Lori; Substitute Wife

Lori; Substitute Wife

Sis worked for a security company doing certain surveillance jobs as requested. Most of the time it was just following someone and making sure they did not get them selves in trouble. Most of the people she was paid to keep track of were fairly high profile, so were instant targets for news media and other individuals who had varied and nefarious reasons to exploit those people.

Quite often I got invited along, two people out wandering along not standing out like an individual would be. In this particular case me being along saved the day. I liked to dress all femmy, not quite sure what group of people I would be classified with.

I don’t think I was transgender, I still appreciated my time as a male, well that might be debatable. Maybe somewhere between a tranny and a cross dresser, if that was even possible. I loved the clothes, makeup, heels, okay I loved every bit of being a female.

Tonight I was dressed from the skin out as a female, a way too tight sweater dress what someone might see. It was one of my older purchases, one that I adored and found any excuse to wear it often. My makeup was daytime appropriate, having just applied another coat of lipstick to my lips. Riding along with Sis allowed me to get out in the real world without all the stress of going clubbing.

Her current assignment was a CEO of a prominent company who had been in the news a lot, not all of the publicity in his favor. It was thought he had gathered a small pact of paparazzi that were just looking for a chance to take a few pictures, then exploit the story, or better yet make one up to suit their needs.

The CEO was typical member of the male gender, instead of laying low and waiting for things to blow over he continued in his ways of late, almost inviting trouble to find him. The company he worked for hired Sis’s company to shadow him, and try to minimize any potential scandals if possible. The company’s financial status was far from perfect right now, changing a CEO would only add to the disaster that loomed over them.

I had been out with her several times in the last few days, as we followed him around, noticing the pact of scum that had been following him at a distance. It was obvious he was totally unaware of the scum, not even realizing we were a constant companion to his travels along with the others. Sis perked up when he drove to a motel on the edge of town.

When he pulled in to the parking lot and drove to the back of the motel she knew what he was thinking about doing. It was a motel known for being used when a prostitute is being met for a rendezvous.

She parked a few spaces from him and told me to approach him, pull him into a hug and whisper in his ear that he needed to drive you back home, the photographers were already parked out front waiting for his next move. She would meanwhile handle the prostitute and make it seem that he was just meeting me for a secret rendezvous.

I got out of the car and made my way to him quickly putting my arms around his neck and hugging him tightly whispering that he needed to take me to my place. That part went according to plan, however the next part was not.

He presumed me to be the prostitute and kissed me on the lips in a very passionate way. I tried to push him away but he was so wrapped up in the kiss, that I found it impossible to get him separated from my lips. Then we have the secondary problem, his erection quite noticeable and tenting his pants to obscene proportions. The sweater dress being so tight, his erection more then just felt as it pressed into my skirt. He pushed tighter to me as his erection pushed deeper into the skirt as I tried to get his attention.

Finally what I had said initially sunk in and he broke off the kiss and looked at me with pleading eyes. I mentioned that the press was out front waiting for him, we needed to hurry. I hung on to him as I encouraged him to head to his car. As he opened his car door I slid past him into the front seat, keeping me in front of him for most of the time. I told him where to take me, but that was changed a few minutes later when sis texted me.

She wanted him to take me to his home, and to stay there until she called. No visitors, no phone calls and stay put were given in a straight forward manner as she told him directly, then promptly ended the phone call.

It took him a few minutes for all of this to sink in, but eventually headed to his home. As we pulled out in front of the motel he saw all the press standing there, several of them inquiring at the office as to what room he had rented. He swallowed hard, but was able to concentrate enough on his driving to get us out of there.

I looked behind us, not seeing anyone following us so maybe we made a clean getaway. I knew once the press found out he was not there, some of them would head to his house, looking for him.

He parked in his garage, and closed the garage door with his remote. I saw him let out a breath, apparently all of this had gotten to him and he was visibly shaken. I suggested we get inside, Sis would probably being calling soon on his land line. We ended up in his living room, after a few minutes of silence he asked who I was and if I was hired by his company.

I told him my sister was hired by them, to keep an eye out for him, exactly what she had done tonight. When she calls she can explain everything else to him. After a few more minutes he swallowed hard again and apologized for kissing me at the motel. I smiled, told him it was okay, and then made him blush when I told him that was some kiss.

A few minutes later Sis called and they talked for quite some time. Several times he looked my way, I figured the conversation at that time was about me. After about twenty minutes she asked to talk to me and he handed the phone over.

Sis told me that several of the press had already showed up at the house, parked in the driveway of an abandoned house a couple of doors down and across the street from his house. When she drove by she noticed a dish set up by the side of one car and a camera on a tripod next to it. The camera had a telephoto lens mounted on it, the dish used to listen to conversations anywhere in the house. They were still setting up when she drove by the first time so probably nothing was heard when we first got to the house.

On the phone conversation right now she was using a scrambler that emitted a tone that masked most any conversation as far as the listening dish was concerned. Once the phone call is over we had to watch what was said, staying away from any windows and doors. I was to play his wife, his real wife leaving him several years ago and has not been heard from since.

We were to sleep together in the same room and interact with each other when getting ready for bed and in the morning as he got ready for work. She was sorry that I got involved in this but until tomorrow she had no way to tidy things up. I was cautioned again to watch what we talked about, if anything was talked about make it about the marriage. I handed the phone back to the guy and she told him the same thing and then hung up.

There was quite a bit of eerie silence, neither of us not knowing what to say. He got up and reached for my hand, then led me to his bedroom. He showed me the bath, and then a closet that held a lot of his wife’s clothes. He told me to look for a nightie and he would take a shower to let me have some privacy. That last said in a whisper in my ear. I smiled and kissed him on the cheek.

He stared at me then melted a little giving me a tender hug. He headed off to shower and I looked in the closet to see what his former wife had left. It was apparent she left in a hurry, since there didn’t seem to be anything missing. The closet was full, high heels on the floor and underwear lined up in clear plastic boxes on shelves at one end of the closet.

I found a nightie, after undressing I slipped it on, it was a little tight in the waist but otherwise if fit pretty good. I found clean panties and put them on. Then a robe to minimize the sexual aspect of the nightie. The nightie was far from matronly.

I decided to play the wife part for awhile, going to the kitchen and seeing what was available to make for a snack. From the amount of pizza in the freezer he must like pizza. I found a smaller one, started the oven and placed it inside. There was tons of tea on the counter almost every conceivable kind represented. I chose one that I liked to drink and made up a pitcher of it. I found some cookies in the pantry and some containers of pre-made icing so I iced a few cookies planning to slip them in the oven after the pizza came out warming them a little so they would taste like fresh baked.

I walked around the house looking at everything, trying to see what he was like. You can often tell what a person is like by looking at how they live. After my tour I checked the pizza then sat on a bar stool by the serving bar, from the few crumbs left on the counter most likely where he ate all the time.

I cleaned the counter and found a couple of glasses for the tea, having to wash them also since they were far from clean. I set them on the counter and turned to the door to see if he had finished his shower. He was standing in the door frame smiling at me, then walked over and hugged me giving me another kiss on the lips. He did tone it down some from the kiss at the motel though.

I pushed him back a little, this was progressing a little farther than I intended, and much faster than I could handle. I took him to the bar and pushed him onto one of the bar stools. I shook my finger at him, as he smiled and reached for me again. I evaded his hands and walked over to the oven to check on the pizza.

I turned the oven off, a few minutes more in the warm oven and it should be ready. I retrieved the glasses, filled them with ice then poured the tea. As I placed them on the serving bar, I had to dodge his roving hands once more. I took out the pizza, cut it into pieces and placed it on the counter. Then I placed the tray of cookies in the oven, with the oven door slightly open. They would be warm but not hot.

I found my bar stool and moved it a little farther away from his, smiled and parked my fanny on it. I reached for a piece of pizza took a bite and savored the taste. He obviously bought the better brands, since this one was superb. I had found some Italian dressing and sprinkled a little on the pizza as it was cooking, it blended the flavors better and enhanced the taste of the pizza. I guess my acquired husband had finally relented a little taking a piece of pizza for himself and letting out a moan of pleasure at his first bite.

He got up and moved his stool closer to me and finished his first piece with his other hand on my thigh. He definitely has a one track mind, maybe he will eat most of the pizza and take a nap. At least I can hope.

We watched what we said to each other, in case we could be over heard. The cookies were also a hit, I manged one, while he ate all the rest. After the pizza was consumed I wrote on the pizza box, that we should go to bed, but nothing but cuddling allowed. I warned him I had a black belt in Karate and I would stop any effort on his part to use his do hickey where it was not wanted.

He smiled and crossed his heart. He wondered off to the bedroom trying the hurt puppy dog look and I cleaned up the kitchen. When finished I went to the bedroom, slipped off my robe and climbed under the covers. A bath or shower would have to wait until tomorrow while he is at work, at least my body will have something between the two of us.

He did go right to sleep, this time it was my turn to let out a huge sigh. He was good the next morning as he got ready for work. I did get a kiss on the lips and then he was gone. When I was receiving the kiss I noticed his crotch, his organ once more inflated wanting to stab something, anything will do.

Sis called a little later wanting to meet me at her beauty salon, she had made appointments for us and we could use the time to discuss what next as they made me pretty. Her words not mine. I arrived but did notice that I had a tail, the press must be getting desperate to end up following his supposed wife for a story.

Sis was already there, her hair in curlers as I was taken to a station to have my hair washed and conditioned. Once that was handled she grabbed my hand and dragged me to their lounge, where they had soft drinks and some snacks for their customers.

Sis explained that the press had already made some inquiries about his wife, even dragging up a picture of her from the newspaper files. Luckily, I looked enough like her that my role as his wife should not be questioned.

As far as sis could tell the wife had found someone else and they were living somewhere in South America. The information from a school chum of the wife, who still kept track of the husband for the ex-wife. Apparently she had asked for a divorce, but he had ignored her request and never replied to any of her emails. So I will need to be the wife for awhile while Sis tries to get the press off his case. She is hoping that things at his company will smooth out a little, thus reducing his status as an integral part of any story.

I asked her how I can control his horniness, since anytime he is near me he is ready to stab something. She thought for a minute, then a huge smile came over her face.

“Yep that will be a perfect way to combat his lust and take the pressure off of you.”

I looked expectantly at her, waiting for her to tell me what she had come up with. Then the three words that immediately sent shivers through my body were voiced.

“A fake vagina. I know the salon can handle that procedure here and now. So by the time you get back to your home you will be ready to handle any and all expectations made of you by your husband.”

I didn’t faint but it was close as I wavered a little between consciousness and out to the world. I did manage to ask why me.

“Look you enjoy dressing as a female, now you can experience the other part of being a female. It is not all clothes, beauty salons and shopping. So you get to do what most housewives do every day, and maybe learn something about the superior gender. Besides you don’t have anything else to do, this will keep you off the streets and out of trouble.”

“You will also learn that women are the superior gender, a simple thing like getting sex and he will do anything you want. Now let me arrange your sex change, then we will have time to do a little shopping before you head home to your hubby. Just think a warm stiff penis slipping into your moist vagina and the fireworks starts.”

She played with her phone for a minute then a smile appeared on her face. Yep they can work you in right now. One hot moist pussy coming up.

“Oh gawd, do you have to go into detail. Surely you are kidding me.”

Just then a tech comes and gets me, taking me to a private room in the back of the salon. As I am led away I looked back in hopes of being saved, sis just smiles and goes back to reading her magazine. The tech spreads a cream over the entire groin, leaves it for a while and then wipes it off, the small amount of body hair that was there now gone. Junior now looked quite pathetic, since his camouflage had been removed.

The area around my male organ is thoroughly cleaned, then he is glued back between my legs. I now have a flat front like any other female would have. She lifts up a silicone vagina and then positions it over my male organ, making sure the tip of my penis is in the right place. Then it is glued down to my groin, and some semi-permanent makeup used to blend it in with my natural skin. Just like that I am a female as far as genitals is concerned.

I looked down there again, and my mind has already succumbed to the lure of a female vagina, picturing a male organ sliding into the warm moist slit. The tech wanted to know if I wanted to try it out, but I refused, I am sure it will get a work out soon enough. Back to the lounge, then both of us are placed under hair dryers so that our locks can dry.

