It was a stupid wager, but then lot of betting is done without the consideration that you have no control over what is bet on. I worked in a small office handling the computers and analyzing customer’s web presence as to functionality and purpose. Our branch office was a part of a huge corporation that dabbled in lots of things, all computer or web related. We supplied answers to some common business problems, problems that most businesses did not have the resources to handle themselves. If a company was selling goods over the internet and they got some inquiries from out of the country we supplied the information and know how for them to be able to sell their goods internationally. That included licenses required, rules and regulations regarding their sales in each country and shipping requirements to get their goods to the new customer.
In the U.S. we supplied specialty software to allow their customers to view their product in their own native language. Software to get the pictures of their product on their web pages and blended into their presentation without overwhelming the customer. We also consulted on their web presentation offering some different ideas on how to attract the customer and close a sale on their product.
I mainly worked with the computers behind the scenes, analyzing a customers web site and then offering suggestions on how to improve it. Then we had sales specialists that took my recommendations and approached the customer with my advice, and our help in getting that advice implemented. We had three specialists that performed those tasks for the customer and then helped them keep the website current and functioning properly. This was done with a service contract, so much a month to keep things running smoothly. That was the basis for our company, keeping their web sites functional and profitable.
My boss is a female, energetic, knowledgable and quite proficient. She has a way with employees that served her well. Shelly was always kidding us about something, teasing us about our manner of dress and often engaging in small wagers about this thing or that. If she lost the wager she would always honor the bet and not try to weasel her way out of it. With each employee the subject of the wagers were different, some would be about sport teams, others about something happening in the news others with appearance or in a few cases some of our customers. She is well liked because she interacts with us freely and is so down to earth. In general, the office adopted some of her behavior, some wagers and kidding exchanged between the employees as well.
One of the ladies in our office was attending a wedding, her sister getting married to a fairly wealthy boyfriend, and since she is her maid of honor the dress for the affair to be very formal. In this case, she wanted her hair in an elaborate updo since both her and her sister have such long hair with their dresses being strapless, a perfect combo. They had some jewelry that would be included in the elaborate updo along with some ribbons that matched the color of the dresses. Their Mother had spent a fortune on the dresses, the total coming to just under twenty-five thousand dollars for both dresses. The wedding to be held in one of the fanciest churches in town, with a coach pulled by four horses to take the couple to the reception a few blocks away.
Anyway I had gotten carried away with regards to the future maid of honor kidding her about the fancy hairdo ever chance I got. She wasn’t able to take time off work for the appointment for the hairdo at her salon, so ended up taking the appointment in the evening a couple of days early. This required her to work those days with the fancy hairdo. There would be an employee of the salon at the wedding to fluff up the hairdo, but not able to create the updo right before the wedding.
She showed up for work that first day, her hair piled on top of her head, with tendrils of hair hanging from each ear and a multitude of curls from a bun at the back of her head. The jewelry looking like diamonds around the bun with the ribbons hanging from each tendril. It was quite pretty and very lavish. Also very over the top for a workplace. I guess I got carried away with the kidding although Kay seemed to take it in stride. She told us abut her sleeping arrangements since if she laid down it would squash the hair do. So she slept in a chair at night with pillows keeping her head up, and a scarf to hold the long ribbons from getting wrinkled.
Over lunch we were talking about a customer that in the past had given is quite a bit of trouble. Each of us had dealt with them at one point in time, however I seemed to get them more often than the rest. Shelly proposed a wager between her and I. If I could handle them by myself the next time they became a problem she would make sure I got a bonus for my efforts. However if her or one of the girls had to step in to handle the customer I would have to pay a penance for a month, the nature of the penance to be obtained from
suggestions of the other office girls. Each girl would get to offer one suggestion for my penance all the suggestions to be placed in a box and I would then select one if I lost the wager. So the kidding got transferred to me, the girls making all kinds of suggestions about my penance, since they were sure if I got that customer again I would be paying the penance. Then they started on what they would say to the customer to soothe things out, and make sure we kept the customer. There was even a few hints that maybe down the road another wager could be done, and what consequences that might mean for me. Just think you may never be in a place where there was not a penance to be dealt with.
