Pepper
Pepper is his first friend to notice something isn't right with him. Tony thinks she known somethings been wrong for a while because Pepper is just a very perceptive person but it's when he turns down her offer of going out to dinner while chilling her her house when she finally gets curious to ask.
"What do you mean by no?" She asked, Tony sighed.
"No means what it says on the tin Peps, I don't want to go get food."
"You never want to go get food, I'm starving and you've been at mine all day so I know you haven't eaten so what's the real reason?" Tony sat up making his back face Pepper.
"I don't really want to talk about it." He felt Pepper shift and soon she was sat beside him.
"Anne... Come on, what is it?"
"Just leave it be, okay? I just said I didn't want to talk about it."
"And I think you should, you've been acting off for a while an I honestly can't remember the last time you came out to eat with Rhodey and I," Pepper rubbed his back, "You're beginning to worry me Anne, I just want to make sure you're okay."
"Well I'm fine so drop it.."
"Anne..."
"Stop calling me that." Tony snapped, he knew he had no right in talking to Pepper that way because she had no idea and its just unfair but he was so tired of hearing Anne come out from her mouth.
"But... I always call you that?"
"Stop it."
"What do you want me to call you?"
"Nothing, ignore me." Tony said, he was steering this conversation right where he didn't want it to go.
"No, what is it?" She asked, moving to sit in front of him, hands resting on his knees, "Please."
"I just don't want to be Anne anymore," Tony was so close to tears, "Peps, I can't..."
"Can't what?"
"Lose you, I can't be Anne, I can't do this." Tony was panicking now.
"You won't lose me but you have to explain what you mean because..."
"I'm a boy!" Tony snapped out, his eyes widening with shock and Pepper quickly removed her hands and wasn't that just a punch to the gut, "Peps...?"
"What do you mean?"
"I... I'm... I..." Tony was choking on his words but he knew he couldn't back track out of this one, "I'm transgender."
"Is that... Is that why you're starving yourself?"
"I'm not."
"You are, I can see through you, it's not healthy."
"I'm just trying to fit in my body the best way I can, okay? I just want to look like how I feel."
"Oh..." neither of them spoke for a while and it was eating at Tony, he opened his mouth to excuse himself when Pepper spoke again, "I hope you know I'm okay with it."
"What?"
"You're my best friend, I wouldn't swap you for the world and this doesn't change our friendship," She smiled and put her hands back on his knees, "I still love you."
"Really?"
"Yes, I mean it, I'm just sorry I forced you to come out instead of waiting until you were ready."
"I don't think I'll have ever been ready if you didn't." Tony smiled the best he could.
"What do you go by? Name wise."
"Anthony... Tony for short."
"Tony Stark, I like that, has a real good ring to it."
"Really?"
"Yeah Tones, when did you think of that?"
"Jarvis has been calling me it since I was, like, five?" Tony said, "Anthony after my dad but he's a prick so I go by Tony for short."
"Suits you," She hugged him, "Is it only Jarvis and I who know?"
"No, I came out to my parents." Pepper pulled back quickly, eyes shocked.
"And... And how did they take it?"
"Badly, hence I'm not publicly Tony," Tony looked down at his skirt and wished he could be wearing jeans or something more comfortable, "I asked for a name change when I was eight, dad hit me and sent me to bed while my mother broke down, I tried telling him again a couple of years ago when I first started... Started, uh, starving myself?" it didn't sound right to Tony, he wasn't trying to do that at all, "Bought myself a binder and well, Howard caught me wearing it and remember those few weeks I didn't come into shool?"
"He didn't..."
"I wanted to come in but I physically couldn't get out of bed, he really wasn't happy when I said the word 'trans' out loud."
"Oh Tony, I'm so sorry."
"It's okay, I should have stayed quiet, it's just hurting everyone around me... I took some scissors to my hair last week and honestly you'd think I had stabbed my mom with them." Pepper looked at his head, his hair looking immaculate like always.
"But, you can't tell?"
"Oh you can, it's just a deal I made with mom," Tony unfastened the wig and pulled it off his head, only wincing slightly when the glue tugged at his skin. Pepper gasped, "I have to wear wigs and dresses 24/7 and she won't tell Howard of my 'accident' with the scissors."
"Jeez... Tony." Pepper said, reaching out to run her fingers through his short hair.
"I know, I'm no hairdresser but..."
"I like it."
"You do?"
"Yeah, I do, come with me." Pepper got off the bed and held her hand out. Tony didn't question it, he just took Pepper's hand and followed her out of her room; he trusted her.
Pepper lead Tony into the bathroom, she rummaged through the makeup bag left on the side and took out a bag of wipes and threw them at Tony.
"Take your makeup off and I'll be back in a second, wait here." She said, a wide smile on her face before she left the bathroom leaving a confused Tony stood staring at himself in the mirror. He opened the wipes and stepped forward so he could remove the makeup; feeling lighter as the eyeliner and foundation came off.
Pepper returned five minutes later holding some clothes and Tony was beginning to realise what she was doing, "I have some jeans that should fit you, I hope they're not too feminine but I stole one of my brothers AC/DC shirts which will be too big but..."
"They'll be fine, thank you." Pepper handed him the clothes, helping him unfasten the dress. It wasn't abnormal for them to change in front of each other so he didn't think twice about stripping with Pepper still in the room. The jeans just fit, his hips being that bit wider despite all the weight he lost but he knew he'd always be broader and he was okay with that. He slipped the tee over his head and when he looked in the mirror he felt like himself.
"Oh... Tony..." Pepper stood behind him, "You look amazing."
"I feel... More like myself, I bet this is so weird."
"What do you mean?"
"You've known me as Anne for so long to then thrust this upon you and I'm thirteen so you probably think I'm too young to know like my parents and..."
"Tony, you're my best friend whether you're a girl or a boy, I love you, you're old enough to know how you feel and by the sounds of it you've know who you are for a long time and I just want you to be happy and healthy and..." she ran her hands over Tony's arms and he knew exactly what she meant, "Now, how about we go downstairs and get something to eat?" Tony bit his lip, he could always do a bit of extra exercise when he left to make up for whatever he eats.
"Sure, why not."
"Brilliant, come on, I'm starving Tones." Tony couldn't wipe the smile off his face, he knew that he'd have to go back into pretty, little Antoinette but he was thankful for these few hours being himself with his best friend.
For the first time in a while he felt free.