You

Susie looked around the room, surveying the various state of undress. “Well, it seems like David and I are the only ones totally naked here. I think we need to expand this from a ‘family’ thing to ‘friends and family’.” She smiled mischievously. “Hmm, who should I pick on? I think I’ll give David a chance to rectify this situation for our family. Ready, bro?”

“Sure, sis. I’m all ears.”

“Ok, I dare you to take off Carly’s bra and panties,” she pronounced.

“That’s not much of a dare,” I smiled. “I’d be happy to do it.”

“But there’s more,” she added with a sneaky look. “After you take them off Carly, you have to put them on yourself.”

I looked at her in shock. The girls all giggled. “Really? Now you trying to turn me into a cross dresser? Now I’m not sure I like this dare or not.”

“So, you want to forfeit?” Susie asked.

I figured that would be something even worse. “Nah, I’ll do it. It’s all in fun, right?” I got up and walked over to Carly. The thought of getting her naked made my already hard cock even harder as it swung out in front of me. “Ready?” I asked Carly as I reached behind her back to unsnap her bra.

“Sure, David, she smiled sweetly. “I can’t think of anybody I’d rather get me naked.”

Her encouragement was all I needed to get over my momentary trepidation. I unhooked her bra in the back then pulled it forward toward me revealing her c-cup boobies. “Wow, Carly,” I was surprised by how full and round they were. “Those are beautiful.”

I started to reach for them but my sister shouted out “No!”

“What?” I turned to look at her.

“There was nothing in the dare about touching her boobs. Now put on her bra!”

“Now?”

“Yes, right now.”

I frowned but I proceeded to do as she said. I’ll admit that this wasn’t the first time I had put on a bra. As an adolescent I had tried on some of my mother’s things out of curiosity. Still I wasn’t used to it and struggled putting my arms around my back to fasten it.

“Jeez, stupid boys!” Carly laughed. “You’re doing it all wrong!” She reached out and pushed the bra straps off my shoulders then spun it lace garment around until the hooks were in the front. Then she hooked them together, spun it back around and put the straps back up over my shoulders. As she did, she leaned up against me, her firm breasts pressing against the bra on my chest.

“Come on, David, quit stalling. Take off her panties and put them on,” my sister shouted.

Carly stood up and I reached out and grabbed the waistband of her pink lace panties. I pushed them down her legs, they were kind of rolled up by the time I pulled them off her feet. She had a small landing strip of dark hair above her pussy.

I didn’t have much time to admire it, as my sister shouted, “put them on, David!”

I fumbled around a bit getting them uncurled then pulled them up one leg then the other. I tried to tuck my rigid member inside them with little success.

“Just leave your cock and balls out,” my sister instructed me. “Why would you want to hide them now?”

Carly sat back down and I just shrugged my shoulders and went back to my chair. It felt weird sitting there in a girl’s underwear, but at the same time pretty exciting.

“So, sissy boy, you going to pick someone else now or just sit there looking pretty?” my sister teased me.