Shelly used little things like this to make each person feel like they were part of the team not an individual out on their own. It has worked in the past, every little wager looked upon enthusiastically by all concerned. Even this latest wager already talked about, with several gals already writing down their suggestions for later. Then looking at me and giggling away. I know it sure caused an increase in the chatting.
Of course I wanted to win the wager, a bonus always appreciated these days. In the past Shelly’s bonuses have been quite sizable. So I started preparing for my talk with this customer, brushing up on their history and requirements. In the past they have complained or required help about every ten days, so it wouldn’t be long before I am again having to interact with them. Maybe this time will be a charm. A voice deep within me was screaming to pass on the wager, too risky and not knowing what I would have to do if I lost making it too risky. Did I listen to the voice, nope full speed ahead. I shook on it with Shelly, the smirk on her face quite large.
I have in the past been able to solve their problem or handle their complaint by myself about half of the time, so the odds might be slightly in my favor. I had just finished two web analysis for customers sending the suggestions to our sales people. I got a phone call from a customer to handle next, yep the customer in question was on the phone.
I introduced myself and listened to their problem, then formulated my response. This was an employee of theirs I was not familiar with so I explained what had happened, actually a mistake on their part. Since I had worked with them in the past I carefully explained what to do and in the proper order. Silence on the other end. I asked if I could help them understand something better or if I could go over the procedure to correct the problem again. The employee got huffy, demanding that I let her talk to my boss. I asked her to hold for a minute and I would get her on the phone. Oh gawd came to mind, but I needed to get Shelly on the phone quickly before the customer got any more upset. I had printed the procedure out like I usually do, to be kept in a file of theirs in case this came up again. I took the printed sheet over to Shelly explaining what had happened. And handed her the procedure for handling the problem. Also filling her in on who she was talking too. I went back to my computer my head hung down, I presume my luck with hanging them now non-existent. I did not think about the wager till later, when that single thought came running across my mind causing me to lose track of what I was doing and having to start all over again.
Shelly seemed to have no problem with the customer’s employee as she went over the fix and then waited as the employee implemented the procedure. It worked right away and Shelly was thanked profusely for her help and guidance. We had gotten real busy as Shelly was talking to the customer so there was no chance to talk about what had happened that day. I ended up staying late since I had two analysis to finish before heading home. Shelly came by as she was heading out, gave me a squeeze on the shoulder as she left, with the biggest smirk on her face. I let out a sigh, the thought of my penance to be determined coming to the forefront once again.
I did finish a little later so at ten minutes to six I signed off my computer and headed home. I was pooped so I nuked a TV dinner, nibbled on it then took a bath and crawled into bed. I was apparently more tired than usual sleeping through the first alarm. When the second alarm sounded, I jumped up, slipped on some clothes and drove to the office. No breakfast, not even time to brush my hair. I did make it just before eight, our normal starting time. As I set at my desk, the phones started ringing and it was almost noon before they relented a little. Luckily for us the company stopped all calls to us during the lunch hour, giving us a little piece and quiet. Believe me on some days it was really appreciated.
We chatted about all the calls we had that morning, then Shelly asked the girls for their suggestions for my wager with her. Well it was handled quickly as each of then took their suggestion from their purse and handed them to Shelly. Shelly read each one then placed them in a box on the table. Her smile got bigger as she looked each suggestion over and then placed them in the box. The box was slid over in front of me and I reached in and stirred them up a little then selected one. I pulled it out and handed it to Shelly not wanting to look at it until the last moment. Shelly paused for a minute then read the suggestion. A curly updo for the whole month. I sunk in my seat and moaned, each of the girls reaching out to me and telling me that it wouldn’t be that bad, I may even learn to like the style.
