My Journey

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.

Of course, at first, I did all those things that young males will do, then having to clean them up and try to put them away without my mother knowing what I had done. Plus, of course, having a brother there didn't help out too much either. And, to be honest, I got caught several times. Thankfully, I never really got caught being tied up, but I did get caught in her underwear. I think that the worst time was when she actually made me dress up in front of her.

If I had been honest with myself then, as well as with her, imagine what life could have been like. If I had told her that I wanted to be a girl, would that have happened? If I told her that I had been tying myself up in bed and was really enjoying the feeling... You get the idea...

But I mention this because, well, it may have started me off on the journey that I took that got me to where I am now. I admit that when I look back on it I should have realized what was going to eventually happen to me but, in all honesty, I never realized that such things could really happen in life. But, seriously, I guess that I was relieved when it happened and, to tell you the truth, it is probably the best thing to happen to me.

After I graduated from high school, I went into the military. I have to admit that even that didn't knock the feminine side of me out. But it did, depending on how you look at it, fortunately or unfortunately, expose me to the little known world of S&M... Or B&D... Either way, I learned that there were those women out there that were willing to tie me up, whip me and other little things along those lines, because I wanted it... Of course, it wasn't like they were offering this for free, but it was such a strange eye opening experience that I started to wonder. I also discovered magazines, mostly old Harmony Publications, showing women bound, gagged and such and, instead of wanting to be the one tying them up, I wondered what it would feel like to BE those women. I am sure that many readers will agree that we all have had thoughts before, and still do, if we are honest with ourselves.

Of course, fear would set in and I would write a letter and not send it out, for fear of whatever there was out there. I did eventually write to a couple, a Dominatrix by the name of Mistress Destiny comes to mind. I actually recall talking to her one time on the phone and was amazed at her voice and such. Unfortunately, I had never been able to get to Detroit, where she was and I never found out what happened to her. Of course, there was also this Mistress Michelle who lived in the same area. However, looking at her photo's scared me a little and, well, now I know it was more for effect and all but it still scared me back then.

In time, I eventually faced my fears and went in search for a local Mistress. The first time I was there almost scared me off. I went the 90 miles there, worrying about everything, realizing that I would finally feel the satisfaction of my submissiveness and feminine feelings all at once. Well, everything that we talked about fell to pieces, I felt more humiliation and disgust and went away feeling bad. I never talked to her again. And I sat, on the sidelines, looking but afraid to reach out.

Of course, I also had purged everything I owned and then wanted it all back. We been there and done that, at least once in our lives, right? Well, After the second purge, I realized a couple of things... I can not change me... AND, I need to find someone who is willing to take me by the hand and lead me along that path that I still felt I needed. But I really had no idea of how to find that person to lead me along the path... America On Line got me started... Amazing how that worked out back then... At least it wasn't Facebook!!! (By the way, you can't find anything on Facebook... LOL)

Anyway, I was bored and started looking in the personal sections on AOL. This was when you actually logged into THEIR server and had to do everything on the phone line... Remember those days. And after many hours of searching, I found a woman there that was actually looking for someone who wanted to learn. Gee, imagine that. So, I emailed her and she had one of her submissives email me. After a little while, I finally got the opportunity to meet with her, in public, of course.

We got together at a little coffee shop and we talked about this and that. Actually, everything that we talked about seemed to be of a vanilla variety, at least at first. I think it was to see if we would be comfortable with each other. Imagine how scared I was, sitting there talking to this woman I had never met and only sent emails to for a few weeks. I was afraid, since I was also remembering the first time I had served someone. But I started feeling comfortable with her.

She asked me what I did for work and a bunch of other trivial things. But eventually, we got down to the meat of the matter. She asked me if I liked to dress and if I was wearing anything then. I blushed a little and told her that I was. That morning I had put on my black satin garterbelt and stockings, along with some black panties. I couldn't wear a bra, seeing as it would have shown through my clothes. She even asked me if I had high heels, which I told her I did and that I was actually proud that I could walk in my five and six inch heels.

