This story involves teenage crossdressing. Only read if you of age and like this type of material. It is purely fictional. I hope you enjoy.
It was a Saturday morning and as usual mum was at work and dad had gone shopping and then gone to visit his mum and drop off her shopping, he didn't get back until after 12:00 this gave me a good 4 hours to dress before he got home. In this time I would go and find some of my mothers clothes, my favourite been, white bras & panties, black skirt and a white blouse.
As I was only 12, I hadn't started growing hair so my legs look pretty good.
The only problem with mum clothes was they were to big so I decided it would be a good Idea to go shopping for my own.
That morning I got up bright and early, and was showering as mum & dad left.
I got out and dried off. Wrapping a towel around my self in a girlie fashion above my chest. Going into mums room a found some knickers and a tampon. I always wore a tampon when dressed as this made me feel like a real girl, as real girls had periods, one of the best thing was buying them, you get some funny looks doing so when you're a boy! But I'd never thought twice about doing so. This was the only girls things that I was going to wear whilst leaving the house as I didn't want the neighbours to see me leaving the house.
I put in the tampon and pulled on the knickers and before putting on my outer clothes painted my nails pale blue to match my jacket. I'd bought the varnish a few weeks earlier with this in mind.
At this time I was a mod, number 2 shaved head, sink tight stretch jeans, polo shirt and a silk pilot jacket and doc martin shoes, was my usual attire. So I put these on not to bring attention to my self whilst in the neighbour hood. As a mod I knew a couple of modetts who dressed just the same.
I found some pink lip stick and blue eye shadow and a compact with a mirror, and dropped them into a carrier bag, along with some gold loop earrings, a sliver chain and two sliver rings from mums jewellery box. I found that the earrings looked good and stopped on without having my ears pieced, but they do leave red sore dots.
I left the house and caught the bus into town, making a conscious effort for the driver not to see my nails. Once in town I made my way to quiet ally and put on the earrings, rings & chain and make-up, which I'd been practising for many weeks before.
Making my way up the busy high street I left very self-conscious, that somebody would either read me or I'd been recognised. Taking small delicate steps I went into Deberhams. Heading straight for the Ladies to check my make-up and have a pee. After some reassurance that all looked well I went to the girls fashion department and started to brows the clothes, choosing a red knee length dress with a white collar that buttoned up the back, I went to the changing room to try it on. I had never felt so nervous in my life as I took off my cloths and slip on the dress, in a real shop. It looked fabulous with one exception I had no breasts to fill the front out. After admiring myself in the mirror for what seen an age, I got changed back into my clothes hung the dress back on it's hanger and headed for the way out of the changing rooms. The woman on the door asked if I would like it and I said no. Leaving the dress with the lady, I went back onto the shop floor were I started to look at the underwear.
The next thing I knew there was a shop assistant asking if she could help me.
Once again I said 'no', not to draw attention to myself. She stepped back and dealt with another girl and her mother who also were buying underwear.
I carried on looking, I had every intention of buying some panties and a bra of my very own. Checking sizes and matching bras with panties the shop assistant returned, she looked at me in a very knowing way. I was sure at she had read me and that my game was up. I was trembling at the knees, when she asked me if I was sure that I'd selected the right size. 'No' I replied
'well we'd better measure you, to save you coming back'
Taking me into the one of changing rooms cubicles she asked me to remove my top, shaking like a leaf I turned my back, and took for my Jacket and polo shirt. Carrying a bit of what mum & dad called 'puppy fat'. This gave my chest the appearance of budding boobs. The Ladies asked me to turning around, not looking her in the eye, she placed a tape measure around my chest and took a measurement, adjusting up the tape slightly she then took another measurement. Finally she took her tape and measured my hips.
She announced I was a 32 A, with 30ins hips.
The assistant asked me which bra I'd been looking at, I said ' the plain one on the bottom row.'
The assistant left the changing room and after a few seconds she had returned with 3 bras, all in my size. First I tried the on the one which I'd been looking at. I placed shaking hands through the straps that the assistant was hold out, she pulled them up over my shoulders going around the back she then fastened the clasp and adjusted the shoulder straps.
I filled out the cups quiet nicely and I had the starting of a cleavage. She asked if it was comfortable I said 'that it was a little tight around the middle'. She once again adjusted the back. Which felt much better.
She asked if I liked to try on one of the other bras that she'd brought. One was like the first, white cotton, with small blue and yellow daisies. The other was a creamy stain with a lightly laced trim.
Been so nervous I declined the offer, asking if I could just take the one I'd still got on.
She asked if I was going to wear it home, I replied no and took it off. The assistant left the changing room with the other bras and left me to get changed.
Once dressed I went back to the display and picked up a packet of 3 matching panties, which I now knew was my size.
I made my way over to the check out where the lady that had helped me was now serving.
She packed them and I paid for them and left to catch the bus home.
On the bus I went to the back seat that was thankfully quiet, took off all the jewellery. But I had to leave on the make-up. When off the bus, I ran as fast as I could home, so if anybody saw me they couldn't tell I was wearing make-up.
Once home I went straight up stairs and tried on my new purchases. Walking around the house in my new bras and panties, I replaced all the items I'd borrowed and took off the nail varnish and make-up, and removed the tampon.
Finally I took my-self in 'hand' to relieve the pressure. I stashed the bras and panties in a hiding place under the floor in my bedroom, along with the nail varnish and a box of Tampax.
I got dressed back into the same clothes I'd been out in, this time without the female trappings.
Now relaxing with a cup of coffee dad returned, feeling very guilty I was sure he knew what I'd been up to that morning, but of cause he didn't.
To this day I'm not sure if the shop assistance knew I was a boy and were just humouring me, or if they really thought I was a real girl, I'll never know.
To the day I die I will always think of this day.