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.

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

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.

I kind of had sex! And a photo of Mistress...

Apologies for the short post yesterday, but I was frustrated, and suppose in someways I will be until things fall into place for good I suppose. Work today was long again, we're wrapping up alot of projects which means a very stressful intense eight hours...and there's no kink to it! I got home today and tried to enjoy myself since today was one of the days where I got home three hours before she did. I didn't take a nap, and the house was in pretty good order so I put a few things away and got it looking good. Mistress had text me earlier in the day telling me to be in my heels and uniform when she got home, and to properly greet her. She called around eight and I was sitting at my desk working on one of my hobbies; which it seems I never get time to do. She asked if I was in my uniform and I told her no, which led to a five minute chew out from her and how to not even cook dinner since I wouldn't be eating and would be punished for the remainder of the night. I told her to calm down, and that I was simply giving her a hard time and I was in fact in my uniform. She calmed down and got off the phone, and I rushed to put my uniform on. When she finally arrived I greeted her at the door...knelt...kissed her hand (I thought it was her ass, or maybe her foot? Im not sure she only went over it once and that was weeks ago, its no wonder Mobico was so good at his commands...he got practice!) After she got home she came into my office and we had an odd discussion on something which was bugging her; how I always make excuses. In my mind do my excuses matter? Why does she take them into consideration if shes the one in control? I suppose that is why I don't understand why she gets so upset. She actually ended up cooking dinner, she wanted me to finish what I was working on. When dinner was done I went ahead and sat on the floor next to the couch, I suppose she was happy she didn't have to ask. When the Kitchen was clean I went into the bedroom and laid down as instructed.

A picture of Mistress's ass I took last night before bed.

You know the drill; Posture collar and gag locked on, hands chained to the bed spread wide and my hypnosis files began to play. The first file was one which aimed at the listener obsessing and longing to worship the female ass, longing to get off at the thought of serving them, but never able to. I like this file, it really turns me on; while it was playing she blindfolded me and wrapped a scarf around my eyes so I could not see. Removing my chastity device she began playing with me, edging me while she inserted a good size butt plug into me (I was shocked at the size after, I thought it was the smallest plug we had... it wasn't! Guess I'm getting used to being filled). She teased me for thirty minutes as the hypnosis files played on, before she got out her vibrator and filled me with it, her teasing became more intense. I thought she might get the strap on out, and was hoping she would since it's collecting dust. Any way it did not come, and the teasing continued. After an hour of teasing and me squirming against the vibrator, wanting it to go deeper, yet it seemed she didn't get the picture, she decided to change things up.
One thing I will say about Mistress is she likes to learn things the hard way. She knows other dominants put there subs in two condoms and apply numbing cream if they feel in the mood for sex and want to use their slave to obtain it. In her mind two condoms would be enough where I couldn't feel anything...she was wrong, and I was happy. She slid the condoms on me, and I thought she was simply using them to collect my cum since shes begun saving it. Then, heavens gates opened when she slid onto me, my dick was jumping with joy and my body with pleasure "You've missed that so much, its finally happening". "You said we weren't having sex again" I muffled through the large ball gag.... "You have two condoms on and a big cock is vibrating in your ass....this isn't sex" she replied. She rode me slowly for about five minutes, once she got off several times she crawled off and finished me off by hand. All the while the vibrator still buzzing away inside me, she was attempting...ATTEMPTING to give me a ruined orgasm, my guess is due to she has not learned how to milk me with a strap-on, it takes practice...shes not patient. When I got off I finally felt amazing, happy, relieved, and completely out of subspace. She undid my restraints and diapered me promptly, telling me to make her tea for bed. I thanked her for what she did;  "Wait, that felt good? How'd you feel that?" she said. I told her she paid the cost for not using numbing cream, and she should learn what milking is, and how to do it.  Frustrated she got ready for bed, and I laid down for the night. Today was better than yesterday, but I wonder if it's simply because she knew I was frustrated? I know this process takes time, and I'm willing to be patient...but when your making your submissive listen to hypnosis files about worshiping asses, strap-ons, and obeying your every command...exercise the commands of the hypnosis before they loos their mind!  My wetting is increasing significantly, and I'm starting to walk in heels well, sometimes I forget I'm in them. I have this strange want for my uniform to be complete so it doesn't look so ridiculous; like hair, smooth skin, etc... hopefully in time she will complete it, and me. Im ready for more changes, I just want them to come. I know life is going to change drastically, I just wish it would get here.

Debbie.

