So many sissy stories start with the wife or girlfriend or significant someone catching the sissy in the act. This one is not different. It was New Year's Eve. Mitch had enough partying at the office, and said his goodbyes early. He never liked office parties, the women gravitated to certain guys but never to him. He didn't mind that too much. So he told himself. He did have one person who befriended him, but he suspected it was out of pity. She had heard others talk behind his back and often refer to him as Mitch the B*tch. Shilo would bring him coffee when she sensed Mitch was having a bad day. He loved smelling her Poison perfume, and admired the way she dressed, walked, and basically stayed different from the office gals. She was not intimidated, and dared to be different. Over the years, they became confidantes, and she often dragged Mitch along to her salon appointments. She would catch an odd look of longing in his eyes as he watched the manicurist shellac her nails and toenails in the wild colors she chose. Shilo was aware there was something different about Mitch, and that's probably why they clicked so well. He learned he could trust her and she would not betray him. From time to time, they would even sleep over at each others apartment, after visiting too late into the wee hours. That's why he eventually gave her his apartment key. This night that would be a grave mistake in judgement. Or would it? So the office party was a drag. Shilo watched Mitch becoming more withdrawn as the night wore on, and he was drinking one cocktail after another. She watched him say his goodbyes and exit. Was he going to be alright? She had friends who drank when they were depressed, and she never liked that combination. She always believed that you could confront that which was troubling you using your own inner strength. But she was innately strong. Some people weren't. Those were the ones that needed a guide.
Mitch arrived home, and plopped heavily into his armchair. His apartment only afforded a few pieces of furniture, and the living room served as his office, studio, and sometimes even his bedroom. Tonight it was going to serve as his bedroom. He was drunk. He knew he was drunk, and luckily he decided to come straight home. A drunk person wandering the streets alone on New Years was not safe in his neighborhood. He was on an upper floor, and he looked down on the city, imagining all the couples celebrating. Mitch began to wonder why he wasn't one of them. Am I so repulsive? Am I some kind of freak? In his alcoholic fog, he tried to make sense of his fate of being forever alone. He began to list all the things that might qualify him as a freak. Yes, it went even back to his childhood, when bullies called him a "sissy" and made fun of the way his mama dressed him. He didn't understand that his mother really wanted a girl, and she sent Mitch to school in very girly kinds of outfits, which he came to prefer, himself.
"THAT'S IT!!!" Mitch exclaimed out loud, "I'm a fucking sissy and everyone senses it!" He poured himself a gin and tonic and stood at the window again, this time a tear rolled out his eye. "I resolve to destroy the sissy in me!" Mitch said out loud, gripping his drink. For emphasis, he added, "I Mitch the B*tch do hereby resolve!" He ran to his crowded bedroom and tore the dresses down from the back of his closet where he hid them behind his suits. He pulled open his bottom drawer and flung the bras, panties, stockings, garters, and all the other feminine garments he could afford to have, as he lived alone and no one would ever disturb his dress-up evenings. That's what he did every night he returned from work, it just felt so relaxing to be himself for once. Now he was on a mission to destroy the sissy within.
He was panting and sobbing as he felt like he was losing a best friend. He sat on the bed sobbing, and unconsciously he began to caress the soft satin for the comforting feeling it gave him. Forgetting his mission, Mitch began to desire the women''s clothing more and more. He couldn't stand it. He'd read about the futility of "purging" your clothing and he felt defeated. Yes, defeated. He could not stop being a sissy. He loved it too much. It went too deep. It was part of who he was, and to hell with his coworkers. He slipped into the feminine clothing, lovingly slipping on each item. When he finished, he looked into the mirror and liked what he saw. He went to the bathroom and washed his tears away, and sat down at the vanity to apply his makeup ever so professionally. He had become quite good at it. He learned to imitate the "look" of his friend Shilo. If she could only see him now, he smiled. "Hey, I'm smiling all of a sudden!" he thought, and decided to have a toast to smiling. He clickity-clicked into the small kitchen and mixed a drink. Then he went to his computer and began browsing the sissy sites he bookmarked.
First, he went to look at clothing he could get cheap, usually giving him an excuse to rotate his wardrobe and keep the dress-up nights exciting. He decided not to read any more about the hopelessness of his being a sissy, but instead began reading on how to enjoy being a sissy. After another drink, he toasted out loud, "I Mitch the B*tch do hereby resolve to be the best damn sissy this city has seen!" Then he proceeded to order recordings that would help him train his mind into being the best sissy. After all, it was a resolution. Feeling very smug now, and very drunk, Mitch realized he was turning a point, where he would come off the fence. He was relieved. He wanted to do things that he read other sissies did, so he started his spending spree. Never shop when you're drunk was rule #1 he had learned, but here he was breaking his cardinal rule. He found what he was looking for. Deprived of a partner, he always go SO worked up and excited, but also frustrated. This next order would help satisfy that craving. What the hell, it's New Years. It would take up space in his apartment, yes, but it looked like some kind of sexual workout machine too.
He just clicked the "Purchase" button when he heard a noise behind him. As he swung around, his huge "Shilo" earrings swung too, and his made up eyes grew twice as huge. It was Shilo!! "What the F**K!!!" he shouted. But Shilo pushed Mitch back down by his shoulders. "Well, well well. I thought you looked a little too eager when I took you shopping with me, or to the salon. So THIS is your secret desire. How sweet. Now I have a sissy boy."
"I am NOT a sissy boy!" Mitch blurted, before realizing the absurdity of his retort.
"Well, lets see what you''ve been study so hard that you didn''t even hear a concerned friend at the door." She began to check Mitch''s browsing history. "um hmmm. um humm. I see. Okay. um humm." She went through his week of browsing and decided not to spend too much time confirming what she already had found out.
"Well, Mitch, what do we do now? This changes things a bit between you and me. I mean you can stop pretending now. I'll be coming over more often, maybe even every night. I am certainly curious about how your "exercise machine" is going to work. Maybe I''ll give it a spin myself!" She was certainly making Mitch blush. He had not uttered a single thing. Instead he began drinking straight from the bottle of gin. Shilo grabbed it away from him, and slapped him hard, "THAT IS NOT AN ANSWER!" she began sobbing, and said again more quietly, "That is not an answer, dear Michelle." She put her hand in his, and noticed that there was a bulge in his lap. Oh well, maybe he needs a firm hand too, as well as a gentle guide.
The story would go on, and Mitch would become Michelle, ever so gradually. It started with some physical changes. She knew he wanted it. Or should we say "she"? It was going to be a Happy New Year. And a very KINKY one! ;-)