1. The First Date

    Date: 2/12/2020, Categories: Fetish Trans Author: alexismack, Source: xHamster

    IntroTo start, just a little bit about myself. I am a 34-year-old crossdresser that has been dressing for most of her life and has reached a certain breaking point of needing to transition. My stories are a way for me to deal with my dysphoria and provide me with guidance as I continue this journey. I’ve met folks that have inspired me to write these stories, so, for now, they are a work of fiction, but maybe one day a reality.Chapter 1We had been chatting back for forth for weeks, Sir, as I would refer to him, had been becoming for and more infatuated with me, I was beginning to really enjoy the attention. It started with leaving me Good Morning messages, and cute emojis through the day, and connecting with me on other social platforms. We really started out on Fetlife, I would like some of his pics and he would like some of mine, and leave amazing comments, driving me crazy. Being friends on Fetlife he was able to see all my pics, so I knew he knew what I looked like and he didn’t turn around and run, hehe. As we chatted more and more, our conversations grew more sexual and heated. We lived fairly far apart but who knows if we would ever meet.A few messages later, Sir informed me that he would be at a conference not far from me, this sent shivers down my spine. As I read further he suggested that we potentially try and meet up and that I join him for a night or two. The immediate scenarios ran through my mind, an I available that weekend, how would this work, what would we do, what would I wear. ;) nasty little thoughts ran through my mind. I told him that I would think about it and let him know when it got a little closer, maybe I could make one-night work.Being a crossdresser, I have purged more times then I would like to admit, so I’m constantly rebuilding my wardrobe and coming up with my style. I told Sir that if I would attempt this I might need some new outfits, he told me that we might be able to arrange something, and I should get a wish list together…Chapter 2My hands trembled as I entered the code for the Amazon locker, as I retrieved the numerous boxes, I had a good idea of what I would be receiving. I had put together a modest wishlist on Amazon, mostly 2 outfits, one casual and one dressy for dinner. I rushed home as quick as I could to open the boxes and take inventory of everything.To start, the casual outfit, which consisted of a pair of skinny distressed jeans, with some holes. A cute flower top and jacket completed the look. For the undergarments, a cute pair of pink hipster panties and a pink push-up bra to complete it. For footwear, a cute pair of wedge heels, in black with some straps, to give me some height and to show off my painted toes. Hopefully, to not appear too over the top, I wanted something I could easily pass in and show up wearing.For the night, a sexy pinup style dress in dark red, with a flared skirt that raises just a little bit when you twirl. To cover the arms and shoulders just a little black crop ...