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    My Life as a Tranny

     

    Leaving all the definitions behind I always considered myself to be a transvestite rather than a cross dresser. Only because tranny sounds sexier. I have had the urge to dress feminine since High School and at first I loved to come home early from school and dress up in my mother's panties and anything tight that she had. Wearing these clothes gave me the feelings of wanting to be tied up, helpless and abused. On occasions I tried self bondage.

    The urges ranged from extreme feelings to total repulsion of myself. In later years this was demonstrated by the number of times I would throw out my girly things after a dressing splurge.

    Unfortunately I could never transform myself to even look partly like a sexy women. The downright slutty look only held me for a few minutes. Just imagine how I felt at the last day of high school. In Australia the final high school year has a muck up day and 2 of the guys from my year came as sexy girls. Believe me they were beautiful and made up professionaly. They were dressed in  new and sexy clothes that obviously were not hand me downs. To make it more painful the more attractive of the 2 lived in my street about 5 houses up. I did not even have the courage to go over and compliment them on how good they looked. They had a great time just sitting there cross legged watching what the boys were doing and looking sexy. For months this drove me insane and so randy that at times I could not stand it.

    Although my on and off cross dressing continued I could never feel really fullfilled. Probably that was one of the main reasons that I married fairly young. Living with a women only increased my desire to cross dress. My wife was so much smaller than me that it was useless trying her clothes on. Being dirt poor some how I had to hide my purchases and the gear for the short times that I was able to dress.

    During this period the urges were extreme and on accasions I became more braver and ventured outside in drag. This mainly involved walking around the streets or driving. Lucky I did not bump into anyone. The closest I came to being discovered was one night after an office party. Drunk, I made my way back to my car, changed into my sluttiest outfit, and drove home. I felt so great. Arriving home at our block of units the security man saw me driving into the car park. Always hoping that he thought I might be a prostitute he started to walk towards my parking spot, but luckily I got out before he arrived.

    Ads in sex papers advertising myself as a live in tranny resulted in a response from a guy. This actually went to the stage of arranging a meeting in public, which obviously I chickened out off as there was no way that I could make myself half presentable.

    Met up with a darling old man through another sex paper. He was just too old for the sex crazed world that I desired although he gave me my first insite into the results that could be achieved through hormone treatments with his breasts and limp cock. He tried to convince me to move in with him and he could help me get into the Sydney tranny scene as he was friends with many people.

    His only real need of me was to allow him to suck me off. He had no desire for me to relieve him as his cock was pretty well dead. This did not fit in at all with my desires, which was normally to bring myself to masturbation by being the sexy and helpless slut. At my suggestion he tried tying me up and then having his fun but this did not work for me.

    Shortly that relationship finished and my marriage also broke down.

    This lead to a period of me paying for sex with transexual prostitutes. What was obvious from these meetings was my total virgin persona in sucking a cock or fucking someone up the arse. I even paid more at these brothels for them to make me up as the helpless girl, tie and tease me. This helplessness really turned on the desires from the past. I started looking around again for men  to discipline me. The first few attempts were not good with one guy who I meet at his place went totally cold from the start claiming that he had fucked his wife the night before and no longer felt like cross dressing anymore. I was so mad as I was really randy and had to relieve myself in his bathroom, before leaving. In fact when I thought back about that one I had a major urge that I should have restrained the prick and tied his cock to the bedroom door handle for his wife to find him dolled up.

    Another guy who was straight failed to tell me that his vice was spanking- nothing more. He shaved my arse and beat it black and blue with his hand and different types of paddles and canes. That was not a turn on for me and I did not return.

    Occasional hook ups with pros continued but this was not achieving any real sexual pleasure.

    Somewhere I came up with a name and phone number of a local guy. At this time I had totally lost the urge to cross dress.

    His name was John and I visited him at his place. The first thing to strike me was that he was the first man I had met through these ads who appeared down to earth and nice. He even introduced me to his wife. I tried to break the ice with her, and while she was not rude it was obviously an uncomfortable situation that she had experienced on a number of previous occasions.

    John and I went to his bedroom. As with all the rooms in the house his room was decorated tastefully and not cheaply. The double bed had a plastic covering. He explained that a number of years ago he had told his wife that he was gay. They were both in their mid fifties so it was agreed that they would continue to live in the same house but have separate bedrooms.

    We undressed and laid down on the bed together. We embraced and just laid there feeling each other. As he gently stroked my cock he asked me if I had much experience. Being aware of my immaturity in this area he told me to lie back and relax. I became stiff from his gentle touch and then he took my prick in his mouth. This was the very first time that anyone really sucked me off. I was in heaven and had never felt this good before. I came and I was his. I tried to make advances to him to try and reciprocate but he told me just to lie back and enjoy the moment.

    Then out of the blue he asked if I would like to the tied up. He told me that it would be nothing heavy but he liked to restrain his partners in different positions. It came as such a surprise, that would you believe I said no. He said that was alright and if I would like to make this a regular meeting.

    I told him that I would love to.

    And that is where I will leave this blog. Next up I will talk about my return visits with John, meeting another of John's boyfrieds and meeting Debbie, who was the wife of Robbie (John's boyfriend), and she is the one who helped me to full time feminization.

     
      Posted on : Aug 12, 2011
     

     
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