I am a card-carrying member of the Secret International Society of Sissified Youth (SISSY) Order. Well it’s not really a card but, more of a ring. This is my story of how I became member. I’ve been with the Order for 10 years of service, 8 of which were great. I’m not sure if I’ll make it to retirement but this is my story of how it all began.
It all started really when I was 11 and began dressing in my Mother’s clothes. I didn’t know what it was at the time but, being in women’s clothes just felt right. That might have been due to be molested by a neighbor during that time period but, I don’t look at that in a negative light. I believe he was just helping me find the way to my true self. Who knows, maybe I was asking for it, god knows I would do it all over again the same way if given the chance.
At the age of 14 I was given a new computer by the neighbor, probably as a hush bribe before he moved away. Somehow this didn’t set off any alarm bells with my Mother. She was a single working woman who had a lot of things on her plate at the time. The age of the household internet was just kicking off and I convinced my Mother to purchase internet access in 1996. At first, I didn’t know what to do with it but after talking with some friends at school, I learned about chatrooms. It seemed amazing to be able to talk to anyone anywhere in the world with just a few clicks of a mouse.
It didn’t take long for me to find like minded people in the ICQ and AOL chat rooms. I learned what cybersex was and chatted with a lot of other boys my age and men. Once they learned how much I enjoyed dressing like a girl and how I was molested, it was like moths to a flame. I would spend hours talking to what had to be thousands of people. In 1998 at the ripe age of 16, I received my first webcam. One of my friends online sent it to me through the mail. I hooked it up and the world was my oyster.
My Mother worked a lot which left me home alone to dress and chat online. I could easily have 6 to 8 hours alone. I remember more than a few nights, hearing her car pull up, realizing it was 2am and running to bed before she caught me. During these long chat webcam chat sessions, I got to know quite a few people fairly well. Friendship and long-distance relationships were built. I would log on and be greeted like a princess. This is when was introduced to a possibility of living life as a full-time girl. Some of these men would be willing to pay me to be their permanent girl for as long as I wanted. The idea intrigued me to say the least.
I knew this could be a dark road I would be heading down. I had heard the stories of girls meeting men online and being raped, kidnapped and sometimes killed. While the idea of being kidnapped and raped was somewhat appealing me while in the fantasy land of the internet, in real life, I was not sure about it. Being at someone else’s mercy was a popular roleplaying fixture in many of my chats, it opened my eyes to just how dark some of these men really were.
One of my more trusted friends online, David, who was 42 years old. He invited me to a special party. He explained it as a world were people like him and I could meet others in person and I had the possibility of living as a girl. I thought he was just making things up during one of our video sessions. He offered to buy me a plane ticket and he would escort me to the week-long party. David would spend hours explaining to me how it worked. I could enter a yearlong contract with a Master or Mistress and live as a girl. I would be paid $66K into a bank account set up in my name. I wouldn’t and couldn’t spend a dime of it until the contract was up though. If I wanted, I could do this for 12 years and receive a bonus at the end.
David said that if I was a sissy for 12 years, I would be set for life with money. I would receive a million dollars and live off the interest for the rest of my life. It wasn’t easy though. Each contract is agreed on by the sissy and Master/Mistress. Almost every detail is spelled out and if it’s broken, the deal of off for whomever broke the contract. He admitted some of the very dark and some dangerous people are there. There would be someone to help me find a good Master/Mistress until I learned the ropes.
My Mother and I were not getting along very well at the time. In hindsight, it was probably my fault. Spending hours on the internet talking to seedy men and then being thrown back into a reality that I was only a 16 year old boy was hell. I finally agreed to accept David’s proposal, he said I needed to wait until right before the party though. I ran away from home in 1999. I was 17 years old, 5’8’’ with longish brown hair, blue eyes and only weighed about 115lbs. I flew from a small town in the southern US to New York City. It was there, David picked me up and greeted me with a great big hug.
