Excerpts From the Diary of a Sissy's Very Feminine Life

by Wendy

 

Early in our marraige my wife knew that I enjoyed playing with her hair and with mine. Occasionally I would walk in as she was rolling her hair and jokingly ask if I could help. Once she even let me roll a couple of sections of her lovely hair before she brushed me away, saying that hair rolling was for women not men. She did love to run her fingers thru my hair and tell me that some day she would like to do something with my long locks. I would blush and secretly wish that she would follow thru on her promises.

One Saturday afternoon she went out shopping and I decided to try my hand with her curlers and my hair. I was all thumbs and made a horrible mess of it. But the feeling I got standing in front of that mirror with all those rollers in my hair was exquisite. Naturally I didn't have any time for styling or for a dyrer set but just the thrill of rolling my one hair on her curlers made me forget about time and her return.

I was standing in front of the bathroom mirror when a movement off to the side in the mirror froze me in place. Briefly I glimsed my wife standing at the door to the bathroom. As soon as I saw her she was gone. I was mortified. I quickly yanked the rollers out of my hair with some loss of strands. I did not care. I was totally humiliated.

When I came out of the bathroom, my wife was reading a magazine and she smiled at me and asked what would I like for dinner. She did not say a word. Neither did I.

Several days passed with no mention of the incident. On Wednesday evening she suggested that we go out for dinner to a little Italian restaurant we both enjoyed.

The meal was great and we laughed and talked and ate with great gusto. Just as dessert was being served she picked up her purse and took out her compact and lipstick. I always enjoyed watching her do her lips. She was so precise and sensual in her movements.

She finished her application but did not put the lipstick and compact away at once.

She smiled at me with her carmined lips. "Dear, you went behind my back and used my rollers without asking me. All you had to do was ask. I would love to see you in rollers. It would be a hoot. But you didn't care if I approved or not. Well, dear, for that uncaring action you must be punished. I will gladly help you with your little fetish. As a matter of fact I am going to help you starting right now.

I am going to leave the restaurant right now go next store to the Princess Salon. I am sure you saw it on the way in. I want you to follow me in about ten minutes. That will give you time to pay the bill. But before you pay the bill I have something that you must do."

She gently pushed the comapct and lipstick across the table to within an inch of my hand.

"After I get up and leave, you are to pick up the compact and open it. Then you are to pick up the lipstick and open it to it's fullest extent. Then, sitting here at the table, you are to do your lips just like I did mine. I know you were looking so I know you know how. You will love the feel and the smell and the taste. Do a very good job or you will really dislike what might happen to you. At the Princess Salon they are waiting for you with some very special treatments that involve heat and rollers and dryers and cosmetics. They have a rule that no one can enter the salon without prefectly made up lips. Don't make me any madder than I am now, dear. How long you spend at the salon depends on how good a job you do sitting here in the restaurant with a lipstick in your hand."

She got up from the table, patted me on the head, and walked elegantly out of the room.

I stared after her and then turned slowly to the instruments laying on the table. My hands were trembling as a took the compact from the table and flipped it open. Staring back from the mirror was a face of cringing humiliation. I placed the open compact on the table and picked up the lipstick. The color labeled on the end of the tube was "Miss Scarlet". I shakingly pulled the tube apart and slowly rolled the lipstick out till it stopped coming. It was an almost new tube. I noticed a couple of women at the next table trying not to stare at me.

There was no time to think. I had to get this over with. The tube came up to my quivering lips and my left hand brought the compact mirror to my eyes. I did know what to do. I had never done it in public before but I did do a reasonably good job. The waiter brought the check with a slight smile. I dropped money on the bill without really counting it. As I stood up from the table I felt as if all eyes in the restaurant were on me. The fifty feet across that room to the door were the longest mile I had ever walked.

As I opened the door and stepped outside my legs came close to failing me. I glanced to the right and saw a red enamel door with a curlique "P" in gold leaf emblazoned on it. What would happen when I opened that door? My wife knew. That was why she was smiling as she left the restaurant. As I walked those few steps my eye caught my reflection in the glass fron of the restaurant. The man in the reflection had brilliantly painted scarlett lips and was opening the door to a woman's beauty salon.

 

I feel very much different now. I am not sure if that is good or bad. I am feeling things I had never felt before.

Last night my wife told me that we had a special visit to make today and that I would be required to be at my feminine best. So she set my hair very carefully on medium rollers, secured a silk wrap around my head and sent me to bed.

