Crystal's StorySite


Michelle Rose Arrives

by Michelle Rose


It was our anniversary and we had made plans to get away for a couple of weeks. I arranged to leave work early so Kim and I could get a jump on the weekend traffic. When I arrived home I found a letter from my wife informing me that she had packed for both of us and was doing some last minute errands. I was instructed to take a taxi to a local resort and wait for her in room 212. In the envelope I found a hotel key to room 212. As I continued reading my excitement made my hands tremble and my cock awaken. I was to go directly to the hotel taking only the clothing on my back. It was signed mistress Kimberly! By this time I was ready to come, my erection was full and hard. Just thinking of the sexual perversions I would be subject to was too much.

I began stroking the shaft of my penis and made for the nearest bathroom. Inside, I quickly pealed off my cloths. And, with the help of some soap and water my cock was soon caressed by my expert hands. As the stroking of my shaft intensified I became lost in the imaginary embrace of my mistress. Under her tutelage, I would soon be fulfilling my dearest fantasies. My body shuddered as come exploded out of my penis and my knees almost buckled. After I caught my breath and I was able clean and dress myself. I called a cab and went to the hotel.

I went to room 212 and unlocked the door. As the door opened, I became aware that my wife's perfume filled the air. I went inside and closed the door . When I called to her, my wife, a very tall and elegantly dressed woman emerged from the bedroom, saying her name was "Stephanie" and "not Kimberly." I apologized for intruding saying "I must be in the wrong room". As I turned to leave she called me by name and said "there is no mistake"! The surprise must have be written on my face because she smiled and said we needed to talk.

She offered me a seat and began telling me that she was hired by my wife and that Kimberly would be here to pick me up at 6pm. If she was going to complete her assignment we would need to start right away. What assignment? Complete what? I asked "what this had to do with me"? Again she smiled, a coy little smirk and she motioned me to follow her into the bedroom.

As I entered the room I noticed the bed was covered with clothing. Women's clothing! There were dresses, skirts, sweaters, lingerie and many pair of shoes! I saw pumps, sandals and boots. Not a single pair had heels less than 4 inches. On the dresser there was make-up, jewelry, hand bags and and several wigs. She led me to the closet and showed me a full length fur coat, I later learned it was fox , as well as a very soft and supple leather coat. When I asked her "what was going on"? She told me that it was her job to transform me into the "girlfriend" that was going away with my wife. These were the outfits that I would wear over the two weeks! She went onto tell me that Kimberly had confided in her about my crossdressing and that this vacation would be a chance for me to be a "girl" for awhile. If I refused to cooperate with her she would just leave and let me explain it to Kimberly. She went on, telling me that if I did not "get changed" and "I was still a boy when my wife arrived", Kimberly would never allow me to crossdress again. It seems my wife had set this whole thing up and was not going to let me out of it without a little fun. As I thought about it I began to get excited and found myself fantasizing about all the beautiful clothing on the bed. Kimberly knew my taste in women's clothing and from the looks of things she had shopped well! This was getting exciting!

Stephanie, seeing a lump in my pants, smiled that little smile again. "It seems you would rather be a lady than man", "is this right ?" she demanded!. "I've known that I was a girl since the 4th. grade" and spend as much time "dressed up" as I can. "This, I can understand" and "that is what brings us together this afternoon", she took me by the hand and said "dear little boy, lets make you into a lady". Entering the bathroom I found an assortment of razors and depilatory creams. I was ordered to strip and did so without a second thought. She asked me how tall I was and how much I weighted. The reply was 5'7' and 160 lbs. She said I was a "runt of a man" but I should make a fine girl. Then I was told to shave my face, throat and neck. This I did twice and after I finished a very feminine smelling lotion was applied to my face and throat. It soothed my skin and made it look "milky white". It smelled like flowers and had a very calming effect. Next, a small area on my thigh was treated with a depilatory cream and after 15 minutes was washed off. With the hair completely removed from the spot and no reaction on the skin, my entire body was covered with the depilatory cream. The next 15 minutes was agony standing there naked with this beautiful woman next to me.

