1. My First Time Dressed as a Girl (PT 3) (Consequenc


    Date: 10/20/2017, Categories: Fetish, First Time, Shemales, Author: sbobbi66, Rating: 100, Source: xHamster

    Well. I had written a follow up to ‘My First Time as a Crossdresser, PT 2” but Microsoft decided that the moment I attempted to upload was the perfect moment to update and erased the whole story, which means I had to rewrite the whole thing. So... After I dressed in the schoolgirl outfit that Gunther had put out for me, I pulled my hair into a high ponytail and put on makeup emphasizing my eyes and lips without going overboard. I walked out into the living room to discover that Tracey had left and Gunther was dressed in a pair of slacks and a very expensive looking Cashmere cardigan. He smiled broadly and said he knew I’d make the right choice. Then he pulled a long tweed ladies coat out of the hall closet and handed it to me. It was a little big but fit fairly well; I assumed it was from one of his previous gurls. “Put it on we’re going out for dinner and then maybe some dancing.” He grabbed a coat for himself and we headed out after I snatched up the purse with my borrowed ID in it. We went out to the parking lot and Gunther walked over to one of the few garages at the complex and punched a code into the keypad which opened the garage door to reveal a bright yellow Porsche 911SC Convertible. He laughed as I gaped at his ride. “What can I say? I prefer German engineering I brought it over from Stuttgart last year. Much cheaper in Germany!” We got in and Gunther drove us to The Grotto, one of the nicest restaurants in town. We were seated at a secluded booth where Gunther ...
    ordered dinner for both of us. While we ate he asked me questions about my life quickly ascertaining that I had a lot of freedom to do as I pleased with little in the way of parental supervision because I didn’t cause much trouble at home. My Father traveled a lot and after the hell my older s****r put my Mother through she was pretty content to give me free reign as long as I didn’t get into any trouble and kept my grades up. I quite often spent the night at a friend’s place so I knew I could get away with sneaking over to Gunther and Tracey’s pretty much whenever I wanted. He discussed the need for absolute secrecy with me because I was still only s*******n which could get him tossed in jail if my parents ever found out. He didn’t’ think my conservative father would take kindly to his teenage son being used as a sissy slut by an older man. Gunther explained that he traveled a lot so I would still have a lot of free time but that I was his little sissy when he was in town. I was to maintain my life as normal as possible so as not to arouse suspicion, even continue dating Mikki (which I was relieved at because even though I reveled in my newfound role as Gunther’s sissy, the thought of not hooking up with Mikki was torture even though I knew I’d quit seeing her if he ordered me too.) Furthermore I was to keep myself hairless at all times from the eyebrows down. He also explained that he had an account at a local salon and I was to go there every week on Friday after school to ...
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