Ever growing, Ever learning...

I don't think my weekend vacation will look like this...

This lifestyle truly is a journey of up's and down's! I think the longer we're on this journey the more we learn and grow. It feels like the development of this lifestyle is bubbling more and more with each passing day, and I'm excited to see where it takes us. This evening Mistress had to stay late for work, I had dinner ready when she got home and after greeting her properly we talked and enjoyed dinner. She needed to work on a few side jobs so she went ahead and spanked me with the crop for my continued bad behavior. Followed by diapering me and locking me in my ankle cuffs with a two foot chain between them, with my heels on of course. It's funny because I'm still struggling to get into a submissive state, and staying there. Which is why I know deep down as does she going to someone who does not see "there boyfriend" when they look at me is going to be the best thing for me. I basically need a weekend of hell, to the point where I go crawling back to Mistress, never wanting to upset her so she never sends me back to that person again. It's motivation really, and with the proper motivation I am capable of amazing things....I'm a driven person, so this will be no different. I've had people message me with concerns of going into a strangers home and being under there control for a weekend with no way to leave.  Let me clear the air; first off Mistress would have been in conversation with this person, also Mistress would have met this person and chatted. Only after then if she felt comfortable would this happen. So please don't think she's shipping me away to be sold into the argentinian sex trade, thats not happening. At least then I might be able to actually get off?! Ha Ha. She's talking to a few whom I have found, but one in particular has kind of stood out and Mistress began communication with her tonight. Mistress has mentioned going to multiple people over the course of this growing process for me through submission. The one she messaged today had a lite conversation with me about what her "making me crawl back to Mistress would entail" bondage, beat, abuse, leave me there...repeat. Which I think is exactly what Mistress is looking for.  Will the person get enjoyment out of this? Sure or they wouldn't do it. But this is more about me coming back to Mistress a melted ball of submissive goo.    It seems like I'm anxious for this to happen, because I am, but not in the way you might think. I will get no pleasure from this, I'm in chastity anyway! The pleasure I will get is the submission I will feel towards Mistress when I return. This will be good for me in essence, because Mistress is still developing as a dominant herself, me being a better submissive will make this process easier for the both of us. Another question I received was "why wouldn't your mistress be there"and the answer is simple actually; I wont see my girlfriend, she wont see her boyfriend it would simply be me as a slave, and a dominant, and thats all we see each other as. No other emotions get in the way, its simple me being treated like I should be. I hope this clarifies some of the concern, don't be concerned! Pray it happens soon so I can get better! As I've stated in many of my blogs I love my Mistress dearly, and I want to be the best I can be at this for her.  The two week period we were shooting for is still high hopes, since I will be traveling alot come the end of September, and I don't think I can wait longer to be a great slave. I have faith it will come through, though I'm scared of it happening I know it will be for the better. Also hoping Mistress develops several friends out of this process in the lifestyle so she can relate to someone in person.
These truly are the most open people you will find in the world and I'm excited about the friendships I'm making through this process. It brings people from all walks of life together, and that's an awesome thing.

Debbie

Affirmation...it's not a game.

Im coming to terms with diapers.

It may seem like we are never at home on the weekends, though I can assure this is not the case all of the time. Lately we have been gone an oddly strange amount, that's changing now. We spent the holiday weekend with Family, well sunday and monday anyway. Awakening sunday morning Mistress was not happy I hadn't messed my diaper, but this was haulted by the fact we needed to get on the road. Driving too our destination we took two cars, I received a text from Mistress B asking if I was plugged, I replied with a hesitant "...no?". She told me she though sissies should be plugged all during the day, to make them more submissive and get them use to having things up there ass....or something like that. I can tell you that was NOT a piece of advice I was passing along to Mistress, though she more than likely already recommended it to her. We enjoyed our get away and I asked Mistress B one question later in the day, if my time with her during training would be only under her roof, or if I would be leaving the house at all. Looking back I almost wish I wouldn't have asked that question. "Some in public, you need to get use to them" was her reply. Use to what I asked, which she stated "your diapers, you need to get use to wearing them 24/7 which is what your Mistress wants, this includes public". Great, one of my biggest fears...diapers in public, I want nothing to do with it! I'm a slim guy, if my pant's are puffy everyone will know, my waddle will be very obvious. "I truly wish you would re think that, I don't want to be exposed or humiliated, I don't want others to know I'm diapered ma'am" (I HAVE to address her as Ma'am and Mistress as Mistress in all communication or it adds 10 spankings to my first punishment session with her...I'm up to 81 apparently, though I think the count is off...my opinion doesn't matter).  "Thats why it's going to be fun! You'll be extra submissive which is where your Mistress needs you".   I enjoyed the day with Mistress, I'm so lucky to call her mine, and even lucky enough to begin the journey to serve her. She truly is stunning, she has a glow about her when she smiles that reinforces why I want to be with her forever when I see it. Laying in bed she had already grabbed a diaper out of the suitcase and put it on me, I was cuddled up next to her when I asked her, as nicely, as sincerely as I could... "Please don't send me to Mistress B....she's alot meaner than you, I think it's going to be a nightmare".  "No, your going, its for sure now...don't ask me again, you need to go" was all she said. Even today it became more evident, they were texting a lot, and it was obvious. Sitting on the floor eating dinner when we finally returned home Mistre
ss giggled and kept smiling when she was looking at her phone, she said "diapers in public!" in a bubbly voice, and I knew my fears had been reaffirmed. Though I'm scared do not think Mistress is crossing a hard limit, she's not. She has few limits (she knows I'd never do anything homosexually related, and she would never make me do that) but other than that she has full control. If I truly wanted to stop this process I could look her in the eye and make it end, but I see how much happier she is now. After dinner she told me to lay on the bed, she inserted the medium plug in me and put on my black thong to hold it in. "Come on, across my lap now" she said sitting on the edge of the bed with a wooden spoon in hand. I didn't even fight it, it would have been pointless.
"You were bad this weekend" as she spanked me after each of the following statements.
-Yes Mistress  I replied.
"You did NOT call me Mistress, you are to do that EVERY Time"
-Yes Mistress.
"You did not behave and you weren't respectful"
-Yes Mistress (the blows began to multiply between statements)
"You are to always hold the door for me and allow me to enter first, anywhere, anytime, no questions!"
-Yes Mistress

I understand why I must be kept in chastity now.