While we waited she told me how lucky I was to have such a beautiful and wonderful woman as my mistress. She told me of the lonely and rejected transvestites she had worked with over the years. Most were alone after being rejected by their wives and families. I told her I knew all this and was truly grateful for Kimberly's understanding. She also told me that in gratitude for all my wife's efforts I should make myself into the most beautiful image of a woman I could. She asked "if I liked to be fucked like a girl" and I said that "I loved it when my wife fucked me". She smiled that smile again and told me to shower.

As the water hit my body my hair was washed away. I had only been completely shaved once before and longed to do it again, now it was done! I love being totally shaved, it makes everything feel so silky and smooth next to my skin. I think it is also one of those things that in our society, helps define your feminine side and so, is a very desirable for the crossdresser. I toweled off and that lovely lotion was applied from head to toe. This moisturizer really softened my dry course tough skin. I was then handed a pastel pink gaff and after proper adjustment, my penis was completely hidden, giving me the flat pubic area of womanhood. I love the way a gaff flattens your front and allows a skirt to fit properly from the tummy down. Next, Stephanie helped me slip into a pastel pink chemise, it had lots of black lace trim in all the right places. It was very short, just covering my bottom. A matching floor length rob and a pair of pink satin mules, you know the kind with the "puffy stuff" over the arch of the foot, completed my outfit. I was led out of the bathroom and ordered to sit on a chair in front of the dresser.

While I was in the shower Stephanie was preparing all the stuff she would use to erase my masculinity. Most of the cloths and other items were now packed in two large suitcases, with a smaller one open and empty. On the dresser there was makeup of every type. I saw what looked like short fake nails and nail polish in several shades of red. I noticed several tubes of lipstick, I hope they match the nail polish. Behind my chair, on the bed, there was an assortment of lingerie, corsets, stockings, thongs in white and black and some in red satin, all with delicate lace trim. There were several body shaping undergarments, which would clearly help me obtain a womanly hourglass figure. I also saw 2 pair high heels, one was a pale camel pump with at least a 4 inch heel while the other pair was similar, but in black. For clothing there were just two outfits left on the bed. The first outfit was a black leather miniskirt, which looked to be very tight and would clearly be way above the knee. This was matched with a cranberry red turtleneck sweater and it looked to be soft, very soft cashmere! With the black heels this would be a "fuck me, now, outfit"! The other outfit was very conservative, a camel brown wool skirt, also tight but somewhat longer, maybe just above the knee. This was matched with a turtleneck sleeveless shell and cardigan sweater set, also a camel color. Either way I would love to be dressed in these cloths. I began to fantasize about being a woman, all dressed in these beautiful cloths. My lips would be red and match my nails, my hair cascading over my shoulders in seductive curls. I would welcome my wife's had as she slipped it up my skirt and pulled my panties aside. Her finger would explore my dripping wet pussy. I know she would love to lick and suck my clitoris just as I do to hers. Finally after much kissing and sucking she would fuck me with her dildo and then roll me over and fuck me again, this time in my tight ass. OOOOH how wonderful!

As I sat in the chair, I was brought back to the "here and now" by a soft feminine voice speaking. As I looked up a tiny oriental lady walked in from the other room. She was very beautiful, maybe 5 foot tall and very slender, she could not have weighed more than 90lbs. She had long black hair and beautiful almond eyes. She was dressed in a scarlet red Mandarin jacket and skirt set that was embroided with golden dragons. Her shoes were matching red pumps with a 5 inch heel. She glided across the room. Introducing herself as Miss Li, she instructed me to place my feet on a small stool she brought over from the corner. Miss Li explained that she would do my hair, nails and make up that would turn me into a very "girlie" girl. She began at once with a pedicure. After some filing and nail shaping she massaged a oil into my feet. It felt wonderful and soon I was back in fantasy land. While I imagined that I was a princess, and Miss Li my servant she expertly painted my toe nails with a berry red nail polish. A coat of "quick dry" and she turned her attention to my fingers. She told me there would be another coat of polish on my toes but first she would do some work on my hands. My finger nails were far to "manly" for her to do a good job and it was decided that nail wraps would be needed. These would be applied and stay on until they were removed. Quickly the false nails were applied and finished to a very ladylike shape. The same berry red nail polish was applied. Both toes and fingers were given a second coat and my transformation took another step forward.

