A Virgin Crossdresser

I was newly turned 18 never even kissed a girl let alone had sex. I had been crossdressing for about a year and had stumbled upon a site called tvchix which where I spent my nights in chat looking and getting an insight into what this world could offer.

Bit of background I had named my alter ego Jessica and I was quite convincing looking cd 6ft skinny little bubble butt and a craving for cock or what I thought was curiosity. It was winter 2010 and I was still in high school only had my mum’s lingerie which she never wore and a few items like a wig etc.

I had plenty offers but something caught my eye a week after my 18th birthday a personal trainer with a place of his own wanted to meet so I took the plunge and decided to see if I could actually be the slut I was in the chat rooms.

So I packed a bag with a wig and makeup put on my red stockings bra and thong hiding it under my boy clothes which all ready had me hard as a rock and horny and told my parents I was off to my friends house. I jumped on the bus and one of my mates jumped on the bus with me petrified that he would see the bulge of the bra or the stockings under my clothes. Told him some excuse that i was off to see a friend and it seemed to fly and I hopped off the bus.

I had arranged for my meet to pick me up at a petrol station outside a super market and with my heart beating fast as it had ever before waited for the pickup I felt like such a hooker standing on a corner with lingerie on waiting for my first cat call.

When the car arrived he smiled at me pulled up and let me in a few pleasant greetings and I was at ease eager to get on with what dirty thing we had come to do. He lead me into this lovely new build flat and said “ would you like a drink” I said “no thank you I would like to get ready” with that he showed me to the bathroom and to head through when I was ready.

So I applied my makeup blue eyeliner my face with mascara. and some red slutty lipstick to complete the look now foundation required and god to I wish I could still pull that off. Looking at my self in the mirror Jessica was looking back at me a brown medium length wig sat on my head complete hairless below my eyebrows with a red lacy bra and thong red stockings and black knee high boots i was ready.