The lunch hour was up, so the girls got up to resume their work and Shelly took out the remaining suggestions from the box. I presume to make me aware of the other choices. As she opened them up and laid them in front of me to read, each suggestion was nearly the same, except maybe a few words changed here and there. So it didn’t matter what I chose, I will be doing the penance that every girl wanted me to suffer through.
Shelly told me that this particular penance was not what she had in mind for me, so she will make sure that something else be found to satisfy the girls. A head full of curls and ribbons on a male kind of severe, limiting what I could do when off work and during the night time hours. I immediately though of having to sleep in a chair every night for a month, none of the things that I had considered.
We got busy, her computer dinging telling her that there were more calls yet to be handled, I got up and made my way to my computer , signed on and took the next call. Shelly was doing the same and it was four hours later when things eased up some. I still had three sites to analyze. So I got started on them, hoping to finish them before six. Shelly was also kept busy, with her finishing a few minutes before six, She wandered in and sat in front of my desk watching me finish up the last analysis. With that finished I let out a huge sigh and signed off. To my surprise she invited me to dinner, her treat. I told her yes, but she didn’t have to pay my way.
My car was left at work, she would drop me back here after we ate. The restaurant she had in mind was nice, good food all low in calories and very reasonable in price. The low calorie bit was a joke, the food was so rich and tasty I am sure I gained ten pounds just looking at it on my plate. After we finished eating she wanted to talk about my wager and penance. I figured as much as soon as she asked me to dinner. I kept quiet letting her tell me what she wanted to do. I had already decided to go through with my hair in an updo, not wanting to experience it, but more interested in fulfilling my part of the wager. Not try and weasel out of part of it. She said she had went back to my personnel file and looked to see if I was married. Since I never talked about a girlfriend she presumed there was none at the moment.
She had taken my photo from my original employment application and shown it to one of her friends, who works in a salon to see if what she has in mind might work out. According to her friend, it would work out perfectly. I saw Shelly take a huge breath and then heard her tell me that the best way to handle this is for me to dress as a female during the month. Nothing over the top, just a dress instead of pants and a shirt. No makeup, the hair do will supply the female image by itself with no further enhancements necessary.
She stared at me, waiting for me to say something. I knew I would accept, but any chance to wind her up some can’t be passed up. I carefully selected my words then asked her. What no panties? Well that broke the ice and we giggled and laughed for quire some time. I managed to tell her that I wanted to follow through, not wanting any one to think I would welsh on a bet. She told me she would make me an appointment on Saturday morning, thus allowing me the weekend to get used to my new look.
I would be expected to pay for my updo, but her friend is giving me a huge discount. The dresses for my disguise Shelly would furnish, the cost worth it to her, to see me with bare legs and short skirts. I asked about pants, but Shelly reminded me of the company dress code prohibiting any pants at the workplace. Oh well it was a thought.
I agreed to everything, not wanting to let the girls down. I am sure they are looking forward to me with a very feminine hairdo and wearing a dress. Shelly offered to pick me up Saturday morning and take me to the salon. That way she can introduce me to her friend. I am sure it has more to do with seeing me first with an updo and also first to see me in a dress. Oh well, nothing to do but put up with it. I have noticed I am saying oh well quite a bit now, if that is the only saying I pick up in the ensuing weeks things will be fine.
Shelly was early ringing my door bell, incessantly by the way. When I opened the door in my robe, she swept pass me and dragged me toward the bedroom. I was pushed inside and told to get dressed. I presume she saw the bed through the open door.
Don’t take time to make your bed, we have more important things to take care of. I found here looking around the living room when I emerged, smiling and anxiously waiting to get her hands on me. Once she latched on we were out the door and into her car in less than a minute. The drive to the salon was less than a half hour, she parked in the first parking spot up front and came around to extricate me from the car. Into to the salon and straight back to a room in the back. Her friend was waiting for her, we were introduced and I was handed over to her.