David took me shopping and bought me a few outfits for the week-long party. He said I would need a little bit of everything. It was kind of a pageant, where I would be trying to attract the best Masters and Mistresses. I would need some formal wear, swim wear, lingerie, casual, and lots of pretty panties and shoes. He explained a few more things about this party is held twice a year and people from all around the world come. If I so choose, I could live in almost any country although he would advise against a few. We then headed to the salon and spa where my hair was given a more feminine look and my eyebrows waxed. I was then taken in the back and given a full body wax, where all my hair below the neck was removed. David knew most of the women in there. I they knew what party I was attending, they treated me very kindly and told me have fun.
David told me the part would start on Friday and end on the following Friday with contracts being signed on Saturday. Some of the Masters/Mistress had lives with spouses and children that may or may not know about this secret. He explained, I would be a Nanny, maid, or house guest as a cover. It was only Tuesday now. David gave me a hotel key and a credit card with $500 on it. I was to stay alone in the hotel and prepare myself for the party. He would pick me up on Friday for a manicure and pedicure before the party started at 6pm. The credit card was for anything I felt I needed: food, more clothes, toys, or whatever.
It was my first time being in a hotel room completely alone. I tried on all my clothes and found the best combination. I must have masturbated 50 times, seeing myself looking so feminine in the mirror really got my blood pumping. I then remembered David said I needed to prepare myself, I wasn’t sure what that meant at the time but, it dawned on me that I may need some lube and toys. I went and purchased what I though I would need to properly prepare. After a few more masturbation sessions with the toys, I felt ready for almost anything.
Friday was finally arrived. David called the hotel to ensure I was ready and took me to get my nails done. He explained then the first night was a formal meet and greet where I would be introduced to the SISSY Order. Orientation would last about 2 hours and dinner would be served afterwards. During dinner, I would be seated randomly with several Masters/Mistresses and another sissy at the table. Normally the sissy at the table with me would be my assigned mentor. I asked him where he would be and he said his journey would end with me once I stepped inside. This saddened me, he went on to say he was an agent for the SISSY Order. I wasn’t quite sure what that meant at the time.
David took me back to the hotel to get ready for the formal night and assisted with packing and carrying my newly acquired bags. He gave me a few tips on makeup that turned out great. We left and drove out of the city. We arrived in the suburbs at a huge house. The kind you see in the movies with 20 bedrooms, 10 bathrooms, and leaves you wondering what one does with all that space. As we drive up the mansion only seems to get bigger. We arrive and a man opens the door for me, while another grabed my bags from the trunk. David greets the men and informs them, I’m new while giving me a kiss goodbye.
The two men escort me into the house as David drives away. One man takes off with my bags upstairs while the other introduces me to Master Ben, the host. Master Ben takes my hand and softly kisses it. He had a deep hollow voice I’ll never forget. He tells me not the worry and all the other girls are in the conference room, he tells me he’ll see me soon and walks away. The escort then ushers me into a room that is set up like a board room, all sitting around a large rectangular table with a projector at one end. All the girls quite talking as soon as I walked in but quickly resumed when the door closed behind me. I found my way an open seat and listened to buzzing conversations.
Apparently, everyone has the same information I had and didn’t know what exactly to expect. A few of them still look more like a boy then a girl but, we all were well dressed and dolled up. One of the girls leans over and asks my name but before I could respond the large wooden door opened and in walked the most elegant looking woman I’ve ever seen. She greeted us and informed us she was a SISSY, although retired. It was her duty to orientate us to the Secret International Society of Sissified Youth (SISSY) Order. If we wished to leave, we should do so at this time. She told us to call her Ms. Ashely and handed out pamphlets we were to read tonight on the details of consequences and retirement plan. She then showed a short video clip on the projector.
The Secret International Society of Sissified Youth (SISSY) Order was founded in 1933 by a group of young men that could not support themselves during the great depression. Work, especially decent paying work was very scarce. While the Order started out with only 2 sissies that were essentially prostitutes for wealthy men. The Order grew larger during WWI and WWII as some draft dodgers found being it more appealing to be a SISSY than a solider. Today, there are over 3,000 SISSY members around the world. Master and Mistresses, M&Ms for short, are at the greatest numbers ever. Ms. Ashley went on to explain that the M&Ms pay a monthly subscription fee for being apart of the Order. Those fees are what pay our salaries and benefits. We will receive $66K for each year long contract we complete and at the completion of 12 years of service, a million-dollar bonus will be granted and we have the option to retire. She goes on the say that doing 12 years is extremely difficult and we cannot fathom the undertaking it was for her.