In the morning she assured herself that I had donned a matching bra and pantie set and selected for me a sleeveless day dress that was figure flattering and somewhat girlish. After helping me with normal day make up she finally took the rollers from my hair and brushed and primped and sprayed my hair into a shockingly cute 50"s sox hop do.

White open toed 2" slingback sandals completed the outfit.

I was ready for something.

As we drove from our neighborhood, I checked my make up in the passenger mirror. I had the feeling that I would want to really look girlish for this trip.

My wife suddeningly made a right hand turn into a parking lot. I glanced out the window and froze. The sign, very discreet and professional, next to the door in front of us said: Dr. Sandy Rodgers, OB/GYN.

My wife had come around the car and was opening my door. I ducked my head carefully to avoid and damage to the confection on my head. She took my hand as she would to a 12 year old girl and guided me into the office. There were three women sitting in chairs about the room and one receptionist behind a sliding glass window. My wife kept ahold of my hand and we went to the window. Thankfully my wife handled all the forms and questions. One question was: Reason for visit? She wrote: Wendy's first gynecological exam.

As we took our seats the other women in the room showed some curiousity in their eyes but nothing was said. After the first few secretive glances the women went back to their magazines with strange smiles on their lips. I was trembling.

At last the nurse called out: Wendy. My wife took my hand and helped me up. My knees were not working too well for some reason. As we passed into the examining area I thought I heard a few giggles behind me.

We were shown into a small changing room and I was told to strip down to bra and panties. Later I found out this was not the usual procedure. I was to keep my bra and panties on to enhance my humiliation. My wife helped me into a short white rayon hospital gown.

The nurse came back for us and led us to a room marked "Mammography".

I hesitated at the door but my wife was firm but kind. The nurse said: Take your bra off please. And I did. I was led to a machine that I had never seen before. The nurse got my chest to do things I had never done before. The experience was cold and frightening and oddly fullfilling.

I was told to put my bra back on and then we were led to another room.

As the door opened I stopped short. There were bright lights aimed at a weird looking table in the center of the room. It seemed to be a ¾ table with strange attachments on one end. It looked like a broken recliner. I was told to take off my gown and panties but to leave my bra on and to sit on this chair.

Dr. Sandy Rodgers was an old high school buddy of my wife's. That were and are great friends. She would be anything for my wife. And she did.

She was very professional and really very kind. But she did what had to be done no matter what pain and humiliation was put upon me.

I learned several things this afternoon.

How to palpate my breasts to check for lumps.

What size tampons I would need soon.

How cold stainless steel can be.

And where stainless steel can go.

And what a woman goes thru in everyday life.

And how high above my head my ankles can be raised.

I love it!!!!

It's been nine months since my last visit to Dr. Rodgers. When my wife told me this morning that it was time for another visit I got goosebumps around my nipples. The black satin cups effectively contained the throbbing pair of natural sissy breasts. I remembered the last time, and it was the first time, that I had gone to see Dr. Rodgers. It was not a pleasant experience. But it was a learning experience.

I was told to put on a soft pink cashmere sweater over my black bra and to step into a grey pleated flannel skirt. My hair was soft and natural, tied into a high ponytail by a pink ribbon, with just a 1 ½ inch bang across my forehead. Just mascara and blush and a shiny pink lipstick were all the cosmetics I was to be allowed for this trip.

My wife and I drove silently across town. At each stoplight I was to do my required sissy duties. I had to whip out my compact and lipstick and extravantly redo my lips at each stop. My wife tried to be sure there was another car right next to us each time.

The office was as crowded as before. When we approached the receptionist, my wife told her quite loudly that JIM (not Wendy as she had done before) was here for HIS checkup. My face deepened even past the shade of the cosmetic blush.

We sat in the waiting room for about a half an hour. The women all around glanced and smiled and giggled for the whole time. Finally the nurse stuck her head thru the door and called out "JIM, please come back for your mammogram". My wife patted my hand and helped me up on shaky legs and heels. I walked past all those women with my eyes straight ahead to the door to my further humiliation.

The nurse took me to the same mammography machine and told me to take off my sweater and bra but to keep the skirt on. In the last nine months my breasts have come along nicely for a sissy. I could almost fill a padded underwire B-cup. So there was not as much need for strange gyrations to achieve the critical mass for the machine to record the state of my breasts. I was shivering and was most grateful when the nurse told me to put my bra back on but to leave the sweater off for the time being. I was led to the examining room and told to take my skirt off but leave the bra on and to get into position in the examing couch with my feet up in the stirrups. My bra jutted out and my ponytail was perky on my head but I dreaded this position.