At this point I was getting used to the idea that this would be no ordinary crossdressing game Kimberly and I are used to playing. This was something different. I knew in my heart I would walk out of this room in full drag and not be a "man" again anytime soon. I felt an ache in my groin, thank goodness my "boyfriend" was tightly constrained by the gaff I was wearing. Mistress Stephanie gave her approval and said the nail polish would go very well with the sweater and leather skirt and told Miss Li to begin my hair.

Since I like to wear women's clothing, I keep my hair long, about shoulder length and when not dressed usually wear it in a pony tail. When Kimberly and I play "dress-up" a little styling can usually make it look very womanly. Not this time, Miss Li took out scissors and soon was clipping away. I was told bangs would help with the illusion and some light brown highlights would be very stylish. Since my hair has a natural wave to it no curling was needed. The cut and coloring took almost an hour and a half and after a blow dryer my new hair-do was very fluffy and reminded me of the big hair days of the 1980's. Each time I moved my head the gentle brushing of my hair on my neck was heavenly. Mistress Stephanie was satisfied and instructed Miss Li to begin my make up.

First, Li began to shape my eyebrows, one hair at a time was plucked. Now I understand just what pain is! Then, to my surprise, she began to "deforest " inside my nose and ears. It hurt so much! All the while Miss Li kept telling me how hard it is to be beautiful. Finally, she was satisfied and gave me a few minutes to rest and wipe the tears away. Next, she began applying liquid makeup foundation to my face and throat. This, applied in two layers really hid any sign of my scant beard, all the while the odor of the makeup was like an aphrodisiac and soon I was dreaming of being a girl in that little skirt and sweater. How much excitement would I be forced endure before having the opportunity to "come" again, I was sure glad I took care of that before coming to the hotel. Soon, eye liner and mascara were being applied to my eyelids and lashes. My lashes are a bit skimpy for a lady, but thanks to Miss Li's professional skills they were soon much fuller. The eye liner really brought out my eye's. Eye shadow, in three complementary colors and some blush to accent my cheek bones was next. My lips were outlined with a lip pencil and berry red lipstick was applied. I love the taste and smell of lipstick. A spray of perfume, Este Lauder, White Linen and I was ready to be dressed. My head was spinning with excitement!


Mistress paid Miss Li and she was dismissed. Li turned to me and said ,"since she started to live as a woman, she was very happy and said that I would also be very happy as a girl", and left the room. I was shocked that this oriental beauty was a "special girl" like me. I

Mistress Stephanie looked me over and seemed happy with the way things were going. She asked me, if I was enjoying what was being done to me? I replied "this was what I had dreamed of for years". She said, she knew this to be true and removed my robe and chemise. I was standing there in just my gaff while she examined me. She told me I had nice breasts and that with proper technique I would be able to have nice cleavage and wear some revealing blouses. But, time was short, it was already 5pm and Kimberly would be here within the hour. It was time to get dressed.

The hardest part of passing as a woman are the mannerism and the way you walk. Men, being dominate will strut into a room, as a woman, you must be submissive and meek in all your actions. Kimberly has been instructing me on these techniques for the past several years and now I must make a change from my male self into the woman I want to be. Can I do this? I knew I could! I hear Mistress Stephanie speak, "I am sure you are unaware your wife thinks of your female self as her sex kitten and you are will be dressed as a woman for the next two weeks. She will do with you as she pleases. Do you understand? I nodded, yes. "Good" was all she said leaned forward, whispering in my ear, " it's cold out tonight, I want you to think of me, and what you allowed me to do to you, when the cold wind sweeps up your skirt bites your cute little ass".

