I had recently moved in with my Mother-In-Law (she is 70 and I am 50) due to financial pressures and, the wife had taken a job in another State. We got along very well, I would help her around the house, with cooking and cleaning. She thought it would be fun to teach me to sew and the lessons were going well.
My background, for as long as I can remember I was in touch with my feminine side. There was an old photo of me about age 2 wearing one of my Mom's petticoats with powder on my face. I had gotten into her things. I can remember playing house with the neighborhood girls, we would take turns playing mommy, daddy or, little sister. Which meant I got to dress for mommy role or sister role often as I would volunteer.
Back to the present.
One day it was cold and snowy, I had been out shoveling off the walk and came in cold and wet. My Mother-In-Law advised me to get out of the wet clothes and take a hot shower. I took a shower and when getting out she was standing outside the closed bathroom door telling me supper was ready. I said I needed some dry clothes, she said just put on my robe hanging on the hook. There was a large fluffy pink robe with little off yellow flowers embroidered on it on the hook. I put it on, came out of the bathroom and headed to the kitchen. She remarked that my barefeet might get cold, left the kitchen and returned with a pair of fluffy pink house slippers. I was in heaven.
After supper we were sitting around the fire when she remarked some hot chocolate would be nice. I said I would fix it. I returned with the chocolate and sat down and started working on a crochet scarf I was making. She was doing some embroidery work. I offhandedly, without thinking, remarked look at us a couple of old maids. She looked up and smiled and said well if you are an old maid you need to work on yourself. I grinned back and asked how so. She said you haven't shaved those legs and you need a pedicure. I wasn't sure how to respond to that and just blankly stared at her. She said well scoot back in the shower, you can use my razor. This was now getting interesting and, I wasn't quite sure if she was serious. She then said what are you waiting for, get going.
I got back in the shower, found her shaving gel and razor and shaved myself smooth. It was a wonderful feeling. I got off and toweled off. I could here her moving around in her bedroom as she had her own separate bathroom. She called from outside the door, told me there was some body spritz on the counter and I should use it. I spritzed myself all over when the door partially opened. She put her hand in and was holding a pink knee length silk nightgown with matching panties. She said you need these too. I couldn't believed this was really happening. I didn't said a word not wanting to spoil the moment and in fear she would stop. I put the panties and night gown on then the robe and fluffy slippers and stepped out.
She looked at me and said not bad, come sit at my vanity. I walked over and sat down. She proceeded to put a wig on my head, then said let's fix those eyebrows. She plucked happily away at my eyebrows with me wincing. She then scrubbed my face and put on a light coat of makeup. She stepped back to look at her work and said almost there, don't move. She left the room and returned with a needle and some ice. She put the ice on my earlobe for a bit, then jabbed the lobe with the needle and pushed in an earring, then followed suit with the other ear. She sat in a chair next to me, took my hands and applied fake nails and red nail polish. She than lifted a foot up and painted my toenails the same red.
After the nails dried we returned to the living room, sat down by the fire where she started working on her embroidery. She looked up and said I am so happy to have another old maid with me rather than a man. I had tears in my eyes, she said oh dear you are happy too. I was. Later, we headed off for our separate bedrooms, I fell asleep content in my nightie and panties.
I woke up the next morning, got up to dress and realized my clothes were gone. I went to the kitchen, she gave me a peck on the cheek and said good morning Clara. I looked at her confused, she said her best friend in school was named Clara and since we were best friends thought that fit me. I asked her about my clothes, she said my dear two old maids live here now. You can borrow something of mine till we shop for you.
We finished breakfast and she led me to her room, sat me down at the vanity and applied my makeup. She went to her closet and picked out a gray below the knee skirt, a pink blouse with lace at the neck and wrists, and a pair of black two inch heel pumps. She went to her dresser pulled out a girdle with garter straps, a black lace padded bra, black lace panties and, black hose. She said put these on, I stood there waiting for her to leave or turn around. Sensing my modesty, she said don't worry this is just us girls. I took the robe and night gown off, then blushingly pulled off the panties. I slipped into the new panties and tucked myself back. She laughed at that, said wait a minute and returned with a Kotex pad. She showed me how to put it in the panties, then I readjusted everything. I finished with the undergarments and my mind was numb and giddy, it all felt so good and right. She handed me two breast forms for the bra to complete the 36c look. Next came the blouse, skirt and shoes.
I felt so good, she asked me to walk for her. I did and she instructed me in holding my arms, moving my hips and in taking smaller steps. We walked back to the living room, she handed me a purse and a soft gray coat. She said ok Clara let's go shopping. I stopped in my tracks and said in public. She said you ninny, you look fine. I looked in mirror at a mature woman with slightly gray hair and sighed. She took my hand and walked me out to the car.
The first stop was Dress Barn, she looked the dresses over, picked out a couple and led me to the dressing room. She said try these in, when you have one on let me know so I can look, I will be looking at more things. I tried on one dress, it was dark blue with little polka dots and came mid calf. I opened the curtain and called for her, Joyce. She said I am over here by the pantsuits, come here and let me see. I was nervous with a half dozen women in the store. I gingerly walked over and found her, she had me twirl for her then said yes that is perfect. We were there for an hour with me trying on dresses, skirts, blouses and pantsuits. She picked out three dresses, including the polka dot, three skirts, three blouses, and two pantsuits.
Next stop was a lingerie shop for older women. I hesitated but, she took my hand and led me in. She picked out some bras, panties, hose, girdles and corset and hand me try them on. She bought me a pink bra and panty set, a light blue set, a white set and a black set with red roses on them. Also came several pair of hose, thigh highs and panty hose all in different colors. Then we headed for a shoe store, I felt awkward having a man handle my hose clad feet trying on different shoes. She was grinning the whole time. We then headed to a jewelry store where she picked out rings, earrings, bracelets and necklaces for me. When we left she announced it was time for lunch.