Dr. Rodgers came in with my wife and said nothing to me at all. She talked with my wife about old school friends and restaurants while I lay there totally exposed. Finally she looked my way. "I am going to loosen your bra, please don't make a sound. I want to feel your breasts."

"I think your husband is about ready for the implants. Maybe in two or three months. The pills have worked wonderfully. Are you sure you want him to go all the way to D cups?"

"That's wonderful news" my wife chirped."Yes, it will be D cups for him. I want his bra to feel the strain."

The Doctor looked down at me again. She ran her hands gently down my legs and rested her hand where I should have a vagina. I felt an even greater shiver go through me.

"I think that in three months HE will be worthy of that ponytail."

With tears streaking my mascara, my wife helped me through the waiting room and to the receptionist's desk. She said very loudly for all to hear.

"Please make an appointment the first week in August for JIM's surgery. then make a monthy appointment the first tuesday of the month thereafter for JIM, no maybe you had better make that appointment for WENDY."

 

Late Wednesday evening, my wife, Mary, was overseeing my preparations for bed. The curlers were in and she was rigorously tightening my pink satin sleep corset. Nothing out of the usual. Then she hit me with a bombshell.

"Tomorrow morning when you awake, I'll have already left for my day of meetings. You shall be on your own the whole day. I think it is time you had some real experiences in the life of a woman. Now I know we had talked about what would be nice for you to wear tomorrow. I still want you to wear those clothes. But this time you will not just be prancing around the house. I want you to get dressed then you have the whole day to accomplish these three tasks. You are to find a beauty salon that we have never been to and get yourself a roller set and a brand new hairdo. Secondly you are to go to a nice restaurant and have lunch. That's not too hard. Thirdly you are to search out, try on, and purchase a beautiful cocktail dress to wear to my birthday party next week."

My eyes must have glazed over. She looked at me strangely.

"Are you all right?"

"Yes, Mame. You just startled me. I have never been out of the house by myself. It is scary to think of it."

"Oh, you silly girl! Of course it is scary. That is the idea. Now if at anytime during the day someone asks you your name, you are to tell them the truth. You are Jim. You haven't yet earned the name, Wendy.

Maybe after this day's experiences, I might think about allowing you that honor. Now I will leave the Miata for you. That will be nice, won't it?"

She dropped the nighty over my head and patted me on the bottom.

"Sleep tight, Jim"

I didn't. When at last I must have dozed off, it was all the more surreal to awake and come quickly to the idea that I was to go out into the world as a woman for the whole day and do womanly things by myself.

She was gone when I slipped out of the training room. I was on my own. But I had to do what she had instructed. I stayed in the corset and nighty and had a light breakfast. Then off with the night things and into the shower. I was apprehensive but, hard to believe, really quite calm. I finished my morning duties and dressed somewhat quickly but still carefully.

My underthings were simple but elegant. Black silk panties with a black rose applique on the crotch. A white satin corselette to control the waist and perk up my tits into the underwire cups. Nude hose fastened to the garter hooks of the corselette. I stepped into a pair white pumps with two inch heels. Before I donned the dress I looked at myself closely in the full length mirror. YES, I could do this!

I sat at the makeup table and tried to remember all that Mary had taught me. It was morning so I should not be too wild. After all I had to have my hair done. At the salon, I would have them do my makeup for a "lady who lunches". Now just simple foundation, blush, a light eyeshadow, and coral lipstick.

I looked at my hair in the mirror. Yes, I could use a new hairdo. For now I just brushed it back vigorously for about three minutes and then brushed a section in a sweep across my forehead and pulled the rest gently behind my ears and fastened the hair with a barette on eash side. A quick shot of hairspray on the sweep across my forehead and I was ready(?) to face this strange and wonderful day.

I stepped into the yellow linen sundress with the offset straps that Mary had chosen last night for me to wear. I brought the material up to my breasts and slipped my arms through the straps. I always have a hard time working a back zipper and this time was no exception. Finally the zipper was totally closed and the dress molded to my form.

The bodice and the the upper body above the waist was snug and precisely fitted. At the waist the dress flaired into a full generous A-line skirt which just kissed my knees. I walked to the mirror and swilrled three times. The skirt danced and the top stayed firm. Not bad for "one of the guys".

