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I have always enjoyed crossdressing. For as long as I can remember I've had the urge to wear womens clothing.
Honestly don't know where the temptation comes from but it's always felt so taboo that I've kept it hidden from nearly every single person in my life. How soft the fabrics feel, how the clothing hugs the body in new and intresting ways and how much more pretty they are compared to my boring boy clothes.
The first item of clothing I tried on, like so many other crossdressers, was my sisters knickers. I loved how they felt on my body I just know I had to try on more and different clothes. So when the house was empty I'd try on all I can. Skirts, dresses, girly tops, as much as I could as often as I could. It was wonderful. My favorite items I 'borrowed' was a short red skirt and matching crop top. My sister was taking dance clasess at the time and they had given her this red set. It was lthe same style as the american cheer leaders wear and it felt so feminine, so exciting.
Fast forward a few years and I grew big enough to try on some of my mother's clothes and shoes. It was the first time I was able to try on a real bra. It was a new sensation I fell in love with. Thos also introduced me to how much more intresting knickers can be. So many soft lacey pairs, satin ones and a thong or two. I would spend hours trying them on and looking at myself in the mirror with pair of 4 inch heels I'd found. I was in heaven!
Around about the age of 14 my freinds and I where quetly dicussing porn in the way that teenage boys do and one of them mentioned a site I'd ever heard of before, Imagefap.com. He spoke of all the different types of smut you could find on here and it peaked my intrest. I went home and soon as it was quiet enough I looked it up and was amazed at how right he was. After a few visits that I can only describe as very hetrosexual I stumbbled across what would become my first ever trans porn. The woman was so beautiful I slowly followed the gallery along as she stripped her clothing off and when her cock popped out I was so aroused. I knew I had to find more. From that it was a short jump from trans to finding crossdressers. Seeing all these others who just like me enjoyed the feel of women's clothing on their skin was a break though. Made me feel less alone in my urges.
I learnt so much about the others with this kink. Feeling deep inside that I too was a submissive like many of these gurls. Soon all my fantasies where of dressing and I was masturbating to the idea of getting fucked.
When I finaly flew the nest and moved into a place with some freinds I started buying my own clothing online. Just a few bits of underware and a skirt but it was enough for me at the time. One of these freinds left her 6 inch heel shoes next to the door. they where all black with studs up the heel and back of them. I fell in love. When the house was empty I'd walk around in lacy underwear and these heels. I've been searching for a pair just like them since.
Slowly through the years I've added and purged clothing from my collection but I'm finaly in a place where I can be dressed whenever I like. The freedom to relax in a flowing skirt or do a little cleaning in a dress has been wonderful.
Alot more came out than I thought would. Definatly more than just early experiences, more of the highlights of my crossdressing life thrown in. If you have any questions about anything I've written feel free to ask, I'm always happy to get message.
And a thank you to Masterdavis. Master is the one who gave me the task of writing this out. I do this happily because I am his good little sissy.
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