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"I really can't do it, " she thought. "It would be too embarrassing."She put down her cup and headed back to the bedroom. She looked through her closets selecting five skirts which she lined up on the bed from shortest to longest.The first was a miniskirt, black and tiny, appropriate for a night out on the town with a really pretty pair of panties underneath, panties intended to be seen. The second was a plaid pleated skirt, more of a schoolgirl costume than a work skirt. It reached about a third of the way down her thighs. The third was another dressy skirt, black again, coming down slightly longer than the schoolgirl skirt. The fourth was a burgundy skirt, a little short for work, but she could probably get away with it. The fifth was black again, and reached a couple of inches above her knees."The shortest that you can get away with," he had demanded. She pulled down her pants and slipped on the fourth skirt. Then taking a deep breath, she reached under her skirt and pulled down. " For a moment silence filled the room. Ashley was thinking hard to find the right words. Finally she said"I want to really feel you as you enter me. And that one looked right for that. The last one is too big and the other two look too small. And as long as it's you, I don't mind any pain.“I smiled and picked up the belt. I stood up, put it on and began screwing on the dildo. Ashley's eyes followed every movement I made, torn between curiosity, excitement and fear. I kneeled down between her legs and she assumed the missionary position. Not a single word was spoken when I carefully started to rub the dildo up and down to lubricate it. Instead she closed her eyes and inhaled deeply a few times. I gently pushed it against her hole, again just enough to slightly get the tip in. Then I leaned forward. Our faces almost touched"Are you ready?" I whispered after kissing her. Her eyes opened and for a moment we were starting at each other. Her arms reached around me and held me tight, then.
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