"You are to listen and not sigh when I ask you to do something"
-Yes Mistress (now my ass is glowing and each strike is causing me to squirm)
"You are to do whatever I say immediately with no hesitation"
-Yes Mistress
The statements stopped and the spanking continued for a few minutes
"You understand why I'm sending you to Mistress B?"
-Yes Mistress
"It's going to be hell! this spanking is going to seem like massage!"
-Yes Mistress with pain in my voice
"Your going to be sleeping standing up chained in a closet! So fun!"
-Yes Mistress
"She's not going to put up with your attitude, your ass will be raw!"
-Yes Mistress
"Do you understand what I've said sissy?"
-Yes Mistress
She left me across her lap, gently rubbing my bright red bottom. She held me for a minute then told me to get to cleaning and report back when I was done. In the middle of my attempt to shine the kitchen, she put the posture collar on me, as if the plug wasn't bad enough. An hour passed and I was done. I really needed to use the rest room but she simply replied "too bad" and ignored me. She then took me into the bedroom and told me to prepare the chains on the bed for my hypnosis files. Chaining my arms to the bed (I might add when she plugged me, she put my heels on me, they are still on) she pulled them tight, blind fold which was wrapped again to ensure darkness, and my files began being pumped into my head. The files were some I hate, because I'm an ass guy, Mistress's ass is perfect and large...the good kind of large, shes not overweight by any means. The file was focused on building a stronger ass fetish for any women I see, yet not being allowed to get off. It played on loop for what seemed like hours. When she finally turned it off I was so happy to be out of the darkness. I got up and stretched and immediately wet my diaper without thinking about it, then I messed without giving second thought.   "What was that" I thought... I walked by the window in the kitchen and looked at myself in the reflection... heels causing my ass to stick out, legs straight, diaper wrapped around me. "This is life now, this is what your becoming...at least it looks...kind of cute?" was what rushed through my mind. It's sad how scared I am of changing, I'm becoming more submissive daily, more dependent on her daily...and training truly hasn't begun. I don't think it will until she sends me to Mistress B's. Mistress said she will have my first weekend training planned and a date by mid week more than likely, and its possibly as close as the coming weekend.  When Mistress had me across her lap, Its clear shes growing much more confident. And my spankings tonight did not count towards my total tally for Mistress B's... She's still going to spank me for not addressing Mistress properly as well.

Goodnight, I hate falling asleep in a very diaper.
Debbie.

Morning sex, Bedtime sex

"Come right back to the bed, I feel like having sex sissy..." was the first thing Mistress said to me through my morning grogginess. I was taken back, she was breaking out the strap on at crack of dawn...well four hours after the sun rise. She didn't use the big dildo, but she had me bent over the bed for about ten minutes, it felt pretty good, the small one always does. I've noticed she never does me very long, I'm sure this will change in time, as my hole becomes more receptive to receiving things. She did not take me right away, my diaper was rather soaked and she wanted me to stay in it for awhile while I cooked her breakfast. She also took pictures of my diaper and sent it to her acquaintance I believe. After cooking a wonderful breakfast and she finished pounding me, she spanked me for my continuing of being bad. It was nothing is specific I believe, just in general behavior she hasn't been happy with. This is not surprising given my overall resistant  the past few days. We spent the day visiting an old friend of mine and returned home around 9pm. She told me she had some things she wanted to do before we laid down for the evening. "Im going to fuck you again, get ready on the bed, your cage is staying on". I didn't argue, though I wanted to... I just wanted to be put in my diaper and left alone. One thought on the diapers are they are becoming a safe place for me; I'm not in chastity in them, she can't stick anything in me or spank me...they are kind of nice, not to mention kind of comfy, I'm growing to like them a lot which I know was her intention. When she makes me dependent on the diapers I'm dependent on her...  But my diaper didn't come on, and after she mounted me from behind with the smaller dildo, she went into the bathroom and put on her large one. The smaller one had been cleaned and was shoved into my mouth for me to suck on while she forced the large one into me. I'm still not use to this monster, I feel so different when it's thrusting into me, violated, scared, waves of pleasure and my mind races. What ran through my mind tonight was is the only point of her training me on dildos only going to be reserved for her dominant pleasure? Or does she have underlying plans for the far future where she wants me to be prepared?! I can't see her "whoring me out" but she has joked about it numerous times. I know I'm just thinking crazy. The session went on for about 20 minutes, and I wanted it to end so badly. When it was finally over she let me sit on the toilet rather than diapering me immediately; for which I was very thankful. When she doesn't let me, I go to bed feeling used. But I'm in my diapers and panties now, she also has been MUCH more stern on me calling her Mistress every time I speak to her, she said she was keeping count to tell her new dominant friend.  An update on that field; Mistress said she wasn't sure when that was going to happen since apparently schedules aren't alligning. The three week window might not be met sadly, but then again it may work out, so we'll see. If Mistress B can help me become a better slave to my Mistress, I want to do it as soon as possible...because I hate letting her down. I want to take this seriously for her. I want to be the best sissy in the world, for her. I want to obey and listen and do as I'm told, yet I'm having a hard time breaking down these barriers in my mind. I hope schedules align so it happens in the next three weeks so I can start serving my Mistress to the best of my ability.  Going to spend the holiday with Family, will be back Monday night.  Thanks for reading, please ask any question you like.

Debbie

Sending me off to be broken in?

There was no flaunting of a sissy through out the house, chains clinking between heels as she cleaned gracefully shaking her ass as instructed by her Mistress. No strap on violated me, no hypnosis files were played for hours on end, well yet anyway. Yet despite all of this it was one of the most stone setting days thus far, today solidified just how serious Mistress is, just how far she wants this to go, and made clear she wants to mold me into her maid, her servant, her sex toy, her sissy. How could all of these things happened without D/s or kink involvement today? Well there was some of it, she just diapered me for the evening but not before spanking me telling me how bad of a slave I was. She had me greet her when I got home, and reddened my ass with a wooden spoon. Im sure she would have done more if it were not for our friends coming over for dinner and chatting all evening, which was wonderful. How could it be then that today was so monumental of a day? 

As I've talked about in recent post, there is a Mistress who lives a few hours away. We've talked alot the past few days and she truly has been a help in aiding me to break down my road blocks in my mind, to accept becoming my Mistresses slave. She's helping to break down the barrier of my viewing her only as my girlfriend and not my Mistress. The feelings I get of silliness or that its dumb when she commands me to sit, or greet her...she is beginning to put it in terms so I start to understand why it's my place to do those things. I suppose it started out as a joke in our morning conversation, I was chatting with Mistress B on Fetlife and we were discussing vanilla headaches, one thing was jobs. I made a joke and stated she should has aspiring Femdoms pay her to whip her slaves into shape. Well little did I know her and Mistress were talking at the same time, and they were also texting. This became evident when Mistress B told me to ask my Mistress if it was ok if we texted, My mistress quickly agreed. The conversations were about me fears, how I'm hard headed and being resistant to this process. Earlier my Mistress had text me and told me she had been thinking about it, and believed it would be in both of our best interest if she let Mistress B do exactly what I joked about..."whip me into shape". Yet my Mistress added a few words which caught my eye "I'm going to send you..." and "for a few days...." to the statement. "Are you actually going to send me to another Dominant for an entire weekend?" I asked.  "Yes actually...I am, you have no choice." I was terrified, and my mind began racing with a million questions about what ifs and hows that going to work, what am I going to do, what is she going to do to me? I made the mistake of directing some of these questions to Mistress B, she told me it wasn't my place to know. Through the conversation she assured me I would leave a much better sub, and much more submissive. She talked about how when she sends me back, I would behave properly for my Mistress by the time she was threw with me. I got nervous, worried, and began trying to top from the bottom with my Mistress...its clear my Mistress has made up her mind on this, I'll be going to Mistress B's. Though Mistress is concerned that our schedules will not align soon, and for personal reasons the initial visit needs to take place in the next three weeks. I know I will benefit from my stay under her control, because she's be so stern, consistent, and directive today just through text! When she text me she told me when addressing her through text I must address her as Ma'am in each one, and for everytime I didn't she was going to spank me when I arrived. She's been keeping count consistently for each violation. She also told me how I need to address my Mistress, and I'm sure she will want a violations count from her. For the first few days its 1 hit for each violation, then it moves to 10. I noticed, since I KNEW she was keeping count, I made it a point to address properly. I think she has the mindset Mistress wants, and I know shes going to teach her a lot and I'm very thankful for that. My mindset has changed completely from my fears. I know it will be beneficial for me to go, I know she can drive submission into me and return me to my Mistress with the right attitude and outlook I need to have. I love my Mistress dearly, I'd do anything to make her happy, and if that means spending a weekend under strict control...I'm glad to do it. 

