Sissy Chastity Literotica

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Sissy Chastity Literotica
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Sissy Alice prepares for her master's return home.
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Transgender & Crossdressers Sissy Life: 50 Days in Chastity
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Favorited by con6ta , raf013 , FASfan and 10 others
50 Days in Chastity - needs FIFTY PAGES !!! :)
Sissy Life A pathetic sissy blows the chance to impress his wife.
Sissy Life: Valentine's Day Wife's lover takes 'ownership' of Sissy.
The Man That Owns Me Ch. 01 A sissy slut meets the man she will serve and obey.
From Husband to Man's Sissy Wife As my big titted wife takes a lover, I meet a man...
Sissy Meets Daddy A sissy loses her virginity.
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This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'.
'Congratulations! You've managed 50 whole days of proper service. I'm very proud of you. I knew re-focussing you by putting you in that device would pay dividends. And I knew when you failed me so spectacularly as a man in Rob's absence, that a good long stint without release would be the making of you.' By 50 days of 'proper' service my Mistress meant I had been locked in my chastity device without release for that period. Given that she held the key, I'm not sure it was much of an achievement on my part. I mean, I would have got out if I could have! I knew better than to say that though. I curtseyed and thanked her for the feedback. Plus, I had worked hard. Especially after the whipping from Rob.
'Let's have a look at your reward chart shall we? See just how well you've done!' My reward chart is up on the kitchen wall where we were stood. It's like a reward chart you would have for a child, except it's massive ('so people passing by the window can catch a glimpse of how you're doing') and instead of getting stickers to put on it...I have to cut out pictures of men I 'fancy' when I've done well. Under each picture is a brief rationale as to why I chose that man. All the pictures come from the gay porn magazines I'm subscribed to. It's humiliating beyond belief!
'Look at that. 50 hot guys looking back me; not one poor day of service! 'I chose Anton because of his strong shoulders', she read a line from one of my rationales and smiled. 'See, you can't say that little device isn't worth its weight in gold.' I curtseyed again. 'I can't wait until I have 300 hots guys staring back at me, that will be some achievement! That will be a day to be marked. Now, 50 days deserves a reward, don't you think?'
'Oh yes Mistress! Yes please. I have tried very, very hard.' I silently prayed that she'd let me out.
'You have indeed. And without getting hard at that!' and she laughed. 'Meet me in my study at 8pm sharp. Give your uniform a quick once over with the iron beforehand. And you can take your heels off!' With that she unlocked my uniform and left the room. I checked the 'extra' chore list next to my chart; I'd done everything I needed to do on my daily list, I wondered if there was a quick win I could do to secure my place in the good books. I didn't have time to buff the floor, but I could get a head start on tomorrow's ironing. I settled on that, especially as my uniform now needed the once over too.
I tackled some of my Mistress' ironing before I did my uniform. I have learnt that wearing my uniform for even short periods gets the lace pretty creased, so the trick is to iron it as near to inspection time as possible. Giving it a 'quick once over' was near-on impossible mind as all the lace & frills means it takes time to iron sufficiently. Once I was happy that it was up to standard - I figured now was not the time to fail inspection! - I slipped it back on, took off my shoes (what's that about?) and went to the study.
Sarah wasn't there. I knew I where I needed to be - on my sissy spot. I wondered, given what I hoped would be my impending release, whether to kneel instead of standing.
I heard Sarah come in. 'Hello dear. Kneeling like a good boy! I do like it when you kneel. It's the one thing you do that gets me wet these days. Not always practical - kneeling - in your tight maid uniform I know. We had to spend some time perfecting your kneel as I recall.' We spent a whole weekend on it! 'And we did have that snagged stockings incident that time didn't we? You know now of course how important it is to be up to standard uniform-wise. But I do like to see you kneeling! Shows your understanding of your subservience perfectly. Although, it does mean you can't curtsey! And I like seeing you curtsey too! Ha!' I went to get up to curtsey. 'Stay on your knees sweetie.'
