Rachael's Training Journal 2008

ENTRY 1

Another year has begun for me in my life as Ms. Robin's sissy maid. Some huge things happened in December though. First, ms. Robin now has her daughter joining her sessions and I am used for practice as Ms. Robin trains her daughter in her special ways of female domination. It is so humiliating to have to reveal my sissy clit to Ms. Robin's daughter, Miss Marie. One of the first times that I had to do it was when Ms. Robin demonstrated how I was milked electronically with my chastity device left in place. Then there was the time that she was training her on spanking techniques and they spent a couple of hours practicing on my ass. I was sore for days after that.
 
For Christmas Ms. Robin locked on my new chastity belt (pictures should be posted when this is put up). It is from the same place as the last one (www.robospanker.com) except it is the deluxe one. It is totally emasculating for me to always have my sissy clit resting in a tube and to have my whole genital area covered by a steel cup. It is especially weird when I am taking a shower as I never feel water hit that area anymore. My weight has become an issue again and the new belt locks on quite tightly in the last possible hole in the belt (there are 3 holes available for adjusting the size of the waist belt). Ms. Robin has told me that by next Christmas she wants me to be on the tightest hole and she would like to have to buy me a new belt at that time so we can start the process all over again. Ms. Robin is developing a weight loss plan for me. I am sure it will cause me many miserable meals but that is part of the life of a sissy maid.
 
Ms. Robin has also looked at some 6-inch heels that she wants for my heel training. It has gotten to the point to where I can't bear to be out of heels for any length of time as it is just to painful. So I find myself slipping on heels just to go to the restroom in the middle of the night. Of course I have to sit down to pee and I have to feel the pee force its way out the tube that my sissy clit rests in inside the cup of the chastity belt itself. And of course there is no way for me to shake off any little remaining drips so I have to make sure that I wipe the end of the tube and then also make sure that the end of the tube will be resting on the feminine pad that I always have in my panties that are pulled up over the belt.
 
I will try to write again soon about my training and experiences. I hope you enjoy the photos of my new chastity belt and also the videos of one of my monthly electronic milkings. Bye for now!
 

ENTRY 2

Hard to believe that it is already February. Miss Marie joining Ms. Robin has had quite an impact on my life. Having to serve these two beautiful dominant women while remaining in chastity and being routinely punished is proving to be quite a difficult adjustment. Ms. Robin has had Miss Marie basically take over my weekly punishments so that she can get additional practice in on her whipping and caning skills. Miss Marie has no real deep emotional attachment to me like Ms. Robin does so when she punishes me she never holds back and is constantly trying to make the punishments as painful as possible.

An even worse humiliation is when Miss Marie does my monthly milking. It feels so much more humiliating to hear Miss Marie talk about how nice it is that Ms. Robin keeps my tiny sissy clit locked up or even worse is when Ms. Robin is supervising the milking and the two of them talk about the milking process and why I am kept in chastity and how all men with small endowments like me should be kept in chastity and how punishments are so much more painful if they are done after a milking is concluded.

Their conversation is most often done in a way like I am not even in the room. Except then one of them will say something like: "Do you see how he twitches in pain when I turn the knob like this?" or "I got it all the way up to 10 in under ten seconds and that muffled groan of pain through the gag is just music to my ears."

My housework load is also increasing because I have to go clean Miss Marie's apartment as well as keeping up with all of my household duties in Ms. Robin's home. Some days I work up to 18 hours and get spanked unmercifully at the end of the day anyway because all that was expected of me was not completed to each of the ladies satisfaction.

Then I am sent off to change into the heavy cotton nightgown that I sleep in and sent to the basement to sleep on the cot that serves as my bed. I always have to spend my few short hours sleeping with the monitor sitting next to my ear so if Ms. Robin needs me during the night she can just call me or even worse are the nights when she has a lover over and I have to listen to the passionate sounds of their lovemaking through the night while my tiny sissy clit suffers in my chastity belt. But through it all I love that Ms. Robin has given me the life that I wanted which is to serve her always as her most humble sissy maid. I will always be eternally greatful. 

ENTRY 3

The month of February has been a very busy one for me. But it has been even busier for Ms. Robin and her daughter, Miss Marie. Ms. Robin continues to train Miss Marie and many submissives have been visiting because they wish to be dominated by these two beautiful women. However, when there has been a few days break between visitors I am used for Miss Marie's training on specific areas that are either not requested often by visiting submissives or are training techniques that are used on a lifetime live-in submissive such as myself. The hardest part for me has been the weekly (and sometimes even more frequent) discipline sessions which Ms. Robin will typically supervise while Miss Marie administers. As I stated before, Miss Marie has no attachment to me so she is quite brutal in administering my discipline and any pleas for mercy on my part fall on deaf ears. Miss Robin has acquired some new toys recently and has been using them to expand Miss Marie's knowledge. One of the devices is a set of nipple clamps that are attached to a bar with a screw in the middle of the bar that when turned pulls the clamps away causing them to tighten while pulling on the nipples harder and harder. Ms. Robin has discovered that this device when used on me in conjunction with my electronic milking can make the process go even faster. My last milking took just 3 or 4 short minutes to complete. Ms. Robin is thinking that my next milking will find me being bound with her or Miss Marie conducting the milking. Then the electricity will be left on while the nipple clamp screw is twisted and twisted until the clamps finally come off my nipples. Depending on how fast the screw is turned, Ms. Robin has warned me that I might have to endure the agony of the electricity flowing through my empty prostate for 10 minutes, 20 minutes, 30 minutes??? It all depends on my level of suffering. Ms. Robin believes that I will be gagged as she hates to hear me begging for mercy and if she has her daughter, Miss Marie, do the milking then this might be a good time for a caning.
 
