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A New Role For Alan

Alan never expected things to go this far in such a short time. It was barely a month ago that Sandra had found the files on his computer. He had been in the shower and she decided to log on to her Facebook account from his laptop. His browser history showed the transvestite forum he was active in and a quick search for picture files found his hoard of crossdressing pictures and stories. There were even some pictures he had taken of himself wearing her panties. When he came out of the shower his heart had sunk into his feet but she wouldn’t even look at him. She just kept on going through all of his stashes. He tried to explain, how he enjoyed experiencing what girls feel like when they dress but his pleas seemed to fall on deaf ears. Then, to his horror, she copied the pictures of him wearing her underwear to a USB drive and got up to leave. “We’ll see,” was all she said in a tight-lipped voice as she walked out the door. He didn’t hear from her for three days and then she called and told him she was coming over. He was relieved but something in her voice sounded different, more confident.

“I’ve been checking up on the Internet just why it is that man would want to wear women’s clothes,” she began. “That’s quite a little fetish, isn’t it? Alan began to respond but she cut him off. “If you like wearing girls’ clothes so much then you can become my personal assistant,” she continued. “And like any good assistant, you will dress appropriately. You will shave your body and manicure. You will wear either dresses or skirts since you like them so much, and find yourself a wig until your hair grows long enough. Apply make-up, I don’t want a sloppy-looking assistant.” “Look, I admit I like wearing girls’ panties but this is going too far,” Alan protested. “Yes, so I noticed. If you don’t comply I’ll put those pictures of you in my stolen underwear up on Facebook,” Sandra retorted and Alan knew he had no choice. Even since then Alan had been slipping further and further into his role of the young, sexy, feminine assistant. He wore only women’s clothes when they were together and he had begun acting more feminine under Sandra’s careful tuition. He prepared her clothes every day, as well as his own, and they were both quite happy with the arrangement. Now he sat on the edge of the couch with his hand politely in his lap, looking every bit at his new role, as she explained to him that she wanted him to prepare dinner for her and her new boyfriend…

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