She sat down in the leather chair. There were 4 packages on the desk. 'So...' she started, 'I think it's time for your reward. Rewards plural actually.' Hhmm. Didn't look like release was on the cards... 'These packages are numbered 1 to 4, that's the order you should open them in. Come on, don't be shy.'
I reached up and picked a package. It was pretty heavy. It also had a '3' on it so it wasn't the right one to open. The second one had a '1' on it. It said, 'Silence is golden sweetie' on the label. I carefully unwrapped it. It was...a ball gag.
'It's a ball gag honey!' My Mistress clapped her hands with glee and got up. 'Like the one you wore when you served Tony & I that night. There are just a few differences. One, it's black. That's important because this is now part of your standard uniform. Whenever you have your uniform on, you have this on too.' I groaned inwardly. It was so uncomfortable to wear. 'Two, the ball can be swapped out for something different. For example, it can have a penis gag instead, and' she was stood behind me now, 'open up, three, it locks!' I heard a click and the gag was secure. My jaw started to ache almost immediately. I couldn't imagine wearing this all the time. It's funny, I found the gag more humiliating than the rest of the whole uniform.
'Stand up for me.' I stood. 'Now curtsey'. I curtseyed. 'That looks great. I am going to love having you wear that. There's no need for any chatter from you, so it makes sense. Whilst wearing it, it's one curtsey for 'yes' and two for 'no' remember. Open present number 2!'
I picked up the package with the number 2. I suspected I knew what this was (it had 'Tinkle, tinkle here I come!' written on it), but I was only half right. It was, as expected, a collar with a bell on, but unlike the one I'd worn when I served my Mistress and Tony, this one was black, was much larger and was shaped differently.
'This is a posture collar. You'll see it has a bell on, because you can recall how much I enjoy being able to hear you tinkle as you go about your duties, but the key aspect to this is it assures the right posture in the wearer. It alleviates slouching, keeps your chin up, your neck extended and stops you hanging your head or looking down. You will now always be standing to attention as a maid should be. As such', I heard it lock in place, 'it is also a standard item to be worn at all times from now. Unlike your gag, I expect you to wear it all the time, irrespective of whether you have your uniform on. If you have your guest uniform on you can wear the smaller pink one, otherwise it's this one. That includes when you dress all frilly for me when I fuck you. Understood?' I couldn't answer with the gag in so I curtseyed once for 'yes'. The gag and the collar were really uncomfortable! If I thought serving in heels was tricky, my uniform had just got a whole lot worse!
'Now you can open number 3. This is fun isn't it? You must be so pleased at being rewarded!' I curtseyed again. The third package contained heels. They looked like they had 4 inch heels, so no different to what I usually wore. I was pretty relieved!
'Put them on, put them on.' I did as I was told, but couldn't figure how to fasten them...there were two holes, but nothing to put in the holes. 'Ta-da!' My Mistress was stood over me holding two locks. 'Allow me' and she bent down, threaded the locks through the holes and closed them. 'Perfect! Lockable shoes dear. Just another improvement to your uniform. And another good reason to ensure we end the day on good terms - or it won't just be your uniform you're left locked in. And I know how uncomfortable being in heels all day can be. It's important to look the part though! Now, let's have a good old look at you. Walk to the end of the room and back. When you get back here, curtsey for me'.
I did as instructed. The shoes felt fine, but the gag was making me drool and the collar was giving me back ache - and making walking in my heels harder as I couldn't look down at them. I got back to my sissy spot and curtseyed - and nearly fell over! The collar was knocking my balance right off. 'This is fab! These changes are perfect. Just what I was hoping for. Let's open that last package. It's from Rob.'
The last package was massive and when it was unwrapped I still couldn't tell what it was. It looked like a big box or a tray. It was rectangular, made of wood and had 'Maid to Serve' etched into one side. God knows what it was for!