When she asked me if I knew how to properly clean a home, I honestly told her that I was not sure, as it was something that I had never really done. When she asked me if I had the proper uniform, I admitted that I did, indeed, have a French Maid uniform and that was when I saw her really smile.

I was given directions to her home and told that I was to be there the following week, fully dressed to serve as her maid for the day. I was to be there, clean shaven, in stockings and high heels. If it was cold out, I was to wear a jacket. But if it was nice, as it was then, no coat. That scared me a little as I was realizing that I was going to be dressed while driving. I admit that I had driven many times, AT NIGHT, dressed but this was not only during the day but also in my maid uniform.

However, when she looked into my eyes, I knew that I would do this. I realized that I was going to be able to finally experience something that I had only fantasized about. And I was really craving this, like a smoker does at times when they first quit... Yes, that bad!

So, the night before my trip to her home, I made sure that the car had a full tank of gas and that everything was alright with the car. I did NOT want to break down while driving and have to call AAA to help me. Then I made sure that my uniform was clean and that all my necessary underwear was clean and ready to go. I even made sure that my seamed stockings were new and clean. I took out the pledge and even polished the patent leather on my five inch stiletto heels. Then I set my alarm for an EARLY hour, like 5am. I wanted to make sure that I was shaved and properly turned out for my first meeting with her.

The alarm went off and I woke with a start! Then I realized what the day was and I felt a little tinge of fear mixed with anticipation. So off to the bathroom I went and started the bath. When it was full, I stepped into the tub and layed down inside it. I let my body soak a little then proceeded to make sure that my chest was shaved, as well as my legs and underarms. I debated shaving my arms but realized that I couldn't do that because of how it would look to the people I worked with.

When I was done, I dried off and spent a good half hour trying to do a decent job on my face. I knew it was not perfect but I felt that it might pass a little bit. Then I started to get dressed. This took a little time as I was shaking nerviously as I put on the breast forms. I used the spray on medical adhesive and was worried that I would get them wrong. But I got them on and put on the bra. I then took out my cincher and put that one, attaching the garter straps to my new stockings. Then I put on the ruffled panties and the petticoat. I slipped on my heels and put on the uniform. Lastly, I brushed my hair out. Seemed like a dumb thing to do since I had to put the wig cap on but it helps to keep everything smooth when I put on the wig. Then I pulled the cap on and picked up my auburn wig. I had brushed it out the night before and I ran a quick brush through it again before I pulled it on and used a couple of bobbie pins to hold it in place.

I stepped back and looked at myself and realized that I really SUCKED at make up. I was so hoping that this woman would be able to help me on this, since I really wanted to look far better than I did. But I sucked it up and went down stairs. When I looked at the clock, I saw that I had an hour before I had to be there and it was going to take me only about 15 minutes to get there. I looked out and saw that it was clear and I took that chance. Carrying a purse and with my keys in hand, I managed to get to my car without being seen. I started it up and decided to take a slightly longer route to her house.

It still only took me about 20 minutes to get to her home and I saw that she had a nice home, not totally secluded but still offering some privacy. I looked and drove around the block and saw that all the homes seemed to be the same. I finally drive up to the house and pulled my car to the side of the house. I got up the courage and got out of the car and walked up to the door.

Just as I was about to ring the doorbell, I saw the note on the door.

“Come around to the REAR door”

I turned around and walked to the back of the house and found the door. I looked but did not find a doorbell there but I noticed that there seemed to be an intercom near the inner door. So, I opened the door and walked into the house. I pressed the button and waited.

When she arrived at the door, she was surprisingly plain. She did not dress as one would expect a Dominatrix to dress. In fact, she was in jeans and a blouse and I could see the outline of a plain bra through her blouse. The only thing that came close to being Domme like were her heels and those I couldn't really see more than the toes.

“Come in and then drop your panties, sissy!”