Debbie

Hypnosis, Thoughts, and one tired sub

One thing I forgot to mention yesterday was Mistress caught me in boxers, stupid mistake. I put them on when I went to go see friends since I was wearing basketball shorts; not wanting to flaunt my white and black thong I chose an old pair of boxers. I told myself to remove them when I got back home, and I forgot. Which was why she reddened my ass so bad yesterday, and it put her in a very aggressive mood for the remainder of the evening. Awakening this morning she was not happy I hadn't "messed" my diaper, despite the fact it was soaked through and through. "I think it's time for you to go into diapers 24/7, its the only way your going to become fully dependent on them" she said as she woke.  Shuttering that thought away I found myself reflecting on something she stated last night, which kind of bugged me. I don't want to be her cuckold, yet I feel in time its inevitable and the signs are painted on the wall; A.) "your not going to have sex with me again"  B.) "your going to be sleeping in a crib every night, not next to me anymore" C.) Her making me suck her strap-on and progressively training my hole to take larger dildos and plugs.  D.) Her wanting a milking machine so she wont risk me feeling pleasure during a monthly milking. E.) "soon your cage isn't coming off anymore, your going to have to learn to wear it and your diaper" F.) When I was pleasuring her with the strap on she said "its just not the same as the real thing, sorry but you can stop". And Lastly what she said last night "I need to get you an isolation hood and a mask, I have to stop viewing you as my boyfriend and start seeing you as my slave, the mask will move this along much faster".  I felt hurt, worried, and concerned why she doesn't want to see me as her boyfriend. When I repeated it back to her she said that wasn't what she meant. But that reply did not satisfy me, and reminded me of when Mobico asked his wife the proverbial question "Do you view me as your husband or your slave?". I over think everything and I know I just need to sit back and ride this train, after all it was I who introduced her to chastity, I just never thought we'd come this far, and we still have along way to go. I know hundreds of guys out there would KILL to be in my shoes, but it's not all fun and games. Though I did notice I'm not as horny today, I think I may of had a wet dream since my balls no longer ache, guess I need to check the diaper.

None of this, this evening.

She is wanting alot of new items, so I asked her to prioritize them for me last night and she said she wanted the crib within the week, then the hood, then a highchair, then the machine, then the maxcita straight jacket. To me this sounds like a cocktail for a miserable slave!  Add to the list the items I will be adding to surprise her with; the new corsets, jewel designer butt plug, and the steel collar I found, One she can actually leave on me full time when I'm not in public since I'm sure she's going to start leashing me soon when ever she makes me start crawling around.
When I went home for lunch I didn't eat, instead I cleaned like a mad man, or, girl? So I would have less to do this evening. It's actually 2:00pm now as I'm typing this first part of the blog, I plan on cleaning like crazy when I get home from work. Clean whole house quickly and not do it in heels, plugged, and chains? Yes please! Wonderful conversations continued today with the Mistress I referenced yesterday, I'm excited to tell Mistress that she's really nice and I think they will hit it off. Its SO NICE to be able to talk to someone about it other than Mistress's "coach" and get insight into a domme. Another local Mistress gave me permission to message her slave, I've yet to do it though.
Well It's now a little after seven, I messaged the other submissive and I think were off to a great conversation! I continued to talk with the Mistress who lives close, and she's really helped me with alot of the mental roadblocks I've put in place through this process. She's also taken alot of concern away from exposure and humiliation today. One thing she stated was she thinks I need much more hypnosis, to help continue to solidify my training and transformation; she stated it's obvious it's working on me. I truly am thankful for our long conversation today, it's nice to talk to someone who is as kind, real, and honest as she is! I thought about it and asked myself the question "If she was sitting in our living room with Mistress would you be embarrassed to serve them in your maid outfit, or her seeing Mistress do anything to you?" The answer quickly came to my head "no I wouldn't". I think the reason I feel this way is because she understands the lifestyle, and a sub missives place in the whole scheme.  Now, I don't know if that day will come where her and Mistress become close enough where she begins the visit, I hope it does but thats not what was comforting. The notion that there are others in the local community with her same outlook is comforting. "You'll never meet a group of more open minded people.." she said, and that's comforting. I've been cleaning since the minute I got home and its time to prepare dinner, be back soon!
The floors look amazing and I cooked a wonderful meal, I also made sure I welcomed Mistress properly when she got home ;)  I cleaned like I was insane this afternoon, the amount of sweat pouring off of me you would have thought I was mowing the lawn! It was SO hot for some reason. I rushed to the grocery store and got home just as Mistress was arriving. I finished dinner and we enjoyed our meal, I sat on the floor and proceeded to clean the kitchen when I was done, granted its still not clean I made a huge mess during dinner. Before I started cooking Mistress had me lay down on the bed naked, she contemplated putting me in my uniform, the opted to go ahead and diaper me for the evening and putting an apron on me for while I cooked.  I hate it when she gets home so late in the evening; I know she's unwinding from the day and the last thing she wants to do is train or think of all the rules she has to enforce. So I do understand, yet its SO FRUSTRATING when Im on these long chastity stints; because I feel like we've only had one day of solid training and involvement since my business trip got in the way earlier this week. The only reason I harp on wanting her to be consistent and to start enforworth it. When she's consistent and I go into "sub space" then I don't think about chastity, getting off no longer matters, all that matters is pleasing her and making her happy. I want that to be constant! And I know it can, and I know in time it will. I just have to be patient, on the day I make enough money to tell her to quit her job, I will cry tears of joy because she truly does work so hard and is underpaid just as many people are in this economy. Any ways after I cleaned the kitchen she was in the bedroom setting up the restraints for a hypnosis section. She hadn't done one in awhile, but before leaving the room she took the gag and made a new hole in the belt "Since you like to try and spit this out, I'm going to make it to where you can't even get it out of your mouth" was all she said as she tightened the ball gag to a painful tension. My mouth still hurts like hell. For two hours I listened to hypnosis files, I laid there and hoped a certain file would come on, "chasstity" is it's title, it takes me to such a happy place and I feel it has made the biggest impact on me, yet it never came. I tried to tell her before she started and she just walked away. I came out of my trance and didn't say a word as she turned on the lights and removed my restraints and blind fold. It was a very interesting vibe I was feeling. I didn't want to move, I didn't want to sleep I just wanted to stay there. Even after I got up I didn't shake this feeling until about thirty minutes later, and it left me overly tired. My limbs are aching from the chains, she pulled them as tight as she could. Need to get some rest, not sure if tomorrow will be full of fun or not. I suppose we'll see!
cing all of the rules, being strict and never breaking her role (though I know when that day does come I will want these days back) is that it makes the massive waves of frustration that chastity is bringing to my mind every minute

Milking Machine?! Really?!

