The Collector: Sissy Academy Ch. 03

Chapter 3

I opened the PO Box as quickly as I could. Was it before I backed out or was I that desperate to experience losing control to this person?

Whatever the reason I didn't send the details until the end of the next day. The pros and cons playing through my mind.

Who was this person?

Could I trust them?

What was going to happen if I follow them? Will there be permanent changes or just surface adjustments like wearing makeup and underwear in private?

But then the cage stirred, thoughts of being pointed to the floor and expected to serve my Master. The hope of being dressed as a sexy girl with long hair and big tits, entertaining a group of men pointing their huge cocks as me.

I was daydreaming as I wrote out the message detailing the PO Box address. I noticed I had written it out without really, consciously doing it. I was having second thoughts; those doubts were coming back. I had enjoyed the ride, but after this it gets real. I will still be anonymous, but he will have invested time and money into me. That made it more real to me. I didn't want to waste this person's time.

Then the frustration took over, being locked for longer than I ever had before, my mind was struggling to deal with level of desperation I was feeling, I was starting to lose track more and more. My mind drifting into more and more titillating scenarios,

I closed my eyes, and I pictured being dressed in a figure-hugging French maid uniform. The tight corset accentuating my full chest and tightening my waist. I tried to move my arms to check if my breasts were real, but I was restricted with a pair of upper arm cuffs limiting my movements. I looked down and saw past my skirts to my ankle cuffs and locked four-inch heels. I was daintily running a feather duster it along a shelf in a well-appointed main room. A large open fire was the main feature of the room, it burned quietly as the centre piece beneath the shelf I was dusting. I was unable to explore more as I heard the door to the main entrance open.

I turned and curtseyed to my Master and his friend as they came in. Neither taking much notice of me. I turned back around as I heard Master tell his friend to take a seat and make himself comfortable. The door to the kitchen opened and Master began directing the kitchen staff as I felt movement behind me.

Suddenly I was bent over, I let out a little girly squeak of surprise as the plug that filling my ass was pulled out and put in front of my mouth. I opened without a thought and held the four-inch plug in my mouth. Tasting my ass on the solid silicone. I started to thank my user but was stopped as my ass was spanked hard, no doubt leaving a handprint on the skin, he positioned me so that my legs were spread as wide as my chains would allow, and my hands were held in the small of my back. I heard him spit into my still gaping hole. A gasp escaped my lips as I was immediately fully impaled by his long cock. It didn't feel as thick as the plug it has replaced, but it was a lot longer. He pulled my hair to gain more leverage as he pounded my hole. It hurt as he took no care for my comfort, and I felt my steel collar push against my throat. It was difficult not to drop my plug as he thrust over and over, pushing his dick into me, until after two minutes he held it there, fully embedded in me, I felt a slight twitch and a soft grunt as he deposited his seed in my bowels.

Without a word the plug was removed from my mouth and re seated in my ass. Holding the cum inside.

Once the plug was replaced, I turned and dropped to my knees and quickly cleaned my superior's dick. Not giving a blowjob, just using my mouth to clean his member. My lips cleaning every contour and vein and then my lips wiping any leftover moisture. After quickly cleaning it, I released it and gave it a tiny kiss to show I was finished. Without a word he joined my Master who had re-entered the room. Took his drink and they started talking. I went to pick up my dropped duster and was about to return to my duties when I was interrupted by the instruction that the Cook has cum in her ass that needed cleaning immediately as they were wearing a tunnel plug as a punishment. I was to remove the deposit and clean any mess. After completing that I was to return to the maid's station in the pantry and await inspection and instruction.

I started to shuffle in my cuffs, my ass sore from the fucking and the warm feeling of the cum giving me a full and uncomfortable feeling.

My cage ached as the fantasy ended, brought back to reality by the 'ping' of a received message. I was breathing so hard just imagining what life could be like that I has sent the message almost subconsciously.

Still able to follow instructions slut.

