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.

Welcome home sex, and Mistress's large strap on.

Mistress and her large strap on

I want to be this smooth

It becomes evident your life is slowly changing when you notice certain changes in how you begin to think, what you find attractive, what you look forward to, and what you plan on purchasing to make the person you serve happy. Over the past few days I have been gone, and while I was getting ready for bed in my hotel I pulled out the diapers from my bag and with a disgruntled action tapped them over my chastity device. The thought raced through my mind; here you are alone and your putting yourself in a diaper...not because it's what your mistress wants you to do, but because you need it. Thats a disheartening thought, yet it also made me think of Mistress, I hated to be away. I was so happy that I was able to return home today, despite the fact I was exhausted due to lack of sleep. My chastity device was digging into me all night long. I normally do not stay hard all night, but my balls are very full and aching...Im horny as hell. Speaking of being horny, Mistress is watching a video of a very attractive blonde Mistress milking her sub via a milking machine. The slave has a funnel gag and she pours his semen into it, I'm shocked at how much is coming out as he's wailing in pain. "Research how she made that device, I want one, its awesome...you'd never have an orgasm again" Mistress said. Of course, why wouldn't she! "Your being totally serious aren't you" I replied, "Yes, stop questioning me." Whoa is me, this wasn't the only new "item" Mistress informed me I was to research and buy within the next few weeks. "I have an assignment for you, I need you to buy a crib within the week, solid wood. Your going to build a top for it so I can lock you in it. Yes a small crib, but it's much bigger than a dog kennel isn't it? You'll actually be able to sleep in it at night, every night....I'm so nice to you" she said with a serious face. This is not something I'm looking forward to, I don't want to sleep in a crib! I work hard, I deserve my bed!
When I arrived home today Mistress was happy to see me, I was still on a business call and was for around an hour after she got home. We had a family dinner to attend which was lovely, we stayed much later than expected though and my lack of sleep was catching up with me. Returning home I simply wanted to close my eyes, have my chastity removed, put my diaper on and cuddle up to Mistress and sleep. She told me to lay on the bed to be diapered, thank you lord! I was going to get rest! As she approached me to unlock she stopped, smiled and pointed to the bathroom "Go put your butt plug in, the large one". I did as I was told, adding a black thong to my ensemble to help hold it in as I waddled about the house. She was sewing in the living room finishing her new, improved, larger, fluffier, more embarrassing... petticoat. About thirty minutes later she returned for me to try it on along with my maids skirt. Once she decided she needed to make me a new skirt to accommodate my new petticoat she stated "Your going to have multiple maids outfits! You can use this skirt and the normal petticoat and I'll make a new skirt for this big one! It shows your ass! So cute!". After I folded my uniform and put it away she told me to lay down on the bed, unlocking my chastity device and removing my panties (which I looked great in if I do say so my self, wait...what did I just say?) she stated "Face down, ass up, lets go". Removing the plug she approached me from behind and rode me for about ten minutes with the smaller normal sized strap on. Suddenly she tells me to stay there as she vanished into the bathroom, only to return with her largest strap on, the one I've never been able to take. "Sshhhh don't talk or I'm gagging you, you can take this, be a good girl and don't fight it, just open up for me." When she entered I wanted to cry, I cleared my mind and just took it. It kind of felt good after a few minutes and I couldn't believe what was inside me. When she was done I laid there taking it in before she returned to diaper me for the night.  I wonder what tomorrow will bring, on a side note I am surprising Mistress and purchasing a true steel bone corset for her to add to my maid attire (she's mentioned them in the past). I found a site doing buy 1 get 1, with great reviews so I plan on purchasing a hot pink one and a black and white one. To reinstate what I said in the beginning, its scary that I find myself wanting to look pretty, for my uniforms to look good, and my panties be sexy, I feel her plan is working.

They say nothing beats welcome home sex,

Sissy

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.

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