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Chapter 5

What happens next?

Emma catches you in panties

When Emma heard you say you’re going to change, she decided she wanted to get a peek of you while changing. After you closed the door, Emma had creaked the door open, hoping to get a view of you naked.

What she sees, though, is something completely different. As she sees your bright pink panties, she throws caution into the wind, busts the door open, and says “John, what are you wearing?”

“Ahh!” You scream, covering your crotch area. Nobody was supposed to see this, especially not your best friend. “Uh, Emma, I-I-I- can ex-p-plain…”

She interrupts you abruptly. “What are you wearing, John?” She repeats. “Show me.” She says.

There’s no way out of this. You slowly lift your hands and reveal the bright pink panties that cover your crotch. There’s a pause of silence, as Emma stares at you.

Suddenly, you hear your mother yelling, “John! I have to take care of something at work! I’ll see you later tonight!” You hear your mother slamming the front door.

Emma plainly says, “Come to the living room with me. We need to talk.”

Uh-oh. You can’t even tell if she’s mad, upset, or something else entirely different. You follow her to the living room and sit next to her. She looks at you with a bit of a weird expression. “You know, you could have put on clothes before you came out.” You blush a deep red and fumble on your words. She quickly says, “Whatever. We just need to talk.” You can tell her tone has changed to be a mix of concerned and confused. She stares at your almost naked body as she says, “Be honest with me, no lies. Why didn’t you tell me you liked crossdressing?”

“I don’t know… this was my first time.” You say. “It was a spur-of-the-moment kind of thing, kind of.”

“I guess I can understand that. Everyone gets curious.” She says. “Do you wanna try more?”

“Huh?” You say

“Do you wanna try and dress fully as a girl, to see what it’s like?” Emma says. She twirls her curly red hair as she awaits your answer.

You’ve never thought this was how she’d react, but something inside you tingled at the thought of dressing up like a girl. “Sure?” You say. It sounds more like a question as you say it.

“Come on! It’ll be fun! Follow me.” Emma says as she grabs your hands. “Don’t worry. Nobody’s home. It’s just you and me.” She drags you over to your sister’s room. She starts rummaging through Jane’s drawers. You stand there, still mostly naked. You blush a deep red as you wait for Emma to hand you something. Eventually, she pulls out a bright pink bralette. She tosses it towards you saying “This is the one that matches your panties. Put it on.”

“O-ok.” You say shyly. You slowly put on the bra. It has no hooks, so it is quite easy to slip on. There’s no extra padding in the bra, so it sits flat on your chest. Just like the panties, it feels nice and smooth against your skin. You want to relish in the feeling of the bra, but still, feel uncomfortable being mostly naked. You stand there and cover your chest with your arms.

Emma looks back as she continues to rummage through Jane’s drawer. “Relax, John! We’re both girls here.”

The sound of her saying that makes you tingle for some reason. You’re not sure how to feel about being called a girl. “I-I’m a boy, though. This is just some f-fun!” You say.

“Sure.” She says flatly. Suddenly, she pulls out a long, red dress. “Ooooh!” She says enthusiastically. “I think this would look cute on you! Come over here, I’ll help you!”

You’ve never thought you would go this far. “I’ve never worn one of those, Emma you say shyly.

“Come on! If you’re gonna dress like a girl, you gotta go all the way!” Emma says.

“Okay.” You mumble.

You waddle over to Emma and she holds the dress up. “Step in!” You follow her lead as you slowly step into the dress. She then pulls the dress up your body. As she does, you can feel her soft hands sliding against your skin. “Arms!” She commands. You stick your arms through the sleeves and feel the dress against your arms and shoulders as Emma continues to pull it up. You do your best to suppress moans as she finishes putting the dress on you.

You hear her zip up the back of the dress as she says, “Done! You look so cute! You gotta go look at yourself!” You walk over to your sister’s full-length mirror and look at Emma’s work.

You have to admit, you do look kind of cute. As you look at yourself, you take a moment to notice how the dress fits and feels. While it’s a little loose around the chest, it fits nice and tight below the chest all the way to your waist. The skirt starts right at the waist and ends just above your feet. Your shoulders and chest are all covered by the dress, as well. The sleeves end just at your mid-bicep and are nice and loose. The dress is very comfortable to wear, especially compared to what you usually wear. It feels really nice against your skin, and the looseness of it allows you to move your legs freely. Overall you still look like a boy, but a very pretty one at that. The way you look… the way you feel… everything makes you feel so cute.

“So, what do you think?” Emma says.

“It feels… nice.” You say softly.

“I knew you’d like it!” She walks up to you and hugs you from the front. Just like before, you can feel her perky breasts push against you as the two of you embrace. “Oh, this is fun! You should be a girl all the time!” She lets go of you, and for a minute, she just looks at you.

The feeling of the dress, the way you look in it, and Emma’s eyes on you all make you feel excited. You get a little too excited, and you can feel the blood rushing to your penis. You feel your tip push hard against the fabric of the panties. Your rock hard penis makes a tent in your dress, and Emma spots it immediately. “Wow John! I guess you really like it!” She lets out a playful giggle as she stares at it. You blush and cover your crotch area with your hands. She places her hands on your shoulders and says, “It’s okay, I get it.”

Emma looks at a clock from across the room and says, “Look at the time, I have to go! You can come over to my place tomorrow if you want to. I’ll be hanging at my house.” You follow her to the front door, nearly tripping on your dress as you walk. You stop right at the front door, and she looks you up and down one more time. “Bye, John!”

“B-bye!” You say shyly. You are still blushing fiercely at the whole situation.

Emma gives you a wink and in a flirty tone whispers, “Oh, and don’t worry. I won’t tell your mom about this.” She turns around and heads out the door, smiling.

As she leaves, you stand there for a minute. You let out a huge yawn and realize how tired you are. You could fall asleep right now. It’s been such a busy day.

What do you do next?

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