Ms. Ashley showed another video of hard core amateur porn, staring a SISSY. She goes on to describe this was part of the SISSY’s contract. The girl the video is crying and screaming while lying face down on a small table. The man keeps beating her with a whip, fucks her in the ass and then skull-fucks her while she’s tied up. The room is filled with sounds of rape, whipping and gagging. Ms. Ashley stops the video to explain that this girl was her. It was in her contract to allow the Master to do this once a month. While not all contracts are the same, it’s standard practice that your M&M will push your boundaries further then you would like. She continues the video while all the girls in the room look around in horror. Once the video was over, you could hear a pin drop in the room.
We are put on break and allowed to talk among ourselves for a few minutes while Ms. Ashely did a few things. All the girls cannot stop talking about how brutal that Master was and how they would never let him do that to them. One of the girls spoke up and said that’s why we get paid at the end. A million dollars is a lot of money and she would do it. A few heads nod and I caught Ms. Ashely listening to use while smiling and nodding as she putting items on a tray. It turned out the items were chastity cages and a small cup of ice. The cages were really fancy, gold with gems and jewels attached. I had heard of chastity cages but, never worn or even seen one in person. Ms. Ashley had us all line up and one by one to sign the SISSY Order pledge. While reading the pledge aloud we had to lift our formal dresses up while she pulled our panties down and determined the right size cage. I wasn’t sure what the cup of ice was for until she scolded one of the girls and put ice on their dick to make it fit in the cage. Ms. Ashely said the cages were required and can only be removed by a M&Ms. She went on the say that some M&Ms do like boyclits and some do not. This is to ensure we are all comfortable in chastity and abstain from masturbating or fooling around tonight.
We were then released and shown to our rooms. All of us girls had rooms next to each other upstairs on the 3rd floor. I saw more people in the house at his time, it seems the party had started. We were told to get ready for dinner in 10 minutes. It was a formal event and we should look our best for first impressions. I used the bathroom and quickly realized I should sit like a lady while the cage is on, after my piss went everywhere. When touching up my makeup, I started to get a little excited down there and figured out that cage wasn’t painful but, didn’t feel the greatest either. This somehow excited me even more which continued the cycle of unpleasant pressure. I’d have push all those dirty thoughts deep down and concentrate at the task at hand, fixing my hair and makeup.
There was a knock on the door and all the girls were escorted down stairs and brought into this large open room. There had to be over a hundred people inside and out. There was a stage where a few people were playing classical music. I was handed a glass of champagne and as soon as I took a sip, I realized I hadn’t eaten since this morning and I was starving, even with my nerves a wreck. Master Ben took the stage and introduced himself to the group. He then asked for all the new girls to come to the stage. Ms. Ashely met us on stage and started introducing us, having us walk on stage. We all smiled and looked over the crowd of men and a few women and sissies. You could tell the Mistresses from the sissies because all the sissies wore colorful dresses where as the M&Ms wore black and white formal wear.
As we left the stage, our mentor greeted us. My mentor was Sissy Kate and this was her 6th year. She told me not to worry and to enjoy the party. After a few minutes everyone was told to make their way to the dinner hall. Kate showed me the way to our table. As we approached, two white and a black man along with a white woman waited for us to be seated at a round white linen clothed table. We quickly introduced ourselves. It quickly became apparent these were M&Ms grading me against Kate. Sissy Kate spoke with confidence and was very polite. Kate did most of the talking though.
All though dinner, the M&Ms spoke to Kate and I on several different topics from religious believes to personal experiences. They were quite curious how long I had in this lifestyle and if I’d even taken a lover before. I explained my past relationship with my neighbor and one of the men said that tends to be apart of a lot of the girl’s past. Kate nods while sipping her champagne. A small dessert was served after diner and then all the guests were asked to head to another room, one for sissies and the other for M&Ms. Kate accompanied me to the other room with the new sissies and their mentors. We all chatted about our dinner and broke away for more private mentor session where Kate explained the whole process.