We went to a small local restaurant, walked in and I noticed other ladies here age seated at a large round table. The ladies called her over. I gulped, she took my hand and walked us over. Slowly she introduced her friends to me and told them I was her old school friend Clara. The ladies all hugged me, gave me a kiss on the cheek. I could not believe they did not notice I was a man. We sat down, they were hitting me with questions about where I was from, had I ever been married, did I have kids etc. Clara did most of the talking, interrupting them so I never had to answer. We had a light lunch, talked about sewing and they about how nasty there men were. We left with hugs and kisses all around and headed home.
Joyce then laid out her plans for me. How we would attend and have tea parties, attend sewing circles. I finally broke down in tears, thanking Joyce for all she had done and how I was happy with this. I then asked her how we could pull this off with my wife. She said not to worry as she found another man when she moved out of State and then told me she knew about my dressing as she had found some of her clothes out of place and knew it had to be me trying them on. I cried some more with her hugging me. She then told me there would be more to this transition, that I was to let my own hair grow out and we would get it styled at a salon. Then she announced we would be seeing her gynecologist tomorrow to get me started on hormones and a breast enhancement. I could not believe this was happening.
We went to bed that night, in the same bed, me in a powder blue, lace nighty with matching lace panties. We lay next to each other and had girl talk till we fell asleep. In the morning we work up, dressed for the day, I in the polka dot dress. She said today we need to work on your girl skills, as an older mature woman. She said we would be going to a seniors dance that night. All day we worked on talking, walking, sitting, grace and manners. We went to get ready for the dance. Hanging up for me was a beautiful floor length dark blue evening gown with matching blue strap two inch heel sandals. We changed into our evening attire. I remarked over and over how nervous I was and asked what if someone asks to dance with me. She put on some music and taught me how to dance with the man leading. She then said, don't get any ideas on picking up a man as you are mine.
We arrived at the dance there were 100 people there, the music was from the 40's. We sat a table with three of her friends, who were all remarking how gorgeous I was and that I better watch out for all the widowers. I just giggled and blushed and said not to worry. Joyce and I danced to a couple of songs, which was not out of place because many of the older ladies were dancing together. A slow song started when a distinguished older man took my hand and asked me to dance, I looked at Joyce, she nodded approvingly. He took me in his arms and the room went dim, it was pure bliss. He held one of my hands with the other placed on the lower part of my back. As we danced I sensed he was pulling me in closer till soon my head was resting on his shoulder and I could feel his hand had slipped farther down till it was on the upper part of my ass. The song ended but, I stayed in his embrace. I finally, gently pulled back and softly said I should join the others. We moved back to the table, they were gone. I found them on the dance floor with other men. My suitor put his hand around my waist pulled me close and kissed my cheek, I melted and sighed. We sat down at the table to wait for the others. He had one hand on my knee, which kept sliding up till it was on my thigh. The others came back and sat down. Joyce looked at me, grinned and winked. My suitor kept himself up close to me and bought drinks for the table. The last song started, he stood up, took my hand and led me to the floor. This time he pulled me close, my head on his shoulder and we slowly swayed. I became startled when I could feel his manhood grow and was pressing against my belly. But he had a firm gently hold on me. The song ended, he took a hand and lifted my chin toward him, I looked into his eyes and he kissed me, sweetly, gently on the lips. My body went limp, my mind was reeling. I whispered I had to get back to my friends. He put his arm around me held me close and walked us back to the table. Joyce was smiling and said well dear, we have had enough excitement for the night for two old ladies. I nodded, she took my hand and we started walking out. My suitor took hold of my other hand and walked out with us. We got to the car, he opened my car down, as I started to get in he kissed me again. Then asked me out. I looked at Joyce, she spoke up and gave my suitor her number and told him to call.
We got home, changed into nighties and bathrobes and had tea before bed. She said it is too late tonight to discuss men but, we will tomorrow. We climbed into bed, she snuggled up close to me, I laid my head on her breast and drifted off to sleep dreaming of dancing and kisses.
The next morning she suggested I put on the pant suit as I had a doctor appointment. We arrived at her gynecologist, a nurse took me back to an exam room, told me to undress and put on this flimsy paper thing and get on the table. I did so. The doctor came in, talked to me, telling me he and Joyce had already discussed my case. He pulled the top part of the paper thing down, took some measurements and pictures then pulled it back up. He then put my feet into the stirrups on the table, pulled them apart and lifted the paper thing again. He examined my ass and manhood. He then told me to get up and start getting dressed and he would be right back. He returned with a shot and pill bottles, he gave me the shot in my ass. Then told me to take two pills a day, one morning and one night. We left the doctors office and headed for the ladies lunch circle.
The ladies were all giggling and talking about me and my suitor at the dance. One of the ladies then remarked, by the way Joyce has told us all about you. We think it is wonderful you being an older woman as most men are gross. We continued the lunch with talk of sewing and flowers and fashion.
At home Joyce told me, we needed to talk about men. She told me not to get involved in an ongoing relationship as men would only disappointment. That it was ok for me to have a couple of dates to experience what every woman goes through but, to remember I was hers and only hers. I told her I would follow her advise and to remember I was only hers. We had supper, sewed and then headed for bed. Tonight would be different.
I had on a white lace nightie with matching panties, Joyce had went into the bathroom and came out with nothing on. I pretended not to notice and climbed into bed, she got into bed next to me. She then put an arm around me, pulled me close and kissed me. She said we are old maids but, I still have needs. I wasn't sure what to do. She guided me head to her breasts I started kissing and sucking on them, she was moaning. She then guided my hand between her legs and using her hand had me rubbing her. Soon she was pushing my head down to between her legs and told me to pleasure her. I began pleasuring her with her giving me instructions on what she wanted. She let out a moan and gasp and said OOOOOOO I am cumming. Then she pulled my head away, told me to freshen up my face. I came back she was in a long flannel nightgown, kissed me and said good night dear Clara.
