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Sissy's Saga

Author: 

  • Maid Joy

Organizational: 

  • Title Page

Audience Rating: 

  • Mature Subjects (pg15)

Taxonomy upgrade extras: 

  • Crossdressing
  • Posted by author(s)
  • 17,500 < Novella < 40,000 words
  • Identity Crisis
  • Fresh Start

Sissy's Saga

Drawn from real life, this is the story of one person who is reclaiming the word "Sissy" and making it a name, not a title. A middle aged soldier trapped in a life he hates because he was trying to fit in. Now it has come to a point where he can't stand it anymore, and is trying how it might feel to have what he wants instead of what he's supposed to want.

One Sissy's Story -- Pt 1

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Femdom / Humiliation
  • Wishes

TG Elements: 

  • Maids / French Maids / Servants
  • Sissies
  • She-Males

Permission: 

  • Posted by author(s)

This is not autobiographical, mostly. I wrote this to see if I could write a story with no dialog and have it be good. It's a story, it has no dialog but I leave it to you to tell me if it is good or not.


One Sissy’s Story -- Part 1

Maid Joy

It felt like hearing nails on a chalkboard all the time. There was something fundamentally wrong with the whole world and I didn’t know how to fix it.

It had always been like that. Like I was trying to fit into the world that didn’t want me. I would look around and see kids playing with each other and I would try to play with one set of my friends, only to be rejected, told by my parents that I didn’t do that. I would be pushed toward other friends and told to play with them, only to find out that I didn’t fit in those games either.

Smaller, weaker, not as athletic. It was always like that.

I knew what was wrong. I was different. Always had been. When I was allowed to achieve I was stellar. But when I was forced to conform, I failed.

Take the incident in Middle School. They had a Home Economics course that was offered for the girls to learn to be wives. So I went and took it. People thought it was odd that I was in there, but I passed it off by pointing out how many girls were in there, and the guys got jealous. In there, I achieved.

I could sew. I made clothes in there, better than most of the girls. I made my pillow, so well that I still had it 20 years later. I made the stuffed animal from a pattern. I knew almost instinctively what the various pieces were for and how they fit together to make the three dimensional figure. I was a perfectionist, the seams had to be fine and exact. I knew what the various seams were for and how to change out the foot on the sewing machine.

I cooked. I made meals. My cookies were the best in the class. I was the only one to realize that the pie crust had to stay COLD to keep the butter from melting all over, to make it too sticky to work with.

My teacher was so proud of me. She thought the whole concept of my being in there, the lone penis among all those vaginas to be cute.

Cute. How I came to loath that word.

My parents divorced when I was 15. They actually were separated since I was 12, and the divorce wasn’t final until three years later. So essentially I was the man of the family. Not even able to grow pubic hair, and I was the man of the family. My mother and three sisters were all looking to me to run the family like a man had to.

All I wanted to do was to put on a skirt and live.

I put on the apron to keep my clothes from becoming splattered and stained with tomato sauce when I made spaghetti and I heard the cries of how cute it was. I saw nothing wrong with having a gingham plastic apron on, but apparently it was cute.

I’ve always adored red gingham since that cooking class. I would get there early so I could choose that apron and no other out of the fifty aprons available at Home Ec. It felt so right to have that one on, like it was a missing part of my life.

But looking like a pizza table was apparently cute to the girls. I heard that over and over. So of course the boys picked it up.

It was like that any time I tried. Aerobics, Parenting Class, eating at the main table in the cafeteria, participating in ballet and trying out for the Drama club. Apparently going and joining the book club was considered cute too.

I knew what the word really meant, cute was another word for sissy.

That is what cute came to mean in my head.

My grandmother was looking in my room at one point and she said that I and my room were cute. She meant it in the sense that all grandmothers mean it, as a compliment to the childishness of the room, but to me, it was a blow to the gut.

I looked around and decided that she was right, it was a sissy room. I had dolls, the full sized GI Joe action figures that you can’t find anymore, but more than that, I had a couple Barbies as well for Joe to rescue. I had my stuffed animals, treasured companions of my youth, who had seen me through all kinds of problems. They were the only ones who knew about the stuff at school. I had my lamps which were pink since Mom was buying three for $2 for my sisters, and I just grabbed one.

I guess the thing that made my room cute was the white comforter with geometric patterns that looked like flowers if you squinted right, in pastel colors. But it was warm and I needed it for winter. Coupled with the mostly white pillowcases, it did look like a Sissy’s room.

That night I had a bad time. Called sissy by people at school, hearing my grandmother’s voice, hearing that hateful word over and over again, it was too much.

I woke up in a cold sweat. I decided to figure out how to be the boy everyone wanted me to be. I had no clue how to, but all I could do was try.

I woke in the morning and decided to start to un-cute myself. I started with my room.

I couldn’t bear the thought of throwing out my friends from when I was little, so I carefully put them in a plastic garbage bag. I wasn’t throwing them away, I was preserving them. Perhaps my children would love them. The lambs, the Lion, the Bears, my most treasured flopsy Annimal (with the conscious pun chuckled at by everyone). Barbie and her friend Tracy, the stupid girls who always got in trouble and had to be rescued, carefully put into shoeboxes with their clothing. GI Joe and his other soldiers put into their footlockers with their clothes. The sets put away, the curtains taken down, the comforter folded up and put in the attic. It broke my heart each time I did this, but it was necessary.

I got out the bedspread that was made for me out of a large piece of denim. That should be non-cute enough. There was nothing I could do about the lamp right now, but I could put up the posters that I had hidden away due to lack of interest.

Over the next four hours my room went from cute to stupid.. While I can appreciate good German Engineering in a car, I fail to see what makes it so sexy. Talking about cams and horsepower and so on bored me silly. A car was a car. So that one was called a Mustang, and the other was called a Yugo. They were both vehicles that transported you from point A to point B. That was it.

Now I would have to study these things. I couldn’t stand it.

I was no longer cute. I was surly. Fifteen years old, from a broken home, T-shirts, ripped jeans and more, and the only way I knew how to act was surly and mean. Everyone accepted that. But it was like wearing my pants backwards, having my shirt on my head, or putting the mittens on the wrong hands. I could exist with this, but it felt so wrong.

I became popular for some reason. The worse I treated people, the more people liked me. I ignored girls and they flocked around me. I picked on the weaker boys and I had the respect of my peers. I wanted to cry.

I could talk for hours about drive shafts and carburetors, about paint schemes and what Disc Brakes were and how a McPherson Strut was important. I kept grease under my nails.

Because it was expected of me, I had detention about once every other week. I was generally in trouble for having hurt someone at some point. I was stoic about it and spent my time looking at girly mags. I told anyone who asked the reason I was looking at them was because of the good lookin’ wimmen, but it was really because I enjoyed thinking about what they were wearing. But that couldn’t get out.

My school counselor decided that I needed to learn some sensitivity. She added a class in Parenting to my schedule.

While I was totally thrilled to be in a class to learn to take care of babies and how to be a good parent, I had to pretend that I didn’t want to be there. So I sat in the back, ignored everyone, doodled and tried not to be noticed.

But my doodles were actually notes to myself. I needed to learn this and how biology worked and how things fit together. I’d leave the class and my crew would be right there with me, and I would make fun of everything I learned, and not doing too well in my classes. You know, it’s hard to intentionally fail a class you like.

My teachers despaired of helping me. One told me that I would be in jail if I didn’t change soon. I couldn’t tell him that I had changed and it made everyone like me this time. I couldn’t tell him that my attitude kept me from the sports teams, that it kept me out of Boy Scouts (G_d save me from that), that it preserved the illusion that I was tough. As long as I acted like this, no one questioned that I would quite willingly hurt them in a fight if I had to, so no one messed with me.

If they only knew.

Here I am in the Army now. Somehow I’ve locked myself into a life I can’t stand. One that feels like I’m wearing a pin-suit, being stabbed all the time. If I stayed absolutely still, I was okay if uncomfortable. If I moved, I felt pain from every part of my body.

I wasn’t cute anymore. I was tough. I was rough. I was macho. I knew three ways to kill you with just my fingers, and if I had a pen, G_d help you. I had volunteered for duty in the Rangers to make sure I wasn’t cute anymore. Not that it was a worry.

I had missions to go on, bullets to shoot, people to kill. I had territory on a map to secure and men to command. I had no girl, I kept losing those relationships. I wasn’t gay for I wasn’t attracted to any of the men but I couldn’t keep a real relationship with girl for longer than a week. I had no one to go home to. I spent the nights alone, or with a paid companion who didn’t care for me at all.

I would look at their outfits and wish.

Fantasy is one thing, reality is something completely different. I knew I looked like the typical GI Joe, but I really wanted to be Barbie. While I wasn’t muscle bound like some I knew, I was cut and buff. Could you see me in a dress?

I could. It wasn’t pretty.

Bulging arms, cut legs. I wanted lean legs, smooth legs. I wanted supple arms, I wanted breasts, not pecs. My lats and delts were exposed and would show and possibly rip the clothes they were in.

I had a few things that I held, things that I looked at and imagined myself in. There was the beautiful pink prom gown stolen from my sister. If anyone in the NCO Quarters asked about it, I would get silent and sullen. I didn’t lie and they drew the conclusion I wanted them to of a vanished girl.

The delicate lace and thin satin was heaven on my skin, it made me feel so good. It caressed me and I knew that it is what Heaven was like. Sometimes I’d sleep with it in my bed with me. Just me fondling it and hiding it caused seams to pop and lace to split. Putting it on was out of the question.

A gorilla in a dress. That was a pretty picture.

I tried everything to get past this need of mine. I wanted to be cute. But I was so insecure about myself; I didn’t know how to be what I wanted.
And each day I felt the dream slipping further and further away.

Finally unable to take it anymore, I went to one of my paid companions and found a name. I thought about it for a long time before making a call.

I passed over $2000 to a woman I didn’t know, and whom I didn’t want to know. It was for a full weekend, one that I hoped would make me happy.

She ordered me into a skimpy little maid’s outfit, hose and shoes. Size 13 heels, could you believe it? She made my face up, pinned a wig on what little hair I had and made me take care of her. Curtsey, serve tea, get dinner, run around, break my ankle falling from the 5 inch spike under my heel, spill and be punished. Oh she was good at punishment. Any little infraction, any little thing and I was spanked.

I hadn’t been spanked since I was 10. But my ass stayed red. About half way through the first night, I caught sight of myself in a mirror. I looked like a clown. Candy Apple Red lips which were too big for my face, corpse white foundation, electric blue eye shadow, and fake lashes that would make a Drag Queen jealous. My huge chest bulging out of this tiny bra barely covered by the top of the dress, and my harry legs showing through the fishnets.

I looked ridiculous and I knew it.

She snapped an order at me, and when I failed to move quick enough, she started spanking me again. But this time, the tears weren’t from pain.

I was the sissy I had always been. It didn’t matter, all my attempts to fit in didn’t matter at all. I was a sissy and I always would be.

The rest of the weekend was simply me enduring like I did in Basic Training. I did what I was told, didn’t think, didn’t talk back, accepted my punishments as I was supposed to. I cried a lot. And every time I wasn’t crying from the pain. I was crying for what I lost.

But I kept the panties. I’d look at them occasionally and cry silently.

No one ever found out.

Reclaiming the Sissy -- Pt 2

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Voluntary
  • Fresh Start

TG Elements: 

  • Jewelry / Earrings
  • Sissies

Permission: 

  • Posted by author(s)

This is a continuation of my previous story "One Sissy's Story". I couldn't leave it so hopeless, so my night time almost asleep muse attacked and made me write this. I hope you like it.


Reclaiming the Sissy -- Pt 2

Maid Joy

My weekend was over. Part of me was relieved and part of me was disappointed.

In my time just being alive, I had heard the term “sweet torture”. I had never truly understood what that particular phrase meant, until I had my first weekend. After that time, I took the panties back to the NCO barracks and kept them. During inspections, I would wear them so that the First Sergeant wouldn’t find them.

I came to understand how those times were sweet torture. I enjoyed wearing them. I hated having them on because I couldn’t have them on all the time.

But now, my weekend was over.

I knelt in front of the Mistress I had paid again to dress her sissy up and make hir serve. She was looking at me while I contemplated the shine on her boots. I could have done my make up in that shine, perfected after all my years in the Army.

“Why do you do this to yourself?”

I wasn’t quite sure I heard the question, so quietly it was spoken. “Ma’am?” I asked.

“Why do you keep coming back to me to do this to you? This is your fourth time here, the fourth time I have humiliated you like this. Most macho men would have run after the first time. You aren’t getting sex from it, you haven’t cum once that I know of, which is why most men do this. So why do you keep coming back?” Her voice wasn’t the cruel lash it normally was, it was gentle.

I cautiously raised my eyes to her collarbones. She didn’t react. In my peripheral vision I could see her expression, and she was curious. She studied me.

I shrugged my shoulders.

Her response was quick. Her voice hardened. “Don’t shrug your shoulders at me, missy. You know why you do this even if you don’t want to admit it. Look inside yourself. Tell me.” Her tone left no room to argue.

I dropped my gaze again. “I don’t know. I truly don’t. I deserve this, I guess?”

“Do you like punishment?”

“I can take it.” I stated.

Acid frosted her tone. “I didn’t ask you if you could endure the punishments and pain. I know that you can. Do. You. LIKE. To be. Punished?”

Defeated I said “No Ma’am.”

“Do you like being humiliated?”

I wasn’t quite sure what she was asking. My brows came together and I started to look at her, but stopped myself in time.

She continued; “My specialty is to humiliate submissives. To do that I use a variety of tools. I make them feel bad, I insult them, I make them question every aspect of themselves. I question their sexuality, I hurt them, I dig into their emotions, and I do my best to break them down. But I can’t really get you to let go.

“I have made you cry several times from the suffering I caused you, but you haven’t broken under a lot of mental strain. I can attribute some of it to the humiliation you went through in your Basic Training and your Advanced Individual Training for the Rangers, but not all your mental fortitude. You are a puzzle to me.”

I didn’t know how to respond to that. I wanted to shrug my shoulders again, but I knew that this would make her mad. I shifted my position slightly to keep my feet from falling asleep.

“Ma’am, you are right about my training, it prepared me for a lot. I found that I lost the capacity to be embarrassed because of that training. Given some of the things I have been through, you are accomplished in your art, but I’ve literally been through worse.” I stopped for a few minutes to collect my thoughts.

She waited for me to start again.

“I come here because I can be in a dress and it is acceptable here. It is inexcusable in the life I have, but here, it is normal and expected.

“The first time you had one of your lady friends over and I had to serve you both refreshments, I was mortified. I hid it and tried not to let it get to me. But it did. I was blushing, especially from some of the comments you and she shared. I didn’t allow that to stop me.

“But through it all, even though you and she both tried your best to get me to break down, insulting me and my masculinity, neither of you thought it odd for a male to be in a maid’s outfit. That was a normal part of this world. Showing my legs and being in heels, walking strangely and swinging my hips, that was just part of the backdrop. It is no more strange than to have me in a uniform, or you to be in a corset, or for a girl to be in a skirt. That is what I want from this.”

She considered this for a while. She wasn’t like many people who when confronted with a silence rushed in to fill it with sound. She sat, and she sat still. She didn’t move or fidget, she simply let the chair hold her while she rested on it and thought.

“So you are telling me that you pay my outrageous fees to simply crossdress?”

I only nodded.

She took a deep breath and let it out slowly. “I wish you had been up front with me about that in the beginning of our business relationship. Normally men wanting to be in dresses need to be humiliated for that. It satisfies a deep need to make it shameful, and if it is shameful and forbidden, that makes it erotic to them. Failing that, they want the pain, the little masochistic sluts. I’ve seen all types, including cross-dressers, but you may be the first that wasn’t embarrassed by it, to whom cross-dressing wasn’t shameful. Why is that?”

I didn’t want to think about it. I wanted to ignore the question. I knew she was waiting for an answer, and I really didn’t want to share it with her. I closed my eyes to keep from thinking about it.

I heard a slight movement, which I identified as the heel of her boot scraping on the floor. There was a rustle of cloth and the movement of the skirt in front of me. Then I felt quite a bit of pain from my genitals as she stepped on them.

“I asked you a question, sissy.”

I squeaked “Because it feels right, Mistress.”

The pressure let off, and the pain subsided, but the tears were rolling down my face anyhow. The pain was actually nothing; it was the question that hurt so much.

It took her time, but she managed to drag my story out of me.

I told her about my childhood. I told her about the taunts. I told her about how I loathed the word ‘cute’. I told her everything. The reactions she had been trying to bring out of me through humiliation and pain, came with he deep seated fury of the life I was living.

“Mistress, please understand. I am not macho, although many would call me that. This is an act, a façade I put on to cover myself, my true self. I feel like a girl, all the time. When I look at myself, I see breasts and a vagina, long hair and rounded features. I look in a mirror and this alien being of muscles and testosterone stares back at me, and I don’t know who that is.

“I am a soldier because I was FINALLY accepted as a person by being this way. I don’t want to be this way, I don’t want to hurt people, I don’t LIKE killing, but everyone expects it and they approve of me.

“I’ve seen myself in a dress and makeup, I know I look hideous. If I saw someone like me on the street I’d laugh and point and be repulsed. I don’t want to have that happen to me, it would kill me. Being seen in public like this, looking like this... FREAK that I am mortifies me. There is no way I could look beautiful as I see myself, as I know myself to be.”

I lost it, I started crying. Bronze Star, 12 confirmed kills, Expert Marksman with a rifle, and I was blubbering like a baby on the floor. I hoped this was a bad dream that I would wake up from.

I felt her next to me. She picked my head and torso up from the floor where I had curled in the fetal position. She pulled me into her lap.

Then she started rocking me while I cried. I didn’t know how to react, and I cried more. My whole body was shaking and vibrating. I couldn’t stop crying.

She petted my hair, wiped my eyes with my apron. She rocked me and stroked my head and arms. Nothing sexual, just a girl comforting another girl who had a bad time. And still I cried.

I twisted around so that I was facing her, my head in her lap, and my face in her belly. There was no desire to do anything, and the comfort was helping.

She kept rocking and now she was humming a bit. She wasn’t saying anything of substance, just little nonsense things, things you might say to a child to get them calmed down. She rubbed my back some to help.

My shoes had fallen off my feet, my makeup was ruined. I was pretty sure I had run my stockings at some point, and I was cold. My bladder was bursting with the need to pee, and I couldn’t breathe out my nose. But still she was patient.

I finally wound down into sup-sups, and stopped crying because I just couldn’t sustain it anymore. She kept holding me.

After a few more minutes of comforting me, she let me go, and she helped me up. She took me to the dressing area and had me get cleaned up. The stockings went into the bin to be used as restraints at some future point, and I put my maid’s uniform into the wash to be cleaned. I looked in the mirror and I saw that my makeup had smeared all over the place. I honestly looked like I was wearing primary colored camouflage and had fought with a makeup kit and lost. Raccoon eyes were the least of my problem.

I used a rag and several hands full of cold cream to get all the makeup off. I washed and scrubbed my face, eyes, mouth, teeth, hair, neck and so on. There wasn’t an area to take a shower, so I skipped that for later.

I dressed in my civies and came back out to leave. I found Mistress standing near the door to the cars, wrapped in a cotton nightgown and robe. She prevented me from leaving.

I was led into her personal kitchen, the one that was in the attached living area. There I was sat down and she served ME tea. I felt absolutely miserable.

She started talking to me, about simple things, how I couldn’t breathe, how she had seen grown men cry, but rarely with such force. She was gently teasing me about the snot that was on my face before I cleaned up and so on. She was making light of the situation, but I knew she was trying to defuse it as best as she could.

She explained this stage to me, this was called “aftercare”. It was the time where it was up to the responsible dom to take an emotionally fragile person and let them recover hirself before they hurt hirself. So for now, I was her prisoner again, while she made sure I wasn’t suicidal anymore.

When I focused on what she was saying again she was talking about the whole Cross-dressing issue. “In my line of work, I make it a point to make people humiliated, as I told you. Had I known you simply wanted to be a girl for a while, I wouldn’t have put you in that hideous makeup I did. It was an intentional ploy to humiliate you. However, I thought I was doing right.

“So, tell me how much leave you have still before you have to be back on base?”

“It’s a 72 hour pass so I could spend this weekend here, I have to be back on base no later than 0700 tomorrow.”

She glanced at the clock. “Okay, it’s only 6 PM right now. We have some time. You and I are going to talk, and ONLY talk. There is a lot that you have to work on and I think I’m just the person to help you do it.

“First off, I want you out of that Uniform. Come with me.”

She had me get up and led me back into the changing area. But when I stripped down, this time she put me in a completely different set of clothes. A nice calf-length dress, in a beautiful dark blue, made of washable silk. Oh, it was heaven on my skin. Panties, bra and breast forms to fill out the cups, long sleeved so that my arms were hidden, two and a half inch heels, and a slip were all soon on my body, and they felt... right. More right than the maid’s uniform.

She stepped back and looked at me for a moment. She reached over to a series of shelves and pulled down some wigs that had not been in evidence until then. Very soon a long red wig was settled on my head, and this one wasn’t nearly as scratchy as the others she had made me wear in the past.

