Working Vacation

Part One

I should have known that something like this would happen to my vacation. Every single time that I come to a wonderful point in time and can do something that I want to, something like WORK has to intrude!!!

Of course, it was not like I had not been expecting this, as one could expect from my tirade there. But it was true. Each time I had been planning to take a vacation, the boss would call and tell me that the world was going to explode and life as I knew it would come to an end unless I did this... Or that... Or the other thing... And this time, it was no different.

She had called me, on a Saturday morning, to politely beg me to stop by the office and then fly out to Vegas, seeing as it WAS on my way, and drop off a package for one of our clients and then head on off to Reno so I could enjoy my vacation. It bothered me a little, except that at least she was willing to give me a first class plane ticket to Vegas, Reno and then home. I had my own ticket to Reno but this sounded like a much better offer. Plus I had refundable tickets so I could get some of that money back and spend it on something more desirable.

So off I went, stopping by the office to get a rather large envelope and a smaller one containing the tickets and even a hotel reservation in Vegas at a very nice place just outside the strip. One night in a fairly nice place and I was surprised to see that I had not just an ordinary room but a small suite. And a quick note saying thanks and that she hoped I liked the room.

So I hopped back into my little car and drove out to the airport. I had my two bags packed and with my round trip first class tickets, sailed through the check in process and hoped that the TSA didn't decide to check my bag as there were things in the one bag that I would be somewhat hard pressed to explain.

As I got to the gate, I was checking to make sure that I had everything with me that I was going to need for the flight. Mostly thought, I was making sure that my secret didn't show. I felt confident and relaxed as the attendant called the flight and I got onto the plane, sitting in the comfortable seat, getting a drink of wine as we waited and feeling rather silly as I had never really experienced this before.

After a few minutes, I did have to get up as my seat mate arrived and I noticed that she was rather smartly dressed in a short but very fashionable skirt, high heels and a beautiful silk blouse. And her legs were encased in stockings as I noticed the hint of lace trim as she casually stretched, taking off her jacket and giving it to the flight attendant to be hung up. As she sat down, she adjusted the hem of her skirt and I sat down. She ordered her drink and she smiled at me. We introduced ourselves and talked a little as we waited, then the captain started his little talk and the safety announcements were started. I stuffed my case under the seat and got finished getting ready for take-off. A short while later, I pulled my case out and started to go over some things I had, including checking the location of the hotel I was going to be staying at in Vegas and then started reading the book I brought with me.

She had started working on something and I never really paid too much attention to her as I figured that she didn't really want to be bothered. I had glanced over to see what she had been doing, mostly out of curiosity and noticed that she actually worked for the same company as I did. And one of her business cards was visible stating that she was one of the VP's of the company and that worried me a little. Not so much because of who she was but more for the fact that sitting next to her, I was actually thinking that she was “hot” but also kind of jealous, too. I went back to my book and basically got lost in it until I felt her hand on my leg and I  realized that something was happening I wasn't expecting because though her hand was touching something, it had not moved but rather I could feel her finger trace a shape on my thigh. Then I felt her lean over.

“Ooh, I wondered if that was a garter-belt holding those stockings up or if you had on thigh highs. I'm kind of glad that you DO wear a garter-belt, Paul. But I gotta ask... Over or under?”

Needless to say, I was a little shocked, not only because my secret had been discovered but that this woman, who worked at the same company I do, could either find it interesting or could ruin my career with one little work placed in the right ear. I felt a little squeeze on my leg as I replied, “over.”

She smiled at me. I smiled back. “Now, do you have more than just lingerie with you on this trip or were you just expecting to parade in your underwear all week, sweetie? Not that it would be a problem or nothing but...”

Now I was a little confused. She was asking me if I had clothes??? I told her that I did and that got me a bigger smile. I was starting to “melt” as it were, looking at her smile. But what came next kind of caught me off guard.

“So, do you like to play a little? Maybe a little of that 'damsel in distress' kind of thing or are you just into dressing up?”

All I could do was GULP and nod... I was afraid to say anything, afraid that everyone in the plane would hear me answer her... And then I got that little smile and a gleam in her eyes told me that maybe I should have not said anything... Until I realized that I really hadn't said anything.