The last time that Miss Marie conducted a discipline session on me she asked her mother why her relationship with me was the way that it was. Before starting her training Miss Marie said that she could see the strong love that Ms. Robin and I share for each other. Miss Marie had always thought that we would be married. Much to my total embarrassment, Ms. Robin laughed at this statement and went on to tell her daughter that while she did indeed love me with all of her heart, she could never marry me because of my inadequate sissy clit and the fact that I was gay. Miss Marie was shocked by this and started to beat me harder with the strap that she was using on my ass. Ms. Robin then proceeded to tell her how she has had me suck the cocks of various lovers that she has had and how she has not allowed me to see her naked in over 5 years now and how she has me blindfolded whenever she has me service her. I continued to be mortifyed as Ms. Robin told her daughter that she hoped to one day find "Mr. Right" and that at that time I would be moved to permanent servant status with absolutely no access to either service her or have any kind of participation in her sexual fulfillment ever again. Ms. Robin then told her daughter that if I performed my duties to her satisfactorily that once a month I would be sent to a gay club where I would be bound to a urinal in the clubs bathroom and be forced to suck the cocks of all those that chose to use me in this way. And the ones that chose to use me as a urinal had better not outnumber the ones that wanted me to suck them off because then I would be disciplined severely by the club owner and I would have to practice sucking cock on a 10-inch dildo for an hour in the morning when I awoke and an hour at night before going to sleep. That would mean for that month I would only get 4 hours of sleep a night as my current schedule has me working 18 hour days and that time would not be shortened. Miss Marie laughed when she heard the details of my future. The two of them discuss this all the time now when my weekly discipline is being administered.
 
Speaking of the weekly discipline, I am not losing weight as quickly as I had hoped for and right now I receive 47 strokes or at least 95 strokes if I mess up and gain weight. One week, just for fun, Ms. Robin had me weigh after I had eaten a large evening meal. The rule is that if I gain 1 or 2 pounds that I receive double the strokes (how many pounds I am away from my goal weight of 250 pounds times two) but if I gain more than 2 pounds I receive however many pounds I am over (the number is always rounded up) times the number of pounds that I have gained. So if I gained 5 pounds (example: 295 to 300) then I would receive 250 strokes. The time that Ms. Robin had me weigh after eating I was 7 pounds heavier. This resulted in 399 strokes as I was now 57 pounds away from my goal weight. And then I found out the next week that I had to get below my lowest recorded weight in order to go back to minimum punishment. Even though I lost 3 pounds that week, I still received 216 strokes. For two weeks in a row my poor sissy ass was sore for the entire week.
 
Well, that is all I have time for now. I know that Ms. Robin is hoping to get some videos up on the site soon of not only some of my electronic milkings but also of Miss Marie and some of her sessions. It is now time for me to get back to my duties as Ms. Robin's sissy maid. 

ENTRY 4

The month of March is almost gone so Ms. Robin has requested that I give an update on my sissy maid status. First, I will talk about my weight loss. It has not been going as well as either I or Ms Robin had hoped for. An exercise routine is being worked out and I will have further information on that in my next entry. Ms. Robin's daughter continues to administer my weekly discipline and believe me when I say that she has not lightened up in the intensity of the punishment that she administers. She was in a hurry to go out on a date for my last punishment and administered over 200 of the hardest strokes with the strap on my ass in record time. It only took her about 5 or 10 minutes and my poor sissy ass was on fire. She berated me for not losing weight faster and causing her to have to take up precious time to discipline me. Ms. Robin then stepped in and informed me that a robospanker (www.robospanker.com) has been ordered for my discipline and that depending on the intensity of the spanks administered will determine whether my punishment every week remains the same or if it gets doubled or even tripled. More on the arrival of the robospanker in my next entry.
 
Ms. Robin also informed me that very soon I would be leaving 5-inch high heel training and moving to 6-inch heels very soon. She is looking for the appropriate pair for me to wear. She does not want a spike heel as Ms. Robin wants me to be able to wear them all the time when I am performing my sissy maid duties. I have also been told that my corset training will begin when my weight drops below 275. Ms. Robin wants to use the corset training to improve the posture that I carry myself with when I am performing my maid duties.
 
I am working longer and longer hours each day and yet I continue to feel that my life is more and more fulfilled. I am eternally grateful for this opportunity to live out my dream lifestyle and I live to serve Ms. Robin to the best of my abilities for the rest of my life. I love her more than anything in this world.  

ENTRY 5

My life has once again changed dramatically. The Robospanker (available at www.robospanker.com) has arrived and Ms. Robin just loves it. She received the first model that is controlled with a wireless remote control. When Ms. Robin first used this on me she told me that it would only be used for maintenence spankings on a weekly basis whenever her daughter, Miss Marie, was unable to administer my weekly discipline. But she is so pleased with the job that the machine does that Ms. Robin has decided that this is how I will be disciplined from now on. She has had me adjust it so that it administers the hardest swats to my sissy ass and the speed is up at its highest point so the swats mount up very quickly. And there is no more waiting for a once a week session to administer punishment spankings in addition to the 10 minutes of weekly maintenance discipline. Rather, Ms. Robin is administering punishment sessions daily and if I don't complete my maid duties to perfection I get sent for a session on the machine 2 or 3 times a day. Suddenly at the end of my long work day I am ordered onto the bench and have to endure 10 or 15 minutes on the machine because of flaws in the work that I did that day during my 12 to 18 hour shift. So far while using the machine my chastity belt has been removed for fear of what the paddle hitting the chains on my ass might do. But I know that will not last long. The bench that came with the spanker has a vibrator in it that rests right on my sissy clit. With the pain from the spanking ensuring that my sissy clit remains soft the vibrator effectively milks me and Ms. Robin has begun to have me place a bowl on the floor to catch the drippings. And there have already been punishment sessions where she has had me unplug the vibrator in the bench so that all there is is the pain of the spanking.
 
