Jordan’s Diary entry 25


I look back on those first days of cleaning with a gnawing fear in my tummy.

At that time I did not have a clue how to clean a bathroom and I suspect that few of you have any real experience of it either. ‘Being a maid is a profession not a hobby leading to wanking’, at least that is what I was taught a lot later.

Under the sink was a confusing endless supply of packets of wet wipes for all manner of surfaces along with bottles of cleaning fluids for everything under the sun.

Don’t worry I wasn’t going to fall into any traps. I dug out a maid’s apron from my clothing stash and tied it around my waist. I had three aprons from the different maid’s outfits so I chose the smallest, which seemed less humiliating. It was a frilly white square of silk that clung to the front of me and was tied off in a large bow at the rear. A couple of the maid caps were those huge Victorian ones so I selected the smallest one I could find, a sort of frilly silk tiara that I stuck into my hair. Though it looked quite sweet in my wig, my much shorter hair didn’t do it much justice.


I meticulously checked maids caphow I looked in my bedroom mirror as I didn’t want Blair to pick me up for not doing anything correctly.

Oddly the image that stared back was of a submissive looking metrosexual guy, smooth and feminine, whose girlishness was enhanced by the frilly apron and silly little cap.

Then the drudgery began. We have two bathrooms and two ensuites, each seemed to take an age to clean. The variety of wipes tackled them well but still required more elbow grease than I had ever imagined.

The result was that the bathrooms soon sparkled in the daylight sunshine. By simply tidying the various clutter of bottles and jars that litter any bathroom I felt I had achieved a reasonable result.

I had seen Blair add bleach to the toilet bowls so once cleaned I did likewise.

After a much needed coffee and some chocolate I returned up stairs to Chloe’s room. This was the one that, as you well know, troubled me most. If I didn’t clear it up sufficiently for Blair’s liking then I would be in serious woe, however if I disturbed it too much and upset Chloe I would still be in hot water with Blair.

I wondered if my wife knew how much turmoil she was putting me through, and I honestly think at that time she didn’t.

So, Chloe’s room? Weimg-thingll think teenager. Think girl who cannot put anything away. Think of a floor where the carpet is hidden by everything from two week old underwear to magazines.

Aargh. Where to start?

Even the desk and bed were littered with crumpled clothes. When I opened her wardrobes and cupboards I discovered them to be stuffed to the rafters.

I can recall sighing and shaking my head at the apparently impossible task. I needed to ring Blair and explain the issues involved.

It was then that the doorbell chimed and I stupidly humiliated myself totally.

Looking back I think it was me still getting used to wearing a chastity belt for a few days. So being unaccustomed to the permanent state of arousal and submission I simply couldn’t think clearly. That, sad to say, hasn’t improved to this day. In fact it has become worse as I have had to wear the chastity devices for even longer periods.

So I went downstairs and saw the shadow of the postman through the opaque glass of the front door.

Just then my pink mobile rang. I took it out and saw it was Blair. My reasoning decided it would be better to answer the door first and then call Blair back later. I didn’t want to get in to trouble for letting the postman wander off with the bondage items she wanted whilst I was delayed by the phone.
Then I heard Blair’s voice over the speakers in my office, “Jordan! Jordan!”

But outside the door was tonight’s relief. If I missed the handcuffs then I wouldn’t be allowed to cum. There was only once decision to be made. I answered the door and ignored Blair.

Indeed I guess you appreciate that the postman had the key to my sexual release, the end of my desperate frustration. So I guess you can appreciate my bimbo style behaviour.

I opened the door and can picture the postie now.

He was a little younger than me, taller by maybe a foot with a warm ever smiling round face.

I mentioned before my feelings of inadequacy when I faced the delivery guy whilst wearing my chastity belt. There is something mind tinglingly humbling about being near a guy who can use his willy for whatever he wants when yours is locked tightly away without you having access to the key. You feel subservient to them. A feeling I still have whenever a man walks into the room.

So I sort of simpered at him.

Oh, it actually hurts to think of it. I should have realised by the shocked then amused expression on his face that I had committed a wholly foolish act. But I didn’t.

