Michelle Rose Arrives

by Michelle Rose

 

Morning came quickly and I was awakened by the automated telephone wake-up call. Mistress was still asleep as I crawled out of bed and headed for the shower. As I passed the mirror I caught my reflection, what a mess! I found the makeup remover and cleaned Miss Li's handiwork away. Back to being a man again, how awful! I gathered all my lingerie and washed them in cold water and Woollite soap. While I was hanging them to dry, Mistress walked in and kissed me on the cheek, adding her lovely things to the pile. She removed her makeup and brushed her teeth. Before she left, she told me breakfast would be sent up in 15-20 minutes and when finished I should join her in the living room.

When our lingerie was washed and hung to dry, I took a long, hot shower and then carefully shaved my face, neck and throat. The other areas, where the hair was removed by the depilatory cream were still hair free and very smooth. As I toweled my self dry I noticed a container of Este Lauder scented powder and dusted myself. I smelled lovely and put on my robe, slipping my feet into my glamour girl mules, I went to see if breakfast was here. Mistress, hearing me, called me into the living room where I found Mistress Stephanie and Miss Li enjoying a room service breakfast. Kimberly excused herself and went off to shower.

Miss Li was very excited and asked about the events of last night. While we ate, we talked about everything that had happened and found ourselves, giggling like two school girls. Mistress Stephanie was reading the paper when she suddenly announced, it was time to get dressed. Leading me to the closet, Stephanie open the door and I saw that the bell boy had taken my suit cases to this suite and everything was neatly hanging or laid out on the shelves. She offered me a choice between three outfits. The first, a yellow sheath dress with a deep v-neck and matching form fit one button jacket. It was very nice, made of a gabardine wool and I looked forward to wearing it soon. The second was a knit shirtdress in a bold, black and white houndstooth pattern, with an A frame skirt, it was sexy. But with my love of skirts, I selected the third outfit, a denim skirt with a pale purple silk blouse. Mistress Stephanie approved of my selection and told Miss Li to begin my makeup.

We started with my hair, brushing and blow drying, it soon looked as wonderful as it did last night. Today, was not simply another transformation, but a schooling on the proper way to apply makeup. As we worked, Li and I started talking about ourselves and our sexual desires. I soon learned that she was Vietnamese, leaving her country while still a young child. By the time she was 10, she knew of her female self. By 15, she was an avid crossdresser, secretly borrowing her mothers or sisters cloths while they were at work or out of the house. Being as small as she is, which she attributes to lack of proper nutrition, she readily passed as a girl. When she was 19, she discovered her transexuality, after some thinking, she decided to discuss it with her mother, but this proved disastrous. The cultural differences prohibited her mothers acceptance and unable to live with this, she left home and began making her life as Miss Li. She went to school, studying hair styling and cosmetics and within a year she was a licensed cosmetologist. She met Mistress Stephanie 3 years ago when she worked for Clinique at a Macy's department store. Mistress Stephanie saw through her disguise as "Miss Li" and asked "him" out for dinner. They found each other compatible and soon became lovers. LI, really desires a sex change operation, but, Mistress Stephanie enjoys "her" manhood and would only allow her to have breast implants and some facial cosmetic surgery to make "her" more "womanly". I told her she was beautiful and should not give up her dream to become a complete woman. Perhaps, one day, Mistress Stephanie would consent to her sexual reassignment surgery.

As we talked, she gave me instructions on color choice and application techniques. Under her direction I applied most of my own makeup and soon felt comfortable with foundation, blush, eye shadow, lip liner and lipstick. Mascara and eye liner were difficult, I applied and removed it 2 or 3 times before getting it right. The biggest secret I learned was to apply makeup sparingly and blend it with a Que-tips, cotton pads and brushes. Last night my makeup was very sexy and seductive, but today it was light and fresh, somewhat innocent with peach, purple and rose eye shadow. The three colors complemented each other in a way I would never have imagined. My lipstick was a light rose matching the eye shadow. A spray of my perfume and I was again feeling very ladylike.