“Well, Susan did tell me that her assistant would be an interesting seat companion as well as be willing to help me out a little tonight. And if you help me out maybe I can help you out a little, as it were. Do you think you would like that?” When I nodded at her, I felt the beginning of a smile come across my own face, thinking that maybe I could have a little vacation before my vacation in Reno.

 

We finally landed at the airport and I went to the luggage carousel and found my two bags and even grabbed her bag. Then a quick ride to the rental car agency to pick up a rental, a Lincoln Town Car, which was nice but really unexpected. But when I asked her where she was staying, that was my big shock.

“Why Paul, I am staying in your suite tonight, of course. I will be taking it over tomorrow afternoon anyway but tonight, I will share it with you. Not that you are going to be getting into my panties or anything... Though they might just fit you...” this did cause me to laugh a little bit as she smiled at me. “But I happen to know that there are 2 bedrooms in the suite. So relax and let us get there. I need a shower and, well you need to change anyway. Because I know just the place we can go for dinner, two girls on the prowl...”

We got to the hotel, which was indeed a little way off the strip but it was a very nice place and the suite was HUGE! I took the small bedroom and opened up my bag, expecting a little privacy as I checked my bags but she came in and looked. When she saw that the two bags contained mostly female clothing and underwear except for two changes of male clothes, she smiled and started going through things.

“Just sit down, Paul. I want to see what I have here to... Well, I have a feeling that you are going to be an interesting evening diversion to be sure. A little French Maid Uniform, Paul, complete with petticoat, apron and ruffled panties. And these stiletto heels. Tell me you can walk in these?”

“Yes, I can walk in those, as well as those six inch heels in the other bag.”

“You do mean WALK as opposed to take a few steps and then fall, right?”

“Yes, I can walk in them for a while.”

“Good. Now, I want you to get into the shower and clean up. I see that you are very clean shaven but still, shave a little more. By the time you get out, I will have an outfit picked out for you to wear to dinner. Then we can eat, talk and if you are good, or not, we can see about taking care of your other, more SPECIAL, need... Though we may have to stop along the way to pick up something... Seeing as I may not have everything I may need for you...”

I looked at her for a second then headed off to the shower, spending quite a while making sure that my legs were clean and smooth shaven, as well as the rest of my body. Then I got out of the shower and dried off. When I walked into the room, I was surprised to see that my maid uniform was hanging up on a hanger in the room, as well as all the other clothes. On top of the dresser was all my panties, bras, slips and stockings. On the bed I saw a complete outfit, which I had to admit was kind of classy looking, with just a hint of, well, slut, if you looked at the skirt length.

When I picked up the bra and my forms, I found the garter-belt and stockings, along with a pair of my panties. So I started getting dressed, taking a look and not finding the gaff I used under my panties to hide my bulge. I figured that I had forgotten that but checked my bags none the less just to be sure. I then pulled on the skirt and put my arms through my own silk blouse and finished dressing. Then I realized that my make up kit was nowhere in sight. Nor was my wig.

In minutes, however, she came into the room holding several things, including my wig and make up case. She was also holding onto something else. It LOOKED like my gaff but it seemed like it might be a little more sinister as she brought it closer. When I looked at her face and the strange glean in her eyes, I knew that it was going to be something a little more than a little something to hide my male parts...

“Okay sweetie. I can tell that you have some idea what this little beauty is. It works along the same line as that awful gaff of yours. It does the job, I am sure, but I think that since time is short AND I am feeling not only a little hungry but also a little mischievous right now, I think that these times call for something a little, shall we say, EXTRA. This is a very special gaff, if you want to use that term for this. Oddly enough, this is one of the many little odd-ball things that we manufacture and sell and, well, it just seemed appropriate that maybe you wear one as well. So, first of all, you will need to take off your cute little panties and even the garter belt. Then I can help you get this on.”

I took a few seconds to take care of what she wanted done and I was starting to feel a little nervous as well as, as I felt and watched my manhood start to show it's rather untimely manifestation of what I was feeling. Of course, it certainly didn't help that she had come out of her shower wearing, well, ALMOST nothing at all... And the scent of her bath gel or whatever was rather intoxicating as well. But she really didn't seem to be bothered by my growing erection and actually smiled and chuckled a little under her breath, saying something about how men always think with their peckers but soon I would learn better. Then I felt something sharp and painful and instantly, I was brought out of my little daydream and the reality of the pain in my testicles and penis brought me to the here and now.

