SISSY FIFI'S DIARY - JULY 2021


(Editor's note: This is adult content and real)

Mistress Emma has told me to keep a daily diary and at the end of each month, produce a summary. This is my third one...

This month Mistress Emma has been teaching me dressmaking skills. My own efforts so far are not very good but I am getting better with the sewing machine as time goes on. Mistress says I have potential, and I love it when we sit side by side working on something new, or when she gets me to stand on a little stool like a manikin while she fits a new garment to my body.

Mistress is really talented and creative, most of my sissy outfits are her creations - not made from scratch, but adaptations of things she's bought from charity shops or the internet. Some of them begin as children's clothing or fancy dress costumes and are then made to fit by the addition of darts, pleats, frills and ribbons. Fortunately I am slim and not too tall so making things fit is relatively straightforward - especially since Mistress likes my outfits to be tight, constricting and skimpy: what she calls the "baby slut" look. I am sure that if she wanted to, Mistress could earn a living through dressmaking but she prefers to keep it as a hobby, and in any case she's very committed to her career in nursing. This month she made me a "Little Red Riding Hood" outfit which I'll have more to say about later...

My own skills are more in the area of DIY. I'm not a proper carpenter by any means but can make and repair household items, as well as making things specific to our female led lifestyle. For example I made the cot I sleep in, and have adapted a chair and a table for bondage purposes. My current project (the most ambitious to date) is something called a Spanish Donkey, which Mistress tells me was originally a mediaeval torture device - basically it's a sort of wooden wedge, which the victim sits astride with ankles secured either side so the hard, upward-pointing V presses into the groin. The version I'm making will be painted pastel pink and have a unicorn head at one end to make it resemble a piece of nursery furniture. It will also have casters underneath so it can be moved around. I'm enjoying making it even though I'm fully aware that it's something I will dread having to "ride" once it's finished; but after all the main point is to please Mistress, not myself.

My penis has been very sore this month, because it's been getting regular thrashings from Mummy each week when I go to clean for her. It's an overdue punishment for something naughty I did as a child that I only recently admitted, so she added "compound interest" for all the years in between and the total was 139 lashes! Well I couldn't have that all at once so she's done it in installments, but that means I don't get to heal completely in between whippings. My boy bits are too raw for me to wear panties or my chastity cage, but Mistress says that's ok because there's no way I could masturbate in this state anyway. She finds it very funny to see me so uncomfortable and is constantly squeezing or flicking my penis to make me wince.

One major event this month was going to Mummy's house and having her parade me in front of her neighbours in full sissy bondage. It was the same mother and daughter who called round a few weeks previously, when Mummy hid me in an ottoman. For their latest visit I was dressed in my bunny rabbit head-dress, a really short frock, hold up stockings and my ballet boots. Mummy strapped my arms out at my sides using a spreader bar fixed to my belt and pulled my panties down round my thighs. I must have looked ridiculous serving them coffee like that, and sounded ridiculous too because under my skirt I had a plug with bells hanging from it that tinkled as I moved. The guests laughed a lot to see me that way. Mummy let them see the tattoo on my penis and invited them to put crocodile clips on it. They laughed even more when I had to say "thank you" to them for doing it (through a dummy gag).

The daughter, whose name is Sophie, looked at me with utter contempt when handling and hurting my penis. I think what made it even worse was her being so pretty and so much younger than me. She asked Mummy questions about my chastity regime and wrinkled her nose in disgust on being told about my previous masturbatory habits. I know from things they talked about on their last visit that she has a younger brother and I wonder if he might end up suffering a similar fate to me, given how much his mother and sister seem to approve of my treatment.

I have managed to get through a whole month without being put "in disgrace" by Mistress Emma, I think she has been extra kind to me in light of how severely I've been treated by Mummy. She hasn't catheterised me at all, and I've been allowed to sleep in her bed three or four times a week.