Our hair styles are brushed out after the curlers are removed, then a touch up of our makeup and sis gives me a tender hug. As she walks away she turns and says have fun, but please keep the noise down. I make my way back home, his home, noticing that the group across the street has grown some. Potential stories must be at a premium right now.

I let myself in then walk through the house seeing what this housewife needs to do, to fulfill my part in this scenario. I find some meat in the freezer, from the looks of it no telling how long it has been there. I decide to cook it up, maybe a slow cooker might be best since I have several hours yet before my hubby gets home. Sis had postponed the shopping trip to another day, since she received a text message that needed to be looked into. So cooking something for dinner and cleaning up around the house will have to do for my afternoon entertainment.

The meat turned out to be okay, then I added potatoes and some onions. The juice off the meat will make some tasty gravy, and round out the dinner offering. I made some more tea, this time another variety from his large selection. I decided I needed some different clothes for dinner, maybe if I am the aggressor in the romance department it might throw him off his game. I found some lounging pajamas, thin lacy and downright obscene. If they don’t arouse him quickly and make him stiff he is already one foot in the grave. I did smile some, this just might be fun.

I heard his car in the garage and ran to the door, wanting to give him a wifely welcome. As he came through the door I wrapped my arms around his neck and planted my lips on his. I did catch him by surprise as he didn’t know quite what to do. He quickly gave in and returned the kiss our tongues actively in pursuit of each other. As he backed off he took in my appearance his penis quickly rising to attention.

Before he could plan an attack I led him to the table and pushed him down in his chair. Poured him a glass of tea over ice, then went to the kitchen to retrieve the food. His eyes locked on my tush and what he could see through the pajamas. It took me three trips to get the food to the table, his eyes never leaving my body. I kind of liked the attention, making me feel wanted. I dished out some of the food on his plate, then some on mine.

Meanwhile he had taken a bite of my offerings and let out some type of moan/groan I presume in appreciation of what I had made for him. I knew he was having trouble, deciding whether to watch me in the pajamas or eat some of the delicious food. I didn’t make it easy for him as I was constantly adjusting the top over my breasts or moving an erstwhile breast back into the built in cups of the top.

Each time I looked up his eyes were glued to my breasts, once he almost spilled all of his drink down his front while watching me move a breast back into place. When his eyes finally left my body his drink was nearer his ear then his mouth. Yep this is fun.

I received his help clearing the table, although I had told him I could handle it. Lets face it now that the food is gone he can spend all his time ogling my body. As soon as I declared the clean up complete he grabbed my wrist and led me to the living room. He sat me on the couch, then attempted to park his body as close to me as he could. He whispered in my ear, that dinner was delicious, but the way I am dressed far exceeds any dinner I might have made for him. He wants to be good, but it is so hard. He did place my one hand on his penis, there is no doubt of his arousal.

We chit chatted keeping our voices low, just barely above a whisper. I decided to tell all, it is not fair for me to deceive him, even if the original reason for the masquerade was to protect him. After I had told him I was a male underneath all of the feminine clothes and padding he pulled back a little, carefully examining me for any tell tale signs of that fact. He leaned in closer and kissed me on the lips, putting as much passion in the kiss as possible. When he broke off the kiss I had to compose myself, my breathing ragged and my heart rate soaring.

His whispered response, nope you are female and lets not bring up that subject again. The cuddling, kissing and romantic adventures continued for at least an hour. Then he decided we needed to move our activities to the bedroom.

Like last night he was a gentleman, taking his shower first while I prepared myself for bed. Makeup removed, hair in a braid and a new nightie and I joined him after using the bathroom. I was pulled closer and held tightly. He thanked me for the wonderful dinner and for being so nice to him asking if I was available to fill the job permanently. If so he was ready to sign a contract. I looked at him to see if he was serious, receiving a kiss on the end of my nose as his arms engulfed my body and held it tightly. Before long he was asleep, leaving me quite a bit to think about while being held in his arms. That familiar feeling of something poking me in the butt was back though, a little harder and stiffer than last night. I too nodded off sleeping soundly until he kissed me on the lips as he left me on his way to work.

I laid there, that is two nights in a row of him treating me like a treasured commodity, even though I had divulged to him that I was male underneath the clothing. He was treating me like a wife, maybe I need to look into his former wife, why she left and what kind of a person she was. Time to call Sis, let her gather up the information for me.

Of course, Sis gave me grief, accusing me of falling for him, lots of giggling from her in that short conversation. She did find out about his wife, sending me an email with a whole history of their relationship and eventual parting of the ways. She did it in her usual way, an email leading to a file on her website with all the info spelled out therein.

His ex was apparently a gold digger, hitching her wagon to an up and coming executive and riding along till the wagon was ripe for plucking. About the time she was thinking of taking him for every penny she found an admirer, this one richer in many ways. She left her current husband wanting to not miss out on this new boyfriend.

He lives in Argentina and along with being wealthy owns a considerable amount of land. He was heading back down south and invited her to go with him. She has indeed asked for a divorce several times, but James has left any requests unanswered. So far no lawyers have been consulted, but it is inevitable at some point in the future.

I resorted to cooking another pizza for tonight, this one an extra large with everything on it. I hunted through his cabinets for something to add to it, making an okay pizza spectacular. More Italian dressing, some green olives and some almost out dated Parmesan cheese. I tried a bite after it had cooked, luck was with me, this one tasting better than the fist one I had fixed.

I met him at the door again, this time in a pencil skirt and lacy blouse. My bra showing through the blouse. The requisite passionate kiss and then led him to the kitchen. I will have to watch myself, these kisses are getting to be habit forming and so enjoyable.

My offerings food wise were quickly consumed, he even helped me straighten the kitchen and wash the dishes. He had been a little quiet tonight, like he had something he wanted to bring up but did not know how to do it. Finally I told him to spit it out, at the worse I will find something heavy and throw it at him, at the best he might get a kiss. I sat back letting him squirm trying to get comfortable and able to discuss what he wanted.

He surprised me my telling me that his divorce is final now. He signed the uncontested divorce papers just yesterday. Her boyfriend wanted to get married, so to be able to do so meant she had to get a divorce. Now for a few things you probably are not aware of.

“Your sister and I are old school chums, even living together for a few months in an apartment shared among six people. When the press started following me I contacted her, needing her help in how to deal with them. We shared several dinners as we tried to figure what could be done. Then she came up with the idea of getting the two of us together. She has been thrilled at how successful it has been, now considering her hand at match making as a profession.”

Since you have arrived the press has backed off some, since there is no story in a couple exchanging loving embraces.

“When I made the comment about making it permanent I was serious, I would like you to marry me and become my wife. Since then you have shown me what married life could be like, something I never experienced in my earlier marriage. I do love you from the first kiss at the motel I have fallen for you, never wanting to be without you in my life. I have an engagement ring for you, hoping you will accept it and agree to be my wife.”

He reached into his pocket and retrieved a gorgeous diamond engagement ring and slipped it on my finger. I was already shedding tears, mouthing yes and trying to keep the tears from my eyes so I could look at the ring. I sensed the time was here for a kiss, grabbing his head in my hands and kissing him hard on the lips. He tried to take control, but this was my kiss and I was controlling the action.

It lasted forever, I was not even letting him have a chance to take a breath. Tongues met and exchanged fluid, but the lips was where all the action was. When I finally did break the kiss, I giggled some, he had more lipstick on his lips then I usually had on my lips. He looked cute in lipstick, so I leaned in again and sampled the merchandise once again.

When things returned to normal, what ever that is he suggested a trip to Vegas, not wanting to waste any time and take a chance on me changing my mind. I don’t think he has to worry about that, but I am not going to tell him that. Well we didn’t wait for things to settle down, we were on a flight the next morning and were married and back home that evening. I was now Ms. Lori Walker and so happy.

He kept asking about a honeymoon, I just shook my head no, our bed will be sufficient, he just needs to stay in it for the duration. Other than a few snacks that is where we stayed, seven days of sexual bliss. On the last day he was having trouble getting it up, informing me he had to go to work so he could rest for awhile. That night I used up his one day of rest and more, suggesting he eat more carbohydrates and protein so that he could please his new wife.

I did deal with Sis, finding her a stud of her own, then arranging for them to be locked in his home for the long weekend. I received no complaints from either of them, plus if sis wanted out she had a lock pick in her purse.

It started as a substitute wife, but ended up a permanent wife for my husband. Luck, maybe fate, even a scheming sister, but I will happily settle for any and all of those reasons.

© 2016 thru 2024 by Francesca Walker

Gigi; Slow Trip To Femininity

Gigi; Slow Trip To Femininity

Annabelle and I were heading into our fourth month of a relationship. She had made the initial overture to me at a school dance in late September. I was bored, nothing to do except homework, so decided to go to the dance, intending to maybe find someone and share a few dances with them. The homework that was left for me to do was difficult, and my mind was not ready for additional stress. So, going to the dance and maybe have a little fun looked quite attractive. It was a school mixer, most people showing up without dates.

I made my appearance checking out what was happening. The band they had hired was good, playing a lot of pop songs from the seventies. I danced a few numbers, but no one seemed to be that good, or interested in dancing. I was getting ready to leave when several females entered the gym. One was an attractive brunette, very tall with a nice figure. I hung around the refreshment counter watching to see what they were going to do, hoping for a chance to ask her to dance.

On the next song the band had played, she walked directly over to me, took my hand and led me to the dance floor. It was a slow song and she grabbed my hands, pulled me close to her, and we started to dance. It was another minute, when I realized she was leading, and I was doing the female part. I just danced with her, not saying anything. Three more dances, all slow numbers, she then returned me to the refreshment counter asking, “What are you drinking?” I responded, “A diet coke,” she left me returning with the drink, and then handed it to me.

She asked my name, what year I was in, did I live on campus, all the things that a guy would usually ask a girl. I was confused, I should be the one asking the questions, not the other way around. I dumbly answered her questions, not knowing how to handle her forwardness. I had never experienced anything like this before, not having any idea of what to do or say.

When I told her my name, she frowned then told me that Gigi is a much better name for me, the rest of the evening I was referred to as Gigi. From then on I was Gigi, that simple act confused me greatly.

Suddenly realizing, I never did get my game on as they say, just responding to her questions and desires. We danced quite a bit more that night, her always leading and me following. I never tried to reverse that, I am sure any normal male would have made the effort, but I just followed along.

As the dance was ending, she asked me to dinner, my nod the only communication of my acceptance of her invitation. We took her car, while leaving mine at the dance. I was taken to a burger joint a short distance from the dance location. It was frequented by a lot of the students, good food and reasonable prices. I was guided into the restaurant, with her hand on my back like a male would guide a female.

She pulled out my chair for me, and I sat down. She asked me what I wanted and ordered for me; while I sat there quiet and docile. I never questioned her, or even tried to order for myself. Our food was delivered, and she asked about my studies, did I have roommates, did I like my courses, again, just things that a male would normally ask a female on a date. Then, it hit me; she was treating me like a date, her date! So after three hours of dancing, eating out, all I knew about her was her name, Annabelle.

She had covered most of my life, my interests, my friends, everything and yet, I had no information about her other than her name. She paid the check, helped me up, and opened the door on her car for me again. Back to the dance venue, so I could pick up my car. Again, she got my door for me, then, the door of my car. I was leaning back against my car as she gave me a searing kiss. She took my cell phone from my pocket, and entered her number while noting mine. Another kiss, then, she helped me into my car. As I started my car, she told me, “Be ready Friday night for a movie and pizza, I’ll pick you up at your place.”

I drove off, bewildered, confused, and half conscious. Still in mild shock, I barely made it too my apartment, my nerves were shattered. I entered, going straight to my bedroom. While laying on my bed, staring at the ceiling, I tried to figure out, what the hell happened tonight? No revelations, my behavior was totally unlike me. I eventually fell asleep, my alarm waking me the next morning. I had some homework due today, so I got up showered, and dressed, then tried to get it done in time. I did manage to complete the assignment with only a few minutes to spare. While consumed with the assignment, I forgot all about last night, but after the last class of the day, it all came back to me in spades.

