Crystal's StorySite


March Madness

by Andrew J


So another March Madness is in the air, and I am hanging out with some of my buddies at our favorite bar after work. Everyone is working on their brackets for the upcoming tournament, and trash talking is a given. This year, some new women were with our group playing with the brackets. One of my more shady friends, named Angie, was singling me out while working the brackets. That is where 'the bet' first came up. I looked at her picks and laughed as they were being made depending on the colors of uniforms that the teams wore. She said if my brackets were so good, then I wouldn't mind a friendly wager on the tournament. In front of the others, she called me out under unspecified terms. I felt that I needed to defend my basketball intellect, so I accepted. My terms were modest, that she would have to wear a jersey of my choice to work and go out on a date with me. Her terms were not disclosed in front of the group. She said that she needed to think about what she wanted. An agreement was reached, and we both shook in front of everyone.

Later that night, I took her home from the bar. She looked at me with quite a devilish grin and said, 'If I win our bet, you will wear a dress with all the accessories without any complaints.' I tried to voice my complaints to the terms, but she again attacked my basketball intellect. To which, I had to defend so I agreed on it again.

The month passed way too fast. I was having so much enjoyment watching the games, that I had forgotten to keep track of my progress on the bet with her. It came down to the last game before I realized that we were tied up on points! That there was only one game to decide the winner of the bet. So, I decided that I would ask her to watch the game with me. Just so there was not going to be anyone else around, and the winner would be crowned in private. Of course, the loser would know and have to accept the terms of defeat in the same manner. You could imagine my relief when she accepted my proposition. The only catch on her end was that we were going to be watching it at her house so all of her 'clothing' was on hand. I accepted thinking that there was no way in the world that her team had a chance.

The night of the game, I washed up really well, packed up the jersey that I wanted her to wear into work the next day, and thought about all of the things that I wanted to say in front of everyone declaring my basketball intellect dominance. After I arrived at her house, I looked at the set up that she did for the game with me. She really went out of her way to act like a super fan! There was all of the food that I could imagine to watch a game with, some beers to keep us hydrated, and rival foam fingers to taunt each other with. I couldn't help but notice that she was wearing a tank top of the team she picked without a bra underneath. I started to think that I had died and gone to heaven! Then the worst thing in the world happened. From the opening tip off to the final buzzer, my nightmare game occurred before my eyes. Her team won by 15, leaving me to wonder what I was going to be wearing. I tried to do damage control and talk her out of our friendly wager, but she pointed to the bag that I had brought claiming that I would not have been so generous had I won.

So I agreed to hold up my end of the bet. First she handed me a bottle of this cream that she said would remove all of the unwanted hair from getting in the way of the 'full effect'. I mumbled on the way to the bathroom, but was comforted by the fact that she followed me in to help me clean myself. I enjoyed every minute of staring at her amazing naked body rubbing all over mine. I almost lost it when she even de-haired my private areas. Her smile melted me into a state of bliss. As we left the shower and dried off, I stood amazed at how smooth my skin was. It felt almost like a baby's bottom! From there we went into her room to continue the transformation. I felt a shiver run up my spine as she took out the under wear that she expected me to put on. I protested until she attacked my honorability. I had never backed out of a wager before, and everyone in the workplace knew that I lived by my word. So I allowed her to walk up to me holding these two huge breast forms. I stood still as she placed them against my chest and held them into place. There seemed to be some sort of sticky fluid on them that held them into place as she let go. I looked down in amazement at how real they looked, and just had to touch them to see if they felt as just as real. Meanwhile, I felt her sliding my manhood into this strange looking silicon form. I didn't even look to see as my mind was still wrapped around the look and feel of the 'breasts' that I was given. Then, I felt her glide my legs into these black, lacy silk panties. Without my manhood showing though the silicon pussy form now stuck to my crotch, the panties gave me a truly feminine look to the casual observer. Still, I couldn't see what she was doing. I just couldn't get over the 'breasts'! My obsession over staring at them were only increased as she placed a corset and bustier on me. They were obviously a little small, and pushed my chest even higher. She slapped them to test their realism. Then smiled as they jiggled in response just as real ones would.