“This beauty set me back $800. But you pay for quality real human hair. It’s so well designed that you can’t see the over all color strands, red, brown, green yellow and grey, only the over all color of red. It’s my favorite and I have to ask you to be careful with this.” While she was saying this, she was pinning the hair up and keeping it out of my face.

“I would have you shave your legs, but that would cause you problems with your CO. So for now we will ignore them, but shaved legs are luxurious and you should try it once if you have an extended time to do this.”

She had been applying cosmetics to my face. A little here, some there, a swish to this area. She picked up the biggest and softest makeup brush I had ever seen and ran it all over my face. She then dunked the bristles in some powder and did it again. Lipstick applied and I was done.

She stood back and looked at me. She then got into the bottom drawer and pulled out some boxes. “Open this box and try the rings on. I want two skinny rings on your right ring finger, one thick ring on your left ring finger. Try to make sure that it doesn’t look like an engagement ring.”

Once again, saving time she had been pulling out some necklaces and a few other things. Soon I had a thin gold chain encircling my throat, hanging down on my chest outside my top. Clip on earrings came next, and a few pieces of jewelry to go in the hair.

She stood me up and looked me over. She walked around and looked closely. “You’ll do.”

Taking me by the hand we went over to the three way mirror. It was dark because the lights in this area had not been turned on yet, and she spent a few seconds adjusting the mirrors. She then stepped over to a switch and turned it on.

“Meet your new self.”

I saw the girl in the mirror drop her jaw at something she was looking at. While she couldn’t be considered beautiful, handsome was an adjective that worked. She was very conservative in her dark blue dress with the gold chain glinting in the light....

Blue dress? Gold chain? Wait, that was ME!

I looked closer, and I soon discovered it WAS me. The makeup was all wrong, you couldn’t even really tell I had any on. No clown face, just wide smoky eyes, slightly pinked up cheeks, probably from embarrassment, a frosted set of lips and all of the beard covered. I couldn’t believe what I was seeing.

My gaze traveled downward, and yeah, I was filling out the dress top like I hadn’t before. The bra straps were pulling into my shoulders, and I was a little off balance. The hair curled down and accentuated the little breasts, almost framing them in a halo of auburn tresses. The waist narrowed just where it should and while there weren’t much in the hips and ass department, it still looked somewhat feminine.

I looked at Mistress. I had absolutely no words to say.

“I pronounce you, a girl. You look pretty good too.

“You don’t have any legs because of the exercise program you are on. They look buff, but not shapely. Padded panties can give you a shape in your lower area and we can do something to make that annoying bulge in front totally disappear, but with a full skirt on no one should be able to tell that you have anything other than a large vulva.

“The hair has to go off your legs. Until then, tights will be what you need to wear. Your nails have to be done, because nothing says ‘girl’ like a set of nicely shaped and painted nails. The makeup came out spectacularly. With your tight waist and your shaped abs, you won’t have a problem fitting into most dresses, but unfortunately, the clothes you wear are going to have to be very conservative; high necks, long sleeves, long skirts.

“But once you leave the Service we can work on making a few permanent changes, like piercing your ears and shaving your legs.”

I had to sit down. My head was spinning and I couldn’t think. Never in my life would I have thought I could look like this, given everything that had gone wrong in my life.

Maybe things would be good after all.

Sissy's Release -- Pt 3

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Intersex

Permission: 

  • Posted by author(s)


Sissy's Release -- Pt 3

Maid Joy

"Now that you are dressed properly, come and we will talk."

I had some trouble walking in lower heels than normal, but I manfully (ha) managed to navigate from the changing area to the kitchen again. My head was still spinning from what I saw in the mirror, but I would have to deal with it.

Mistress had me sit. My impulse was to jump up and to serve her, as I had been, but she insisted. I was treated as her lady guest, and I didn't know really how to react. So I put on my best manners and accepted what she wanted to give me.

Tea was first, followed by some dinner. I didn't eat much since my nerves insured I wasn't hungry. During the meal there were occasional noises of disapproval, and when I heard them, I tried to figure out what had caused it. Most often it was me slipping back into my male role and forgetting myself.

Mistress finally broached the subject that had been on my mind, and probably hers as well, when we were relaxing with a final cup of tea. Coming right to the point she said, "You have a lot of problems to overcome."

I nodded my head, not trusting my voice to speak. My chin went down in shame again, but she instructed me to raise my head and look at her. "I'm not trying to keep you in a submissive position, but you are unique to my experience.

"Most often strong men who have very powerful jobs, like CEOs or Army personnel, come to me to be abused for feeling feminine. It is a way for them to release the stresses of being the one in control and to let others take that control for a while. But I fear I erred badly with you."

She fell silent for a few moments while I tried to understand what she meant. I understood the release of power for the powerful, I had felt that same release after a session here, but I don't know how she could have made a mistake.

Her voice had been changing accents for a bit, slowly but steadily going from her normal "British Domme" cadence to something that could have come out of Georgia. That accent threw me back to many days in bars there in Columbus Georgia at Fort Benning.

Oh, those Georgia Peaches were beautiful and sweet. I had been ragingly jealous of them, at the same time I was envious of their clothes and make-up. Conversely I wanted to dominate them, humble them, and make them beg for what ever I wanted to do to them, to make them feel the way I did inside. I also wanted to dominate them, not as a master would, but as a boyfriend and a man would do, to hold them, protect them, caress them with a controlled gentility. I was so confused by the clash of emotions that I ignored the girls and threw myself into training.

She finally broke the silence. "Normally when I get a soldier in here, they want to be little or they want to be made to feel this is shameful. I guess your training does that, makes anything feminine bad and negative. So I give them what they want, humiliations galore," she said, quoting a line in The Princess Bride. "Naturally, I assumed when you showed up, Army Ranger, strong and handsome, wanting to be a girl that you wanted the same. I purposefully did everything I could to make you feel shamed and humiliated, from the makeup to the dresses I had you in."

I was confused, "You mean that hideous makeup job was deliberate?"

She had the good grace to blush a bit. "Yes. It was all part of the 'scene'. No real girl would be caught dead in that kind of make up, it looks tawdry and overall just bad. We really do work hard to make ourselves pretty not like a tramp or clown.." She looked at me again. "I think this makeup scheme suits you more."

She sighed deeply and let it out explosively. "I think we need to start again. Tell me, what do you want from this? Do you just want to be in girl's clothes? Do you want to be a girl? Is there a sexual component to the clothes? What can I do for you?"

I shook my head. I really didn't know.

She began asking me questions and taking notes on a legal pad while I cleared the dishes. I rolled up the sleeves of my blouse and put on an apron to protect the beautiful clothes I was wearing. A pair of rubber gloves finished the outfit. Her questions were ones that I hadn't really thought about.

Did I have the courage to tell her that all my life I had felt like the world was wrong? How could I trust her enough to say how crushed I was when I was pulled away from playing jacks with the girls and forced to the football field? Did I dare confess that when I was alone I would braid daisy chains even though I knew that was a sissy thing to do?

Even worse were the questions about how I got trapped. Why did I choose to get rid of everything in my room because it was cute? What prompted my choice in friends? Why did I want to be accepted? Who did I watch as examples of what a man was?

Above all, why did I join the Army and go out for the Rangers, one of the elite fighting forces of the American Military?

The answer to the last question was the easiest. "When I was about 16 in High School, I had still been having a problem with my perceived lack of masculinity. I would challenge people who made the mistake of questioning it openly or in rumors, and mostly by bluff I managed to get the guys and girls to back down. One day the school had a Career Day. One of the recruiters was talking about careers in the Army and mentioned the Rangers. He said 'If you go into the Ranger Training Program and pass it, you will never have to prove your manhood again.'"

I scrubbed the plate I was working on thoughtfully. "It was like a lightning bolt. I thought, maybe this time I can get past it all. Maybe I can finally bury all the questions about if I'm a man or not."

I remembered that time. The front I put up about being a punk was just that, a front. I think that everyone knew about it and just were too intimidated to question it. But I saw some glances. I saw them move away from me in the locker room where we changed. There was even one incident where a very gay boy made a pass at me. He was terrified and I was really shamed. I did something that I don't think any of the others may have done, I actually talked to him a bit. He had been dared to see if I was really gay too.

I made sure he knew I wasn't, and that I also wasn't going to beat him to a pulp, although I made him promise to say that I got really mad and threw him around a bit. I couldn't bring myself to actually beat him up. He was scared and I was scared, and he couldn't help what he was.

Truth be told, I had always wondered what would have happened if I had taken him up on his offer.

Before I knew it, I was done with the dishes and she was done with her questions. I sat down and waited.

She looked up from her notes and saw me. She smiled and laughed a bit. She pulled out her cell phone and snapped a photo of me quickly before I could protest.

I was totally confused. She turned the phone so I could see it. "I think this whole macho Army Soldier thing is just another disguise for you. When you are relaxed, see how you look?" I looked at the picture.

There I was, a nice looking face, beautiful red hair, hands folded in my lap sitting straight up, feet tucked primly beneath the chair with my ankles crossed. I didn't see anything wrong with that.

"That's not how a man sits. This is how a lady sits. I find it interesting that your instinctive behavior when you aren't trying to be Rick Ranger is that you sit like a lady. Did you learn that from your mother?"

I had to admit that I did. "Despite everything and her attempts to make me the man of the household, she treated me like one of her daughters. Her stated reason was the skills I would learn, cooking, cleaning, laundry and so on, would help me when I moved out and started living on my own. They really have helped me. I can iron better than anyone I know. So I learned things like shopping, how to buy and compose meals. I was even more confused."

I thought back to those times. "I know what is good when I shop and what isn't. I don't buy fruit and produce that is bad or unripe. I love cooking. I really, really like doing things around the household. I don't mind cleaning, and I actually enjoy children. I know how to get stains out of most clothes, and I never made the mistake of putting my Class A's in the washer with my BDUs."

We spent some more time talking, mostly about the challenges my being in drag would present.

She was very direct, "Let's be honest, while you are in the Army, there's not a lot I can do for you. I can let you have weekends here, take some time and be yourself. However, the training you do to stay in shape is the exact opposite of the body shaping you need to look more feminine. You are flooding your body with testosterone, and no matter what you do right now, you aren't going to be delicate. Right now, you are what the Welsh call 'wiry', which is their term for being made up of little but bone, sinew and lean muscle.

"Luckily you aren't too tall. If you were six feet tall, it would be even more difficult for you and what you want. There are some tall girls, but they tend to be looked at like short men are, with a little contempt. At 5 feet 8 inches, you are about perfect for a female's height. Your weight is also right where it should be, namely 150. With some padding we can make you a very nice 34, 22, 30 and I think you would look darling with those measurements. We'd have to put shoulder pads in your blouses so that your wide shoulders looked like padding, but that shouldn't be too hard."

I thought for a bit. Did I want this? It was true I was more relaxed right now than I had been in some time, but did I want to be the object of ridicule again? Was this worth it? Was feeling right and relaxed worth the mental torture?

That was the core question I had to answer.

She reached over and patted my hand. "We don't have to start tonight, another weekend is soon enough. For now, I'm going to say that I think this will help you in the long run and it is something I think you should do.

"I'll clear my schedule for two weekends from now. If you get cold feet in the mean time, let me know. I'll do my best to get everything ready so that it is a pleasurable experience for you, not a trip into a world of torture."

She had me come back into the changing area. In the process of taking me out of my clothes and hanging things up, she talked about what each piece was and how it worked. She taught me the "tuck and pull" technique for hiding my male parts, and she informed me that the panties she would have me in next time would more than cover me up, they would ensure that I didn't have an unsightly bulge where it wasn't wanted.

She took measurements of me again, making sure that they were accurate. Everything from my feet to my hair line, she got written down. I asked her why she was measuring me again, when she had done that the first time I ever came to her. She said that it was because there were deliberate errors in the measurements to embarrass me by having something that was too small or too large.

"If I'm going to have your wardrobe here, then I need to have stuff on hand that will fit you. And before you ask, yes, I intend for this to be a long term relationship and I expect you to be doing this for a while.

"How much time do you have left in your enlistment?"

"This is my second tour, and it will be up in about eight months."

"Well, then this arrangement can last until then."

The cynic I was, I had to ask "And how much is this going to cost me?"

She spent a few minutes thinking. "I was charging you a lot of money for what I was giving you. But I have to warn you that this isn't going to be cheap. I think we can work something out, if you are willing to help occasionally and to pay for the clothes and suchlike that I will be getting for you."

I nodded. I wasn't doing much else with my money. I was sending some money back to my mother to pay her back for everything she did for me while I was growing up, and truthfully to pay her for all the grief I caused her.

While I had some money, I didn’t have a lot. The money I had saved for this haven was fast running out. Her offer to shop for my real clothes and then store them for me was an amazing gift. I knew that my money would be well and carefully spent for appropriate items and that took a lot of worry off my mind.

She finished what she was doing and ordered me back into my uniform. “I think that’s going to be enough for this weekend. Two weekends from now, I expect to see you back here.”

She looked me over for a while as I got my uniform back on and took the makeup off. “I think we need to have a name for you, a good girl name. When you are here, en femme, you will be ‘Sissy’. Not to ridicule you, but to reclaim that word from the negative associations in your mind. It’s a bit juvenile, but I think it will do.”

When she called me that, my stomach turned a bit. But I started thinking about it for a little while, and I could see her point. “Yes, ma’am. Sissy will be fine,” I said, dropping back into the habitual “ma’am” and “sir” that had been drilled into me by the Army.

“Don’t say that like I’m about to cut your head off. I’m suggesting a name, nothing more. I suggest it because it is short for sister, and I think it will suit you. We can always change it later if it is too much for you, but you have all these bad memories of the title sissy, and I want to give you some good memories.”

I sat down and pulled my boots on and bloused them correctly. “Honestly, ma’am, I don’t think there is a good memory I could have of that word. It has been used too long to shame me and make me feel bad. I want to try though.”

She nodded. “That’s all I can ask you to do. Just try for me, Sissy.”

Sissy Stifled -- Pt 4

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing
  • Transformations

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Voluntary
  • Identity Crisis

Permission: 

  • Posted by author(s)

Sissy Stifled -- Pt 4

Maid Joy

I reported for morning formation at 0700. While part of my mind was on what I was doing, PT is pretty mindless. Yelling the cadence wasn’t something that took up a lot of my mental faculties. I put my body and my voice on autopilot and turned my attention to the past weekend.

There where a lot of thing I needed to consider. Mistress was correct, I didn’t know what I wanted to gain from my exploration. I knew that I enjoyed dressing up, but I also knew that I didn’t look as much like a girl as I wanted to when I finally got the clothes on. I had to make some decisions.

***

PT was finished and now for the exiting part, sitting around and waiting. My current duty station had my platoon on alert, meaning if anything went wrong, we would be the first sent to the danger zone. Unfortunately this meant there was a lot of sitting and waiting. Since we were confined to base the only training we could do was limited. Alert status means they can’t grind you into the ground but they don’t want your skills and reflexes getting flabby. We did hand to hand combat a few times a week along with firing range training and PT but that was about it.

This unfortunately gave me a lot of time to think. I said unfortunately because the military doesn’t want you to think very long or very often. So while I was sitting in offices or barracks I had a lot of time for introspection. I thought about my career in the military, what I wanted from my dressing up and what I wanted in my relationship with my mistress.

I’d be lying if I said I wasn’t attracted to her, she had made it clear that there would be absolutely no sex. I assumed this was due to prostitution laws. My blue balls were only going to be relieved by myself. Fortunately I had lots of “personal time” alone in my room. If she had forbidden me that release I would probably have gone crazy.

I had to honestly ask myself if there was a sexual component to wearing the clothes. I had to admit there was a thrill of the forbidden, but that wasn’t my prime motivator. It was a nice bonus. Most of the time while I was dressed up I wasn’t aroused at all. So when I returned to her, I could honestly answer that a sexual turn on wasn’t my primary motivation.

I knew I should be talking to one of the psychologist about my questions. I couldn’t bring myself to do it despite “no ask no tell” I knew the records of my conversations would be available to the “wrong people.” By the wrong people I mean, my commanders.

If I thought my life was hard now, it would become a thousand times more difficult if my secret were to come out.

I had a reputation to maintain after all. As an NCO I was expected to maintain an exemplary level of professional behavior with the troops I was leading. After all, everyone knows it’s the sergeants who really run the army. Even if people understood and didn’t judge there would still be some loss of confidence and respect. In a combat zone, that would be fatal. Better to keep quiet and deal with it in my own way than to know that I had caused some child to lose their father because of what I was, what I wanted to be.

Better by far to remain silent than to drag that guilt around forever.

Did I want to be a girl? If things went as far as possible, a sex change could be an option. It was the logical conclusion of this whole process. Could I bear to lose my penis and replace it with a vagina?

I didn’t know about going that far right now. I would need to take some more time to think about that.

***

Time passes quickly when you don’t have much to do. I had figured out a few things, but many others were still not clear.

I knew that I enjoyed dressing up. I liked the textures of clothes, the way they felt against my skin, how it draped and the sheer comfort of most of those clothes. Skirts were a logical choice for most times and days when it was hot. I understood kilts and how popular they became simply because of the ease of wear.

Granted, during cold days it was hell to have a skirt on, wind whipping up them and freezing parts that were supposed to stay warm wasn’t fun. It made sense that males wear skirts, what with the dangly bits being less in danger of getting squashed in a very uncomfortable way. It made even more sense that women, who didn’t have the extra parts, should wear pants with all the cloth padding the tender area of their crotches.

I went back to my room after hanging out in the squad bay for a while. I had some paperwork to do and some reviews to give. I turned on the TV in my room and let it run in the background while working.

Ignoring the noise was pretty easy, until the commercials started. They are designed to grab your attention, no matter what you are doing and to pull it to the TV. I noticed the ads. Most times, they weren’t anything I was interested in, but there was the occasional commercial that made me ache for what wasn’t.

For example, there was an ad where a mother and a daughter were walking down a beach talking about douches. I mean, let’s not pretend and talk about “freshness”, they were selling douches. The concept of cleaning yourself out with chemicals wasn’t something that I was interested in, but males didn’t do that. You would never see a father and his son walking and talking about something like jock itch! They might talk about beer while they were working on the car, but not anything of substance.

Then comes the ads about clothes. Looking at some good looking babe pulling on some jeans and wanting to have them on myself, and to look that good in them, and knowing that I never will, it really hurt. Adding insult to injury, then came an advertisement for wedding dresses.

I got up and turned the channel. I couldn’t take it anymore. Intimacy between girls, looking good, feeling divine textures, all those were the things I wanted. It didn’t matter about being taken by a man, it didn’t matter about having a vagina or having to clean out myself. I didn’t care that I would never be able to have children, none of those things mattered.

I had heard girls occasionally complaining about cramps and so on. I can’t tell you how many times I wanted to grab those girls and shake them till their teeth rattled and make them realize just how lucky they were. How if offered the chance to swap bodies with them, no matter how bad the cramps were, I’d trade without giving it a second thought.

***

My duties continued and I took care of them like I was an automaton. I paid attention to those duties when I had to, but for the most part it was just something to kill the time.

The summons to the First Sergeant’s office came as a surprise.

I reported as I was supposed to and I was invited in.

“Taylor, I have to tell you that I’ve been impressed with how you have been handling your duties recently. But I have noticed that you seem distracted. Is there anything I can help you with?”

“First Sergeant, I’ve been thinking about what I’m going to do after this tour is up. I’m not sure that I want to re-up and so I’m considering the rest of my life.”

“Well,” the First Sergeant said, “you have to consider a lot of things. As you know, the Army has been good to you, and you are an exceptional soldier. You could probably write your own ticket with the Retention people. Bonuses, promotion, choice of duty stations, other perks are all possible for you. Heck, you could change your MOS as well if you really wanted to.”

“I know First Sar’ent, but I’m really considering leaving the Army all together.”

He was quiet for a bit. While my revelation shocked him, being a career military man, I could see that he was really thinking about giving me the best advice he could. “I understand the impulse to do so, but you really have to be practical about this. If I recall correctly, you came to us right out of High School. That means that you don’t have a lot of skills for the business world. What would you do?”

I shook my head.

“There aren’t many jobs out there where you can go kill people. Ones where you can kill people legally aren’t at all common. So what would you do? Even if you don’t know, it is something you have to consider.”

I shifted my position a bit and had to think. He watched me for a little bit and then finally broke the silence. “I’m sure that if you wanted to, you could take a class for a secondary MOS in a marketable skill for the business world. It would mean you would have less time to yourself, but it would give you a skill to sell for when you get out.”

I nodded and didn’t say much of anything. He was right. “May I be dismissed First Ser’ant? You have given me a lot to think about.”

He made a few notations in the file he had in front of him and said, “Just don’t get so distracted by thinking of what comes next that you start not paying attention to detail. There’s a lot that we can help you with, but your duty to your men and to the Captain comes first. Dismissed.”

I snapped to attention and nodded to him. Turning briskly I left the office and went back to my room.

***

Two days later I was at the Training Complex and I was going through the different MOSes that I could train in. The combat arms were out, and while some of the jobs were close, like Military Police, there were some that I wanted to do, but as a girl instead of a male.