When troubled, I like to run, the exercise helping me to focus on important things. I ran for over an hour, the only thing accomplished, was I lost some weight as I sweated. Back to the apartment, a snack and more thinking. What happened last night was so unlike me. In previous dates with females, I was the aggressor, made the decisions and lead in any dancing. Shit, I realized I haven’t had any training in the female role in dance, how did I know what to do. Then, as I thought back, I hadn’t said ten words to her other than answering her questions of me.

Next day, more of the same, running for two hours, the same result nothing! I was barely able to concentrate in class, all of this craziness occupying space that should be used for my studies. Later that night, Annabelle called, telling me she would pick me up at seven, then, to the pizza place for a bite, with the movie starting at eight-thirty. I agreed, never voicing any of my thoughts or concerns for the last few days. It was like she had some control over my mind and body, everything I did, was as she wanted.

On Friday, I was able to concentrate on my classes some, but the date tonight was in the back of my mind. I cut my last class, wanting to get to my apartment, and get ready for my date. I wanted to look nice for her. As I entered the apartment, I made my way to the bathroom and started the water in the tub. I got out of my clothes, and slipped into the warm water. Having added some bath salts left there from the last occupant of the apartment, the water smelled nice. I soaked for a while, then got out and dried off.

I approached my closet, looking at the contents for something special for tonight. Finding a pair of pants, tighter than I like to wear them, but they made my legs and butt look good. The shirt was a silk shirt, a gift from my mother that I have never worn before. It seemed right for tonight somehow. It fit tight in the chest, with a scoop neckline. Mom swears it is a men’s shirt, but I have my doubts.

After I brushed my shoulder length locks, I decided to leave them down instead of my usual low ponytail. I checked my face, it felt smooth, my few whiskers deciding to stay hidden away. Finished, I grabbed my cell phone and keys, went outside and waited on the porch for her to drive up.

It was only a few minutes before she arrived, I walked out to the car, and waited for her to get my door for me. I sat down in the passenger seat and swung my legs into the car. As I did it, why I did it that way, flashed across my mind. I have never entered a car that way; that is how females do it. Then, I remembered that I had forgotten my wallet, no chance to change my mind tonight. If I did, no way for me to get home.

We drove to the bigger pizza place in town, the place obviously very busy. She got my door again and guided me into the restaurant. She held my chair, I gingerly set down in the chair and she pushed it in for me. I did notice quite a few eyes watching her get my chair for me.

She ordered the pizza and drinks, with me only nodding my approval of her choices. I only ate a couple of slices, my appetite not what it used to be anymore. I sipped at the drink with a straw, not wanting to get my silk shirt stained. The napkins came in handy, wiping the pizza sauce off my cheek before it could drip on my shirt. She paid the check, then we headed to the movie theater. She bought the tickets, then a popcorn and a diet drink for me. The tickets were for some chick flick, Annabelle insisting I would love the movie.

I was guided to some seats near the back, where she held my drink, as I set down. We nibbled on the popcorn as the trailers for future movies played on the big screen. I sipped on the diet drink occasionally, then, the feature movie started. I leaned my head over to Annabelle’s shoulder, letting it lay on her blouse. A quick glance at her chest showed slow and deep breaths. She leaned down to my face and kissed the tip of my nose, causing me to giggle nervously.

Instead of sitting up straight like a guy would, I wiggled a little, getting more comfortable on her shoulder. I stayed there for the entire movie, weeping in the appropriate places. I did sit up after the tear session, but she pulled my head back down, leaning her head against mine to encourage mine to stay there.

As we left the movie, I was draped on her, both my arms holding her arm close to me. I received several kisses, her instigating the kiss each time. Lots more looks from our fellow movie goers, I was aware of it, but did not let it bother me. As she drove me back home, I was again reminded of my obviously feminine behavior tonight. Nothing like this has ever happened to me, maybe it is a spell she has cast on me. Whatever it is, it has succeeded. She walked me to my door, another kiss, this one pure lust. I was trying to get my key in the door, but was not even close to the hole. She took my keys and opened the door for me, a small kiss on my eye and I was a goner. She walked back to her car and drove off. Like a lovesick idiot, I stood in the door, breathing hard with my eyes closed savoring the feeling of the kiss.

I did make it to my bedroom, slipped out of my clothes, falling head first on to the bed. I propped up my head with my arms, then folded my legs back toward my butt. Closed my eyes, replaying the events tonight in my head. I actually enjoyed the evening with her, the movie was okay, but being near her the fun part. I was treated like her girlfriend all evening, not once did I question the actions or how I was treated. She even told me that I smelled good, those few words sending lovely chills through my body.

Saturday, I lazed around the house, I never did much anyway, so it turned out to be a regular weekend day. At lunch time, I decided to improve my appearance some. A haircut, maybe even a color change, might just be what I needed to get out of my rut that I seemed to be in lately. I had a feeling that Annabelle might like it too, so I headed into town to see what I could get accomplished. The salon near the mall looked positively packed, so I went to a place I had seen in my travels, on the other side of the town. They looked crowded too, but there was empty chairs in this one. I walked up to reception, asking if I could get my hair colored and cut.

Sure, no problem, was the reply, and soon, a gorgeous technician came to get me. I was taken back to her station and sat in her chair. I explained what I might want and she listed my options that could be performed. Instead of a new color, she suggested highlights that would change my appearance without getting caught up in keeping my dyed locks roots from showing. I agreed as she held different colored swatches of hair up next to mine. I opted for the honey blonde highlights for my brunette hair, as she got right to work. Hair washed and conditioned, then a special conditioning treatment prior to the highlights being applied.

As my hair was separated into smaller sections, the dye was applied to the hair section and then wrapped in foil to keep it from dying the rest of my hair. I did look quite the sight with my hair full of foil pieces. Under a dryer for it to process, then back to the sink, so it could be washed out. Then, she asked what kind of cut I wanted. I had been looking through the hair style magazines as my highlights processed, and had several pages bookmarked. I showed her the ones I had picked, she asked me if I was sure. When I didn’t respond, she told me that any of the cuts would give me a quite feminine appearance. That is fine with her if that is what I wanted. I was quiet for a minute, then pointed to the style that I liked the most, for some reason it just screamed me.

Several minutes later, my hair was cut in that style, and she was using a blow dryer on warm and a pick to arrange my locks into the style. I was watching her intently, knowing that I would have to perform this function myself in the future. She asked if I wanted to try it myself, I quickly agreed. She wet my hair again and handed me the dryer and pick. It took me several attempts, but I managed to duplicate the style eventually myself.

I tipped her ten dollars, asking her if I need further help, if she could furnish it. She retrieved a price list of offered services along with a business card with her number on it. I leaned closer and gave her a hug, it just seemed the right thing to do. I paid up front and looked at the mirror near the front doors, a pretty female, at least from the head up was the image I saw. I smiled, can’t wait to see what Annabelle will think of my new look.

Well, if you are reading this story, you already know what Annabelle’s opinion will be. Yes, she loved my hairstyle, wanting to know when I was going to get my ears pierced. With that thought now firmly entrenched in my mind, it was only a few days later when I did get my ears pierced. Twice, studs in the top hole and a large hoop in the lower hole. I loved the feeling of the hoops as they brushed against my neck during the day.

The next weekend was a repeat of last weekend, only this time dinner was at a Chinese place just off the University campus. It was the first time I had eaten there, the food however was just short of fantastic. She insisted I eat with chopsticks, eventually feeding me bites during the meal. I was hopeless with the two little sticks, if it was up to me to feed myself I would have starved. Another movie followed the meal, this time an animated flick, cute and comical. I got assaulted in the car and then again when I got home. That is the second week in a row when she picked me up at my apartment, just as if I was the female in the relationship.

Tonight I was determined to ask her what is up, why she is treating me like a female. On the porch, after she had opened my door for me I managed the question. Her answer surprised me, “You are the female in this relationship, so what is the problem.” I just stood there, not having the slightest idea what to say in response. I got another kiss, this one while she was holding the sides of my face. When the kiss ended she had to steady me, I was swaying badly, the kiss affecting me that much. Another peck on the lips and she was gone.

All day Saturday I tried to figure out what is going on. I was being treated just like I was a female, but had no idea why. I was even helping the situation along getting my ears pierced and hair highlighted. Annabelle never asked me to do this, it was just something I should do when I am going with her. Now though my normal male persona was adrift, one look in the mirror and all you see is a female. I was never a jock, with narrow shoulders, and soft features on my face I was at best androgynous, now with the earrings and highlighted hair a female is the only logical conclusion you can come up with when looking at me.

The dating continued same as before, with me firmly in the role of a female being courted by her lover. I did start wearing makeup some, had my nails done and started wearing breast forms in my new bras that I purchased. Of course, panties to match, although I did not give in to buying and wearing a dress yet. I was taken out every weekend, even a few dates mid week. I received flowers several times and a box of candy for Valentines.

By now most of my fellow students presumed I was female, long highlighted hair, makeup, breast forms, and now high heels seemed to shout female to anyone close enough to me to hear. The high heels made my legs look so good, although I was not wearing dresses, the leggings I was now wearing looked so much better with my feet in heels. Annabelle was appreciative always complimenting me on my looks. I was getting kissed passionately every time she returned me to my apartment, The kisses were divine and so looked forward to.

At our six month anniversary I was asked to wear a dress, she was taking me to a very ritzy restaurant, legging or pants on a female not allowed by their dress code. The salon helped me find the perfect dress, and new underwear to make the dress fit appropriately. While there I had my hair styled differently, all in curls piled up on top of my head. A more dramatic makeup and nail extensions with a pink polish made the female presentation complete. I was nervous, hoping Annabelle would be impressed with my looks.

She picked me up in a limo, rented exclusively for this evening. The meal was delightful, my new corset hampering my appetite somewhat. An ice cream sundae for dessert covered in chocolate and cherries finished off the meal. Then she got down on her knees and presented a gorgeous engagement ring to me, sliding it on my finger while asking me to marry her. I of course, said yes, there is no other response possible with as much as I love her and want to take care of her.

It has been a slow trip to femininity, but one that I willing joined, my lover deserves a perfect female and I will try my best to be that for her. From that first dance it seemed we were meant for each other, with me as the designated female. So lets make it so.

© 2016 thru 2024 by Francesca

Debbie; Asking A Lot

Debbie; Asking A Lot

I am a recent addition to a work group, its sole function to court and sell a new customer our products. Our company manufactures different female products, from cosmetics to lingerie, and this retailer had withstood our best efforts to get them on board. So our company put together a select group of people with different skills to approach and try to land the customer. All were female except me, my field of expertise not often inhabited by females. I am the numbers person, supplying all matter of statistics to impress and influence sales of our products, yeah right.

There were three other members of the group, two sales specialists and one experienced in logistics, shipping and custom orders. When we met for the first time, I am welcomed into the group, like what I do would actually influence the courting of the customer. I wondered what I am doing here; these women knew the products backwards and forwards; there experience in handling special customers quite obvious.

Shauna and Beth were the sales specialists, and Katrina the shipping guru. When we had the first meeting of the group, all is explained to me, their detailed explanation making sense to me, somewhat. Jennifer McNeil is the name of our customer, running a multi-million dollar business composed mainly of three hundred retail stores. She has a reputation in the industry and has lived up to it apparently. She is strictly no-nonsense, once she takes a position, she never wavers.

The company wanted her business badly, the reason for this group is to try and sway her to becoming a customer of ours. To even get her to attend an upcoming convention we had to make lots of concessions. The convention is a regional women’s show where lots of companies rent space to show off their wares. We always rented large areas for our products, a good way to show everybody how diversified our company is.

We figured if we could get her to attend, we would have an advantage over the competition since we rented about a sixth of the display space available for our business. Then we could try and sway her with numbers and discounts to get her on board. Essentially we would meet her at her company’s headquarters, then fly her on our corporate jet to the convention, put her up in the convention hotel, then wine and dine her till we could get her signature on the dotted line. At least, that is the plan.

In several meetings before we left to get her, we went over every facet that she might visit, Shauna making sure that all of us are prepared to the hilt. One chance to make the sale, then failure if we messed it up. Beth mentioned some facts that they had found out from some of her previous encounters with the competition.