Madison was friendly, but focused on giving me a gorgeous updo, her words. She ran her fingers through my hair proclaiming that such a feat would be so easy. Meanwhile Shelly headed off to their clothes store to shop for me. With Shelly’s sense of style and humor I am sure I will be on display, that is most of me will be on display. At the office she seemed to be the one with the most skin visible on any one day. Not a person you wanted to pick out your wardrobe.
Madison was meanwhile shampooing my hair, then numerous conditioners were added and left on for a while. After that was accomplished she combed out any tangles and started to cut my hair, evening out the length and getting the split ends removed. Then numerous large curlers were used after she saturated my hair with a setting lotion. Once all the hair was in curlers I was moved over under a dryer and told to read a magazine or two, she wanted my hair to dry slowly, that along with the setting lotion would guarantee my hair to hold the curl for at least a week. She has already made appointments every Saturday for me at the same time, so that my hairdo will always look fresh and pretty. She smiled when she said pretty, the first attempt at kidding aimed at my new look.
I did read several of their magazines, the article on avoiding unwanted male attention of special interest to me. I sincerely hoped that I would not be attractive enough to draw any male attention, but these days you never know. My mind did consider all the things that may affect my life now. I doubt my new hairstyle will allow anyone to presume I was a male. So any venture out for groceries, take out, or any one of a dozen other things and everybody I will come in contact with will most likely see a female. I guess wearing a dress might help, at least that way I will not be so obvious. Dressed in male pants and a shirt, but with that hairdo will draw everybody’s attention no matter who they are. So my life is going to change, starting as soon as Madison completes my updo.
Once out from under the dryer she removed my curlers, each curl springing back into the tight curl when in the curler. She brushed the hair straight back and secured it into a bun, the remaining length spilling out from the bun in ringlets of curls. Gawd, why did I have to let my hair grow so long?
She then took each curl and brushed it until it relaxed some, tying a ribbon into the hair at the base of each curl. There was over fifty curls with attached ribbons when she finished the ribbons hanging down to my mid back, the curls dangling around my shoulder blades. She had kept two curls full of hair at each ear separate, those were secured with a diamond encrusted barrette, the ribbons a blend of colors and shorter than the other ones at my back. I am sure the diamonds were fake, but they looked quite realistic none the less. I let out several sighs, my image was worse that I had imagined. The hairdo screamed female, even though my face had no makeup on it, any masculinity I might have shown before today was gone.
Madison had given me a wrap of sorts, to be placed around my head before I laid down. I was to put it on after bending over keeping the curls in the open part of the wrap. It attached in the front, fitting tight around my head but leaving a cone at the top of my head, all of my curls and ribbons laying in that cone. It would minimize any damage to my hairdo, removing it and shaking my head should let most of the curls to fall back where they belong. Another sigh, this wager now even more intrusive on my life. I really hate that customer, wanting to call them up and cuss them out. Count to ten, maybe that will help. I made it to twenty-one before I calmed down some.
Time for Shelly to show up, a dress and some panties in her hand. I didn’t even wait to be asked to strip, the dress would be much preferred over what I had on now. At least, the incongruity of my clothes and hairdo would be handled. The panties were silky, and as they slid up my legs causing all kinds of never experienced sensations. The dress not much better, a sweater dress conforming to every curve of my body. I never did have much body hair, a small patch of fuzz on my chest and of course some around my genitals. Although there was no breasts or hips to fill out the dress a quite attractive female was the image in the mirror. Shelly eyes never left my body, smiling and giggling as I donned the clothes. She told me she had six more outfits in the car, for next week, all just as pretty and girly.
She had already signed the ticket for the services, so I was led out to her car. I did remember I was to pay for the updo, something to discuss later. I forgot to mention the heels that I was gifted with, way too tall in my thinking and only two small straps holding them on my feet. I think the best description would be dainty looking. I nearly fell on my face a couple of times, but by the time we got to her car I was managing. Straight to her house, for that I was thankful, venturing out anywhere was not something I desired. She got the car door for me as I tried to duck down some to get my head and body out of the car with the hairdo.