That was the problem right now, I wanted a job that I could do either as a male or a female. Mistress had promised me that it was possible to get things and do thing so that I looked female all the time, and I truly wanted that.

Unfortunately there was this whole commitment I made to my Country. As long as I was enlisted, I wasn’t free to make any massive changes. In fact, if you read the Military Regulations correctly, my body didn’t belong to me at all. I couldn’t get a tattoo. According to the regulations, anything I did to my body that the Military didn’t want me to do could be seen as “willful destruction of government property”. That could get me stuck in Fort Leavenworth for a long time.

Somehow I doubted that I would like wearing dresses there.

The Army had been good to me. I enjoyed the work and I enjoyed the physicality of it as well. It was a challenge every day. I did want to be the best of the best. I loved getting high scores on the range and I truly enjoyed reducing my time in the Confidence Course.

But a career in the Army would mean giving up my dreams of being female. Oh, sure I could be female in the military, but not a transsexual in the military. The regulations were murky at best, but that was too close to being gay.

There really seemed to be no way out of this trap.

Sissy's Debut -- Pt 5

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing
  • Transformations

Character Age: 

  • Mature / Thirty+

Permission: 

  • Posted by author(s)

Sissy’s Debut -- Pt 5

Maid Joy

I had finally decided to focus on some sort of administrative MOS. While filing and forms were a part of what I did now, there were a lot of other things that you needed to know to survive in an office situation.

I felt like a living cliché. A man who wants to be a woman, joined the Army, now studying to be a secretary. Yeah, puts a whole different spin on the “office couch.”

Reading over the regulations for the Admin MOSes, I found most of them required typing skills. I pulled out a laptop that I had received several months ago (a Christmas present from my mother). I did some web searches for typing tutorials and practice and time tests and so on. I decided to devote two hours every day to just practicing typing.

I soon found out that it was much harder to type on the laptop keyboard than on a normal keyboard. So I resolved to get a full sized keyboard and mouse to hook into the laptop for practice later.

I bookmarked those pages and started looking around the Internet. I knew that a lot of the traffic would be monitored by the Spooks, but I didn’t care. It was highly unlikely that the sites I was going to would be questionable. No one would object to a macho guy looking at pictures of girls in bikinis or in really cute outfits. Most of the porn sites were blocked, but catalogs and so on weren’t.

In the process of looking around, I found a lot of stories online. Stories about guys like me who wanted to be girls and more. I copied a lot of URLs into shortcuts and finally encrypted them all so that if my computer was searched, they wouldn’t be found. Renaming the resulting encrypted file and changing the extension so that it looked like a system file, further disguised it.

It might seem that I was being paranoid, but honestly, my big fear was being discovered having an interest in transsexuals and being ostracized by everyone I knew. I had heard of others who had been discovered to have interests that weren’t considered Army “normal”. Their lives were made a living hell until they were kicked out or forced to resign.

The way things were going, it appeared that I would be leaving the Army after all.

***

Karen had finished up with a session and decided to relax for a bit. She couldn’t wait for Sissy to come back. She wanted Sissy to shine her boots to that eye blinding shine that must be some sort of Army secret.

She made some plans to go shopping tomorrow so that she could see the kinds of things that Sissy would look good in. There had been several emails exchanged, mostly talking about fashions and things that Sissy liked.

Some were totally inappropriate. No matter how much padding she had on, she would not look good in a denim miniskirt and midriff top. There were other things that would cause problems, mostly because of the maturity factor. Club gear may be nice and look good on her, but when added to her body style now it would look like an old hooker trying to look 13.

Then there was starlet fashion. Lord have mercy, but Sissy had some very skewed ideas of appropriate clothes. At least she didn’t want to look like a supermodel, but gowns that would ordinarily be seen on the red carpet for the Oscars wouldn’t really look good on Sissy either — she just didn’t have the boobage to carry it.

Other than those fashion crimes it was surprising that Sissy had such a good taste. It was probably going to take a weekend to show her the proper way to express that style. Classic lines, conservative, earth tones with jewel accents would be really nice on her.

She took her boots off and loosened her corset until it was comfortable, and started making notes for the next weekend Sissy was available.

***

“Today we are going to go shopping. I have a pretty good idea as to what will look good on you, but now we actually have to buy things.”

She had me wear a nice dress that would be appropriate for anything from a high tea to a garden party. The blouse was kind of mannish, but the large sleeves and the full cut down to the wrists covered everything. She had me shave the area from about mid chest up to my neck; no one needs hair there.

Foundation garments came next. There was a padded girdle to actually gave me shape, along with a corset that made the lines smooth, the cups on the corset made it look like I had breasts instead of pectorals.

Now, don’t get me wrong, I was very proud of how my body looked. I had spent a lot of time developing and training it so that I could do what I needed and wanted it to do. I liked the way sweat felt after exertion and the knowledge that it was clean sweat. A real guy thing, I know.

She was suggesting that we go out to get clothes for me while I was in drag. If she hadn’t ordered it I never would have done it.

She showed me the way to pull opaque tights up my legs to cover the hair on my legs. Actually, we had to pull on three pairs so that it was smooth and fashionable. A tea length skirt with a nice half-slip completed the ensemble. She placed a pair of three inch heels on the floor for me to step into.

Makeup, wig, hair styling, earrings, necklaces (one just a simple chain and the other a heavier chain with a locket), three rings (all nice and sparkly), and finally bracelets and a watch. She pulled out a beautiful belt that was made of golden discs, laying like they were scales. She expanded it and put it around my waist, making sure that it was centered.

“Perfume and a purse is all that’s left. Any preference to the scent you will soon have on?” She handed me a couple bottles of perfume for me to smell. I recognized some names, but I had no clue what they were. Finally I found a scent that was nice and what I thought would be nice with my own scent. It was labeled “Shalimar Light”, and it had a nice jasmine scent. I loved it.

She sprayed a bit in the air and had me step into the mist. It drifted down over me and I felt so girly now.

I found that I had goose bumps.

Mistress pulled the contents of my pockets out and put them in a purse that matched the shoes and the skirt. My wallet, money, cell phone and the all-important pager were deposited into the ultimate symbol of womanhood. Mistress then proceeded to grab a few cosmetics and put them into the purse as well.

“Ready to make your debut? From here on out, there’s no hiding anymore. I’ll let you get away with not dressing up a for long periods of time, but from here on out, you are a woman.” Her eyes were misty. She took my hand. “Come on Sissy. We are going to outfit you from top to bottom.”

She walked out the door with her purse, still holding my hand. I had no choice but to follow her.

***

When we got to the mall and I felt like a whole butterfly convention had taken up residence in my guts. Nervous didn’t begin to describe how I felt. Terror on a scale that I had never felt before would be closer.

I was terrified of the ridicule from people who saw me. I didn’t feel that I could ever pass for a girl, and having others make fun of me for that was the worst thing in the world.

But Mistress dragged me into the Mall, and I didn’t have much choice. I was hyper aware. It was worse than the first time we did Night Ops. It felt as though my skin had been sanded. It seemed I could feel not only people looking at me, but their emotions and their very breath.

It was almost an out of body experience.

I didn’t look at anyone in particular, and I had to fight to keep my gaze up and in front of me, but I could see people around me looking at us. There were many who looked directly at me while passing, and there were others who looked at Mistress.

I could hear my heart in my ears. If I held my hand out, it would be shaking like an Aspen Leaf in a high wind.

There were some who looked at me and had an appraising look, and they were the girls. I can understand that, they were comparing me to them. Honestly, I was doing that as well. It didn’t matter that they were genetic girls, I was still doing this anyhow.

Then there were the men. Most of them just looked at me and kept looking, up and down my body, boobs and legs, sometimes the ass. Their eyes felt like their grubby hands groping me. It was not a sensation I enjoyed.

I wondered idly if this is what other girls felt like when I looked at them. If so, I would have to think about how I related to them in the future. That’s probably one reason that I couldn’t keep a girl.

Then there were others. One or two of the people looking at me would look at me, then do a double take, then smile and go back to what they were doing. It happened too many times to be coincidence. My heart plummeted into my shoes. I don’t remember much of the shopping trip. There were highlights, but most of it was a dizzying montage of me trying on various clothes, changing, shoes, purses and dresses.

***

Dragging Sissy out into the world was relatively easy, she wanted to be seen. Just like any other girl that I knew, she wanted attention. I honestly thought I would have to fight her more.

I kept a stream of chatter going so she was distracted from what was happening. I didn’t count on her ability to multi-task however. I tried to retrieve her attention, but it wasn’t any good. She was much better at surveillance than I was.

I saw her chin come up as she noticed people looking at her and noticing an attractive girl. But I also saw those who made her. It made my heart sink, but it was something that she would have to deal with.

I kept her going and kept her attention on me.

The nearest store was the Victoria’s Secret. I knew a couple people in here and their discretion could be counted on no matter what.

I spotted one as I came in. “Jamie, I need your help. This is Sissy and we need to get her everything.”

Jamie came over and quickly appraised Sissy. I knew that she probably spotted Sissy’s genetic sex, and that didn’t faze her at all. She smiled and took Sissy by the hand.

“Sissy, it’s wonderful to meet you. You and I have a lot in common already and I’ll be more than pleased to help you today.”

I knew that Sissy was in good hands now.

Sissy's Interlude -- Pt 6

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Mature / Thirty+

TG Elements: 

  • Corsets
  • Jewelry / Earrings
  • High heels / Shoes / Boots / Feet
  • Shopping

Other Keywords: 

  • Out in Public

Permission: 

  • Posted by author(s)


Sissy’s Interlude -- Pt 6

Maid Joy

Mistress had turned me over to a lady at the lingerie store. I didn’t know how to react. Part of me was mortified, part of me burning from embarrassment, and part of me was reveling in this chance that I had always dreamed of.

The people who were in the store weren’t really paying attention to me, which was a relief. I could only imagine the panic if someone realized that a man was in here.

I tried to relax, I really did. I couldn’t stop shaking in fear of discovery. I was nervous and I couldn’t get my jewelry off.

“Honey, calm down. It’s okay, no one here is going to hurt you at all. You are a customer and that removes half the problem from the clerks. The rest don’t care. Just as most men don’t look at each other in the shower, most girls don’t look at each other when changing.”

She showed me to a changing area that was fairly private and had me strip. She looked a bit disappointed when she saw the hair still on my body, but she measured me anyway. Jamie was really professional in that she didn’t ask the obvious questions.

Finally I couldn’t stand it anymore. “So how do you know Mistress?” I asked.

Jamie was quiet for a few moments while she considered my question. “I used to be a client of hers.”

I didn’t continue the questioning given what Mistress’ specialty was. I filled in some blanks with what I knew and made some assumptions. I hate making assumptions and so I spent a bit looking at Jamie closely. If she had been born a male, I couldn’t tell.

She caught me examining her. “The surgeons did a good job, didn’t they? They better have given how much I spent going to them.” She continued measuring me while she talked. She continued to talk without prompting. “I started going to Mistress a long time ago. I had always felt better in skirts, but I always had to sneak wearing them. That set up associations with feeling ashamed and so on.

“I heard through the grapevine that Mistress did the feminization of girly boys, and I wound up going to her to find out what it was like to actually be girled up properly, and boy did I learn. I worked really hard to overcome the shame associated with my dresses and the fear that went with it too. I finally managed to find some people in the BDSM community who did transsexual transformations and I stopped going to Mistress at that point. But she knows me, I know her and she knows I can be discreet as she needs to be.

“So, while we try things on, tell me about you.”

Over the next hour while I tried on bras, panties, girdles, corsets, waist nippers and other foundation garments, I shared what had been happening to me with Jamie. There wasn’t a lot to share since I was just starting on this journey, but what there was I told. She helped me to define what was relevant and what wasn’t in my life in regards to my wanting to be girl.

“It’s good that you are finally starting to define what you want and who you want to be,” she said at one point, “but realize one basic fact; you will be happier being who you are rather than who you think you should be. It took me four years to realize that, and many psychologists and therapists. It was a long, painful journey for me. But when I got to the end and finally decided to be myself, my true self, it was such a load off my mind.

“Now, tell me what you think of this padded girdle. It gives you actual hips and a butt.” She was very good at continuing on with the sales while dispensing advice.

When we finished getting the basics out of the way, Mistress brought over several dresses and blouse and skirt combos. “Why are there no pants or casual outfits?”

“I don’t want you confusing being a girl with the clothes. Men wear pants. Women may have pants on, but most crossdressers who are in pants walk like they are male, mainly because of the way the pants feel on them. I want to constantly remind you of who you are and what you are choosing to be while with me.”

I changed into a different outfit, a nice large peasant blouse and a broomstick skirt. My heels went well with it and we left there to continue through the mall. I made sure to get Jamie’s number. I gave her mine, but had to warn her about calling me. She promised to let me initiate contact with her.

We visited a lot of stores that day. After the specialty shop with Jamie, Mistress and I went to a jewelry store for things like clip on earrings, necklaces, bracelets and various necessities of fashion. Then we wound up in a luggage shop to pick out some huge “mom bags” for all my stuff. I only allowed one of those to be purchased however, since they were almost prohibitively expensive. I ask you, why in the world does a store charge $250 for a bag that probably cost $15 to make and sell?

But Mistress wouldn’t let me get away with just that. We went to a shoe store where soon four pairs of shoes wound up being bought. Two bags, smaller this time, were added to the mixture.

“Mistress, we just got this bag,” I said waving at the huge handbag. “Why do I need more purses?”

“Sissy, that big handbag is for every day. It is for casual and out and about running errands. It is for carrying your wallet, makeup, tissues, papers, checkbook, cell phone, a brick, mace, rubber chicken, the scissors for the kids, pen, paper, crayons and more. It’s the equivalent of your utility bag. These little purses match the shoes we just got you. The shoes and these purses are for going out on dates, to the clubs and so on. No one expects you to carry that huge bag-of-all-haulage, so you have smaller bags for your wallet, some money, credit cards and a little makeup. That’s what you take to a restaurant or a bar. Those Mom-bags you keep for daily use.”

When she explained it that way, I could see the sense of it. Who would want to take a Battleship up a delta when a Zodiac would do that much better. I nodded my understanding and let her direct me.

***
I had been trying to keep a running tally of our expenses, but I failed. I knew that we had spent somewhere near $1200 by the end of the day. Several sets of makeup, five dresses, six skirts and four blouses. One suit. Five pairs of shoes and three handbags. Scarfs, earrings, bracelets, hose, a penior and nightgown, panties, girdles, a corset, bras and everything a new woman needed. I felt as though I were picking out my trousseau by the end of it all.

I gradually relaxed over the day. Things didn’t blow up like I thought they would. I kept noticing others looking at me and it made me nervous, but Mistress kept blowing it off. She told me not to pay attention that mostly it was jealousy on the women’s parts and wondering about their chances on the men’s.

I had to admit, once I had good makeup on and I saw myself in a mirror, I did wonder if she would be willing to sleep with me. Then I blushed as I realized what I just thought.

Not everything went well, however.

We were on our way out of the mall when I spotted a darling little halter dress in a boutique window. I stopped to admire it and before I had thought about it much, Mistress had dragged me inside to try it on.

The ambiance was not the best, dark interior, pounding rock music, skimpy clothes and ultra chic cutting edge fashion. Racks and racks of body jewelry were on display on the counter. When did barbells come into fashion?

Mistress went over to the wall and started looking through the displays of clothes. She picked out two different dresses in my size and a pair of knee high boots in my size off the discount area. She shooed me into the dressing area to try the clothes on and waited.

I came out a few minutes later and showed her the outfit. I have to say I was smokin’ hot. A different hair style, one of the small handbags I had, some of the accessories and I would be a babe.

Mistress helped me out with the fitting and the various accoutrements. Once the boots were on, I was slightly taller than her and if it weren’t for my face, I’d look really good. But that would come another time.

Mistress complimented me and had me change back into my “gypsy garb” as she called it and took the clothes and boots up to the counter.

I joined her. It must have been a slow day because the store was empty. Just the five people who worked there, Mistress and I. The manager started ringing up the clothes and she was smiling. I was mortified to see $238.51 come up as the total.

The next few seconds are burned into my memory.

The music broke for a change in songs. I was relieved because I started getting a headache from the heavy bass and drum beats.

Everyone clearly heard in the silence of the store the word “Faggot.”

It resounded around the store. Mistress’ head whipped around and could not tell who had said it. The acoustics were such that those standing at the counter heard the speech from anywhere in the store. Her head whipped around while she tried to find the source of the epithet.

I froze. I couldn’t move. My worst fears were realized and the blood had turned into icewater in my body. I flushed and then I turned cold. My breath came in short gasps. I couldn’t think.

I felt a hand grab mine and I was nearly dragged out of the store. I was still stunned and I don’t remember hearing anything, just a roaring in my ears.

When I next found the capacity to look around me, we were in Mistress’ car and nearly to her home. I still couldn’t think.

***

When I heard whomever said that word in the store, I knew what the reaction in Sissy’s head would be. I knew that she would be devastated and that we had to get out of there fast.

I looked around knowing that I wouldn’t find the person, and noticing that it was only the staff here, that the customers had slowly drifted out while we had been shopping.

The manager look pole-axed. As well she should, there was no excuse for that kind of derogatory term to be used, especially with a customer.

I had started to get out my regular Visa card to pay for everything, but under cover of the looking around, I got out my Gold MasterCard instead. I looked back at the Manager and slowly put the MasterCard back into my wallet.

“Sissy, come on. We’re leaving. There is no excuse for this and I won’t shop someplace where you aren’t welcome.” I made sure the Manager saw the gold before I slid it back into the little slot in my wallet, then snapping the wallet closed.

The Manager tried to stop us. She started babbling. She knew that she had just lost a HUGE sale, one that could pay for the expenses of the shop for all of today. This was going to be a major blow to her bottom line, and someone was getting in massive trouble for this.

The other sales associates tried to stop me as I neared the door, my blood boiling and Sissy’s wrist firmly in my had. I had a lot of experience of holding wrists and keeping hold of them when the captured didn’t want to be in that position, but Sissy didn’t resist at all. She was too stunned.

I shot a withering glare at the associate who was trying to impede my egress; she wisely moved out of my way.

The Manager finally got her head together and charged after me. But I had a good head start and she had to run on her very fashionable stiletto heels until she caught me three stores down.

I let her babble an apology for a bit and I finally cut her off. “It’s obvious that your staff doesn’t see things your way, and in my experience the staff reflects the management. If this is how your store deals with customers who don’t fit the norm, then you don’t need my business. It’s not like I couldn’t get everything that was on that counter at other locations, in some cases for less money than you were charging. Your store was convenient, it happened to be there, nothing more.”

I had carefully planned those words as I stormed out. I knew that they would hurt, and I meant for them to. I had no tolerance for people like that and I intended to make that fact clear.

One of the other Associates came charging up behind, a bag in her hands. The manager all but snatched it from her and practically shoved it into my free hand, babbling about how sorry she was and that the situation would be taken care of and would I please reconsider coming back and to please take this as her way of profoundly apologizing for that gaffe….

I turned and stalked off without saying another word to her. The bag was firmly in my hand and it would remain there until we were out of the mall. Let her write off nearly $250 in merchandise, one of those little bitches was losing their job, and if none of them confessed, they would all probably be fired. Perhaps at some future date they would remember this incident and remember to treat a customer with more courtesy, no matter what their personal feelings were.

By the time we made the second set of traffic lights as we were leaving the mall, I had calmed down. I was shaking in reaction and probably from the adrenaline in my system. But right now I had to deal with Sissy and how she was going to react to this.

Damn, a perfectly lovely day ruined by one idiot. I had to think of what to do now.

A Whole New Sissy -- Pt 7

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Transformations

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Fresh Start
  • Real World
  • Voluntary

TG Elements: 

  • Breasts / Breast Implants
  • Corsets
  • Hair Salon / Long Hair / Wigs / Rollers
  • Maids / French Maids / Servants

Other Keywords: 

  • Spa Day

Permission: 

  • Posted by author(s)

A time to rest and then a reward for a job well done allows Sissy to start healing and really become the woman that she might be. Can it continue?

A whole new Sissy -- Pt 7

Maid Joy

The sages of the past who said “time heals all wounds” may have been spouting a platitude, but it turns out that they were right, damn them.

The more time that passed the less the “faggot” comment hurt. I could even laugh about it.

Mistress was great about it. She helped me deal with the problems that arose in my own head that stemmed from the comment. I wasn’t as upset to be thought of as a homosexual, as I was about being spotted as a guy in drag. The fears that flowed from that issue were numerous.

I was very afraid. To start, I was terrified that if someone I knew from the base spotted me that I would be thrown out of the Army. I was also terrified that all that I had worked for would be seen as a sham. My culture, military culture despises weakness. What I wanted, what I needed would be seen as beyond weak, it would in my comrades eyes as a betrayal of not only myself and the Army but of them. I didn’t think I could face their looks of condemnation and rejection.

I think a lot of the dilemma was because I had a lot of time and effort invested in who I showed myself to be. I know it wasn’t who I truly was, but there was a lot of pain and effort and achievement in being the macho soldier that I portrayed. I didn’t want that all invalidated by another aspect of my character. I believed it was an aspect that I could live without if I had to.