She liked to go to the extreme to force compliance, or give her a way to walk away from the proposal. One time she had told a salesman that in order for her to believe what he was saying she wanted him to disrobe right where he is standing, then stay naked during the rest of the sales meeting. He refused, and she walked out, not even accepting calls from that company anymore.

Another time she asked a female sales representative to remove her blouse to prove she is wearing her own product, her refusal ending the conversation immediately. Jennifer told her as she left that if the product you sell is not good enough for you to wear, how do you think I can sell it in my stores. The ladies in our sales group were dressed in the company’s clothes and using the company’s cosmetics. Hopefully, there would be no occurrences like that in our discussions with Jennifer.

We left in the corporate jet, chatting about our target and possible ways to influence her. Since Shauna is the most confident of the group she would be our boss in the negotiations, steering us in the proper way, hopefully, to get a signed contract. I estimated that her signature would generate sales of somewhere around ninety million dollars for our parent company. That figure made the project real important to the future of our company’s business.

When we reached her corporate headquarters, we had to wait as she was already in a meeting with some of her employees. When the meeting broke up, we were introduced to her; she shook each of our hands then handed me her purse, telling us we needed to get going. Immediately I was in shock, carrying her purse as we left her offices. Then I was handed her overnight bag, a cute smirk on her face.

The limo ride back to the airport is fairly short; she wanted to know what is planned for the three days, and when we would meet to discuss the deal. The trip was a non-event, a little business was talked about, but nothing more than that. We took a limo to the hotel and got everybody checked in. I smiled a little, she seemed to take pleasure keeping everybody off balance, never allowing them to get their game together. Shauna reacted well, when we get you settled in your hotel, we will have dinner and discuss what you would like to do for the three days of the show. Jennifer sported a little upturned lip; she saw us sidestep, well now we can see how much they truly want my business.

I stayed in the background, watching the back and forth between Shauna and Jennifer, a real exercise in gaining the upper hand. Every once in a while, I would catch Jennifer looking my way, but when she saw that I am watching her, she would return to her conversation with Shauna. We left to get ready for dinner, each of us had a room in the hotel also, to make sure we were available to meet with Jennifer whenever she desired. Shauna had made reservations at an Italian restaurant, known far and wide as a five-star plus facility. I watched from afar as the four gals made polite conversation during dinner, then almost bit off my tongue when Jennifer asked me a question.

She wanted to know what my part in all of this amounted to. I told her I am the number cruncher, supplying the figures needed to complete the deal. Then she surprised me by asking a flurry of questions about our product and its projected effect on her sales. I answered quickly and to the best of my knowledge, then as fast as it had started she turned to the others and I am ignored. No comment on the figures I supplied, nor where I obtained those figures.

The dinner wrapped up about two hours later, and we adjourned to our rooms. She wanted to meet early for breakfast and get an early start on the show. I dressed casually the next day, we had breakfast and then walked the show. She spent the necessary time in our booths observing the products we manufactured and the variety of our product.

The unusual part in all of this is that she had me carry her purse everywhere we went. No comments were made, when we would meet up she just handed me her purse and we went about our business. It bothered me at first, but since nothing was said about it, it became just another thing I was expected to do. There was never any more mention of my projections on her sales, so my presence in the group seemed not necessary.

We went to a small bistro, a block from the convention and ordered salads to eat. Jennifer is unusually quiet during the last of her lunch, and more than once I caught her looking at me, kind of sizing me up. Yesterday she looked away when I caught her looking, today she didn’t causing me to break eye contact. She asked if we could go to a private room to discuss a request of hers. Shauna is smiling, hoping that we now had a deal. We went back to the convention center and used one of the meeting rooms they supplied for businesses. We all set down, and Jennifer cleared her throat, then started the dialogue.

“I have a proposition to make to your company, it is a test of sorts to see if your products are as good as you say; it is also a test of your personal commitment to the company and your products. You have until the convention ends to accomplish this task, hopefully to my standards. It will take all of you to accomplish this, your teamwork and your commitment to your company will be tested. I will sign a five-year contract with your company for all of your lines, and put them in all of my stores; I am sure David can supply the amount of money this is worth to your business. In exchange, I want David turned into a female from the skin out using your products mainly, the more you utilize, the more favorable I will be to signing.”

Shauna and Beth had inhaled sharply, none of us saw this coming, pure shock on everyone’s face. Katrina was trying to keep her composure while her mouth remained wide open. There was a little smirk on her face though. I just sat there numb now, not able to get a single thought out of my brain, panic slowly rising and making itself known.

Jennifer suggested that their first action would be to ensure that I would participate in this. “I am sure he being a male, might make his participation less than enthusiastic. I remind you that I will accept no one other than David. Although he is obviously a male, his appearance could be changed to that of a female with some talented help. If the job is thorough enough, I will sign, but I am looking for 100% female, not any half hazard attempt to fool me. I will be making a detailed inspection of her when she is ready, providing you can get David to participate in the first place.”

“I am sure you have checked me out enough to know that I do some odd things from time to time, but I think I have exceeded myself with this project. If done as I wish it will show me your companies and your individual commitment to your products. Incidentally, the unveiling of your masterpiece will be at my office the exact time that the convention closes two days from now.

Now I think I have my fun for the day; I will bid you adieu and hope to see David two days from now. My own company plane has just landed so I will fly back and look forward to David’s and my meeting in a few days. He is to arrive by himself with the contracts, and after my evaluation, I will discuss the contracts with her. If all is in order, I will sign, even making a sizable deposit on the first orders.”

She got up from the conference table and walked out. Shauna is the first one to get over the shock, looked at me then smiled. She got her cell phone out and was calling corporate a few seconds later. She had to wait for quite some time to be able to talk to our CEO, Beverly a longtime friend of both Shauna and Beth. They talked a while, then Shauna is writing some figures down on a tablet. She broke off the call, then asked Beth and Katrina to start planning my transformation if I agreed to the project. She sent them to their rooms and dragged me to hers.

She set me in a chair next to a love seat grouping in the corner of the room. She set on the love seat and stared into my eyes. She asked if I had any idea that Jennifer would pull this stunt. I could only tell her of the numerous times I caught her looking at me, and how today she would not look away when I caught her staring. She asked me my thoughts on what she has proposed. I told her that I am still in shock, but I didn’t want to be turned into a female just to keep my job or land a contract.

She understood that, she didn’t think many males would be interested in the deal with those conditions. She wanted to know what it would take for me to agree to help. I didn’t want to commit myself, then find out they had in mind more, so I turned it around on her. I also wanted to know how far the transformation would go, from her perception of what Jennifer wanted. Shauna thought it would be all the way other than the actual removal of my penis. The more realistic the image, the better the chances of the deal going through. Well that certainly upset my being both physically and mentally. My stomach rumbled a little, too much unsettling info to deal with.

I took in a huge breath, doing everything I could to keep from fainting. I am not sure if it was the words ‘all the way’ or ‘removal of my penis’ that caused my concern, but either group of words had captured my undivided attention.

Shauna wrote a figure down on the pad she held then slid it over to me. My eyes almost bugged out when I saw the figure; then my mind started to realize all of the possible ways this could go wrong. How long will the changes be with me, can they be removed quickly or will I be stuck with some of them for a while, or worse just stuck with them permanently. I slid the pad back, I am not interested, they are way too many things that could go wrong, and my life is not worth that little. She smiled then jotted another figure down, this time, a percent figure.

I looked at her straight in the eyes and asked what the percent figure is in reference to. “It is the percentage of the sale if you get her to sign, if the deal falls through you get a quarter million just for doing it. If you want your job back, that is assured but at a higher level. We don’t have much time, so take an hour and think it through, then let me know what you decide.

I wish I could tell you more, but this has surprised everyone, and we are all scrambling just trying to figure out what can be done and how it can be accomplished. I personally hope you will try it, but I fully understand if you are not interested, there is so much at stake here, no one can really appreciate all of the ramifications of this proposal. Jennifer has exceeded her reputation; this is one shocking proposal that will have far ranging effects for lots of people starting with you.”

I returned to my room, laid on the bed and almost cried. In the past, I have hit things when I have been super frustrated, but this exceeded all of those times by a mile. A few tears leaked from my eyes, but I managed to keep control. Why me is the first thought, I suppose since I am part of the group, I got chosen simply because of my availability. Then the realization of what could be thrust on me in the next few hours, some of it known, the rest being thought of now, as the girl’s tried to figure out a way to meet Jennifer’s request.

The hour is soon up, and I returned to her room. She answered the door quickly looking at me to see if she could detect what I had decided. It told her that I would do it, I am sure what little brain matter I had is draining out of me as I speak. I did ask for lots of help, in what to do if I made it as far as her inspection, my sales ability a negative figure and I am sure my mode of dress at the time will not make things any easier for me.

She called the other two in, and a schedule is quickly put together for the next two days, actually a day and a half since I would have to fly to her corporate headquarters for the inspection and contract discussions and possible signing.

I didn’t have a lot of faith in either the transformation or my ability to close the deal, but I knew I had to try, why I got picked to be the chosen one baffled me. I didn’t think she hated me, but why me? After my schedule is written down, Beth grabs my hand and leads me down to the convention floor. We walk right over to the Turnabout Gurl Salon’s booth, and I am escorted to a chair at the back of the booth. They have been a customer of ours for years, in fact, most of the time we ship more to them than to any other customer.

Stephanie, one of their stylists, gets me on a table and quickly removes all but my shorts. There is a privacy screen between the other convention goers and me, but the background noise makes it seem like I am naked in the middle of the crowd. She explains to get me transformed in time they need to do it here on the convention floor.

I am laid back, and she applies a cream to my front side not missing any areas, my beard area, and my eyebrows get included. While they are waiting for the cream to do its job, my ears are pierced twice, with a pair of studs and hoops inserted in the new holes. She then starts working on my hands, filing my nails into ovals and pushing back my cuticles. I didn’t even know I had cuticles until she started removing them. When both hands were completed, she glued on extensions to each fingernail that she had carefully picked out to match the width of my original nails. After each hand is finished, she placed them in a light box glowing with a purple light, to set the adhesive and make the nail appear natural.

The cream on my body is removed and with it all of my body hair. I never had a lot there before, mainly my legs and my arms, but now I had none, at least on the front side. The cream is still on my beard area and my eyebrows, as she started on my feet. The same filing into slight ovals, but thankfully no extensions are used.

I have never dressed as a female before, heck I seldom even watched a female dress or do her nails or makeup, so this is all foreign to me. The sensations are pleasant, but not in a sexual way. When she finishes my feet, she then removes the cream on my face leaving my face silky smooth with not even a shadow where my beard had been before. Of course, my eyebrows had vanished too, the impact of them being removed really making a difference in my looks. My distinct forehead less obvious now, with my hairline seemingly lower than before.

I am turned over, my backside receiving the same cream and hair removal. As in when she did my front she had moved my shorts out of the way to ensure that no hair is left unattended to, a few minutes later she removed them completely. Finally, finished with the hair removal, I am on my back when she pulls out some stirrups at the end of the table and places a foot in each. She attached a strap to each foot to keep them secure, then spreads the stirrups so that she has access to my groin area.

After I had figured out what she might be doing, I realized the degree that I would be subjected in this feminization effort. An hour later my male member is no longer visible, only a slit surrounded with two puffy lips are visible, my bottom half now female in looks.

I knew my mind had not kept up with the changes, now I am half female especially the part that usually defined the female sex, although my overall appearance is now leaning to the female side there is still a masculine edge there. Sooner or later there will be a defining moment when my mind realizes what has happened, and sheer panic will set in. I could hardly talk to a female without freezing up, and now I am one in looks, things can’t get much worse or can they.

My concentration wandered off again as a large machine is wheeled in next to me. Two cups are lowered to my chest, then positioned above my nipples. The cups are glued to my chest then the hoses attached to the cups. A fatty substance is added to the cups and then the machine is turned on, and slowly the extra tissue on my chest is pulled into the cups by the vacuum pump. From the size of the cups, I will not be short on breast material, if the cups end up being filled. The cups are hooked to the pump by hoses running from the cups to the machine. After the cups are about a fourth full, the pump goes to alternating cycles, pumping then off, then repeat the sequence. The whole apparatus warms up, the liquid that had been injected in the cups seems to be absorbed into the skin. The tissue in the forms stayed where it is at, the vacuum pressure never releasing.

