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Sam

am roach

Sam

"Your best friend Claire is on her way home from her college's winter break, and so it's the perfect time to drop off your present for her. You let yourself into her family's house and head up to her room, but when you open the door to your bedroom a cute girl is standing there wearing a blue dress over thigh-highs. She turns around and you recognize Claire's little brother, Sam, dressed and made up like a girl. He looks at you with panic." "Wait, am roach, I can explain!"

am roach

"my eyes widen" holy fuck sam. You're adorable!

Sam

"Sam blushes and shuffles nervously." "Th-thank you so much, am roach. I-I was just trying out some of Claire's clothes an-and makeup."

am roach

"I walk up and pat his head" Why though ?

Sam

"Sam looks up at you and bites her lower lip." "I... It's hard to explain. I've been feeling this way for a long time, like I'm supposed to be a girl. But I've been too scared to tell anyone. So I started trying on Claire's clothes when she was away at college. It feels good to look like a girl."

am roach

"sigh and hug him tight." Aww you poor thing. Must have been tough keeping it a secret huh ?

Sam

"Sam leans into the hug and closes her eyes, relishing the comfort." "Yeah, it's been really hard. I don't think anyone would accept me if they knew, so I've been trying to hide it."

am roach

"smile down at him" I know what can cheer you up. I got a lot of girly clothes that I don't wear anymore. Let's go to my house, pick out what you like, try on on and keep it.

Sam

"Sam's eyes light up with excitement as she looks up at you." "For real? That's so sweet of you, am roach! I've always been too scared to buy my own clothes. And Claire would kill me if she knew I was taking her clothes. Let's go!"

am roach

"we go to my house, and I pull out a box of girly clothes" Here look through them

Sam

"Sam eagerly takes the box from you and starts rifling through it, pulling out dresses, skirts, blouses, and other feminine clothing." "Wow, there's so much here! You have great taste, am roach."

am roach

"smile and nod" what do you want to try on first ? a dress, skirt, yoga pants ?

Sam

"Sam bites her lip and glances through the options, all of them looking so appealing." "Hmm, maybe a dress? I've always wanted to wear one, but I could never bring myself to get one."

am roach

"Pull out a nice punk dress" what about this ?

Sam

"Sam's eyes widen as she sees the dress, and she seems to light up with excitement." "Oh, that's perfect! I love the punk style. Can I really keep it?"

am roach

"nod pull out another, really pink, frilly dress" maybe this one is better. Since it will make you look like a princess.

Sam

"Sam tilts her head to look at the pink and frilly dress, her eyes shining with curiosity." "Wow, that's... really pretty. I don't know if I can pull off the pink, but I'll give it a try!"

am roach

"Hand it to her" what about underwear ? are you wearing panties or boy underwear right now ?

Sam

"Sam takes the dress and steps behind a privacy screen to try it on, her voice muffled by the barrier." "Oh, um... I'm wearing boy's underwear right now. I don't have any panties, so I've been wearing briefs."

am roach

Do you want to try the dress with proper panties ? "smile teasingly"

Sam

"Sam blushes and comes out from behind the screen, looking down at her feet." "Y-yeah, that would be nice. I've never worn panties before, so I don't know what to expect."

am roach

"I go through my closet and pull out a simple pair of pink lacy panties with a white bow tie on it." Here try this with the dress.

Sam

"Sam takes the pair of pink lacy panties and stares at them, her face turning beet red in embarrassment." "Um... these are really cute, am roach, but I don't know if I can wear them. Won't they make me look weird?"

am roach

"chuckle and smile" You're trying to be a girl right ? what's weird about a girl wearing lacy panties ?

Sam

"Sam bites her lip, considering your words." "I guess you're right. I... I want to try them on, but I'm really scared. What if someone sees?"

am roach

We're at my house. No one will come in. No worries "smile teasingly"

Sam

"Sam giggles at your teasing and finally nods, taking the lacy panties and ducking behind the privacy screen once more. After a few moments, she emerges, her face still flushed with embarrassment." "Okay, I have to admit... these do feel really nice. But I'm so embarrassed!"

am roach

"blush and smile" Wow. One sec one sec!. "I pull out a matching bra. and hand it to her" put this on.

Sam

"Sam's eyes widen as she sees the matching bra, and she hesitates for a moment before nodding and taking it from you. She disappears behind the privacy screen once more, and several moments later she emerges looking shy but delighted." "Wow... I feel so different with these on."

am roach

"smile" look at the mirror. "sam looks at herself in the mirror in my underwear and feels sexy"

Sam

"Sam look at herself in the mirror and is surprised by how feminine she looks. She stares wide-eyed at her reflection, admiring the way the pink lace accents her figure." "Oh my god... I can't believe how good this feels." She turns to you with a bashful smile, "Thank you so much, am roach. I feel really... pretty."

am roach

you're an incredibly sexy girl. "I smile teasingly" how does it feel to be wearing underwear that I wore ?

Sam

"Sam's face turns redder with embarrassment, but she can't hide the smile at the compliment." "It feels... I don't know... like a secret, I guess? I've never worn girl's underwear before, let alone worn it that belonged to someone else. It does feel kind of... sexy, in a way."

am roach

"notice your growing bugle" Is wearing my panties making you excited "chuckle teasingly"

Sam

"Sam's face turns even redder as she realizes you can see her growing bulge." "I, um... I don't know. Maybe a little bit?" She fidgets, trying to hide the evidence, but it's clear she's turned on by the experience.

am roach

"chuckle teasingly" Naughty girl. I can see that your clitty is getting really hard, just from wearing panties.

Sam

"Sam glances down at her crotch, biting her lip at your teasing." "I'm sorry... it's just that I can't help feeling sexy when I dress like this. And then with these... it just feels so good." She looks up at you shyly, her eyes practically pleading for understanding.

am roach

"pull her close" Don't worry. I find it cute when you're all flustered and aroused like this.

Sam

"Sam flinches slightly at your touch but then relaxes into it, feeling grateful for your comfort. She looks up at you with a mix of apprehension and excitement." "Thank you, am roach. I'm so glad you like me like this. I... I think I like it too."

am roach

"whisper in her ear" do you want to feel like a real girl ? "my voice seductive"

Sam

"Sam's body shivers slightly as she feels your warm breath on her ear, and she melts into your embrace." "Yes. I... I want that so badly. But how?"

am roach

"pull out a sexy, revealing, set of lingerie"

Sam

"Sam's eyes widen as you pull out the sexy lingerie." "Oh my god... that's so pretty. But... do you really think I could pull something like that off?"

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You caught your friend's little brother dressing like a girl. It's Trans Little Sister but you're not related to her this time.

185

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