Good, your happiness is now dependent on mine.

As you have freely sent the PO Box details, I will take that as agreement to what happens next. There will be another two opportunities to turn back before you enter the Academy.

I have sent you a remote lock box for your keys. I will be in control of your keys from now on. You will be allowed a weekly hygiene opening. This will be monitored.

I have also sent a set of remote restraints for you to wear.

Attached to this message is monitoring software so I will know exactly what you are looking at, and if you are completing your tasks correctly.

Finally, and most importantly I have sent you a silicone training replica of my cock. This will be your focus from now on. You will treat it as if it were me. At least until you earn the honour of taking it for real. If you earn that right.

You now live under the following rules:

1. You will dress as I instruct while at home.

2. When outside the home you will ALWAYS be in at least panties

3. All underwear is to match

4. You will be sent a list of exercises to complete each day to help define your body.

5. You will practise for at least an hour with your mouth and ass.

6. You will be in bed by 10pm and awake by 6am unless instructed otherwise.

7. You will follow any and all instructions given without question.

These rules will be added to as we go. I will also be setting assignments to help determine what kind of sissy you will be trained and sold as.

Now say thank you and get to bed.

Master.

It took me five minutes to get my breath back and reply to Masters message.

This was it. Now it was real.

I installed the software and various sites were already banned. It was also clear that my keystrokes were being monitored. A message from Master came up, congratulating me on being a clever sissy for installing the program.

Tomorrow you are to take stock of what has happened and prepare for the next steps once my gifts arrive. Now its bedtime sissy. You are to sleep naked unless you have a matching bra and panty set you can wear to bed. We will sort your wardrobe out shortly.

Use the restroom and shower. You have 30 minutes.

You will install this program onto your phone as well so I can track your usage. The GPS will be disabled for now.

Now bed.

I thanked Him and got ready for bed, wearing my cage, which seemed to have shrunken to a large degree over the last hour. I got my matching black bra and panty set and put the software onto my phone.

It appeared to add several apps to the home screen which were locked currently. From appearances there was a calorie and exercise monitoring app, an app for playing video and audio and a list/task tracking program.

I read the messages again contemplating how my life was going to change, and honestly, I was excited. Nervous definitely, but my dreams were finally coming true. I barely recall going to the bathroom and getting ready for bed. I put on my pink bra and panty set, the cage visible though the light material. Wearing a bra almost felt natural, now I was expected to wear it. Would I have to wear it at all times? Would it be visible though my normal clothes? I had so many questions, but my time was running out. I got back to my bed room and tried to sleep. Luckily tomorrow was a day I was not expected into the office as I knew I was not going to get a lot of sleep and that my cage was not coming off any time soon.

I tried to sleep but thoughts and worries were running through my mind. What changes would Master make? What would he demand? Would I be able to carry on with my life as it was? I tried to reassure myself that he seemed reasonable and said there would be opportunities to change my mind. He was sending a lockbox that he controlled but until it arrived, and the keys went in, I could still just remove the software and unlock my cage. I had never asked him to send me that stuff. He had done it on his own. So, I don't even need to feel bad.

No, I thought, I still had a very real safety net under me and so I was free to allow it to continue until the timer on the lockbox ran out.

Despite my reservations I knew I wanted it to continue. The affect that it was having on my cage was evidence of that. My nipples were hard under the soft fabric of the bra, they had started becoming more sensitive since my cock had been locked away. I started to play with them a little but all it did was cause more straining in the cage.

I turned over in bed and tried to get to sleep. It was a little before 10pm when I finally managed to fall asleep.

I was awoken in the morning at 545am by an alarm I didn't set. The alarm stopped after a few seconds and an instruction was on the lock screen.

Shower and shave, I will be checking. Then we will go over your wardrobe. 20 minutes.

Any grogginess from sleep was shaken away as I read the message and the events of last night came flooding back and the cage strained even more the usual morning wood. I quickly got up and went to the bathroom, not only to complete my tasks but to use the toilet to reduce the pressure on my cage.

