said quickly.
"Okay then, a gender neutral haircut that can still pass as manly. Think you can handle that?" Jasper said.
"Of course I can, you know me." Arlo said and quickly ushered Milo into a chair, getting an assistant to redye Jasper's fringe.
"So, tell me, why does my favorite customer come barging in all of a sudden a week earlier than normal, with a complete stranger who's hair I must cut?" Arlo asks as he works on Milo's hair, cutting it very short at the sides and the back, leaving it tall on top.
"Arlo, honey, Milo here came out as trans today and I just had to help him, we went shopping earlier and man, we got so many clothes."
Arlo smiles as he continues to cut away Milo's hair.
"That's absolutely wonderful, you couldn't have chosen a better friend to come out to sweetheart."
Milo blushes a little under all the attention but Jasper grabbed his hand and lightly squeezed it.
Arlo held up a mirror to show milo how his hair turned out while Jasper inspected how well the assistant dyed his hair.
"She's getting better Arlo, I can't find any mistakes."
Milo was just starting in shock at how his hair looked, he reached up and ran his fingers through it.
"I love it so much." He said softly.
Arlo smiled at that. "That's the whole point darling. Now go out there and show the world who's boss."
Jasper smiled and quickly paid Arlo. "I'll see you in a few weeks."

Jasper dropped Milo off in front of his house and handed him all his clothes with a smile.
"Thank you so much for doing this with me Jasper."
"Of course, you're my friend, I'll gladly help you out."
"Now let's hope my parents don't notice I'm home late."
"Hey, it'll be okay. Besides, you got these awesome new clothes, I think that that makes facing your parents just a little more bearable. Don't you?"
Milo smiled. "I'll see you at school tomorrow, I wanna see you rock that skirt you bought today."
The two boys waved and each went their ways, smiling after enjoying the day.

A/N: Hey peoples, this is a new original story I'm writing. I'm particularly exited to write this because it's partially made out of spite toward cis gay men who don't want to date trans people.

Have a nice day further! I love you all!
♥️