Dolly Dress Up

You and Elsie burst into Peggy's room full of laughter and youthful exuberance. God, you felt so alive! You never would have known you had a virus in you had you not been tested.

Spinning Elsie into your embrace you plant a long deep kiss on her and she melts in your arms. You let it go and in tandem you both let out a happy sigh. You let her slip from your arms and the pair of you just stare at each other, love drunk and infatuated.

Finally El reaches out and traces her fingers down your bare chest. You had almost forgotten that you were still nude. Never before had being naked in front of others felt so natural and right.

"Jesse."

"Yeah?"

"Peggy doesn't have any men's clothes. Is that okay?"

"Yes Princess."

She giggles. "Thank you Cutie." Her voice lowers to a whisper. "I think boys look really hot in lingerie. Especially when they have a nice body like yours."

You bow your head. "Yes Princess." She goes to pull away and head toward the closet but you take her hand. "El."

"Yeah?"

"You...don't think less of me? For all of this? Me being a dress up dolly and putting on shows and just...this stuff. Do you?"

"Less of you?" She seemed utterly perplexed by the question. "Jesse, no. Of course not. You're my big brother Jesse, I adore you!"

You let out a breath of relief. "That's good."

She strokes your arm. "We are so alike you and me. I was just thinking the same thing. I was worried you would think I'm weird for treating you like this. Aren't we silly?"

"El." You take a deep breath. "I...I want you to be my first. The first to...be inside of me, to take my virginity. I want to give myself to you first."

"Inside...!? Oh! Oh my goodness." She is holding back tears as she nods her understanding. "Thank you Jesse."

"It is my honor."

"I...don't want to hurt you." She whispers.

"You won't. I want you, I need you, to be my first. It's...very important to me."

"I understand. More than you know." She trembles and for a moment you see a great sadness wash over her. "I wanted you...to be...my first."

As important as this was things were getting too serious again, bringing levity back into your voice you add. "But only after I beg good enough. If I beg at all that is. Pah! As if!"

She titters and brightens and wipes a joyful tear from her eye. "Of course! Ohh you'll beg alright! Oh how I'll make you beg! I'm strong! I'm mean! I'm a bad ass bitch and a kick butt Domme who...pffft! Ha ha ha ha!" She can't hold it together for her tough girl act to be convincing but it only makes you fall in love with her that much more. "Anyway, yes! Definitely!"

You hug one more time then let go to let her dress you.

She goes to Peg's closet and slides the double door apart revealing a spacious walk in closet. She flicks on the light inside and begins to explore. She then snaps her fingers. "Shoot! I forgot."

"Huh?"

"Close your eyes. We have a surprise for you."

"You have a...?"

"Cutie." She says in her warning voice as she plants her fists into her hips and gives you a stern look. "Be a good boy now."

"Yes Princess." You grin and obey. Closing your eyes you stand and wait.

There is silence followed by some rummaging around and then more silence as you hear Elsie fiddling with something.

"Hah!" You gasp as you suddenly feel a cold metal ring slide up and around your cock and balls. This is instantly followed by the sensation of cool steel rings slipping over your now mostly flaccid dick. Click! The sound of a lock clamping closed.

"He he he!" El titters. "It's a little big for you, it used to be Chloe's, but it will do the trick. You can open your eyes now."

You look down to see your manhood securely contained inside a stainless steel chastity cage. On the top a small but sturdy looking padlock held it all together. The key dangled from a slender gold chain which Elsie was currently clasping around her neck.

"Peggy said you would beg better after a few days of wearing this." Elsie checks it over, making sure it is comfortable and that you had no hope of escape. "I'll miss seeing your cute little peen get hard but these are the sacrifices we make for those we love."

"A few...DAYS!?"

Elsie nibbles her bottom lip. "Don't worry my Cutie Doll, there are other ways of having fun."

"But..."

Her smiles fades. "Don't you like it?"

"I...uh...what if I have to...uh..." You let out a huff. You trusted her, El wouldn't do anything to hurt you. Bowing your head again you say. "Thank you Princess. I love it."

Watching her smile brighten once more made it all worthwhile.

She returns to the closet. "I wish Peggy liked pink more. I think you'd look so good in pink. Black and red are so unimaginative. Hmmm, green or blue?" She looks back over her shoulder.

"Green please."

"Good choice!" She reaches into a drawer and begins pulling items from it. It's a lingerie set of a light mint green along with lacy white thigh high stockings.

Taking the panties first she comes and kneels down in front of you. You step into them one foot at a time then El pulls them up. She gets them just right then steps back to admire the sight. The skimpy lacy panties felt so soft on your skin. You wished your cock wasn't caged so you could feel it there as well but there would other opportunities for that.

Elsie gives you an approving nod then gets the bra. "Sorry, we don't have your size. We'll have to do some shopping."

"That'll be fun." You grin as you watch her oh so attentively put the bra on you. "We should take Mom with us."

"Yes! Oh my god she would die of happiness if you let her go bra shopping with you."

"I got that sense." You chuckle. "Maybe we should send her a picture right now."

"Ha ha ha! No! That would be so mean!" El belly laughs. "She would break quarantine so damn fast it wouldn't be funny." She arranges the bra as best she could. There is space left in the cups though it still looked pretty good, thankfully Peg wasn't as stacked as your mom and sisters.

Next comes the garter belt. It is a tight fit but for once your slender body worked to your advantage. Then she brings the stockings and pulls them up your leg, first the right and then the left. As with the bra and garter belt the fit isn't perfect, though this time the fit is a little loose. Aunt Peg had some serious quads and calves on her due to her exercise regime. They do fit well enough to stay up and once the garters are clipped by the straps of the belt you couldn't even tell they weren't quite your size.

"Daaaamn brother, you are looking fine!" Elsie crosses her arms and takes a good long look at you.

You check yourself out in the full length mirror in the corner. Fuck! You were looking fine! You were shocked at just how hot you looked in it. Women's attire really suited you. It was going to be fun experimenting with this stuff.

"Do you want make up?" El asks.

"Um...what do you think?"

"Mmmm, maybe another time?"

You nod. "Whatever you want Princess."

"Can I brush your hair again?"

"I'm your Cutie Doll. Do what you want."

She rushes to the vanity with a hop to her step. Taking a hairbrush she comes back to you and sits you down on the bed with her kneeling behind you. You stare into the mirror as your sister brushes your hair in long even strokes. The bristles feel good gliding along your scalp. Again you marvel at just how happy she looked, how at peace. She loved attending to you as much as you loved having her do it.

You then notice the smell of garlic. "Wonder what's for dinner?"

"Knowing Peg something super fancy that's hard to pronounce."

In your best impersonation of your aunt you say in a haughty tone. "You mean Crostini with Prosciutto and Ricotta?"

"Pffft! Ha ha ha! I called it ham and cheese on toast. I felt so stupid."

You laugh along with her. "Hard to believe her and Mom are sisters."

Elsie finishes with your hair and kisses your shoulder. "You look so good. Okay, lets go back."

"El?"

"Yeah?"

"Are you going to dress me every day that I'm your Doll?"

"Ummm, yeah?"

"Oh good." You smile. "I like this."

She grabs you in a big hug from behind and squeezes you tight. Reaching back you grab her legs and with a grunt rise up from the bed taking her along with you piggy back style, just like when you were little.

"EEEEE!" She squeaks with girlish delight as you spin her around. "Yes my steed! Take me to Peg!"

With a whiny and a trot you start back for downstairs with your Princess on your back.