I was sitting in a chair in the living room of my small apartment. Legs demurely crossed at the ankles. Legs that were encased in black thigh highs, the ones with the cute bows at the tops. Feet that were in black round peep toe pumps with 3 inch heels. He leaned over me and kissed me on the lips, a full romantic kiss on lips that were painted with Plump Lips plum shade lipstick. I was frozen in place and in time, intoxicated with this moment and a slight intoxication of white wine. He drew back slightly looking at my face, gold hoop earrings in pierced ears, rose blush powder on the cheeks, false eyelashes, a smoky grey eyeliner on the eyes with a light green eyeshadow. He looked down at my 36b breasts that were heaving against the strain of the black corselet lace bra that was covered with a white cotton blouse, a blouse that had lace trim around the circle collar and lace trim at the cuffs. His gaze move further down to the blue skirt that sat just above the knee, the skirt with the slit in the back. He moved his hands to cover my hands. False nails that were painted glossy plum, rings on two fingers of each hand. Bangles of gold bracelets on the right wrist. He looked back up, kissed me again with that full romantic kiss, lips slightly parting. He drew back and said I have always wanted you.
I had been dressing and wanted to be a woman for as long as I can remember. I use to play house with the neighborhood girls. Since they were older they would decide who got what role. I either played a baby daughter or older daughter and sometimes got to be the mom. I continued to dress throughout my teen years, when it was safe to do so. Things being what they are, someone who was born with male parts but, with a female mind, I tried to put it behind me and married. It was an unhappy marriage from the start and after a year came the divorce. I moved into a small apartment and behind closed doors began building a wardrobe and working on my womanhood.
I was sitting in my apartment on a Saturday evening, dressed as described earlier and evidently had forgotten to lock the door. Dave a long time friend walked in with a bottle of wine, wanting some buddy drinking time and found me in the chair.
Dave took my hand in his hand and raised me from the chair, he pulled me to him and we started dancing. I think Celine Dion was playing, it was all a blur. I was weak in his arms. We slow danced around the room, my head with shoulder length brunette hair with little curls instinctively dropped to his shoulder. The smell of his manhood was wafting in my nose, while the White Diamond perfume I was wearing was filling his. He turned his head and kissed my cheek and said again "I have always wanted you." I asked Dave how long he had known about me. He replied he had not known about this side of me but, confessed to me he was gay and in love with me. Dave continued that this just added to it.
We danced some more, shared some wine, while seated on the couch. Dave had his arm around me, he showered me with kisses on the lips, and on the neck. His hand was on my thigh, mine was on his and a look at his crotch told me he was aroused. He then took my hand in his, lifted me off the couch and with his arm around my waist led me to the bedroom.
We were standing in the bedroom, Dave slowly unbuttoned my blouse and took it off, he slowly unzipped my skirt letting it fall to the floor. He pulled me in close and began French kissing me. Dave then gently pushed me back onto the bed on my back. He stood before me and began undressing. He stood before me naked, a fit body from playing tennis and a large penis fully erect. Dave lay on top of me, kissing me, massaging my thighs with his hands, then reaching under and massaging my black lace bikini clad ass. He hooked his thumbs under the top of the bikini, lifted my ass up and slid it off me. I was kissing his neck and chest and slowly made my way down to his belly and that wonderfully shaped fully erect penis. I kissed the head of it, then began licking it with a slow swirl of my tongue. Dave was obviously enjoying this by the sounds of his moans. I soon wrapped my lips around the head of his penis, letting my tongue work magic. I then tried to take as much of him in my mouth as I could, bobbing my head up and down while my fingers massaged his full balls.
Dave rolled me back onto my back, lifted my ass with his hands and started kissing it. My cheeks soon parted and he began tonguing me. He stopped and looked at me and said "I want to make love to you." I moaned a yes please. He asked if there was any lube, I pointed to the night stand drawer which he opened and pulled out the lube. He handed the tube to me, I poured some on my fingers and massaged it onto his penis. Dave wiped some of the lube from my fingers onto his fingers and gently massaged it into my ass. I managed a whispered "Dave that feels soooo good on my pussy." He withdrew his fingers and placed the tip of his penis against my pussy. Feeling more like a woman than a man now than ever my ass had become a pussy to me. He gently pushed against me and was soon in. I wrapped my legs around his waist after he had placed a pillow under my ass and Dave slowly started making sweet love to me. I was lost in a dream world. After what seemed like eternity I could feel the most wonderful orgasmic sensation building in me. I was transformed into a panting, moaning frenzy and soon had a powerful orgasm. Dave continued his lovemaking and soon his strokes became harder and deeper, with a moan Dave came a powerful jet into me and collapsed on me.
I was kissing Dave and telling him I loved him. Dave rolled over off me, I laid my head onto his chest and was staring at the wonderful manhood that had just made me feel like a complete woman. Dave put his arm around me, kissed me deep and told me he loved me. Dave then asked if he could stay over. I told Dave he could move in and I would be his best girl ever. Dave smiled and said "And maybe the best wife ever."
This is a true story that happened to me in the early 80's. The names are changed to protect the innocent.
I was married at the time, out of work, was sitting in the apartment reading a magazine. It was two days before Halloween. There was a knock at the door, I answered it to find a friend of ours Greg. I invited him, he took a seat and we exchanged small talk. Greg asked "The Holiday Inn bar is having a costume party for Halloween. Do you and Lisa want to go with us?" I replied "I will have to ask Lisa but, I am sure we would." Greg said "What now that your home are you the housewife and she wears the pants in the family that you would have to ask?" I said " Ha ha funny. No just with her working long hours that would only be the polite thing to do." He said "Just funnin' you do get mad." We talked a little, then he had to leave. I said "Wait what are you going as?" He said "A woman track athlete and Sharon (his wife) will be my male track coach." I replied "Not sure what we will go as." Greg said "Go as a woman and your wife as the man like us." I said "Well I don't have anything to wear so will have to think on that." He said "Go by the salon today and talk to Sharon." I nodded and he left.