One evening recently Mummy came over to our house for an evening of playing board games. We do this quite often and sometimes it's scary for me because they impose penalties on me when I lose points. This time was ok though, that didn't happen. We just had fun together as a family, the only difference being that Mistress took my turns for me due to me being in bondage. Actually I was in my new Red Riding Hood outfit: a hood and cape, red opaque hold ups and ankle boots. The bondage part of the costume is a red latex sleeve that my arms go in behind my back and are then tightly pulled together with a drawstring. Mistress Emma and Mummy were in bodysuits as usual, looking very sexy like always, and my penis was trussed up, pulled back tightly between my legs and fastened behind to the end of the arm binder. Sitting like that in my usual state of frustrated arousal made it very hard to focus on the games we played.

After a long game of Trivial Pursuits Mistress suddenly announced that we were going on an adventure. She put a blindfold over my eyes and a collar round my neck with a leash on it. I stood waiting for a while and could hear their voices but not what they were saying, so I think they must have gone into the next room.

When they returned I think it was Mummy who took the leash but I'm not sure. Anyway we went out of the house by the back door, into the garage and got in the car - Mistress and Mummy in front, me in the back.

We drove for a long time, then stopped. I heard them get out and Mummy told me to get out too. In my blindfold I had no idea where we were apart from that there was the sound of traffic in the background so I knew we weren't far from a busy road.

After walking for a few minutes in silence we stopped. Mistress said "how about here?"

Mummy replied "ok", then a moment later I felt Mistress' face close to my ear as she whispered "we'll see you later, little one. Don't move!"

The last I heard of their voices then was Mummy further away calling "Bye bye sweetie!" and Mistress laughing.

Wherever I was, I'd been left there alone. My guess is that I'd been tethered to something by the leash but I'm really not sure, because I stood as still and silent as possible - not just because I'd been told to, but also out of fear. The chances are I was well hidden, but there was no way of knowing that for sure. With my arms laced tightly together in the sleeve behind my back, and completely naked between my little cape and stocking-tops, anyone who saw me would know I was utterly vulnerable. They could do whatever they wished to me, and get away with it since I was blindfolded. In any case I could hardly call for help dressed as I was - I'd be arrested as a pervert.

It was a very warm night but a breeze was blowing and I heard leaves rustling which told me I was probably in a wooded area, like Red Riding Hood in the children's tale. I was very scared, but my penis was stiff between my legs and I comforted myself by squeezing my thighs together until I almost squirted.

At certain point, Mistress and Mummy came back for me, we returned to the car and drove back. The time in between seemed very long to me but they said it was less than an hour, and all they'd done was drive to a service station for coffee. As a reward for not ejaculating during my ordeal I was allowed to give both of them tongue service once we were home. This is the first time I have been taken out in sissy bondage but I think it won't be the last because Mummy and Mistress Emma said the riskiness of doing it was very exciting for them. They have often talked in the past about taking me out in sissy bondage but this was the first time it's really happened. It makes me think it won't be long til they enact their favourite fantasy of taking me on some sort of holiday where I can be kept in bondage 24/7.

Towards the end of this month Mistress acquired an exercise bike that one of her work colleagues was getting rid of. When she showed it to me I remarked that it doesn't have handlebars or a saddle but she said that's ok, you won't need them. Instead of a saddle I have to wear a plug, and when I mount the bike the end of the plug fits in where the saddle used to go. There's a sort of metal plate, but it's very uncomfortable to put my weight on. The reason I don't need the handlebars is that Mistress ties my thumbs to nipple clips. She also puts clips on my boy bits with ribbons going to my knees. The effect is that when I peddle, the movement of my body makes all the clips move.

Mistress made me use the bike for a whole hour, I couldn't slow down or stop for very long during that time because there's a sensor to record rate and distance and she set a target I had to reach. In any case staying still is almost as bad as peddling, due to the pressure of my bottom against the metal plate.

She also made me repeat a sentence over and over while doing it - it's so humiliating I can't bear to repeat it here and Mistress says I don't have to. She's going to make me use the bike on a weekly basis from now on.

Mistress had a couple of friends over recently, for the first time since covid started. It's nice for me when people visit because I get to be treated like a regular person for a while. Of course I still have to watch my behaviour, because if I do or say anything presumptuous I can be punished after the guests leave - so I am still under Mistress Emma's control; and to be honest it was a relief when we were alone again so I could change back into my maid's uniform and suck my dummy.

