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Rated: 18+ · Interactive · Erotica · #1831087

Cameron somehow finds himself in a crossdressing situation. Gift Points for good chapters!

This choice: Anna offers to help  •  Go Back...
Chapter #7

Anna offers to help

    by: DragonFish Author IconMail Icon
Cameron hesitated, his face still flushed with embarrassment as Anna studied him. After a moment, she let out a small sigh and crossed her arms.

"Alright," she said. "If you're really curious, then let's do this properly. I’ll help you."

Cameron blinked. "Wait, what?"

Anna rolled her eyes. "You clearly want to know what it’s like, right? You don’t have to sneak around or feel weird about it. I’m your sister, and I’m not going to judge you for being curious. So, if you’re up for it, we’ll do this the right way."

Cameron opened his mouth to protest but hesitated. If he backed out now, Anna might think he was lying and accuse him of being a pervert. That would be so much worse. He swallowed hard and gave a small nod.

"Okay... I guess."

Anna grinned. "Good! Now, wait here. I think I have something that’ll fit you."

She rummaged through her dresser for a few moments before pulling out the same pair of white lacy panties with a cute little bow on the front that Cameron had been trying to return, along with a matching bra. She then grabbed a pleated skirt and a simple fitted top. The top was soft and snug, made of lightweight fabric that hugged the torso, while the skirt flared gently from the waist, its pleats giving it a playful bounce.

Cameron eyed the clothes, feeling his nerves spike. "Do I really have to wear all of it?"

Anna raised an eyebrow. "You don’t have to do anything. But if you want to really see how it feels, you might as well go all in. No pressure, though."

He hesitated but ultimately nodded. "Alright… just for a little bit."

Anna handed him the clothes and gestured toward the bathroom. "Go change. Take your time."

Cameron took the bundle and stepped inside, his heart pounding. As he slipped off his usual clothes, he held up the lacy underwear he had originally been trying to return. The fabric was delicate, softer than anything he had ever worn before, smooth and light in his hands. As he stepped into the panties and pulled them up, the snug fit and the gentle pressure against his skin sent an odd shiver through him. The lace hugged his hips in a way that felt both strange and strangely comfortable.

Next, he hesitantly clasped the matching bra around his chest, adjusting the straps. It felt foreign—light but slightly constricting, like a gentle embrace around his torso. Every movement reminded him of its presence, an unfamiliar yet oddly reassuring sensation.

He then pulled on the top, the fabric stretching softly over his frame, following the contours of his slender torso. Finally, he slipped into the pleated skirt. As it settled around his waist, its airy swish against his legs made his stomach flutter. The lightness of it, the way it moved with every shift of his hips, was so different from the jeans he was used to. He brushed his hands over the fabric, feeling the texture, the weight—or rather, the lack of it.

Taking a deep breath, he stepped back into Anna’s room. She looked up and smiled softly. "See? Not so bad, right?"

He shifted awkwardly but managed a small smile. "Yeah… it’s different. But… not bad."

Anna nodded approvingly. "Alright, now let’s see what else we can do to make you comfortable."

You have the following choices:

*Pen*
1. Makeup and Accessories

*Pen*
2. Christina's Help

3. Hanging Out

*Pen* indicates the next chapter needs to be written.
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