No good morning... No courtesies... And drop my panties? I stuttered as I walked in but felt that there must be a reason for this. So, in I came and I reached under the petticoat and pulled down my panties. I was afraid to say that I was so scared that my penis was soft and small... And here I was, exposing this short coming to this woman.

“Good. Now, because I am a married woman and my husband, who knows what I do and has no problems with men coming to see me, I have assured him that those who come to see me are not allowed to have sex with me. To this end, I make them wear this little device.” She held up a rather mean looking thing that I only could guess at the purpose. “I am going to lock your penis inside this chastity device. This way, if you DO get any ideas, you will be unable to act on them. Plus, this way my husband knows that I am faithful.”

With that, she reached down and quickly locked my penis away in a small little tube. “Be thankful that you are getting this one, sissy. One of my little subbies has one that, well, he has not been allowed to take off for the last five months! Of course, that sissy is my current maid who is off this week. So, you are going to be her temporary replacement.”

I pulled my panties back up and realized that I was indeed going to be cleaning. But before I did that, I was shown the rooms I would be cleaning. It was going to be a daunting task, as it was pretty much the upper floors of the house, as the basement, she told me, was off limits to me. So, I proceeded to take the cleaning supplies and went upstairs to the second floor and started my work.

Cleaning while wearing five inch heels is not difficult. It IS painful after a while. And what was even worse is that I had actually volunteered for this. But I also knew that I wanted to do a good job for her since I was so hoping that maybe I could get to be tied up, maybe whipped (I didn't realize that I would like it then) and whatever else it might feel like to be submissive to this woman. I didn't know WHY I felt this way, I just know that I did.

After a little while, she came up as I was finishing the upstairs bathroom. She informed me that it was lunch time and that I was welcome to have lunch with her. She turned and left me standing there, not really knowing what to expect. But I picked up everything and brought it with me down to the main floor, where I knew I had some cleaning to take care of. I didn't see her down there but I was surprised to see a man there in the kitchen. As I was thinking about it, I realized that it must be her husband. Of course, I didn't get too much of a chance to say anything as I heard him tell me the same thing I heard when I first came here.

“Drop your panties, sissy!”

Now, of course, I knew who he was. So I pulled them down and he looked and saw the chastity.

“Gee, I guess she is going easy on you. You must be the new sissy. Interesting, though I am sure you know you look like shit. But I am sure that Mistress Martha will get you trained properly. For right now, sit. Mistress Martha will be down shortly. She has to prepare for a couple of clients coming. And I have to get back to work but wanted to have lunch first.”

He handed me a nice salad and as we started eating, she came down. This time, there was no mistaking her outfit, not that she was demanding AND sexy all at the same time. I managed to remember that I should probably get up in the presence of this woman and did so, earning me a laugh.

“Sissy, you have a good deal of training to endure. But at least you had the good manners to get up.” Then she sat down and we all ate in silence. When we were finished, I went off to take care of the dishes as they spoke in low tones. I cleaned the dishes and started to clean the main floor, starting with the living room.

“Sissy, I want to discuss a couple things with you before we continue this afternoon. I realize that you are something of a novice but, well, your face needs to be worked on. I will show you what to do and you are to practice this between now and the next time you come here. I can not have my sissy maid looking like a train wreck!”

“Thank you, Mistress” I was so relieved that I would finally get a clue as to the PROPER way to apply make up.

“Secondly, while you are not perfect at this, you are doing a good job at cleaning. Make sure that you wash the inside windows and the sills. I am a stickler for cleanliness and I like my home that way. My maid took months to learn the proper way to clean and the fact that you seem to be starting off a little better than she does is certainly good for you.”

“Thank you, Mistress!” I was shocked to see that I was doing something right, already.

“Now then. What we are going to do first is get you looking proper. You will be answering the door to my guests and, well, if you look like shit, it would reflect on me.”

With that, she led me down the hall to a room that I would become familiar with, a dressing room. In it, there was a make-up table and some lockers. Most of them were locked but some had no locks on them. She walked over to a cabinet and pulled out a fresh make-up kit. Then she sat me down and started to explain everything she was doing and making sure that I could see the effect that each step had. In about 20 minutes, I actually looked like a girl. Okay, a little slutty girl but it was certainly a much more feminine appearance than what I had started off that day with. When she was done with that, she put the kit in a locker and handed me a key. Then she went to the cabinet again and pulled out another box.