While this is going on, two stylists were adding long strands of hair to my own hair, although the new hair color seems to be slightly lighter in color. I could feel the weight of my new hair pulling on my head, something to get used to. Then I thought about my breasts, and the lack of anything between my thighs, a lot more to get used to I am sure. Four hours later they seemed to be done with my hair and the cups on my chest now almost full with breast tissue. The convention is winding down, fewer people in the hall, the noise level greatly decreasing. The machine is turned off, I found out that the cups will remain dissolving slowly over the next day or two. They already were somewhat more flexible than from their original rigid form. I was told that the machine that created my breasts had been brought to the convention specifically for me.

I sat there contemplating what is happening, a fairly normal male employed by a corporation doing the best that I could do in my job. Then all hell broke loose, Jennifer to be exact, and now I am sitting on the convention floor, with a female vagina, large breasts, manicured nails, hair free body, and on a collision course with extreme femininity, at least, to me it is extreme. When and if my body realizes what has been done to it, I am sure there will be screaming and overall panic, but for some reason, that scenario has not happened as of yet.

My hair is put in a braid, and I am given a bra and panties to slip on. The bra feels good, especially the support it provides. The panties look good, but the feeling of something missing down there is unnerving. I get a lavender sweat suit to wear, and I am hustled upstairs to my room. Shauna and Beth are waiting for me along with another lady that I do not recognize. She looks familiar, then all of a sudden I recognize Francine, her picture on most of the Turnabout Gurl Salon’s signs and promotional material. I sat next to her on a love seat, and she starts the conversation. Shauna and Beth leaving the room, with only myself and Francine still in attendance.

She asks about me, did I enjoy the treatments today, and am I looking forward to tomorrow. I tell her that I am okay, the shock and panic have not settled in yet, but I am sure it will eventually catch up with me. We talk for quite a while, as she finds out how I have ended up in this situation. My job prior to this most recent event, receiving quite a bit of attention. Francine is easy to talk to, and an excellent listener.

“Have you done any plays or drama in school?” Francine smiled as I contemplated an answer. “I participated in a play in grade school, but it was ages ago. The part was only a few lines, but I managed to pull it off.” I don’t think that experience will help me through this, that play had me cast as a woodland creature, somehow portraying a female is a little more complex than that character.

“That is what you are doing tomorrow, a part in a play that requires you to be in costume. You are playing a part of a successful female in a large corporation that is seeking to win a large and lucrative contract. You have a good looking body, great hair, and you are confident in your knowledge and leadership. Once we do your hair and makeup and you are dressed in some beautiful feminine clothes the world is yours simply by you claiming it. You will meet your new client, impress her with your knowledge and salesmanship, and then get her to sign on the dotted line. This you can handle with ease, a female, proud and self-assured in herself.”

As we talk a little more, I express my doubt in doing any of this, my fear of fouling all of this up, I am not a salesman, just a pencil pusher in a large corporation. She smiles, did you not hear what I said, believe in it and I think you will do quite well. In fact, while you are flying back from your meeting give me a call and let's discuss how you did, okay. She kissed my cheek, hugged me tightly and then left.

I moved to my bed, leaned back and am soon asleep. Let me tell you about going to sleep in a female body. The long hair braid at the back of my head was the first obstacle. The two breasts that were swinging around wildly were the next problem to overcome. I used to lay on my stomach that seemed to be not an option anymore, I tried to lay that way for a minute, but they felt very uncomfortable in that position. I finally settled on laying on my side, once I managed to keep my breast from sliding under me. The braid felt better that way, the fact that I didn’t have to lay on it the main reason.

I wish I had half of the confidence other people have in me; maybe it is possible, but can I pull it off, that is the question. For some reason those words of Francine’s did stay with me that night, I dreamed of being that self-confident female making my way through the business world, my two sizable breasts leading the way.

The next morning, I slipped out from my sheets, then made my way to the bathroom. I noticed the reflection in the mirror as I entered but only after I set to pee did I notice my clothing and my looks. I wiped, then stood up and took in the image again. No comment on peeing as a female, it was messy though. An attractive female returned the look, dressed in an ivory lace nightie, and matching robe. I don’t remember going to bed this way; I presume one of the girls had something to do with my choice of something to wear to bed. I slipped the nightie off and then took a shower; it felt good, the water pulsating off my body made me feel energetic. It also did other things to my new body, so I bit my lip and tried to end the shower as soon as possible.

For some reason, I instinctively kept my hair dry, then blotted my skin with a towel after emerging from the shower. I wrapped the towel around my breasts, like I have seen many women do in the movies then made my way to the bedroom. I just referred to the objects on my chest as my breasts, what a bizarre thought, maybe after all of this is over I might do well to schedule an appointment with a mental health professional, providing it is not too late.

When I got back to my bed, I noticed another set of sweats, plus a bra and panties there, so I put on the bra, then wiggled into the panties followed by the sweats. The bra did require some contortions, but eventually it was secured around my chest. The hair is still in the braid, although strands of it are attempting to escape. The image in the mirror is female, of that, there is no doubt. Maybe I can do this, I just have to finish convincing myself of the possibility.

I picked up my room key and then made my way downstairs. I stopped at the restaurant and ordered a roll and some Orange Juice. I then made my way to the convention floor, and back to the Salon’s booth. Stephanie is waiting for me, so I plopped my butt down in the chair, finished my roll, and told her let’s get on with it. She smiled, “Francine must have given you a pep talk last night, confident and self-assured I presume.” I nodded my head, “now you have to make me beautiful, then I will be off to do battle in the corporate trenches. A prayer would be appreciated, maybe two if you can spare the time.”

Both of the girls came rushing up to me, short of breath wanting to know where I had been. I pointed to the chair, here. They broke out in laughter, then started asking lots of questions. I told them to leave Stephanie and me alone; we will handle my looks; you get everything ready for my presentation, and I will see you around eleven. Now get.

Shauna, in particular, smiled, this is a side of David we haven’t seen. Well duh, the reason that you haven’t seen this side of him is that I am not David, my name is Debbie, and I am on a mission. Now get.

Giggling can be heard as they left, I just hope I can keep the confidence to handle Jennifer in the same way. Speaking of keeping the confidence, I had no idea where that confidence came from. I remembered the talk Francine had with me, I think, but I have never been confident in anything I had ever done or attempted to do in my past life. Hell, I am an employee trained in producing numbers for the corporation, not some super sales woman attempting to close a multi-million dollar deal. There is that word again, woman, I may look like one, but acting like one, we will have to see.

Makeup is applied, and instructions are given for repairing mascara and lipstick. My hair is set in curlers, and I get to experience time under a hot dryer in my quest to be beautiful. The curlers are removed, and a curly hair style now frames my face as she sprays it with hair spray to hold the look. I get a few lessons in recreating the look, and then instructions for a ponytail if all else fails. Of course, just like the girls everything I am wearing comes from our company.

Then I am moved to another room, where a lot of clothes are hanging on racks around the room. My bra is removed and replaced with a corset, with cups that support my breasts. The corset is tightened several times over the next hour as stockings are eased up my legs and heels are slipped on my feet. I almost lost it when the stockings were slid up my leg, they felt so delicious, sending all kinds of feelings to every part of my body. Three-inch heels now adorn my feet, making me look imposing.

Finally, the ivory business suit with a pencil skirt is slipped on, the suit jacket having a low cut neckline to accent my cleavage. The tan lacy blouse helped cover my breasts, but seemed to only draw more attention to the low cut suit jacket. I hugged my miracle workers and complimented them on their work. Then I turned this way, and that as I am admiring my image in the mirror before I walk out the door and up to my room.

In my room, I find my briefcase on a table, checking its contents I find most of what I might need. The contracts are there, along with some notepads and some pens, the file on Jennifer is in there also, in case I need to refer to it. Next to it, on the table, is my purse, opening it I see the rest of my things, along with lipstick, mascara, a hair brush, and some face powder. Then in another compartment some tissue and some tampons, I presume those items make me appear authentic right down to the last detail. I leave my room, looking for Shauna. She is coming out of the elevator and walks right past me.

I turn around and follow her for a minute or two then when she is in a line to enter the convention I ring her on my cell. When she answers, I tell her to turn around and say hello to Debbie. She is stunned by my appearance, I turned out much more attractive than she envisioned. We talk for a few minutes then I tell her I have to get going, I want to arrive early for my meeting with Jennifer. A company limo is outside waiting for me courtesy of Katrina. I got a good luck hug from Shauna as the limo headed for the airport.

Talk about being nervous; I am scared to death. It is one thing to be portraying a female, but doing that and attempting to close a business deal at the same time is highly stressful. The plane is waiting and as soon as I am on board and seated it moves down the runway to get airborne. The flight is pleasant although it seems to take forever to get there. I go over in my head all that I need to do to ensure a successful outcome of this meeting. The female part is most convincing, everything realistic including my vagina. I even practice my female voice a little, my male voice never very strong, now I find out that by talking a little softer and more breathlessly I sound somewhat female. Now if I can keep her off balance, maybe I can secure a deal before she gets her game on.

Jennifer’s limo is waiting for me at the airport, and the short drive to her corporate headquarters is done in record time. I made my way into their headquarters, then up to their executive offices. I check in with their receptionist and am shown to her office. I take a deep breath and enter the office. Let the games begin.

I walk right up to her desk and offer my hand. Her mouth is open as I shake her hand, then I promptly sit down and open my briefcase. I remove the contracts laying them in front of her and suggest that she review them before she signs. I asked how business is, and tell her I think she will be pleasantly surprised with her sales, once our lines are added in her stores. I sit down on the chair in front of her desk, then stare at her, my legs crossed at the knees. Her mouth is still open, and her speech is severally impaired. I did hear the word David somewhere in that vast silence that permeated the air.

“David couldn’t make it; he is indisposed right now. My name is Debbie, here to accomplish only one thing and that is to get your signature on the contracts in front of you. While we are discussing business, are you aware of how much our cosmetic line could impact your lackluster sales in that area?” I had only made a guess there; I had nothing to back it up. Since she is still quiet, I must have hit on something. I rattled off some figures based on some of my projections, then continued with figures on our lingerie line. Somewhere during that time her mouth finally closed, and a smile appeared on her face. By the time I had finished my spiel, her smile seemed to encompass her entire face, looking more like a smirk than a smile.

We sat in silence for a couple of minutes, then she got out of her chair and approached me. She took my hand and dragged me to her love seat, her next question surprising me. “How do I know that you are truly David and not some impostor trying to get my business?”

“You don’t, and I am not going to tell you. Now are we going to discuss business or do I need to call the airport and get my plane ready to fly back?” We had a stare down, for several minutes, then she is the one to break first. “I am impressed, not only your looks but the total change in you. Confident, self-assured, not anything like the David I met yesterday.”

That made me think, I have changed, and I can only blame it on my transformation. Nothing else has changed since yesterday; I do feel more confident dressed as a female, feeling that I can move mountains. The best example of that is me standing in Jennifer’s office, telling her to either get down to business or I am flying back. I don’t think even Shauna is that confident in herself.

I should have been ready for another Jennifer surprise; I have let her have too much time to gather her thoughts and make plans. “Before we get down to discussing contracts let’s get something to eat. I know a nice quaint Mexican place, excellent food, private booths, and they even have entertainment. We can learn a little more about each other and enjoy some good food.”

I agreed, but asked if what I had on is proper dress for the restaurant; I imagined any place that Jennifer ate at was more than just a quaint little place. She told me not to worry; we could stop along the way and pick me up something to wear. I raised my eyebrow but agreed to her proposal.

Big mistake. I took my briefcase, along with my purse and we left her office in her limo. Twenty minutes later we pulled into a boutique that screamed ritzy and made our way inside. Jennifer is greeted by name, and we are led to the back fitting area. Next to where we are seated is a rack of dresses, I presume picked out for her to try on.

Jennifer had me look through them and pick out anything I might like. Then with a twinkle in her eye, she told me she could pick out the one that I would find fascinating without even looking. Another raised eyebrow from me, then she went to the other side of the dress rack and marked the one that I would pick. As I was looking through the dresses, she told me that if she is right, I would have to wear a dress that she picked out for me as her reward.