Ms. Robin is already thinking of new scenarios that i am sure I will have to endure soon. Like she is thinking that the next time her lover comes over that she will cuff me to the bench and let me sleep there for the night. She said that she would turn on the spanker every time that she has an orgasm and leave it on for 5 minutes or so while her and her lover relax. She then told me that the last time her lover was there that she had 11 orgasms through the night. She then told me how she just fell asleep after some of them and that I had better hope that she doesn't fall asleep after turning the machine on because then I might have to endure being spanked continuously for hours. She thought MAYBE as a safety measure against this she might let me turn the intensity down to medium. But she has assured me that the low setting will never be used so I can just forget about that. Well, I have just been summoned by Ms. Robin so I will end this entry now. There should be video of the new spanking machine in action as well as some video of a couple of recent sessions featuring the ever so dominant and beautiful daughter of Ms. Robin, Miss Marie.  

ENTRY 6

What a difference a few weeks can do as I feel like my life has completely changed. Ms. Robin is enjoying the Robospanker so much that there hasn’t been one day that I have not found myself spending some time being disciplined by this machine. There have been other developments in regards to my sissy maid service that I provide to Ms. Robin. She has come up with an exhaustive list of all the duties that I am to perform each day, 7 days a week, 365 days a year. One of the first new rules that has been implemented is that I no longer get any days off ever! Ms. Robin insists that this is appropriate for me as there is now nothing else in my life except my service to her. Ms. Robin has also stepped up the performance level that is expected from me with regard to my chores. She inspects constantly and has even taken to dirtying a tiny unseen area on my chore list for the day just to make sure that I am thorough on cleaning each and every square inch that is required and don’t just let a cleaning given the week before carry the chore for that week with my only giving it a cursory going over. Ms. Robin has taken to adding 5 minutes on the Robospanker for each demerit that is given to me during inspection in addition to the standard 5 minutes that I receive daily no matter what. If one night she doesn’t inspect then the next night can be very long. One night I was on the Robospanker for 35 minutes and my sissy ass was beat bloody by this machine. And I had better keep track of what needs to be fixed because it must be fixed by the next inspection or that 5 minute penalty stays with me for a week until that area is inspected again. So far I have managed to avoid having a penalty carry on for a week but I am still averaging about 15 minutes per session on the Robospanker. Ms. Robin is also having me provide detailed notes on how long tasks take me to do so that she can ensure that I always have a full work day. Already Ms. Robin is talking about what it might be like to have me in full service 12 hours a day for an entire year. This has become Ms. Robin’s latest goal that she has set for me. And the exercise program is in full swing as well as I have to ride an exercise bike for a specified period of time (it started at 15 minutes and is now up to 20 minutes) and I have to ride it hard enough to generate a good sweat that Ms. Robin can see on her closed circuit camera or a 10 minute bonus punishment will be added to my time on the Robospanker. I am weighed each Sunday and the same rules that I described in a previous post still apply. Also, anytime it is time for a session on the Robospanker, the old chastity cage with the spikes in it must be attached. Ms. Robin is still concerned about what might happen when the Robospanker strikes the chains of my regular chastity belt. It has now been about 4 weeks since my last milking and Ms. Robin has told me that the next milking she will participate in and it is going to be really fun (for her only) and she has some surprises which I am sure that the surprises involve the new gynecological table that Ms. Robin recently added to her dungeon. I will try to write just what went on with this milking in my next entry as I have a lot of work to do before my work day is through.

