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He really felt that he couldn’t afford to fail this time. Roger wasn’t a geek or ugly. In fact he was quite handsome and had several friends. He was a little taller than average with light brown hair and deep blue eyes. He was kind and positive. People in general liked him and he had a reputation for being a nice guy. But he was quiet and shy. He also lacked confidence. Girls thought of him as the guy to have as a friend, not the guy to date. He had heard the line, “Let’s just be friends,” too many times. The girl he was going to ask out this time was Nancy. She was nice, pretty, and smiled a lot. Nancy was actually younger than him, being a freshman. He thought that gave him a better chance of going out with her. He had to try. Roger spotted Nancy, swallowed, and headed toward her with some flowers he had picked and a Valentine card. As he walked in her direction he failed to notice a couple of girls he knew watching him and giggling to themselves. He reached Nancy. She looked at. In theoffice I am Kevin and everyone treats me as a guy. I do push theenvelope though and wear women's slacks, women's jeans, panties everyday and usually at least 3-4 Inch heels covered by my long pants. I havenever crossed the live wearing a skirt though although I have always hada tickle in my groin to try being Karen for a day. Who would really careas long as I did my job?Kevin was given his task to travel to Phoenix on Wednesday, meet withthe software folks and have the problem fixed by the following week. Inall honesty, I could have fixed it over the phone lines but this gave mea chance to travel as my alter ego and be Karen in another city while Ipretended to fix the problems as Kevin. Confused, well let me say I hadthe whole thing under control and I was going to be as much of a womanas I could in a beautiful city, surrounded by lots of dick.I got home and packed all of my (Kevin's and Karen's) things for thetrip. It took two suitcases for this trip. I really wanted to show.
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It just started to hurt when she stopped and pulled her fingers out of me, keeping the dildo in place. I could feel her repositioning her hand and then she pushed it further into me The penetration caused me to gasp in surprise, just as her fingers found my anus and slid in beside the dildo. She kept up the pressure and got her fingers in to the knuckles and stopped. She held her fingers and the dildo there, and then started wiggling her fingers. Indescribable sensations flowed from my anus to my dick, causing it to jump to attention. Slowly she withdrew. Once her fingers were out, I could hardly feel the dildo, just the last bit of it when it popped out. She applied a bit more lubricant to the dildo, and quickly put it back in; which was easy to do, since my anus was still gaping somewhat. It went in quite a bit further than before and I gasped with pleasure, willing myself open to receive as much of her as I could. She moved it in and out and back and forth and then suddenly.

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