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Description

It had been about two months since that day Terry tried on his big sister's skirt. It eventually escalated to him stealing her tops, skirts, and even panties. He still couldn't wrap his head around why he suddenly became so interested in cross-dressing with her clothes, but it gave him that soft, tingly feeling every time he tried them on. He didn't feel like a girl, but he felt somewhat comfortable with the clothes he tried on. Cross-dressing in secret in his room made him feel anxious, however. There were a few close calls with his mom and sister, but he knew it would only be a matter of time before someone caught him, and he hoped to God it wouldn't be his parents.

Then the day finally came when his secret was discovered. It was Laundry Day for Terry and his sister, Mariah. He had snuck another skirt into his basket and carried it into his room, to try it on. Terry had just put the skirt on and looked at himself in the mirror for a good moment when he suddenly heard the door knock. "Frick!" He quickly took it off and grabbed his shorts from the bed.

Mariah called through the door, "Terry, can I talk to you?"

"Uh, hang on, getting dressed!" He puts his shorts back on and buried the skirt into his basket before sitting at his desk. "Okay, come in!"

Mariah opened the door to enter, closing the door behind her. "Have you seen my new skirt? I put it in the dryer before lunch, and now I can’t find it."

"Did you check with Mom?"

"I did, but she said one of you boys must’ve mixed up the clothing again, and you did your laundry today. Can you check your pile for me, please?"

Terry sighed. "Alright, give me a moment." He searched through the basket to find the skirt he had just buried and pulled out her skirt. "Found it!"

Mariah seemed confused. "How come my clothes end up in your basket?"

Terry shrugged as a fake response as he handed the skirt to her. "Mix-ups happen, you know."

"Thanks, I guess," she said as she took the skirt. "But seriously, this is the fifth time this month I learn that my clothes are in your basket. Are you sure this is just a mix-up?"

"Yeah."
"Tell me the truth."
Terry snapped, "I am, okay?"

Mariah flinched for a bit at the tone of his voice. "Then why are you giving me a tone?"

"Cause you won’t leave me alone!"

"I just want to know what’s going on, Terry! You’ve been acting weird for the last couple of months, staying in your room and not letting people in, being silent most of the time, eyeing people in public like you’re afraid of something!"

"What I do is my business, not yours!"

"Terry, I’m worried about you! I know you’ve been feeling down about yourself, but all the sudden you’re shutting us away as if we don’t want to know something!"

"Just--!" Terry couldn't speak another word as he sat down on the bed, holding his head in frustration.

Mariah slowly approached his side and sat down next to him, speaking in a soft tone, "Terry, you’re my little brother… and I care about you. It hurts to see you this way. I just want you to tell me the truth. Whatever it is, I won’t hold a grudge against you. Just talk to me…."

Terry sat in silence for a minute, afraid to even say a peep, before slightly looking toward her. "Promise you won’t think I’m weird…?"

Mariah nodded. "I’ll try my best…."

Terry took a deep, shivering breath. "…I stole your clothes and put them in my basket. Before you get mad at me, let me explain why. You see… I don’t know why, but… after I found your skirt in my basket one day and tried it on to tease you, I…" He paused for a moment, sniffling. "…I kinda like it. I don’t know why, but when I try on any girls’ clothes, I feel like… like I’m looking at a different person, someone better than the old me. I don’t really see me as a girl, though (don’t you even think that’s what I meant), but I still see someone better than this me." He sniffled again, tears beginning to stream down his face, before taking in another shaky breath. "I don't.... I don't know what's wrong with me. I don't know who I am or what I becoming anymore."

Mariah was astonished, clearly not expecting the words that came out of his mouth. She could see that he felt so confused, unable to grasp his identity, and she pulled him close.

Terry sobbed. "I... I just seem like a total weirdo right now. Admit it."

Mariah processed that for a moment before replying to him, "Well yes, I’ll admit it’s a little weird, but… to be honest, I don't think that's bad."
Terry looked up in confusion. "How?"

"Well, maybe this “weird feeling” you’re getting is a way of rediscovering your identity, whether for better or worse. There are others out there in the world who I'm sure have felt the same way you feel right now. Guys who cross-dress and like it a little. Maybe you're one of those guys. You won’t know unless you try and take a chance. Who knows, it might make you happy."