I picked up the white straw purse Mary had selected and checked to be sure I had all that I needed for the adventure. The cosmetics were all there. I made a careful adjustment with my lipstick and dropped it into the purse. Then I had a thought. I went to Mary's vanity and picked up a gold Tiffany pocket lighter and searched in her drawers for a pack of Misty 120"s that she sometimes smoked during sex. I do not smoke as Jim but for some reason I had the feeling that

"Wendy" may want to have a cigarette at lunch. The pack and the lighter went into the purse. At the last minute I remembered that I had no jewelry on. Two inch silver hoop earrings and three heavy silver bracelets and Mary's silver mini Rolex solved that problem.

I took one more glance into the mirror, smiled at what I saw, and stepped into the garage

The light green Miata sat there with the top down. I opened the door and slid into the driver's seat, being careful not to muss my dress. I had never driven as a woman. This might be a little scary. I adjusted the mirrors and pushed the button to raise the door. I took a deep breath and turned the key.

The door closed down on the garage, and I sat there a moment, somewhat lost because I just realized that I didn't know where I was going. All dolled up and nowhere to go.

Then it came to me. There was a salon that I had noticed right inside the south doors to the mall. Whenever I walked into the mall that way, I was intrigued by this small shop which seemed very elegant, very pricey and very exclusive. That is where I would go to start my first day as a woman by herself.

I pulled the Miata out into the street and made my way carefully to the expressway. With the top down, the feel of the wind rushing over my almost maked shoulders and whipping thru my hair (the hairspray didn't do much good) was exquisite. I had never driven with heels before and that difference and my anxiety at the prospect of possibly being stopped by a traffic cop made me super careful.

I was at the mall entrance within ten minutes. I grabbed my purse and started to step out of the car when it hit me that I had always been in the company of my wife whenever I had ventured out in public as Wendy. There was a certain security involved with having a real woman as your guide and mentor and maybe even, as your humiliator.

Here, now, I was alone. To all to see, I was 90% a woman. Ten percent is sometimes easy to see.

I took a deep breath and smiled as my sundress bosom swelled with feminine pride. I can do this, I told myself, I can. I have to. Mary told me to.

I patted my hair into place as much as possible and fixed (not really neccessary) my lips. I swung out of the car and swinging my purse I strode on my two inch heels for the door.

The mall was not busy this early in the morning. The salon was the second slot to the right inside the mall entrance. It was a regular store front space but the windows were shielded by lush burgundy drapes and the door was a solid burnished mahogany. There was a discreet brass plate next to the door which said in gold inlaid lettering: "Sybil's - HairStyles for Women". That was all.

I sucked in my corsetted frame and pulled the door open.

The inside of the salon was beautiful. Only the best and most expensive woods and steels and fabrics were used. It was truly a woman's domain. Elegant but soft, substantial but feminine.

A startingly handsome young woman was standing behind the receptionists desk wearing a pink Chanel suit with dark purple piping.

I saw no one else but I did hear a dryer softly working in the next room.

"Good morning, Miss, may I help you?" said the receptionist.

I took a deep breath.

"Yes, thank you, I was wondering if you could do a cut,set and styling for me. And possibly a makeup application also"

"My dear, you are totally in luck. Sybil, herself has had a cancelation this morning and is free. We will be happy to do whatever you ask. Now what name shall I put down to tell Sybil?"

I hestitated. I had to say the right thing. Mary told me that If anyone asked my name I had to tell them.

"My name is Jim."

She looked at me. Really looked at me.

"Oh, I see."

"I hope there is no problem?"

"Oh, no, I don't foresee any problems. i was just taken aback a little. Let me tell Sybil that a special customer has come in to enliven her morning."

She smiled and left me and went into the room behind the door.

As I was standing there the front door opened and a nicely dressed young mother came in with her young daughter, who must have been 11 or 12. They saw me and smiled. I smiled back and said good morning. It was nice to see a mother taking her daughter to such a nice salon at that age. I wished my mother had done that for me.

At that point the receptionist came back thru the door and said hello to Brenda and young Nancy. then she said to me: "Come on back, Jim, Sybil is anxious to meet you." There was a small look of curiosity on Brenda's face. Nancy was just dreaming about what was to be done to her. So was I.

I followed the receptionist thru the door and like Alice in the Rabbit Hole, I was in another world. I had been to Mary's salon many times and had work done to me there but this place was a different planet. There were no posters of movie stars or ads for shampoo. No loud, raucus music. No teased and pink smocked worker bees. Everything in this room said: I will make you beautiful. That is the only reason I am here.