All new SISSY members go through training and a grading process. The higher the grade, the more control I have went negotiating a contract. Kate said I should receive a high grade because I’m young, pretty, and small. She looks around the room and points out the few girls that look like ugly boys; “They are going to have it rough because no one wants an ugly sissy”. I’m happy that I will do well but Kate goes on to tell me I will be tested during training. “Do not give into your male urges, they will only get you hurt”. This started to worry me since I’ve always had a problem with impulse control. I think it’s the reason I’ve always masturbated so much. We talk some more about how many SISSY members actually make it the 12 years. She told me only a few because how the contract starts to get more difficult when we get older. I asked how long I have to wear the chastity cage and she responds with, the whole week. I gasp a bit, I’ve never gone more then a day or two without masturbating. Kate tells me I’ll get use to it.
After a while, we are invited back the dinner hall but all the tables have been removed. The M&Ms greet us and ask us to dance. I’ve never really danced before and never in heels or dressed like this. Kate gives a reassuring smile and tells me it will be fun, they’ll take it easy on us as she is led to the dance floor by a Master. I’m taken by the hand and led to the dance floor. I danced with about 7 or 8 different M&Ms. The Mistress I danced with was very stern and rigid, she treated me more like a child then a lady like the others. I thought it would be more fun to serve a woman before but now, I started thinking the men might actually treat me better.
At the end of the night, we were told to head to our rooms. It will be an early morning followed by more festive actives each evening. All the M&Ms watched the new girls leave and our mentors stayed behind. We all headed up stairs giggling and excited about the new life we’ve just begun. It was hard to fall asleep with cage on and I woke up a few times to throbbing pain. Those midnight hard-ons were kicking in strong but the cage was starting to hurt from the pressure. The next morning came slowly through the night. I remember the knock at the door, Kate walked in with tray. This time I recognized what was on the tray. Anal plugs ranging in 6 sizes and lube, she told me to use the bathroom now or I’d be holding it for a while. I tried but only peed. I was supposed to use the largest plug I can. Kate explained it’s better to start as big as you can because by the end of the week you’ll be wearing the large one, waving it around. Each plug was shiny metal with a different color jewel at the end.
I pick out the 3rd plug, which I felt somewhat comfortable with and then Kate grabbed the next size up. She said that I would thank her later. She let me try to work it in on my own but, after a few failed attempted, gave some assistance. It filled me and sealed me up. I could feel the weight and pressure of both my cage and plug with every step. Kate told me to get dressed casually, skirt and blouse for breakfast and training.
After breakfast the training session started. Ms. Ashely asked us how we slept and explain the night will get better as learn to live in our chastity cages. We were all given paper tests with multiple choice questions on it. We were told there were no wrong answers but, were had to answer all the questions. These questions ranged from sexual things we’ve done in the past to things we are open to try. Some of the questions were about scat and pain or doing general house work. I’m sure it was to build a profile for each of us to present to the M&Ms. We were told to answer as honestly as we felt like.
During the test I noticed I started rocking back and forth on my plug. The sensation was great, I looked around and a few of the girls were doing it as well. I tried to hide it but Ms. Ashely look directly at me and told us all to sit still or we will be punished. I pressed my legs together and did my best to concentrate on the test. At the end, we were told write the Master or Mistress name on the back of the test we liked the best from last night. I’ve always been terrible with names, the only name I could remember was Master Ben. I didn’t even talk to him more then just the initial greeting. I wrote is name.
Ms. Ashely collected the tests and played a video of a sissy trying to masturbate with a chastity cage. The sissy was trying hard but just couldn’t seem to get herself off. When the video stopped, Ms. Ashely explained that the cages were special order. Each time you try to masturbate it will only make it hurt more. The only way to climax with them on is through prostate stimulation. The video goes on to show how to simulate our prostate with a dildo. When the video ends, Ms. Ashely tells us all we are prohibited from simulating our prostate while in training. After a few grumbles, she explained the reason why we show the video on day one. We are being monitored at all times. If we are unable to refrain from masturbating now; when we enter our contracts, our chastity may be for even longer periods of time which will be much harder. If we masturbate, there would be consequences.