The machine (clip from video which inspired her)

Another busy day with vanilla life, work was hell and it ended even worse than the entire day. I made a huge mistake which was all my fault, and it caused no damage to anyone other than my own sanity. I was furious I let my guard down on a task and it's going to make for a terrible day tomorrow, and a crazy busy one at that. I had many errands to do once I arrived home, I looked for a note from Mistress and could not find one so I mowed the lawn and took care of a few things. This morning I awoke with a very messy diaper from multiple sources, I told her it was messy in shame, she smiled through her sleep as she changed me and grabbed a white and black thong for me to wear as she clicked my chastity device on. Back to this afternoon, she arrived home around 8:00pm and I cooked dinner as she vanished to work on a project for a client due tomorrow. She didn't put me in my outfit, diaper me, train, hypnosis, bondage, none of that. I was relieved and sad all at the same time, a strange feeling. Yet I think it's relevant; Im so much more submissive and in my role when she's consistently strict; yet life has a way of creeping in. It still feels "dumb" when she tells me to kneel, or blurts out a position when she hasn't trained in four days. Or we haven't done anything in four days, which I know will change. I just hope it comes soon for my sake, it makes this process so much easier. I cooked dinner yet it turned out awful, I barley ate it...Im normally a good cook, I take pride in that, but I was off my game tonight. After dinner I crawled in bed and had a wonderful conversation with another Mistress who lives a few hours from us, it was really nice to be able to talk to someone about my

Slaves in a funnel gag, she pours his cum back into him as it comes out...

feelings and get her point of view. As you can tell I was lazy today, I didn't clean really, cooked a terrible meal, and did none of the things she told me a week ago she wanted me to do daily. When she realized this she gave me a terrible spanking, and the only reason she stopped was her hand was hurting her (good thing she didn't grab the spoon). She lectured me on how bad I was, and said it ended tomorrow and we go back into full mode. I hope she's right, I need it if Im going to be better at this. Mistress also began discussions with several other female dominants in our area, so it's nice to know she will soon have friends.
When she laid me down to diaper me she turned me over again and spanked me, during this she told me to explain the machine (her coach messaged me this morning and tasked me to help her find out what machine this certain Mistress was using to automatically milk her slave). I found out it was a special medical device, and she ordered one. My Mistress stated she thought it was a good idea to go ahead and purchase one, so I plan on it this weekend. Im so horny right now I wish we had it! I hope I have more to say tomorrow! Good Night

Debbie

The awakening of Mistress

I.am.exhausted. Reading back over Mobicos tale The Real Feeling of Chastity I understand why he was always saying he was so exhausted. Why he struggled to post on a daily basis, or even a few times a week since he learned to value sleep more than anything. If today was any indication of how my schedules will be in the future, I too am going to learn to value sleep deeply. Today started out as any other, with the exception of Mistress having the day off. I arrived home a little after four from a busy day at the office. She was outside on the phone so there was no greeting her, when she came in she told me I had one hour starting now which was "Debbies time" and then I was hers. I didn't eat lunch so I decided to cook some food and eat, which took up all of my hour. I could tell she was acting different, a little more assertive and confident when she told me to read over a sheet of paper laden with notes she had written. They were some general "house keeping rules" on what she now expects, along with some instructions for the day. She also had another stack she told me not to touch, there were alot of notes and it was clear she had been very busy today. She stated she spent the whole day preparing, researching and making plans for me. She told me to strip and lay down on the bed, she disappeared into the bathroom and told me to stand in the tub. "It's time to make sissy smooth again" applying Veet to my entire legs and ass. She paid much more attention this time and within twenty minutes my leg hair was gone. Rubbing lotion over my newly smooth skin she admired her work and smiled, by the way I was gagged the whole time, she gagged me as soon as my hour was up. Half way through the hair removal process she removed my gag shoved a dildo in my mouth and told me to suck on it while she finished...this was new.
When she was finished she began to dress me in my maid attire, stating how she would be making me a much fluffier more sissy like petticoat for my uniform, she wants my ass exposed the entire time apparently. Instead of a diaper she put on my red ruffled panties, thigh highs and my tall heels completed my uniform, so I thought. "Are you ready to look pretty?" she said, leading me into the bathroom she sat me on the toilet and shaved my face from the days growth. Then came a huge shock...she got out her make up boxes...this can't be happening. For the next twenty minutes she loaded my face up with various eye liners, foundation, mascara, things I had no clue what they were, and finished with bright red lipsticks. "Your going to make a beautiful girl, you look great" she said laughing. I looked in the mirror and was shocked at what I saw...It didn't look like "me". Yet she wasn't done with her art project, she then sat a red long wig atop my head, tucking in my hair. "I look like reba on meth" I said, I got the gag again. Then she led me to the living room, where the next phase of the night began. "It's time for you to take this seriously, no more laughing at my commands, were starting training now, and we will do these commands for weeks, or months, however long it takes you to do them perfect". I suppose she's not kidding. The first command she told me was simple, so I thought..."kneel". I knelt on the ground in front of her and she corrected me. "Knees together, toes pointed back, ass on heels, back straight, neck straight, chin level with ground, fingers together, hands on thighs pointed towards your knees".   Well...damn, this isn't simple. We did "kneel" twenty times. Each time her having me stand up and do it again. Next was "Punishment position" which was "Knees on the ground, shoulder width apart, face on the floor, hands over my head, dress and petticoat pulled up exposing me ass, wait for punishment". Then came "worship" same as kneel except my arms stretched out, face on ground, touching her feet. Then came "Corner" which was me standing in designated corner, nose to the wall, hands behind back, straight as an arrow, feet together. Followed by "Slut" which was the same as punishment position except on the bed, panties down. The spread eagle which meant for me to lay on the bed limbs spread to the corners. "Crawl" was me crawling making sure to shake my ass as hard as I could with each movement forward, more walking instructions....and I was beat. We did each move over and over, she would slap me with her crop for things not being perfect. "You did surprisingly great sissy, good job".
I then served her dinner, sitting on the floor beside her eating my own meal, the break did not last long. She had me clean the bathroom, kitchen and fold a monstrous pile of clean clothes, 3-4 loads. When then ran to the store to pick up a few things, she removed my outfit of course. And lectured me on my ride how the excuses and back talk must stop, which is why I would be gagged when she is home from now on. When we returned I was looking forward to laying down and relaxing for the evening, I did not want to do anything to make her mad since things seemed to be going well. My expectations of relaxation were wrong. She told me it was diaper time, removing my chastity device and diapering me led to the next phase of this oh so long day. Rope bondage, she kept talking about how she was to deploy bondage on a more regular basis, so she practiced various knots on me. We watched some tutorial videos and I helped her start building her rope skills. "It's ten o'clock, we have to lay down now" I thought inside my head. Nope. I was wrong.
Laying in a wet diaper she said it was time to take the diaper off. "But why?" I asked, lesson I need to learn...stop asking questions. Once I was naked she returned from the bathroom with my night mare...the biggest strap on we have hanging between her legs. "No, please, no...not that one" I pleaded. "Your going to learn to love this one, then we'll get a bigger one! It's four times the size of you!" I was scared. She crawled on top of me and began making me suck on the large dildo, gagging me as she laughed.
At that point I wish she had taken anal training more seriously so my hole would be more prepared. Cuffing my ankles to the spreader bar, she began to enter me as I moaned in pain. This dildo is huge, 8 inches long and very thick, She barley got it in and could tell I wasn't ready. She ripped it out and returned wearing the 6 inch long normal dildo. "You like this one, and your going to love the other one soon sissy, your going to love cock in your ass". For the next twenty minutes she fucked me non stop, my waves of exhaustion were inhibiting me from enjoying this. I just wanted it to end. By the end of it I knew I was loose, I could have taken the big one I imagine. She returned and slid the clammy cold wet diaper back under me taping it on and returning my plastic panties over it. "Good job today Sissy, you did good".
I'm not sure what got into her, but it seems she has awakened, and I'm wishing it would't of happened so soon. She told me to give her the list
of other Mistresses in our area tonight so she could find other female dominants. The night was a blur, she did so much to me, I was moving constantly and all I know is my feet are killing me from the heels, my hole is sore, and I do not like make up. At least I'm laying in bed. She keeps mentioning making my night time diapers more absorbent "They leaked out the side while she was changing me this morning before work". I don't know why I keep using my diapers so much. I can't sleep without them. Im actually packing for a business trip and I'm taking one for each night.  Im scared at what tomorrow will bring, but I promise you I'll update daily as long as people continue to comment on my post and follow my blog. It takes alot out of me at the end of a long day to type these long entries, but I want to fill a void and provide a view into the world of FLR, chastity and sissification for those of you longing for a Mistress of your own, and those fortunate enough to relate. Thanks for reading, it means alot.