Granted, I wouldn’t be happy to lose that part of me, but I could deal with it. After all, if you have never had Ice Cream, how can you miss it?

***

It had been two months since that first outing and shopping trip. Mistress had been helping me, teaching me how to do everything from walk correctly to applying makeup. I had taken to trimming my leg hair to keep it shorter, not shaving it all. Doing PT with no leg hair would have been an “interesting” clue.

I had learned to move with more grace than before. It seemed to be more of a martial art skill, moving with a graceful flow, than many people realized. I mean, most times when fighting it was about power and crushing the other, dominating them with sheer force. In Kung Fu, however, it was about flowing and redirecting energy into another direction, rather than crushing.

Walking in heels, moving with grace, keeping my legs together, all that seemed more suited to Kung Fu than to moving like I normally did. I flowed from one point to another, then I alighted on a chair. I stayed stationary for a time, then I rose or ascended and moved to where I had to go.

I found that most furniture, as it is currently made, didn’t lend itself to this style of movement. Oh, I loved the overstuffed chairs when I was in “guy” mode, I took my seat and I relaxed back. But when I was in “Sissy” mode, and I perched on the same chair, I felt like it was not even close to being comfortable. The mechanics were all wrong for me to sit. It was too short, or too deep, too well padded, or something. I found myself perching on stools or on hard chairs, standing and waiting rather than trying to fight the design of the furniture.

I had to learn all kinds of things. I loved every minute of it.

Slowly I was able to pay Mistress back for her incredible generosity. Her offer was exactly what I needed and wanted. She gave me a place where I could be myself, without judgment, that in and of itself was a relief.

Two months of spending my weekends with her. Understand when I say “weekends” I mean the time off I had scheduled. It wasn’t always Saturday and Sunday, sometimes it was Tuesday and Wednesday, it all depended on the training schedule and the duty rosters. I was able to manipulate things slightly so that I had time I wanted, and I was always able to have my time with her.

There were some complications, as a Non Commissioned Officer I was expected to do a certain amount of socialization. About 80% of that socialization I was able to avoid and blow off, but the other 20% was mandatory. That cut into my “me” time some what.

We were both looking forward to the three weeks I had scheduled as vacation. I didn’t have much to spend my leave on so it just accrued. But now I wanted a vacation and I decided to take a while off.

Mistress promised me that I would be spending every possible second of that time as Sissy. I couldn’t wait.

***

At last the time had come. I handed my duties over to another sergeant, made sure I hadn’t forgotten anything and I packed my bag to leave. I had my paperwork and my identification in my pocket. I was ready.

I got out to my car and loaded the trunk up with my duffel bag. There were other things that I had gotten into the car at other times, and I didn’t want them seen right now. A few of my mates were present to say goodbye to me, and with some good natured back slapping and hand shaking, I got into my car and left the base.

It took me about a half an hour to get into the city and then finally to Mistress’ work area. I knew that she would be busy with another client, so I quietly came into the house and left my bag in a closet I was told was mine. I brought in the rest of the stuff, my prom dress and the overnight bag of Sissy’s clothes that didn’t leave my car. I double checked everything and started my transformation.

Without causing a problem or making a ruckus, I went into the bathroom and showered. I had taken to trimming the hair on my legs with the clippers I had to keep my head buzz cut, and now it was only about ten minutes to remove all the leg hair. This was the first time I had done this since physical training and body modesty was not something that was a high priority in the barracks, even though I had my own room. I couldn’t believe how different my legs felt without the insulation of hair and the extra tactile input.

I finished my shower, shaved my face completely and dried off. Mistress insisted that I use some lotion on my skin once I got done and so I lubed up everywhere. It had a nice flowery scent and I reveled in it.

I didn’t have much hair to deal with, so I just wrapped a towel around my torso, covering my breasts so I started to get into the mindset, and I went back to “my” room to change. Panties first, after tucking away that annoying bulge and putting on the dancer’s belt, the padded girdle came up and gave my hips and ass some shape. Bra and breast forms came next. Mistress had found some glue to mount the breast forms on my chest, and I proceeded to put them on, gasping a little as the glue hit my skin. A few seconds of curing time and the breasts were attached as though I had grown them myself.

I was already feeling different. My motions took on a whole different manner and I flowed into resting on the vanity bench at the make up table. I tweezed my eyebrows for a bit, plucked any stray hairs on my face and started the process of putting on the layers of makeup that a woman needs.

Eyebrows cleaned up the soft brush and dark powder was applied to define the newly feminized brow. Next up finish off the face with foundation, blush eyeliner and mascara — done. I had learned to disguise the line where the breast forms met my chest with more makeup as well. Finally I had the majority of my “face” done. I had decided on a pink scheme for the day, not a heavy look, just one that lightened my features up and opened my eyes up. I set it up with a translucent power and made sure that everything was looking nice.

I pulled out one of the maid uniforms that Mistress had me in before, except this time it actually fit me. Short skirts on the previous uniform came down to nearly my knees now, the bodice actually fit and I looked nice. I pulled the stockings on and rolled them up my newly shaven legs.

Mistress was right, again, the lack of hair on my legs did open up a whole new world of sensations. Oh, this felt yummy!

I attached the stockings to the bottom of my girdle with the tabs that were sewn into it for just that purpose. Next I pulled on a corset and laced it up as best as I could. I hadn’t practiced doing this much, but the principle was not hard; hook up the busk in front, loop the tapes over the doorknob, and then walk as far as you could from the door. Tie off the tapes and voile, instant girl form.

Uniform on, zipped up the back, three inch pumps on the feet and the ankle straps closed, apron tied off and looking neat, finally the wig that Mistress loaned me. I made sure it was on and looking nice, and examined the final product in the full length mirror on the wall.

I had once heard a comedian say that the measure of Vanity was if you would shag yourself. I had to admit that I would if I didn’t know it was me.

With that happy thought on my mind, I left to go and do my self-appointed chores.

***

It was inevitable that I ran into Mistress and her client while cleaning. Making up the beds and cleaning the private rooms didn’t take much time, so I moved on to the public rooms.

“And here’s my pride and joy; Sissy! How very good to see you! Could you take a few minutes and make sure that this idiotic slut learns how to properly dust? I’ve been trying, and she just isn’t getting it.”

I walked slowly and sensually into the parlor and saw what Mistress meant. She had her current client in the same slut uniform I had on at one point, same bad makeup job, and this poor girl was trying desperately to maintain her dignity while cleaning, which was impossible of course.

I curtsied, “Of course Mistress. It would be my pleasure.” I could see the flush on this new girl’s face since she wasn’t able to do the job properly. I ordered her to watch me.

I took the duster out of her hand and showed her how to dust. It wasn’t the dusting that was the important part, but the bending and stooping, intentionally showing off the ass, chest, legs or whatever was convenient to tease and embarrass the girl in question.

Mistress was effusive with her praise for my skills and very abusive to her client. Having been through it and understanding the rhyme behind the reason, I could admire her deft touch. Just enough praise to keep her client encouraged along with the humiliation they paid for.

I kept myself out of the way mostly. I let Mistress do the interacting, and I was busy quietly doing the real chores while this client (whose name I didn’t even know) ran around and incompetently cleaned and re-cleaned things that she didn’t get the first time.

***

Three hours later, her client was sent on home. I finished cleaning up the “toys” and put them in their proper places. I smiled to myself because even though I was still squicked out by some of them, most of these devices didn’t bother me much any more. They were tools of a trade, no different from a knife in my hands, or a hammer in a carpenter’s hands.

Once Mistress got cleaned up, she came and gave me the instructions for her next client. This one was going to be a BDSM special, so I was instructed to pull out the floggers and other impact toys. She made sure to put a collar on me and cuffs on my wrists. I had to look like I was Mistress’ personal property since I would be handing things to her as she needed them.

“Understand Sissy, you are not going to be touching him at all. I’ll be doing all that. All you will need to give me is the items I require. So have the binder clips, the clothes pins, and those kinds of things ready for me. Alcohol, pads, towels and latex gloves are going to be needed. This is going to mean a lot of pain so make sure the gags are out and clean. I have to get into my ‘bitch domme’ outfit. Once everything is out, come and help me get dressed.”

She stopped for a minute on her way out, “You did very well this morning with her. You have a talent for this kind of work. Maybe a good career for you once you are out of the Army?”

It wasn’t until much later that night that I had time to be with Mistress on my own. Or really think about what she had said… out of the Army, did I really want that?

***

That pretty much set the tone for that first week. Mistress had clients almost every day and I helped her as I could. Most often I stayed out of the way, took care of her home while she worked and for that, I had free run.

I shopped for food, out as a Lady. I felt more comfortable being out and the fear of being ‘read’ slacked off greatly. Being this far from base made it vanishingly slim that anyone from my other world would see me, and if they did, it was highly unlikely that I would be recognized.

I also didn’t think that they would look too closely at a lady shopping for groceries.

I got home with the four or five bags of groceries for the next couple days, and Mistress caught me in the kitchen.

“Sissy, we have tomorrow off. I cleared the schedule and you have helped me so much that I’m treating you to a Spa Day.”

“Spa day? What’s that?”

Mistress grinned. “It’s probably the most decadent day a woman can have. We go to the spa and let other people pamper us.”

“What kind of pampering?”

“Well, first there is the massages and the seaweed wraps, then the hair styling and the makeup, then the mani/pedis, possibly waxing as well. It depends on what is needed. But believe me, you will love it. Should take us most of the day.”

“Um, I have to ask, is this going to mess things up for me when I go back to work? I don’t want there to be anything lasting that might spill the beans with the rest of the unit.”

“Trust me, while there will be a few things that could be long term, most of it will work out in the next two weeks. I want to give you something that will make you feel beautiful and heavenly.”

“Won’t the fact that I don’t have hair of my own make it a bit awkward?”

“No, a lot of women wear wigs, and if it comes to it we can tell them that you had a double mastectomy and chemotherapy, which would account for the falsies and the lack of hair. No one will think anything of it.”

I took some time to think that over. “Okay, it sounds like a lot of fun.”

***

The next day I got up with some anticipation. This was an unusual as most often I had a very set routine. This is going to be a memorable day.

I got dressed, light makeup and not much in the way of coverup. Mistress got me and we drove to the spa.

I have to admit that I was more than a little nervous when I was shown into the changing room where I was supposed to disrobe and put on a spa robe. I was worried that I’d be exposed my uncomfortable bulge recognized for what it really was. I tried to take a deep breath, relax and enjoy the experience.

I saw Mistress and we started the process. The first thing was a hot rock massage. I laid down on a table and a lovely lady took very smooth warmed stones and used them to rub my back and legs. It forced me to relax and it felt so good.

I had read and heard about this, but it was nothing like living through it. It felt like heaven.

The seaweed wrap came next, and I kept my panties on for the whole time. Before the wrap, I had to use the solvent and remove my breasts. I honestly thought that this was going to mean the end of the time I had as Sissy. But with the removal of the wig and breasts, no one thought anything about it.

The lady who did the body wrap said “I’m glad to see you healing. We’ll take good care of you and make you feel beautiful again.” That was all that was ever said.

I luxuriated. I relaxed and simply let them do things to me. I know I napped a couple times in sheer bliss. I didn’t think I could relax this totally, but I did. I was oiled, lotioned, rubbed and my pores were cleaned. I didn’t have to raise a hand to do anything.

Going to the gym and even sitting in the sauna or the steam room never felt this good.

Finally, the masque was taken off, the cucumbers removed from my eyes, and I was washed down with a sponge bath. I was told that I would need to get dressed again and it was time for the makeover.

Apparently I wouldn’t need to be waxed since most of the hair on my body was of the baby fine variety. The hair on my legs was short enough that the wax wouldn’t take and just shaving would handle it.

Once I was dressed I was led to the makeup/hairstyling chair I would be in. Three people descended on me. Alice would be taking care of my face and makeup. Pika would be doing my hands and Charlie my toes.

Pretty soon I realized that my best bet was to simply sit still and let them do whatever they wanted to do. The facial was checked over, and my face was rubbed again. Part of this was apparently a face massage and various specialty lotions to tighten the skin on my face. I was complimented on the condition of my face, there weren’t any wrinkles or crow’s feet. The bags under my eyes were tightened up somehow and the rest of my face was cared for.

While that was happening, Pika was rubbing my hands. She was a bit quiet about the damage done to my hands, the rough skin, the broken nails and the torn up cuticles. She spent a lot of time on the nails, trimming, cleaning and generally repairing years of abuse.

One of the things I thought was most touching was that they had a turban for me. My wig was set aside and another lady was busy styling it so that it looked good.

I saw Mistress across the way she was also getting a similar treatment. It made me feel good and I relaxed.

These ladies treated me just as if I were an honored lady guest. I didn’t speak much, but they kept up a chatter that I found very calming and soothing. They told me what they were doing and why. Toenails trimmed, nails buffed and more.

I was asked if I wanted my ears pierced, but I stopped them before they did so. I explained that I had a hard time healing after the chemo, and they understood completely and quickly. The topic was dropped and not mentioned again.

After hours of sitting in the chair and letting these ladies dote on me, finally they were done. The turban was taken off and my wig restored.

I was shown a long mirror and the change was stunning. I had finger nails now, slight ones that were just past the tips of my fingers. Apparently part of the treatment was acrylic nail tips, glued on to give me solid nails instead of the brittle things I had before.

My makeup was done by a master artist. It looked so much better than anything I could have done on my own. My eyebrows were plucked and thinned as they needed to be, arched in a delicate feminine curve. My eye lashes were curled and thick with mascara, the smoky shades on my lids making my eyes larger and deeper.

The nail polish on my fingers matched the lipstick, and I noticed for the first time that I had toenail polish as well. My feet and hands felt smooth and soft. I couldn’t believe how much of a difference that a little lotion and some pampering had on me.

I was floating on cloud nine. I gave all the girls who worked on me hugs and thanked them as best as I could. I don’t know if they would understand the depth of my gratitude, but I felt myself tearing up. There weren’t words enough to tell them how much it meant so I hoped that the generous tip I knew Mistress would add would be enough. A quick tissue later to keep from messing up my makeup and Mistress and I were on our way.

***

“So how did you like it?”

Sissy was a bit dreamy in her response. “It was heavenly. It felt so good and I loved it so much. Thank you.”

I smiled. “You are very welcome. I’m thinking that we can get our party clothes on tonight and go out dancing.”

Sissy got a bit nervous. “Do you think I could pass in a club for a girl?”

I thought that she looked better than many of the girls that would be there. “I think that if you went to the right place, with the right people you will pass for a girl without a problem. And I think you need the experience that comes with being a pretty girl in public. You are gaining a lot of confidence, and your growth is amazing and I love it. But you still need to be in close contact with others and have them say the same thing.”

Sissy did look a bit more nervous. I knew that nervousness well, as I had seen it many times. I knew the club would do more good than harm.

“Sissy, don’t worry about it. I’ll be right there-” I was interrupted by a persistent beeping from Sissy’s purse.

She blanched and dug her pager out. She glanced at the number displayed and dug her cell phone out.

She quickly dialed a number and started speaking. “This is Sergeant Taylor. I was paged.-- Yes. I understand. Thank you.”

She closed the phone and in a very flat voice said, “We need to get to your home as soon as possible. My leave has been canceled. My unit has just been activated to be deployed.”

Sissy and the Army -- Pt 8

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Identity Crisis

Permission: 

  • Posted by author(s)

Sissy's leave is canceled and she has to go into combat. Will her secret be discovered?

Sissy and the Army -- Pt 8

Maid Joy

It was every nightmare I had come true. In the middle of everything I loved and enjoyed, it all came crashing down to call me back out into combat.

We got back to Mistress' house and I raced inside. I crossed the threshold to the back and my wig was off. I had enough respect for it to put it on the dummy head where it should be. I started stripping out of my clothes quickly. Off came the blouse, then the skirt, the shoes, the girdle, the bra and then the breast forms.

I stepped up to the mirror and grabbed a huge handful of the cold cream and started smearing it all over my face, making sure to get from my hairline to my upper chest. I rubbed and scrubbed to get all the beautiful makeup off.

I was trying very hard not to cry as I left Sissy in a pile on the bed. Jewelry came off and while I didn't scatter it, I wasn't careful to put it back exactly where I got it from.

I knew that deployment meant a mission of some sort. I'd have my rifle in my hands, a pack on my back, I'd be cold and scared in the bush beyond no where, and I would have my life on the line.

I sat down on the vanity and started stripping the polish off my nails. Taking off the polish on my toes was easy. I just poured some remover in a bowl and shoved my toes into it. As the polish dissolved I choked back a sob.

When I started taking the polish off my hands, I ran into a huge problem. The nails were super glued on and I couldn't get them off. The polish was easy, but I nearly ripped my own nail off trying to remove the acrylic extensions on the tips. I started panicking, and then calmed down and decided to just cut them off.

I grabbed the nail clippers and started slicing. The first cut didn't do anything except nearly break my fingers. These little tips were STRONG. I couldn't get the clippers to cut them at all.

Mistress dropped toenail clippers on the vanity in front of me. I smiled with tears in my eyes and grabbed them instead. It hurt, but I was able to cut the nails off. The clippers had a tendency to bend the nail tips instead of just cutting them, and it really did hurt when my soft nails were bent too.

I made sure that the polish was gone, that the makeup was gone and I started getting into my uniform. Mistress quietly cleaned up the clothes and accessories that I had on only minutes ago and putting them away.

With speed that would have surprised people that had never been subject to middle of the night emergency drills, I was fully clothed and ready to go. I reached down, grabbed my duffel bag, which had never been unpacked, and started for the door. Mistress was in front of me suddenly.

I looked at her, and she at me. "I'm sorry. I'm so sorry. I didn't know that this would happen." Before I could finish she stopped me and kissed me on the cheek. "Be safe," was all she said. "I'd hate to lose my girlfriend."

She gently and firmly pushed me out the door.

***

I had to shed Sissy's self and get back into the mind of SSgt Taylor. I had to leave behind my feminine side and get back to being a highly trained killer. G_d witness how much I hated being that killer now that I found Sissy.

I reported to the briefing with the rest of the NCOs and Officers. We had to know the tactical goals to do our job correctly. If we didn't know what was going on, people would die.

I had my equipment and my weapons. The situation was one that we had faced over and over again, a very short goal, but of enormous value. Burst into a place, get people out, and extract ourselves.

(I can't tell you more since this journal is public, and this was a classified operation. I wouldn't use the old "I'd have to kill you" joke, it's overdone. I will share what I can with you.)

The First Sergeant was kind enough to pull me aside before we deployed. "Sorry I had to cancel your leave Taylor, but I'm sure you understand." He was looking at me oddly and his nostrils were flared.

"It's fine First Sergeant, I wasn't doing much of anything anyhow. Just laying around and enjoying myself." I didn't think.

He nodded. "Well, I see you got some severe pampering, if that manicure is any indication." Shit, shit, shit, shit…. He had noticed something.

I nodded. "Just a little self love, a real break from this." I had to get away. "I need to get back to my men Top, do you need me for anything else?"

"No, go ahead." He was still looking at me oddly.

Soon enough we were in the air, going to the euphemistic "undisclosed location". I had taken some ribbing from my men about the soft hands and face and I hoped to G_d that they didn't notice the eyebrows.

***

The only thing of real interest in the next few days was the actual insertion. A HALO drop from 30,000 feet to pop my chute about 100 feet off the ground at night is harrowing, but it was the only way into the area since it had three different groups fighting for it.

My squad and I landed within feet of our target and shed our chutes. First objective to meet was actually penetrating the perimeter. Then would come the really fun part, getting to our actually objective, the prisoners.

Boring military stuff follows so I'll skip most of it. We finally got into the prison and got the people we were after and were getting out. Each squad member was responsible for one prisoner. I had given mine my handgun so that he could cover my back and defend himself if he had to.

He knew the drill, he was a soldier. He was a good man.

On the way out we got pinned down. We were taking fire and he had run out of bullets. I still had ammo, but not a lot. The rest of the squad had gotten out and were trying to come back for me not easy since I had to keep moving to avoid getting either of us killed. A grenade landed nearby and the way opened up. I grabbed the guy I was with and we bolted for shelter.

In the cover of another doorway, I ran out of bullets. Since he had already emptied my pistol we were both out. I put those weapons away and started plotting our way out when the door opened and my guy was grabbed. A pistol was pressed to his head and the Arab started screaming something at me.

My hands went up, just high enough to smash his nose into his brain, killing him. I grabbed the enemy's pistol and we were running again.

Finally we managed to rejoin the squad and I half carried, half dragged my guy out of there. It was noisy, it was deadly, but we made it. We didn't leave anyone behind, we didn't leave any of our equipment and we accomplished the objective. None of my men were killed, only one was injured. It was a good night.

***

Two days, the debriefing over, the shakes started, a delayed reaction to how close I had come to dying. It was impossibly hard having to relive those moments of gut wrenching fear over and over, and be unable to react emotionally. So I slapped a lid on it and ignored it, like every soldier does at one point or another.

It took me several days to get past the emotions and the shakes. I didn't even think about becoming Sissy again. I knew I couldn't handle it.