'Wow, that is perfect. It's a usherette tray! You know, like ushers had at the cinema or the theatre in the 50s. Like I said, this was Rob's idea. You're always carrying things he said - and he's right - so why not give you something to help.' The tray had a strap that went over my head and a buckled belt that went round my waist. With this on I definitely couldn't see my heels and with the collar on, I couldn't really even look down at the tray. It wasn't too heavy, but it clearly wasn't going to make doing my chores any easier.
'Ok!' she said with a big grin. 'Walk across the room and back with your tray on. Let's have full effect.' I did as I was told. I figured I was still expected to curtsey, so I did but it wasn't easy as the tray interfered with the skirt part of my uniform. 'That's just fabulous honey. You really look the part now. 'This', she ran her finger along the tray, 'like your collar, is to be used at all times, even when you're not in uniform ok? It doesn't lock, so I'm trusting you to use it appropriately. You can take it off when you have to - like when you need to be on your knees scrubbing the floor or when you're cooking - but it goes back on immediately. Or I will find a way to lock you in it. I am trusting you to understand the importance of these uniform amendments. This is your role in our relationship now. Got it?' I curtseyed once for yes. She checked the time. 'It's a little late, but I want to see these things in proper action before we bed . Tell me, have you changed my sheets today?' Two more (awkward) curtseys for no. 'Ok, let's see you do that in your new improved uniform.'
We headed to my Mistress' room where she plonked down in an armchair and I got to work. Stripping the bed wasn't too tricky, but as I went to put the sheets in the washing basket my Mistress stopped me. 'What are you doing sweetie?' I couldn't talk so I just curtseyed. She sighed and walked towards me. 'This', she tapped the tray, 'needs to be used. There is no point having it if it isn't going to be used. You should have folded the stripped sheets, popped them in your tray and walked over to the basket. I know that's not as quick as just dumping them in there, but being a sissy husband is about doing things right, not quick isn't it?' A curtsey from me. 'Carry on.'
I went to the cupboard to get the fresh sheets. I popped them in my tray and walked back to the bed. The weight of the sheets in the tray made walking toe to heel ('the way a sissy should') quite tricky, but I managed. I got to the bed, carefully took the fresh sheets out of my tray and started putting the bottom sheet on. 'Stop! Stop right there.' My Mistress marched over. 'You're about to sort the bottom sheet on right?' A curtsey 'yes' from me. 'So you're not about to use the rest of these sheets right now?' Two curtseys for no. 'Right, well they stay in your tray until you need them. I can't stress the importance of using your tray honey. Rob really likes the idea so you need to get onboard. You need to please him as much as me. I can get the paddle if I need to be reinforcing some of this.' Two curtseys from me. 'Carry on then.'
The rest of the task went without incident, but I did notice that it took me more than half an hour to do; it normally took less than ten minutes. The tray was really slowing me down! Having inspected my work, my Mistress decided it was acceptable and sent me to get her a drink of water whilst she got ready for bed.
Making sure I used my tray to carry the water, I knocked on my Mistress' bedroom door. It seemed a long time since this was a room I shared. 'Come in.' I went in put her water on the dresser. 'Pop my clothes in the basket sweetie.' This wasn't an unusual request. It had been a bugbear of my wife's when I used to leave dirty clothes on the floor so I figured this was her payback. I bent down and popped her dirty clothes in my tray and then put them in the basket. She seemed pleased with this and, seemingly satisfied with the alterations to my uniform she indicated for me to kneel so she could undo things. It was huge relief to have the gag out of my mouth and although the collar stayed on after being unlocked, unlocking it did make it less restrictive. 'You'll have to pop your tray off to take your uniform off' she said after unlocking my uniform, 'but then it goes straight back on. You can take it off for bed obviously. And your collar.' I started back to my room before I realised my heels were locked on! I turned and went back. I knocked on the door again and was relieved when my wife obliged in unlocking them. Back in my room I stripped for bed. What a day!
Well done and extremely creative. Please continue this one. Love the tray and the obligated continuous wearing of the tray. Owner sits in an armchair and the sissy gets to work on the bed...with the insipid tray - HOTTTT!!!
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