There were four fantastically luxurious styling stations and a separate room with five fabulous 1950's stainless steel torpedo style driers set behind velvet clothed easy chairs. There was a makeup area with more tubes and wands and bottles than Bloomingdales. There was a area for manicures and pedicures with the most elaborate pedicure thrones I have ever seen. I said to myself right then that I was going to have a manicure here today also.

Sybil had her own room at the back of this palace. Three sides were down in crushed velvet of the deepest red and the fourth wall, behind the stying chair, was all mirror. Sybil stood behind the chair looking like a Viking Goddess. I was amazed that she spoke. I would have believed her a beautiful painted statue.

"Welocme, Jim. It is not often that I have the pleasure of doing someone as special as you."

"Thank you, Sybil, I hope I am not asking something which is out of place or against your feelings."

"Oh, No, my dear boy, far from it. I like to DO my husband a couple of times a year but you are the first young man who has actually walked into my salon asking for my services."

"Please, sit down and tell me what you want."

I sat in the styling chair and she listened and asked questions as one woman to another. We seemed to be on the same wave length. I was thinking about 50's glamour and perkiness and she knew just what I was after. She decided that my hair at 8 to 9 inches was just a trifle to long for what she had in mind. So I told her to do what she thought best. I would sit back and relax and place my future womanly aspect into her hands.

Immediatley she placed a deep burgundy frilled smock over my sundress and laid me carefully back into the shampooing sink. Hers hands were marvels of strength and gentleness. As she was created the billows of foam she called to someone named Jo and asked her to be ready to do a manicure.

When she had finished my wash, she wrapped my head in a fluffy white towel. I sat back in the styling chair and she said that she had to do something for about five minutes and that Jo woould start my maincure. I was happy for anything she said. Jo started right in on my right hand as I sat there in feminine splendor in my frilly smock and fluffy towel.

Sybil came back and ruffled the towel all over my head to get the excess water. She checked Jo's progress and wispered a color name in her ear. Magically, scissors appeared in her hands and gracefully circled my head, snipping her and there, and removing a good bit of what took me so long to grow. Or at least it seemed that way to me.

Quickly the cutting was done and she misted my hair with a concoction which she said would install a lovely firmness to the set. By this time Jo had reached to a shelf and retrieved a bottle of nail polish that sparkled in its' brilliance. It seemed to be a golden tinted, bronze based, burgundy color. As the first stroke of color flowed onto my little finger a cold chill raced through my body.

At the same time, Sybil, forcefully took a lock of my hair and wound it ever so tight on a medium brush roller. I closed my eyes and let this erotic scenario play out. I was in heaven.

The rolling didn't last near as long as I would have wished But now I was to be installed under one of those terrifing dryers. Sybil placed me just so and raised the dryer to a level she liked. She smiled and patted my hand and inspected the newly lacquered nails. then she handed me a magazine and told me to look thru it and see if I found any hairdo's I might like. Then she patted my shoulder thru the smock and turned the machine on what was probably it's highest setting. I have never heard such a sound in my ears. It was lovely.

At first I closed my eyes and luxouriated in the intense feeling I was having. Then I remembered the magazine and looked at it. It was a Vogue magazine, dated May, 1956. And there was much in there that appealed to me. Oh, my God, was there.

As the machine whirred about me and baked me pleasureably, I at last found the picture that said this is the hairdo for Jim, No this is the hairdo for Wendy.

After 50 minutes of heaven, Sybil brought me back to earth and took the magazine from me and carefully noted the picture I had held pleadingly up to her. She looked at the picture and smiled.

"I think we are on the same page here, Jim. That would have been my choice too."

"Let's leave you hair up in the rollers for a little while longer and I will do your make up personally. I believe you are going to lunch, you said? Well, I am expert at doing the "Ladies Who Lunch". No one will ever know that you are not quite one of those "Ladies", at least not yet."

Gently Sybil removed my attempts at femininty and then made sure that I was feminine with her skill. The tubes flew and the jars emptied and I was enthralled at her skill. Cosmetcis were applied, whose use and names I had never heard of, but which made this Jim into a Wendy.

Every square centimeter of my face and even other parts of my body was brushed or had a tube slide over it. The finishing touch, at least for me, was the application of the lipstick. The lipstick matched my nails perfectly and the combination against the bright yellow of my sundress was stunning. Sybil handed me the tube and told me to face the mirror. Then she told me to raise the tube to my lips. My lips didn't need anymore but I needed that thrill of seeing my hands bring that lipstick to my lips. I was shivering.