Sex in my new role, and I enjoyed it?

Well, tonight was interesting... but...my balls are no longer aching! I had to attend a funeral this evening, Mistress was forced to stay late at work, which is why she did not go with me. I got home around 8:00pm and we sat down and ate dinner she had prepared. I wouldn't say she' the best cook, but on certain things; she will blow me out of the water. I do most of the cooking now, which is ok seeing as I truly do enjoy it. She's still working on building her memory, this became evident since she didn't say anElena's Hypnosis files, Mistress is a big fan. You get in a trance after Elena takes you under, and her words are the only thing you focus on, it's creepy). The files began to play, it was one I have not heard before which consisted of feminization, humiliation, worshipping strap on's and sucking cocks, and being a good girl for your Mistress. About thirty minutes in I feel the bed move as she climbed on, then my mind was literally fucked. Mistress began inserting the dildo from her strap on into my rear, in and out...in and out...then she attached a vibrator to the end, my body began shaking with the shoots of pleasure coming from an unlikely source. This culminated with the hypnosis file telling me how I need to only use my holes for pleasure, how I need to worship other strap on's or cocks, and embrace the fact I'm now a sissy sent my mind on a whirl wind of emotions. Then she began stroking me; all the while pushing the dildo deeper and turning the vibrator up; this sent me over the edge.
ything when I sat on the couch to eat (she normally makes me sit on the floor and eat). I assumed she simply wasn't in the mood to indulge in activities tonight. After about an hour she told me to strip and be ready for her in the bedroom. "Are you ready for more of your files sissy?!" she asked mockingly, she knows I can't stand them, but more worrisome is the fact that she knows there working. And tonight they would take me on one crazy ride. She left my chastity device on, and began chaining me tight to the bed limbs spread to each corner. "Don't you dare mess yourself since your diapers off" she stated as she began to pull my limbs tighter securing them with the click of a padlock around the leather cuffs. "It would be in your best interest not to talk, one word and the gag goes on for the night, this isn't a game." I decided after the events of last night I should take her seriously. The headphones went on as well as the blind fold, followed by more fabric wrapped around my eyes to ensure no light entered (I suppose she will need a hood soon). The files came on and I began to fall into the depths of my mind (If you've never listened to hypnosis files go check out
My mind kept flashing images of me; dressed as a slut with my Mistress over me taking me with her strap on, images of me with fake breast, make up, a wig dressed to a tea on display in bondage, images of me being put to bed in a cage in the corner of the room, then the realization that I was enjoying the dildo in my rear alot more than I expected, I also realized I had been pushing down so it would go further. These thoughts are shocking kind of, and I don't know what to make of them right now. All I know is in the moment, I wanted more and I thought to myself if this is sex now...your going to enjoy it. She continued to stroke me more and more, after words she told me she was telling me to "let her know when I was about to cum" but she didn't think about the fact I could not hear and could not see what she was saying. I was so lost in the moment, focused on each wave of pleasure coming from multiple places. She kept stroking faster and faster and I kept pushing the dildo mumbling deeper, she pulled out the dildo and inserted her larger vibrator quickly into my hole...after a few deep thrust I couldn't contain myself... the pleasure was simply to great and I cam into the towel in her hand. She left me there, with the vibrator still deep in me for twenty minutes. I was high from the pleasure, I wanted more. The files ended and she removed my battery powered new friend and diapered me very tight. After unchaining me she told I was going to fuck her, I was very confused. Then she strapped the strap on over my diaper and told me to get to it. "You finally get to fuck me with a real dick, are you excited? Your in a diaper, and you've already wet it... how pathetic you are." I climbed on top of her and began to do what she ask, she came very fast. "Get used to this, its the only way your going to fuck me." she said closing in content.  Now I'm sitting here in a very wet diaper which is very comfortable, feeling very relieved that I got off, even if it was by accident. I haven't experienced that much pleasure in along time. The emotions I felt and the pleasure from my ass are still confusing. But I'm not scared to move forward, I trust her, I love her. If I have to be a slave, I'd only want her to own me. She told me that soon my chastity device won't be coming off anymore, that I'd have to get used to sleeping with it on under my diaper. I'm nervous about this, but I understand that it's what must happen. Thanks for reading, and sharing my journey. Changes are happening, who know's where I'll be in a few months.

Debbie

I should have put on my uniform...