We all agree this is still what we want to do and press on. One of the girls looks like she is about to pass out, she is sweating and holding her stomach. Ms. Ashley told us that our body will get use to the plugs and our bodily functions will adapt over time. When we were finally released for lunch a few girls tried to run upstairs to the bathroom but suddenly stop to gently give their plugs a push back in. As I walked up to the 3rd floor, I felt the same pressure and nearly lost my plug and everything behind it.
Once lunch was over, we moved to a room with hard tile floor. We were instructed to get on our hands and knees and stay there until told otherwise. The mentors would be checking on us to ensure we listened. We were a little confused but all followed the instructions. While the hard floor on our knees wasn’t bad at the start, it seemed to quickly become a torque device. With my small boney frame, my knees were aching. After a few minutes a mentor came around to each one of us, lifting our skirts and pulled down our panties part way. This exposed our plug. It must have been a site to see 10 girls on their hands and knees with their ass exposed. A few M&Ms soon walked in, inspecting us all. They walked around complimenting our body and even praised the one girl with the biggest plug in. They left and another mentor came in and told us to get on our knees and elbows. This was excoriating as my elbows were even bonier then my knees. After a few more minutes some of the girls couldn’t take it any more and got up.
When the next mentor came in, she told the girls standing they could leave and left the rest of us in torment. We started talking about what could be worse, this or whatever punishment they dish out. A few more girls stand up. I knew this was a test of obedience and wanted to do well. When another mentor came in and told the few of us left, we needed to put our noses on the ground and put our arms behind our back. A larger group of M&Ms entered the room and praised us all on our form. Before leaving I could feel one of them pull on my plug a little and whispered that he like was he saw. I recognized that voice, it was Master Ben. Soon after they left we were told to get up and start getting ready for the pool party.
It was early summer in New York, it was a little cooler then what I was use to but not cold. I put on my swimsuit but quickly learned there would be no way to hide my cage in my two piece suit. I had a small enough penis that could easily tuck but, the cage was too bulky. We tried to get a different suit but, Ms. Ashely said we had to wear what we bought. Some of the girls were completely embarrassed. I tried to cheer them up but, several of the M&Ms were pointing and making jokes at our expense. The M&Ms wore robes while we sissies had to wear our swim suits. Each girl had to walk around the pool before they were allowed in. I have to say, that cool air made the plug run further up me then before. Especially when we were told to exit the pool while dripping wet randomly for closer inspection. We then had our fill of oeuvres before be sent to our room for the night.
I did find out what our mentors and the M&Ms did after we left every night. We were instructed to remove the plug before bed, to give our hole a chance to tighten back up. The next day was much of the same. A class on etiquette followed by a different type of obedience training. This one involved deepthroating a dildo. We had to learn to breathe with our mouths full. Measurements were taken how thick of a dildo we used along with how deep we could go. We were told not to worry about gagging, some of the M&Ms prefer it.
I didn’t learn until later that the girls’ punishment for falling out of obedience training was having to sleep on the floor tied up after their beds were removed. When the same girl failed two days in a row, they made her sleep on the floor in a kneeling position with a gag in. We all quickly learned the hour of torture was better then all night in discomfort.
On the another days, we learned different fitness exercises to improve our feminine form, the proper diet with hormones, and proper oral sex technique on men and women. I wasn’t aware at the time every woman is different and what works on for one probably won’t work on another. Ms. Ashely gave us stories of the 2 she served in her years. The mistresses were constantly humiliating her because they felt she was prettier and sexual relief was few and far between. The more I learned the more I realized serving a Mistress would be much more different and difficult.
The next few days went by quickly. Staying busy and learning the ways of the SISSY Order was becoming enjoyable. On the final day, before the ceremony, Ms Ashely asked if any of us had masturbated. We all shook our head no, but then she said coming clean now will be better. She looked around the room and Sissy Kim put her head down while raising her hand. Ms Ashely had her come up in front of us all and strip down to her underwear. She took out some bright red lipstick and started writing on her stomach, chest, thighs and back. We couldn’t read it at first then it was clear. Slut, Whore, Use Me, and Cum bucket were written. Sissy Kim was allowed to put her clothes back on but was warned to not erase what was written.