“Mister Connolly?” His glittering eyes gave me the once over as if I were a girl.

“Yes.” I held out my hand for the parcels and letters he was holding. For a brief moment he just sort of stared at me then his grin grew wider showing his teeth. “Can you sign for this please?”

“Sure.” I signed his electronic device, thanked him and took the parcels inside.

When I closed the door I saw myself in the hall mirror.

The tiara maid’s cap was slightly skewwhiff and the maids apron wasn’t as crisp as it was when I tied it on earlier that day.

Oh. My. God.

I literally put my face into my hands. Had I really just shown myself off, dressed like this, to the damned postman? It would be all over the street by lunchtime!

“Jordan!” Blair shouted through the computer speaker. There was a chill threat to the way she said my name.

My mind wouldn’t work. I was terrified of her and the power she had over me.

I timidly slipped into my office, edging round to be in front of the webcam. Of course all I had was the childish screensaver to look at whilst she tumblr_n7f55p8zLS1sel8ayo2_500could see me perfectly on her screen.

“Sorry darling. I couldn’t take your call. The postman was at the door. I needed to get the package,” I explained defensively. “You know the stuff you wanted me to buy? Because if …”

“First stop jabbering like a nervous school girl!”

“Yes dear.”

But I was like a nervous school girl.

“Second, understand this. If I call you then I want to be answered. Got it?”

“Yes of course. Yes darling.”

“I am not second best to anyone!”

Wow, she sounded angry. “No you are not honey, really.”

“Thirdly, I was calling you to warn you how you looked! Idiot!”

I closed my eyes and sighed. Of course. Had I answered her phone call or gone to my office I wouldn’t have made a complete idiot of myself by answering the door with the apron and cap. “Oh. I see. Sorry.”

“You heard me calling you? Over the speakers?”

“Well, yes darling but I thought it best to get the door before the postman …”

“You thought? What have I told you?”

My tummy span over. “Not to think for myself. Sorry.”

“You are always sorry. A little bit of better behaviour and you wouldn’t have to be boring me by saying how sorry you are, would you?”

“No darling. Sorry.”

“I will deal with you later.”

I audibly groaned, closing my eyes as the fears of her ‘dealing with me later’ fogged my mind. A caning would be dreadful but if she didn’t let me cum then I think I would just dissolve into a lump of jelly.

“I have been watching you running around the house with the cloths and wipes. Good boy.”

I swallowed. There was hope. “Thank you darling.”

“Well, remember, I cannot see what incompetent work you have carried out in the bathroom, I will check that later.”

“Yes dear.”

“And you haven’t started Cloe’s room yet have you?”

“Darling. I don’t know where to start. It is full of rubbish, the wardrobes are jam packed. There are books everywhere …”


I held my breath.

“God do you ever pause for breath?”

Sorry darling.”

“Firstly a lot of the clothes will need washing. I sort it out very few weeks. So firstly get her dirty clothes into the washing basket. Then tidy up the cupboards and wardrobes, that will give you a space to put things away. Simply tidy the magazines and other thingees into neat piles.”

“Yes darling.” That all made sense.

“Show me these expensive double locking thingamajigs.”

“Yes dear.”

I put the post down and opened the smaller package to reveal a white box with the words ‘Genuine Double Locking handcuffs’ inscribed on it.

“Wow,” I heard her say. “Well get them out!”leg irons

“Yes honey.” I nervously tore open the box to reveal the twin sets of pink handcuff, one linked with a short chain and the other hinged. I held them up to the webcam.

There was silence for a moment. “Ooooh! They certainly look solid enough.”

She was right on that one. They felt heavier than my toy self-releasing ones in my private box upstairs. These could only be opened by the keys they came with, of which there were a couple for each set of cuffs.

“Show me the other box. The ankle cuffs.”


“Yes dear. I opened the larger package and pulled open a blank white box to reveal the hefty leg irons. They were elegant but felt heavier than even the cuffs. A length of chain of about 10 inches connected them. Again there was twin set of keys.

I heard her giggling and my mind froze. What was so funny?