"Put that lipstick in your purse, dear. you are going to need it after your lunch."

"Now let's make that picture come to life."

Combs and brushes and sprays danced all around my head. The rollers had vanished and something materialized which mesmerized me and made Sybil beam and the rest of the staff applaud.

Sybil tapped me on the shoulder and I stood and took the smock off.

I took a step and my hairdo bounced as I walked. I turned my head and my hairdo turned but then swung back on it's own. Oh so cute and perky and feminine.

How could I ever thank Sybil and Jo? I was ready for the rest of the day and maybe to actually be "Wendy".

My experience at Sybil's had been so pleasing and self assuring that I was taken by surprise at how crowded the mall had become while I was enjoying Sybil's. The crowds made me nervous once again. I was still a fish, although a nicely coiffed and madeup fish, somewwhat out of water.

My dress and makeup and hair were luckily a good fit with this upscale crowd. Now if I could just avoid tripping on my heels and falling on my less than feminine butt, I would be very, very happy.

Nobody took special note of me as I carefully slipped out of Sybil's.

I squared my shoulders and took a deep breath and started walking to the other side of the mall where I knew there to be a rather nice French restaurant with a patio which overlooked a pond. That would be my next stop on Mary's list to be accomplished.

Within five steps I knew that the picture in Vogue was a Godsend. O could feel my "Do" bouncing on my head and swinging seductively as I turned my head. I glanced into a passing window and saw my reflection. Those 50's women knew what really mattered. Pointy tits and perky hair.

As I walked slowly to the restaurant, I looked into many shop windows. It was tremendously satisfying to be able to look at a display of bras and not be selfconscious of being a male staring at female underwear. I was a woman shopping for underwear and should be looking intently at those displays. I was one of the elect.

When I arrived at the restaurant, I was pleasantly surprised to find it not as yet crowded. There were only two couples waiting for a table. I approached the Maitre 'D and asked for a table for one on the patio.

"Of course, Miss. It will only be a few minutes. May I have your name and I will call you."

His request surprised me and I stammered, "ah, Jim".

He looked at me sharply and with a voice that said he had seen everything said: "But of course, Jim".

In the next few minutes the other couples were seated and several new people joined the wait.

At last he came to the podium and called out: "Jim, Party of one, this way please." Several people looked confused when a woman answered his call for Jim.

I was seated at a lovely table, right by the rail above the pond. I was glad to be off my heels and sighed as I placed my purse on the table just as a waiter came up behind.

"Would Miss like a small cocktail before lunch?"

Yes Miss would. Miss would like a Pink Lady.

I fussed in my purse and brought out my compact and opened it and raised the mirror to my face. I looked pretty damn good. Sybil was a wizard. I snapped the compact shut and slid it into my purse and then remembered the lighter and cigarettes. The impulse was too strong to ignore. I took the pack of Misty Menthol 120's and shook a cigarette out and placed it between my fingers of my left hand. The nail polish was perfect and it looked like the cigarette was part of me. I had never had more than a few puffs in my male life. I raised the cigarette to my lipsticked lips and reached for the lighter. but before I could pick it up, the Maitre 'D had come up along side of me and plucked it off the table first and ignited the flame and touched it to the end of my cigarette. I was startled but recovered and drew in the smoke and released it through my painted lips. The Maitre 'D smiled and set the lighter down carefully and bowed deeply from the waist and went back to his station.

I took a few more puffs to get the feel of a woman enjoying a cigarette. I even carefully practised different ways to femininally hold a long woman's cigarette. I found that I liked the physical action of holding the cigarette in a womanly manner.

The waiter brought me my drink and took my order for a small spinach salad. I also liked the female action of sipping a pretty drink while holding a cigarette in the same hand.

While I was thinking these thoughts, the Maitre 'D approached the table once again. he had a young woman of about 26 02 27 with him. She was naturally beautiful.

"Miss, we have filled up so fast today that there is a very bad shortage of seating space. I was wondering if you would be so kind as to share your table with this young lady? I am sure she would be an excellent companion for lunch. You know, Ladies Who Lunch".

I couldn't say no. That would have been unforgiveably rude for a lady such as I.

"But, of course, Please join me"

The woman sat across from me and the Maitre'd was almost laughing as he returned to his station.

The young woman smiled at me.

"Thank you so much for sharing your table. I know it is an imposition

but the Maitre 'D seemed to think that it would be no problem."