That military of me was so at odds with Sissy, I didn't think I could ever reconcile them. How could I go from a fragile little creature to one that could literally kill with my bare hands? How could I come to being at peace with those extremes? Was it even possible?

I knew that I was starting to use Sissy as a haven for my psyche, a place where I didn't have to think about what I did for a living. I also felt that I was betraying my country by running away from those duties to be someone I wasn't.

Still, I was Sissy and she was me, so was it really running away?

I thought I was confused when I started really exploring the Sissy in me, now I was starting to feel lost, with out a compass or a map to guide me to the path I needed.

***

The First Sergeant made sure that all his men were taken care of after the mission. Taylor was a concern and he made a call.

"Yes, CID? Can I speak to First Sergeant Williams? Thank you. Frank! How's it going? Really? That's great. No, not a social call. I have to ask you a favor. I'm concerned about one of my own. I'm worried that he might be being blackmailed. Yeah. Staff Sergeant Gregory Taylor, ID number 094-33-1288. Yea, assigned to First Platoon. I'm not sure, but when he was recalled from his leave, he came back different. His eyebrows were plucked, his hand were all soft and shaped, he had fake nails on and he smelled like a girl. I'm worried that he's gay or something. Do you think you could get someone to quietly check up on him and where he goes on his leaves and days off? Yeah. Yeah, as soon as possible. No, I don't think there's anything criminal involved, but remember we are talking about a combat operative with a high security clearance. He may not be up to the level of the CIA, but he's good enough. Yeah, just to me. Thanks, buddy. I owe you one. Okay, I'll spot you three holes next time we are in Augusta. Talk to you later."

The phone was placed back on the cradle and the First Sergeant started drumming his fingers on his blotter.

Sissy Captured -- Pt 9

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing
  • Transformations

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Femdom / Humiliation
  • Identity Crisis
  • Real World

TG Elements: 

  • Appliances Attached
  • Chastity Belts
  • Corsets
  • Sissies

Other Keywords: 

  • BDSM

Permission: 

  • Posted by author(s)


Sissy Captured -- Pt 9

Maid Joy

I was in my barracks and getting dressed for formation. For the five hundredth time I wished I dared wear my panties instead of these bikini briefs. The tighty-whiteys that were issued (in reality grungy-greenies for the OD green color) didn’t feel right or make me happy to have them on, mainly because of how badly they hurt and fit.

When I say hurt I mean that they were rough as hell. I have no idea why women’s panties were soft and heavenly and males’ underwear was so scratchy and rough, but they were. It couldn’t be the washing, I always use fabric softener, yet the tactile difference was notable.

Lycra and spandex panties were heaven to me, but I also knew they weren’t the most comfortable item for long term wear. They retained heat and made things very humid down there. I couldn’t wear the same set of panties without washing them. I could *sometimes* get away with that with male underwear, if I wasn’t doing too much sweating.

Men sweat, ladies glow. But I couldn’t seem to get past the sweat part. Maybe it was genetics, like everything else. When you are as physically active as I am, there is really no hope for it.

But cotton panties, they were heaven, slightly stretchy, soft as down, gentle to the skin that was fantastic. There were occasional problems, (I tended to fall out of them since that crotch area was a bit narrow), but they were easily the most comfortable things I had on ever.

The odd part was that the construction of the two items weren’t that different. They had the same basic materials, a slightly different cut, and that flap to let men go to the bathroom without pulling their pants down. You wouldn’t think it would make that much difference, but it always did.

***

The days had passed quickly. I was counting down the days until I was out of the Service. It was hard to believe that I, a career Army man if ever there was one, couldn’t wait to be Short Time. I didn’t know what had come over me.

Mistress was great to me. She had been treating me more like a colleague and a friend than a patron. I didn’t have to pay her anymore to come over and dress up, and occasionally she played with me too. Still no sex, damn-it, but it was better than nothing.

There were days that I dreamed of having the whole plumbing system that I wanted and having her do things to me. I wanted my first orgasm as a woman to be at her hands. I knew that it was possible that eventually I would want to be taken like a woman would be by a man, that was probably inevitable, but I was determined not to think about that until it actually happened.

I mean, I can intellectually understand being gay. That was no problem, as long as it was other people. I didn’t really feel that way myself. I looked around at other men, saw nice people who took care of themselves. I was surrounded by really buff bodies and they did nothing to arouse me. As a female that should have make me a lesbian, but still. I did my best not to think about it since the ideas just left me more miserable and confused than I was before. Everything was yes but. I was use to the certainties of military life with all of its regulations; your thinking was done for you. I was not comfortable or happy in the floating limbo I found myself in now.

I had fantasized occasionally a long time ago what it would be like to have a dick in my mouth. I think most boys have that fantasy once in a while. I didn’t actually have any opportunity to do anything and I don’t know if I could have if given the chance. But now, who knew?

Don’t think about it, do not think about it, change the topic my brain shrieked. That was a problem for another day. Don’t borrow trouble and don’t fret.

I tried to take my own advice and ignore the thoughts running through my head. One interesting consequence of my choices was I noticed women more.

Not in a sexual way, although they did look nice and I did think about a relationship with some of them, but more in a “would that dress/outfit look good on me?” way. I was noticing the cut of outfits more, fitted blouses and belled or boot cut slacks etcetera. Some outfits worked and looked really nice on the ladies I looked at, but others just didn’t at all. It made me wonder where the Fashion Police were when you needed them.

In my room, I noticed that I was watching things like “What Not To Wear” and “Platinum Weddings” and so on, just to see the outfits. I tried to develop a personal style of dress that would compliment my skin and my body shape.

Good thing I didn’t entertain many people in my bedroom.

***

Several weeks later on a “weekend” visit, Mistress asked: “Sissy, Halloween is coming up, do you have any plans?”

I had to think for a minute. I knew I would be pulling duty rotations at the base, but I didn’t know if it was that particular night or not.

“Looking at the calendar in my head, I am on duty the next week, but not the thirty first. Why? What’s up?”

“I thought that one night that you could dress up as outrageously as you want to and no one would say anything about it. If you are like the other TS girls I know, there’s part of you who wants the fantasy. You know cheerleader, anime character, nurse, cat-girl or something similar. This would be a perfect time to let you express it.”

I thought while I was washing the dishes. I understood the appeal and to be truthful I had those same impulses too, but not exactly the way she thought.

“Well, I wouldn’t want to try a naughty nurse, a midriff top and my abs are a little too much to be truly feminine. The cat-girl costumes I’ve seen don’t leave much to the imagination and I really don’t think I would look nice in them. It’s funny; I really do want to look nice and passable, not like a slut or like a freak. While I loved Michelle Pfeiffer’s Catwoman costume from Batman, that’s some really skintight latex. I know I wouldn’t look right in it.

“I never wanted to be a cheerleader, mainly because I’m not that extroverted and peppy. I do like the uniforms as much as the next person, but some of them are just too…. I don’t know how to describe it. I know I’m not a dancer.”

Mistress was quiet while I had verbal diarrhea and thought out loud. “If I was honest, the outfit I would like to dress up in is a female officer’s Class A’s. I’ve always thought they were some of the most attractive uniforms in the Army.”

Mistress looked sideways at me. I couldn’t quite read the expression on her face. “That shouldn’t be hard to do. A trip to the Uniform store to get a full outfit in your measurements and some substitution of heels for those ugly flats and a few custom tweaks to the fit and cut, and I think you would look very nice.”

She fell silent and I could see the wheels turning in her head.

“Okay! Let’s get ready for another client. I have a real masochist coming in, and his fantasy is to pretend that you are his wife and I’m torturing both of you. Think you can handle that?”

I was kind of stunned. “What is going to happen?”

“When he comes in and I lock him into that wonderful heavy wooden chair in the dungeon. That way he has a good view of the room. He’s gagged and blindfolded for the first part. Once he’s locked and secured I remove his blindfold and he sees you, tied and helpless. I work on you for a while, floggers, whips and so on, all the while he can hear you shriek with pain, even though it won’t be painful for you, and he gets to be helpless while you are ‘used’ by me.”

I got a bit nervous. “When you say ‘used’ what do you mean?”

Her lips thinned in slight irritation and embarrassment. “It means that I’ll be using a dildo on you — anally.”

I was quiet for a few moments while I thought. “I trust you. After everything you have done for me and with me, you are always my Mistress and a dear friend in many ways. You have given me myself and if this is what it takes to pay you back, I’ll trust your skill to not hurt me.”

She sighed deeply. “Thank you for your trust. I’ll try not to violate it.”

***

We retired to the “dress up” chamber and I started getting ready. I stripped down to skin and my boobs, which were glued on to my chest. Mistress had a special piece of equipment for me first.

She brought out a mass of metal. “Sissy, this is a chastity belt. I’ve got one that is somewhat adjustable but we will have to play with it a while to make sure it’s comfortable on you and that it’s secure.”

The first thing that came out was a tube. She slipped a knee high stocking over my penis and fed the end through the tube. She then pulled the tube up until it was completely around my penis and then removed the nylon. With that caress I got instantly aroused, only to discover that just the tube by itself was enough to stop anything further.

She slipped the waist band around my hips and then fiddled with the sizing a couple times until it was snug around me. “No, that doesn’t look right. Let’s get a corset on you first to hide your abs.”

She left me in the tube, but removed the waistband. She grabbed a corset that I had worn, one that was supposed to be seen. It had lots of trim and beautiful decorations. Any woman would look beautiful in it, and I’m certain that most women would feel beautiful when they had it on.

She pulled the ribbon lacing firmly, leaving my breasts hanging since there were no cups for them. As she pulled it tight, it felt better and better, like a solid hug that covered most of my body. It was hard to breathe after a bit, but not terribly so. I started breathing from the top of my chest and panting a bit more and it was fine. I certainly wouldn’t be doing any long hikes or five mile runs in this.

Once she tied the ribbon into a lovely bow, she put the waistband back in place. It fit much better and didn’t pinch anymore. She pulled the chains across my ass, and the front plate came up between my legs. She hooked the front plate in place and slid the penis tube in place, making sure that I didn’t fall out. She adjusted it a couple times, then mated the front shield with the waist band and checked the fit. She then opened up the front shield up again, and changed the length of the chains so they were snug against my ass, then tried it again. Once she finished fiddling she pulled out a circular lock and put it over the post at the top of the waist band. There was a loud “SNAP” and for some reason, I tried to get hard again.

I blushed crimson, and I was sure that Mistress could see it. She grinned and said “There’s nothing to be ashamed of. Lots of “girls” and male submissives have that reaction. Don’t worry Sissy; you are acting like any red blooded girl submissive would.”

She picked up another piece, another shield that covered the front plate of the belt where the tube was attached. She hooked it in place, and lifted it up, and with another “SNAP” it closed and locked.

Mistress stepped back and looked at me. “Wow that looks marvelous on you. We’ll have to do this again at some point. You look wonderful.”

I had to admit that I felt really vulnerable. My asshole was still open and while my penis was locked away. I could be taken but only as a female could be. I felt safe and vulnerable and pretty and sluttish all at the same time. It was a wild ride of emotions.

“Okay, now for the rest.” Mistress sat me down and started doing my makeup, helping me with my hair and so on. She put me in a leather bikini top that matched the corset and helped me into the four inch heels.

“He’s going to be here in about thirty minutes. You need to help me get ready now and then I’ll lock you up to wait his arrival. There are also a few things I need to go over with you in the terms of safety.”

Dressing Mistress was pretty easy. Most of what she needed to wear was already on her habitually so it was just a matter of tightening and adding some final touches. Once I finished helping her, about 10 minutes was left before the client arrived.

She led me over to a hanging pillory. It looked like two railroad ties with cutouts for my neck and hands. It had eyebolts attached on the top and was suspended by chains from the ceiling. It allowed me to crouch a bit and I could bend from the waist if I tried. She opened it up and I slid my wrists and neck in place. She closed and snapped the lock closed over the hasp. I was secured, and feeling really helpless.

She got a pole with cuffs on either end, about three feet long. She attached one cuff to my ankle and then helped me slide out my other ankle so she could close the cuff around that. “This is a spreader bar. It is designed to prevent you from closing your legs together. It also keeps your feet on the floor and can help you stay balanced as long as you don’t move. If you fall, that’s fine, you are secure enough that you won’t damage yourself for the next little while. Just pull against the restraints and stand back up.”

As she was speaking, an eyebolt on the floor was locked to an eyebolt in the middle of the spreader bar. She also ran some bungee cords from the bottom of the pillory to additional anchor bolts in the floor to help me keep my balance. I imagined that the tension on the chains over head was pretty tight.

She pulled my hair back in a pony tail to keep it out of my face, kissed me lightly on the cheek, then shoved a ball gag in my mouth and buckled it behind my head. I immediately started drooling and couldn’t help it when it spilled out of my mouth.

“Okay, now for the safety lecture. Normally we would come up with a series of ‘safe words’ for you to say that would back the action down or stop it if needed. A ‘caution word’ is there to let me know that you are need a bit of a respite, but not all the action needs to end. A ‘stop word’ tells me that you have to have the scene end RIGHT NOW due to whatever reasons, medical or emotional.

“Since you have that gag in your mouth you won’t be able to say anything, and I might not be able to see your hands if you are signaling that way. So tap your right foot if you are using the ‘caution word’ and the left foot if you need to use the ‘stop word’. Try that now.”

I carefully tapped my right foot several times, by pivoting up on the heel. It was a bit awkward but doable given the way the bonds I was in were set up. I heard Mistress hum in acknowledgment and then I tapped my left foot the same way.

“Good, I can see that and it’s obvious. If you feel you need me to back down please use those signals. If you don’t, I will be MOST irritated with you.”

She picked up the flogger she was going to be using on me. “As you know this is my favorite flogger. Part of why you are in the corset is to protect your spine, your kidneys, your liver and so on. I’ll be hitting you with this on the shoulder blades, not as hard as possible, but hard enough to make an effective sound.

“I’ll also be striking your ass and the backs of your thighs. It will be a thumpy sensation, not a hurtful one, like you got punched over a wide area. The worst that would happen is a sunburned sensation.

“I’ll also be striking your upper torso so that the tails are hitting your ‘tits’, while that would really hurt a female, since yours are prosthetics it will impact and you might not feel anything. I do need you to be a good actress and squeal and jump like you are being really hurt badly. Crying would be good too, but I understand if you can’t manage that.”

There was a knocking at the external door and Mistress hurried off to get it answered and start the scene with the client.

I really did trust her not to hurt me. Which was a strange thing for me to think since *I* was the dangerous person here, not her. The restraints made me feel absolutely helpless. My hands were about two feet away from my head and no amount of straining would get them any closer to each other.

I tried to lift my feet, but the spreader bar was doing a marvelous job of keeping my feet at a constant distance from each other. Given the lock holding the bar to the there was a lever action that kept my heels firmly on the ground. If I tried hard enough, I could probably bend or break the pole, but I didn’t want to cause her more expense or pay the price she might extract from me for damaging equipment.

I used a soldier’s trick and relaxed. I just let my thoughts drift, and I kept my muscles from freezing up by individually relaxing them all. Thankfully the room was warm, so I wouldn’t have to worry about cramping from the cold. As best as I could I kept the blood flowing and moving in my body by shrugging my shoulders and my arms. I swung the pillory back and forth so that I had some movement of my back and tried to wait Mistress out.

***

Based on the report from the company’s first sergeant an investigator had been assigned to check out SSgt. Taylor’s quarters and electronics including Taylor’s personal computer. The CID investigator thought, “Clever people are sometimes the most stupid of all. It is all well and good to keep a password on a computer, but if it’s easily guessable, then it’s useless”. Unfortunately for Sergeant Taylor he was one of those clever people.

The man who was had entered SSgt Taylor’s room didn’t have to wear black or a ninja costume. He had the keys and as a member of the Army most people wouldn’t think twice about his presence. The CID man had verified the fact that Taylor was once again off base during his time off. It was a caution flag to the investigator. Taylor’s routine had changed recently and needed to be checked out. The man moved to the desk and pulled out the USB key he had.

First things first, he started up the operating system and got to the password prompt. He hit a sequence of keys on the pad and found the administrator account wide open. He used that security hole to pull open the Admin account which gave him access to everything.

He knew that SSgt Taylor had been going to some sites that were “questionable” while using the base internet, but he wondered about the sites he visited while on the DSL line he had running to his quarters.

Ten minutes later, he had his answer. It was easy to find the encrypted file that SSgt Taylor had used by searching for which files were accessed recently that were NOT operating system files. Taylor had done a good job of clearing the caches and footprints from his Internet history, but there were a lot of ways to find information if you knew what to do.

Those files were encrypted, so he used one of the password crackers that he brought along with him. It was interesting that the encryption used wasn’t very strong, although it was a good cipher. Forty-bit encryption was so 20 years ago.

Once the file was open, it didn’t take long to find out what kinds of sites the sergeant was visiting. There were sites about cross-dressing, men being women, stories of Transsexuals and even some bondage. The investigator copied the whole file and re-encrypted it with the tools on the PC. He noted the password to the file and where it was stored in the computer on his USB key.

He continued searching and found even more files, this time of pictures and stories saved on the local hard drive. They got copied as well, and even though they were encrypted just as the first file was. When anyone uses the same password for everything, it’s REALLY easy to open all the protections someone thinks they have.

Two more things and he was done. First was the installation of a keylogger program with a tracking tool to keep an eye on what Taylor was doing on this laptop. Second was to dump the contents of the hard drive to a ghost drive on a secure Army network for an exhaustive analysis.

If he was sharing secrets with the enemy, they would find out.

Just to make sure, the investigator logged in as Taylor. The user ID came up as it always did on a reboot, and he tried the password that Taylor used and found that he couldn’t log in at least it wasn’t the same password as the encrypted files. If it had been the investigator would have lost all respect for Taylor.

It was time to head back to his office and print up the files as evidence. It was going to be an interesting night.

Sissy's Trial -- Part 10

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Femdom / Humiliation
  • Identity Crisis

Other Keywords: 

  • BDSM

Permission: 

  • Posted by author(s)


Sissy’s Trial -- Part 10


By Maid Joy

I was impressed by how well Sissy was doing. It was an intense scene; spanking and really mind fucking the client. Sissy was my main canvas now.

I had the flogger in my hand, and it sounded divine. I would hit Sissy’s back, on the shoulders and she would squeal like it really hurt her. This flogger had loops on the ends instead of tips, so the two strips of leather hitting each other would make a huge “POP” and sound as though it really hurt, yet the actual hit was relatively light.

I say “relatively” because any time you hit human flesh with something else, it is going to hurt and leave a mark. However, I had practiced long and hard on clients and the occasional play toy and knew my own strength and how to gauge the impact I was having.

Sissy, the little slut, was the perfect actress. She kept squealing and shaking to really sell the strikes. I would occasionally pop her ass with the flogger, shoving her forward and making the pillory rock and swing.

I was doing all the talking, yelling at the client and occasionally striking him with the flogger or the riding crop. I finally pulled him out of the chair and threw him over a spanking bench, making sure he had an unobstructed view of Sissy’s face. Because he was face up, with his hands tied over his head to the bench, and then his ankles tied to the other end, leaving his chest and thighs hideously exposed, he was very easy to play with. In order to see Sissy, he had to hang his head off the end of the bench and look at her upside down. That kept him disoriented and even more off balance.

This was the fun part. I loved watching him writhe and screech trying to get free while I flogged his breasts and his thighs and threatened more intimate parts of him. But it was really fun when I left off with him and moved over to Sissy.

The little minx looked like she loved this. When I stroked her back, I dug my nails in some so she would squeal. I would grab her breast, and even though she couldn’t feel it, she would scream into her gag, which would make the client go nuts. But Sissy had some reactions to what I was doing also. I had a good view of the area between her legs, and if the moisture dripping down from under the chastity belt was any indication, she had orgasmed once and was close to cumming again.

Things went very well and I knew the client was thrilled. He was babbling as I let him out the door and I had no doubt I would hear from him again and soon.

I went back to Sissy to do the Aftercare.

***
My hands were very cool. Not cold, not blue from lack of circulation, but cooling, which meant I needed to move them. But Mistress wasn’t back from letting the client out.

I had to think about what happened. I was VERY aroused and really horny. I thought I had cum in the chastity belt, and I wasn’t certain if I didn’t like it.

My head was swimming. I wanted to play with myself desperately and I really wanted to feel this again.

I wished my breasts were real. I wanted so desperately to have Mistress rubbing them and to actually feel her touch on my breast. I had imagined that I could feel her hand on the nipples when she was pinching and tugging, and I knew my imagination wasn’t close to the reality of the sensation.

I spent a few moments with my eyes closed dreaming of what it would be like to be a real girl and to be feeling this; to feel Mistress’ hands on my body, with her flogger on my back. I wanted to feel the more hits. I found something in me that I didn’t know was there. I wanted to feel the pain, to be hit and to see just how much I could take.

My head was swimming, I didn’t know up from down anymore.

I heard high heels coming in, and I knew that Mistress was back. My heart leapt, and if I had a tail, I would have been wagging it.

I felt her hand stroking my back, where she had been striking me with her flogger. “Mmmmm, that looks so beautiful my dear. I love seeing you like this.”