ENTRY 7

My relationship with Ms. Robin continues to evolve in very dramatic fashion and in the relatively near future will be changing dramatically. As many of you know, Ms. Robin has a chronic back condition that limits her activities sometimes quite severely. That is one of the reasons that the Robospanker was purchased so that discipline could be maintained for me even when she did not feel like doing it. But there is another reason for the Robospanker as it is an essential tool for my training as Ms. Robin’s sissy maid. Ms. Robin is currently on a path that will lead to getting her back fixed through surgery and resuming the active life that she has missed so dearly. When she is able to return to a more active lifestyle Ms. Robin will much more aggressively pursue having other lovers of both the female and male persuasion. For me this means I will be cut off from all physical contact with her and will be reduced to a permanent servile sissy maid status. This was explained to me during a recent punishment session where Ms. Robin wanted to get in some practice with her single tail and wanted to try out a new whip that she had recently purchased. I was strung up in the basement dungeon with a new spreader bar applied to my legs, blindfold in place, and wrists hanging from hooks in the ceiling. This position puts me in the middle of the room so that access is available to all parts of my body both front and back. While whipping my body Ms. Robin explained how things were going to change dramatically when her back was fixed. How she would be able to travel again and how I would have to serve her well as a sissy maid and have to endure permanent chastity. She stated how I would probably have to remain at home while she traveled with her lover because of the heavy work schedule that she would have in place for me. She explained how when one does the menial job of a maid that you have to work between 12 and 16 hour days in order to make enough money to be able to continue to live in her household. Ms. Robin stated that 30 hours a week would just barely be enough to keep up with the housework in her house and that she wanted to find me 5 to 8 other households to provide maid services for and that each of these would demand 10 hours a week of my time. When one adds it all up that will be between 80  and 110 hours a week. Since I will work 7 days a week this means a minimum of 11 hours to a maximum of 15 hours a day just doing housework. Then an hour a day for exercise and an hour each morning to shower and apply makeup and get dressed in the uniform of the day and it is easy to see that I am in for a very hard life of menial drudgery. Ms. Robin has also let me know that a Prince Albert piercing will soon be given to me so that a piece of ¾ inch PVC pipe can be locked onto my sissy clit so that I will never get hard any more let alone be able to orgasm. While now I am able to worship at Ms. Robin’s sacred temple when she has a lover all physical access will be denied. Her goal for me is total sexual deprivation and maximum workload. She also stated that to cut down on the cost of having me live in her house that I will probably be moved to a diet of old stale oatmeal and dog food that can be purchased on sale. And milkings will be moved to at most once every 2 months as that should be adequate to keep my prostate healthy. Ms. Robin is very concerned with maintaining my health as she wants me to be able to serve her for as long as she lives or as she puts it, “for the next 30 or 40 years.”  And she has promised me that while she does indeed love me with all of her heart and soul, this will not prevent her from be unspeakably strict and cruel with me and how she looks forward to being able to punish me in cruel and torturous fashion and how even the relief of milkings will come at a painful price for me. Such is my life as Ms. Robin’s sissy maid and I love her with my whole heart and soul for being willing to give it to me.

ENTRY 8

The past month has been one of tremendous ups and downs in my training. Ms. Robin has been feeling a lot better lately and with her chronic back pain subdued for the moment has given her the opportunity to discipline me herself on a more frequent basis. The Robospanker is still used for daily discipline but the more severe weekly discipline sessions have found Ms. Robin holding the whip. At first I was so happy because I got to feel the closeness and touch with Ms. Robin again and that is something that I had been forced to do without for to long. And while the touch of Ms. Robin more than makes up for it, I have also discovered that my life as Ms. Robin’s sissy maid has also given her the ability to be very cruel in her punishments of me. Last night we went to a play party of our local BDSM group and Ms. Robin could not wait to strap me to the cross and publicly punish me in a way that was more extreme than anything that I had ever experienced with her before. Photos will be posted here that show the remnants of the severe punishment that she administered to me while I was hanging from a cross in nothing except my ever present chastity belt. Ms. Robin is continuing to wean me from physical contact with her in preparation for her finding a lover and any kisses are only allowed now on her cheek rather than mouth to mouth. Of course, she always reminds me that I am still allowed to kiss her feet and ass and even occasionally to worship at her sacred temple of womanhood. Ms. Robin has informed me that when her lover is found that even kissing her cheek will be gone as well as worshipping at her temple. Her feet and ass will be all that will be left. She has told me that this will enable her to increase the sadism of her punishments of me as well as increasing the amount of time that she has a machine (the Robospanker available at www.robospanker.com) punish me. My work schedule has continued to increase and I find myself being worked so hard that I am literally falling asleep almost as soon as I am allowed to lie down only to have the alarm go off at 4 am. getting me up to get started on another menial day of work as Ms. Robin’s sissy maid. I don’t know why I love this life such as it is, but I do and I love Ms. Robin greatly with all my heart for allowing and making it happen for me.