I'm hoping that now things are getting back to normal after the covid restrictions we will have more social contact at home and elsewhere. But no matter how things change, one thing will stay the same: I belong 100% to Mistress Emma and Mummy.

Mistress Emma writes:

Fifi does have promise when it comes to needlework, and I like the idea of his being able to design and make his own sissy outfits, just as I enjoy making him build his own restraints and punishment devices. Literally being in a trap of his own making adds to his sense that he deserves everything he gets. If there is a moral to his story, it's definitely "be careful what you wish for"!

It's been amazing to me this month seeing how merciless Julia has been to his poor little penis (although actually "little" might be the wrong word... a couple of times he's come home from her house with it swollen to almost twice it's normal size). Now and then I caught myself almost feeling sorry for him; but no-one understands a boy's needs better than his Mummy I suppose, and it WAS naughty of him to look in her handbag when he was little. What price can you put on a clear conscience? Anyway it's beginning to return to its normal colour now.

The Spanish Donkey he's making promises to be a lot of fun. I have a particular fondness for "endurance" punishments because they give high value for minimal effort - just strap him in, sit back and enjoy the ride. Well, I will enjoy it - Fifi won't! I wonder which he will come to dread more, the bike or the donkey?

Taking him out to the woods was the high point of the month for me, it felt so daring just abandoning him there all alone. It's true he was well hidden, but you never know who or what might be lurking in the dark. Julia and I found it such a turn-on to be sitting in a motorway café innocently chatting with the family at the next table, whilst privately imagining how horrified they'd be to know what we were up to.

Fifi's remarks about the relaxation of lockdown are interesting. I suppose he's right that as time goes on the two of us will be spending more time in company. When my friends came over it was strange to have Fifi dressed in boy clothes and answering to his boy name. Beforehand I'd been worried about not being in control of his behaviour but that's not the case at all. In the last year Fifi has been totally conditioned into submission and as a result he constantly looked to me for signs of approval or disapproval when speaking or acting. In fact I'm really looking forward to working out a set of subtle non-verbal signals so I can direct his behaviour without anyone realising. The covid restrictions may be lifting, but the sissy restrictions are permanent...!

Mummy Julia writes:

Oh dear, I come across as SUCH a sadist in this month's diary! It's funny really, because it's a side of my character I didn't even know was there until Emma drew me into her world of domination. Even now, I wouldn't describe myself as really cruel; the things I do to my son are a logical extension of his own desires.

It was Fifi's choice to be strapped down and get sixty penis smacks, with me sitting on his face to prevent him from asking me to stop. He even wrote me a thank you letter afterwards:

"Dear Mummy

I am grateful to you for giving my penis the treatment it deserves. I was a bad boy to go in your handbag without permission, and disrespectful to masturbate about you. I would still be doing it now if you and Mistress Emma hadn't taken control of me and put me in chastity. Having a sore penis and never being allowed to squirt is a fair price to pay for being your sissy slut and giving you pleasure with my tongue. Thank you for using me as the pathetic worm I am.

Love from Fifi"

I derived great satisfaction from showing Fifi off to my friend Sally and her daughter. Now they are party to the secret I hope they will become frequent visitors and active participants in our sexy activities. I suspect Fifi may be correct in thinking that Sally's own son might end up in bondage too. It would be fun having two little dollies to play with!

Fifi and Emma have both written about the end of lockdown restrictions and what that might mean for us. I am inclined to agree with Emma that a more "integrated" lifestyle will be no less exciting and might open up new possibilities for subtle teasing and humiliation of my son.

When lockdown began, it provided a unique opportunity to close down Fifi's world to the point of absolute female control. He's now thoroughly acclimatised to the role of a sissy slave in permanent chastity, and I'm confident that the transformation is irreversible.

Certainly neither Emma nor I have any intention of relaxing our hold on him - his place is squirming in frustration beneath our high heeled boots, tightly bound and dressed in frills, forever.

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