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.

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.