To my horror, I felt a cage being locked around my penis as it got smaller and smaller. Before I could even think of stopping anything, I felt my penis being pulled between my legs and a strap being locked in place. When I looked down, I couldn't see... ANYTHING!!!

“No sweetie, it isn't cut off, though I bet that little jolt made you think something had happened. Not to worry. If you are a good little gurl, I promise that you will have full use of your little pecker there in no time at all. However, if you are NOT a good little and OBEDIENT sissy, well, let me just say that there is one other little chastity device that we market that is far worse than that one...”

I looked at her with fear mixed with anger. She saw that look and just smiled at me. She shook her head, laughed and said, “you DO want to get promoted sometime or another, don't you Paul? Trust me when I tell you that promotions within the company are not based on whose ass you kiss... Well, maybe it is, but there is a great deal more that you have yet to learn. And this, if you haven't realized it yet, is the start of that learning process.”
I looked at her now with a great deal of confusion on my face, trying to figure out just what it was that she was talking about. She saw that and continued.

“Yes, Paul, this is the start of the process we use to promote our assistants. And that means that Ms Tress, your supervisor, has decided that you can handle more responsibility. With that comes learning the company culture and the process begins with this. As you know, her number one assistant, Sheryl, decided that is was time for her to move along and requested to be reassigned. Of course, she is not a First Assistant any longer but did find a position as a fourth assistant with one of the other VP's. She then asked me if my one assistant would like to come over to take the open slot as her other three assistants are not up for the job.”

“My ONLY assistant really does seem interested in transferring over to Ms Tress, seeing as it would be a big jump for her. But she, in taking the position, is going to find out that it is not QUITE what she thought she was getting herself in for. And with that transfer, she can not leave that position for two years. That leaves me needing someone to fill in as MY assistant. Ms Tress, in her kindness, told me that I would find some things about you very interesting, things that you probably didn't know we knew about you. And trust me when I tell you, Paul, we know a great deal about you.”

I looked at her and was starting to feel REALLY frightened, wondering what it was that I may have gotten myself into, coming to work for this company and, everything else. Of course, I also realized that a small part of my mind was actually thinking that this might be a good thing, seeing as I was standing there, pretty much about to be... When it dawned on me that I had NO IDEA what I was about to be, actually... I was having my position with the company changed??? I was not going to work for Ms Tress but now this woman as her ONLY assistant???

“Okay Paul, I think you can put on the garter-belt and panties, then we can see just how good you are at making yourself appear feminine.”

I got redressed, pulled down my hem and went to the bathroom and pulled out my make up. I went through it all, then proceeded to clean my face yet again, using something to clean the pores and then the wonderful thought of covering up any possible beard shadow, even though I had shaved a few minutes prior. Then I worked on the foundation and started working hard on my face, neck and ears. Before I could even start to add any colors, she turned me around and scrutinized every inch of my face, pointing out things that she wanted corrected, adding a little light there and some darkness there. Then she looked at my eyes and told me to work on them first.

I pulled out my eye liner and decided that I wanted to make the eyes a little wider, so I darkened and lined my eyes. I looked at my lashes and decided rather than putting false eyelashes on I would just use some mascara and lengthen them. I took my time as it was not the greatest mascara but it does the trick as long as I am patient and cautious. Then I applied the shadow, working to make my eyes appear bluer than they were as well as larger than they were.

All that time, I could see her in the mirror, watching and nodding. When I was finished, she had me turn around and she began to pluck out eyebrow hair, causing me to jump a little and mutter the occasional “ow!” She really didn't care about it and soon she was finished, turned me towards the mirror and I noticed that there was going to be no doubt that I had feminine brow shape and size. It didn't even look close to be androgynous but definitely super model thin... And the brow change mixed with the colors I used definitely said something. I looked down and saw the lip pencil and started to put that on, followed by using a brush for my lip color. In minutes, I was all done and pulled out the setting power so that it all stayed in place, as it were.