"Oh.no problem at all"

"Well, my name is Susan, what's yours?"

Here we go again.

"Susan, my name is Jim"

"Really, that is a most unusual name for a woman"

"Susan, I am a woman in training. Maybe someday I will be a woman but right now I am trying my best to be one."

"Wow, I don't believe you. You are dressed and madeup and your hair is so feminine. I would have never guessed"

"If you would like to find another table."

"My goodness, no. This is fascinating. I want to hear all about you and your, ah, training." "Where did you get that wonderful hairdo?"

"Well, I would love to tell you. Would you like a cigarette?"

 

My wife and I are home now. What an experience! My wife had been invited to a Mary Kay Sales Party on Sunday afternoon. Thinking quickly as usual, she offered me as the product display model.After showering and shampooing in the morning she set my hair on large plastic rollers and let it air dry all morning. I loved the feel of walking around the house, occasionaly sneaking a look in one of the mirrors at the cute miss with her hair all up in rollers. After installing me in one of my new bras and in a long panty girdle, she had me step into a long cotton peasant skirt, beige background with soft pink roses. Then came a scoop neck silk "T",white, with delicate ruffles at the sleeveless armholes and a pink satin ribbon accent around the neckline. White patent 1" opera slippers completed the outfit. Since I had no slip on my bra and figure were plain to see to certain lights. With my crown of rollers I made a wonderful sight. My wife sat me down at the vanity and removed the rollers. The mass of elegant curls cascaded over my shoulders. This did not last long for she then brushed the curls back over my ears and fastened them with a barrette on each side. She handed me a lipstick, very light pink, and said that that was all I needed to get to the party.

Besides my wife and I and the Mary Kay Rep. there were 10 other women at the party. I was treated as a model, not as a man or as a sissy. 12 women tried 15 different shades of lipstick on me and countless shadows and blushes. My hairdo was exactly right as a frame for the make up. What a lovely learning experience, to be treated as a woman, one of them. I love it!

 

Sometimes being a sissy can be a large pain. At other times it can be a true joy. My wife told me this morning that she has accepted an invitation from her sister to a costume party tomorrow night. She has known about this party for a long time. I have not. We will be going dressed as Tracy and Hepburn. She will be Tracy.

We had an early morning appointment at the local Bridal and Prom shop to find me a suitably sophisticated garment for the party.

I was allowed no make up, no fem attire for our trip to this shop. I wore a white dress shirt with a stripe tie and grey slacks. My hair, freshly curled from the ribbons last night, was pulled tightly straight back and rolled into a severe bun at the back of my head. Two tortise shell combs held the bun in painful place. Delicate cameo earrings, ivory sculpted ladies on a soft rose background, were affixed to my ears. My eye lids screamed for a smoky shadow and my lips begged for a soft rose tint. Not allowed. Today I was to be a sissy, not a fem.

The women at the shop were surprised and playful when they learned our mission. Soon the tie was discarded and serious fittings took place. My wife loves tightness and restriction in the bosom area. That is she loves it on me. Right then I was a man in a bun in a dress. Tomorrow I will be a little less than a woman but a happy sissy in a gown and a beautiful coiffure. I love it!!!.

 

It is difficult to type on my keypad. My hands have been encased by my wife in white cotton gloves over the finest aloe hand cream. She has taken down my pageboy and has thrilled me with curls tied up in thirty-five pink satin ribbons. That seems to be the theme tonight. My bed has been fitted with pink satin sheets and also the pillows have pink satin pillowcases. The better to kept my hair at its best. I have been allowed to wear my wife's finest night gown. The fitted and tight lace and satin strapless bodice constrains my chest and narrows my stomach down to the flaired satin full pleated skirt. Of course the gown is light pink with embroidered pearls on the cups of the bodice. I don't know how I will stay on the bed. I am sure I will slide right off. Maybe my wife will tie a few of my hair ribbons to the bedposts. That may be a nice idea. My instructions are to freshen my pink lipstick and think about my future. The lipstick is the exact shade as my hair ribbons. I think my future will be very pink. I love it!!!

 

My wife has tied my hair into a high ponytail with a light yellow scrunchie. She suggested that I wear a light weight white cotton man-styled blouse over my khaki plain front slacks.Brown penny loafers completed the outfit. On the trip to the boutique my hair blows in the wind thru the convertible. Not a bad feeling for a guy.