Mistress Stephanie examined my face and hair, giving her approval, I began getting dressed. At this, she went into the bedroom and closed the door. The sounds we heard from behind the door could only be Kimberly and Stephanie enjoying the pleasures of each others body. They were very busy for 15 or 20 minutes and then all was quite. I was a little jealous and Li saw the hurt on my face.

She asked me what was my story and soon, I found myself revealing my deepest secrets. I was the middle child of three. Ignored by both my mother and father, I was left to myself. Never being shown love and affection, I soon had a disconnected feeling from my family. To this day, intimacy is still very difficult for me while being my male self, but, when in my "fem" persona, it is very easy to be loving and intimate. By my early teens, I could no longer resist the urges which drew me into my mothers closet, I have clear memories from about 12 years old imagining myself as a girl. Once inside her closet, I quickly progressed from just enjoying the silky feeling of the materials to wearing panties, stockings and shoes. In no time, I found myself wearing her skirts, sweaters and dresses. Always fearful of discovery, I soon developed anxiety and felt that there was something very wrong with me. As I grew to manhood and left my parents house I would go through cycles of crossdressing and then throw everything away and promise myself I would never dress again. I was slowly becoming neurotic and by the time I was 23 I knew I needed help. I found a gender dysphoria psychologist and began exploring who and what I was. Over the next 2 years it became evident that I was a heterosexual transvestite, this by itself did wonders to reduce my anxiety. We explored many aspects of my life and soon I was getting comfortable with myself. I began to explore the transgender world and once again had a nice collection of ladies attire and frilly lingerie. Although I felt better about myself, I kept my crossdressing hidden behind closed curtains and I was still very much "in the closet".

Dating was difficult, but, since I do enjoy the pleasures of being with a woman, I persisted. Dates were very awkward and few girls seemed interested in second or third dates. As I came to accept my desires, I slowly became more comfortable with women and dating improved. At work, I would always wind up sitting with the ladies and found that the female world was more to my liking than the macho world of men. I met Kimberly and we dated on and off for 3 years until she asked me to marry her. I accepted and we were married. I could not bring myself to tell her my secret, but soon circumstances mandated a "coming out". We opened ourselves to each other and found we were a match made in heaven! With support and encouragement from Kimberly I started my own business and 5 years later made a public stock offering. The sale of 45% of the company stock made us very wealthy. Li smiled and told me that "this was a sad story, but, with a happy ending".

She went to the closet and found what looked like a bra, but it was different, the cups were very small. She told me this would push my natural breast up and in to create very realistic cleavage from my scant male breast tissue. It went around my chest and with criss-crossing straps she pulled them tight and wallah, I had the makings of boobs. The effect was very good, but, they were very small. Then, Li took a pair of artificial breast's and held them to my chest. The combination of "my new cleavage" and the prosthesis gave me a very full chest. I put on a purple-heather embroidered bra, which had a deep front plunge and matching thong. Li added the breast prosthesis and the effect was very convincing. My natural breast was all that was visible, while the artificial breast filled in the bra's C cup proportions. Li handed me a matching waist cincher with garters and a pair of matching stockings. Expertly, I put on the cincher and rolled the stockings up my legs. Attaching the garter straps I was amazed how quickly I became used to doing things with long nails. Next, Li went behind me and began tightening the laces on the cincher. I took a deep breath and exhaled as Li tied the laces. The effect was very nice and gave me an acceptable girlish figure. I do miss the voluptuous curves the corset and padded half slip produced, but, this was much more comfortable. Miss Li showed me a Victoria's Secret catalog and opened to the page showing all my lovely undies on an attractive brunette model. I felt as pretty as the model looked.

Miss Li returned to the closet and handed me a pair of purple pumps. Of course, they had 4 inch heels and I couldn't get over the color. Purple, men never get to wear such colors, but girls do! I put them on and totally enjoyed the myself. Li brought over some make up and began showing me how to blend the makeup and create shadow to give my cleavage natural look. When I put on the silk blouse Li had me leave the top 3 buttons open. The effect was stunning! The denim skirt fit snugly and the hem came to about four inches above my knee. I felt great. Miss Li and I cleaned up the room and waited for our mistress's.