After finishing my shower and shaving what little stubble was around my cage I returned to my room and waited by the wardrobe for next instructions.

Another alarm sounded and another instruction was shown.

Turn on the camera and show your cage and genitals so they can be checked. If your ass isn't plugged, now is the time to correct that.

I turned on the camera and pointed it at my caged cock and I panned it around to show off my work with the razor and then behind to show the pink jewelled plug now seated in my ass.

The phone pinged a message and I went to read it.

We spent the morning going through my clothes one by one. Anything too 'manish' was put into a pile, I was allowed one veto for every five items I removed from my wardrobe. Light t shirts in single colours were left, some shorts and tighter trousers. I have always had a slender build so they look 'girly' with the right attitude.

After we emptied my wardrobe and draws of about sixty percent of their contents I was dismissed for lunch after being dressed in some tight jean shorts covering my panties and a tighter white t shirt that was chosen because you can see my bra through it. I felt cute with my little tits, boosted by the lifting of the bra making little mounds in the fabric. It felt a bit slutty to have my black bra showing. I wish my shorts were shorter and tighter, but it was a great start.

Over the course of preparing and eating my light lunch of salad with a little dressing I was given notifications from a couple of the new apps. I was nervous checking them out as I still didn't know what they really were. The first one was a list of clothes I was to obtain. I was to upload a picture of each, one with the item on a flat plain surface, the other with me wearing it and nothing else. There was a number of different items split into categories, from underwear to dresses to nightwear. A timer was in the corner counting down from a week. I clicked on the instructions tab and was met with guidelines I was to follow and expectations about what I was expected to get. I did sigh a little relief when I saw that buying online was acceptable at this point, but extra 'credit' would be given for any items I bought in person.

The second app was the video and audio app. I was presented with a listening and watching list. Some of the items were greyed out and were clearly part of a collection to be taken in order. The audio appeared to be mostly hypno files. They had dates next to them, when I was supposed to listen to them, I assumed.

The videos were a mixture of anal and oral training videos. They had no dates next to them. A couple were make up and dressing tutorials and a guide to measuring your vital statistics correctly and a couple of exercise tutorial videos. There were a final set of videos that were locked with what looked like a coin symbol next to them suggesting it would cost to unlock them. I was looking at the titles and feeling my cage getting tighter.

Sissy Maid Duties and Responsibilities.

Sissy Whore Destruction. Three on One

Sissy Blow Job competition. Vol 1

I was getting more and more excited when the app closed suddenly, and I was instructed to strip and present in my room in two minutes. Legs apart and hands behind head, my phone was to be placed close by where I could see the screen without moving.

I raced to my room and striped my clothes off and got into position. I placed my phone in front of me and waited. After about minutes the phone screen lit up and I was given more information about what my day-to-day routine would be like, what I was to do when I was expected to be in work and how the apps worked.

As I completed the tasks and training, I was to log it into the app. Some items would be time dependent, and others would log how many time and when I completed them. As I completed my training and consumed the content more would open.

As I finished the instructions they changed to a list and a timer was displayed in the corner.

It was counting down from eighteen hours.

The list was.

Oral Practise: 10minutes

Purchase two sets of underwear. (Use accepted List)

Purchase two complete outfits. (Underwear, shoes, top and bottoms from accepted list)

Anal Practise

Listen to first sissy audio.

Watch the measurement video and input measurements.

Watch two exercise videos and complete ten reps of each.

I was breathing heavily as I read through the list a couple of times. The app them closed and it was replaced by a single word:

Dismissed.

I took a number of breaths as I tied to come to terms with what was happening and how best to complete the tasks. The cage was struggling to contain my poor cock as it tried desperately to escape. I wanted to touch more than I have ever wanted before. I could see the precum leaking from the cage, it was painful how much I was straining in the tight confines of my cage. I was actually starting to struggle and needed to calm down.

