James to Jamie

I’m James, and I was your standard young academic student. Average height, average build, average features. Longer brown hair, and a clean shaven face. I lived with my mother, and my older sister, Jenny.

Jenny was typical as well. She played soft ball, went to dances, and while she enjoyed attention from guys, she never got around to dating them.

I don’t recall everything that lead up to it, but growing up I found myself uncomfortable. I didn’t make many guy friends, and my girl friends would, not on purpose, put me on the outside of the circle. They were friends, and I was the friend of their group, more than anything.

I didn’t know the words for it back then, but I wanted to be better friends with them, or at least feel what it was like to be one of them.

That’s how I found myself in my sisters room. She was babysitting for the evening, and my mother was out on the town.

I had undressed in the bathroom, and leaving all the doors open between myself and there, began to go through my sisters closet.

Going through the items I picked out a baby blue tank top, much softer than anything I would wear, and a frilly, dark pink, skirt.

Setting them aside I went to her dresser. Opening the top drawer I found a ***********ion of bras. Sorting through them I picked the black one, with pinkish red lace flowers around the cups. Going down a drawer I found her panties, bikini on the left, thongs on the right, and assorted in the middle. Pulling out a bright red thong I quickly figured out it wouldn’t work with my assets, and I exchanged it for a black pair of bikini cut, with matching pink and red lace around the trim.

Feeling the panties in my hand, they were soft, smooth. The lace was a little rough, but so light as to tickle more than scratch, if anything.

Sitting on the side of the bed I rub the underwear between my fingers, before bringing them up and nuzzling my cheek in to them. Soft.

Picking up my feet I slide the panties up, tucking my penis back to make them fit. They were snug, but comfortable.

Standing up and walking to my sisters mirror I turn around, looking at my butt. My cock gives a slight twinge, and I see the fabric bulge.

Returning to the bed I begin my fight with the bra. Putting my arms through the loops and reaching behind me I fail to clasp it. Turning it around, backwards, I clasp it in the front before moving it back again, and replacing my arms. Feeling the empty cups protrude from my chest both felt right, and wrong.

Returning to the dresser I pull two sock balls from the bottom drawer, and fill my bra. Much better.

The skirt goes on easy, probably sideways. Without tags, pockets, or a zipper, I have no idea how girls figure it out. Returning to the mirror I look at myself from behind again. Wiggling my butt I love how the fabric dances around. Bending forward, touching my toes, I can barely see the hint of my black panties peak out from the longer than desired skirt. Again, the fabric bumps as my erection is now straining at the panties gusset.

Returning to the bed for the second to last time I slide the soft tank top over my chest. The straps fit comfortably on my shoulders, not putting any weight of the draped garment around my neck. Looking down my bra can faintly be seen through the light weight fabric.

At the mirror I feel my breasts, breasts, not socks. They don’t feel like real breasts, but they feel like mine, giving me the thought that I should have breasts, these aren’t natural, but I should have natural.

Sticking out my butt I run my fingers over the skirt, feeling how it flows off of me.