1. Road to Ruin


    Date: 9/29/2015, Categories: BDSM, Fetish, Author: klammer, Rating: 100, Source: xHamster

    sex really turned me on and I think that I was hooked on the adrenaline rush of it all. Talk about conflicted. But no death wish here, so I vowed to be more careful in the future. At this point my life I was pretty much torn between my desires, almost compulsion, to cross dress and have sex with men and clinging to whatever semblance of what was left of my former normal life. I am a bit of a hypochondriac, and was worried about disease. I had already learned my lesson regarding that the hard way. In any event I was hanging out at my apartment with my roommates and one of them came in with the campus newspaper and was laughing about an ad in the personal section. The ad said &#034free lodging and a Mustang convertible to use during the week in exchange for pleasurable weekends.&#034 It went on to say that the person that placed the ad lived in New York City but traveled to my town frequently for business. While my roommates were making fun of this, it sounded like a pretty interesting idea for me. In any event I called the number that was in the ad and spoke to a pleasant sounding man. He said his name was Malcolm and he was a doctor, and that he managed emergency rooms and hospitals and as part of his business, he came to my town pretty much every weekend. We arranged a time for him to &#034interview&#034 me and I thought about how I would prepare. I did not ask him over the phone if he was looking for a masculine boyfriend but figured there would be plenty of those but I ...
    might stand out if I should come fully dressed. In any event, I want the whole 9 yards. I put on panties, thigh highs, stiletto heels, very short miniskirt, and my biggest breast forms, very tight top and with the full make up including eyeshadow, false eyelashes and deep red lipstick. To top it off, I put on a beautiful blond wig. I really looked pretty hot. The big question of course was whether or not the good doctor wanted a submissive girl or a masculine boy. I snuck out of my apartment and drove over to the meeting place. I rang the doorbell and my heart was pounding. The man that opened the door looked to be in his early 40s, he was tall maybe 6'3&#034 and had very chiseled good looks. He was clearly surprised to see me dressed up as I was, but after the first look of surprise, he got a really big smile on his face and invited me in. He asked me if I wanted anything to drink and I told him that a glass of wine would be very nice. He brought me glass of Cabernet and we chatted for a few minutes about his business and his marital status, which was single and how his interviewing process was going. He said he talked to three other men but certainly nobody like me, and the way he said it he seemed very impressed with me. I finished my wine and he asked me if I wanted another glass and I said not at the moment. He took my glass back to the kitchen and came back out to his living room. He sat down in a chair and told me to sit wherever I like. I thought about it for a few ...
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