In preparation for the ceremony we were given enemas and told to wear lingerie with heels, only. This was our final graded area. We will be signing contracts in the morning. Although that night, we may receive sexual relief or even temporary release from chastity if our M&Ms granted it. By this point we are all sex crazed from being locked up and plugged. I could feel my boyclit, as we are to refer to it now, dripping already. I was longing for someone to touch me. I went upstairs and changed into my lacy black nylon lingerie. It came with stockings and a red bow on the back of black satin panties.
The knock came to the door and I felt and looked great. I walked with pride and confidence, ready for whatever was ahead. I have to say all the girls looked great. Even the couple that originally looked like ugly boys were glowing in femininity now. During the week we were on a strict diet many of us lost weight but gained budding breasts. I could feel the pressure in my cage almost constantly now. As we walked down stairs, we could see the shiny purple jewel in each girl’s rear in front of us. The lingerie left little to the imagination. The weight of the largest plug was sensational to me. I felt I might explode at any time.
Once we arrived in the dinner hall, there were 10 tables for each of us kneel on. We were put on display on our hands and knees with blind folds on as the M&Ms walked around inspecting us. This was the first time we were allowed to be touched, M&Ms ran their hands over our body and gave tugs on our cages and plugs. It was an incredible feeling. I heard commotion from one of the tables, the girl’s plug came out with little force the Master said. Being so loose would cause her value to be degraded. I couldn’t image what shame and embarrassment that girl was feeling at the time.
I could hear at another table, it must have been the Sissy Kim’s table. Everyone was reading off what was written on her. Ms. Ashely was asking Sissy Kim what she had done to deserve this humiliation and Sissy Kim was made to repeatedly say out loud she tried to masturbate for what felt like an hour.
I waiting in anticipation for the next hand to grace my body; I was constantly on alert. Finally, I could hear Master Ben’s voice addressing the crowd. He told the M&Ms to flip the cards over in front of the SISSY and whoever’s name is on it has first command. I heard someone read off Master Ben’s name in front of me. I can only assume it was chosen from the test the first day. A Mistress yelled at Master Ben, informing him he was on my card. I heard distinct footstep getting closer. I could also hear what sounded like briefcases being put on each table and opened.
Master Ben whispered in my ear as he ran his hands over my body, “I’m happy picked me, I’ll be gentle and good to you.” The room was buzzing but, I sensed a large metal bowl being placed under me. I could feel my panties being slid down slowly as he firmly gripped my plug. I half expected to hear a pop and be shot across the room when it came out. I’m sure I let out a moan because I could hear other girls moan as theirs were removed. Master Ben apparently showed everyone the plug and how clean it was. I could hear some mumbling that seemed positive.
My hole must have been spasming. Once the plug was out, I had an uncontrollable desire for it to be filled again. I started to get nervous as I heard a bottle open and be squirted on something, then shockingly felt the cold lube on my ass. Master Ben said, “Sorry, I should have warmed that first, I’m going to fuck you with a dildo now until you cum. Don’t worry it’s smaller then your plug, just stay still and enjoy it.” His commanding voice was very soothing. Even though I knew a lot people were watching, I felt like he and I were alone. He slowly starting sliding the dildo in and then I heard more mumbling in the background. Something about how I was leaking already. Master Ben pushed and pulled the dildo slowly going deeper until it felt like it hit my stomach.
I suddenly heard one of the girls scream out in pain. She was being whipped in front of everyone. After a few minutes she was gagged but, we could still hear her painful moans echo after each lash. Other girls were moaning in pleasure and some in pain. I pushed all the noise and commotion out of my head and concentrated on the sensation of the dildo slowly and methodically fucking me. The next few minutes felt like forever but, an orgasm was building. First my knees and legs started to shake, next I felt the great pressure in my boyclit be released. The rest of my body soon followed in convulsions and tingling feelings. I felt like I was about to pass out. I started to clapping around me as my other senses came back to me. The dildo and blindfold were removed. The bright lights hurt but suddenly I remembered I was being watched. All these people just saw me orgasm and are clapping.