One tired Sissy,

Good night.

Heels hurt!

A very long day at work, was made even longer due to my lack of sleep last night. My sleep deprivation was not brought on by any evil doing of Mistress, rather the animals were making alot of noise. Between the symphony of the cat and the annoyance from the dog sleep was not in my forecast. It did not help receiving a text after I left the house telling me to be in my outfit cleaning when I got home, I knew I was going to be exhausted and the only thing I wanted to do was sleep. After an eight hour meeting of site I returned to my office around 3:30 in the afternoon. Thankfully my boss walked in and told me to head home, since my whole team had a long day. Im in consulting, I'll leave it at that. When I got home I could not sleep, I just wanted a nap, but sleep would not come. A friend called and asked me to help him out, and tired as I was you can't ignore bestfriends, you'd want them to do the same.

When I returned Mistress had already arrived home, she told me to shower so she could get me dressed, and to not use the toilet. Well...I had to go, so I went ahead and "thought" I got it out of my system. After scrubbing away she walked into the bedroom and told me to lay down. Chastity device came off, after flicking my stuff for a few minutes she handed me a fleet suppository and said "Put it in, go ahead." Once I was diapered she proceeded to put me in my uniform; thigh high fishnets, garter belt, three overly fluffy petticoats, my maids skirt, apron, the new corset like top she got me and finished it with with the 6 inch heels. "You really do look good, by the way". She said with a smirk, she could not stop smiling. I suppose it's a good thing I'm in shape. Im not one of those over weight guys running around in a skirt trying to look dainty, thats simply ridiculous, find a treadmill, ok I'm off my soap box. I proceeded to clean the house while Mistress ran an errand, though she was back surprisingly quick (good thing I behaved). About that time I felt a pain in my lower gut, and with that the diaper became quite full. I also noticed it was very wet, and I didn't recall going, I suppose it's becoming ingrained to just go. While I was cleaning I was also preparing dinner while Mistress did her nails on the couch. "Your getting really good at walking in your heels! Good Job!" she stated. I grumbled under my breath, and continued scrubbing away. I served her dinner and joined her on the couch...odd I thought she's not saying anything, it seems the small things still aren't being enforced unless I tease her how she's forgetting them. Though she hasn't spanked me in a week I thing (something she said would be daily) hasn't broken out the strap on in awhile (something she said would be daily) and hasn't done a whole lot of bondage other than chaining me to the bed (something she said would be daily.) Im sure it will kick in soon. After dinner she told me to go clean the kitchen, after struggling through due to the pain in my feet and the horridness of walking around in your own filth I sat next to her and said it was done. "Lets get you changed for bed"    Dreams do come true!   I was so excited to get a fresh diaper, I didn't care she was putting me in another one, I just wanted this one off. Laying me on the bed she told me to put my ass up and she began taking pictures, then came the change. It's still embarrassing but only when I mess, I think its gross she wants to change me, I know its only to humiliate me. She really needs a changing table, we'd use it like crazy. Once I was freshly diapered she had me do a few more small chores then I broke away and worked on something I wanted to do, which was nice. Sadly though I wet as soon as she put the new one on, and I'm trying really hard not to "go again"...she can tell, and keeps laughing about it. Apparently she's going to start making me another outfit, and purchase more babyish plastic panties, it seems shes begun to embrace "regressing" me when she wanted no part in that at first. Oh well, whats another thing to be subjected to? No files today though! Yay!  I know I said I would post the links tonight, but I must rest, so I apologize, I will tomorrow, I promise. 

Sweet dreams, hoping for a wet one, Im getting horny again....

Debbie

Working out the "Kinks"

One of the most important things in my eyes through this process is the ability to be able to discuss things, just as we were able to before diving head first into this lifestyle. I believe that is going to be pivotal to our success. Work has been rather busy this week, for Mistress and myself, after arriving home from work yesterday I was very edgy, and simply wanted to get my chores done and go meet up with a good friend. She had a client coming over (no, she's not an escort, its her little business pertaining to clothes) and had to rush to make some last minute changes to the garment. Well after going and seeing my friend and coming home and finishing the yard work, I was about as wore out as you could be and had a few things on my mind. While my shower warmed I asked her to please sit down on the bed so we could talk...I asked more than a dozen times and it ended with her getting frustrated and angry, for no apparent reason. Stress is something I have learned to cut out from my life, and I'm a much happier person because of it and I'm trying to teach her those skills.
Mistress leads a busy life, both in and out of the home. By the end of the day small things can set her off...and I'm normally her target. This is not something new, it almost led to our undoing over a year ago. And I hate seeing her so stressed, not because she takes it out on me, but because I love her to death and stress is something avoidable if you know how to handle it. Stressing takes years off your life; it's proven! So I've been trying to help her cope with it and remove it from her life all together, last night I think we had a big break through, and I fully think it's going to help her out in all aspects of her life, not simply chastity. After I took a shower I sat on the couch and ate dinner, and told her what I wanted to talk to her about was very serious, and wasn't something I wanted to wait for. "If I tell you I truly need to talk to you, it's important". Her demeanor changed and I could tell she knew I was serious. We discussed why she gets so mad, and how to deal with it. She's more focused on trying to figure out what is stressing her than just not worrying about those things in the first place. The conversation was a good one, one which I'm glad we had. We discussed her not taking out problems and vanilla stresses on me via the lifestyle, and how that was a huge red flag, ultimately she understood where I was coming from and agreed. There was no training or play other than being diapered before bed, as always. And that was ok by me, these "kinks" are important to work out and it's best to get them out of the way now. Just as in anything, building a foundation is the most important thing we can do right now.
On a side note I think I may have had a "wet dream" not sure, haven't had one in over 10 years. But when I woke up the other morning, things felt, well sticky and I had lost all my horniness...which is somewhat sad since the build up is the only thing which drives me to be better.
She told me to be in my maids outfit when she gets home, I have some chores I need to do and some work outside which is not planned. I'm going to text her and let her know I plan on working on the back yard, so if I'm not in uniform it's because I'm out back making our weekend easier.

