1. Blackmailed Crossdresser , part II


    Date: 4/14/2018, Categories: Trans, Author: tricked-sissy, Source: xHamster

    A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself. I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier, stockings and heels, with a wig on but visible to see.And he was behind me, obviously fucking me. This wasn’t ambiguous. What had he done? There must have been a secret camera on that dresser opposite the bed. He then messaged me again: “there is a video that goes with these images. we have a problem it seems. but I am sure we can work kit out” This would be the beginning of his exploitation of me. I agreed to meet him again. I was already prepared in my head to let him fuck me once more. I had managed to get through the last time, in reflection, the cock-sucking wasn’t so bad. It was the anal that hurt. If that was the price of buying him off, then I could do it one more time. But I would pick the place, I told myself. But in the end he didn’t want to meet in any hotel, either of my choosing or his. We met in a café. He told me he would keep the video a secret, protect the truth of my transvestism, and all he wanted in return was to be involved in my crossdressing. To see more ...
    pictures as I made them, to be allowed to by gifts of clothes for me and make requests. And to occasionally be allowed to show his appreciation physically. Though I was sceptical about letting him further into my life and I already knew what he meant by his last request, I agreed to go along with it. I felt I didn’t have any other options, and also thought if I played along for a while he’d either get bored, or I would get a chance to steal back the material he had on me. And I admit there was a part of me that was a little excited to have an audience for my crossdressing after years of experimenting in secret on my own. About a week later a box came from an online shop. It was a a pair of very small denim short shorts, a little bit slutty and tacky looking with some thin gold chains hanging at the front, and a long red and blonde wig. A message followed from him requesting pictures, and demanding I make it “sexy”. it was strange to have some else picking out clothes for me to wear, but I found it kind of exciting. I also found the shorts and wig pretty sexy. I couldn’t wait to try them on. That evening I painted my nails and dressed up in nylons and the short shorts. I put on the wig and took a few pictures on my phone. I sent them over to Stefan. Half an hour later he rang me up. “Come over to my place and bring exactly those clothes. I want to see how they look in person.” I deliberated for a while whether to follow up on his request. I knew what might be in store, but I was not ...
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