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

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

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

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

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?