ENTRY 9

Another month has gone by and more changes have been made to my life. Ms. Robin currently has me on a pet food diet. She started out with those 'Beneful' dog food containers that look almost like regular food complete with vegetables. Then she wanted to save money so she switched to the plain label canned dog at a $1.75 a can for 13 oz. I knew I was eating dog food then as it was just awful. But, when you only get 2 meals a day (my morning meal is a cup of oatmeal) and then after working a 12 hour shift as her sissy maid one can be rather anxious to have a 13 oz can of dog food. But this week she surprised me again by deciding to switch to cat food. For my evening meal I will have 3-3 oz. cans for a total of 9 oz. Mistress said that I am not losing weight fast enough and she thought that the fish in cat food might provide me with a little extra nutrition. It was particularly humiliating today when I accompanied her to the grocery store and had to watch as she purchased all the foods that she likes without regard to cost and then shopped carefully to get a 24 can container of cat food which she had a coupon for. The only coupon that she used! The grocery bill was $122 of which my food for the next 8 days cost $11 dollars after taking the $1 off coupon. I account for less than one-tenth of the food cost and I have a feeling that the cat food is going to be a lot worse than the dog food besides being a lesser amount. It is one of the few times that I could see Mistress come out to watch me eat with a big smile on her face. She really enjoyed my new diet. Ms. Robin was so pleased that I found the cat food to be ten times worse than the dog food. As a reward (if you can call it that) Ms. Robin took me out to the garage and strung up my hands and applied a spreader bar to my ankles after having me get naked (with the exception of my chastity device which is always worn without exception). Ms. Robin also attached a pair of nipple clamps and tying them to my chastity device so that if I didn’t keep my stomach in extra pressure would be put on the clamps. Then she proceeded to discipline me with her strap, a new riding crop, and most diabolically, a dead branch from her rose bushes that was especially painful as the thorns bit into my flesh. After kicking a dog bowl underneath the tube of my chastity device Ms. Robin stated that it was too hot for her so she went inside saying that she would be back for me later. She left her cell phone on speaker so she could talk to me from the comfortable air conditioned house. The first thing that I had to do after about 20 minutes of hanging there, feeling the flies and mosquitoes constantly landing on me especially on my bloody ass, was I had to ask to relieve myself. Ms. Robin said that it was OK as long as it landed in the dog dish. As I was blindfolded I had to let the urine out just a little bit at a time so that it would drip straight down into the dog dish. It took me about 15 minutes to relieve the pressure in my bladder. By this time the nipple clamps were incredibly painful and that pain was giving me the feeling that I get when being electronically milked. I noticed that by thrusting my hips and bouncing on my toes I could send pain through my nipples and it seemed to reach right down to my prostate. I could feel the release coming and asked Ms. Robin’s permission to release. All I heard was laughter and then I heard Ms. Robin say: “How pathetic you are my little sissy maid. What do I have the electronic milking PES unit for if all I need to do is string you up and hurt your nipples a little bit and you release. Sure go ahead, but I will remember this as perhaps your most pathetic day in your service to me. You really are destined to just be my sissy cuckold maid if this is how you can obtain release.” So I started bouncing and moving my hips in a way that caused the nipple clamps to jerk my nipples hard. It took another 15 or 20 minutes before I was releasing. Now understand that the tube chastity device that I was wearing is only ¾ of an inch wide and 2 inches long. My sissy clit did not get hard at all and yet soon I heard the drip of my release going into the dog bowl. I had to hang there for what seemed like forever (but Ms. Robin says was only 10 minutes) waiting to be released. Ms. Robin was amazed at the remnants of my release floating in the dog bowl almost half full of urine.  Ms. Robin of course had me consume all the contents of the dog bowl as she explained that there would be no electronic release tonight as she had intended and that she would need to think about if the PES unit would even be used this month. Ms. Robin said that it might be to painfully fun to hook up the PES the next time she has me in the garage (yes, she loved it so much there will be a repeat) as it has a tendency to make me not only release my prostate but also my bladder as well if I haven’t been allowed to use a bathroom for a few hours before. The fun part in her eyes is that I wouldn’t be able to control the flow of urine then and it would cause me to miss the bowl with my uncontrolled urine release. She thought that the appropriate time after release to leave the PES run is about an hour just so she can make sure that I am totally drained. When I explained how painful that would be, Ms. Robin said that I needed to learn how to deal with it because she wanted to make sure that I was completely drained as she feels it is essential to my health. Well, that is all for now. I will have another entry as soon as I can. It all depends on how busy I am with my duties as Ms. Robin's sissy maid.

ENTRY 10

My life continues to evolve as Ms. Robin’s sissy maid. The latest change is a highly intensified heel training program. Ms. Robin is determined to have me performing my household duties in 6 ½ inch heels by the holidays. Right now I can’t even stand in the pair of 6 ½ inch pumps that Ms. Robin purchased for me. Currently she has me wear a pair of 5 inch spike heeled boots that lock on and stand for a minimum of 1 hour per night. Then I am allowed to go to sleep but I must sleep in the heels as Ms. Robin has no desire to unlock me until the next morning. The goal is to increase the time by an hour each week until I am up to 4 hours. Then I will change to 5 ½ inch heels for the four weeks after that and then 6 inch heels for the four weeks after that. This will bring us to the end of October which means that by Thanksgiving Ms. Robin expects me to be ready to serve in the 6 ½ inch heels.

She has even incorporated the heel training into my monthly milking. This was the procedure that was followed for this months electronic milking. First off let me say that I was excited about this milking as Ms. Robin informed me that it would be performed in her actual physical presence. This has not happened in the past few months as Ms. Robin is prepping me for when she finds a lover and physical contact with her will be cut off. But when I found out how the milking was to be performed I felt the excitement slipping away.

Ms. Robin brought out a pair of thigh high boots with a five inch heel and had me put them on and lace them up tight. In this state it is very difficult to bend my legs or maintain my balance while standing. Ms. Robin informed me that I would be milked for as long as I could stand in the boots plus five minutes when I announced that I needed to stop. She then bound my wrists and pulled them up over and behind my head kind of hooking me to the door in her bedroom as she passed the rope down the outside part of the doorway, under it and then tied it to my ankles. I was effectively bound to the door and could do nothing but just stand there in my thigh high boots with my arms pulled over the top of the door and the backs of the boots just touching the door.

Ms. Robin then proceeded to blindfold me and attached nipple clamps to my nipples, tying the chain that ran between the clamps to my chastity device that is worn for my milking. The ¾ inch in diameter by 2 inch long PVC tube that keeps my sissy clit completely limp has a cap on it that is extremely effective at holding the electrical urethral probe in place. This along with the prostate probe had already been put in place by me as Ms. Robin is above such menial chores.

I definitely felt it though when Ms. Robin turned on the PES unit and quickly ran up the power to the maximum in less than a minute. I almost had to call for mercy then as I teetered precariously on the five inch spike heeled boots. I somehow managed to stay standing though and tried to focus on standing up absolutely straight and maintaining my balance while enduring the electrical torture of the milking. The thigh high boots made it easy to keep my legs straight but also made it difficult to shift my position, however slightly, so I could never find a relaxed position.

Ms. Robin then began talking to me, telling me the various things that she knows humiliates me and advances the milking along to its eventual conclusion. She asked me how I was adjusting to never seeing her naked breasts anymore. She told me about some TV programs that she watched that she knew I would enjoy but they had nudity in them so I was not allowed to watch them. She told me how the 14 hour days that I was putting in working were only going to get longer. She thought that 18 hour days would be about right and that soon it would move to seven days a week rather than just the five that it was right now.