Sharon was the manager of a small salon, currently it was her and another girl Jill working in the place. I waited an hour after Greg left and drove to the Salon. My mind was racing as this would be the perfect opportunity to dress en femme. I had been a closet dresser for several years, no one knew. As I drove up to the Salon my heart was racing, my mind reeling, and my palms were sweaty. I had also been playing over the scenario as to how I would get Lisa to go along with this. Would she be mad, would she think it fun or would she not want to go.
I walked in the door of the Salon, Sharon was finishing up styling a client, Jill was sitting in her stylist chair. There was no one else around. We said our hello's and I picked up a magazine. The client paid and left, Sharon sat down in her chair. Sharon said "Greg says you and Lisa are going with us to the Halloween party." I said "Probably, just not sure what costume to pick." Sharon replied "Oh I thought Greg said you would go as a woman like him." I replied "Don't have anything to wear." Which was a lie as I had my secret stash. Sharon said "Go to a store and pick something." I said "Money is tight right now with me being out of work." Sharon replied "Well maybe we an think of something." She sat for what seemed an eternity but, was only a few minutes.
Sharon looked over at Jill. Jill is very attractive, short blonde hair, about 6' tall, not overweight but well built. Jill looked back at Sharon and said "What?". Sharon said to Jill "you two are about the same height and he doesn't weigh much more than you. You are single and have those come get flirty clothes." Jill looked at me for a bit, then looked back at Sharon, then back at me. Jill said to me "Be at my apartment first thing in the morning, I don't have any clients until afternoon." I looked incredulous. Could this be happening, was a woman going to help feminize me? I nodded my head yes, since my head was spinning and I couldn't talk. Sharon said "This is great. After you get fitted with the right clothes you can come to the Salon before the party and we will give you a makeover. Greg will be here getting one too." Again I nodded ok. I got my wits enough about me to say I better go and left. The girls were sitting there with big grins on their face.
I had supper waiting for Lisa after she got off work. She came in and said "Thank you dear for supper and thank you for doing the housework so well while you're home all the time." I said "It's the least I can do." I asked about her day, she said it was killer. We made small talk with me pondering how to broach the subject of Halloween. Finally I said "Greg came by and asked if we would go with he and Sharon to a Halloween party at the Holiday Inn bar." Lisa said "That would be fun. Do you mind if I go get a bath and head to bed? I am beat." I said "That's fine." She left for her bath and I cleaned up the kitchen. I finished my work and went to check on her. She was already asleep. Guess the costumes will have to wait till tomorrow.
I had Lisa's coffee ready in a go cup the next morning, along with breakfast. She was scurrying around getting ready for work. She walked into the kitchen, I handed her the coffee and she said "No time for breakfast, gotta run." She gave me a peck on the cheek and was out the door. I cleaned up the kitchen thinking when and how am I going to tell her about the costumes. I grabbed a quick shower, changed clothes and headed out the door.
On the drive over to Jill's my mind was in overdrive. When can I tell Lisa, should I even do this, I could just turn around and call it off. But I didn't the thrill of being dressed by a woman and going out in public was pushing me on.
I knocked on Jill's apartment door. She came to the door wearing a short black night gown. "Morning princess." Jill said. I was taken aback at princess. "Don't just stand there babe, come in we have a lot to do." I walked in and she said "follow me to my bedroom." Now I was nervous, a woman inviting me to her bedroom dressed in a short night gown who was intending on helping me get enfemme. We walked into the bedroom, there were 3 dresses hanging up, some shoes on the floor and lingerie on the bed. Lingerie! Was that hers or for me?
"Ok princess, take off those clothes." A lumped formed in my throat and I gave her a confused look. "Look, we don't have all day and I have seen naked men before. I need to see what I have to work with." I nodded ok and started undressing. I was standing before her in only my briefs. "Off with the briefs too. Those aren't feminine." I turned red and took off the briefs. My penis started to twitch and Jill grinned. "Relax honey, this will be fun. Now turn around." I turned around with her looking me up and down. "Ok babe, follow me to the bathroom." I followed trying to control my reaction to being naked in front of her. Jill turned on the shower and said "Get in." I got in the shower and immediately my penile reaction shriveled, she had it on cold water only. Jill laughed and said "Fixed that problem huh." She handed me a Lady Gillette razor and a can of shaving foam. "Shave all the hair off that body." Jill said. I gave her a questioning look, speech was still hard for me. "To be lady like you have to look lady like, hair is not lady like. You can turn the hot water on when I leave. Shave slow and close dear." She left the room and me to my task.
I had shaved all the hair off my body, legs, underarms and what little chest hair there was. I stepped out of the shower and started toweling off. Jill came back in and said "Not like that, pat yourself dry." I started patting dry. Somewhere in this process, she had me in a spell and I started obliging her directions. I started to wrap the towel around my waist, Jill reached out took the towel and handed me a bottle of Nair. "Your not quite done princess. Put this on all over your body, let it set 10 minutes then rinse off using a washcloth." I nodded ok and Jill walked out again. I put the Nair on, after a couple minutes it was burning. I didn't know if I could stand it. Jill called out "10 minutes are up rinse off then come back to the bedroom." I rinsed off the Nair, I couldn't believe the wonderful sensation of being silky smooth. Jill yelled out "Need you in here." I was enjoying the moment of soft smooth skin.
I came back to the bedroom with the towel around my waist. Jill reached out and took the towel off. Again my penis started twitching, Jill laughed and said "Someone is enjoying this isn't she." Isn't SHE! Uh. She grabbed a black thong off the bed and told me to step into it as she held it out. I steadied myself on her shoulders and stepped into the thong. She started pulling it up and came face to face with my penis. Jill grinned and said "Gotta fix that." She pulled something out of towel on the floor and then I felt the cold of a piece of ice hit my penis. I shriveled up and Jill said "That looks more like a lady's clit should." She pulled the thong up higher grabbed my package and pulled everything back, way back. Then pulled the thong up tight. I looked down at a flat crotch. Jill said "This is called a gaff, it belongs to a TV friend of mine who left it here." She has TV friends? Now my mind is racing and heart is thumping. This could be a good friendship.
