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Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can’t speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would give out my phone number. One person whom I deemed worthy enough to have my number was a man called Jack. We would talk regularly as well as texting, despite such things being in their infancy. Over the course of several months I spoke a lot to Jack. He was well spoken, in his early thirties, single, we lived in the same town and he worked in London. I was very nervous talking to someone about my secret but he always made me feel relaxed. Over time our conversations started turning to meeting in person. Jack never pressured me and always understood my concerns. He always reassured me, telling me there was no pressure. Eventually I grew brave enough to agree to meet but there was a slight problem. Ashamed as I am to admit it now but all of the clothes I wore belonged to other people. My sister, my step mum, and even a couple of my female friends had been victim to my borrowing. Of course this meant I didn’t have anything to wear for Jack. He reassured me it wouldn’t be a problem and asked me my sizes. I had to guess Beşevler escort Bayan based upon the things I’d worn before and Jack seemed satisfied as we arranged to meet in a few days time. When I arrived at Jack’s house I was taken aback. He had alluded to the fact he had money but I wasn’t expecting this. There sat an impressive BMW in front of a large detached 4 bedroom house. A perfectly kept garden surrounded by high trees and bushes. My heart was beating out of my chest as I reached out for the door bell. Before I could press it the door opened to reveal a handsome, tanned, tall man. Piercing blue eyes, cropped dark hair and a welcoming smile greeted me and led me into the hallway. The room was spacious and immaculately decorated and I couldn’t help but feel a little out of place in my scruffy jeans and tshirt. “I’m Jack.” The man introduced himself. “Would you like something to drink?” “Thank you, just water please.” I replied timidly. It felt strange to be talking to him face to face, especially in my own clothes. Jack showed me into the kitchen and we made small talk as he provided me with a glass of water. We sat talking awkwardly at a large kitchen table before he finally spoke more directly. “I don’t wish to be pushy or presumptive, but I bought you some things. Perhaps you’d like to try something on?” “I think I would like that.” I was incredibly Çankaya escort excited. Jack took me upstairs and into one of the bedrooms. “I had to best guess what you may like from what you’ve told me. I hope there is something you like. I also bought some things I liked too.” He said, pointing to a number of bags on the bed. “There is also some make up on the dresser if you’d like it. Please take your time.” I thanked him and he left me, closing the door as he went. I began to look through the bags and found a couple of dresses and some pieces of underwear as well as a pair of high heels. Amongst everything I found what I thought would be ideal. A virginal white lace bra with a matching white lace thong and a thick waisted white lace waspie suspender belt. I also found a short pleated skirt and a white blouse which I just had to use to create a school girl look which I finished with a pair of black, fence net stockings. I laid all the items out on the bed and, with a deep breath, I removed my jeans, tshirt, socks, and boxer shorts. I had been removing all my body hair as soon as it started appearing. Being naked in Jack’s house felt strangely erotic as I removed the fence net stockings from their packaging and sat on the bed. I always put my stockings on first and as I eased them up over my smooth legs I began to feel an excitement I’d never felt before. I Cebeci Escort wrapped the waspie around my waist and attached the clasps to the stockings. I eased the soft lace panties up over my stockinged legs and felt a little shock of pleasure as I tucked my cock away. I attached the bra behind my back and adjusted the straps so the soft cups held my shapeless chest. I Felt amazing as I stepped into the short skirt which barely covered the stocking tops. As I pulled the blouse on to my slender shoulders I went to the dresser and sat in front of it. I’d only lightly dabbled with make up and rather inexpertly applied far too much eye liner and lipstick. Luckily for me the ‘over the top’ make up look suited me and my school girl outfit. I slipped on the black high heels and looked into the mirror. I felt my nerves surge as I thought about the fact I was about to be seen dressed up for the first time. My long hair had been tied back but I pulled it free to let my dark straight locks cascade over my shoulders. I admired myself briefly in a full length mirror and a tinge of excitement surged through me. I timidly walked to the door and down the stairs, teetering on the high heels as I tried to walk. I found Jack reclining on a vast leather sofa in his lounge. As I walked in he jumped to his feet. “Wow!” He walked to me arms outstretched and embraced me firmly. “You look incredible!” I could feel myself blush as his eyes looked me up and down. “Give me a spin!” Struggling to balance on the high heels I slowly turned around. I felt his hand run gently down my back and onto my arse before returning to his side. I felt sexy and nervous, naughty and shy all at the same time. He motioned for me to sit down.
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