My mind was truly reeling from what was happening to me. Not even paying attention to what she was doing pleased her greatly. I felt the sheer black nylons being pulled up my legs, and the snap of the connections to the garter belt. My attentions was grabbed by the shiny, blue rubber dress that she pulled from the closet. I felt like I wasn't myself as I lifted each of my legs to allow her to pull the dress up to settle on my waist. I just watched as she placed some lotion on my arms before slipping them into the dress. Soon, my hands showed out the ends of these skin tight sleeves that felt like they were slowly drying to my arms. I looked down as she pulled the neck portion of the dress over my head, watching my 'breasts' through the small open area showing off the cleavage. I heard the zipper of the dress, and felt the tension of it increase as I was sealed inside. I didn't even feel my feel being placed into these knee-high, 4 inch heals. She giggled as she placed glue along the zipper which would force me to wear them longer.

She then lead me over to this table, where I saw her make up counter and other strange things. She took my hands and started forming my nails for these plastic tips. I watched in amazement as she quickly placed these fake nails on me along with red nail polish. Then she moved her attention to working on my makeup. I stared at her as she talked me through applying mascara, eye liner, eye shadow, foundation, blush, and a thick layer of red lip gloss. Then, she took out this shoulder length brunette wig and walked behind me. I didn't follow her, but felt her place the 'wet' wig on my head and used a blow dryer to fix it to her liking. When she finished, a broad smile crossed her face as she took a step back to see what she had done to me. I wasn't even thinking about everything that was happening to me, until after she finished with my makeup. But since I was in no position to protest at this point, I let her finish working on me. As she walked over to the corner of her room, which had a full length mirror in it. I took a second to look down at myself, but it really didn't hit me that I was in trouble until she call me Tami. I looked up and stood in astonishment. I couldn't even recognize myself!! I looked like a gorgeous, buxom beauty!! I stood there, mouth wide open until she broke the silence. When I looked at her again, she was swinging a shiny ruby necklace in front of her. Immediately, my eyes were attached to the swinging gem. 'You are becoming very relaxed. You are feeling safe dressed like a woman. With each inhale of cigarette smoke, you feel even safer dressed this way. You are so relaxed as Tami. You love the way you feel as Tami.' I fought the feeling, but in the end finding myself mindlessly repeating her phrases. Allowing them into my sub conscious where they were forming memories where they shouldn't have been. As she continued, I felt safer and more relaxed by the moment as she lit up a cigarette and started blowing plumes into my face.

After finishing the cigarette, she walked over to me. 'With this locket secure around your neck, you will be Tami. Your formal conscious will be imprisoned within your mind, only able to watch as Tami interacts with the world.' I couldn't even struggle as she maneuvered her way behind me and dangled the necklace in front. She whispered into my ear, 'Tami loves being an exhibitionist. She loves to smoke cigarettes and cock. But don't worry Tom. You will only be locked in your mind for a week or so until the glue wears off. Then, I will release you on the condition that you marry me. Of course, if you try something funny, I am sure that you will be amazed how fast that I can make this a permanent condition.'

With that being said, she connected the necklace behind my neck. All of a sudden, it was like I was a spectator in my own body. Angie offered me a cigarette, and I took it as though I had been smoking my entire life. She then asked if I was ready to go out for the night. My conscious was screaming 'NO!!!', but my body answered yes as I grabbed a purse. In the purse was an amazingly good fake id with my drag photo, some cigarettes, money, and extra lip gloss. I continued to try to fight my own body, but with each inhale of the cigarette. My mind became more and more accepting of the deal, and more and more secure about walking out in a fetish dress. The next thing I knew, Angie put her hand on the small of my back and gave me an extremely sexy smoky kiss. I found my body sucking the smoke deep into my lungs. Then, at the break of the kiss, releasing it towards the ceiling in a slow, tight stream. 'Ready', she said. My conscious was falling deeper in a fog from the smoky assault. 'I am ready when you are.', is all that my body was able to say. With that, we walked out of her house and into a world that I was to accept before becoming the loving husband? of my new bride. The consequences of rejecting the proposition were too great for me to fathom at the moment. If I only knew what she was going to put me through during my week as a woman....




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