I knocked on the bedroom door and was allowed to come inside. My Kimberly was still in bed and Mistress Stephanie was lying next to her. Neither was dressed and from the scattered cloths on the floor I could tell they had wanted each other very badly. Kimberly told me there was a change in plans and Miss Li would take me shopping today. My mistress told me to buy 2 or 3 outfits for day wear with one pair of shoes if I wanted. I should also consider some accessories, like jewelry, handbags, belts, scarves and gloves. The limo would be here in 30 minutes and make sure we returned by 5pm. I was requested to close the door when I left the bedroom.

Li and I prepared to go down and meet the limo driver. Despite the desert storm last night, today was sunny and should be about 70 degrees by noon. Wearing skirts outside is different from dressing up at home and I took the Denim jacket that matched the skirt. I found my purse from last night and changed the makeup I might need and added $500.00 cash Kimberly had given me. We "girls" checked our makeup and went to the lobby.

Walking together, I felt unafraid and full of confidence. I looked forward to being seen in public a taken for a woman. This must be the kind of excitation a exhibitionist feels when exposing himself. It's a little perverted, but, the illusion we created said that "I am a woman", was very exciting. We arrived in the lobby and found the same driver from last night waiting for us. He brought the car around and the door man opened the door and said "have a nice day ladies" as I handed him a tip for his services. The driver asked where we would like to go and Miss Li instructed him to take us to the Fashion Plaza. This is the best mall I have ever seen and with all the big name stores.

Li and I began talking about what I might want to buy. I told her I would love to go to Ann Taylor. She agreed that this designer frequently had styles that I would like and that she knew a sales girls there. The ride was about 15 minutes and soon we were 2 gals on a shopping expedition. While walking through the mall, I got a kick when I heard the "clicking sound" my heels were making on the terrazzo floor. We passed so many stores, window shopping all the way to Ann Taylor. We arrived at the first stop and true to her word, Li greeted Amy, a sales girl at Ann Taylor with a hug of friendship.

The fall fashions wear beautiful. There were racks of wool skirts, long and short. The display tables had sweaters and sweater sets. There were many beautiful dresses which caught my attention too. Dressed as a lady, I enjoyed the ability to carefully look over my selections. Many times, when dressed as a guy, I would quickly make a selection and wait until I was home to try it on. While this filled my closet we ladies wear, I would frequently have to return the item because it didn't fit well or look good on me. Today, dressed in my purple blouse, denim skirt and heels I would get to try things on! As I shopped I picked out several skirts and sweater sets. I also found two dresses to try on. When I quietly asked Li where the dressing rooms were, she pulled me aside and told me she would have to tell Amy about my true gender. When I asked why, I felt a little terrified about giving that information out. Li told me we could get arrested for using the ladies dressing room. Amy and Li were friends and she knew all about Miss Li. She would take us in the back, to a private dressing room where we could not offend no one. I agreed and watched Miss Li go and talk with Amy. While they talked I saw Amy look over her shoulder and smile at me. Then, she waved me over a led us to the back.

Once out of public sight, Amy told me how much she enjoyed feminized men and thought the world would be a little better if more men acknowledged their feminine side. She showed us to the dressing room, assuring us total privacy, she went back to the store front. Li helped me undress and handed me the first wool skirt. It was a tight herringbone weave in several shades of brown, with some black and green threads mixed in. I took a size 12 and it fit very well and I loved the satin lining. Next, I tried on a asymmetrical polyester skirt that came below the knee, but knew at once it would not be going home. The next skirt was tailored wool in a dark blue. It was a classic, but, without my added tushy padding I was not woman enough to fill it out. Miss Li thought it would be a good item to have in my wardrobe and assured me with the proper undergarments it would look lovely on me. Another keeper. I tried the dresses on next, but, could not really say I liked either of them. I also found two knit shells with matching cardigan sweaters in a soft pastel pink and yellow. I had to have them both even though the did not match either skirt. As I got dressed, I asked Li if she was going to do any shopping, but she replied she was working and could not buy anything today.

We took the skirts and sweaters to the register to make my purchase. Amy mentioned that If I took the wool skirt in charcoal gray or black, I could wear it with both sweaters, since it made good sense, I exchanged the blue for charcoal gray. As she "rang up" the sale, Amy told me that since I was a "girl friend" of Miss Li, I could shop here any time and have use of the private dressing room. I thanked her and gave a her a "thank you" hug.