I mumbled something into my gag. “Oh,” she said, “that sounds like you want some more. Do you want some more my little Sissy? Want to be punished and forgiven for some sin?”

I shook my head emphatically ‘no’.

“Oh, not punishment or expiation then perhaps you find you like the pain? Want some more?”

I didn’t respond because while that wasn’t the whole answer, it was part of the answer. I did want more because I liked it.

“Oh, I see, you want to try the whole ‘how much can I take’ thing, don’t you? See if you can endure what I give out? I’d be happy to do it, but I’m not too confident that you can take it. Do you want to try?”

I grunted emphatically and nodded my head as much as I could.

“Alright, we will try this. I need to move you over to the Saint Andrew’s Cross. Here we go.”

She unlocked the pillory and detached the spreader bar. She spent a few moments chaffing my arms and legs to get my circulation back and she helped me over to a big X in one corner. She pushed me up to it, so I was resting against its padded surface, with my head resting against a pillow on the cross.

She spent a few minutes pulling off my corset. I was sorry to feel it go, but I trusted that she knew what she was doing. She helped me pull off my heels so I was standing on my own feet. She took the gag out of my mouth and wrapped my arms around the cross. “Same safe gestures if you need to use them, okay?” I nodded.

The next few hours was wonderful. She started slowly and worked up to more severe floggers and heavier floggers. She had a flogger that was really stingy it felt like my back was being flayed. She kept going and something happened in my head.

It was like I pulled away from my body, getting lighter and more detached from everything. It was weird. The sounds went away, the music playing went away, the things that Mistress was saying to me went away. All that remained was the ‘thump, thump’ on my back and buttocks. She kept striking and the pain faded, replaced by this feeling of expansion.

It felt as though I merged with the cross, and I was one with the flogger, and it was wonderful. I had no body, just this floating sensation. She could have keep hitting me forever and I wouldn’t have cared.

Eventually, there was a bright light in my eyes, I was dimly aware of being moved. Finally I wound up lying down with a blanket around me. I was still floating and didn’t care. I wasn’t cold, and when I could feel my body again, all my extremities were fine.

I kept the sensation of floating almost flying after a while, it changed to a feeling of being five or six inches outside of my skin. I didn’t have a care in the world. I swear I the boobs on my body felt real and wonderful. It was hours before I felt anything like “normal”.

I was hyperaware of every part of my body, from the locked up male member that made it easy to forget that I was anything but Sissy, to the paint on each toe and the extension of each nail. I could feel each thread on the blanket I lay upon, and the direction of the gentle zephyr that came from the ventilation.

I felt as though I had been reborn. It was almost how I felt getting through the CS Gas chamber, like I had accomplished a fantastic feat and come out the other side made new.

I lay there and just existed for a while.

***

Mistress cared for me. She steered me into the kitchen eventually, still wrapped in my blanket and gave me some things to eat and drink. Eventually I did come down off the high.

“The state you were in is called ‘subspace’. It is a place that many try to get to and some achieve. I’m glad you could get there. You were wonderful.”

The words meant something but I had to wait for it to make sense. That took time, some tea, and more food. And finally I was able to understand what Mistress was saying.

But it was a letdown to not feel like a girl anymore. Maybe someday soon.

***

I had some time on my pass left so Mistress and I decided to go shopping. I was up for it, not that I needed anything, but the trip out as Sissy always made me feel good.

I pulled on a black knit skirt that embraced my legs like a lover. Above it I was corseted again, with a pretty cream-colored turtleneck and peach sweater. I added some bangle bracelets and a couple pretty gold necklaces on top of the sweater. Finally, I added a leopard print scarf and used it as a sash.

I grabbed a purse that matched the scarf and put my necessities into it. I pulled on a pair of two-inch heels and touched up my makeup. I looked myself over carefully in the mirror. I could still see the male in me, but I hoped no one else could.

Feeling like my soul had been bleached pure again, I nearly skipped out of the house to the car.

***

I was parked down the street. My orders were to follow SSgt Taylor and to report on him to my superiors. I’d been doing this all weekend and it was honestly boring.

I had seen him go into a nondescript house on Friday evening and he hadn’t been out since. People went in, they came back out again. I had pictures of all of it, but there wasn’t anything about them to make an investigator nervous.

I noted every detail I could, including the house number and times people arrived and departed. I had done a bit of investigation on the Internet with my laptop and found that the house was owned by a Karen Lander. Tax returns showed that she lived in her place of business. I did a bit more digging and found that her business was apparently sex related, although she didn’t have a record of prostitution. Given some of the invoices I had access to through the FBI and their intercept program, I knew some of the deliveries that came into the house, were BDSM oriented gags, collars, cuffs and things like that. Really pervo sex stuff.

While waiting I made a call to my superiors to arrange for the interception of her mail I wanted a look at what billing invoices she sent and received. I’d start to get those reports when I got back to base.

The door opened and two women came out, heading for the car in the driveway. I grabbed several photos of both of them, since they were lookers. One was Ms Lander the other was a lady I hadn’t seen go in. Maybe she came in a back way. I would have to arrange a static surveillance op to cover that.

Didn’t see SSgt Taylor, so I hunched down in the seat as they drove off and I waited to see if he came out. His car was still there after all.

Sissy’s Recovery -- Part 11

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Disguises / On the Run / In Hiding
  • Identity Crisis

Permission: 

  • Posted by author(s)


Sissy’s Recovery -- Part 11


By Maid Joy

The next several days were very hard for me. The duty in the Army wasn’t hard, but it was difficult changing back into my “he self” after the scene the other night. I felt different, as thought I had completed some rite of passage. Coming down from that took discipline that I knew I had, but that I felt very reluctant to use.

I threw myself into my work. There was always training to do, skills to be honed, competitions to hold and the other ordinary activities of a platoon of warriors. I continued to supervise people, take care of arguments as they happened, all the while continuing to keep my body in top male physical form every day.

Just because I was “bewitched bothered and bewildered” didn’t mean anything stopped.

So I did what I could and the very routine of the week finally grounded me out. It took some time, but it worked.

While going through this no longer normal routine, I had time to think. I was still confused as to who I was. Was I SSgt Taylor, Ranger, Marksman, expert in many forms of combat, or was I a girl trapped in a man’s body? Did I want to give up the recognition I had to try to gain something I might have had?

Did all this that I was going through confirm or deny my childhood?

The rage and anger my “he self” learned as a child had been channeled in a productive way by my service to my country. The enemies my government directed me to suffered, not innocent people. Yet, my core, my “she self” was denied, crushed, ignored by that very outlet.

As mad as it sounds, the only time I didn’t feel like I was acting was when I was simply being myself with Mistress whether we were with clients or not. Helping mistress talking with her, shopping, doing all the day-to-day things that “real” ladies did. That was the real me the true me.

I’ll admit that I wasn’t the best at being a girl. Heck, I didn’t have much but I was learning and improving making me feel like one person not two for the first time in a long time. I had come to realize how much I needed that part of me and how much it completed me. It made me whole.

I didn’t want to give up SSgt Taylor either. He was just as important to my psyche as Sissy was. I enjoyed being as physical as I was, I enjoyed the competition on the field of battle, with the victor living to fight another day. I understood how addictive the adrenaline rush was to the gamers, and this took it from the virtual world into the real world. Instead of pixels running, it was my own flesh blood and bone. If I failed there was no reset button, no other life for me and that added to the endorphin high I felt. It made the down time, the stateside time bearable to my “he self”.

As always, my thoughts circled around to “nothing can be done”. I couldn’t finish any a transformation to female while I was in the Army, I couldn’t stay SSgt. Taylor out if it.

***

Halloween came and I was back at Mistress’ house again. True to her word she had a costume for me, female officer, all the proper ribbons and hash marks on the uniform.

I held it up and looked it up and down. “How did you get this?”

She snorted. “I called the uniform store, asked for a Captain’s uniform, gave them sizes and awards, all the citations and so on and then I picked it up a little while ago. It really wasn’t hard.”

I held it up to me. It did look like it would fit properly. I examined the awards and citations. Good Conduct for 10 years running, standard medals for various duty oriented things, matching my own set of citations. Expert in pistol, rifle and grenade, sharpshooter, it was almost perfect. If I could have added my combat cords and citations it would have been perfect.

I carefully laid it all out. Just about everything a female officer could need.

“Here, let’s get you dressed properly.” In no time she had me in my skin and I was pulling on my “she self” undergarments. First the padded girdle, giving my butt and hips a softer female shape, then the corset and bra. I noticed I was breathing in short gasps from the corset. They weren’t regulation, but I doubted anyone would be inspecting me closely enough to discover that fact.

A camisole came next, covering the corset creating a smooth line. Next I pulled on the hose and attached them to the girdle garters. Now it was time for the outerwear. The blouse slid up one arm and then the other, settling around my torso. I started closing up the buttons, the backwards motion almost second nature. It was meant to close all the way up to the throat, no low cut blouses in the military thank you. The tie was next, a simple snap under the collar.

The skirt slid down over my arms my torso almost floating to my waist. I noticed the material of the skirt matched the jacket, thick and heavy. I was glad the skirt was lined; I couldn’t imagine how rough it would feel against my hose covered legs without it.

I turned and saw myself in the full mirror. All I could say was “oh wow”. Girls were right that a military uniform really looks good. I pulled the shoes on, only a two-inch heel, but highly shined shoes as per regulations. Finally I picked up the jacket and pulled it on.

Man, my “he self’s” Class-A’s didn’t look this good. It was true I had more decorations, but this looked wonderful. It was fitted at the waist, giving me a nice hourglass figure, the green was just the right shade to go with my skin tone, and I looked sharp.

The gold oak-leaves were just the icing on the cake. The whole ensemble looked perfect.

I only had two more things to put on, the cap and my purse. Regulations stated that it was a black utilitarian purse, and that is exactly what I had, functional and sturdy. It too was polished to an eye-blinding shine. I looked inside and found all my accessories, makeup wallet and so on.

I pulled on a short, red wig and then I grabbed some glasses and pulled them on as well. That was the perfect touch. Habit kept me from putting on the garrison cap until we were outside, but I think I cut a pretty fine figure.

Mistress came to inspect me after putting on her Playboy Bunny costume. “Oh, my, don’t you look dashing.”

I curtseyed a bit while saying “Thank you. May I say you look hot? I mean, if I were a red-blooded man, I’d be all over you.”

“Sissy, you are a red-blooded man, at least until we get you on hormones and some surgeries.”

Something must have shown on my face, because she became very solicitous. “I didn’t mean it that way. I mean… what I meant to say….”

I shook my head. “It’s okay. I understand what you meant.” I sighed deeply and smoothed my skirt as I sat down on the chair which was nearby. I turned and checked my makeup and made sure it conformed to military standards and fiddled with a blush brush. Mistress was quiet behind me.

“I don’t know what I want to do. I’m at the point of looking at the rest of my life, I’m not sure I want to stay in the Army or if I want to leave it and become a girl all the time. I don’t even know if the Army will let me stay IF I decide to try to transition. Hell, I don’t even know if I want to complete the physical transition.”

I looked down at the make up table in front of me. “Don’t get me wrong, I love being Sissy. But I’m still Gregory Taylor, a Staff Sergeant for the last year, and even more than that, male for the whole 27 years of my life. When it all comes down to it, is this just ‘dress up’ or is this who I am and who I should be for the rest of my life?”

Her hands touched my shoulder and she looked in the mirror at me. “Honey, Sissy, Greg, whoever you are, you are my friend, my sister, and I enjoy your company. Right now, let’s go to the costume parties like we planned and think about these life-changing decisions later.

“But whatever you decide, you are a good person, and you are ultimately who you are.” She leaned over and kissed my cheek.

I felt moved to tears, but didn’t cry. I wanted to, but the thought of spoiling my look and turning into a raccoon stopped me.

We gathered our purses and headed out to go to the party.

***

SSgt Taylor was definitely in there, and now that I knew that he was a cross dresser, it would be my job to gather the evidence that would lead to his deserved much-less-than-honorable discharge.

I saw the subject and its friend come out of the building and move to the car that Ms. Lander owned. I saw SSgt Taylor in the Class A Greens of a female officer. I grabbed the camera and started shooting pictures. I made sure to get pictures of Ms. Lander, the subject and the two of them together.

It was serious now. The evidence would have to be gathered carefully and completely. The Staff Sergeant’s military life must be terminated for the good of the Army.

Sissy Destroyed -- Part 12

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Caught with Consequences
  • Identity Crisis
  • Real World

Other Keywords: 

  • Halloween
  • Uniforms

Permission: 

  • Posted by author(s)


Sissy Destroyed — Part 12


By Maid Joy

The party was great. Halloween was my favorite time because you could be whomever you wanted to be, your wildest fantasy come true. The humblest, most repressed person could step out as the most bizarre, most brazen, most outrageous creature they could imagine without fear of persecution.

I knew enough now that I passed easily as a woman. Things might have been different several months ago, but not now.

I kept getting salutes from other people in Army costumes, most of them jokes, but the few serious ones made me a bit nervous. Impersonating an Officer was a serious offense. If someone thought I was really trying to pass myself off as a real Officer, not just play one on Halloween, I could be in a shitload of trouble.

I had a fun time. Mistress and I danced with other men, danced with each other, and I felt like a princess for the first time ever. I just relaxed and let myself go, swirling around, eating snacks, drinking and having a good time. I think I laughed more than I have in quite a while.

I was called “Major Tailhook” several times, referring to the scandal of a few years back. Hopefully no one would try anything.

I knew that it was very possible someone might try something stupid like groping or even rape, so I did my best to keep my wits about me. I never finished a drink that I left, I didn’t go anywhere alone, and I didn’t go to anyone’s room. I hadn’t been to a “stay safe” class, I had seen enough on TV and in stories to know those basics.

I think I was a bit freer with the booze than was wise, but I really did want to relax and being a bit tipsy felt right, like any other girl out to have fun. I wasn’t drunk, just had a nice buzz when Mistress and I left around 2 AM heading home. We went to our car around the corner under a light since we couldn’t find anything closer to the party.

“Oye chicas, come with me maybe you don’t get hurt.” The voice growled from behind us. He grabbed my upper arm and Mistress and I were herded into an alley. As hard as it was I cooperated since I felt a gun barrel in my back.

Mistress was like a robot, moving stiffly. I could tell she was frightened, and I knew that there were all kinds of negative scenarios going through her head. I grimaced and said “We don’t want any trouble.”

“Good. Do what I tell you, you be fine. I want everything you got.” Once off the street, he shoved me and I pivoted to face him.

I could see the gun in his fist. The part of me that was still rational noted it was a Smith and Wesson Model 64 Revolver. I could see the hammer cocked and his finger was on the trigger. Not good. He was ready to shoot. Time slowed as the adrenalin pumped into my body.

I made it my business to look closely at him to memorize his description. Latino, about 18, dilated pupils, high on something, Chinese symbol tattooed on the back of his right hand. The catalog continued, 5 foot 10, about 140, dark hooded sweatshirt with pocket compartment in the front, band logo on the chest, faded blue jeans torn on the left knee, Air Nike, about size 10 male shoe. Shaved head.

I saw his hand come up leveling the gun at my face. “Stop looking at me bitch, or you gonna lose the ability to see anything. Gimme your purse.” He took the purse out of my hand and reached in blindly to grab my wallet. He dropped the rest and then turned the gun on Mistress.

I didn’t think, didn’t plan, I saw the gun in her face how badly she was shaking, I acted.

My right hand snaked out and grabbed the top of the gun, making sure to jam my hand between the hammer and the firing pin. I felt a hard pinch as the hammer fell, it just made me more coldly furious. I twisted the gun to the left, turning the barrel toward the back of his hand and away from Mistress and myself in what looked like slow motion. It felt like I was back in the practice ring, calm cool just another practice. Simultaneously, I pulled his arm close to my chest in a classic Jujitsu move; locking his elbow and breaking his trigger finger while I twisted the gun out of his grip. He should have let go.

Once I had the gun in my possession, and his arm secured, I twisted his wrist down in an arm-bar, bending him over by the waist making his arm shoulder and wrist hurt a LOT. He yelled, loudly, but stopped suddenly as my foot connected with his face, breaking his nose and snapping his head back. I continued twisting his arm down helping him reach the ground pushing on his elbow, forcing his face down into the pavement, hard.

I felt more than heard bones in his cheek breaking, but he was still conscious and capable of moving, so I continued the rotation of his arm, dislocating it at the shoulder and popping his elbow out of its normal L shape.

In seconds I put the foot that kicked his face down on the pavement, braced and raised my other foot and stomped his closest knee, dislocating it if not breaking the kneecap. I felt his joint pop and he lay on the ground screaming in pain. It felt like I had been moving this fool to the pavement for the last hour.

I released his hand and stepped back a bit to see what he would do ready to continue neutralizing him. He was on an unknown amount of an unknown drug, if it was PCP he could just get up and keep coming at me, know way of knowing. He lay there moaning while I inhaled slowly and heavily as I tried to come down off the adrenalin rush. I turned to Mistress, who was still shaking. “Karen, you have to call 911. I’ll keep him covered. Call them now.”

I carefully lowered the hammer on the pistol so that it wouldn’t accidentally go off. My hand smarted from where he had reflexively squeezed the trigger and the hammer had snapped closed on me. Mistress might have been died if I had failed. The pain and the bruising was a small price to pay for her life.

I squared up to a proper stance keeping the hammer down and my finger off the trigger, knowing this particular pistol was double-action. I had to keep talking to Mistress to get her to dial, but eventually she made the call to the police.

***

Sitting in a police station in drag is not a fun thing to have happen. When they arrived, while they were solicitous of the near tragedy, they still had to take me into custody since the would-be mugger was the one injured.

I sat there in the interrogation room waiting for an interview to make sure the story in the report was accurate. They had separated Mistress and I so we couldn’t compare stories and the mugger was taken to the hospital. Apparently I really over-reacted and he would be off the streets for some time.

Finally someone came in. Standard questions were asked, and I was asked to tell my side of the story. I had to clarify for the record that I wasn’t Major Taylor, as the insignia and nameplate on the uniform indicated, but SSgt Taylor, male. I explained the whole thing about the Halloween party and why I was dressed as a female officer.

Once I finished the explanation, he complimented me saying that I fooled him and everyone else in the precinct. He made some notations and then wrote my story down. He had me repeat it three times, just to make sure it didn’t change.

After about five hours of questioning, he finally let me go. I sat and waited for Mistress to show up since they were also interviewing her asking the same questions. I knew that I didn’t have anything to hide, and the truth was all I told, but I was still nervous since I only had experience dealing with Military personnel and not from this end of things.

Finally Mistress appeared. She looked white and I knew she was going into shock. I had to get her home soon.

We got our possessions back and left. A short ride with the officers to our car and the drive back home ended the night. I knew Mistress was upset and might even still be shaking, I would do anything I could to comfort her.

I had stayed in control when we got home. Curiously she seemed very obedient. I got her undressed and into a nightgown. I got her into bed and then I got myself ready for bed. For the first time ever I got in to bed with her. I held her and I comforted her the best I knew how. I knew from personal experience what that first brush with death was like, and I held her while she cried out the stress.

Somewhere around 9 AM we finally fell asleep together.

***

When we woke up, it was about 2 PM. I had the day after Halloween off also, mostly because those of us who were going out the night before needed the time to recover from overindulging. So those that were off on the 31st were also off on the 1st. It meant that I would have to serve on some other nights, but that wasn’t really a big concern to me.

I quietly got up and made breakfast/lunch for each of us. I made sure it was fortified and that it would be healthy for Mistress as well. I made sure it was high protein, low fat, with fresh fruit to round out the meal. No caffeine, no stimulants of any kind. I wanted her to go to sleep at about 10 PM, and since that was only a few hours away, it would be a coffee-less day.

I arranged it on a tray and quietly took into her bedroom and then gently woke her up by kissing her cheek. With a flourish worthy of the Maid I was, I served her breakfast in bed.

I think it went a long way to helping her restore her balance after the nightmare end of the party.

We talked about everything that happened. I tried to focus on going out in public to a party, the dancing and the fun things, trying to make her realize that the party is what she should be dwelling on rather than the horror.

When her potential death inevitably came up, I made light of the situation. “Mistress, how could you die? I was there with you. I would never let that happen.”

While that was true enough, I didn’t want her frightened anymore.

***

The First Sergeant looked at all the files on his desk. First the copy of the civilian Police Report concerning an incident involving Taylor after a Halloween party. Second were surveillance photos taken by CID several days in a row. Third was the report on Taylor’s computer records. He wanted to tear his hair out with frustration.

“As you can see First Sergeant, we have more than enough to prosecute Staff Sergeant Taylor,” the CID investigator stated, “Since you asked for this investigation to start, my First Sergeant ordered me to bring this to you first.”

“Most damning is the Impersonation of an Officer charge. Note please even though later in the investigation, the actual identity of Sergeant Taylor was verified, the fact that he initially responded as a female to ‘Major Taylor’, and allowed that to be written in an official report is really all we need. The homosexual activities are just icing on the cake.”

The CID investigator was serious. “If you decide not to do anything, I am under orders to report all this to the Judge Advocate General to take action. He will be prosecuted to the limit of the UCMJ and discharged from the Army. I bring all this to you as a courtesy. I have been instructed to tell you that you have 72 hours to decide what to do.”

