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NSFW...18+ Only Please.
Images are not necessarily my own, unless tagged as #me........
Crossdresser. 6ft 4" tall, short dark hair. Love everything feminine, but deep down know that i`m a bit of a sissy.
My name is Phil, but sometimes I go by the name Pippa. I`m often Pippa in my head and Phil to everyone else...but sometimes I get to be Pippa on the outside too.
It all started for me when I was about 4 years old. I don`t know why, but I had a fascination with my mothers underwear. A particular set of black silky underwear with red lace trim gave me strange feelings whenever I saw them. I also used to play with my sister and her friends back then. One particular day, I was getting dressed up in a lollipop lady`s outfit (don`t know why that one in particular - it was just there!)...my sister and her friend were putting finishing touches on me and I was just loving being the centre of attention. I was part of the gang, I belonged (more of which later). The woman from next door who was having tea with my mother commented on me playing dressup with the girls. "You know, he`d make a good little girl wouldn`t he?" was the throwaway comment. From then, I started to imagine what it would be like if I WAS a girl. So started early forays into dressing.
I mentioned earlier the feeling of being part of the gang, a belonging. This was a theme that would recurr time and again. I`ve always been quite a shy person, and found friendships a little difficult, especially at the start. Approaching a girl I liked in my early courting days was always difficult unless accompanied by copious amounts of alcohol. As I grew older, I often craved that sense of belonging with female companionship, however that was a door that became increasingly closed to me as puberty and later the male female divide kicked in. I imagined what it would be like to be a girl again...and how if I were, I could somehow belong to that `inner sanctum` although this was never to be.
So now, I find myself still dressing, still imagining myself as a girl, sometimes wishing I were, but fully recognising the fact that I am not, nor ever will be. I still seek to belong, but within the acceptance of who I am and what I can achieve. This community, and finding the companionship of others like me is now my comfort, my sense of belonging, my gang!