Ms. Robin talked of vacations with her lover and leaving me behind for not only her housework but the housework of others. She reminded me how pathetic I was that I released in the garage just from nipple clamps attached to my chastity device. Ms. Robin reminded me of how I would always be kept in chastity and how milking would be my only form of release. She then stated that I probably could not get hard anyway and who would want my tinier than ever sissy clit anyway.

Ms. Robin talked about how she had read on the web that men kept in chastity for extended periods in tight tubes like mine lost the ability to get erect and those that managed an erection found that their penis would not get as long as it once did. She said one wife’s post talked of how her husband’s penis when she first put it in chastity was 6 inches in length. After 3 years of chastity when she allowed him to get erect (twice a year) he now measured only 4 inches.

Ms. Robin then talked about how pleased she was with the dog food diet that she has me on. She talked about how nice it was to have the extra money as it only cost her about $10 a week now to feed me. She talked about how she would continue to examine closely how I spent money and how her ultimate goal was to deny me all spending on anything for myself with the exception of the $10 a week for my food which this week consisted of 7 cans of Alpo at .69 cents, $3.49 for a gallon of skim milk, and $1.99 for a container of oatmeal. Ms. Robin advised me that however much I went over the $10 that each penny over would be an additional stroke would be added to my regular time on the spanking machine.

This week for example I actually spent according to Ms. Robin’s calculations $21.50. So I will receive an extra 1,150 strokes from the Robospanker. Since the machine administers 7 strokes per minute at the current setting that it is on this means that I have an additional 165 minutes added to my regular time on the machine. This equates to an additional 23 to 24 minutes each day almost doubling the amount of time that I spend being disciplined by a machine.

As Ms. Robin continued to humiliate me I heard her say that she could see the milk coming out of my chastity device and dripping into the dog dish that had been placed below the tube. She talked about how worthless my little drippings were and how I didn’t need to worry as they would never enter or even come close to a woman ever again. When I told her that I could no longer stand as the milking was complete and my legs were just aching she said “OK, let me start the 5 minute timer.”

I had to stand there for five more minutes as she continued with the PES at its maximum setting and continued to humiliate me and expressed how I was perfect for being a sissy maid and that she would train me to be the most perfect sissy maid that she could create. And for me not to worry as she would find a real man to be her lover and that I would then be serving them both in my abject servile position as Ms. Robin’s sissy maid.

ENTRY 11 

I know that other entries that I have written for this journal have talked about life changing events in my life as Ms. Robin’s sissy maid. But the event that I am going to talk about today is an actual life changing event that I am both looking forward to and find myself absolutely terrified that I will fail this critical test. Ms. Robin has been reading a book by Ingrid Bellemare titled “Owning and Training a Male Slave,” (website is: www.male-slavery.com) and the main point seems to be (I have only been allowed to read the 3 preview chapters available on the website) that the only way that a person can be a true slave is that the situation must be a non-consensual one.

I have asked Ms. Robin and she has agreed to move our relationship into this realm. The initial step that will signify this move is an extreme whipping that will cause me to use my safe word and this will be ignored.  Chances are good that I will never even get to employ the safe word as I will be gagged as securely as possible because the whipping will be taking place in Ms. Robin’s garage and she does not wish to have anyone hear my screams. This is not a punishment whipping. As Ms. Robin has informed me, this is just to show me what she is capable of doing to me if I do not serve her to the utmost of her expectations. She has told me that there will be a lot of blood and probably permanent scarring from the whip. This is also a test for Ms. Robin as she will have to put aside her love for me in order to show me that she is capable of not only having me as a slave but is capable of keeping me forever as a slave by this act that shows that she can act with no compassion or mercy towards me. In the past I have known that I can always use the love that Ms. Robin has for me to slow down or stop a scene if it went beyond my limits. This session is meant to not only emphasize that this will never work again but it will also show me that I must continue always to increase my efforts in serving Ms. Robin.

This will stand as the pinnacle moment when I am forced by this non-consensual whipping to learn that the only hope that I have to avoid such a thing in the future is to serve as Ms. Robin’s sissy maid better than I ever have before. I will learn to reach deeper everyday to serve my Mistress. But as I wait for this whipping to commence I find myself terrified on many levels. There is the whipping itself, what if I can’t take it? Since I won’t have a choice I am able to get by this. But another feeling strikes even more terror in me and this is what if I can take it? Will my service to Ms. Robin suffer if I know that I don’t have anything to worry about? And then there is Ms. Robin. What if she is able to perform this whipping and her attitude towards me changes. What if her love and respect for me is replaced with something less than what she currently provides to me. I don’t know if I could live with that. What if Ms. Robin cannot do the whipping? Or is it worse if she can do the whipping and feels guilt afterwards. I would notice this guilt and this in turn would be very detrimental to the type of relationship that we are trying to create. What if I have bitter feelings afterwards? What if Ms. Robin does? These are some of the questions that are striking fear into my heart. But I also know that in my heart I want this to happen because it is my destiny to serve Ms. Robin as her sissy maid and I want to be the best that I can possibly be.

I am sure that Ms. Robin and I will have some long discussions before this event takes place and hopefully by the time of my next journal entry I will be able to tell you how it went so that you know what my thoughts were as well as being able to see the video which I am sure will not be for the fainthearted.  I will ask Ms. Robin to put a special link HERE to the video as soon as it is on the web.