She then held out a black lace corset that had underwire supports for the breasts. Jill had me step into it. She said "This is going to be a tight fit but, it will help give you the right shape." The corset actually gave my chest the look of little boobs. She produced some thigh high black hose, showed me how to roll them up and put them on my legs, then clipped the hose to the suspenders on the corset. Jill stood back to look, "Not bad she said, a little tape on the boobies and they will look real." She had me sit down at the chair to her makeup table. She had me take off the hose. She sat on the floor at my feet, took one foot and started giving me a pedicure. I was transfixed in time, I didn't want this to end. Jill painted each toe with a bright red polish. She stood up went to her closet and produced an auburn colored wig, it was shoulder length with soft curls. Jill positioned the wig on my head and fixed it in place. "Perfect" she said.
"Now for makeup." Jill applied a light face cream, then concealer, then a foundation. She explained to me what she was doing and using at a each step. Then blush, she then stopped and said "hmmm. Eyebrows." Before I knew she had tweezers and was painfully plucking away at my eyebrows. "Not much" she said "Just enough to create the illusion." She finished, thankfully, then started with mascara and eyeliner and eye shadow. Next the lips were outlined with a pencil and filled in with lipstick. She stood back and said "Perfect."
She had me put the hose back on, watching me closely. "Now princess, do we want a hooker like? Trashy? No, we want a high class call girl look." She took a dress off a hanger and instructed me to lift my arms. On went a little black dress, that fell just below mid thigh, it had a low plunging neckline and little straps. Jill stepped back and said "No, that's not it." She took down another dress, I took off the other. This next one was floor length, except there was a slit on the right side that came up to my upper thigh. The neck was a deep V which was trying to show off what little cleavage I had. "Hmmm." She said with a finger on her chin. She looked at the shoes on the floor and picked up a pair of strappy sandals, they had an ankle strap and a good 3 inch spike heel. Jill said "good thing our feet are about the same size." She had me sit down and placed a shoe on each foot. "Stand up princess." Jill said. I stood up, well I teetered up. She took my hand and helped me. She looked me over, "spin around princess." Jill said. I tried to spin, it was more of a totter. Jill laughed and said "We will work on the walk." "This is it. It's perfect." I asked Jill "Can I see?" She replied "Just a minute." Jill got a gold necklace and found some clip on earrings and a couple of bracelets. She fussed with the wig then said "Ok let me close the bedroom door, there is a full length mirror on the back." She closed the door, I looked in the mirror and got light headed. I couldn't believe it, I had never looked this good when I dressed myself. Jill laughed and said "Princess you like this don't know." I just dumbly nodded yes as a little tear started forming in each eye. Jill hugged me and said "It's ok babe, I won't tell that you are having such an emotional reaction."
Jill looked at the time and said "I hate to break up this party but, I am going to have to get ready." "Let's take off this dress and lingerie and pack them neatly." I started to softly cry, I didn't want it to end. Jill hugged me again and said "Don't worry princess I have a surprise for you." I took the clothes off, again standing naked in front of her. We packed the clothes. Jill went to her dresser and handed me a pink lace bra with matching panties. I looked at her, "Put these on princess, you have to practice for tomorrow." I put them on. She than handed me a pair of tan panty hose and told me to put those on. Jill went to her closet and produced a dark brown pleated skirt, a pull over sweater that was a dark orange and fuzzy. I put them on without being told to. She then pulled out a dark brown pair of pumps with a 2 inch which I slipped on.
Jill said "You can wear those today." "Stay here while I get ready, watch everything I do. When we leave follow me to the Salon so I can give you more instructions." I hugged Jill, softly sobbing a happy cry and said "Thank You so much!" Jill said "I think we have released a princess that has been hidden and that makes me happy."
Jill got ready to go the Salon. Me I watched every move. How she put on her make up and clothes, the motions she made, how she walked and talked. We hugged again and stepped out the door of her apartment. I froze. Jill looked at me and said "What's wrong sweetie?" I said "I can't go out like this." She softly smiled and said "You look gorgeous princess, just take little steps, mimic my movements. Think you are a woman." She took my hand and we walked to my car. She said "Remember you are a lady, swing your legs and think and be feminine." I nodded and got into my car. I waited for her to get into her call then followed her to the Salon.
I pulled up beside Jill when we reached the Salon. She got out of her car, started walking to the door and looked back to see me sitting in my car. She walked over to my car, I rolled the window down. "What's wrong now Princess?" Jill said. I said "I can't go in there, Sharon will see me and so will the other clients." Jill replied "Baby doll it's ok, no one will say anything. Besides I need to give further instructions so you look perfect tomorrow night." She opened the door for me and took my hand, and helped me out. We walked into the Salon arm in arm. Sharon was styling a client, she glanced over our direction said Hi and kept working. Jill told me to have a seat and handed me a Cosmopolitan magazine to read. She went to her station and started getting things ready.
Sharon and her client were happily chatting away, I was reading Cosmo trying to learn more feminine tips and Jill was getting ready for her first client. Sharon finished with her client who walked out the door with just a sideways glance at me. Sharon cleaned up her station, talking to Jill, then looked my way and said "You can go ahead and get in the chair, Jill is ready for............" Sharon looked at Jill who was grinning from ear to ear. Jill said "That's John, better known as princess." Sharon looked back at me and said "Wow, you look gorgeous!" I blushed and said "Thanks". Sharon asked "So why are you dressed now?" Jill answered her "Princess needs practice if she is going to win the prize tomorrow." Sharon said to Jill "You did a fantastic job." Then she looked at me and said "You can hang out here awhile today as a walking advertisement for makeovers. Maybe you will learn a thing or two as well." "You need a female name. Any ideas?" I said "how about Janet?" They both said in unison "That works!"
