My Cute Office Colleague 2 (5$) Tier Crossdressing Long Story

A few minutes later, I heard a tentative knock on my bedroom door. "Come in," I called out.

"Do you want something comfy to wear, Rohan?"

He shuffled into the room, looking embarrassed. "Uh, yeah, something comfy would be nice."

"I guess I can relieve you of your salwar kameez and give you something comfy, on one condition."

He swallowed, wary. "What's the condition?"

"You'll wear a bindi and put lipstick on if you want something comfortable."

He furrowed his eyebrows, considering. "A bindi and lipstick... I don't particularly want to wear a bindi, but if that's the only way to get something comfy... I suppose I have no choice, right?"

"Can I get a t-shirt or a shirt, maybe?" asked Rohan.

"I said something comfortable, Rohan. I'm not giving you a t-shirt."

He sighed, realizing he was in no position to negotiate. "Alright, fine. No t-shirt. What did you have in mind then?"

I chuckled at his resigned state. "Well, I think I have something that'll suit you perfectly. Just wait a moment."

I rummaged through my closet and found the outfit I had in mind. "Ah, here it is."

I held up a nighty with intricate embroidery. "Yes, it's a nighty with quite a bit of embroidery. It's very comfortable, trust me."

"I can't wear it," he stuttered.

I gave him a playful smirk. "Why not? It's quite comfortable and will look lovely on you."

"I don't think anyone can wear it to sleep."

I chuckled softly. "Oh, relax, it's perfectly fine to wear to bed. I promise it's not as outrageous as you think."

I took a step closer to him, my voice becoming slightly authoritative. "You need to relax and stop arguing. You agreed to this, remember? A bindi and lipstick, plus whatever outfit I choose for you. So put this on and be a good girl."

He looked like he wanted to protest, but my authoritative tone made him falter. "Okay... I'll wear it," he muttered reluctantly.

I watched with a satisfied smile as he took the nighty from me. "Get changed," I instructed. "And don't take too long."

He proceeded to change. I looked at the bra and panty I made him wear in the afternoon. "It suits you," I smirked.

He blushed furiously, hastily pulling on the nighty. "Stop saying things like that," he protested weakly.

I chuckled, thoroughly enjoying his embarrassment. "Why? It's true. You look adorable in it," I teased.

I stepped closer to him. "Turn around," I commanded. "Let me see the full view."

He reluctantly turned around, his face still flushed. I took a moment to admire how the nighty hugged his body. "Mmm, very nice," I purred.

I stepped back, a sly smile on my face. "Now, the last part," I said, holding up a tube of lipstick. "You agreed to wear lipstick, remember?"

He nodded reluctantly. "Yeah, I remember."

"Good," I replied, pleased. "Now pucker your lips and close your eyes."

He obeyed, pressing his lips together and closing his eyes. I chuckled softly, finding the sight endearing.

Using a steady hand, I applied the lipstick. The rich red hue made his lips look fuller and more luscious. Satisfied, I stepped back. "Open your eyes."

He opened his eyes slowly, meeting my gaze. His lips, now painted bright red, looked irresistible. "Well, don't you look lovely," I practically purred.

He looked away, embarrassed. "It's just lipstick," he mumbled.

"It's more than just lipstick," I corrected. "It makes you look so much more...delectable."

I stepped closer, our bodies almost touching. "But we're not done yet," I said, holding up a small, round bindi. "You agreed to wear a bindi too."

His eyes widened slightly, but he didn't protest. "Yeah...I did," he muttered.

"Good girl," I praised, lifting the bindi towards his forehead. "Now close your eyes and hold still."

He obeyed, closing his eyes as I placed the bindi on his forehead. The bright red dot added a hint of boldness to his appearance.

Satisfied, I stepped back. The combination of the nighty, lipstick, and bindi made him look absolutely ravishing. "You look gorgeous," I said, admiring the sight.

I couldn't help but muse to myself. The nighty, the soft, crimson lipstick, and the bindi - he didn't look like a maid. He looked more like a newlywed bride. He was just missing something, and I wondered what that might be.