Sisters Assistant TG

Daniel couldn’t believe he’d agreed to be his sister’s “personal assistant” for the week. At first, she’d promised he’d just be handling some errands for extra cash, and it sounded easy enough. But as he stood in her bedroom, staring at the outfit she’d laid out for him, he realized he was in for something far more humiliating.

“Are you serious, Claire?” he stammered, holding up the flimsy, nearly see-through fishnet bodysuit. The black fabric was delicate and tightly woven, promising little in the way of coverage.

Claire crossed her arms, smirking. “Of course, I am. You want to get paid, don’t you? Besides, a real assistant dresses according to their boss’s standards.”

With a sigh, Daniel reluctantly stripped and began pulling on the bodysuit. The stretchy material clung to his skin, sheer enough to expose his torso while accentuating every line of his body. Black fishnet elbow-length gloves completed the outfit, adding an extra layer of absurdity to the look. But the worst part? The breastforms.

Claire carefully applied a liberal layer of glue and pressed the breastforms to his chest, positioning them so they filled out the fishnet, though they jutted at a slightly awkward angle. Within minutes, Daniel felt them starting to slip, and he instinctively cupped them with his gloved hands, his face heating with embarrassment.

“Perfect,” Claire said with a grin as she clipped a long brunette wig onto his head, adjusting it until it cascaded over his shoulders. “Now for the finishing touch.” She pulled out her makeup kit, lining his eyes with a smoky black eyeliner, brushing blush across his cheeks, and slicking his lips with a glossy red lipstick. By the time she was done, Daniel barely recognized himself in the mirror. He looked… disturbingly like a girl, though a clearly uncomfortable one.

“Alright, ‘Danielle,’” she said, savoring the nickname, “let’s get started. First task: go clean out my underwear drawer. I want everything organized by color and style.”

Swallowing his pride, Daniel trudged over to her room, awkwardly cupping the slipping breastforms with his hands as he opened her underwear drawer. The sight of the colorful lace panties and bras made his cheeks burn, but he knew better than to argue. Carefully, he sorted through the items, arranging everything as instructed, all while trying not to think about how ridiculous he looked.

“Very nice,” Claire said, inspecting his work. “Now, for your next task…” She pulled out a box from under her bed, opening it to reveal a small collection of toys—dildos, vibrators, and other “accessories.”

Daniel’s eyes widened. “You’ve got to be kidding me, Claire.”

“Nope. I want you to test these for me,” she said with a wicked grin, holding up a pink vibrator. “Just check the battery levels and make sure they’re all working. It’s important they’re in prime condition.”

Grimacing, he pressed each button in turn, the toys vibrating and buzzing in his gloved hands, sending tingles up his arms as they hummed loudly in the quiet room. Every hum felt like a further dive into humiliation, his cheeks blazing as he handled each item.

“Great job,” she said with a satisfied nod. “Now, I have a package that needs delivering—to my boyfriend. And you’re going to bring it over, looking just like this.”

Daniel gaped. “You want me to go out like this?”

“Oh, absolutely,” she replied, handing him a small pink bag. “And I want you to strut. Show a little confidence, Danielle.”

Trying not to think about how ridiculous he looked, Daniel took the package and headed out, the wig brushing against his shoulders with every step. He managed to make it down the street and up to the boyfriend’s door, holding the bag out with his gloved hand and avoiding eye contact as he stammered, “Delivery from Claire.”

The boyfriend chuckled, taking in Daniel’s outfit with obvious amusement. “Thanks, ‘Danielle.’ Maybe I’ll see you around again?”

Daniel forced a tight smile, feeling the breastforms slipping yet again as he hurried back to Claire’s. When he finally returned, she looked him over with a self-satisfied grin.

“Good job. I think I’ll have to keep you around a bit longer,” she teased.

And by the end of the week, Daniel knew he’d never be able to live down the humiliating tasks—or the outfit—Claire had roped him into, all for a bit of “extra cash.”