I looked down to see where my cum had ended up. I was still flowing cum from my cage and it was going in the metal bowl below me. Master Ben again whispered in my ear, “You were perfect, you are now an officially a SISSY. Wait here for further instructions.” I watched as he walked away, checking out the other girls. My mind abruptly remembered what Master Ben announced of first to command. I wondered how many M&Ms would control me tonight. Then I remembered about the girls screaming and moaning, I rapidly scanned the room to see a Mistress still whipping Sissy Kim. Kim’s face was red with tears flowing down it. I scan the room more to see a Master using a rather large dildo on Sissy Rita, judging by the location and distance, it was her plug that was loose. Rita’s face is a mixture of pain and pleasure. It seems all the rest of the girls have cum, as we all watch in horror of the action and euphoria from our orgasm.
Some of the M&Ms suggest the Sissy Rita’s dildo is too large to allow her to cum. Another group suggest the Mistress whipping Sissy Kim that enough punishment has been given. Judging by the conversation I could hear; the whipping Mistress has a tendency to get carried away. Sissy Kim’s cage was then removed by the Mistress and her boyclit was quickly being yanked on. It took a few minutes for her boyclit to stiffen up but, she was soon being milked into the bowl. It was about this time I heard Sissy Rita let out this ungodly moan as she too began to orgasm. The Master behind Rita expressed his thought rather loudly and somewhat out of breath about the dildo being just the right fucking size.
Master Ben and Ms. Ashely took the stage. Ms. Ashely asked for the bowels to be collected and poured into one, then poured into equal amount in the 10 glasses. Our mentors took to our side, lubing up our plugs and inserting them into us. They collected the bowels as we were instructed to step down from the tables and come on stage. Once on stage our mentors brought us the glasses almost filled with cum. Apparently, withholding from masturbating has caused quite a lot of cum to build up in us. We were told to recite the SISSY Oath and drink the glass while everyone watched. Afterwards we were escorted to our rooms and told to pack, after contacts were signed we were to leave.
I remember I had one of the best night’s sleep of my life. The morning came and after breakfast we were meeting in the dinner hall. Each table had our name on it with several pieces of paper. Some tables had more papers then others. This was the contract offering portion where some girls had more offers then others. There were a lot more SISSY girls here now. I guess this was when all SISSY contracts were organized from. The new SISSY girls were instructed to read over each contract carefully with our mentor. Make changes to what sections we deem and they will be submitted and revised until the pertaining M&M and SISSY member are in agreement.
In remember reading that if the M&M broke their contract, they would be required to work as an Agent until they gather 10 sissies for orientation and/or be thrown out of the Order. If a SISSY broke the contract, it would go on their record and no payment would be received. Conditioned in the contract ranged from punishments for failing to follow certain rules to frequency of certain sexual and non-sexual acts. Most of the contracts required the SISSY to be in chastity for a certain number of consecutive days before release. At the end of the contract, I would be returned to the Order for reassignment.
Sissy Kate helped me pick out the best contracts to make changes to and resubmit. She explained as the years add against us, it starts to get difficult to get a decent at her mark, 6 years in. She took her current contract with the Order in hopes to attach better future ones. Currently, she mentors and entertains the M&Ms at night. She went on to show some marks on her legs, explaining that the further you get the rough the M&Ms get. Luckily she only had to work for 2 weeks while the Order meets. There weren’t always a lot of choices for a SISSY nearing retirement to receive the bonus.
About an hour after we sent our contracts out for adjustments, the M&Ms came in with new contracts in hand and sat at our table. They watched as we read over them again and a few girls made more changes. I was happy with mine and signed with Master Treyvon. A tall 6’1 or so black man. He seemed delighted to have me. Kate had told me the black men offer some of the best contract conditions for a new SISSY. This is because they want you as arm candy, young white sissies are a premium in their social circles.
I signed and was soon in a car learning all about Master Treyvon’s likes and dislikes. He treated me very well I was sorry to see our time come to an end a year later. I still received a good number of contract offers for the next few years. All the M&Ms talk to each other, doing well with one can improve your demand. It wasn’t until I went into my 8th year did I start to regret my choices. That’s another story though. The Secret International Society of Sissified Youth (SISSY) Order will likely have me excommunicated for writing about my experiences. They pride themselves on being secluded from the mainstream. I might find more happiness being released from the Order then in suffering 2 more years until retirement.
Source: reddit.com/r/eroticliterature/comments/7q2f4y/the_secret_international_society_of_sissified