CD As A Teen

When I was 18 I house sit twice for some friends of the family, they travelled twice a year for several weeks at a time and wanted someone to look after their home so as they knew me to be very responsible and hard working they asked and I said yes.

So I moved into theirs, it was about 30min drive from my home in a small village; it was closer to my work so easy commute and I had access to their gym and entertainment system so was very happy.

When younger in my early teens I cross dressed by stealing, borrowing clothes from my friends moms etc... by helping myself to them when I was over at theirs, not proud but hey I was a rather curious teen.

I moved on as I got a bit older mostly as I outgrew the clothes I had and found less time to try and dress.

So one night into the first week house sitting I found myself very tempted and raided the wardrobes.

It was quite different this time as I was very conscious on the effect it had on my body, I was shivering with pleasure as I slid some tights on, to the feel of the skirt and top, I didn't use make up as that I felt would have been too noticeable.

I felt great walking around, the feel of the silk top caressing my flesh to how great my legs looked.

That night I cleaned up, making sure to put everything back as it was and went to bed confident I had gotten it out of my system, this was not the case.

Two days later I visited a costume party shop and under the ruse that I was picking up items for my girlfriend I bought a brunette wig of medium length and some make up kits.

I phoned my folks letting them know I was doing okay and things were fine before rushing to shower, primp and shave what little hair on my body I had.

Thankfully the clothes I was borrowing didn't look to bad on me, the sizes rather close to my own skinny body though I was not unhealthy I just never carried lots of weight except on my thighs and bum.

I used some video sites to touch up on how to do make up and after some practise I looked very good, with the wig I was very passable.

I choose a dress this time, came to my knees and with a bit of padding in the bra I looked good, the dress was a black jumper style that fit me snugly and had a high collar that hid my tiny Adams apple.

I wore black tights and some lacy underwear and even though they felt tight I slip on a pair of heeled ankle boots.

I walked around the home, relaxed watching tv and practised my voice and mannerisms, the voice coming back to me after a few tries.

It was dark now, and feeling emboldened I took a chance on going for a drive, dressed as I was and it was amazing, no one battered an eye if they noticed me behind the wheel, I even stopped off at supermarket car park and got out, walked up to the Atm withdrew some cash and got back in without any problems.

Into the second week and I was hooked again on dressing, every day I spent time in a different outfit after work, making sure to return everything to how it was, I was paranoid about being careful.

It was the Friday night and I felt adventurous and dressed again in the jumper dress and waiting till dark I went for another drive, this time though I drove to a gay pub I had visited before as my normal male self.

I sat in the car for a little while, just there in the car park, and with a final bit of courage I grabbed my borrowed handbag and went in.

Nothing, no stop the presses, no one staring at me, no one even really glanced my way as I strolled up to the bar and ordered a lemonade (I was driving after all).

That night I had some fun, talked to a few guys, was upfront that I was a cross dresser, most were okay but not interested till I found a slightly older guy in his early twenties who seemed quite keen to talk.

He was very nerdy and not confident but we had a good laugh, we danced a little (rather awkwardly if I am honest) and ended the night with a heated kiss, but as I felt his hard cock pressing into me I had to have him.

I drove us back to where I was staying, and leading him I got fucked as a girl for the first time; he was a bit nervous, he was a lot bigger than I thought and he thought he would hurt me, but I was determined to take all of him into me so with a few painful grunts and me pressing down he filled me good.

I rode him hard that night and the next morning before I drove him back into town, this time dressed as my male side, I found we got on rather well despite how I dressed or looked.

We became an item for a while, and I was happy.