“Little boy?”

“Yes dear?”

“You don’t want to be punished later for your naughtiness do you?”

“No dear.” I gasped hopefully.

“My little boy wants his little treat doesn’t he?”

“Yes darling. Yes, yes I do.”

“Uh-uh. So let me punish you now. This is going to be soooo entertaining!”

I winced.

“First, take off all your clothes. And I mean strip off everything!”

The words ‘strip off everything’ aroused a spurt form down below. It was so exciting, just like a real dominatrix. I think at that time I thought this dominating me would sort of blow over given enough time.

But let me tell you it doesn’t. Once a girl has dommed you in this way she cannot see you as a dominant male figure ever again. You think of those ‘fetch mees’ Blair and Chloe went on about. Guys they knew were slaves and would fetch them anything. How could they ever see them as real men again?

At that time I still didn’t realise that rather obvious, inevitable change of view point.


I really thought I could get past this period and then move on. Yep, I guess I am as dumb as she says.

So, incredibly aroused I ‘stripped’ off my clothes before the web cam until I was naked bar the chastity cage and of course the maid’s cap I had once again forgotten.

“What’s that over the chastity belt?”

“A condom Miss. Please Miss, I use it to stop me from leaking. I get aroused and as I can’t cum, it sort of dribbles.”

“Stop being vulgar.”

Blair never liked such talk.

“And who told you to call me Miss? What’s this Miss business?”

I was dumbfounded. Where had that come from? “I , er, I , well ..I sort of …”

“Miss,” she repeated to herself. “Hmmm. My friend gets called mummy by her little boy but I am not sure I like that. I would like to have a little boy, but not sure about the mummy bit. Miss?” She mused over the word, repeating it a few times. “Miss. Miss. I don’t know.”

“I didn’t mean to, it sort of just came out.”

“From those seedy little stories you read, little boy.” She giggled before adding emphatically. “Or used to read.”

“Yes darling.”

“Miss. I guess it is short for Mistress? Yes?”

“Eerm yes, I suppose so darling.”

“Uh-huh. Miss. Mistress. Mistress. Miss.” She repeated reflectively. “Well it would be good to be a mistress in a Victorian household wouldn’t it? All those maids to do everything for you.” She laughed. “And those sexy hot guys in the stables and around fixing things. Mistress. Ok. Call me Mistress Form now on.”

“Ok darling, Mistress.”

“Love the way you say ‘ok’ as if you are agreeing to it. Well if it is ok with you,” she giggled, “then it is ok with me. But do not shorten it to Miss. Not sure about that yet.”

“Yes Mistress.”

I spurted into the condom, grateful I put a fresh one on that morning.handcuffs hinged

“Well now put on the apron.”

“Yes Mistress.” Oh heavens, was that arousing. Feeling the cool silk against my bare smooth skin. I think I told you before that I was pretty hairless at the best of times.

I tied it into a bow at the small of my back feeling the ribbons hanging down and tickling my buttocks.

“Good. Now straighten your cap. I don’t like it when it looks messy. That makes it all feel very grubby. I want you to be looking good for me.”

“Yes Mistress.”

With everything in place I just wanted to go to my room and have a play. I reckoned it would take me about 5 seconds to cum.

“Now put the leg irons on.


I hadn’t expected that. I thought we would be playing with them later that night. I heard her sigh.

“Little boy I really don’t want to have to repeat every instruction as if you are so dense you need a spanking every time you get an order.”

Sorry mistress.”

“Do I need to be running behind my little boy constantly spanking his bottom?”

“God no Mistress. No.”

She laughed and relaxed. “Oh your face does look a picture! So let us have those leg irons on now.”

“Yes Mistress.”

I sat on the floor and raised them up. They were like enlarged handcuffs but they were more intimidating than my cuffs upstairs. With those I knew that I could just press the safety release and they would slip off. These required a key.

A slip of paper with instructions fell into my hand. It said about sliding the cuffs past a single point, hearing it click and then twisting the key for the second click, thus double locking them. That would stop the cuffs widening or closing tighter. A safety feature for prisoners. Prevented them from crushing their wrists or ankles.