She picked up the red satin corset and unhooked the front and walked in back of me. Stephanie opened the corset and placed it against my back and had me hold it in place while she went around front. At this point she removed my pink gaff and replaced it with a matching red satin one. Expertly, she adjusted the gaff and my manhood was gone once again. In front of me, she began fastening the "hook and eye" closure and the zipped the zipper. I soon realized this corset was different from the type I usually wear at home. This was long, about 12 inches and would shape me from my hips to just under my bust. It had heavy boning below the bust and the top part was more a bra than corset. The cups were designed to hold silicon breast forms and from one of the draws mistress produced two silicon tear shaped breast forms and slipped them into the cups of the corset. They were heavier than I imagined. But I loved what they did to my chest, or, should I now say bust. They were not very big, but big enough. Maybe 36 C or D cup. Next came the fun, Mistress walked behind me and loosened the draw strings on the corset. She told me to take a deep breath, blow out and hold it. Slowly I felt the corset tighten around my upper abdomen until I thought the laces would break. After she tied it off and I was allowed to breath, it was difficult, but after a while it became natural to breath "a little shallow".

Next, I was handed a pair of black stockings, they were sheer with beautiful lace around the tops. Mistress told me she knew I could put these on and left the room. Like a good girl, I rolled them and slid them on my freshly shaven legs. It was very difficult doing this with my new fingernails, I hope it won't be to long before I get used to them. Once the stockings were on, my legs felt wonderful. I straightened them and hooked on the garters from the corset. I just love the little red bows on the ends of the garters. I must admit it was very difficult bending over to reach my toes with this corset so tight. But, when I saw my painted toe nails I forgot my troubles and happily went to work putting the stockings on. By now, Mistress Stephanie was back and commented how nicely I had done.

Then, when I thought I was safe, I was again directed to breath out and hold my breath. This time the lower draw strings were tightened. After they were tied breathing was very hard, short and shallow was all I could manage, but again soon it became very natural. I am sure glade I keep myself trim. Mistress stepped back and gave an approving nod of her head after a careful inspection of her handiwork. I was allowed a quick look in the mirror. With my body completely shaved, my hair in its new style, my face all made up and the corset and stockings I could not believe the change. Instead of looking at me, I, was looking at a fairly attractive woman. Is that me, Yes!!

Mistress Stephanie, took one of the half slips from the bed and helped me step into it. It was black and the front was reinforced. This will help shape your tush and hips and give your "boyfriend" a little extra camouflage. It fit like a skirt and with the built in padding gave my tush and hips a very womanly shape. I was happy to see that the tops of my stocking were covered. Since the skirt looked so short, I was worried that the stocking tops would show below the hem and this would make me look very slutty and "I am not that kind of girl". Now comes the crowning moment, the item of women's apparel that makes all transvestites jealous of real girls. Mistress picked up that beautiful leather skirt and unzipped it. She said I would come to love this skirt, not only is it made of very soft leather and was lined with satin, but, several of the outfits I would be made to wear over the next 14 days would be based on this skirt. She knew my love of skirts, dresses were wonderful, but, skirts are what I really love to wear. My wife really thought of everything. With a little help, I quickly stepped into it and slid it up, a quick zip from behind and it was on. I loved it at once, tight in all the right places, but not to short, coming to around mid thigh, it was very flattering. The padding filled it out and from behind there was no chance I would not pass as a woman. My "boyfriend" was hidden and I felt like a lady. The sweater was next. I thought how soft it was as it brushed my cheek when I put it on. I noticed it had been sprayed with my new perfume. It was cut short and came to the natural waist created by my corset and looked beautiful. My hair received some quick repairs and mistress seemed very happy with the results.

