Sissy Captured -- Pt 9

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.

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