I followed her into the house, then to the kitchen. She showed me to a bar stool by a serving bar and I attempted to get my butt on the stool. I finally made it but also giving Shelly lots of laughs. She placed a soft drink in front of me than a straw. I looked at the straw, then remembered that females often drank with a straw, helping to minimize damage to their lipstick. Oh well muttered again, but used the straw to drink some of the soft drink. I even looked a the straw to see if I left any lipstick marks. Shelly had been watching me then giggled. That giggle turning into laughter a few moments later.
As we were setting there she suggested that I stay with her, so she could help me with my hair and clothes. I tilted my head some staring right at her. Okay I have my motives, but just trust me right now and agree to stay here for the month. I smiled, asking her if she was going to help me out my panties on every day. She got up from her stool approached me and grabbed me and pulled me into a tight hug, holding me and not letting me escape. Yep, I will help you put them on and take them off every day, you can count on it. The hug turned into a kiss, erotic although brief. I was shown to the bedroom, quite pretty and very feminine. I king size bed in the middle of the room. I am shown to my side of the bed, extra pillows stacked on my side to help with preserving the hairdo. She pointed to the bathroom door and to the closet where she will hang my new wardrobe. I needed to use the bathroom so I headed in that direction while she returned to her car to get my clothes.
Dress up and panties down, I sat on the toilet to do my business. I did think why I had sat, since I never had done that before. Another unanswered question for later. When I returned my clothes were hanging in the closet, a pair of panties attached to each dress. On the floor directly underneath the dresses was two more pair of heels, I looked at Shelly, she smiled dress code requirement for a female. Then I spotted something laying on my side of the bed, a frilly lacy nightie. I blushed ten different shades of red. As Shelly gave me a smirk. House requirement, you will love it.
She indeed helped me out of the dress and panties, twirling them around her finger after getting them off. I tried to be mad, but she was obviously having fun doing this. Into the nightie, with way too much help and then my wrap for the hairdo. It felt funny to have all of that wrapped around my head, but I guess if it saves me anguish the next morning it is worth it. I was laid in bed, then Shelly started wedging the pillows around me keeping me pinned to the bed. My arms were buried under several pillows and my head was wedged tight with pillows on both sides. My covers were raised to my neck then tucked in tight. She leaned down and kissed me on the lips causing all kinds of sensations to course through my body. She made sure everything was tightly wedged around me then went to her side of the bed and crawled in. Turned out the light and was soon asleep.
I lay there comfy and still savoring the kiss. I guess I could extract myself from the pillow prison, but saw no need to. It was warm, and I felt secure. All of this to preserve my hairdo, I suddenly realized I was looking forward to more nights like this, maybe a month will not be enough. A few minutes later I also slipped off into dreamland.
I woke having to use the bathroom real bad. I debated trying to extricate myself, but thought it would be more fun if Shelly got me out. I moaned and wiggled in my pillow prison, finally getting her attention. I whispered I had to pee, and soon I was pulled out of the bed. I was trying to get to the bathroom while she was trying to play lip lock with me. I finally prevailed and was setting like a female does. There was way too may mirrors in the bathroom, the one that was in front of me showed an image that was downright comical. My mind finally engaged and I flooded the toilet. A few more minutes and the bed would have floated away.
As I made my way back to the bedroom Shelly was there to help remove my hair wrap and ease the nightie over my head. I was helped into my panties for the day, as she made sure they fit properly and were snug to my body. I just stood there enjoying her ministrations on my behalf. The dress next, then she went to get dressed herself while I was expected to wash my face and brush my teeth. Before the dress she made sure I was doused in her scented powder, now the only thing I could smell. I sat in a chair oin the living room waiting for her, crossing my legs different ways trying to keep so much skin from showing. I decided it was hopeless, until I got to my desk and scooted the chair in, I would be showing most of my upper thigh in this dress.