Most of the dresses on the rack looked middle of the road, so I felt safe and agreed. After looking through the rack, I pulled out the one that interested me the most. I have been exposed to women’s clothes for less than twenty-four hours, and here I am picking out a dress, go figure. When I turned the dress around there is a tag on it saying Jennifer’s choice. I quickly go to the other side of the rack to see if all the dresses had the same tag on them. Jennifer smiles, “you don’t trust me do you?”

Since she had predicted the dress I would pick, I had to wear her choice for me. The dress she wants me to wear can be only described in one word, scandalous. She leads me to a changing room and pushes me and the dress inside, then asks if I might need assistance in putting it on. I decline, but it took me twenty minutes to get into the dress alone, even then the zipper is not up, and I had to hold the front of the dress to keep my breasts covered. The dress barely covered the cups of my corset, the tops of my breasts peaking over the neckline of the dress. I felt almost naked, some of my confidence slipping away.

I knew I had to recover my confidence, this dress not doing anything to help with that. I felt like I am on display, the skirt is extremely short, the coverage of my breasts almost non-existent. The color of the dress is a bright red; no one will miss seeing me in this sexy concoction. Of course, I had to have appropriate shoes; the five-inch stilettos made my legs look good but hindered my walking quite a bit.

The only thought that kept running through my mind is look at the mess that you have got us into now, you might seem confident, but this dress certainly levels the playing field. This all taking place in my head, my male self-trying to reason with the Debbie persona. I gingerly stepped out of the dressing room and made my way to the mirror right outside. Jennifer stepped up and zipped up my dress for me, then leaned in and hugged me. The feelings that were inspired by that hug should be labeled lethal, the goose pimples that sprouted next almost caused me to faint. Jennifer helped me to a sofa nearby and eased me down into the soft cushions.

She told me to relax, while she tried on her dress, then we would head to the restaurant. I looked in my purse for my phone, noticing that I had several calls from the girls, probably wanting to know where I was and if I had made any progress. I kept the phone set to mute; I didn’t need anything else compounding my thoughts until this situation is resolved.

By the way, how do you resolve a situation like this, I had a bad feeling that there is now something between us other than business dealings, and I didn’t have any idea how to handle it, I am still having trouble handling the business end of it, much less anything else. If there is some attraction between us, how do I respond to her advances? I am not sure what I feel for Jennifer, she is attractive, very personable when alone and she does fascinate me. I guess there is some attraction on my part, but with my past history, I probably wouldn’t recognize it if it hit me over the head.

There is a reason that I am still unmarried at the age of twenty-six, my last date is while I was enrolled in college, not really a date, just some girl needing someone safe to go to a wedding with. I can hardly talk with a female, without freezing up, the words just don’t make it past my lips. When Jennifer first asked me those questions in that meeting I almost froze solid then, only a slight smile from her allowing me to continue.

Then there is the dress that I am wearing. The fabric so soft, yet sensual, the material hugging my body, especially my breasts. When the salon first created them, it was a shock, but the reality had not set in. Now that some time had passed, my breasts were constantly sending messages to my brain about the situation down there. My nipples pushing against the material of the dress, the thin corset cup barely able to insulate the nipple from the sensuous material. Any movement on my part, just making the situation worse.

Then you have to consider my new vagina, my penis now concealed, leaving a void down there that is far from innocent. The panties I wore seeming to make the situation worse, the slippery nylon material of the panty sliding over my new vagina, sending little jolts of electricity throughout my body. I never asked, but I wonder how a false vagina could be registering and sending touches and movements of my panties against my bare skin. When I overthink my mind shuts down, all of these unanswered questions put aside for a later time.

Jennifer soon appears in a dress that is very similar to mine, only in a pale green color. Her endowments are obvious to anyone’s eyes, the cleavage just as enticing as mine is. I had looked down at mine after seeing her in the dress, comparing the two of us, she seemed to be more fortified than me, a pang of jealousy nagging at my brain. I had to think some pure thoughts, me a male being jealous of a woman’s more spectacular cleavage, what the hell is wrong with me.

Before I could figure a proper response to her looks, I am being led out to the limo. We are helped into the back seat and headed to the restaurant. Upon our arrival, we are shown to a private dining room, composed of only a few tables, the one we are seated at, had a breathtaking view of the river below. The restaurant built on a hill overlooking the river, this particular dining room seemed to be hanging over the river with little or no support.

We never received menus; Jennifer had apparently already ordered for us before we arrived. The meal is excellent, both of us receiving chicken fajitas with numerous accompaniments on the side to adorn them with. The guacamole and spiced tomato sauce are especially good. We are served Sopaipillas for dessert, biting off a corner and filling them with honey made them a delicious special treat.

The conversation at the restaurant very light and steering clear of anything regarding our business deal. She gave me a little of her history and her rise to CEO of her company. She seems extremely driven if any of her exploits are true. She wanted to know a little about me, what I enjoyed and how I ended up crunching numbers for a living.

I retold the story of how in college, I never did well in any subject other than math, statistics in particular. When I graduated a friend of my math teacher working for this company told him that he was looking for a statistician, the company getting big enough to require someone in such a position. I interviewed and was given the job just three weeks later. I rarely left my office, all of my involvement with the company being handled by email. When I was selected for this job, it was quite a shock, I am obviously in over my head, not just as a female, but also as anything other than a number cruncher.

Jennifer suggested that we go to her home, talk a little more about the contract, and then get some sleep. She promised me a safe and friendly environment, since it is getting so late, a trip back home tonight would be hard on me. I reluctantly agreed, and as the limo arrived, we then made our way to her home.

To say she lives the life of some influential corporate CEO, a misconception after looking at her home. It is nice, a sprawling ranch house nestled on several acres of land. Not pretentious, not even a separate garage for the limo. The driver got our doors, and she showed me around the house. I am assigned a bedroom at the end of the hall, beautifully decorated with a spacious walk in closet. She told me there is some nightwear that should fit me in the dresser and a robe in the closet for me to slip over the nightwear.

She suggested that we meet again in her den when ready, and we could sip some wine as we discussed business. After slipping out of the dress, I found a nightie, silky and lacy it did cover all pertinent areas. Getting out of the dress was a chore, I don’t think my arms will ever be able to contort to the positions that a female normally uses in her dressing and undressing.

I decided the corset stayed on, another layer between myself and Jennifer. The robe apparently matched, giving me a more modest appearance. I took a minute to send a text to Shauna, letting her know that I am still working on Jennifer, no signature yet, but I have still have hope. No idea on when I will be back in town, not everything going according to plan in this scenario. I turned off my phone; I really didn’t want a response to that text, fearful of answering any more questions that I am sure would be asked.

We did discuss business, she agreed to sign on the dotted line but wanted more time with me before she did the deed. When she saw me trying to stifle a yawn, she knew it was past my bedtime. She escorted me to my bedroom, then pushed me up against the wall and kissed me passionately. As fast as it had happened it ended and she told me we would resume negotiations at breakfast in the morning. There was a slight giggle and a smirk as she left me in the hall. I wandered into the room, removed my robe and fell into bed. Later, I had to get up and do the bathroom thing, but that was a nonevent and I am soon back asleep in the overly comfortable bed.

The next morning is unreal, my hair is tussled, my makeup is smeared, and my nipples are hard and erect. I panicked, not really knowing how to handle any of these problems. There is a knock on the door and a lady dressed in a maid’s outfit asks if she can help. Before I could respond she explained that Jennifer had explained the situation and thought that I might need a little help in making myself presentable. I stood aside and let her in, not comfortable with this, but the situation without her help would be much worse.

She sat me down at a vanity, put up my hair in a bun, then a shower cap to keep it dry. She handed me some makeup wipes and told me how to use them. She suggested a shower after the wipes, then she would pick me something to wear today. A look of distress came over me, I had not brought any clothes to wear today, figuring that the one day would be enough to handle any business. She scooted me off to the shower, telling me not to worry, everything is all right.

The shower is excellent, the pulsating jets almost making me wilt. I did manage to escape before I turned into goo, but barely. As I left the bathroom, Marie, her maid, had laid some clothes on my bed to put on. My other clothes had vanished so I had no other choice. I managed, although it took me quite some time to get covered up. It seemed at whatever I tried to put on turned me on, my nipples rock hard the whole time. Marie entered later, smiling at my appearance and telling me to sit at the vanity. She styled my hair, then helped me with my makeup, the items not in my purse she somehow had access to.

I wandered towards the kitchen, Jennifer intercepting me at the dining room. There were a few covered dishes present holding our breakfast. The food is excellent, and I was quickly too full since Marie had helped to refasten my corset making breathing and eating two subjects to be done only in moderation. I knew I had lost the self-assured part of my impersonation, so I asked Jennifer where we go from here.

She had again gained control of the situation, her shock from yesterday now a thing of the past. She suggested that we tour her company, letting me know a little more about her as a customer. I agreed and soon we were headed to one of her stores in her limo. At least with us visiting some of her stores, the possible relationship with Jennifer wouldn’t get any more exposure.

We did more than just walk through, I am introduced to some of her people and invited to ask questions. After the first two, I loosened up a little, asking some pertinent questions about their job and what they did. This continued for several hours as we visited three stores and one of their distribution warehouses. Here in this environment, Jennifer acted different, no longer the pushy CEO she treated her people like friends, real good friends. Quite often her conversation is about their families, their kids and if someone that was sick had recovered. We ate at a little diner, very unpretentious, but excellent food and a delightful atmosphere.

I had noticed that during the day, my attitude had changed, a little of the self-assuredness returning, but a sense of caring going along with it. I never once thought about the contract, about getting her signature, just enjoying my time with a friend and learning about her business. After lunch I remembered my job and told her that I needed to call my company and report my inability to get the contract signed. She told me we were heading back to her corporate headquarters and I could make the call there.

After arriving we went up to her office and she got on the phone. I soon discovered she had called Shauna, Jennifer telling her that she needed to talk with her boss about some aspects of the deal that still needed to be worked out. She had put it on speaker phone so that both sides of the conversation could be heard. I sighed, my inability to get her signature now a sure thing. I would travel back tonight, face the music tomorrow and then resign from the company. After a five minute wait our CEO got on the phone and asked what she could do for her. I kind of tuned the conversation out, I was aware of my failure, I didn’t need to be reminded of all the ways that I failed. Finally Jennifer handed the phone to me and I said hi, yeah a great way to start the conversation.

It turned out to be Shauna, asking how I am doing. I am alright, as soon as this is over I am going to head back. Thanks for having some faith in me, I am sorry for failing you. She giggled at me. “When you hang up you need to ask Jennifer to explain to you what just happened, listen carefully to every word she says. Then later tonight you need to call me so that I can talk to you intelligently, not this one sided conversation we have going on now. Thanks for all you have done, I don’t know how you pulled it off, but a lot of people owe you quite a bit.” The line went dead, I didn’t have a clue what she meant.

I looked over at Jennifer, the look that she saw on my face made her chuckle. “Let me guess. You would like to know what is going on, you have conveniently zoned out on me, your body is here but that is all. I have talked with your CEO and I have agreed to a ten year contract with your company for your products. I have made a few demands though before the deal can be put to bed. Your company has agreed to their part, now everything else depends on your agreeing to the deal.

Since you have obviously not been listening, I am going to make you wait a little longer. We will head to my home and after getting dressed properly you will go out with me tonight for dinner and dancing. During the evening I will explain all to you and when we return to my house tonight I will ask for your decision.”

She leaned over and kissed me on the lips, leaving me breathless and confused, so very confused. I am led to her limo for the short ride to her house. As we enter Marie meets me at the door, and I am led back to my room. As we enter I see two other females waiting for me, with lots of things laid out on the bed and vanity.

It turns out the ladies are from the local Turnabout Gurl Salon and they are here to make me pretty again. I am undressed and sat in a chair while they start on me. My nails are worked on, the extensions taken off and longer ones applied. This time a bright coral polish is applied, then my feet are handled in a similar manner.

My hair is set in curlers, and a portable dryer is put over them. Forty minutes later the dryer is removed followed by the curlers. Makeup is next, all of my old makeup is removed, and then individual false eyelashes are applied making my eyes look as if they are peeking out of a forest of lashes. My earrings are changed, long dangly chandelier earrings are put in the lower hole, with diamond studs in the upper hole.