The next stop was a large department store, Macy's, the very store in which Miss Li used to work. Here, I would not be able to try things on, but with a department store full of cloths, I was sure I would find something. As we walked around the women's department I was aware that my fashion sense was trying to find a look. I was not sure of what the look was, but, I wanted something simple, not sexy, but still feminine. As we walked around, a blouse caught my attention. As I looked it over I realized it was a vintage-inspired Camille shirt. The fabric was gauzy and had lots of embroidery. The color was a soft beige, the label called it sheepskin. On the rack next to it was a matching Camisole top with lingerie inspired straps. The two were obviously meant to be worn together. Now, I need a long skirt, down to my ankles. As we continued to shop Li found just such a skirt. It was a soft tweed with a side zipper and fully lined, I took one in gray and held it up to myself. The skirt was full and looked very comfortable.

Miss Li said I was on my way to a "Sunday afternoon look" and that "this outfit needed a short jacket to give it a layered look", just right for the mild winters of the southwest. We went to the jackets and soon found a acid washed, black denim jacket with a floral jacquard pattern. The denim was so soft and when held up to the skirt and blouse seemed to pull the whole ensemble together. As we were waiting to pay, I noticed an crocheted scarf of almost the identical color as the blouse. We paid for everything and decided to have a bite to eat. It's so much fun being a girl!

During lunch we decided to go shoe shopping. I still can't understand why, I have such a fetish for shoes, especially open toe sandals with sky high heels. I love to look down and see my painted nails confined by the leather straps. I feel very vulnerable and want my mistress to seduce me and have her way with me. As, I think about it my mind turns to what must be going on between Kimberly and Stephanie. I wish I could be with them!

We found several shoe stores and tried on a loads of shoes and boots. Being winter, I thought I might like to have some additional protection from the weather and bought a pair of black leather boots. They had a 3 inch heel and came to just above my calf. The salesman was completely fooled, he thought he had two good looking ladies and even made a pass at Miss Li. She handled him like a pro and soon he was giving us a 25% discount! Li is so feminine, I still can't belive she's a guy!

After, Li noticed that it was already 4 pm and suggested we start back to the hotel. My feet were tired and I readily agreed. She paged the limo driver and within 10 minutes we were on our way back to the resort. Upon arrival, Miss Li said she had some matters to attend to and left me in the hotel lobby. I was so horny from being dressed all day, so, I went up to my room looking for Kimberly but found Stephanie there, alone.

She greeted me and pulled me close. She looked into my eyes and told me that tonight I was her property. Miss Kimberly would be spending the night with Miss Li and instructed me to remove my jacket, skirt and blouse. I eagerly responded and was soon down to my pretty purple lingerie.

She walked around me eyeing me as if I were a possession. She told me, "tonight things will get a little rougher than I am used to, since her sexual desires were somewhat more dominate than Kimberly's". She walked up to me and reached behind my back, grabbing a fist full of hair she pulled my head back. I squealed at her roughness and she told me to "shut up". She began to bite my neck, hard, I pulled back from her, but could not escape her grip on my hair. She reached under my thong and took my ridged cock in her hand, she had no problems telling me that "this is what I wanted" and "that parading around as girl, a sexy girl, would cost me dearly". I was so excited, I fantasized about this from my earliest days of crossdressing. Stephanie ordered me to my knees and opened her robe. Besides her stiletto mules, she was completely naked. "Kimberly says that tongue of yours is magic, eat me now girl" and with that she forced my face into sweet, trimmed bush.