Sharon said to me "When a client comes in we will tell them we gave you a complete makeover and that you want to learn how to be a stylist. Jill and I will tell you what we are doing and how we are doing it to each client." I said "That would be wonderful."
The day progressed with me being shown off to clients, the clients being asked to spread the word about the Salons' work and being instructed in beauty tips and care. Sharon and Jill gave me instructions in how to walk, how to use my hands and arms, body posture and working on my voice pitch. I looked at the clock and said "I have to go get supper ready." Jill said "My aren't you the good housewife." I grinned and blushed and said "I try." Sharon said "If we aren't careful, we may make you a permanent fixture around here as one of the girls." Sharon said "Can you come back tomorrow when we open?" and added "Jill can probably find you some more suitable clothes." To which Jill replied "I can." I started out the door, stopped, and looked at them both. I was holding back tears as I was happy and also had a semi frightened look on my face. I said "I can't go home like this." They looked at me and said "sit down and we will take off the makeup and you can change in the back." Then they said "Does Lisa not know?" I said "No, I haven't seen her long enough to tell her." Sharon said "Don't worry I will take care of telling her." And added to Jill "What does Janet's costume look like?" Jill described the dress in detail to Sharon. Sharon said "We have a tuxedo that will fit Lisa, you are Lisa's paid escort." I nervously said "Ok." I sat in the chair, they removed the makeup, I went to the back and changed into my clothes feeling very sad. I waved a lady like goodbye and left.
Supper was on the table when Lisa got home. She came in an kicked off her shoes and sat down to eat. I asked how her day was, she said "killer". She said "Sharon called me at work and told me about the party plans." I felt the blood leaving my face. "She said Greg was going as a female track athlete and she would be his male coach and that you all had arranged our costumes." I nodded in agreement. "She said I dunno, seems a little weird but, well since you are in it this far we'll go ahead with it." She got up from the table and said she was going to bed. I could tell she was put out and that made me sad.
I had her coffee and breakfast ready the next morning, she grabbed the coffee and headed out the door without a word. She stopped at the door turned around and said "Sharon said I should come to the Salon after work to get ready for the party." And then she headed out.
I cleaned up the kitchen crying and feeling sad. Got a shower, shaved all over and used the Nair that Jill had given me. I headed out the door for the Salon. On the drive over I couldn't help but feeling confused and sad. On one hand I was thrilled that I had gotten to dress en femme and be as a woman yesterday. On the other I was confused as to what I should with my life. I cared for Lisa but, really wanted the chance to live as a woman. After the cold shoulder from Lisa last night and this morning I knew I would have to make a decision. I doubted seriously that Lisa would accept me as a female.
I arrived at the Salon, Jill was there before Sharon. She ushered me in the back, giddy to show me the outfit for the day. I got undressed and put on a matching lace turquoise bra and panty set. The panties were French cut. Before putting on the bra Jill produced dress forms to fill out the bra. she handed me a pair of light gray panty hose, then a dark green plaid, pleated skirt that fell just above the knee. She gave me an aquamarine blouse that had lace trim around the collar and ends of the sleeves. The shoes were a dark green pump with 3 inch heels. I hugged Jill and started softly crying. Jill said "Janet what's wrong?" I told her about the encounter with Lisa. Jill said "You and I need to have a heart to heart talk because I think you prefer your feminine side that I have let out." I nodded my head. She said "Now, let's finish getting you ready and give you another surprise."
I sat in Jill's stylist, she put on my makeup, then fixed the auburn wig. Then she produced what looked like a gun. I gave her a quizzical look. She said "To complete your look for tonight you need proper earrings." And with that pierced first one ear then another and placed in them big gold hoop earrings. Inside I was thrilled but, knew with this Lisa would probably throw a fit. Just then Sharon came in and looked at me and said "Janet, you are gorgeous this morning." She then asked if Lisa told me about their phone conversation. I said "Yes". Sharon said don't forget your voice pitch, I nodded. "Well" she said "what did she say?" I replied, watching my pitch, "Not well, she gave me the cold shoulder." Sharon said "I don't know why you married her anyway, she is an old fuddy duddy. She will just have to get over it." With that we went to work. Me as a walking advertisement and learning, even giving a couple of shampoos with positive praise from the clients.
6:00 we closed the Salon. Jill told me to go into the back room, take off my clothes and shower again and use the Nair and some moisturizer that was back there. They had a full bathroom with shower in the back that the girls told me came in handy. I showered, used the Nair the burn of which I was getting used to, then moisturized my body. Jill came back and told me to have a seat in the chair back there and started giving me a manicure. She applied false nails to make them longer and a deep red polish. She then redid my toes. Jill said "You are going to win that prize tonight because I am going to make you a knockout that the women will be jealous of and the men will want to take home." I blushed at that thought and sat there with a silly grin on my face enjoying the moment.
I heard someone knock at the door, it was Greg as I heard his voice when he started talking to Sharon. He asked Sharon "Where is that dofus friend of mine, did he chicken out?" Sharon replied "No he is in the back with Jill getting ready and you can't go back there until he is ready. And for tonight you will call him Janet." Greg laughed and said "Ok sweety."
A little later I heard another knock at the door and heard Sharon talking to Lisa. Lisa said a polite hi to Greg then said rather coldly "I still don't know about this." Sharon said "Lisa, this is for fun and besides you might win a prize tonight." Lisa then asked "Where is my husband?" Sharon replied "In the back, Jill is getting him ready." I could hear footsteps headed to the back then heard Sharon say "Not yet dear, wait till he is ready." Lisa said "I want to talk to him." Sharon said "Please Lisa just wait, besides we have to get you ready."