I then noticed the time on the clock again and realized that I had just spent an hour working on my make up. Normally I didn't worry THAT much about it, seeing as I rarely went out in full dress, while the sun was still out, as it were. Oh, I had no problem spending that much time and I had on those occasions, like Halloween, when I could go out dressed up and get away with it.

Then I stood up and picked up my wig. Since I had long hair to begin with, it was nice to fill out the hair I had. But since I also had a little thinning problem on top, I had to use a wig rather than just extensions. But the wig color was very close to my natural hair so I usually didn't have to worry about covering it all up. I would just brush my own hair into the wig and use a few bobbie pins to hold it in place up top. I did this and then turned into the mirror to look at the final product.

As I looked, I saw the reflections of two women looking back at me. I was dressed fully where as she was only wearing her panties, stockings and a beautiful satin corset, all in black with some red accents. When I looked at her feet I saw that she did have on heels, almost as high as the ones I had on. And I realized that she was not all that short, as even with the slightly shorter heels, she was still very close to looking me in the eyes.

“Well Paul, I certainly hope that you can get that face on faster than that. But I have to admit, if you can make yourself look this good, I may allow you that little extra time for putting your face on. Now, help me with my dress and we can go and get something to eat.”

“Oh, and realize, Paul, sweetie, that I am going to be paying CLOSE attention to you and how you comport yourself while we are out there. If you are good, maybe I won't have to discipline you too much. However, I am quite prepared to make sure that you know what you are doing.” She laughed a little before saying, “by the way, that trip to Reno and the little cross-dressing ranch thing you were going to... Well, I guess you should know now that, although it is indeed real and is indeed going on this coming week, you will NOT be going there. Since we are the ones who run it, we figure that you might rather spend time with me, learning how to be a BETTER and OBEDIENT little sissy rather than what those people are there for, just to learn proper make up, manners and mannerisms, oh and of course, spend the week dressing up like girls.”

“Besides, you are going to learn to BE a girl, not just dress up like one. And not just be one occasionally but rather, dress and live like one... Permanently”

* * * * *

Permanently???? What the hell was she talking about??? Why would she think that I would want to LIVE like a girl, dress like a girl and...

Well, okay, which of us hadn't THOUGHT about what that would be like? But now, I was beginning to think that maybe this was going a little further than I wanted to go. I admit that right now, as I was standing there in a very nice little outfit and silky undies and stiletto heels that I was feeling pretty good. That was until I felt the little cage thing locking my penis between my legs and constricting my balls so that nothing showed. But still, it only bothered me when I was feeling, well, horny... And right now, as I watched her turn her back and walk into her separate bedroom, watching her legs and ass move I was starting to feel a little something TRY to grow down there. But it hurt and I was not sure if I could figure out how to get the thing off.

“Paul, sweetie, I did say OBEDIENT! So, come and help me get my dress on.” Then I felt something sting me down below and I reached as the pain subsided. “If you don't want it to hurt worse, I suggest you come along!”

Sure enough, there WAS something sinister about that thing and I was just beginning to find out what that was. But since I really didn't want ot hurt any more, I rushed to catch up and helped her into a beautiful dress of red silk. Zipping up the back I noticed how it hugged her shape and definitely every man who saw this would be feeling stirring in their shorts. And I was certain that several women would either be looking daggers at her or else wondering how to do the same thing that the guys would be thinking. That thought was interupted by a strange little comment.

“Paul, sweetie, you might as well get those kinds of thoughts out of your head. I will tell you though that, I kind of like going both ways. But for right now, I have to worry about you and training you to work MY way. And the first thing I have to do is change that name. Paul is certainly NOT going to work when you are dressed and looking like that.” She pointed at me and ran her finger up and down, indicating the feminine attire and appearance.

“In fact, I think that I will call you something very nice, at least in my opinion. I am going to call you Lynda Christine Jamison. The Lynda is from my own middle name. And since you are going to be MY creation, that works quite well. As for the Christine part, well, I just like the name. As for the last name, well, it IS your last name... Or will be once I am completely finished with you. And the best thing is that if I train you as I want you to be, well, I won't have to give you up, since I won't LET you leave.”

I looked at her and realized that she was giving me HER last name... Did that mean that I was going to be... MARRIED to her??? I didn't think THAT was what she meant, but I couldn't help but think that it might be something LIKE that...