Terry sobbed again. "B-but… if this is what I want to do… what will Mom and Dad think of me…? What about Alex?"

"We’ll find a way to talk to them about it, but if this is what you wanna try to do to be happy again, I say you should totally go for it."

"W-what about you?"

"You’re my little brother, Terry. I want you to be happy again. You may not turn out to be the same Terry I grew up with, but you’ll always be the little brother I love...."

A few more tears streamed down Terry's cheeks as he hugs his sister tightly.

Mariah held him close, brushing his hair through one of her hands softly and rubbing his back with the other.

It took a couple of minutes to comfort him until Terry finally spoke, "I… I love you, big sis…."

Mariah smiled and nuzzled his ear. "I love you, too, lil brother."

They spent another minute in the hug of comfort until Terry spoke again, "Mariah?"

"Yeah?"

"Promise you won’t tell Mom and Pops until I'm ready to, okay?"

"I Pinkie promise," Mariah said as she did the Pinkie promise as shown by Pinkie Pie in MLP.

Terry smiled a little. "Thanks…"

"And promise you’ll stop stealing my clothes, okay?"

"I won’t, I promise." Terry did the same promise in silence.

"Good." Mariah giggled as she booped his nose. "How about we go shopping tomorrow so we can find you your own clothing~? Just the two of us."

Terry's ears perked up. "R-really?"

Mariah nodded with an assuring smile.

Terry smiled in return. "That... sounds like fun."

Mariah stood up and look at him. "We'll work it all out, lil bro, I promise. We'll make you the happiest fox in the city -- and the cutest."

They both giggled.

(To be continued...!)

Finally!
After 9 long months, I finally got around to drawing part 2 of Terry's transition from boy to femboy!
And since it's pride month, it seems logical to do it now rather than this upcoming September.
Next part will be his first time shopping for girly clothes! Don't miss it!

You can find part 1 of his transition backstory here --> fav.me/dbo7epr

Terry and Mariah Nightpaw and art (c) 2018 RedHoofsketch

Description

It had been about two months since that day Terry tried on his big sister's skirt. It eventually escalated to him stealing her tops, skirts, and even panties. He still couldn't wrap his head around why he suddenly became so interested in cross-dressing with her clothes, but it gave him that soft, tingly feeling every time he tried them on. He didn't feel like a girl, but he felt somewhat comfortable with the clothes he tried on. Cross-dressing in secret in his room made him feel anxious, however. There were a few close calls with his mom and sister, but he knew it would only be a matter of time before someone caught him, and he hoped to God it wouldn't be his parents.

Then the day finally came when his secret was discovered. It was Laundry Day for Terry and his sister, Mariah. He had snuck another skirt into his basket and carried it into his room, to try it on. Terry had just put the skirt on and looked at himself in the mirror for a good moment when he suddenly heard the door knock. "Frick!" He quickly took it off and grabbed his shorts from the bed.

Mariah called through the door, "Terry, can I talk to you?"

"Uh, hang on, getting dressed!" He puts his shorts back on and buried the skirt into his basket before sitting at his desk. "Okay, come in!"

Mariah opened the door to enter, closing the door behind her. "Have you seen my new skirt? I put it in the dryer before lunch, and now I can’t find it."

"Did you check with Mom?"

"I did, but she said one of you boys must’ve mixed up the clothing again, and you did your laundry today. Can you check your pile for me, please?"

Terry sighed. "Alright, give me a moment." He searched through the basket to find the skirt he had just buried and pulled out her skirt. "Found it!"

Mariah seemed confused. "How come my clothes end up in your basket?"

Terry shrugged as a fake response as he handed the skirt to her. "Mix-ups happen, you know."

"Thanks, I guess," she said as she took the skirt. "But seriously, this is the fifth time this month I learn that my clothes are in your basket. Are you sure this is just a mix-up?"

"Yeah."
"Tell me the truth."
Terry snapped, "I am, okay?"

Mariah flinched for a bit at the tone of his voice. "Then why are you giving me a tone?"

"Cause you won’t leave me alone!"