My wife has made an appointment at the boutique for me. I have not been to this boutique before and am a little concerned. I should not have been. My wife loves me and she know what is best for me. The women at the boutique are so kind to me and treat me with the highest respect. As I stand on the low platform in front of the three sided mirror with only a pair of silk panties on I feel at ease. My hair has been taken out of the ponytail and brushed to the height of silkiness over my exposed shoulders. I stare into the mirror as my wife brings another article into the room. The fitting has taken longer than I had expected but I have enjoyed the process. My wife wants only the best quality and fit for her husband. She slips the straps over my arms and I bend slightly at the waist to allow the straps to rest on my shoulders and the cups to fill with what I have to offer. Tenderly, my wife tugs ever so gently behind my back and I feel the hook and eyes slid shut. I shake my head ever so slightly and my hair swings senuously across my neck. My chest juts out with pride and joy. Everyday something new. I love it!!!

 

 

My wife is sitting under the dryer next to mine. Every so often she puts down her Cosmo and looks in my direction and smiles. Her head is rolled in the same tight pattern as mine. We will have roughly the same "do" when the stylist finishes and sends us on our way. Short bangs, longer sides neatly rolled under to create a pageboy roll under the ears and in the back, the crown brushed back from the bangs with a slight pouf (just a little more pronounced on my wife) at the top.

It is a wonderful feeling to sit with my laptop open on my knees and to feel the rush of the hot air through my rollers. My wife insisted on a fresh manicure for my nails before my hair was set. The sight of my lacquered pink nails gliding over the keyboard as I write this message gives me a confidence I didn't have one hour ago.

My wife told me this morning that I was to accompany her to the beauty shop this morning and that she had a surprise for me. She certainly did. I have loved every minute of it. Before we were put under the dryers, she told me that I would have to have a make up session after the hair styling was done. She didn't want to walk home with a sissy looking man. She wants to walk home with perfectly coiffed and feminized husband.

If this is what it takes to satisfy her, I am her man.

I think my earings will nicely show under the "Do" and I hope my lipstick matches my nails. I love it!!!

 

The weather has become much warmer these past few weeks. I had a delightful weekend. I love the smell of fresh cut grass. Friday evening I cut the yard, front and back. Saturday morning, my wife washed and rolled my hair and I was able to sit in the back yard and let the sun dry my hair. She had me wear my little yellow strapless sundress. I love the feel of the sun beating down on my shoulders and the thought of the adorable tan line across the top of my chest.

After about two hours of reading and dreaming, my wife tested my curls and decided that I was dry. She took the rollers out right in the back yard and allowed the curls to fall on my bare shoulders. With just a few minutes of brushing and styling, I had a beautiful, full, sleek, pageboy framing my sun kissed face. My wife handed me the hand mirror and my sundress bosom swelled with pride as I accepted the crimson lipstick from her hand. With a flick of my head, I tossed the points of the crisp pageboy away from my mouth and smoothly and slowly applied the lipstick. The feel and the taste were intoxicating. I applied two coats. My wife came up behind me and placed her hands on my hot shoulders. She nestled her mouth into my hairdo and said:"Slip into your heels and lets go shopping".

I love the spring.

 

Great sales at all the shops, so my wife and I went shopping yesterday for both of us. This morning my wife laid out an outfit for me which I found as I came out of the shower. There was a note laying on the clothes saying that I should not dry my hair.

Things sounded very good.

I slipped into the bra(38B which is just right for me) and panties and then put on the black sheer thigh hi's and stepped into the 2 inch black file pumps. I lowered the simple black stretch jersey sheath over my head and it molded to my body.The dress came ankle length with a sexy knee high slit on the left side. The bra did wonders under the clingy sheath. There was a shiny thin silver link chain bracelet and a long strand of white pearls which I could double around my neck so that one strand was a chokker and the other hung down between my breasts.

Simple and very elegant.

I clipped on silver hoop earrings and did a light makeup of mascara and blusher and shiny deep pink lipstick. I took one swirl in front of the mirror and called out to my wife that she should come into the bedroom.

She came carrying the roller case and pushing the stand dryer. My hair had dried a little while I was primping but she had a spray bottle and setting lotion ready to go. My wife showed me a picture of Doris Day from the early sixties. Really something to look forward to. I think I will be here under the dryer for about forty five minutes. She is shaking a bottle of pink nail polish in front of my eyes as I type this. I think she wants me to finish typing and sit quietly under the dryer so she can finish with me.

I think this is going to be a delightful day.

  

  

  

*********************************************
© 2007 by Wendy. 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.