(story continues from My Journey 2: Ten days later…) Part 3: The Final Decision When I woke up, it took me a little while to figure out where I was and what had happened to me. I did notice that I was not wearing anything other than my lingerie, meaning that at some time, Mistress and her husband had removed my clothing. The chastity device was still on my cock but the dildo, as I realized, was no longer inside me. ...
Waking up, sometimes, can be rather difficult to do, especially when you know that you were drugged the night before. Or, at least you HOPE it was only the night before. And this time, it was far worse than the first times. So many things have changed about me from the first time I was drugged, unwittingly and unwillingly, though as I look back, I can’t really say that I am upset about the outcome of each of these times. Well, I have to admit that I was, kind of, pissed off the first time, as I never really expected something like that. But that was quite some time ago and now, well, I guess it was all for the best. ...
“But honey, I’m not a woman!” Of course, the line that I heard after I said that the first time was to be my eventual downfall. When my wife looked at me and said, “Well, you seem to be DRESSING like one!” Of course, it wasn’t like I was planning on getting caught. And I certainly didn’t plan on getting caught in the manner in which I was. But those were now things of the past. But I guess that I should explain how it got to this point, where my little line certainly would not explain the way I look NOR the way I dress. ...
“So, what ever shall I do with myself with all this free time off,” I thought to myself. I had just seen the wife off to work and my work had been on a slowdown. Of course, for those of us who are into cross-dressing, this is the time when you can just go all girlie and enjoy yourself. Of course, it does help if the wife has no issues with you dressing up. ...
I always enjoyed getting out there on the open road, driving my car and taking in the scenery. And I have to admit, the day that I got my convertible, it was a totally different kind of feeling. Of course, being a guy, you aren’t supposed to like cute things or enjoy the scenery, right? But looking at the girls while driving is always something that a guy is supposed to do. But since I like to dress like a girl, I look at them for different reasons… Well, maybe for MORE reasons than “normal” guys. And in a convertible, things are so much better. ...
(story continues from Fantasy B&B Part 3) Part Four Of course, I was lying there, scared as hell as my new Mistress started to feed me her menstrual fluid, and all I could think was to keep my mouth closed so as not to take it in. This turned out to be a very bad idea as I realized why my body was being bent as it was. For as it started to flow and lead it’s way to my mouth, I felt a very painful blow to my genitals, since they were raised up for easy access to a riding crop. As I opened my mouth to scream out in surprise and pain, the first taste also hit my lips and entered my mouth. And I heard a shout, “You had better swallow, slave, or else this will certainly be a long day for you, dearie!” ...
It isn’t everyday that we get an opportunity to find out things about other people that we would never know. It’s even more interesting, or scary when you think about it, when they learn something about you that you would rather others NOT find out about. However, sometimes the two of them come crashing together completely accidentally and, well, there is nothing that you can do about it but, well, survive. ...
(story continues from Beauty Makeover… And then some) Part Four I realized that there was a time for fantasy to stop and reality to set in. I was kneeling there, dressed as a very sexy maid in a satin uniform and wearing silky and sexy undies, stockings and stiletto heels and I was, indeed, wearing a collar and cuffs, WILLINGLY! That was my reality! There was no longer a fantasy aspect to all of this because I was now experiencing this for REAL! I got up on my knees and opened my mouth, not speaking a word because I was afraid that I would say or do something stupid to ruin this final submission of my body to Cindi. Then I bent over at the waist, to signal that I was completely willing to submit to whatever it was that Jennifer and Cindi wanted of me. “Lynda, I see that you MAY have made a choice. I can also see that you are afraid. But I want you to know that I want to hear your acceptance. Do you indeed WILLINGLY submit to Jennifer and myself?” I was shaking a little. I could feel it in my hands and knees. I was also sure that it showed to them. But I knew what it was that I had to do. “Yes, Mistress, I am willingly submitting to you and to Mistress Jennifer!” “Really? So, you are now recognizing me as your Mistress, slave Lynda? You see yourself as my slave, Mistress Jennifer’s slave or both? I am rather curious, Lynda.” I knelt there on my hands and knees, wondering what it was that I had just gotten myself into. I was willing to submit to them but they wanted to know WHY??? Or to whom? I was now somewhat confused myself. “You are my Mistress. You were the one who placed this collar around my neck, which I willingly let happen, placing myself under Your control, Mistress. This is certain. You asked if I was willing to let Mistress Jennifer use me as She saw fit and I understand and accept what that means. Since she is also Your friend, would she also be called ‘Mistress’ as well?” I took a deep breath… " ...
(story continues from Working Vacation 2) Part Three Of course, the problem was that I still had to survive this first night and already I was sore and wanting rest and true sleep. But after having sucked and dildo fucked, I still had to get back up and walk more in the heels. But now, I was being followed and corrected as I walked, being told how to walk like a lady and not like some guy in a dress. I had never had problems walking in heels but apparently I had been doing that wrong for as long as I have been able to stand and walk in them. And realize that I am walking with a short length of chain connected to my ankles so my problem was not so much taking shorter steps but more along the lines of my posture. I was slouching a little and after all this time, feeling tired and the like, I slouched. But that was improper and Nicole and Catherine, along with the others, decided that maybe I needed a little help with my posture. ...