Jill looked at me while the conversation with Sharon was going on and said softly "Relax princess, I am here for you." With that she gave me a reassuring hug. Jill had me stand and slip on the corset, having already put the gaff in place. She then got out some medical tape and pulled my breasts together. No bra or forms here as the dress was meant to be worn braless. I pulled on the hose and fastened them to the suspenders. Jill commented how good I was getting at that. Next came the makeup, she worked for a long time on my makeup. Night time look is what she said. Bright red lipstick, with a silver sparkle eyeshadow. Oh yes she had also put on false eyelashes. Jill looked at me and smiled and said "Perfect!" Next came the dress, Jill zipped it up in back, I had been trying to look in the mirror but, she said "Wait princess." Then she produced the shoes, same black strappy sandals with the ankle strap except these had a 4 inch heel. Jill said "You can handle the heel, just remember lady like and the practice you have put in with the others." She put a gold necklace around my neck, 3 sets of bracelets on each wrist and fake diamond rings one on the finger of hand one for a finger on the other. Then she put on wig adjusted it and fixed it on my head then a curling iron on the curls. Next she produced a bottle of Chanel No. 5 perfume and sprayed my neck and wrists. "Now" Jill said triumphantly "my princess can look in the mirror."
I slowly stood up, testing myself on the 4 inch heels and looked in the mirror. I almost fainted. I wanted to cry out and Jill is that me! Jill cautioned me to hold back the tears so as not to ruin her creation. I hugged her and thanked her over and over. She was grinning from ear to ear. She kissed me on the cheek and said "Walk around for me princess." I walked around, placing one foot in front of the other with a catwalk like walk, trying to remember to sway my hips. Jill was still grinning and said "If you don't win tonight, you are my grand prize."
We heard Greg call out to us that we needed to go ready or not. Jill yelled back "We are ready." I grabbed Jill's hand and said "Lisa". Jill said "I will walk you out and go with you all tonight for support." I hugged her again and thank her. Jill then handed me a small black evening purse with a little gold chain for a handle, she said "touch up makeup is in there and your ID and cash.
Jill opened the door of the backroom, took my hand and we slowly walked out. Greg said "whoa buddy is that really you! You look like a model! And the grand prize winner for tonight." Sharon was grinning from ear to ear and said "So perfect." My vision was a little blurry from trying to hold back tears, Jill still had my hand in hers. I looked at Lisa, dressed in a black Tux with cumberband, her hair with gel in it pulled back to look manly. She was just staring at me. I couldn't read the expression except to think it looked cold and yet, a look of surprise and marvel. Sharon broke the silence, looked at Lisa and said "this is your paid escort for tonight Janet." Jill walked me over to Lisa, crooked Lisa's arm and slipped mine through the crook. Lisa was just looking at me not saying a word. We all walked out to Greg's van. Sharon escorting Greg properly, opened his door and said "M'lady your chariot." We walked to the side door Lisa opened it and got in with me standing there, Jill helped me in. Jill got in the back and we drove off.
Greg and Sharon were chatting away happily and singing with songs on the radio as we drove to the Holiday Inn. Jill sat in back not saying anything but, with a reassuring hand on my shoulder. Lisa stared straight ahead, with a glance over once in a while my direction. We arrived at the Holiday Inn, Greg started to open his door and Sharon said "You hold on there girly." She got out, went over and took Greg's hand and helped him out. Jill got out of the back and opened my door and helped me out. Lisa got out and started to walk toward the bar when Jill said "Excuse me sir, you forgot your date." Lisa stopped, Jill walked her and I up to Lisa, crooked Lisa's arm and put mine through it. Lisa started to walk off at a fast pace, Jill moved up beside me took my other arm and slowed down the pace.
We walked in the already bar and found an empty table. Jill sat on my left, having helped me in my chair with Lisa on my right. Greg ordered drinks for us. Jill whispered in my ear to only have one or two as going to the bathroom might be an issue. Greg and Lisa had got up and were dancing. Jill finally asked Lisa if she were going to ask her date Janet to dance. Lisa shrugged her shoulders and when a slow song came on took my hand and led me to the dance floor. We danced but not cheek to cheek. I could feel the tension. Later Jill asked Lisa if she could have a dance with me. Lisa shrugged her shoulders and said "I don't care." Jill slowly walked me out to the floor, Jill said "I can't believe she is being such an ass. She doesn't deserve someone as good and caring and sweet and I might add beautiful as you." I replied "I didn't think it would be this tough but, you are the sweetheart and we will need to have that talk very very soon."
Soon the MC got up and asked for the contestants to walk in front of the stage for the panel of judges. I looked at Lisa and asked her "Are you coming?" She replied "No". Jill, Greg and Sharon looked at me and said come on you are going! Jill helped me up, I walked the bar floor swaying and sashaying, forgetting all about Lisa. The MC announced the 5 finalists, I was one of them. We walked some more in front of the judges. The MC announced the order. 1st place was some guy dressed like a tube of Preparation H and the check, I was announced as 2nd place with a gift card for, get this, MAC cosmetics.
I went back to the table, Jill, Sharon and Greg said I should have won. Lisa said "Are we ready to go home." Greg said "What's your hurry the evening is still young." Lisa said "I am going outside I have a headache." With that she got up and went out the door. Sharon said "Screw her, we are going to have fun. Janet don't you worry we have your back."
Jill and I danced some more, Greg danced with me once as did Sharon who put on a show making like she was putting moves on me. Several people came up and said I should have won, Jill would respond with a yes he should have. The women would then reply with an astounded "You're a guy!" Lots of business cards for the Salon were handed out that night. The men would reply with something like "No way your a dude, you are too sexy and beautiful." All that lifted my spirits and helped me forget about Lisa, at least for the time. Greg finally said "We should go, I have to work tomorrow." "But first there is something we want to give Janet." I looked at him puzzled. Sharon said "Jill and Greg and I were talking that you may have drummed up a lot of new business for the Salon tonight so here, here is $100 for being a walking advertisement." I looked at them, not sure of what to say and with such gratefulness I started to cry. Jill took my arm and said "Don't ruin the makeup. Please take the money." I took the money, said "Thank you so much." And hugged each of them. Jill took my arm and we made our way out.