He came to attention and left the office, leaving behind copies of what he had brought.

The First Sergeant had no doubt that they would remove Taylor from the Army in the most humiliating way possible. But might be another way.

He gathered up all the folders and documents, put them back in the files and went to see Captain Richardson.

Sissy Vilified -- Part 13

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Caught with Consequences
  • Blackmail
  • Identity Crisis

Other Keywords: 

  • Military
  • Uniforms

Permission: 

  • Posted by author(s)


Sissy Vilified — Part 13


By Maid Joy

The First Sergeant stood in front of his Commander’s desk. Captain Robertson was normally a jovial kind person until it was time to get serious. From the lack of a smile on his face, it was time to be serious.

“This is no good Top. I never would have pegged Taylor for being one of them. It’s as shocking as anything I’ve ever seen.” He sighed heavily and put the files aside. “Have a seat. What is your recommendation regarding this situation?”

The First Sergeant sat down in one of the office chairs. His heart was heavy, he hated this part of being a commanding officer, but decisions were required and expected. “Don’t Ask, Don’t Tell” might be the standard line, but in reality, evidence like what was in those folders demanded action for the good of the unit.

“Well, Sir, while the Army can’t prosecute him for homosexuality since no concrete evidence is indicated. This whole dress up thing is going to label him queer no matter what. Once the men start questioning his sexuality, discipline will destroyed. If he can’t maintain that, he’s useless.

“Our options are very limited Sir. We could transfer him to another unit, but unless there is a compelling reason for the transfer, it’s a red flag anyone given his service record. There’s no real reason to shift him to another unit. If we promote him to another slot and transfer him that’s rewarding him for being gay.”

“Yeah, that would set a bad precedent. Not something that I want to do.” Captain Robertson fell silent.

“The next option is to just let JAG prosecute him under the UCMJ for impersonating an officer,”

The Captain cut him off, “But that situation would do a hell of a lot more devastating to everyone. Here we have a combat hero, cited several times for bravery under fire, having just saved the life of a lady during a mugging while off duty. This will make us look bad in several different ways, even as it destroys his career.”

The First Sergeant nodded. “That’s a problem, Sir. Whatever we do in the situation it will mess up the unit and could affect the Army as a whole for some time to come. You know it’ll get out.

“We could try to cut some sort of deal with the JAG to stop everything, but I’m not sure that would be effective.

“I think there might be a solution it’s dicey and I’d need your approval, but it could work and save everyone a lot of trouble....”

***

It had been several days. Sissy kept in touch with Mistress so that he could make sure she was okay. Traumatic shock didn’t just happen in combat and could have unexpected consequences as time passed. He was very aware of the possible stages that could happen. He’d been through some of them and as a Staff Sergeant; he helped others in his unit through them too. It was his job to keep an eye on everything.

Mistress had gone through several crying jags. Other friends came over to keep an eye on her while Sissy was on duty. Still whether his “he self” was out on the range or in the Ready Room, she still called Mistress to make sure she was all right.

Two days after the incident Sissy put in for five days leave to spend it with Mistress. It was important to Sissy to make sure she was there if the Post Traumatic Stress hit Mistress and she woke up with nightmares.

It wasn’t a question if there was trauma, it was a question on when an episode might be triggered.

Taylor was back in his room doing some paperwork. There was a knock at the door.

“Come in.”

A private entered. “Staff Sergeant Taylor, the Captain would like to see you in his office immediately.”

Taylor got up and checked his uniform. It was clean, pressed everything was in regulation order. He followed the young man down to the Company Headquarters.

He entered the office, made his way to the Captain’s office. He knocked on the door and heard “Come in.”

He entered and saw the First Sergeant in the office. He came to attention in front of the Captain’s desk and saluted. “Staff Sergeant Taylor, reporting as ordered Sir.”

“At Ease, Taylor.” He snapped into Parade Rest, and waited for the Captain to address him. He wasn’t smiling and that was a bad sign. Captain Robertson turned to the First Sergeant. “Top, this is your party, get started.”

The First Sergeant came over and ordered him into a chair. Taylor made sure he was facing both the Captain and the First Sergeant.

“Taylor, some information has come to our attention that needs to be addressed. We called you here to give you a chance to respond to it.” The First Sergeant pulled out a folder and handed it to Taylor.

Taylor had been expecting to see something about one of his men and was making a mental list as to who it could be and what he would do to them. Then Taylor opened the folder and saw Sissy staring back at him.

His heart jumped into overdrive. His vision tunneled down to just the photo and there was a roaring in his ears.

Hands that didn’t seem to belong to him turned pages, read reports, went through the notes made by the investigators, times and dates. Then he saw a copy of the Police Report from the incident on Halloween.

Sissy started shaking.

The First Sergeant and the Captain had been silent while he read through the file, probably giving him time to digest the information.

Taylor closed the file; he just sat there. The Captain looked sympathetic, but hard. The First Sergeant looked on steadily. “As you can tell, we have been following you for some time. I asked for the investigation when I noticed you wearing perfume and nail extensions when we deployed. I was concerned. There’s a chance you could be blackmailed into revealing classified information.

“The situation has moved beyond that. When you were attacked on Halloween, the CID reported you as impersonating an Officer. According to the UCMJ is a very serious action as you know.”

He shifted in his seat for a bit before settling again. The First Sergeant continued “A Court Martial is the least that will happen with that charge against you. Since you are a Non-Commissioned Officer and were photographed wearing the uniform of a Major, and because it was noted in the police report that way, you will be found guilty of the impersonating charge and that means a Dishonorable Discharge. You will lose all your benefits, your pension, and anything you paid into any of the programs.

“More than that you court martial would blacken the eye of the Rangers, the 75th Regiment, the 3rd Battalion and all of the men associated with it. While the scandal might not be picked up by the civilian papers at first, it would definitely become a story in the Army. Eventually you know it would all come out.”

I couldn’t argue with him since all that was true.

“Add to that the embarrassment to yourself, your family, the lady you were with and anyone who considers you a friend. Making a public circus out of this would be bad for everyone involved. We want to avoid it IF you make it possible.”

The Captain now weighed in. “Top and I have discussed all the option and we believe the best solution would be you resigning your commission. We will allow you to leave with an Honorable Discharge, your awards, and benefits. However, your records will be noted with an order canceling your Security Clearance and indicating you may never be called back into Active Service. Needless to say you would not be welcome at any Military activity, ever.”

The First Sergeant handed me a clipboard. “We have a letter ready for you.”

Taylor/Sissy read through the single page. It stated that he resigned her position in the United States Army and his Non-Commissioned Officer status effective immediately.

She looked back up at the Captain and the First Sergeant. Tears filled his eyes. She didn’t know what to say.

The Captain said, “It’s simple Taylor, sign that or be arrested immediately and charged with Impersonating an Officer, Conduct Unbecoming a Non-Commissioned Officer and whatever else JAG decides to write into the charges. You’ve seen the evidence for your self. For the good of the unit, for the good of the Army, I strongly advise you to sign that letter.”

She looked back over at the First Sergeant. He looked at me coldly and nodded his head slightly.

Sissy picked up a pen and put his signature above the typed version of her name.

Sissy Reborn -- Part 14

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender

Character Age: 

  • College / Twenties

TG Themes: 

  • Caught with Consequences
  • Blackmail
  • Identity Crisis
  • Fresh Start

Permission: 

  • Posted by author(s)


Sissy Reborn — Part 14


By Maid Joy

I’ve fought through pain. Once on a mission, I landed on a rooftop, right near the edge, it collapsed under the impact of my touchdown and I fell another two stories without my chute and broke my ankle. I had to get up and keep going as I was one four people on the mission, duty and adrenaline carried me through to pick up.

I learned that day that physical pain is easy.

I was back in my quarters. The MPs and a clerk were with me, mainly to take the classified papers away with them and to make sure I didn’t take anything I wasn’t supposed to.

I opened up my locker and removed my uniforms. They were Army property and so I left them on my bed. I went through all my personal items, leaving the military items and issued items plainly visible on my bed. Anything that was a civilian item or something that I purchased was set on my desk. I did keep my medals and citations. I earned them and no one would take them from me without a fight.

As I looked, the size of the piles were very different. The military items were 75% of “my things” I realized I just didn’t have that many personal items. The clerk had gone through my computer hard drive and started deleting items and programs. As I looked, I realized everything on the computer was either a military application or document. As soon as all classified material was removed, the clerk and MPs were able to return to their routine duties.

All my personal things fit into three boxes it was kind of sad for 10 years in the Army.

As I took the paperwork to each department required, and started turning in my issued items I couldn’t help the tears slowly leaking out of my eyes. I was in all sorts of emotional pain. It was the most horrible thing I experienced in my adult life. By then I didn’t care who saw me all I wanted to do was bawl my eyes out.

I had to try to keep a brave mask up for my men. They didn’t know what circumstances were forcing me to resign my commission. They wanted to know, but I couldn’t stand to embarrass the Army, myself or the Unit with the Army’s misconceived version of the truth. I kept it behind my teeth and let the story spread that I was taking early retirement due to unused leave. They seemed to accept that.

I had some problems trying to get out of the party they wanted to throw for me. I knew the First Sergeant and the Captain wanted me gone ASAP and as shredded as I felt, I probably wanted it more than they did. These were my men my platoon, I had sacrificed myself for them before, worried over them cried with them and I couldn’t let the mask slip safely until I was off post for the last time. I had no choice but to acquiesce.

I sent a note to Top, asking if I could take the evening and have the party with the men, to keep alive the fiction of my voluntarily separation. A note saying that was acceptable was returned. Time was on my side and Top and the Captain let me know as long as I didn’t try to access any secured stuff, I could have up to three days to clear the base. The torment of staying was unbearable, I knew it couldn’t last that long.

I couldn’t leave in haste, that might expose my shame to the rest of the world, but I couldn’t survive the emotional devastation of staying on post forever. If I could manage to hold it together it would give me time to say goodbye to everyone I cared about.

You know, I think I finally came to a conclusion somewhere during the party. Fuck ‘em. If they don’t want me in their exclusive little testosterone club, then I don’t want them either. Fuck them all to hell.

I would reflect later how ironic that statement would be. I was pretty tipsy, just a few fingers from really roaring drunk. Holding on was getting really difficult.

I was toasted and feasted, on pizza, and just about everyone come up to me and shake my hand at one time or another. A few of my men were in a “war story” group at the end of one bar talking about what our platoon had been through. Two kids credited me with straightening them up so they could be the soldiers they were meant to be.

Hearing this outpouring of camaraderie (most people would call it love), had made me maudlin again. I promised that I would stay in contact with everyone, even though we all knew that was a load of crap meant to ease the pain. I would go my way, they would go theirs. I wasn’t part of the group anymore, now I was an outsider.

I spent the next day clearing the rest of the base. There was a whole list of things that needed to be done, and packing and turning in items were only one part of it. The Sergeant in charge of the supply house let me keep all my uniforms and boots; I had paid for them from my Clothing Allowance and that made them mine.

We went down the list of items I was issued when I arrived, once they were accounted for and turned in, there was several things left over. Because the Army didn’t issue them to me, they were considered mine. I discovered I had an entire field kit, pack, poncho and so on. I guess I could always use it for camping some time.

When I went to the Weapons Depot, I found I had a couple of forgotten arms stashed there. One Lugar from World War II that I bought for as a collectable, a 9mm Beretta and a nice pump shotgun were returned to me as I cleared that area. I never had a chance to use any of them; they had been purchased one at a time at various gun shows. Regulations required they be kept at the depot. I put each one in its own locked case and locked them in the trunk of my car. I would have to get a gun permit ASAP.

I had my outgoing physical and that was it. Tomorrow I would go down to the nearest major base and to clear the final paperwork that would sever me from my life.

***

I looked at the last piece of paper to be signed in front of me. All I had to do was put my name on it and that was it. SSgt. Gregory Taylor’s death certificate, How do you willingly commit suicide and go on living? As the pain overwhelmed my emotions I numbly signed the document.

I stood outside the recruitment station in civvies it felt wrong somehow. I hadn’t worn anything but Sissy’s clothes and my uniforms for such a long time that wearing a no regulation shirt and jeans was wrong.

I felt absolutely drained. I couldn’t think. I went to my car sat in the front seat. Like a robot I started it and drove off the base.

There wasn’t anyplace I had to go or anything I had to do. I needed to get off the base and away. I drove just drove until I found a place to park.

I got out of the car, and sat on the hood. I just and stared across the lake and up at the stars. I couldn’t think. I couldn’t mourn. I was angry, sad, frustrated, hurt but most of all I was numb. I didn’t know what to do, where to go who I was.

I thought about the pistols in the trunk.

I just sat there.

***

I must have dozed off. I felt my foot being poked by something. I opened my eyes and looked at the lady cop standing by my knee.

“Sir, you can’t sleep here. You have to leave. This park is closed.”

“I’m sorry Officer. I don’t have anyplace to go. I just left the Army and I don’t know what to do now.”

When I said that, the reality hit me and I started crying.

She started to respond, but stopped herself. “Sir, it’s okay,” she said more sympathetically. “Do you have a hotel room, or a friend you can stay with? Anyplace you can go?”

I thought about Mistress. But I couldn’t impose on her. I shook my head.

She grimaced. “If you will lock up your car, we can go down to the precinct and I can see if I can find you a room in somewhere if you want?”

I nodded. I was too numb to care. Hell, being in Jail for vagrancy would be a step up from where I was now.

I emptied my pockets of everything except my wallet, the change in my pocket and the car keys. Everything else I locked up securely either in the trunk or the glove box. I tossed a blanket over the boxes in the back seat and got into her car. The officer kept a close eye on me as I got into her patrol car. I knew she’d seen the gun cases, but she didn’t say anything about them.

We drove to the police station and she took my name. For the second time in as many weeks I was in an interrogation room. I just sat there, numb.

After a bit, she left and came back with a smile on her face. She handed me some coffee and said “I heard your name someplace so I did a computer search. The computer spit out the report of the near mugging from Halloween. I noticed someone else on that report, so I gave her a call. Ms Lander said she would be out to give you a place to stay for as long as you needed it.”

Stunned. I felt like someone had cold cocked me. I couldn’t think. There was a roaring in my ears.

I don’t remember what happened next. I do remember someone babbling, thanking her even as I seemed to have vacated my body. It was like I watching the whole thing from the wrong end of a telescope.

I couldn’t move. I just sat there. I didn’t want anything, I didn’t feel anything. I don’t remember drinking my coffee. The next think I had was when I realized I was sitting in Sissy’s room.

I lost it. I couldn’t stop crying.

***

Mistress was there with me. When I woke up again, I was in my nightgown in my bed, and Mistress was with me. She had apparently held me that night, just as I had done for her. Feeling her spooned against my back again, feeling warm and protected, things took on a different perspective.

Could I start again? Was it possible for Sissy to live all day every day? Was it possible to really be a girl now, totally, instead of a man? But how could I make a living? Mistress couldn’t take care of me forever. I’d have to find something to do to earn enough to feel I was contributing to living here.

For now, I put that set of worries away and I fell back asleep, safely wrapped in Mistress’ arms.

Sissy’s First Steps -- Part 15

Author: 

  • Maid Joy

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Identity Crisis

Permission: 

  • Posted by author(s)


Sissy’s First Steps -- Part 15


By Maid Joy

Mistress was wonderful to me. She tried so hard to make sure I wasn’t alone and that I was taken care of. We were in an odd place since I was trying to do the same thing for her. When comparing losing a job to being attacked the latter won out in my mind. Apparently in Mistress’ mind, the former was the victor.

I gave her the whole story as I could. It took me a couple days to get my brain together enough to be coherent. I wasn’t myself totally and so I probably missed a lot of her reaction to the story, but at that moment I was a bit too depressed.

It was an odd depression too. At one time it was severely down and very much “who cares”, but at the same time, my brain kept making plans. I would be washing dishes with no thoughts in my head and suddenly I would be thinking about the priorities of job hunting. I would be mentally writing my resume’ and formatting it, at the same time I was apparently staring off into space without a conscious thought in my brain.

I didn’t know why, but I couldn’t shake the feelings of personal failure and futility. I knew that I was suffering from something like PTSD, but I wasn’t sure of the exact medical term. I was down and I needed to do something.

“Sissy, I’ve called a friend who is a psychotherapist. She’ll see you in a couple days if you want to talk to her. I’ve written all the information down here.” Mistress’ voice sounded so sweet and so distant.

I knew she was looking out for me. I didn’t know how to operate anymore. There was no rules, no orders and I was floundering, drowning without them. If Mistress hadn’t been there, helping me by giving me some structure and orders, I don’t know what might have happened.

***

Two days later I was sitting in the doctor’s office. She was a petite blonde with model looks and a very compact body. But like most people I associated with being physically small, she had a personality that lit up the world. She was always smiling and seemed to genuinely care about me.

The cynical side of my brain told me that it was probably her professional training to make it appear that she cared.

Nevertheless, I found myself warming to her. I started talking and I didn’t stop. All the stuff that I had been trying to deal with over the past several years, from the desires to be playing hopscotch instead of working on cars, the confusion I felt when I was mean to people in High School, to my decision to go into the Rangers, Sissy, the whole scene that happened in the beginning of October, to losing my life in the Rangers and all that mess, to “what do I do now” came pouring out. I couldn’t stop it.

I was crying well before the end of my tale of woe. I know it wasn’t manly to do so, but I didn’t feel much like a man OR a woman right now. I just hurt.

It was very easy to forget myself and all the masks that I normally wore. I didn’t want to hide any more, I wanted to get help. Lord knows that I wasn’t able to get anywhere on my own, and while Mistress was trying to help, she was as unsure as I was about how to proceed.

One hour turned into two. I talked and cried until I was horse and my head stuffed. The Doctor didn’t say much, but she was obviously listening, encouraging and offering suggestions. I don’t remember the exact thoughts and words said, but the gestalt was some of the problems took on a new perspective.

So I lost my billet; big deal. It didn’t change the good I had done in the past. It didn’t it make the men I had saved somehow dead.

When she helped me realize that, I felt better about leaving the Army. I still hated that they didn’t want me. Despite all of my achievements that the service would find it so terrible that I liked to dress as a woman. I wasn’t gay, yet I was labeled gay. Different is wrong and homophobia runs rampant in the military.

Actually I can understand that. There’s a part of very macho people which wonders what it would be like to be small and weak. But the macho man fears that and anything associated with that. It is almost as though they think they’ll be “contaminated” some how and become what they fear. They’ll lose their masculinity by being around or seeing or acknowledging anything feminine not-masculine.

Real ostriches there. They bury their head in the sand hoping that by doing so they can make it go away. But the “lalalalalaIcan’thearyou” strategy had been a proven failure since before the Greeks sacked Troy.

The doctor pointed out that I could, if I wanted to, become something of an activist for all those gay soldiers who still had to hide. I didn’t know if I was up for that. I wasn’t gay, I wanted to be sexually active with women, not men.

The problem I needed to focus on and deal with first was who I was. Did I want to be Greg Taylor, or Sissy? Who was the most real me?

***

At home later that same day I lay on Sissy’s bed and just thought. I had avoided Mistress for a while, not because I didn’t want to be with her, but because she was another source of confusion for me.

I was so indebted to her that I didn’t know how to get out of it. I hated owing people something. It put me under a personal obligation until I paid it back. She had already done so much for me that I didn’t want to be even more in her debt.

I got tired of lying down and I needed to relax. I pulled off my jeans and t-shirt and decided to take a shower. On second consideration, I drew myself a bath instead. I knew I was more relaxed by lying in the tub that one time.

I started the water and sprinkled some bath crystals in, along with some oils for my skin. I didn’t need to clean myself since I had showered that morning, but I did need to relax and de-stress.

I lay back and floated while the hot water soaked into my pores, soothing my muscles convincing them to relax. If I ever get a place of my own it has to have a hot tub. If it doesn’t I have to get one immediately. Maybe a sauna too. I just floated and relaxed.

My mind wandered a lot while I lay there. I knew that lying around the house like a slug wasn’t a good I needed activity. Ten years in the Army made a weekend off with nothing to do impossible. I resolved to continue my physical training the endorphin high was just too good to miss.

But it left the question of Sissy or Greg? He-self or she-self?

I pushed that question aside determined to see what was available out there for each. After my run tomorrow I would have to get some help wanted ads and start looking.

I got out of the tub after about an hour; the water was cooling down too much to enjoy anymore. I dried myself off and powdered in the right places, luxuriating in the scents I had come to love.

I moved back into my room and finally looked around it again. It was obviously a girl’s room. Frilly pillows, pink, purple and light blue everywhere. There was my makeup vanity and over there was the cabinet holding dresses. All it would take was a few steps to throw away Greg and become Sissy again.

The point of this time was to relax. I didn’t want to have to be the big strong man taking care of everyone right now, I wanted to be someone who was taken care of, and that was who Sissy was. I opened up the cabinet and pulled out a conservative dress, knee length and short sleeved. It looked like a uniform and it was actually a maid’s dress from a hotel. But instead of making it obviously unfeminine and ugly, or over the top sexy, it was conservatively cut, wide lapels, cuffs at the sleeve ends, dark grey and a nice zipper up the back.

