Shopping Spree

You walk over to look over some bras with Elsie. The ones she pointed out were fairly plain with just a little pink bow in the middle. This particular kind had just a bit of padding to simulate a petite AA cup breast.

El says. "Just a smidge of curve, it would look SO good on you. I don't think you want to go too big."

You nod enthusiastically. "Yes! Just subtle. Petite."

Elsie giggles. "I think Mom's getting excited again."

You look over and catch her stealing a thirsty glance in your direction. When she sees you looking she just smiles and waves. You whisper. "I think she wants my little tushy again." You titter.

"She's not the only one." El motions behind you. You see the two gay gentleman approaching, obviously on the make.

The greet Elsie kindly but all of their attention is on you. "Hey, never seen you here before."

Elsie offers again. "It's her first day."

"Yeah, we overheard. Jesse was the name, right?" They were both probably mid 20's, in good shape, and had a good casual fashion sense. Blue jeans and trendy jackets. One was black and one was white.

You were incredibly uncomfortable by their attention. "Uh...hi...yeah. Sorry, I'm busy shopping. Er, we are...um..." You stumble over your words, you felt like an idiot. "I...uh...I'm a lesbian. Go away please!"

They raise their eyebrows at your bold rejection of them before they had even started, they look at each other. They were disappointed but they were picking up your obvious signals of disinterest in them. "Okay Jesse. Have a nice day girls." The pair wander off, chatting with each other as they went.

You let out a sigh of relief. "Whoo..."

El was grinning. "You could have had a date, they looked nice."

You give her a serious look. "El...I'm not...I'm not gay. I don't think. I just..." Your thoughts and emotions were swirling. You take a deep breath. "...I don't know..." Your brow furrows in your confusion. "I like...how you guys are..." The problem with liking people like your family, is they were the only ones!

Elsie strokes your shoulder. "Hey, we're here to shop. You're right, let's shop."

The next hour and a half is spent trying on a plethora of women's clothes. Everything from classy to slutty to everyday to cute. In general you settle on cute. These clothes were tailored to emphasize certain things and de-emphasize others, the make and cut of each one designed to make the masculine look feminine. The padded bra absolutely completed the illusion. Looking in the mirror you had to look really close to see the boy you once were. You didn't have a prominent Adam's apple. Really it was just the width of the shoulders was a touch too much. As you try on outfit after outfit you just felt better and better. You looked good, you felt good, your family was happy and together. Even Fiona had returned to watch you parade your styles for them. Each had their own tastes and their own ideas. Each time you stepped out you would get a mixed reaction. It was such a great family bonding moment, the four of you together. Chatting, laughing, bonding. All of them helping you with what was potentially one of the most important days of your life.

At one point, with a nice checkered skirt and white blouse, you say. "This one is very practical." You look at your gathered family. "I think I'll wear it to school tomorrow." You wait to watch their reactions.

Your worried mother and Fiona look to each other, Fiona had a look of 'I told you so!' El is smiling but concerned.

"That's...that's a big decision Jesse." Your mother says in a gentle tone. No one else says anything. You turn back to admire yourself in the mirror. You were going to turn some heads tomorrow!

Your mother spoils you. Allowing you to get five more full outfits on top of the three she had already bought for you online. You also get a wide assortment of panties, bras, stockings, shoes, etc. It was like a birthday. In someways it really felt like one.

Aaron bids farewell to the Bailey clan. Special attention given to his friend Fiona. He takes you aside before you leave. "Jesse, you'll face some challenges out there. Just remember cupcake; you're special, you're beautiful, you're powerful. Don't let anyone tell you otherwise, okay?"

You grin. "Thank you Aaron, I am sure I will see you again."

He pats your cheek again. "I'm sure."

Walking back to the vehicle you are walking with pride. You were experimenting with it but you start to learn to sway your hips as you strut. You had never felt more alive.