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Not Crossing The Line
Date: 8/6/2015, Categories: Crossdressing, Author: Spooge, Rating: 5, Source: LushStories
with someone. I told her I chose her because she was a little outside my regular group of friends but someone I trusted much more than most. It put her in a receptive mood. When I eventually spit out the words to tell her I occasionally crossdressed she said, “I’d love to see that.” From that point on there was only one thing to do: Don’t fuck it up. As the discussion continued Jennie became genuinely curious and asked questions. At one point she asked, “Are you gay?” I told her that I was not and that I was actually aroused about letting her see me like that. I wormed my way around to telling her I wanted to get a photo of myself with real women. She knew what I was getting at and reminded me that she does not enjoy having her photo taken. Selecting a couple photos of myself, I sent them to Jennie. She understood why I had blurred my face because my concern had been clear throughout the conversation. Keeping this activity a secret was a priority. Jennie asked for a little time to let it sink in. That was fine with me because my anxiety level was running high. A few days later I got a text: What kind of photos are you hoping to get? My heart leapt. Jennie might actually agree to it. First, I explained my slow methods. Always on my own, I have to set my camera up with a timer for each shot. Getting the position right should be easier with her in view as I prepare them, but I said I would like to shoot many because I never know if they will turn out good. Jennie asked more ... directly what I wanted her to do for them. "Just be your usual gorgeous self," I started. Then I told her I would like her to also be in heels and showing her great legs. My impression was that she was reasonably comfortable with the idea so I mentioned that with my own clothes I preferred the skimpiest things I could find. We arranged to meet on a weekend when we both had time to ourselves. I would bring my bag of ladies clothes but arrive dressed normally. That was in both our interests. It kept me from worrying about being seen and kept her neighbours from thinking a weirdo had come to visit. She moved since the last time I had been to her place so everything was new to me. As expected, my nerves were on edge as I approached her house. Jennie smiled immediately, gave me a big hug and invited me inside. Walking in front of me, I was grateful to see that sexy hourglass figure before me. Jennie was wearing a tight black skirt and black heels like she wore so often to work before. When she turned around my gaze was still below her waist. "Are you sure this isn't just a ploy to photograph me?" How could I deny that? Unjustly. "I forgot just how good you look. Yes, I would love to just have photos of you, but I know you would not want to do that. I am grateful that you are considering any of it." We checked out her house to plan where to shoot photos. I asked that we avoid the front room because she has a large window viewable by people walking by. This left the kitchen and dining ...