Will update this evening before bed.

Deb

The beginning of another week!

Finally back in town as of late yesterday evening! I made a trip to see some family members on Sunday and Saturday the house was full of family members helping us continue our restoration efforts. It was not a very "FLR" weekend to say the least, which was fine by me since I didn't particularly enjoy the "training" session we had last week, and apparently Mistress is buying my first set of heels this week, the first of many to be added to my closet I fear. I wanted to take the time to update you and relay a conversation I had today with Mistress's mentor, as well as fulfill the request she asked of me. Last week Mistress shaved my legs and ass for the first time, my ass has finally cleared up of the proverbial red bumps, but my legs are still on fire! It seems new bumps surface every day, to clarify it was Veet, not a razor. I don't like the thought of being hairless from the neck down, but I understand why it must happen...so if it must happen I want it to be done right, and smooth after. I suppose if the goal is to get me to feel "feminine", it's defiantly not going to happen if my legs are covered in razor burn. I think we're going to have to figure out a way to remove my hair and not irritate my skin. I know it can be done, it's simply going to take time to figure out how to do it properly. My hair is pretty thick, so removing it is a challenge.

I have a feeling it will be something along
the  lines like this.

"No one can tell, I Promise."

On another note, I may need thicker diapers, or a booster pad at nights. I've never had this problem before, the Abriform's have always held anything I have put in them, but I'm finding myself flooding them at night. From the moment I lay down until I get changed in the morning I normally wet them three times. Yet it seems I am wetting them much more than normal as of late; not sure what this means. I noticed it Sunday morning when I woke up, I got up and started wetting them again, and pee was running down my leg?! Today the same thing happened. Luckily I was standing up and not in bed (Mistress would have put me in them 24/7 if I got the bed wet). I feel like I am "use" to them, when I'm wearing them I don't even think about going, I simply just "go"... which freaks me out in some ways. In other ways it makes me realize even though there haven't been a lot of major changes yet; they are coming...and perhaps some of the biggest changes to be made will slowly happen over time. My biggest fear of all is when I am forced to make the switch to 24/7 and having to wear them under my clothes in public. I just know Mistress will make sure my shirt rides high when that happens and my pants fit tight, since the bulk of the diaper pushes your pants slightly down; it greatly increases your odds of being noticed. I think that will be her goal, and I have full faith she will make sure they are extra thick, so my waddle is just right. I have this slight feeling public diaper humiliation will be on my agenda many times before the end of the year. Thought I believe at that point I won't fight it and will simply except it if Mistress continues training aggressively. The thought of being seen like that makes my heart pump rather fast, I have a feeling my cheeks would be red the entire time, or will be red! The thought of public exposure, or any exposure makes me nervous, and it's something I've thought about alot actually. I know it's only a matter of time before it happens but I want certain things to fall in place before it does; I want training to be much more constant so I'm in a much more submissive state of mind, I want the "transformation" to be much further along so I've begun to accept my new role. We'll see if that happens, consistency is going to be key, not sure if consistency will be consistent enough. Only time will tell!

In regards to the conversation I wanted to tell you about, it was with Mistress's mentor, Amy. Mistress found Amy on chastitymansion.com through my thread in the Vault section. Amy is a seasoned veteran when it comes to the world of chastity, forced feminization, and diaper humiliation. She's been leading a FLR with her husband for over five years, not to mention she's only 28! Which makes her much more relatable to Mistress and myself since she's only a few years older. Her and Mistress were inseparable in the beginning, and their conversations would go on for weeks it seemed. Well she sent me a chat today when I got home from work and it began simple enough with her checking in since she said she had not talked to Mistress in several days. Mistress does not log into the mansion on a daily basis, unlike myself. She asked me how things were going, I sought refuge through her during the beginning phases of this process, I needed someone to talk to about my concerns and she was happy to keep our conversations to herself. Mistress does know we talk and is happy that I have a means to vent and get rid of my concerns. Amy has been a huge help to me, and may be the only reason Mistress has the confidence this time to succeed. She truly does have a wonderful heart and has given me tons of advice, such as "If your Mistress ever uses the lifestyle against you when she's angry over something vanilla, huge red flag, if she ever punishes you because she's stressed or angry about her work day, huge red flag. This is for the safety of your relationship. It's not fair for her to ever take anger out on you through this lifestyle, that's not what this is about!" When she told me that I knew she had our best interest at heart, I'm not sure if she's told Mistress that but I feel that's something very important to remember. 

Max Cita, if my ass looked like that
I might be more receptive to this
process!

Following my update that everything was fine we we're simply busy, she informed me she needed to give Mistress some notes and asked me if I was excited about getting my own Max Cita (straight jacket, a very constricting one it looks like). Mistress has brought this up many times, I know she want's one and as much as she's talked to me about it and showed me pictures...I'm starting to want one! I think it's a tool she will use regularly, and it looks rather fun!

Now that I've given you a small introduction on who Mistress's mentor is, I will tell you about our conversation. She asked if I had any current concerns, which led into a conversation about feminization and slowly transforming into a true "sissy". "Are you enjoying the strap on?" was one of the first questions she asked, I told her I wasn't yet she assured me in time I would beg Mistress for it and assured me in due time it would be my only means of actual "sex". She also asked if Mistress what emotions I felt when I had to suck Mistress's strap on, that freaked me out! "Whats the point in sucking a dildo?" She told me I needed the practice, well safe to say Mistress has not done that yet, it hasn't come anywhere near my mouth!  We also discussed my fear of public exposure, especially with diapers. She told me her sissy "Jenny" loves going out in public diapered now, and that once my feminization progresses it will be much easier, and I think I agree with that. "Once your body becomes smooth as silk, your skin is a glowing tan, your corset as giving you the perfect curve and you see yourself in the mirror with a beautiful wig and make up, I think then you will see this is truly your place...you want to look beautiful, not ridiculous". Perhaps she's right, though I think my Mistress has alot of work today before that point, as do I. Lastly she told me she sent Mistress some inspiration, which she asked for. Not entirely sure what that means yet, though I do hope the consistency picks back up (flash backs to last time), so that if we are going to do this, it gets done right. I meant to post this last night, it's now Tuesday morning. Will update tonight after training, if we have any.

Let the training begin.

