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Mark had never been outside the house in women's clothes before. He hadgotten comfortable dressing around Cindy over the last six months. Markwas a young twenty three year old, who liked mature women. Cindy was afriend of Mark's mothers and she was in her early forties. Theirrelationship had started off quietly, with nobody knowing about the twoof them but slowly had leaked out with time, Cindy had found out aboutMark's dressing desires and had been very sympathetic to him. She wouldhelp dress him up and listen to him talk of fantasies of giggling girlslooking at him or shocked women forming opinions of him based on whatthey saw. She was the type that wanted to bring some reality to hisfantasies, even surprising him at times, but keeping him safe.Cindy opened the door and stepped out. She had to go around and open hiscar door as he sit there having second thoughts."C'mon Mark. Let's go," she said helping him stand up.Mark was wearing a dark blue sweat pants and sweat shirt set. The. She had seen our stunned looks, gave a dirty chuckle and started grinning broadly.“Sorry I don’t have a tavern wenches’ outfit, this is the nearest I can find,” She held her arms high and wide, a tin in each hand, and turned slowly round. The raised arms caused the dress to hike up, clearly confirming the fact that she wore nothing underneath it. “will it do?”Neither of us said a word. Bob sat there doing an impression of a goldfish and I probably looked much the same. I was so amazed at the sight of her. It wasn’t just the outfit; she knows I like her to dress in tarty make up and sexy clothing, and this was an outfit she frequently wore to tease/please me. It was the fact that she was wearing it now, in front of Bob and the way she was behaving. Ok, she was somewhat drunk, but it was so totally out of character. I have to say, she looked fantastic, standing there like that, flaunting herself. Only in my wildest fantasies had I ever imagined that she would do anything like that. I.
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