Lisa was sitting outside the bar, got up and followed us to the van. Greg drove this time, Jill got my door for me again and helped me in. We drove to the Salon, with just a little chit chat. At the Salon Jill helped me out of the van and walked me to the door, We went in, Greg and Sharon said goodbyes and left for their house. Lisa walked in the Salon grabbed her things and left without a word, leaving me and Jill.
After Lisa left, Jill told me to sit in her stylist chair. I sat down and broke down crying. Jill hugged me close and said "Princess, if you want to talk now we can." I said "No probably not now." Jill said "Janet, if you want you can stay with me tonight." I said "I should probably go home and get whatever is coming over with." Jill said "If anything happens, now or anytime, you come to me." I told her I would, hugged her close and thanked her. Jill said "You know Sharon and I were talking about hiring you at least part time to help in the Salon. We would love to you here." I asked "As Janet or me?" She said "Janet would be nice but, I am sure either way would be fine." I thanked her again and told her I would think it over and that I wasn't sure how it would set with Lisa. Jill pulled away from our hug, stood in front of me and looked me in the eye. "Princess, that bitch does not deserve you! You need to start thinking about you and your happiness too. Got it!" I nodded my head.
Jill said "Well does Janet go home to Lisa or?" I shook my head "I don't know I am confused right now." She said "Then let me decide for you, we will take off this dress, you put on what you wore today and let Janet go home." I nodded ok. Jill helped me undress, I put on the skirt, blouse and shoes from earlier. I hugged Jill, said "Leave the door unlocked." She said "Princess it will be." And I headed out the door.
I drove home crying. I almost did not go up to the apartment, I almost got back in my car to drive to Jill's. Finally I unlocked the door, the place was dark. I thought what if she has left. I slowly walked back to the bedroom. Lisa was in bed, maybe asleep maybe pretending and not wanting to be bothered. I walked back into the living room, trying to decide what to do next. I ended up going into the bathroom, looked in the mirror at Janet and thought that is who I really am. I slowly started removing the makeup, took off the skirt and blouse, hose, bra and panties. I found some nail polish remover and went to the kitchen and remove the polish from my nails. I looked at my toes and decided to leave the polish on them. I took out the earrings, looked back at the nail extensions and realized I didn't have any way to remove them. I finally got a pair of clippers and cut them back. I went in and laid down on couch, covered my self with an afghan and cried myself to sleep.
It was late when I woke up. I laid on the couch listening for any sound from Lisa, after a few minutes I slowly got up and walked back to the bedroom. She was not there. I wondered if she had left me, no her clothes and other things were all still here. I thought about calling her at work but decided if she were she would get mad for interrupting her. I sat down in the kitchen to ponder my dilemma. I decided to shower and go see Jill.
I drove over to Jill's apartment and knocked on her door. She answered wearing only a robe over a naked body. I said "What if a stranger came to your door and saw you like that?" She sleepily replied "That's what peepholes are for, come in princess." I came in and sat down, Jill offered coffee. She said "so what happened?" I told her the whole story. Jill said "Princess I am going to give you some advice. First as I said last night that bitch does not deserve you. You need to wake up and realize she is going to hurt you worse than she already has. Second, leave her, leave her now! Move in with me until you get back on your feet. We can work through your issues and you can be Janet all you want." I looked at Jill letting everything she said soak in. I replied "I have no job, no money, nothing." She said "You have a job! At the Salon! And I can cover you until you are settled." I said "Jill I am just so confused." Jill moved over next to me on the couch and held me. Finally she said "Remember the gaff and how I told you it belonged to a TV friend?" I nodded. "She lived with me for a while so I know what you are going through and how to help. Please princess don't pass this up." We sat and hugged each other for a while, every so often me crying. I said "Jill, I first need to meet with Lisa face to face and talk this out." Jill said "That is fair enough." We just sat for awhile, not talking just holding each other. I said "I should go and find Lisa." Jill said "Princess I am always here for you."
I drove by Lisa's workplace, her car was there. I then headed home and started fixing supper. Lisa arrived home, I said "Supper is ready." She said "Good I am starved." We ate in silence finally I said "Lisa about last night." She interrupted and said "I guess it's just work and all getting me down, we should have just had fun with it." I then said "I have a part time job." She said with a smile "Really where, doing what?" I said "At the Salon helping Sharon." Lisa gave me a quizzically look, then said "I talked to someone today who has a full time job for you." I hung my head and said "Ok".
I applied for the full time job and got it. I told Sharon and Jill about it and thanked them. They both said, they would sure miss me working with them. I said me too and started to leave. Jill walked me out and said "I you sure about this?" I said "Yes the money is good." She then said "You are welcome to my place anytime for some Janet time." I hugged her and thanked her and said I would take her up on it.
3 weeks later I stopped at Jill's for Janet time. She was there crying, I asked what was wrong. She said her father had gotten very ill and she needed to move back home to help. We hugged and cried together. Then Jill helped me become Janet again, we cried and hugged some more. She took pictures of Janet. She said she hoped I would come to my senses, leave the bitch and let Janet out. She said Janet was the best girl friend she ever had. She gave me her parents number and said call when you can and hopefully we could be together again. I left.
I called Jill a week later, she said her father had passed away. We cried together on the phone. She said she was holding the Janet picture close. I tried calling again the next week. The number had been disconnected.
The following month Lisa and I separated. She had been caught stealing at work and turned out that was not the first time she had stolen from people. I had moved out.
I tried to find Jill but had no luck. Sharon told me she had lost track of her too.
The greatest mistake I made was not taking Jill's advise.
The End