I apologize but this will be a short post, I'm exhausted from this evenings activities. Mistress got home around 8:30 and was not in a good mood since I wasn't in my maids uniform as she requested...I'm really wishing I would have put it on. To say she was mad is an understatement, she drug me to the bathroom inserted a suppository, quickly diapered me along with my pink plastic panties. The chained me spread eagle to the bed where I couldn't move. Then came the large gag, ear phones, sound proof head phones next, blind fold and panties on my head. Two hours of isolation hypnosis files followed. My balls are aching, My diaper is beyond full and I don't get changed until morning now. My limbs are sore and ass red.... Lesson learned.

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

The first waves of Feminization, the making of a sissy.

Sunday was an unusual day to say the least for me, though I fear days like it may become the new normal. The first half of the day was no different than normal; I went out and worked at some of our property. When I arrived home she told me it was time for me to do my chores. Which was fine at first thought, I truly don’t mind helping out around the house, because it makes her happy. I think that’s why I even agreed to live this lifestyle in the first place; she truly has taken it to heart, and I honestly don’t think I’ve ever seen her this happy, confident, and content in our four years together. I Love her more than words can describe, so if me making these sacrifices make her the happiest girlfriend…or Mistress in the world; I’m happy to play along…though I don’t think it’s a game anymore.

Apologies for the diversion; she told she needed to get me ready for my chores:

1.) Organize and detail the Laundry Room

2.) Clean the Kitchen and do all the dishes

3.) Sweep all of the floors and vacuum the rugs

4.) Clean her Master bedroom

5.) Iron 15 pairs of pants (I.Hate.Ironing)

Upon entering the bedroom she told me to strip, and reminded me I was not to wear clothes in the house unless she had picked out the outfit or it was my normal attire of wearing only my diaper. She told me to bend over and grab my ankles, proceeding to insert a small plug into my “sissy hole” as she now calls it, followed by a black thong which she pulled over my hips to help keep

it in place, followed by a pair of red lacy Rhumba panties. Then came a black garter belt, followed by black nylons, white petti-coat, small black maids apron, thick elastic black waist belt (to get me used to corsets she stated), a black lace bra and white elbow gloves completed my attire. Humiliating is an understatement, I hate the idea of being “feminized” yet I know it’s going to be a major part of my transformation into her “Sissy Slave”.  Before sending me off she attached the leather ankle cuffs linking them with a 14 inch long chain, locked of course. Then came her new Posture collar and large ball gag. “Off you go, I’ll check on you in a few hours…I’ll be in my office”. The posture collar hurt like hell, the gag was causing me to drool and the thin plug was moving in and out with each hobbled step. This was not fun.

Upon completion of the chores and my near pain break down of the posture collar she told me it was time for more files, wonderful.  Except this time she chained me to the bed with more attentiveness to what she was doing, stretching my limbs so I was spread eagle and not able to move, attaching a 4 foot spreader bar to my ankles before pulling my legs as tight as she could and locking each to the frame of the bed. Blind fold, gag still in, headphones on and lights out.  The dreaded voice came back through the file except this time it had a new message “Obey Women” for over an hour, then the file went to the next track which was an hour of attempts to make me obsessive of wearing lingerie, and worshiping Mistress’s strap on. I just wanted it to end. But it didn’t, it kept playing and found myself lost in time once again with my subconscious leaving me questioning who I was becoming, it’s clear I was no longer the man of the house. The light peeked through my blind fold when she came in the room, sitting next to me simply smiling and petting me. “Good Boy” she repeated.

“Did you enjoy the files sissy?”

“Not hardly” I replied.

“You will.” Grabbing my caged cock and shaking it in her hand “You know this wont be inside me for along time, maybe ever. Vanilla sex as you knew it is a thing of the past. But don’t worry, you’ll still get to enter me, I just need to go buy some numbing cream first”.   I gulped at the thought of this, was it really happening, so fast? But she promised me in the beginning I would still get sex! In my mind I was protesting, dare not out loud.

“Don’t worry I’ll start fucking you soon, your going to grow to love my cock.” Smiling, she said no more. She diapered me and I was off to bed with some hope of a reward. Before passing out I heard “Make a mess in your diaper for me by morning, and you’ll be rewarded”.  I knew one way or another, I had to make a mess.  “Are you really telling yourself to mess your diaper, looks like her brain washing is working” I thought silently to myself.

“Good night sissy, get ready for tomorrow” was the last peep I heard out of her while I fell asleep with my face in her ass, as she’s now instructed me to do every night. I noticed the hug of the diaper, and began to think about how comfortable it was...maybe become dependent on them won't be so bad?

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