It was the summer of my sixteenth birthday. It was when I first thought of girls’ clothing as the clothes I would like to wear.

My name is Matt and I live with my three sisters and mother. I am the youngest and as you may realize in this sort of set up, there is no shortage of girls’ clothing for me try on.

I had just turned sixteen and it was summer. As usual, the four beautiful women in my life were sitting out in the garden sunbathing in their bikinis. Mom and of the girls were even topless, their breasts exposed. It was no biggie to me, the girls often walked around topless.

I’m not sure what came over me, but I decided to go upstairs and look through my sister's drawers. I picked a few items of clothing and underwear and went back to my room. I locked the door behind me and laid my treasure on the bed. I stripped off, my little cock swinging free from my boxers.

I grabbed the first pair of panties and pulled them on. They were pink cotton briefs and they fit me snugly. I pushed my cock between my legs, wondering what it would be like to be a girl. I admired myself in the mirror, the pink panties making a contrast against my almost pale skin. There was no hint of my cock in them, which in turn turned me on and made me slowly get hard. My stiff cock against my own butt, between my legs, felt amazing.

I decided to carry on dressing up.

I took a cute flowery bra and did up the clasps from the front before twisting the bra around my waist and putting my arms through the straps and putting it on properly. The bra seemed a bit empty, so I grabbed some of my sock from my drawer and stuffed the bra till I looked like I had full breasts. I looked so sexy that I knew that I would soon have to jerk off. I pulled on some knee socks feeling the material ride against my thigh, making me feel deliciously naughty.

In a moment of madness, I picked up my phone and took a picture of myself. I sent the picture to two people, my two best friends, one a guy and one a girl. I decided to see if they would reply before I continued. It took only a few seconds for them to reply. She replied with a large red heart and he replied with a short message.

“I’d do you.”

I felt my cock stiffen even more.

I decided to carry on dressing up. I put on a tight black T-shirt, obviously made for a woman with a bust. It looked good with my “full chest” and the bra stuck out slightly. I then pulled on a mini skirt that was a similar black colour, but you could see there was a difference. I looked at myself once more, I was so sexy.

I crept out of my room to the bathroom Down the hall. I locked the door behind me and walked over to the sink. In the cupboard under the sink, I found what I was looking for, three large makeup bags. I took the biggest one, moms, and placed it by the sink. I opened the bag and tipped all the contents out. Pens, lipsticks, powders all fell out, I was in heaven.

I worked slowly, contouring my face and slowly placing shadows and highlights. I put eyeshadow and mascara, making my eyes seem to pop out with the eyelash pencil. I had seen mom and my sisters do it many times and had done it to myself a few times few times too. I knew how it was meant to look and I did quite a good job of it also.

I looked sexy as fuck and I knew my friends would appreciate it. I untied my long hair that was usually in a topknot and brushed it, then I tied it in a side ponytail, making me look extra girly. I looked just like a girl, which made me excited and horny. I quickly put all mom's makeup away and put her bag back under the sink. I took a few pictures, taking sexy poses.

I decided that I couldn’t hold back any longer, I sneaked back to my room and locked it behind me. I lay back on my bed and hiked up the skirt, I struggled to free my cock from its pink, cotton prison, and soon had it in my hand.

I slowly started to jerk myself off, for some reason imagining one of my two best friends doing it to me. My mind switch between some hardcore gay things with my friend and some really naughty things with my female friend. It didn’t take long for me to cum, spurting my load all over the pink panties.

“Shit, my sis will kill me.”

I looked over at my phone which had buzzed while I was jerking. My friend had returned a picture message. It was him naked with his hard cock in view.

I quickly peeled off all the clothes I was wearing and took them back to my sister’s room, I stuffed the soiled panties at the bottom of her laundry hamper and put the rest of the clothes neatly where I had found them.

I went back to the bathroom, not bothering to lock the door. I grabbed the bottle of facial scrub and makeup remover that was always to the side of the sink and got to work cleaning myself up. I then took a long hot shower, switching it to cold half way.

Just as I stepped out the shower my sister popped her head through the door.

“Matt, have you seen my lucky pink panties?”