The steel was freezing against my ankle as I closed it. It ratcheted closed with a click and I already felt trapped. I put the key in and twisted, feelings some resistance before the lock snapped shut.

My breathing became shallow, my head swam away. I had fallen into a foggy dream where my fingers felt like sausages I closed the second one around my other ankle and locked it twice.

“Very good. Wow. And you cannot take those off without the key. Amazing.”

I stood carefully keeping my feet close together.maid4

“Put the keys on your keyboard in front of the web cam, near the keyboard. So I can see them.”

“Yes Mistress.”

I did as ordered laying them in their single key ring on top of the keyboard.

“Now the pink handcuffs. So suitable for a sissy don’t you think?”

I spurted again and groaned a “yes Mistress.”

What a scene this was. And yes, stupidly I saw it as a scene. Some incredibly enhanced wanking session straight from one of my favourite stories. I selected the chained cuffs.

“Not those. Use the hinged ones. They look sexy.”

“Yes Mistress.” I picked up the hinged ones and snapped a bracelet around my right wrist where it clicked through the levers. I put the key in and twisted locking it shut.

I read the few lines of instructions on the box. ‘Simply turn the key in the lock to get the second locking mechanism in place.’

I did so.

“Now the other wrist.” I could tell Blair was getting short of breath herself. I wished she was here so we could satisfy ourselves.

That was when the problem began and again I blame myself for me not thinking this through. Maybe I was too aroused to think anything through.

With chained handcuffs you can use your already locked hand to help put the bracelet around the free wrist. However the hinged mechanism means the hands are secured so close together, and the hinged mechanism so rigid, that you are prevented from doing that.

By placing the wrist with the unlocked bracelet onto my desk and pushing down, and then bending my fingers back from the wrist already cuffed I was able to lock the cuff on.

I guess many of you will have already worked out the problem I was about to face.

I stood up, secured by the cuffs on my ankles and wrists, feeling totally helpless and worse than naked in my apron and cap. As I tottered back I felt the pain of the ankle cuffs and whinned. I would have to learn to take very short steps.

“I tell you something little maid. You look amazing!”

“Thank you Mistress.” She called me little maid and my dick reacted. Pretty soon I would have to change the condom.

“How do you feel?”

“Oh my word. Like I have never felt before. I cannot describe how aroused and helpless I feel.”

“Poor baby and your little dickie all locked away until I get back.”

There she said it. ‘Until I get back’. Relief jarred me, so she was definitely going to free my caged cock. I even smiled.

“So you toddle upstairs like a good boy and sort out Chloe’s room as best you can.”

“Yes dear.”

“And little boy?”

“Yes Mistress?”

“I don’t think you double locked the second cuff.”

“Ah no. No I haven’t. Thank you Mistress.”

And here came the shock of my life.

With my hands held squeezed together I picked up the keys and found the barely flexible structure totally prevented me from moving the key anywhere near the hole.

“I, er I , I can’t reach.”

“Oh.” Blair said as if concerned. “Yes. I see that.”

“I guess we need the chained ones to do that.”

“Erm, little boy?”

“Yes darling?”

“How are you going to unlock them before Chloe gets home if you can’t get the key in?”

My jaw fell open. I slumped into my seat which rolled back slightly with my weight. Whereas before when the seat rolled I could put out my feet to control it, now, with them chained together, I just hurt myself and had to wait until it stopped rolling. Helpless dread swept through me, which wasn’t helped by sitting helplessly locked up on a rolling chair.

As my anxiety intensified I was about to shout out her name but just caught myself as I started screaming, ‘Blair’. “Bl …er, Honey, er, Mistress. You must come home. You must come home right now!”

I rested my cuffs in my lap feeling the chastity cage beneath my apron.

“Little boy I do not ‘have’ to do anything.” She was peeved and I reacted letting my panic get the better of me. I had to learn to be polite at all times. “But it is a bloody nuisance. Why are you so hopeless?”