At least, I would have new things to occupy some of my time at work. Shelly bundled me off to work, a frilly coat over my dress since it was a little cool outside. The trip didn’t take long, although to me it seemed like an eternity. Looking at the clock on the dash it took only twenty minutes. It seemed like an hour or more. Part of the anxiety is what the girls would say about the hairdo, since I had kidded Kay so bad when she had to wear the updo to the office, I expected some in return from her and probably all of the other girls. Once parked Shelly looked my way, waiting for me to get out of the car. I swallowed and finally emerged from my side of the car.
Shelly led me in and right into the middle of the office. She got everybody’s attention and announced that Kody is now a female as far as the company is concerned, kidding as in the past is allowed but anything malicious or hurtful we be dealt with immediately. Now lets all give her some hugs, a few jibes and then get to work. They did just that, Kay giving me the biggest hug. I apologized for my behavior in the past, but she just smiled and told me at lunch we can compare notes.
Work took precedent and soon we were all busy on the phones. My third call was nemesis that got me into this mess in the first place. I saw Shelly look my way, apparently she knew who I got and was watching to see what and how I did. This time when I introduced my self I used a little higher pitch to my voice and the prefix Miss to my name of Kody. It turns out it was the same gal that I had talked with last time, but a different problem. I went over the solution to the problem, made sure she had straightened it out on her end then asked if there was anything else I could help her with. There wasn’t, she thanked me for the help and hung up.
I let out such a sigh, thanking the gods that managed to get me through that crisis. Shelly called me over and suggested that I keep using the female voice and introducing myself as Miss Kody. Before she could say much more the phones started up again.
At lunch Kay wanted me to tell her everything about my appointment at the salon and about my first night sleeping with the updo. We did compare notes, she was fascinated with the wrap, wishing her stylist had mentioned something like it.
The afternoon was so so, busy then it slacked off, then busy again. I had four analysis to do this afternoon, so was busy anytime I got a few moments. It seemed business was picking up, from the amount of work, coming my way. Those looks at the customer’s website, meant possible new business for the company.
The month passed quickly, each day a repeat of the previous. Shelly insisted I stay with her, since her kisses were so awesome I agreed to stay. On the last day of the penance I was summoned into Shelly’s office and told to sit. She hemmed and hawed trying to find the right way to tell me what she wanted. I let her stew for a while then suggested that I might go first.
I am going to stay as a female if I am allowed by the company. Maybe not sporting an up do every day, but still with a proper feminine hairstyle. I have an appointment tomorrow morning to gain the figure needed to fill out my dresses in the proper manner. Of course makeup and heels.
I am not sure where I will live, the place I am staying at now is pretty nice, but I am not sure if I am desired as a future tenant. Maybe you can give me a reference, that might help make up the land ladies mind to keep me. I looked her way but did not see any indication on her part for either option. I figured I was not wanted, so got up and headed to the door. Shelly yelled for me to sit back down and keep my mouth shut.
She fished around in her top desk drawer, pulling something out in a little black box. Being a former male I had no idea what it might contain. She came around and grabbed my hand and opened the box, removing something from it and then sliding it on my ring finger. Oh gawd, escaped my mouth then I fainted. When I came around, Shelly was staring at me, telling me she wanted just one word from my mouth and it better be the right one. I said yes as she asked me to marry her. The kiss was the best yet, only the incessant ringing of the phones causing us to stop. I ran to my desk, yelling that I will continue that kiss as soon as work is over. The rest of the girls giggling away.
I did get another week of an updo hairstyle, this time in preparation for my wedding. Shelly had the ribbons used in the updo made extra long. Then at our wedding reception used them to tie my hands together, less grabby and more to her liking was her words as she led me by the ribbons to the limo. I stayed that way for the honeymoon night and most of the next day.
It indeed was a profound wager that day a few months ago; a different life, a soul mate and a wonderful boss, what more could a girl ask for.
Story Complete For Now
© 2016 thru 2021 Fran Cesca Walker