“Okay Lynda, sweetie, it is now time to go off and seek some delicious food. But before we leave, one more LITTLE thing to take care of.” She then produced a satin object and walked around my back and placed it around my neck. I then realized that it was satin covering... METAL! And before I could say anything, I felt something snap four times behind my back. I reached my hand up and felt the collar around my neck and realized that it looked like a satin choker but was really a very PERMANENT collar aound my neck. When I looked in the mirror I saw that it was black with white ruffles at the top and bottom. But was frightened me the most was that it said, in bright pink scripted letters the word “sissy” on the front!

“Oh Lynda, I didn't say that we were going to some FANCY place where you could be my equal and eat with me. You are going to be allowed to eat and it will be at my table. But this is Vegas and, well, there is a nice little private club that we are going to be going to that serves really good food and you will be able to eat as well. You will even get to eat at my table, though you won't be sitting in a chair with me. That chair is reserved for the client we are meeting tonight. He is the reason for the papers you brought with you. And, well, you will be given your first REAL assignment. And from now on, you will call me “Mistress” in public and in private. Do you understand, Lynda?”

I stood there, not comprehending what was happening. I was... Being trained??? This was sounding more like a very thought out fantasy but I was experiencing it as a definite reality. And I comprehended that if I didn't listen to her, I would suffer. When I realized this, I bowed my head a little and replied, “yes, Mistress.”

This pleased her as she smiled at me and she lead me out of the suite. Off we went to the car and opening the door for her, she sat in the back of the car as I drove off. Our first stop, however, was to another hotel where there was a gentleman waiting at the curb. I looked in the mirror as he waived and I realized that he was flagging us down. She nodded and I drive up to him. As I put the car in park, I saw that he was waiting for something and I realized that I had to get out of the car already and open the door for him. So I unbuckled the belt and got out, walked around the front of the car, letting everyone see me and opened the door for him. As he got in, he remarked to the woman, “Nice little sissy you have there, Nicole. Nice legs and definitely a nice little ass!” She laughed as I closed the door, feeling a little heat come to my face as I heard people laugh and even one or two wolf whistles as I got back into the car. Then I was told where to go and after about 20 minutes of driving we arrived at some out of the way place and I parked the car.

Of course, now I knew that I was supposed to open to door for them so I hurried up and opened her door as it was closer to the door. They both got out of the car and I followed them through the door and noticed that she was greeted by someone there as if they knew her. She pointed out the client and then pointed to me and we were led to a table that was set for two and a pillow on the floor. In an instant I knew right where I was supposed to be and knelt there on the pillow. The two of them started talking business and placed their orders for dinner. I knelt there, waiting, wondering what I was going to be eating when I felt a pat on the head and a bread stick was handed to me to eat.

This went on for a while, watching as she worked the client, talking about this and that. I also noticed that his trousers were getting a little tight between the legs and that twice he had to reach down and adjust his pants. Since I had kind of tuned out the conversation, since I was just there as the “pet” as it were, I didn't think that it was all that important that I pay too close attention.

I did hear my name, “Lynda” mentioned a couple of times, as I felt another little pat on the back or my head. I even heard the word sissy and a scarey word, “slave” once or twice. But I did start looking at some of the other tables around this place and noticed that I was by far NOT the only one kneeling someplace in this establishment. In fact, there seemed to be a great many others kneeling at tables. Both beside and UNDER some of the tables. And when I saw that and WHY they were under the tables, I realized that there was definitely something happening here that I was not too sure that I was going to like all that much. A little shock to my crotch brought me out of my little wanderings and had me looking up. “Yes, Mistress?”

“It seems that you have had your mind wandering, Lynda. I am not happy with that. But of course, looking around and seeing so many others like yourself, kneeling on the floor with their Masters and Mistress' and some of them even worshiping them intimately must have made you wander. Or were you getting nasty little sissy thoughts in your head, maybe? Like taking care of Mr Perkins here, who right now has a nasty little boner that just seems to need some devoted and delicious attention. And seeing as you are right here, just waiting for your Mistress to reward you and I find you actually being a bad little girl, I guess that maybe you need to learn proper manners. So I think that instead of worshiping your Mistress to thank her for the lovely time and dinner, I think that you should appologize to Mr Perkins so that he doesn't think that all of our employee's are as stupid and ignorant as you are!”