I noticed her perfume, light, seductive and very feminine. My mouth and tongue soon found her labia, they were already wet and I was soon immersed in her sex. I knew I had gotten Mistress Stephanie attention, because her grip on my hair lessened. I parted her lips with my tongue and delved deeper. My lips were suckling her, my tongue began to explore the depths of her womanhood. I found her love button, her clitoris, it was erect and ready for action. OOH, how I wish I had one of those. I gently teased it with several light licks, I remember Kimberly telling me that she enjoyed to be teased before getting down to business. As I continued, I sucked her clitoris and heard a soft moan escape her lips. Standing on her heels, she began to hump my face. I knew I was pleasing her and took great satisfaction in her pleasure. Slowly, I began to increase my pressure on her clit, then, I inserted one, then two fingers into her vagina and felt the slight shudder of a vaginal orgasm. Her come flowed and I relished its taste. She moaned louder and forced my face into her pussy with strong gyrations of her hips. As I increased pressure with my tongue, I quickened the pace. She responded with a loud moan and demanded more. I pictured what this must look like. Down on my knees with my cock and balls hidden between my legs. I was a picture and Mistress was a tall, elegant and beautiful woman thoroughly lost in passion. I get myself so aroused with my desire, being submissive woman with my dominate mistress enjoying my talents. I'm so hard, I could come.

I continued to finger and lick her, then I got an stupid idea, I withdrew my hand from her pussy and found her ass. I was a little surprised when she whacked me on my head and screamed "do not go there" and I quickly withdrew my hand. Turning my full attention to her clitoris, she was soon grinding her hips faster and faster. When she came, her hands forced my face deep into her as she road the orgasm for all it was worth. Her juices flowed and I licked every drop until she released my head and push me away, out of breath, I fell to the floor.

When she regained her composure she was pissed, she told me "I was a whore dressed in lace and would now get the fucking I dearly deserved"! "How dear I try fuck her ass, that is for submissive fagots like you". I apologized and told her" I just got carried away". She seemed not to hear me and left the room, returning a few minutes later, she wearing the biggest strap on phallus I have ever seen! She order me to get my ass over to her and get back on my knees. I did so and she told me suck her dick, like the wicked girl that I am. I opened my mouth and with her hands grabbing the back of my head she thrust it into my mouth. As I pretended to suck her off she began pumping it in and out. I gagged and almost threw up, but, after several pumps began to get the hang of it. In a calm and deadly serious voice she told me that "I was going to be talented cocksucker" and pushed me away.

She instructed me to stand up and turn around and then leaned me over the arm of the sofa. She placed a glob of KY Jelly on my ass and with the skill of man mounted me from behind and began to fuck me. As my "pussy" accepted the phallus, I began to moan with pleasure! I love a good screwing. Rather quickly, she had the entire length deep inside me, and I loved every minute of it. After some time, suddenly, she pulled out and undid the straps, removing the dildo, she grabbed me by the hair she pulled me into the bedroom. Throwing me onto the bed she mounted my rock hard cock and kissed me. She thrust her tongue into my mouth and I began to suck it. As we kissed, her hand found my ass and began finger fucking me. I was ready to explode as we kissed and fucked. She whispered in my ear, as did Kimberly, give me your load, NOW, and on command, I came deep within her. My body shook with the ecstasy of orgasm and I collapsed on top of her.

Mistress allowed me a few minutes to catch my breath and then requested I clean my come out of her sweet pussy. Gladly, I raced to her sex and licked up every drop of semen, while I was there, she began to respond to my work and soon I brought her to another orgasm!

When we were composed, Mistress told me I was very talented and possessed one of the hardest cocks she has ever had the pleasure of. I was instructed to straighten the room, put away all my cloths, shower and come back to her. I did as instructed and returned to her, it was 6pm. On the bed I found a pink thong, my pink chemise, pink pumps with 5 inch heels and a very sheer pink robe. I dressed my self and waited for mistress to shower.

While she was in the shower the phone rang and it was Kimberly. She was very soft spoken and asked if I had a nice day? I told her of the events and she was concerned that Stephanie was to rough. I told her that it was OK, as I loved every minute of it. I was told to be a good girl and tomorrow we would drive out of town and spend the rest of our vacation together. I said good night and hung up the phone. By this time Mistress Stephanie was out of the shower and informed me that room service would be here soon and to let them in. When I began to protest about my dress, she said I looked fine and closed the bedroom door.

The delivery man laughed at me as he set up the dinner and remarked that I was pretty fucked up. I asked him to leave and refused him a tip! We ate dinner in the privacy of our room and watched a movie before bed. That night I dreamed of Kimberly and the prospect of living the rest of my life as a woman.

  

  

  

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