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" That'd be really nice, Mrs. Douglas."She parked at the curb in front of her home, and I noted it was a splitlevel colonial in a pretty nice area of town. The status of the homewas an indicator of a fairly well off middle class family, and I wasalready looking forward to seeing how she had decorated and furnishedthe inside. As I walked behind her along the walkway toward the home, Icouldn't help but admire how she looked from even that view. Notexactly gorgeous, but obviously the type of woman that I knew I wouldcompletely fall in love with, and I regretted immediately the agedifference between us...she would always be unobtainable for me.As we reached the door, I waited while she used her key to unlock thedoor, and I noted that I was probably only an inch taller than her. Ihad a fairly lean build, so I was already wondering if I would be ableto fit comfortably in her outfits. For the past few years, I haddabbled with trying on women's clothing, with most of my piecesliberated. I said, I am surprised too but I hope that the trip is worth the risk. After wrapping up, she asked if there was any alcohol. I had a bottle of vodka tucked in somewhere for emergency purposes. We both settled on the couch. She started talking about how much she has invested in the guy and how this was a huge blow for her.She was gulping down drinks and we both were a bit tipsy. The best part about my apartment was a humongous rooftop. We carried out drinks on to the roof and were standing there. She had a glass in one hand and her other elbow was touching me. Her eyes were closed and she was just feeling the cool breeze.It was a good feeling and I held her hand. To this, she smiled, turned around and gave me a big hug. I could feel her aroma mixed in the breeze and it was a good feeling. She was feeling a bit cold so she asked me to hold her from behind.While it sounded great and somewhere upwardly flirty but a hot woman in your arms who is asking to be hugged is a dilemma. My dick.
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