I noticed that she had something in her hand and I realized that it was the button to the device that she had been using to punish me or gain my attention, as it were. And I also noticed that, as I looked over to Mr Perkins, his pants were now unzipped AND he had this wide grin on his face. I knelt there, wondering if maybe this was some sort of nightmare but realized that there were a couple of things here that made me realize that it was reality.

One was the beginning of a little current flowing into my groin area that was starting to hurt a little. Another was the collar around my neck that was adding a little weight to the situation, to say the least. But my own mind was ALSO involved in this, telling me that not only had I fantasized about being forced to suck off some guy by my Mistress, had even wrote about it somewhat in an online site, it was all becoming the embodyment of this fantasy I had. And before I really thought about it, I crawled under the table and wrapped my red painted lips around this strange mans cock and started to pay close attention to it with my tongue and lips. I closed my eyes and thought about all the things that I would have liked done to my own cock as I sucked and licked him. I could hear him moan lightly and could even feel some energy eminating from him as I brought him closer and closer to orgasm. Just when I thought he was about ready, I felt two hands grab my head and pull me closer to his sweaty and stinky crotch. Then I felt and tasted his hot cum spewing into my mouth and I knew that I had to swallow it, though part of me was fighting that.

I finally swallowed it and like a good little girl, I milked his cock dry. When I was done, part of me was disgusted at what I had done and yet, there was another part of me who had just realized that I had fulfilled a fantasy. My Mistress had ordered me to suck off some guy and I obeyed. I would have preferred to maybe pleasure my Mistress instead, but I realized that if I had been paying attention as I was supposed to have, I would have had that opportunity. I also realized that this chastity thing I had on would not be coming off any time soon since I was not as attentive as I should have been. I just hoped that whatever was supposed to be worse was not in my future.

“My goodness, Nicole, that little sissy of yours seems to be a natural! Not even some of those high priced sluts working some of the brothels and cat houses do it THAT well. And I should know, since I have been to all of them at one point in time. Of course, maybe I should go out to that one that you just opened up over just north of here. The one I think called 'the sissy farm' or something like that!”

“Frank, it is called 'The Sissy Dude Ranch' and the people out there, the girls and the gurls, are NOT out there to suck off some guy just because he flashes some money in their face. Well, I can't say that they WOULDN'T suck you off for some cash but that is not what they are there for. Hell, Lynda here was actually going to be going there this week, playing at being a girl for a week, learning things that we try and teach up there. But she made a decision... Well, we made it for her I guess, that she would instead become one of our corporate girls. And seeing as you actually hijacked Sheryl from Ms Tress, you should be quite happy with yourself. So you can go ahead and take that little contract of hers and enjoy her as you will. Hell, maybe she can suck your cock just as well as Lynda here did.”

“Nicole, it wasn't I who stole Sheryl from you. You know it was Jennifer, my, well, my senior VP that took her from you. Of course, imagine her surprise when she found that she couldn't get her out of her little chastity harness without killing her. So when I called and found out what it was going to cost, Ms Tress told me what we had to do and now, we can do it. Of course, a five year exclusivity contract that we will only use your products in our firm at slightly elevated prices was going a little far. But since Jennifer wanted Sheryl as her, umm... Anyway, you have the contract and we can conclude our business.”

“Yes, I realize that it wasn't you who stole her. But it was you who she went to see and it seems that maybe you were trying to serve two Mistress'??? Either way, she is now yours, or Nicole's, to do with as she pleases. Our business is now complete and from now on, you will have to deal directly with Ms Tress. And I am sure you know what that will entail, Frank. Just make sure that you behave properly or else that contract for five years could turn into, well, something longer... And unless Nicole has THAT control, which I know she doesn't have right now, well...”

“Thanks, Nicole. For the contract, and the, umm, well... You know what I mean. Have a good evening.”

With that, the gentleman left the table and I was left there with a bunch more questions than I had answers. And the biggest question was...

What had I gotten myself in for this time???

 

18.09.10

story continues in Working Vacation 2

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