She walked over and opened the box. Inside the box was a set of pink patent leather cuffs and such. She pulled out one set, with a chain attached to them and put them on my ankles, locking them in place. Then she took out another set and as I put my arms out in front of me, she placed the cuffs on my wrists. Then she picked up a collar and placed it around my neck. Then she pulled out a ball gag and had me open my mouth. It was placed so far into my mouth that I felt slightly uncomfortable. But it didn't mess up the job she had done on my make up and I figured that was the reason.

“Okay, now you will finish up the living room. When the first guest arrives, you will answer the door, curtsie like a good little sissy maid and then lead them into here. Then you will continue with your chores.” I nodded my understanding.

“There will be three guests coming this afternoon and into the early evening. You will be proper and complete your work. My husband will also be coming home. You will, of course, curtsie to him as well. When I come into the room, if you are standing, you will curtsie. If you are sitting, stand up and curtsie. Anything else, you can figure it out.”

I nodded again. I was still trying to figure out all of these feelings I was having.

“Now, get your chores completed. Then, if you are a good little sissy, I may actually let you experience some playtime.” I nodded a final time and then headed off to get the chores completed. It wasn't long before I heard the doorbell ring. I placed my cleaning supplies down and went to the door, worried a little but realizing that, well it wasn't like whomever was at the door was someone I knew and that they might be as shocked as I would be.

I went to the door and as I opened the door, curtsied and let the gentleman come into the house.

“A new maid? Damn, Mistress must be tough on you little sissies! You are the fourth one to answer that door. But you certainly look cuter than a couple of them.” I blushed a little, realizing that if he had only seen me the first time I got here, he would be saying something completely different.

I led him to the changing room and, as instructed, left him to do whatever it was he needed to do there while I continued working. I finished the living room and started on the dining room when the second guest came to the door. This one didn't really say anything to me and as I led him to the changing room, I realized that he was looking at me and I wasn't sure but I thought he was checking my ass out. Part of me was worried and yet a part of me was kind of thrilled.

By the time I had finished the kitchen, Mistress' husband had returned and was showing me how to fix dinner when the last guest arrived. I led him into the changing room and continued working on dinner and set the table. I set it for two, as I figured that Mistress and her husband were not going to be sharing their dinner with me. When he came into the dining room, that thought was corrected, politely. I was to be sharing dinner with the two of them. This was nice but I also realized that playing was not really going to be an option since the day had been full of work and, well, no one had really said that I would get played with. I guess that is what was meant by no strings housework. Not that it bothered me at the time, but I was feeling a little disappointed. But I also realized that, well, I did get to fulfill, although only partially, one of my little fantasies, being a maid. Okay, I was dressed as one of those little slutty french maids we all hear about, but I had been working as one for the day, which was rather enjoyable!

And yes, that chastity was a little bothersome, but I realized that, well, sexual contact was not what I was wanting, though there were times when I had wanted to at least give myself a little pleasure. And pissing sitting down was definitely different.

We ate dinner and Mistress looked over to me. “I realize that you really didn't get any play time with me, but I am sure that you will understand that after three sessions and all, I am a little tired. What I would like to do is have you come again, clean house and, if there is time, maybe then we can get a little play time in. Would that be alright with you, Paul?”

I was thinking that she was talking to her husband there and having been called “sissy” all day that I didn't realize that she was talking to me then. It took a second for me to realize that both of them were looking at me, waiting for my answer that I actually blushed a little at my own confusion.

“Yes, Ma'am. I'm sorry...” I saw them both smile at me. When he spoke, and I had not really heard him say much of anything the entire time I was there, it threw me for a loop, as his voice was low and soft. “It's okay, as it has been a rather different kind of day for you. You will need to be here again on Wednesday morning, and EVERY Wednesday morning. We would like to see just how well you can be trained.”