I suppose in a few months I may find myself saying the events of today were normal, yet I'm still adjusting and still trying to take these changes serious. Example: when she tells me to call her Mistress, I smile when I say it, or get the urge to laugh...she does not. I came home from work today for lunch, and she had a rare week day off, normally like me she is only off on the weekends. I work close to home so I will normally come home for lunch. When I arrived she had lunch ready, which was wonderful...while eating she stated she needed to get my measurements. Mistress is very talented when it comes to design and sewing, making clothes is actually a hobby of hers. What I would find out at the end of the day when I arrived home would be just what she was making. On my way home I received a text from her stating "Your list of chores is in the Kitchen, your outfit's on the bed...see you tonight." Harmless enough right? The note was simple "Debbies Chores: Mow the Lawn, put on your sissy maid outfit, ankle cuffs (lock them), wrist cuffs, gag, then detail the Kitchen counters, clean out the fridge, clean the stove and oven, then proceed with the wood work in the house". (Doing some updating to our home).
After laying down and attempting to take a nap, which I am permitted, she knows I work hard during the day. I proceeded to go about the list, except I made one modification, I didn't lock the ankle cuffs on. She promised me she would be home around seven, when seven forty five rolled around and I had nothing to do; I removed my outfit and proceeded to put on work clothes so I could tackle the wood work which has to be done by Saturday before the painters arrive. Im a very timely person, its a small pet peeve of mine but when some one tells me a time, I expect them to be there. It's not that I wanted to disobey her, I just knew we had priorities to take care of. When she arrived home she asked the obvious question "wheres your outfit?" After explaining she too agreed we needed to get the wood work prepped and out of the way. Once finished she asked if I was ready for the evening, which I was so we proceeded to the bedroom. "Lets get you in your outfit" she stated. Wanting to admire her handy work for herself she quickly slid on a pair of red ruffled panties over my butt, followed by thigh highs, garter, white elbow gloves, a mock corset, then TWO petticoats, followed by the black maids skirt she had worked on all day, trimmed with white lace. An apron was tied on, my cuffs were locked too me. One would think I was ready; not hardly...the posture collar was put into place followed by the beloved ball gag...the joys of life. "You look so adorable...seriously, you look like a girl." she said with a huge smile on her face...she quickly hustled to her closet where she retrieved a blonde shoulder length wig. After some light protest on my part she got the wig situated. She stepped back, smiled and didn't say a word. Her face shown with approval and mine with the "this is ridiculous" look.
Sitting me on the end of the bed she slipped on a tall pair of heels, "Your training begins today, I want you to watch me and then mimic what I do." She has not bought me heels yet, its on the agenda, she paraded around the living room shaking her ass aggressively as she walked... "Your turn". Next was how to greet her when she arrives home, we repeated it over and over and over... Kneel, kiss her hand, kiss her foot, Ask her how her day was with her proper title, stand in attention ready for service". After she felt I got the hang of it, she moved on the crawling. I truly didn't think she was serious about this, she attached a leash to the chain between my legs and told me to crawl in front of her "Only sissies crawl and shake their ass, shake your ass more, More, MORE, MORE!" She made me crawl around the house for almost 15 minutes. "Do I need to get your diaper on you? will that help your ass waddle better? Crawl now!" Once this FINALLY ended she made me crawl to the bedroom. Laying me face down, chaining me to the bed, blind fold on and headphones plugged in. You guessed it...more hypnosis files on how my only pleasure is to come from a strap on. Twenty minutes into the file she flipped me over, pulled me to the end of the bed and began playing with a vibrator around my hole. Granted it's only been a week since my last orgasm, I was horny as hell. She removed my chastity device and began teasing me. Working the vibrator in and out, then she placed a large plug in me, I moaned in pain. When she returned she was wearing her strap on, and proceeded to fuck me for the next 30 minutes. It was more painful this time, more than likely due to the fact I'm still sore from the pounding she gave me a few nights ago. When she was done she laid me back on the bed, crawled onto me and sat on my face looking towards my feet. "You've been good, I know your horny... you get a ruined orgasm, now I've never done this, so when you are getting off let me know and I'll let go". I agreed and she continued to stroke me, It didn't take long for me to get to the edge...when I felt it going I muffled into her panties, she let go. Im not sure if she did it wrong...but it felt pretty good to me. (Ssshhh, don't tell). Into the shower together then into my Diaper, as I write this I remembered...I forgot to eat! Oh well, now I'm going to lay down in the comfy bed, and enjoy it while I can.

Debbie

Learning my place in the relationship

Monday morning had arrived and my diaper was full, Mistress was very pleased as she removed it and put my chastity device back on for the day. “Good boy” she cooed again, “Im very proud of you, you need to do that everytime your in your diaper, soon you won’t be using toilets anymore once I figure out what kind of daytime diaper to buy for you so you can wear them to work”.  Well that’s some great news to start your day huh? She told me she would be home around five, left me no specific instructions other than I had to plug myself as soon as I go home, and keep it in until she took it out.  I got home a few hours before she did, plugged myself with the medium plug and laid down to take

a nap with my panties holding it in place (she threw away all of my boxers). I woke up an hour later with the strange urge to want to make her proud; I quickly cleaned the whole house then returned to her bathroom. Suddenly I got the idea of wanting to make her proud again, so I attempted to plug myself with her largest plug to better prepare my “hole”. I had no luck getting it in, so I began to look at other ways to get ready. She had made it pretty obvious she would be “fucking me” tonight, I knew even though I hated being plugged, it would make sex a lot easier for me…the lesser of two evils? She had told me get out her largest dildo for her harness “King Kong” is its nick name. It’s 7 inches long and a few inches around, it’s a really good size, though I know she’ll be getting larger ones as my training progresses. I attempted to stick King Kong inside me to see how bad it hurt; pretty bad was the outcome, though I knew I would survive.

When she got home she immediately checked to make sure I was plugged, satisfied we sat down and ate dinner, which followed by a surprise for me. She led me into the bathroom and explained it was time for me to lose all of my body hair. I literally got sick at the thought, I’m a guy, my legs have hair…my chest has hair…my ass, well you get the pattern. She then covered everything in Veet, I couldn’t believe she was making me hairless! It didn’t really hit me until she began scraping it off with the tool. What lied underneath was smooth skin, for the first time in my remembering life. I was shocked. “Sissies aren’t hairy, you have to be sexy, your arm pits are soon”. I really couldn’t comment much, I think this really hit me that she was very serious about feminizing me as much as she could. She had joked about getting me fake silicone breast which glue on, I never took those comments serious until now. “You’ve always had a great ass, but damn it looks good now”. She continued to compliment her work. I looked at my reflection in the mirror “From the back down, from behind you look like a freaking girl!” I thought silently to myself, you have no hair, your wearing a thong, your ass is showing off a pink plug…what have you gotten yourself into.