Stephanie, approving of my transformation asked, If I could walk in 4 inch heels. As I long time tranny, I had mastered walking in heels some time ago. And, because of Kimberly's acceptance of my desires, I've had a lot of practice and developed a very feminine walk. I was once again instructed to sit on the chair and mistress Stephanie handed me the black pumps. As my painted toe nails and stocking clad feet disappeared into the shoes my heart skipped a beat. I love the slender shape my foot and calf take on while I'm in high heels!

I was asked to stand and told to walk around the room, as I did so, I felt my hips begin to sway from side to side in my practiced walk of womanhood. I also felt and heard the soft "swish" of my lingerie sliding across each other. As I approached the door to the room I saw my reflection in the full length mirror on the backside of the door. Looking at myself, I knew I would never be able to be a straight "guy again". The image I saw, told me this was the woman that has been hidden inside me and she would never again hide under denim and cotton. I was beautiful! My hair was long, soft and with the highlights, very feminine . Miss Li had done a excellent job with my makeup and I loved the shades and colors she had used. There was no trace of my scant facial hair and my eyebrows were perfectly shaped to my new face. As for my body. WOW !! This new corset and bust line were to die for, my hips and bottom were full and round under my skirt. I turned, more of a twirl, and admired my backside in the mirror. I had the hour glass figure of a lady. This is to cool!!

I turned and found Mistress Stephanie smiling at me and she said I looked "lovely". "Now come here and we'll get some jewelry on".

For starters you need earrings, since your left ear already has two holes all we have to do make two more in your right ear. I submitted to the piercing without a word and soon I was wearing a diamond stud and large gold hoop in each ear. The new feeling of such a large hoop will take some getting used to, but I am woman enough for the job. Stephanie then handed me three gold bangles which she told me to place on my left wrist. Each time I moved my arm they gently "clinked" against each other. Next she put on string of pearls which hung down between my breasts. She also had a couple of gold rings with semiprecious stones, both red and put one on each ring finger. I can see this whole outfit was put together well, very well. I'll have to give my wife an extra special "licking" for all her efforts to make me beautiful. To complete my jewelry she placed a fine gold chain around my right ankle. I felt beautiful. I asked for another spray of perfume and Mistress quickly obliged.


Now that I was a lady, a black leather handbag was prepared with all the makeup and other "girl" stuff I would need. My male" drivers license, cash and credit cards were arranged in a ladies wallet and placed inside. At this time a knock came at the door. Mistress Stephanie said it would be the bell hop coming to get my luggage and instructed me to let him. Nervously, I went to the door and opened it. In the hall the bell hop smiled and said "good evening, mam, may I take your luggage to the front?" I pointed to the bags and Mistress Stephanie gave him $10.00 and said "I would follow him down in a few minutes". He took the two large suitcases and the smaller one with the remainder of my things and left the room.

Now that we wear alone, Stephanie placed a red satin scarf around my neck and went to the closet and held the fur coat open for me. As I walked over I could imagine the embrace of the silk lining. The gentle caress of the fur on my newly shaven and stocking clad legs. I slid one arm in and then the other. I can only say the soft hairs of the coat tantalized the exposed skin on my legs and neck. Mistress fixed my collar and hair.

Mistress Stephanie said "now that I was a truly beautiful woman, I should always behave in a ladylike manner. I would have lots of work to do, but with some effort I could live as the girl I dreamed of being. She went on to tell me that Kimberly loved me and enjoyed being with me but also enjoyed the softness of another woman. So the fact that I crossdress, is, very exciting to her and she looks forward to having a "girlfriend", lover and husband all in one. I should be receptive to my mistress's dominance and to satisfy all her sexual needs. If I was able to do these things, then she would allow me to "dress" whenever I wanted. She told me that we would meet again and kissed me on the check. She also told me that, Kimberly was waiting in the lobby and opened the door. With my purse in hand I took a breath and walked into the world as Michelle Rose.




2004 by Michelle rose. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.