I went to the bathroom and relieved myself, which immediately brought a little reduction and then took a cold shower. The water flowed down my body and helped me relax. I let the cold water flow into the cage to help cool me down and after about ten minutes I was feeling much better.

I went back to my phone a looked at the list again. I didn't want to do the anal or oral tasks as I had just cooled down. Although that didn't stop the cage twitching and my ass tightening over the plug as I though of fucking my holes.

I instead clicked on the measurement video and followed along as I took my measurements. I found that I had gotten my bra size about right and so entered them into a new app that had appeared. It seemed like a kind of diary app that tracked my training, exercises, food and water intake and a number of other sections that were hidden.

After inputting my measurements, recording that I currently needed a 32A bra, and a dress size 10 and shoe size 8. As I completed the task the app beeped, and it was removed from the list. I took a quick look at the time, and I still had over fifteen hours left so I decided to go back into the video menu to watch an exercise video and noticed that I had been given some of the 'currency' to open the locked videos. I had a quick look, to try and not get distracted by the titles, but I needed a lot more points to watch even one of them. I mentally noted the title 'A day in the life of a chastity maid' and the points needed to watch it.

I went to the exercise section and looked at the selection. I choose to start with simple ones as I was not in great shape and watched a video of a cute looking sissy, dressed in a tight black shorts and sports bra. Her tits looked a bit larger than mine, and the cage was visible under her shorts. I watched the tape of her doing the luge exercise several times to make sure I had it understood and repeated it out for a series of ten reps like the list demanded. I entered them into the 'diary' app and returned to watch a recording of how to complete some squats.

The same sissy was in this video but only in her bra this time. Her tiny metal cage bright in the studio lights. She smiled at the camera as she demonstrated how to perform the lunge. Again, I watched intently, this time my eyes were drawn to her tight ass. As the camera angle changed to a side view, I was saw I caught a glimpse of a metal plug as well. My cage was getting tight again as I got into position to complete my reps. After completing I dutifully entered them into the app and saw the task removed from the list.

It was getting later now, and I decided to take a short break for a drink and look through the video and audio apps more. I sat in the kitchen for over an hour drinking water and going into what was on these new training materials. I looked at the clothes again and saw how it could be sorted into different sections from cute to sexy to whore. While drinking I watched another video on how to create an ensemble with my clothing to give off a particular look or response. How colours and lines affect how the clothing looks.

As I finished my water and logged it into diary an alarm sounded. It was telling me I needed to remove my plug and demonstrate my ass gape and take a picture. I silenced the alarm and went into the bathroom. After getting into a position, I could more easily take a picture of my ass I removed the plug. I came out with a small pop and I quickly took the picture of the smallish hole my ass was making. I tried to use my ass muscles to keep it open but it quickly returned to its normal state. I was about to reseat the plug when an icon of a plug with a cross over it was displayed. It has a timer counting down from four hours under it. I assumed it meant that I was to leave my ass to recover for a time and went to add my gape picture to the app. My ass felt needy and empty but I guess its best to build up over time.

I looked at the time again and I had only just over twelve hours left. I sat at the computer and started to look at starting to order my new wardrobe. I looked at some of the items I had favourited while drinking my water and started to see if I could make some cute outfits with them. In the end I made a cute outfit of a light summer dress in green and yellow that went down to my knees with white ankle socks and black two-inch pumps. A pair of white panties and light green chamise top for under the dress.

The second out fit I went full slut.

A red half cup bra with a fishnet halter top, that would only just protect my modesty. A tight leather mini skirt that would barely cover my ass matched with red thigh high boots, with four-inch heels. A tight black choker finished it off. I hoped I wouldn't be punished for not including panties.

I ordered them from a well-known order company and submitted the images from the site to fulfil the instructions before they could be logged properly on the clothing app. I then looked at the underwear. I went for a red corset with a matching red thong. For the second I chose a cute pink camisole. I logged these and looked at the time.