ENTRY 12

It has not happened yet. Ms. Robin and I have had discussions about the move to a non-consensual slave status for me but have so far been unable to implement such a status. I have so many emotions that are running through my mind over this subject that it is about all I can do to focus on something else. My housework has been slipping a little bit of late and I think it is because I am ready to make the move and I feel that Ms. Robin will get angry enough to go ahead and give me the beating that will start me down the course to being reduced to just a servant that is there to take care of her every need and I had better do it or the price that I pay will be a high one.

There are many things to be afraid of as I wrote about in my last entry. The move to non-consensual servant is one that requires that Ms. Robin no longer will truly love me. What I mean by that is that her love for me will be transformed into the love of a faithful servant and not the love of equals that I feel we have now. I know that my feelings for her will change as well. I am sure that quite often I will have feelings of resentment and even a form of hatred. This feeling is difficult to explain but it has to do with what I know will be permanent chastity with only occasional milkings for release. Having to always be dressed in a maids uniform while serving Ms. Robin and being cut off from her on the personal level that I enjoy now.

The reason for the hatred that I speak of is that this is what I want to have happen. I cannot understand why I would want to live my life as the lowest form of servant to a woman who treats me like a common slave and takes pleasure in beating me in ways that she will beat no one else. I witness some of the sessions that Ms. Robin has now with visiting submissives and there is always that look that I get during these sessions when she is whipping them that tells me that Ms. Robin would so very much like to be able to just let go and unleash the beast within her that craves the administration of pain. She cannot ever let that happen with a paying client but the look that she gives me speaks volumes about the pain that I will suffer when she whips me unmercifully. Our discussions have touched on the fact that she will probably come to enjoy this so much that these beatings will probably start to happen on a regular basis. And then when the love of her life is found I will have to endure the total lack of attention that will be given to me and I will be expected to administer my own discipline and milkings as part of my routine of service.

I sense that there is a beginning in Ms. Robin to start pulling away from me. She has expressed that she has no desire to milk me, gives no thought to how difficult it is for me to endure the permanent chastity, and that if it wasn’t for the milking time showing up on her calendar she probably would never even give it a thought.  And it has become a natural habit for Ms. Robin to deny me any view of her naked body especially her beautiful breasts and she has me work in the menial job of housework for long enough that my TV time has become so limited that it has become easy for her to make sure that I never see any nudity at all on TV as well. She has indicated that when I am moved to the basement that I will have to sleep on a cot that will be placed in a tiny alcove under the stairs and that there probably will not be any TV for me to watch and that if there is a TV provided that she will put blocks on all stations that have any type of nudity so that even the occasional show that I might get to watch now that doesn’t have any nudity or that she has screened and deemed appropriate will be prohibited.

I ask myself all the time how I could want such a thing and yet it is what I crave. I actually feel the same anger that I think Ms. Robin is starting to feel towards me as I wait for this training to begin. Is it to begin this Friday when Ms. Robin has scheduled it to? I don’t know but I do know that I will always love Ms. Robin with all my heart and I will always strive to be the best possible sissy maid for her that I can be. I can see the anger building inside of her just as I feel it inside of me and know that this is the push toward both of us reaching the point that we want to be. I understand that a certain level of hatred must exist on both of our parts for each other in order to bridge our way into the relationship that I believe that we both want. I just want to encourage Ms. Robin to know that my love for her will never die and that when I am at my most venomous with hate that it just means that I am progressing into the area that I wish to be.

When I beg her to stop and to just love me for the sissy maid that I am, I want her to know that it is okay to hate the little sniveling whiner that I will have become and to further beat me until it passes. Once this training and transformation has begun I understand that it must continue uninterrupted and with the ferocity of the hatred that you will generate toward me. My love will endure but it would be damaged severely if you stopped what you had begun because you allowed your love for me to win out. Rather, Ms. Robin, you must let the anger flow through into hatred because it is that hatred that will give you the energy to actually train me to be the perfect servant that you desire.

This will take some time and many more discussions but you must know that I know you will always love me just as I love you forever as well. Ours is just a love between sissy maid and Mistress. There are very few people that can say that they have a love like that. It is love on a different level than the love that you will have for your future husband.

ENTRY 13

I am now a slave. I have endured not one but two brutal whippings (the first of which is posted with both photos and videos) designed to break down my resistance to my new status. There are more whippings in my future and I would anticipate that they may become a weekly event for an extended period of time. Ms. Robin has demonstrated to me that she is not only able to administer these whippings with no feelings of sympathy on her part but also that she is able to administer them with an almost uncontainable joy at the power of her position. Ms. Robin has begun to incorporate other changes into our relationship to enforce my slave status. When in the house now I am required to be naked with the exception of my chastity device. When I enter her presence I am required to be on my hands and knees with my head bowed far enough down to where my nose is touching the ground. I am required to remain on my knees with my head bowed while I wait to serve her or I am ordered to go do housework which must be done in my complete maids uniform within a specific time limit. The changes are ongoing as well. As Ms. Robin becomes more comfortable with my new status she finds herself wanting to hurt me more than ever. Already she is talking of branding me with her mark which she has already designed, getting my slave registration number and barcode tattooed on me, having a Prince Albert piercing done so that my penis can be permanently locked up. My last milking (the video and photos have been posted) was over in a shorter amount of time than it took Ms. Robin to prepare me for it. The humiliations just never seems to end. And yet I find myself feeling very satisfied with the way that things have been going. At the same time I feel a certain amount of terror deep in my heart.