It was the kind of quality uniform you would find in a five star hotel. It looked wonderful without screaming “MAID HERE”. Without much thinking I pulled on my small clothes, corset and stockings. Apparently somewhere in the luxuriating in the tub I had shaved my legs. I didn’t even remember.

I pulled the dress on and selected some 3” pumps to wear. I styled my hair as best as I could since that I didn’t have much hair in the first place. A light application of makeup, some earrings (and resolved to get them pierced when I could) and I was ready.

A spritz of perfume in the air, then walking through the cloud on my way out the door and I was finished.

I got into the kitchen and heard distant sounds of a scene going on. Mistress couldn’t stop her life and her finances just because she had a damaged idiot in her care.

I started preparing a meal. I didn’t know or care which one it was, and I didn’t look at the clock to find out. I just started making pancakes from scratch and some bacon strips. I didn’t make a whole lot since I didn’t know if Mistress was hungry or not, but I made enough for her too. Two slices of bacon for each of us, two pancakes each, a jug of syrup and some orange juice and milk. It was a good meal.

I put the meal aside for myself and made up Mistress’ plate as well. I left it on the other side of the island in the Kitchen for her. I settled myself and started eating. Truth be told, I wasn’t that hungry, but I knew I had to eat something.

I finished fairly quickly as it wasn’t nearly the hearty breakfast I was used to eating, but then again, I wasn’t burning 2500 calories a day either. I could get fat if I didn’t watch it.

I walked back to my bedroom and got an MP3 player, put in a bunch of rock songs that I loved listening to, and started cleaning. Apron on to protect my dress and I just did dishes, cleaned the counters and stove, turned on the self cleaning cycle of the oven and then went through the refrigerator make sure everything was neat and tidy.

I didn’t lose all my training though. One of the deadliest things that could happen to a soldier in the field is to let someone sneak up on you, so I kept an eye out for Mistress involuntarily.

She came in wearing a latex outfit, meaning that her client had contracted for an orgasm, Mistress would cause it with tools or occasionally her hand, but she wore a latex bodysuit to keep the mess off her. This meant the dungeon needed a good cleaning and bleaching, and she would be hot and sweaty.

She smiled tiredly when she saw me, and I helped her out of her outfit. Once it was off, Mistress kissed me briefly on the cheek, and put on a robe and sat down to her meal. I took the latex into her bedroom and washed it off inside and out and hung it to dry. I turned on the shower for her so she could sluice off, and then went to clean up the dungeon.

If I could do these simple chores to repay Mistress for her kindness was worth it. Service to my lady for all of her kindness and help was the least I could do.

I smiled to myself as I got her boots, all of them, and started shining them. It was going to be a long night.

***

The smell of shoe polish brought me out of the shower and to the dungeon where Sissy was sitting on the spanking bench shining my boots. She was so focused on the boot that I didn’t want to disturb her.

She’d been busy for a while, three boots were already done and she was working on the fourth. There were only two more pairs to go and it looked as though she wasn’t going to be happy unless she had them at a mirror finish.

“You should be a bootblack,” I said. She didn’t jump or act startled, just looked up a bit and went back to her work.

“I kind of already am,” she said.

“No, I mean in the BDSM professional sense. There are a lot of leather events I go to where they have submissives and slaves who offer service by shining shoes. It gets a lot of recognition and a lot of credit.”

“Maybe I could get a stand in the Airport too, shine your shoes for two bits.” She used a tone letting me know that she was getting her sense of humor back.

“I’m serious. It’s a respected subset of the leather community. But I’m not sure you’re ready for that level of immersion yet.”

She frowned a bit at a scuff and fell silent.

“Mistress, I have no clue what I want to do now. I’m a killing machine. Not many openings for people who kill. The police arrest, soldiers kill. Bodyguards take bullets and clear areas. Martial Arts instructors teach how not to die. I’m not good for very much.” The downcast look on her face had me near tears.

I went over and hugged her. I let the towel fall off as I did. “I think we can figure that out with each other.”

I knew exactly what I wanted her for and what I wanted her to do. All I had to do now was to lead her into that gently.

Sissy’s New Life -- Part 16

Author: 

  • Maid Joy

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Mature / Thirty+

Permission: 

  • Posted by author(s)


Sissy’s New Life -- Part 16


By Maid Joy

It had been two months of hell. Well, hell when I wasn’t at home with Karen. She and I were growing closer in a way I had never been with a woman before. She wanted me in bed with her, and I had been resisting.

Most people would have smacked me and called me absolutely stupid to turn her down, but I didn’t want sex spoiling what we had.

What did we have you might ask. In my opinion we had a very good, and I mean very good, friendship. Not “friends with benefits”, but two people who meshed in just about every way possible. We had similar interests, we liked the same type of music, we read similar books and enjoyed going out to most of the same places. Neither of us liked porn very much (no plots), but erotica turned us both on.

I tried my best to be the perfect roommate. I didn’t make demands on her time; I cleaned up after myself all the time, and cleaned up after her. I prepared meals and didn’t bitch when she left a mess. I figured since she wasn’t asking me for rent, that the least I could do was to clean up around the house.

It helped that I enjoyed housework and I liked cooking.

I had been going out every day looking for a job that paid. Help Wanted ads, leads from the VA, job fairs all the avenues that one takes when looking for a job. I spent 50 hours a week simply looking for employment.

I consulted with professionals about my resume, the people in the Unemployment Office who help vets find work and temp agencies. I didn’t understand why I didn’t have a job.

I was told I didn’t have skills that the corporate world was looking for. I wasn’t a businessman, I had no high tech skills, and I didn’t have any corporate security skills. I could get an entry-level job doing something, but I didn’t want to start like that and lose what I had in training.

My routine became pretty standard. Get up at 4 AM, stretch out, run and exercise for two hours, then come back and clean up in the shower. Make breakfast and eat it, then by 8 AM get busy with interviews and job seeking. That would take me to about 5:30 or so and then come back, dinner, clean up, help Karen with her clients and then get into bed.

My bed damn it. I mean Sissy’s bed. I mean -- my bed. Alone.

Believe me; I’m not made of stone. It was very hard for me to sleep there night after night knowing that Karen was just a couple rooms away and that she wanted me as much as I wanted her.

I’m also not an animal. I used a lot of the discipline I learned in the Army and refused to screw up the living arrangement I had just to satisfy my cock.

But I went though a bunch of lotion and tissues.

“But sir, I am qualified. I have six years in the Army as a Ranger; I think I qualify as a security guard.”

The interviewer sat there with my application in his hand. “I understand that, but the problem is that being a guard is not the same as being a Ranger. We don’t have any positions that require someone with combat experience. An MP or a garrison soldier I could use, they are used to standing around and not doing much, but a combat soldier would get bored really rapidly, and then you would leave. That would leave me high and dry and right back where I am. I’d rather turn you down and hire the guy I need right now instead of two months from now when you quit.”

Well, at least he was honest with me. Most of the other recruiters had just blown me off and didn’t explain things. This guy at least had the cojones to lay it out like it was.

I sighed and nodded. “It isn’t anything I haven’t heard before. Thank you for your time.”

I started to stand, but he stopped me. “I do have a lead for you if you want it. I know a women’s shelter that needs someone to teach their self-defense course. I could put in a good word for you if you want.”

“Yes sir, please do.” He jotted down the number and address of the shelter and handed me the note. I thanked him and left to continue my search.

I figured that I would have to take it, but I wanted to explore all my options.

Three days later, I was out of all the potential jobs that I had scheduled to check for that week. Unless something odd happened I would just have to sponge off Karen longer. The thought twisted in my guts like a knife.

She had been so kind, so supportive, helping me understand what I wanted as opposed to what I needed. I felt guilt piling up daily. How could I ever repay her?

It was then that I found the card again and seriously reconsidered teaching the class. I figured I had nothing to lose by and talking to them and meeting them.

A couple hours later I found myself down at the public shelter, the one that you could find by looking in the phonebook. It had things you might expect, offices, receptionist desk, I could hear a meeting going on in the conference room and there was paperwork just about everywhere. It looked about how I expected it to an underfunded necessity that had far too many cases and far too few people who could help with time, skills and resources for the people who needed help desperately.

I found the lady I was interviewing with and she invited me in. I sat carefully on the older chair and waited for the interview to start. Once the chair quit protesting my weight, I looked the woman over as carefully as I would a potential problem in the field.

She was small; almost bird like, bright eyes darting from my face to my clothes back to my face and then my resume. Her dark hair was going gray piled on top of her head in an untidy bun with wisps of hair curling around her face and neck. Her clothes were neat and conservative, nothing trendy or fashion forward. She scanned my resume carefully and began by saying,

“Mr. Taylor, I’m Jeanette. We don’t use last names here. That could get dangerous. I hope you can get use to being called Gregory?” She sounded like a miniature Katherine Hepburn.

“No m’am but Greg if you don’t mind? Please.” It was like being grilled by a sharp aunt who didn’t miss a thing. I felt a flush rising in my cheeks and couldn’t understand why I was blushing.

One eyebrow rose, “Breathe young man, I don’t think you’re guilty — yet.” The bark of the last work would have made any DI proud. I jumped as expected. Then I think I surprised her.

I smiled and nodded. “Some really good officers can make a noncom feel undressed in church m’am if you know what I mean.”

She seemed to relax at that and nodded in return. “Follow me, young man.” Without another word, she rose, walked around her desk and headed out the door. Her steps were light and her pace surprisingly quick.

We entered a gym. Her rubber soled shoes squeaked as she went toward a pile of mats stacked in a corner. Before I reached her she had wrestled one to the floor and was grabbing another mat. I hurried to help her. “Good.” If this was her normal mode I sure wouldn’t have to worry about having my ear talked off.

“Teach me.”

“Ma’am?”

“Teach me. I want to take your class.”

“Yes m’am. Self —defense is important. You should know why. You aren’t going to be Bruce Lee when you finish this course, but you will be better able to handle yourself incase something foolish tries to happen in your vicinity.”

On uptick of her eyebrow let me know that the last statement would have to be proven or removed.

I took a long slow breath. “Sit down.”

I scanned the room for a minute while she found her seat on a stack of mats. I turned back to her and said “Close your eyes.” She looked skeptical but finally she complied.

“Miss Jeanette, you’ve been in this room a lot, you know where everything is. Can you tell me what you can use to beat me off if I decided to attack you?”

She started a bit and her eyes fluttered. “Don’t open your eyes. I’m not going to do anything, but I want you to do this exercise without looking around.”

She thought for a minute or two. “Um, I think I could start with hitting you with the ball near the volleyball net. I could hit you with the barbells, and maybe trip you with the rack of basketballs?”

I heard the interrogative at the end of her sentence. I nodded and said, “That’s good for a start, but what’s wrong with your shoe?” She looked a bit surprised. “Open your eyes now; we’ll go through each and every thing you could use in such an event.”

Over the next half hour, I pointed out how everything in the room could be used in the case of an attack. She could pull the volleyball net down on me, pull the pole supporting the net down and hit me with that, she could hit me with her belt or she could pull the mat out from under me.

Once we went through all that, I looked her in the eye. “Being attacked is about survival, and 90% of survival is being aware of the area around you. Almost anything can be used as a weapon to defend yourself, more importantly to delay your attacker until you get out of the area. That’s the first lesson.”

“Greg, you’ve impressed me. If you want the job, I’d be glad to have you.” She looked impressed with me.

I bowed slightly from the waist. “Ma’am, my pocketbook thanks you.”

Sissy's Saga part 17

Author: 

  • Maid Joy

Audience Rating: 

  • General Audience (pg)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Transitioning

Character Age: 

  • Mature / Thirty+

TG Themes: 

  • Voluntary
  • Identity Crisis
  • Fresh Start
  • Real World

TG Elements: 

  • Appliances Attached

Permission: 

  • Posted by author(s)


Another Chance part 17


By Maid Joy

I thought I had it made. Teach a class in self-defense and that’s it. It was easy money and no worries no more feeling guilty no more sponging off of Karen.

Three weeks after I started work at the shelter, I knew I was close to losing my job. I had one person take the class, and while she loved it and was effusive in her praise, no one else seemed willing to try me out.

I pitched in around the center, filing and doing paperwork, putting my administrative skills to work for them, just so I felt I was earning my paycheck, but it wasn’t enough. I knew the axe would fall soon.

“Greg, can I see you in my office?” Jeanette said to me one day.

Here it comes I thought.

I followed her into her office and stood at something like attention in front of her desk. She looked at me. “Greg, we have a problem. Apparently because of who you are, the women here don’t feel comfortable. It’s not that you aren’t skilled, it is simply that the ladies who in the shelter, the ones who come here, are afraid of men. Even though your abilities are beyond reproach, the simple fact that you are male is scaring them away.

“It was a good experiment, but it looks like I’m going to have to let you go.”

I was somewhat relieved. “Miss Jeanette, is it just my sex that is putting people off, just the fact that I’m male, right?”

“Yes. I’ve needed a self defense teacher for some time, and I thought your skills would overcome the fear your sex brings, but apparently not.”

“Let me try something then, please? I think I have a solution to the problem, but I want to make sure that it’s a surprise to everyone.”

She looked at me over the top of her reading glasses. “Please don’t get a sex change just to keep this job.”

“No worries Ma’am. It’s not just to keep this job.”

Well, if you’re reading this story, you can probably figure out what I had in mind. I went home that night and spent considerable time getting “pretty”. I shaved everything, made sure my skin was smooth as it could be. I tried to do my nails and toes but I knew I didn’t look as nice as it should.

I had today off, so I decided to go to the spa. It had been a while.

I got dressed, did my hair up as I could, and put on my face. I pulled out one of my purses and put all my stuff in it. I also made sure I had my ATM card and that there was enough money in my account to cover the indulgence.

I won’t go into details of being pampered right now, but it was heaven. The ladies there made sure to take good care of me. They weren’t able to do much in the waxing department, and one lady suggested permanent hair removal. I thought it might be a good idea, so I checked in to the electrolysis service they had on the ‘menu’.

I would never think that makeovers and all the woman things to make her look beautiful were inexpensive again. I could see that I would have to save for a while to get some of the things on my list done.

In the end however, I was looking beautiful and smelling sweet. My eyebrows were nicely shaped and my ears were now pierced. All the things I wanted to do but couldn’t while I was in the Army. It was an incredible heady feeling.

I didn’t let them put on the killer claws they wanted to put on me. It would be hard for me to do three quarters of the combat and self-defense things I would need to without snapping one, so I settled for “sport length” which was just a little beyond my fingertips. Just enough to have nails, but not enough to get in the way.

When Mistress saw me, she was very excited.

“Sissy, I’ll be honest, I’ve wanted my girlfriend back. Glad to see you home again.” Then she kissed me on my cheek and went back to what she was doing.

I have to admit that I was relieved to be Sissy again, but I wonder how my name would go over among those women.

Nightgowns are wonderful things. They are silky, smooth, heaven on the skin and just all around gentleness. Men haven’t had anything like this since Queen Victoria’s times when men wore nightshirts.

Before going to bed that night, I made sure to glue the breasts on to my chest and check my clothes for the next day. I had a class to teach, and I wanted everything to be ready.

I laid out some shorts, a tank top, and the various under things that I needed. I picked a pretty pair of sandals and sport bra. I looked closely at what the ladies at the salon did to my face before taking it off, so I could duplicate it tomorrow.

Skirts would come later in the class. It was important to know how to fight in a tight skirt since a lot of attacks happened at clubs. Being able to beat someone senseless when you couldn’t get your knees more than 2 inches apart is not only a valuable skill it’s an art.

My dreams that night were intense. I normally saw myself as my he-self, Greg the Ranger, but this time I saw myself as Sissy only. I felt real breasts, and it felt so right and natural. The clothing I wore was normal, the skirt dancing around my knees and most strangely, I couldn’t feel a penis anymore. Not only did I get rather horny from that it was it was absolutely the right feeling to have. It was like stepping into a whole new me.

I woke with my hands stroking myself, not as a male would, but as a girl would. I was rubbing my belly, my chest, my legs, feeling incredible sensations as my hands brushed my body through the satin of the nightgown.

I got up and took a quick shower, making sure not to mess up my hair too much. I dried and powdered getting ready for the day.

It didn’t take me long to get to work. Traffic was with me and I was one of the first people there. I started organizing the files and paperwork, then I went into the gym to ensure everything was set up properly. I moved some boxes around and partially covered one door and then adjusted the blinds on the windows in the room.

Satisfied I went back to my job.

“Excuse me, but who are you?” I smiled up at Miss Jennette.

“I’m your self-defense instructor,” I said in my best Sissy voice. I held my hand out to her and shook it. “You hired me nearly a month ago.”

“GREG!” she nearly shrieked.

“Sissy, please, if you don’t mind.” I grinned at her. She spent the next five minutes looking me over and checking me out. Her appraisal became very detailed and I felt like I back in the ranks being inspected by the General.

Finally she was satisfied. “If I didn’t know better, I would swear you were born a girl,” she finally declared.

I smiled broadly and went back to what I was doing.

She thought for a bit and finally said, “Sissy, I don’t think that is going to be a good name for you.”

“It’s short for ‘sister’” I said.

“I understand that. But maybe Gina would be a bit more appropriate?”

I thought about that proposal. I could understand her point in that ‘sissy’ is a name that is used for derision. Sissy as a nickname wouldn’t be too bad, and Gina had a good sound to it. I nodded my head and accepted my new name. Gina Taylor. It fit.

The self defense class was pushed really hard that day, and with the announcement that there was a new teacher, a lady, suddenly there were about 10 ladies ready to learn.

When I arrived I found them waiting for me. I set my purse down near the rest of purses and stood in front of the ladies.

“Everyone, close your eyes.” I waited until they had. “How many exits are there from this room?”

I could see that they were confused. “I’m serious, protecting yourself is about survival, and survival is about being observant. If a man was in here and going to attack you, you would need to know where the exits are so that you can get out. So I’ll ask again, how many exits are there?”

Five ladies said there was one exit. Three said two exits. One didn’t know how many and didn’t answer. One lady said Five.

“Would it shock you all to know that there are five exits from this room?” The looked surprised and opened their eyes. I started pointing out exits.

“First is the door you came in through. Second is that door over there, a secondary exit, partially blocked by the boxes. The other three exits? Remember, you can go out a window almost as easily as you can a door; you might just get hurt a bit more.

“This class is about defending yourself against an attacker. It is not about honor, it is not about pretty, it is not about following rules. You will learn to use everything and anything as a weapon, and you will learn how to get yourself out of a situation with the least damage to you, and the most damage to him.”

From there, I started the class. It wasn’t anything shocking, just the same general fighting tactics that women are told, the emphasis this time was on hurting their opponent enough so he had no interest in getting up.

I had seen some pictures that made me angry to the core of my being. Women with bloody faces, broken arms bruise the size of dinner plates and dead women. All of my life all of my training taught me to regard women as sacrosanct, to be guarded, protected, and revered and the idea that some puke would dare to touch a woman made my blood boil. I kept seeing the faces of these ladies in harms way, and I was determined not to leave them vulnerable.

Throws and leverage escapes, I added an incapacitating strike in. Instead of just tossing the guy that grabbed them from behind, I had them add a stomp from their high heeled pump for good measure. The motto was “put him down and keep him there”.

I was enjoying myself and they seemed to have a good time too. When the littlest girl in that class threw me about four feet away, everyone cheered and clapped for her, none louder than me.

Perhaps this would keep them alive if they had someone come at them from a dark alley, or more likely from across the living room.

I taught the ladies every trick I had learned over the next seven weeks. We had class three times a week, and I showed them things they’d never though of. I taught them how to rupture a rapist’s testicle, how to kneecap a person, how to break strangleholds and chokeholds. I taught them not to worry damage they might do to some monster who didn’t give a shit about what he was doing to them, but to hit him as hard and as dirty as possible as fast as possible since it was highly likely that if a woman didn’t she would be beaten, used and then killed.

I made sure that the strikes I showed them would be “one hit” strikes, the monster was going down and not getting back up for a while. I knew if these bastards that some of them had were to attack, and these women resisted, the monsters would keep hitting them until they couldn’t get up again. I kept reminding them that the enemy was just that, not a person, not a human being. It was the enemy, a rabid animal, a bastard, monster something that had to be put down. It’s a standard tactic for training soldiers because it’s effective.

I tried to relate these things to food they had to handle. A testicle became a grape or plum. Squish it and it exploded. They had all squished a grape before and thought nothing of it. Gouging out someone’s eye or ripping someone’s tongue off with their teeth isn’t normal, so the food associations helped.

While I hoped to God that these ladies never had to use anything they learned. But I wanted to insure they were as prepared to react as instinctively as any one I had ever trained. They were my first new squad. I didn’t work them as hard physically as I would a military squad, but I certainly encouraged them to keep practicing in the evening and on weekends. The ones that did follow my suggestions definitely saw a difference in their stamina and physical fitness. As they got slimmer and healthier and able to eat more there were more ladies who joined the group and more who began to practice.

I wanted all the women in the shelter to feel confident about their ability to be safe from their abusers for the rest of their lives. I prayed daily that they would be safe for the rest of their lives.


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