I was traveling for a week on the road, checking things out and not having to deal with all my various employee’s. I am a regional supervisor and many times work from home and occasionally go out to check up on the work of my people. I can do this one on one or, as I had planned this week, following behind my people to make sure that their work is up to par without telling them I would be doing so. Sort of like leaving them to do their jobs but making sure that they really are. I decided that I could do this AND indulge in my favorite little hobby, dressing up enfemme. Of course, I also knew that if I did, given how masculine I looked in the face, that I would have to limit myself to night-time dressing and maybe taking a little drive in the car rather than spending all day enfemme, which I can do when I am working at home. Still, I figured I could at least enjoy some time. ...
Part One I am traveling today, finishing a three day run to visit with the people that work for me out in the field. Each have their own things they have to do, and they rarely see me out in the field, unless there are problems. This week is just a get out and touch hands kind of week, but it does allow me to go out to places and become my feminine self. One day, I was reading one of the little contact mags in the adult book store and I saw an ad for a little B&B out in a direction that I would need to be going out to sometime in future. So I wrote down the number and location, and saw that they did have a website, so I wrote that down. When the time finally came to get out that way, and this was way off the beaten path when I looked at the map, I figured that it would be a nice place to go to. ...
(story continues from Fantasy B&B) Part Two I start to walk to the hallway and when I peek out into the hallway, I can see others doing the same thing I am, starting to walk out into the hall, slowly, as if not expecting what is going to happen next to them, as that is how I was feeling. When I get totally out of the room, I hear the door shut behind me. I turn and see that there is no knob on this side either. I happen to look on the floor and see two foot prints, or actually what would be two high heel prints on the floor and I figure that is where I need to be standing. So I move there and face down the hall, in the direction the prints seemed to be pointing. I look ahead and see others looking around, and when a couple notice what I am doing, they see me gesture to the floor with my eyes and head, and they catch on and find the marks on the floor. Then we hear a door open behind us and the sounds of high heels coming up from there. “Well, sissies, I guess you are not all that stupid, as some tend to be in the beginning. I am Mistress Angela and I am the Head Mistress here at the Joiner Academy for Sissies. Many years ago, Madeline Joiner started a B&B for sissies to indulge themselves in, and then realized that some of the sissies wanted or needed something more. So She started this academy. Sissies do not request to come here, necessarily, but many want to be here. But many do not want to end their time here, for in the end, they are sold off to the highest bidder, and the bids do get rather high, and they no longer get to enjoy their time here as they are now slave’s to their new owners. Their new owners can be men, women or both even. There are the occasional She-male owners, but not too many. We do have them as your trainers though, as we also have women here for your training.” “Now, the first thing that you should know here is that it is rare that an owned slave comes here, but we have that privilege this time. It is the only one wearing a collar that can not be removed. It’s name is sissy, which seems rather aptly named, though it has a middle name, slut, so I guess we will have to call it sissy slut so that we can call it out individually when necessary.” “Next, you will be given a meal and then be taken to the instructional room where you will learn the rules for this Academy. There is no dismissal from the academy, just punishments that will make you remember not to misbehave in the future. Take the time to learn what you need to learn, and you will survive the academy. If you do not learn, you will suffer and may have to become a prostitute rather than a sissy slave to your new Mistress or Master.” I listened to the Mistress and all I could do was think back, wondering who she was referring to as being my owner. As far as I could see, I was indeed the only one wearing a permanent collar with the name sissy on it, and wearing a charm between my breasts that said slut. But I was afraid to say anything for fear of being punished, and I did learn a little something in the military, in that you will learn more by listening and paying attention than by asking questions at the wrong time… ...
(story continues from Fantasy B&B Part 2) Part Three “Did that feel good, sissy? I am sure it did, and you will get quite a few more of that, but first…” then I felt the dildo slide out and something else being placed in it’s stead. Then I felt it expand and start to vibrate, which elicited a moan from my mouth. “Oh, sissy likes them big, huh? Well, this will be even better for you then!” as she took a large penis gag and locked it into my mouth, and I could taste that is had some cum on it. ...
I can remember those care free days of my youth, when I was just a kid playing dress-up. Of course, playing dress up as a guy putting on my mother’s underwear and actually ENJOYING it was and still is slightly frowned upon in the “vanilla” world. And I have to admit that I started rather young, as we all seem to do, at a ripe age of about 10. Of course, it was not very often, since I did have to go to school and had a baby-sitter. But there were those times. ...
(story continues from My Journey) Part 2: Ten days later… It was a good thing that I had work to keep me occupied. It left me less time to worry about what I was going to do and whether or not I would be willing to wear a chastity device. A small part of me was worried and yet, there was that little voice actually telling me that maybe by wearing the device, I would actually start to feel those feelings that I had WANTED to feel. All I knew is that I was gradually getting more and more curious about all of it and finally decided that I would NEED to see her again. ...
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. ...
(story continues from Working Vacation)_ Part Two Nicole looked down at me and smiled. “Get up, head over to the bathroom. And yes, you are to use the one marked for “sissy’s”, as they do have one for you. When you get back, sit down on the chair and eat something food related. Then we can have a little chat” “Yes, Mistress!” I got up and walked over to the restrooms. I found that there indeed was one marked “sissy” and went in. It was bright pink (YUCK) but it definitely had everything a sissy would want, including small individual bottles of mouthwash (YEAH!) and other little things to help you clean up. I opened my pocket book and pulled out my lipstick and touched it up. That was the only part that was really bad. That and I had to use the facilities. ...