The terror comes from the feeling that Ms. Robin will so enjoy the power trip that having a slave is giving her that she will lose the ability to see the good in me. This is a very difficult concept to explain but I will give it a try. I already feel that the love that Ms. Robin had for me in the past is gone. She no longer views me as a partner in her life but rather as a piece of property. I understand and expected that she would lose the love that she had for me but part of the side-effect of this is that it puts in my mind that I can now be disposed of. Before I always had the feeling that Ms. Robin could not live without me, and more importantly, would not want to live without me. But the sad truth is that now she has made it clear that she can live without me and that this is part of the price that I must pay for allowing her to accept me as her slave. As each of the whippings takes place I can feel in the intensity of the strokes that her feeling is that she wants to enjoy the whippings as much as possible because there will come a time when I am not around to provide her with this enjoyment. This is part of the non-consensual nature of being her slave that I have to accept but that does not mean that it is easy. This is all driving toward Christmas day which has been made decision day for me. I have been told that this is the day that I will have to make the choice of continuing to serve as Ms. Robin’s slave or going back to being her submissive. While Ms. Robin says that whatever my decision is it will be okay with her, I am getting the feeling that there is more to it than that. I don’t think that in her eyes I can go back to being her submissive and I am horrified that I may not be able to take the brutality that is involved in being a slave for Ms. Robin and I have been having nightmares about saying no to being a slave and her then telling me that I have to leave her home. Ms. Robin is my entire life and I could not bear to be apart from her. So I feel that I must take it all and trust in Ms. Robin’s judgment that she will never ask me to leave unless it is for a reason beyond our relationship. But in order to place this trust in Ms. Robin it is critical that I make the correct decision on Christmas. I feel that the whippings are going to become even more brutal and frequent as Ms. Robin is testing me to ensure that I can fulfill her every desire in what she wants from me. At the same time, I also think that she wants to have a perfectly trained slave that when she makes the decision to give me to someone else (if she has to) that I will make her proud in that I would be the best thing beyond all expectations that my new owner would have.

Therefore, it is my focus right now to try my absolute best to be the slave (in-training) that Ms. Robin wants me to be. Will the punishments become more frequent and brutal? I would not be surprised. Is Ms. Robin going to do everything in her power to get me to say “no” to being her slave? I think so, and the reason for that is that she wants to make sure that I am fully aware of what saying yes will mean. Do I expect to say yes on Christmas day? Of course I do. It would be foolish of me to endure anymore humiliation or pain if I did not have the expectation of saying yes when the time comes. I feel in my heart that I am destined to be Ms. Robin’s slave. I can only hope that it is for the rest of my life. The one thing that has changed is that I can foresee Ms. Robin dismissing me from her service. There is a certain bitterness in that realization but also complete acceptance as I realize it will be because Ms. Robin has found her true love and that this person is unwilling to have me continue my services to Ms. Robin. I know that Ms. Robin will find me an acceptable new home but the unknown is always something to be feared. So I look to the future with fear but also a sense that it is still within my control to meet whatever test Ms. Robin puts me to and become the best slave that she could ever hope to have. I want to close by expressing my undying love for Ms. Robin and my hope to be your humble slave always and forever.

ENTRY 14

Decision time is approaching. Christmas day is just a few days from now and I feel terribly conflicted. It is difficult to feel very slave like when there is such limited time for training due to outside world responsibilities. While I have endured three beatings from Ms. Robin of a severe nature there has not been one for over three weeks now and I think that the conflict lies there. After witnessing the obvious joy that Ms. Robin felt in beating me I do not understand why it does not happen on a consistent basis. She really has shown little interest in me at all recently and while referring to me as her “slave” now I feel that if I don’t say yes that I will be letting her down. But at the same time, by saying yes I feel like this is acknowledging that this is all she has to do to have me as a slave. And in order for me to honestly accept her offer to be her slave I have to know that I am going to be fulfilled. This is difficult to explain but I will try.

It is not only Ms. Robin who gets something out of having me as her slave but it is also myself that gets something out of the honor of serving her. I do not enjoy getting beat yet somewhere deep inside me I crave it. I do not enjoy being naked always in her presence (with the requisite chastity device of course) but in that same deep place it touches an unknown desire. I do not enjoy not being allowed to view Ms. Robin’s beautiful breasts but when I am able to sneak a glance at them it makes me feel guilty and I feel a desire to be disciplined but never am. I feel like Ms. Robin wants to hate me in order to make having me as her slave possible for her and I feel like it is right there just below the surface but for some reason the deep love that she has for me stops the hate from being truly released.

How do I communicate to her that she needs to use her deep love for me to unleash the hate and that this will enable her love to grow in the direction that she and I both want it to go in. I hope for a deep discussion of these issues is had before decision day because it needs to come out before I can answer in the positive. Ms. Robin wants a slave that will be obedient and serve her every desire and I want to be that slave for her but I find myself in a position that I have found difficult to overcome and that is the position of having my needs met. Even a slave has needs and if these are not met then how does a slave continue to have the desire that is needed to be the perfect slave. Rather what seems to be happening to me at least is that I get the feeling that while Ms. Robin may have truly lost the love that she felt for me as a partner, she still allows the love for me as a person to dictate how this slave in her life is going to be trained and taught to serve as she wishes when what she really needs to do is channel that love for me into the hate that is required to train me to serve her the way that she wants.

That way she ends up with a better product that will take hardly any effort to manage versus one who is never quite sure what is going to happen, how the training is going to go, what can be gotten away with, and most importantly, how committed is the Mistress that the slave wants to serve and love forever. Serious issues that I feel confident will be discussed over the next couple of days and hopefully will lead me to the decision being an easy one rather than the complicated multi-faceted decision that I currently seem to be faced with.

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