Then a lot more makeup, with much more dramatic colors are applied to my face. I almost didn’t recognize me, the look very different from the business professional look of the last two days.

As the technicians fuss with my hair, I reflect back on my recent experience with femininity. It still feels strange, but not distasteful. The way people see me is so different, I feel for once that I can contribute to life some, instead of just going along for the ride. Jennifer still worries me a lot, her interest in me is scary, she sees something in me that peeks her interest, and her pursuit of that something seems relentless. Twice she has taken me to a fancy dinner, like she is courting a loving partner. I do have feelings for her, but am afraid to admit to them. All day today, I saw a different side of Jennifer, one that she doesn’t let out often, and one that her employees adore. I think I am in love too, with that same loving, caring person.

The image in the mirror brings me back to earth with a thud, a very sexy female, ready to take on the world. My hair is piled on top of my head with tendrils of my hair and ribbons escaping from the up do, and cascading down around my neck and ears. The effect is very feminine, but my hair and those ribbons rubbing my ears and neck are driving me crazy.

Marie helps me into the dress, if you could call that skimpy piece of material a dress. It covered much less than last night, I almost feel that my corset covers more than the dress accomplishes. The tops of my breasts are peeking from the top of the dress, actually only a few pieces of lace at the top of the bodice. The hem only a few inches below the bottom of the corset and relatively snug around my thighs. I gave a funny look at Marie, asking if she had another dress that actually covers some of my body. She smiled, telling me that Jennifer will love the dress and the person that is in it.

That is what I am afraid of, the technicians add another layer of lipstick to their masterpiece and they are off. I wondered what their services cost, I am sure it is not cheap. I am also curious as to who paid their fees, there seemed to be only one suspect, but she is not volunteering any information.

A few minutes later she comes to collect me, kissing me firmly on the lips as a greeting. I walk along, the towering heels making the walk a little difficult. The kiss has sent my mind into lock down, not a rational thought possible at this time. The limo is waiting for us, I am helped in and we head off in a different direction away from town. An hour later, we arrive at our apparent destination. The restaurant is very upscale, the cars I see in the parking lot all foreign luxury cars. The valet gets our doors and then the main door for the restaurant.

Jennifer is apparently known to the Maitre’D, as we are quickly led to a private dining room on the second floor of this establishment. A window overlooks the floor below, a dance floor situated right in the middle of the first floor, with tables situated around the exterior walls. There is strolling musicians working the crowd, and a few patrons dancing with their spouses on the dance floor. Light is by candles on the table and on the wall. All in all a very romantic place.

Jennifer orders for me, in French, so I have no idea what I will be getting. The wine is bought right out, she samples the choice, and then I am poured a glass. It is excellent, and I am even more confused. It seems she is courting me, we just met a couple of days ago, she essentially knows very little about me, I am dressed as a voluptuous female, breasts and a vagina included, but that does not seem to deter her. She reaches over to hold my hand and decides to fill me in a little before I go nuts. That statement delivered after looking at my facial expression.

“I told your CEO that I will sign a ten year contract with your company after they concede a few more things to me. I will give you a check for partial down payment on the first order to show my good faith. The check will be for a hundred thousand dollars, you can give it to your boss when you fly back with the contracts. They have agreed to my concessions, now the only thing remaining is for us to discuss where you fit into this picture. I have asked that they let you go, one of my main concerns that they have agreed to. As soon as you deliver the check and contracts you are fired, essentially unemployed.”

At that point my mouth is open, my jaw hanging down farther than usual. Fired, I do all of this and I get fired. Never mind that I was planning on quitting, surely they can’t do this.

“That is good, because I want to hire you to work with me. I need a COO for my company, a job you will have if you sign on with me. There is one hitch, you have to live and dress as a woman for the job. There are fringe benefits, a pension plan, medical plan, paid vacation, and stock options. Now will you sign on or do I have to use my trump card.”

I stuttered that I need more time, I am still processing the ten year contract and the hundred thousand dollar check. The getting fired bit also trying to derail my thoughts. My mind has not put anything else into the data entry port yet. Then I sucked in a huge breath, “I have to live and dress as a woman, I can’t do that.” Jennifer giggled, you are almost there, keep going and I will let you know when you get to the correct answer.

I shut up, I need to think for a while, this is so confusing, maybe someone can look at what is happening and explain it to me in a way that I can understand. She is going to sign the contract that is good, exactly what I was sent here to accomplish.

I am going to be fired from my present job, a condition from Jennifer for her agreement to the contract. I get the deal completed, how I have still not figured out, and I am let go. All because Jennifer wants it done. Well the jury is still out on that one. All I can see is disaster for me.

The she offers me a job as her COO, a job that I doubt I even know what it entails. I handle numbers, a blasted number cruncher and she wants me as an executive. Some body in this scenario might need some intensive counseling.

Then to accept the position I know nothing about I have to live and work as a female from now on 24/7 for the rest of my life, or until I get fired again. That a more likely outcome. This all came about as a test to see if we were committed to our company, a test that I think I have passed, but to change genders permanently that is a lot to ask. I learned enough to get by for a day or two, now I am expected to do it full time. Surely the world as I know it has gone mad, stark raving mad.

With a few brain cells connecting I tried to reason with her. Even that thought sounds ridiculous when it is said out loud. “Look Jennifer, I am a poorly adjusted male living alone, have worked my whole life doing statistics, I don’t even have a pet, because it would probably starve to death in my care. Now add all these hoops that you have made me jump through, you have got to be insane to think that I can help run your companies. I will take the check and contracts back, then I am resigning my job, and after sufficient time to let the goo in my brain leak out I will start again in some other field.”

“I have enjoyed being with you, underneath your harshness you are beautiful, caring person who your employees seem to love and cherish. I am just not the person you think I am, and being out of your life is a better option for both of us.”

I looked at her face to try and see if she is mad, angry, or just numb. We ate in silence, her not saying a word to me, although she frequently looked at my face. I put my fork in the chicken salad that was served me, it tasted wonderful, but my appetite had left along with the conversation. I did drink several glasses of wine, to numb my senses a little. She paid the bill and we left, still no words between us. I knew I had fouled everything up, I could picture in my mind her tearing up the contracts and the check that I was supposed to return to my company. The limo ride is in silence, with me looking out the window as we traveled along. The scenery seemed different than on our trip here, maybe the driver is taking another way home.

When we arrived at the airport, I knew that I had blown it big time. She is getting rid of me, sending me home right away with nothing to show for my time. We pulled alongside my company jet, the pilot warming up the engines. She faced me, making me look directly at her eyes.

“I am only going to say this once, are you listening to me Debbie?” I nodded my head, but she wanted me to say the words.

“Yes, Jennifer I am listening to you.” The tears were ready to cascade down my cheek, I have cried more in the last two days than I have in my entire life.

“Here is the contracts, and the check, I keep my word. You will fly back present the contract and check, and work out a means for our two companies to work together. As of this moment you work for me. No backtalk, just nod your head in the affirmative.”

I start to say something but she place her finger on my lips. “I will give you two days to conclude that business and wrap up your affairs, no more. You need to get focused and concentrate on getting things wrapped up. Gather up any personal momentous you desire to keep, leave all your clothes and any furniture behind. You can give it away, you will have no need for it here. This is Wednesday, on Friday night my corporate jet will pick you up and return you to me.”

“We will spend the weekend planning the handling of your job and position, then several days shopping for your new wardrobe. A couple of days at the office for you to get your feet wet, then next Saturday we will fly to some romantic destination for some R and R.”

She got down on her knees and took my hand and slid an absolutely gorgeous engagement ring on my ring finger. “To help ensure that you will return I want your word that you will marry me. I am not in a rush, I know that this is quite a bit to get accustomed to, but I love you and want us to be together the rest of our lives. If you can’t agree tonight, I will wait until you do. Your only choice is with me and I will pursue you to the ends of the world to get my way. Until then wear my ring as a reminder that I love you and your rightful place is with me”

I was speechless, I could smell the smoke coming from my mind, totally overloaded with questions, feelings, and emotions. She is looking at me for some decision, one that I haven’t even figured out the question for. To stall for time that I desperately needed I told her I would fly back Friday and we will talk some more. That seemed to appease her some and I received a kiss that defied description. Another short one and she turned me toward the jet and I walked to the stairs. Maybe my heels were touching the tarmac, I had no idea if they were and couldn’t care less.

I don’t remember a thing on the flight back, I am not sure if my mind is even working. As we were slowing to make the approach to the airport at home, I sort of came to and looked at my appearance. I grabbed my purse and fixed my lipstick, finding the check and the contracts in the purse along with a short note.

It was from Jennifer, take time and decide what you will do, my offers are genuine, and heartfelt. I want you so much that I will continue my pursuit until you agree to be mine. Whether it is now or in ten years’ time I intend to make you mine, treasuring and caring for you the rest of our lives.

As we rolled to a stop I saw our limo and Shauna waiting for me. I checked myself in my mirror again, then got up and made my way to the exit. I climbed down the stairs, and was attacked by Shauna, obviously very glad to see me. She took a good look at me, making the remark that she loved the dress. My instant red color blending well with the red color of the dress. She checked me over very carefully, she noticed the longer nails, and the slightly different hairstyle I had been given, all things a female would notice.

I was dragged back to the limo, getting into it a little more difficult than I imagined. I presume that our limo is maybe not as spacious as Jennifer’s. Shauna was bubbling over with questions so she suggested we find a quiet place to eat where we could talk about all that had transpired.

We went to a restaurant just down from our offices, busy during the lunch hours, but usually uncrowded later in the day. We were shown to a table and I prepared myself for the questions that I was sure I would be asked. Shauna noticed the ring first, grabbing my hand to get a closer look.

She looked at me, “you have some explaining to do missy, I send off a young male dressed as a female to try and get a contract signed with a person used to getting her way. On the return trip I see a female get off the plane, confident, assured and obviously engaged. What the hell happened? Are you going to ask us to be in the wedding, you better if you know what is good for you?”

I stammer an answer, inadequate as it is. “I am not sure, she asked me to marry her, also to be her COO of her company. I am confused, bewildered and in love. She is totally different when she gets away from outsiders. Her employees love her, she knows most of them by name, knows about their families, and cares what happens to them. I know I love her, but she wants me to be a female 24/7 from now on.”

“We get along great, she treats me well, and constantly buys me things, but when we are alone the way she cuddles me, holds me, kisses me, makes love to me, just makes my heart soar. We have not done the deed, just kissing and cuddling more than enough for me at the moment. I realize I am a male, but around her I am her companion, lover and probably soon to be wife. I am so confused, when she is near me I am like putty in her hands, so you tell me what do I do?”

Shauna smiles. “Stupid, you marry her. Now answer my question do we get invited to the wedding or not.” I nod my head, but also start sobbing. What am I going to do, I do love Jennifer, although it has only been a few days. Being a woman from now on does have me concerned, probably unnecessarily since for the last two days I have been dressed and acted like one with very little difficulty. Shauna took a couple of minutes and texted Beth and Katrina to meet us at the office as soon as possible. I was still trying to compose myself.

We took a taxi the rest of the way, walking up to reception dressed as a female not as a male hard to get used to. They had a new name badge for me, so that I could get around the office without hindrance. Beth and Katrina met us at reception, giving me big hugs and admiring my ring. They had lots of questions but Shauna told them that we were expected at Beverly’s office so we had to get going. We went right up to the CEO’s office and was shown right through. I had never even been to her office in all of my time with the company.

I took a seat as offered on a couch with seats all round a coffee table. Shauna set next to me, Beth and Katrina set next to us on wing back chairs. Beverly sat opposite us, smiling at my appearance. I retrieved the check and contracts from my purse and handed them to Beverly. She looked them over and her eyes widened at the size of the check. She looked over the contracts to see that they were signed properly, then set them aside. “I thank you for your diligence in the matter, but I want to know more about Jennifer’s request that you be let go immediately. That is not how we reward our employees who bend over backwards to help us in the marketplace.”

I decided to tell her everything, the truth is better than me trying to figure out some way to get around it. After I had disclosed everything, she looked at me. “What do you want from this, I know what Jennifer wants but how about you.” I pondered that for a while.