Me hopeless? I felt like saying I had just obeyed her commands but somehow it did feel like my fault. I should have realised I would not be able to release them once they were locked on. I sat their waiting for her to come to a decision.

“Look, I am seeing this friend of mine for coffee later and I am seeing Morgan, erm Mister Hopkins for lunch. We are going to that new wine brasserie. It is supposed to be a hoot. We always have a few drinks there.”

I felt my eyes sting with fear. “I cannot stay like this all day. Chloe will be back by four.”

“Hush. Let me think. If you believe I am going to give up my social life because you get yourself into a fix then you have another thing coming. Oh I don’t know. You make me so cross!”

“Sorry mistress. Really!”

“I will damn well make sure you are sorry. How could you be so plain dumb! You are going to ruin my day.”

I went to wipe away a tear forming in my eye but was shocked by the pull on my other wrist. I froze. I guess then I didn’t realise how long it takes to get used to being in cuffs. In stories people get cuffed and have a great time. I can tell you that for a while you just feel panicky and helpless, even a little stupid as you are in the hands of others.

“I can take the leg irons off,” I said, hoping that would please her.

It didn’t.

“Have I said you can take the legirons off?”

“No Mistress. I just ….” I was about to use the word thought and it caught in my throat.

“You will take the keys upstairs to your bedroom. You will tidy Chloe’s room as best you can.” She giggled. “Oh I wish I could watch!”

My cheeks burned red.

“Once done, get yourself some lunch and write Chloe a note. Tell her you are feeling tired so having a lie down this afternoon in your bed and she isn’t to disturb you. Then I guess my stupid little maid should stay in her bedroom until I get home to rescue you!”

“Yes Mistress, thank you Mistress.”

“Awww. You do look sweet like that. My friend is right about that.”

My ears pricked up. How much detail had that sadist of a pal gone into? Was Blair sharing our arrangements with her? I felt sick, but knew better than to ask of course.

“See you later little maid.”

For the umpteenth time I sported into the condom.

The speakers fell quiet and I rose from my chair and gingerly made my way to the hall. I can walk quite well with leg irons these days, even with quite high heels, but on that first day I felt like I was about to stumble and fall with every step.

Worse I couldn’t balance properly with my hands held locked before me.

The chain rattled and tinkled across the floor and was a real pain going upstairs. I found it safer to take them one at a time.

As for cleaning up Chloe’s mess, I found I had to concentrate. Every now and then I would forget my wrists were locked together and would reach out for something. Even today when cuffed I do the same but now it is occasional. At that point it was happening all the time.

But oh my word, it was so hot. Every so often I would see myself in one of her mirrors wearing the frilly little cap and the apron with my wrists and legs secured. Why the mind converts a humiliating and scary situation into one of lust is beyond me.

When I was finished I carefully made my way downstairs, made my sandwich and a drink.

That was a long afternoon. I rubbed myself helplessly over my pillows, trying anything to make myself cum. Of course the CB6000 saw to it that nothing like that would happen. I slept for a bit, woken by Chloe tapping on the door.

“You ok dad?”

I clambered under the quilt still not daring to remove the maids cap and called back. “Yes. Just need to sleep for a bit.”

And then began the long wait for Blair to come home and rescue me.

I was no longer sure if she would let me cum as she had been irritated so much by what she saw as my stupidity. I lay there groaning to myself at my plight.

Of course had I known that a line had already been crossed in our relationship I might have moaned even louder. But right then I just felt like everything would sooner or later return to normal.
How wrong I was.

handcuffs chain


4 thoughts on “Jordan’s Diary entry 25

  1. There’s always a learning curve to these things. The good thing is that while a new Mistress learns things, the sissy learns things too. Very symbiotic. We await the next journal entry with baited breath.

  2. I’m now sure Jordan will never escape. He is to be the perfect maid for his wife, his daughter and maybe also his wife’s lover. You can use my mail if you want to know why i say that.

  3. Vania, I am sure you are keeping your fingers crossed that Jordan will pull himself together and become the man of the house again. But i fear you could be right. Deborah Ford

Leave a Reply

Your email address will not be published. Required fields are marked *