In school I was usualy trying to get out of gym class 

I remember always making excuses and reasons why I needed to be in the Library rather than gym

Halfway into the year we had a substitute gym teacher and he was not going to let me out

He told me if I didnt want to participate in the sports part I could do clean up

I was sent to the supply room where all the nets and balls and other sports equipment was kept

Everyone else was playing basketball out in the gym and I was happy to be in a quiet room alone.

I began to put all the balls in their correct bags and reorganize the bats and gloves and other gear.

I noticed that there were also team jerseys and extra outfits for some of the teams

My school had a cheerleader squad and sure enough the storeroom had their outfits

I was scared of getting caught but I figured everyone was practicing loudly in the gym

I found one that seemed to be my size, the skirt and top and even the long socks they wore fit perfectly

I looked so cute and started to prance and twirl around  

I started to get realy turend on and figured it would be ok to play just a little

I got a bit lost in my fantasy and wasnt paying attention, when I looked up there in the little wire window on the door was frank

He had been my friend for years and we had both talked about sex and traded fantasies and desires

He was kinda surprised, I guess the class was going out to the outdoor court since it was so hot and he came to tell me.

I didnt know what to do since he had fully caught me dresseed up but he played it cool and made it like it was nothing

A week later he came to my house and we were in my room talking and he asked me about the cheerleader dress up

I told him that I had been into playing dress up and I liked to wear girly clothes

He asked if I had any there and I certainly did. my mom used my closet for her extra clothes.

I already had a stash of panties and a bra so I told him yes and he asked if I wanted to dress up for him

I was very shy but also wanted to please my freind and had already been caught dressed up

I told him to go to the bathroom and I would get ready, when he returned  I was in my moms dress playing with my hair

He came in and sat down on my bed we were both virgins and didnt know much about sex yet

He started to grope me and then tried to kiss me, and I was nervous and turned away and laid face down on bed

My erection had begun to grow and I often masturbated face down rubbing my groin on the bed

My silky panties and the dress felt so smooth and I was getting very aroused when Frank climbed ontop of me

We were still dressed but he dry humped my ass and I kept arching back and pushing my booty towards him

I heard him moan and we both came and I felt a rush of excitemt having satisfied my first boy

This became a somewhat regular occorance until he went away to France on a class trip

When he returned he was different, more mature. He told me he had lost his virginity to a prostitue

He also had gone to the red light district and gotten lingerie and toys for me

I was not sure that I wanted this, I had actualy met a girl I liked while he was gone

The pressure of expectation got the better of me and I dressed up for Frank in the gifts he brought me

I also started playing with the vibrator he got me and intuitivly it found its way to my hole.

He was so turned on watching me that he started to jerk off and came all over me.

I was ashamed and ran to the bathroom and got in the shower

My hardon was so intense and it wouldnt go down so I masturbated too and came

I got back into my boy clothes and told him that would be that last time we did this and left his house

it effected our freindship and we became a bit estranged, he got in with the mechanic crew and I hung out with linda my girl

She was asking me to take her virginity but I was scared and kept saying lets wait for prom or a special occasion.

She wasnt willing to wait and by the next week she was franks girlfriend.

He told her all about my dress up and didnt say anything about his participation in it

She lost her virginity to him on his bed right where he had cum on me just months before.