1. My first time as a Crossdresser


    Date: 10/1/2015, Categories: Anal, First Time, Shemales, Author: mileslong34, Rating: 100, Source: xHamster

    Its 18 months ago. I had now become comfortable wearing womens clothes. I had been experimenting for around 3 months. I gradually started to get more confident in both my clothes ......and without. I started to dress more like a slut. Short skits. Suspenders. Corsets. I had also become more comfortable with my body as well. My hole was tight as could be. Like everyone, i started with fingers, one, two .....before moving on to small toys. After a few months, i had graduated to a 9 inch dildo.....although i still struggled. I felt so hot. So right. I had been chatting with other CDs and men on both here and a swingers site. It turned me on SO much. I felt naughty. One night, feeling extra confident....and with a little Dutch courage, i decided to take up one of many invitations to meet a man locally. We had been chatting for a while and he had told me how much my pictures turned him on. I felt hot. I decided to meet in a public place. He suggested a small country pub close to him. At first i was sceptical. What would people think?? He assured me that it would be fine, its usually quiet on the week nights. I decided to go quite casual......no suspenders and corsets in this small pub ;) I choose simple black leggings tight top covered by a leather jacket. On my way not once did i feel wrong or stupid. I felt right. I felt sexy. My heart was racing. As i had had a few drinks to relax, he offered to pay for a taxi for me. When i got in the taxi, i could see the the taxi drivers ...
    eyes on me. A middle aged man, looking at me, what was he thinking? Was my make up wrong? I checked. Nope it was fine. As we pulled up to the pub he turned to me and said ' Here we are love. Are you meeting your fella?' 'Something like that' i responded. 'Lucky guy' he remarked with a cheeky smile. Woahhh! What just happened? I had gone from feeling judged to feeling hot and sexy. As i walked from the taxi i looked back to see if he was still looking. He had his eyes firmly wrapped on my ass. Cheeky taxi driver :) By now i felt super confident and strutted into the pub. He was right, it was quiet. Around 7 or 8 men spread out around the bar. As i entered i felt all eyes on me. This time i didnt feel judged. I was the only woman in this bar. My date quickly removed me from the centre of the bar to a quiet little table round the side. 'They'll all want you if you stand there' he joked. We quickly got on like a house on fire just like on our online chats. He kept complimenting me. My big kissable lips. My beautiful blue eyes. My long legs. My hot ass. I felt amazing at this point. i was so turned on. As he was at the bar ordering more drinks, i could see him and the barman chatting about me. What were they saying?? When he returned he told me the barman asked if i was a model, because of my height and legs. Everything was feeling right at this point. He started stroked my leg and kissed me gently. As i leaned over he grabbed my ass. He moved me closer to him and further out of view ...
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