“You look so sexy, get on the bed now” she firmly stated. After applying lotion to my new skin, she attached my ankle cuffs to a small 14inch spreader bar, then attached my cuffed wrist to the middle of the bar; I was laying on my back “Hog tied” if you will. Wrapping her hands around my thighs she pulled to the edge of the bed, so she could have full access to her “sissy hole” as she continued to call it.” Removing the plug she blind folded me and asked if I was ready. Explaining how she was not going to gag me this time because she may want some of my feedback. Looking back I wish she would have. She positioned herself in front of my rear, I could hear the lube spreading before she entered me. I realized she wasn’t using “King Kong” rather a smaller dildo, about the size of my actual cock. I failed to mention she removed the chastity device as well.

About two minutes into her being inside me, she began to pick up the pace, and all the while grabbing my cock and stroking me rhythmically while she continued to pound me. I was lost in a see of pleasure, it began to feel so good, I didn’t understand the feelings. Granted I’m horny as all get out despite the fact its only been five days. She continued, “Does this feel good”

“Uh…huh” was all I could stumble to get out.

“Do you want to get off?”

“Yes please” I said.

“Do you like me fucking you”

“Yes I do, can I please get off??!!”

“No.” she said calmy.

Then I made my fatal mistake, I tried to top from the bottom…a big no no. I started begging for anything, even a ruined orgasm. She poured more lube on my cock and got a little too much; she noticed it but I made the mistake of telling her she messed up. Right there she pulled out of me, said alright that’s enough… “You just couldn’t shut up and now it cost you, into the shower, then into your diaper and off to bed”.

I was so freaking mad! Then it started to hit me “You just got made because she wouldn’t jack you off while SHE was fucking YOU”. “That felt somewhat good???” What’s happening to me?

Tuesday was uneventful, typical chores and hypnosis files followed by another evening of me in a soggy diaper. Falling asleep with my face in her ass (which I don’t mind, she has a perfect ass, I mean perfect) she reminded me to plug myself when I get home Wednesday afternoon. I know she’s going to get the strap on out again. I just can’t grasp…am I looking forward to it? Or dreading it? We’ll see tonight…

Sissy Debbie

Isolation Punishment, reality setting in

First, let me apologize for the horrid format of the last post! I could not for the life of me figure out how to change the font on the later section! Though I hope the last post provided you with some background. This is will be the last post in journal form and will catch you up to speed on the past week.

Thursday night I knew she was serious about beginning again, her first words when she got home were “lets get your diaper on you”. She told me we were going to start promptly on Friday (the next day) and I would be “busy” until Saturday during the day at some point. Friday was a terrible long day for me at work, my mind raced to make sense of what she was going to do, or even think of what she was going to do. I received a text during the day stating “I need you to finish your room when you get home, install the I-bolts where I instructed you. Take a shower and be waiting for me.”

Let me explain what she means by “my room”. Inside of her bathroom closet, there is a small crawl space which is about 3 feet high, 3 feet wide, 3 ½ feet deep. Just big enough for me to sit in, or curl up in a little ball. At all four corners of this “box” at I bolts and mounting rings (eight in total) four up top and four down low. She placed a 1inch thick piece of foam on the floor as padding, and we added a wooden door which literally “seals” when its shut. The door has 3 different locks on it and 9 one inch holes for “fresh air”. She’s always loved the little room, and joked about keeping me in there ever since we first looked at the house.

When she arrived home she told me I would be in Isolation for the next 15 hours, my heart literally sank. She had mentioned it the night before, but now it was obvious she was serious. “Lets go get you ready”. Was the only thing she stated upon arriving home. I was then led to the bedroom where she removed my clothes leaving me standing there in nothing but my Mature Metal Jail Bird waiting for her to return. When she did she attached her newly bought locking leather ankle and wrist cuffs, locking each one with its own pad lock. Then she removed my chastity device and laid me on the bed “You wont be able to touch yourself, even if you try” she proclaimed with a confident smile. And she was right; Laying on the bed she applied a lot of baby powder, much more than normal as she explained to me I probably would be in this same diaper for the next 18 hours. After taping on one Abena Abriform M4 X Plus (this one of the thickest adult diapers) she made long slits in it, a puzzling action. She then produced another Abriform and placed it over the one already wrapped around my waist. After slidding on pink plastic panties she gave me a rather evil smile stating “Trust me, your going to need all this”. And with that she quickly gagged me with her locking ball gag and led me to the kitchen while I waddled behind her. Sitting me down on the stool she then proceeded to explain the rules of the evening, the normal “no complaining or it’s going to be worse” mantra while she prepared my dinner; baby food.

I don’t like vegetables that much, I never have, I don’t care for them much pulverized either. She laced everything she fed me with laxatives; yogurt, bottles of milk, water, 3 different types of babyfood… she fed me until I truly felt like I was going to explode. I failed to mention she inserted two Fleet suppositories in me while she was diapering me. Then I was led to my room, chaining my hands and feet to the four points and securing each point with its own master lock, I knew I wasn’t going anywhere on my own. Upon locking my gag in she produced head phones; which caught me by surprise. “I told you I’d keep you entertained” she smiled.

What would pour from them would be my new hell; two hours of diaper/sissy regression hypnosis followed by Keyholders Binding on repeat by Elena at esuccubus.com. I was in a terrible trance, drooling because of the gag, flooding my diaper every ten minutes it seemed, this box scared me; her tactics seemed to be working. A few hours in she opened the box to check on me ( I was blind folded despite the fact no light comes into my room). I was overheating, couldn’t breathe, and pouring sweat. So she opened the door and placed a fan in front of me, and the hypnosis files kept playing over and over, I lost all perception of time.

After five hours she un chained me and let me out of the box to stretch, drink, smoke a few cigarettes (which was very wonderful of her). All I knew was I hated the box, I thought I was going to die in there! I still hadn’t produced a mess in my diaper, which upset her too the max, after explaining I hadn’t eaten that day she took me to a fast food restaurant (still in the worlds thickest diapers) to get dinner. Once we returned we watched TV and ate, I was happy to be out. She then told me to strip and lay on the bed, upon walking in the room I noticed she had attached chains at each corner of our, excuse me….her King size bed. She strapped me to the bed using a spreader bar; in went the gag, on went the blindfold and my wonderful hypnosis files were back! “Four Steps on serving: Learning to be a “Good Boy”” played for hours on repeat, everytime I had the word “good boy” on the tape I would shiver, I had a feeling these files were working, and this was my first exposure. Around 1:00am she unchained me and gave me a break, after which she told me it was time to go back in my box until morning, no restraints or files; just to sleep.  I was begging, pleading, making crazier promises, the thought of all night in there was killing me.

She told me she had to be consistent, and that 15 hours would look easy compared to 24 hours in isolation if I was terribly bad. I truly think I was about to cry, when she told me to lay down and let me sleep on the bed. She had mind-fucked me beyond belief, I must say it worked, and I could feel myself becoming more submissive. Noon came on Saturday and she finally removed my double diaper; which had to weigh ten pounds, not kidding. I still hadn’t produced a bowel movement, I was convinced she had clogged me on accident. She placed my chastity cage back on and let me shower. Saturday night was easy, after putting me into my night time diaper she chained me to the bed again; the files were back. The same dreaded voice of “Good Boy”…”Good Boy”….”Good Boy”…. The voice telling me to idolize my Mistress, when the .wav file finally ended, Mistress removed my headphones…she smiled and cooed “Good Boy”… I was chilled to the bone.

Debbie