I nodded and then Mistress started to talk.

“Now, what I want from you, Paul, is to be here each Wednesday morning, no later than 7am. You need to be completely dressed upon arrival, as you were this morning. With that, I also require you to be made up as I instructed you. So that you know, you will still have to wear a chastity when you are here. I am sure that you will have no real issue with that. In time, I may decide that you are worth going further into your training and transformation as my little sissy maid.”

I sat there, realizing that I was being told that they wanted me to return, which really made me feel good. “Thank you, Mistress”

“Okay, stand up and we will remove the chastity.” I stood up and pulled down the ruffled panties and Mistress reached in and unlocked it. I pulled up my panties and Mistress then removed the cuffs and the collar from me. I kind of felt weird when I didn't have the collar. After a few more moments, we bid each other a good night and off I went back to my place, noticing the fact that it was dark and that I had been there for far longer than I thought. I got into my apartment and removed everything, taking the uniform and putting it into the drier along with the best invention for those who hate taking satin maid uniforms to the dry cleaner. 30 minutes in the drier with the Dryel kit and my uniform was cleaned. My undies went into the washer and off I went to bed.

It was a rather odd week, thinking about the upcoming Wednesday, working my regular job and counting the hours each day as I waited for the day when io would return to Mistress Martha's home. But finally, Tuesday night arrived and I got everything ready for my trip back to her house and my chance to be her maid again.

That morning, I woke up and spent the time getting all ready. I was so thrilled that I pulled out my other maid uniform and got all dressed up. I then got into the car and drove out to the house. I pulled in, pulled up out back and went to the back door. I rang the bell and was let into the house by Mistress.

“Well, I see that you did pay attention to my make up class. And I love the cute little pink maid uniform. But I guess we should get everything taken care of.” Mistress pulled out the chastity and without being told, I pulled down my panties and she put it on. I was then put into the cuffs and collar and sent off to clean as I had the week before.

This time, Mistress' husband was not there. I was now required to make lunch each Wednesday that I was working there. It was a good thing I was paying attention that day. And each afternoon, Mistress would have “clients” come to serve as her subbies as I was cleaning her home. And as each passing Wednesday came and went, I wondered where this other maid was, since each time I came out there, the house needed to be cleaned. Not that I cared, since I was there cleaning and playing the little maid all day, wondering if there would ever be a time when I would get to “play” as the subbies who came out to see Mistress. Of course, I also realized that they were paying for the pleasure of serving Mistress and I was cleaning her home. Of course, that might also be paying for playing though I wasn't playing. Well, if you think about it, I was playing and having fun with it.

The coming out each week went on for about three months until there was a change at the end of the day. Well, it actually kind of changed that morning when Mistress put on my chastity. This time, the chastity was a little more severe than I had been wearing all that time before. I didn't think too much about it really until the end of the day when I thought I would be getting it off.

“Yes, I want you to continue wearing that chastity. While I realize that this is something that you were not expecting, I want you to wear this chastity until next week when you come here. And I want you to wait until Friday to come here rather than the usual Wednesday. Now, before you get all confused, this is what I like to call a limit stretcher. I want to see if you are worthy of going even further than you have these last few months. I also want to see how far you are able to trust me.”

I stood there, wondering if I could actually do this. I was actually wondering if I could take wearing this thing, which was far more restrictive than the former one. And I was thinking that this might be, indeed, something that I was not totally willing to do.  But I also realized that this was, indeed, a test for me.

I nodded my understanding and saw Mistress smile. I was sent away to suffer not just a week but 10 days wearing this chastity. It was the longest 10 days in my life as I went through the weekend and worked the entire week up until Friday morning.

I managed it though and was feeling rather, well, horny at the time, seeing as I was unable to touch any part of my cock while it was in there. But Friday morning finally arrived and off I went, getting dressed up and ready to go to my fun work...

 

 

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19.01.13

story continues in My Journey 2: Ten days later...

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