"I just want to know what’s going on, Terry! You’ve been acting weird for the last couple of months, staying in your room and not letting people in, being silent most of the time, eyeing people in public like you’re afraid of something!"

"What I do is my business, not yours!"

"Terry, I’m worried about you! I know you’ve been feeling down about yourself, but all the sudden you’re shutting us away as if we don’t want to know something!"

"Just--!" Terry couldn't speak another word as he sat down on the bed, holding his head in frustration.

Mariah slowly approached his side and sat down next to him, speaking in a soft tone, "Terry, you’re my little brother… and I care about you. It hurts to see you this way. I just want you to tell me the truth. Whatever it is, I won’t hold a grudge against you. Just talk to me…."

Terry sat in silence for a minute, afraid to even say a peep, before slightly looking toward her. "Promise you won’t think I’m weird…?"

Mariah nodded. "I’ll try my best…."

Terry took a deep, shivering breath. "…I stole your clothes and put them in my basket. Before you get mad at me, let me explain why. You see… I don’t know why, but… after I found your skirt in my basket one day and tried it on to tease you, I…" He paused for a moment, sniffling. "…I kinda like it. I don’t know why, but when I try on any girls’ clothes, I feel like… like I’m looking at a different person, someone better than the old me. I don’t really see me as a girl, though (don’t you even think that’s what I meant), but I still see someone better than this me." He sniffled again, tears beginning to stream down his face, before taking in another shaky breath. "I don't.... I don't know what's wrong with me. I don't know who I am or what I becoming anymore."

Mariah was astonished, clearly not expecting the words that came out of his mouth. She could see that he felt so confused, unable to grasp his identity, and she pulled him close.

Terry sobbed. "I... I just seem like a total weirdo right now. Admit it."

Mariah processed that for a moment before replying to him, "Well yes, I’ll admit it’s a little weird, but… to be honest, I don't think that's bad."
Terry looked up in confusion. "How?"

"Well, maybe this “weird feeling” you’re getting is a way of rediscovering your identity, whether for better or worse. There are others out there in the world who I'm sure have felt the same way you feel right now. Guys who cross-dress and like it a little. Maybe you're one of those guys. You won’t know unless you try and take a chance. Who knows, it might make you happy."

Terry sobbed again. "B-but… if this is what I want to do… what will Mom and Dad think of me…? What about Alex?"

"We’ll find a way to talk to them about it, but if this is what you wanna try to do to be happy again, I say you should totally go for it."

"W-what about you?"

"You’re my little brother, Terry. I want you to be happy again. You may not turn out to be the same Terry I grew up with, but you’ll always be the little brother I love...."

A few more tears streamed down Terry's cheeks as he hugs his sister tightly.

Mariah held him close, brushing his hair through one of her hands softly and rubbing his back with the other.

It took a couple of minutes to comfort him until Terry finally spoke, "I… I love you, big sis…."

Mariah smiled and nuzzled his ear. "I love you, too, lil brother."

They spent another minute in the hug of comfort until Terry spoke again, "Mariah?"

"Yeah?"

"Promise you won’t tell Mom and Pops until I'm ready to, okay?"

"I Pinkie promise," Mariah said as she did the Pinkie promise as shown by Pinkie Pie in MLP.

Terry smiled a little. "Thanks…"

"And promise you’ll stop stealing my clothes, okay?"

"I won’t, I promise." Terry did the same promise in silence.

"Good." Mariah giggled as she booped his nose. "How about we go shopping tomorrow so we can find you your own clothing~? Just the two of us."

Terry's ears perked up. "R-really?"

Mariah nodded with an assuring smile.

Terry smiled in return. "That... sounds like fun."

Mariah stood up and look at him. "We'll work it all out, lil bro, I promise. We'll make you the happiest fox in the city -- and the cutest."

They both giggled.

(To be continued...!)

Finally!
After 9 long months, I finally got around to drawing part 2 of Terry's transition from boy to femboy!
And since it's pride month, it seems logical to do it now rather than this upcoming September.
Next part will be his first time shopping for girly clothes! Don't miss it!

You can find part 1 of his transition backstory here --> fav.me/dbo7epr

Terry and Mariah Nightpaw and art (c) 2018 RedHoofsketch