“Whether you fire me or whether I resign, if you want to keep the contract we need to part company. Also while I am here I need to work out how the contract is to be monitored and handled. Since I am the new COO of her company and you will need to deal with me on all matters relative to the contract.”

I hear four sharp intakes of breath, then some giggling. I am trying to keep a professional atmosphere here and they are giggling. Shauna sums it all up. “We send Debbie to get the contract signed, she accomplished that easily way above any expectations, then comes back to resign her position since she is now their COO. Then we find out that she is going to be wed to the customer soon, another phenomenal feat. As she is handing over the contracts and check from the deal she starts negotiating with us on the terms and conditions of the contract she just delivered.

“Debbie as a number cruncher was a waste of her talents, I wouldn’t be a bit surprised that she soon takes over Jennifer’s company to run it as she sees fit. I think we need to concede defeat here. Debbie anything you want you can have, any terms, any conditions without reservations. Beverly do you agree?”

“Put your requests on paper and I will sign them. Our company is indebted to you for your efforts on our behalf. For that we thank you. Now that is out of the way where did you get that dress, it is simply gorgeous?” That got a laugh from everyone present. I told her where it was purchased, Beverly writing down the name of the boutique Jennifer bought it from.

“I will have a list of my requests emailed to you in the morning. Of course, I insist on Shauna, Beth, and Katrina as the only people I will deal with. I have nothing against you Beverly, but I know the three well and feel more comfortable dealing with them.” As we were getting up to leave I got a big hug from Beverly and a sincere thanks for all you have done for our company.

With that the four of us left Beverly’s office, and headed to Shauna’s. I had to fill the other two in on all the goings on, but we had a good time discussing how this had morphed into such a monster, all because of Jennifer. Shauna gave the other two a signal somehow, and they made their excuses and left. Before we left the offices I told Shauna to split my percentage for helping with the deal three ways, I doubt I will ever want for money so it should go to my BFF’s who helped me through this. I received such a hug, probably cracked a rib too, as hard as she was hugging me.

I could barely keep up with Shauna as she headed for her car. Some light chatter between us on the way to her home, then promptly inside and with some wine seated on her couch. “Now that we are away from prying ears, I want the lowdown on what is going on. Not what you told me at the airport and restaurant but what is going on inside that cute little head of yours. Now spill.”

Instead of talking I started sobbing, the tears seemed to go on for some time, easing up at times then I would look at myself and they would start all over again. I finally ran out of material for the tears, and just sat there staring at a spot on her floor. She gently raised my chin, making me look her in the eyes. I hugged her tightly. “I don’t know what is happening to me, since I spent some time with Jennifer I have been totally incoherent.

Before this I thought I was a fairly normal male, lonely for sure, but still a male. Now I can’t wait to play dress up, new clothes, a different hairstyle, makeup, jewelry all making me weak in the knees. When Jennifer is around that is all I can think about, her kiss, her holding me, our cuddling in bed. It is driving me mad. Right now I am wondering what nightgown got packed in my suitcase for tonight, then what I am going to do about my hair in the morning. My nipples are getting hard just thinking about it. Talk about being messed up, I am way past being a basket case.

Shauna took it all in stride, “it sounds to me that a female is now occupying your body, what you have described is typical of a woman in love.”

“But I am not a woman, I plead guilty to the in love part, I seem to be hopelessly in love. I admit I look like a woman, but underneath all of this disguise I am a male. How can I just switch sides and work and live a female as though it is just another day at the office.”

Her reply quite simple. “Why can’t you be that female, if you look the part, you can do anything you want? Your inner being is certainly female, when this first started you were not against it, like a normal male would be. You allowed the changes, but quickly took command of the situation. You had a plan, made sure we gave you the necessary support then flew out to Jennifer to do battle. How you accomplished the feat makes no difference, you did make it happen. Then you allowed yourself to be swept off your feet by her, coming back with a ring and a proposal of marriage. Now tell me how many males would even allow that conversation to start, much less be wearing her ring on your return.”

“Now let’s talk about the wedding, I want to be included in the wedding party or I am going to hurt you. It is a big day for a female, her future, her significant other, and her life all culminating in the ceremony. Do you want a big wedding or are you going to slip out to Vegas to tie the knot?”

I told her what Jennifer had mentioned, but no decision has been made, I am not even sure I am going to marry her. Shauna hauled off and hit my arm hard, “there will be no more talk like that, do you understand?’ Rubbing my sore arm I nodded my head, if I do turn Jennifer down I may need to learn some self-defense quickly. Three against one is not very good odds.

She convinced me that the only sensible course is to follow my heart, that means finish up here and fly back to Jennifer. She insisted I stay with her tonight, furnishing me a quite risqué night gown to wear to bed tonight. I got lots of hugs and then we retired to our bedrooms.

She would take me back to my hotel to get changed and then to the airport in the morning. Jennifer had already figured out that I would accept and had the plane waiting at the private jet hanger waiting for my wish to fly back. I handed the girls my demands as to distribution, then assured all of them a place in my wedding party if they so desired.

As we departed at the hanger I told the girls I would be in touch, and then climbed on board her company jet. Lots of hugs, tears and kisses were exchanged, before I walked up the ramp as the engines were started. I spent the whole flight thinking about Jennifer’s and my relationship, I did love her that is for sure, but being a female 24/7 still made me pause.

When the jet landed the limo was there to pick me up. I was taken directly to her home, a maid taking my bags and leading me to a bedroom upstairs. As she unpacked for me, I changed my dress, freshened my makeup then made my way downstairs. I was greeted at the entrance to the dining room, Jennifer smiling from ear to ear. The kiss that I received was indeed toe curling, twice I had to stop and take a breath before I was able to resume the kiss.

Finally the kiss temporarily ended and she asked if I was hungry. I asked that we talk first, then eat later. I was dragged to the library, a big soft comfy sofa to be our discussion spot. I took a few moments to gather my thoughts then started. I told her what we worked out at my old job. That I had indeed resigned and was available starting tomorrow. I asked what my duties were to be, half way through the question she stopped me.

I want you to run the companies as you see fit. You are intelligent and I have faith in you. If you want help I will be glad to answer questions for you on what we have done in the past, but I will only allow a question or two to be asked. I am paying you the big bucks for your expertise, so you need to impress me. You name your own salary, just make sure it can be handled within the overall budget.

Now I have the limo for you to use, Steven will be yours for the duration. Marie is your maid she will see to your requirements and the care and maintenance of the house. I will see to the care and maintenance of you, so expect to be pampered and cared for by little old me. You will have to reserve lunches and dinners for me, when I am in town, your job can not interfere in these matters. I am going to be starting a few new business entities, something for you to play with later in the year.

Once she wound down it was my turn to speak up again. “I love you with all my heart and I will marry you but I want to have some time to enjoy the dating, the romance and the loving before we tie the knot.” I slipped off the engagement ring, giving it back to her to hold for later. Well, she wanted nothing to do with that.

“Wear the ring, we will just arrange to have a long engagement, a year maybe, depends on whether you get with child and I have to make an honest woman out of you.” I giggled, but she kept her straight face. I let it drop, surely I can’t get with child, can I?

I asked again about me being her COO. I have no experience, crunching numbers not very good training for an executive that runs a business. Surely you have someone more qualified to do this job. “I have picked you, and that is final. You do have the most important qualifications for the job. You care, are sensible and will do what is necessary to complete the job. End of discussion. Now Steven will take you to each store or warehouse unit, for you to meet the people and see what is going on.”

“Any crisis will be made known to you, so that you can handle it, otherwise keep with getting to know the people and business. With the products from your company, introduce them slowly, allowing our customers to know that we now carry them and for your company to get used to our volume.”

“Remember lunches and dinners are mine, so keep those times for me. I will let the marriage slide for a while, you will live with me and sleep in my bed though, and there is no discussion on that. Your closet is stocked with clothes, and the first stop every morning will be the salon so that they can be sure that you are beautiful and ready for the day. After you accept your status in life I will allow you to do your own hair and makeup if you want.”

“Now what else has to be negotiated tonight or can we eat.”

“First I need a kiss real bad, then a lingering hug, after that food will be fine. I love you, it is just that all of this is so new and different. I am scared one minute and terrified the next. I will try real hard to please you, but still wish you would reconsider the COO position. I feel so inadequate, maybe I can learn to live as a female 24/7, but run a business is so scary.”

I got the kiss, the hug felt so good, lasting for quite some time. I was dragged to the dining room, a single covered dish at each of our place settings. She helped me with my chair, and then kissed me again on the lips. As she backed away she lifted the cover to reveal a hamburger, with curly fries surrounding the burger. I grabbed a fry right away, it was so good, and then a bite of the hamburger, the juices running around my lips as I tried to lick them before they could get away.

Then I did something so unexpected, I got up from my chair took my plate and set it down next to hers. I plopped my rear end on her lap and kissed her so hard. Then quickly turned back to get another bite, the rest of the meal was a kiss, a bite, then another kiss. All the time I was twisting my fanny on her lap, I knew it was bad, but oh so much fun. It was almost an hour later when the burgers were finished, my head laid on her shoulders my face nuzzled into her neck.

The evening was wonderful, after dinner we cuddled first in the living room and then we moved our efforts to her bedroom. I was held tight, my head kept on or near her breasts all evening. Lots of kisses were exchanged, about three AM I finally succumbed to sleep, Jennifer still holding me tight to her.

I woke to kisses and when I didn’t attempt to get up she attacked my nipples through the nightie, I knew I had some feeling there, but one tongue lick had me moving quickly to escape her mouth. My nipples are rock hard, goose pimples attacking my whole body relentlessly. Her smirk was back, as she crawled across the bed to get to me. I backed away, giggled and ran to the bathroom, closing the door in an effort to evade her pursuit.

We spent the entire morning playing cat and mouse, my feline soulmate prevailing most of the time. That is how I viewed Jennifer, someone who saw what she wanted inside me, and would not settle for anything less. I suggested we do something business like for the afternoon, since we played all morning. She made a few phone calls, while Marie helped me get presentable. Gawd, so much to get used to, but if I admitted to my true feelings, something that has been missing my entire life. To get a break from Jennifer’s antics, I arranged for Stephen to take me to a couple of the store branches.

The ride was quiet, time to reflect on all of the things that had happened, without someone’s kisses distracting me. I came to the conclusion that maybe I could do this, a new life, a new job, but one filled with lots of challenges and excitement. As we came to the first stop, I got my lipstick and my mirror out of my purse, needing to make sure I was presentable, a COO always needs to look good.

The manager of the location met me and we walked the store meeting the employees and discussing any relevant problems. I actually saw a few things that would improve sales and mentioned them. I think the manager was a little embarrassed, the things I mentioned were pretty basic and should have been included routinely. The second stop was almost the same, although my suggestions were in a different area.

Jennifer met me for dinner, at one of her favorite eateries. I was hugged real hard as soon as she saw me and taken to her table, my hand firmly in her grasp as she pulled me along. She started in on me right away, mentioning the two store managers I had met and their respect for me after our meeting today. I had pointed out to them some improvements, but not made an issue of it. After they had implemented the changes they realized they should have been doing it all along. Both managers called Jennifer complimenting me on my tact and skill in business matters, an excellent choice for a COO position.

Now that we know you are capable of doing the job, I expect great things from you, both in business matters and in the bedroom. Making more money to invest into other businesses, now that I have a capable manager in house, means the sky is the limit. On the ride back to our house after dinner, I was sexually assaulted in the most wonderful and diverse ways.

It continued once we were in the bedroom, but this time I insisted on an early bedtime, since I had lots of stores to inspect and manage. I know she heard me when I requested an early bedtime, but it was four hours later before she finally wound down enough that I could fall asleep. When I awoke the next morning she was spooning me from behind, her hands on my breasts keeping them warm and the nipples erect.

Maybe it won’t be too bad, something to keep me occupied, wonderful clothes to wear and a lover that seems to be insatiable. To think I thought a career in the numbers game would get me nowhere, instead it got me into dresses, makeup, and lingerie, then the rest was history. Asking a lot of someone, but well worth the time and effort. One look at Jennifer, it indeed was well worth the effort.

© 2016 thru 2024 by Francesca