SISSY FIFI'S DIARY - JUNE 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 second one...

At the end of last month Mummy went away to stay with friends for a week. They all worked as teachers in the same school when I was little and this was a sort of reunion after lockdown. I was a student at the school so I remember both of them. Dana was my class teacher when I was eleven but of course back then I called her Miss Swan.

I sometimes think that the way I am is partly to do with the fact that Mummy was a teacher at my school. I think most kids can get away with acting differently at school than at home but I never could - anything naughty I did got back to her straight away and Mummy made me feel bad for bringing disgrace on her. Also, although she didn't teach any of my classes we did interact at school, and she treated me like just another student so she wouldn't be perceived as giving me special treatment. I even had to call her Miss.

Boys often have crushes on their teachers; I certainly did with Miss Swan, and some of my friends thought Mummy was "hot". So when I masturbated thinking about Miss Swan, I knew they would do the same thinking about Mummy; then the whole thing got mixed up in my head, and I started thinking about Mummy that way too.

Another thing that influenced me was a book I found once in Mummy's school bag: a Victorian novel set in a boarding school which was mainly about lady teachers caning boys. It had Miss Davenport's name written in the inside cover (that's her friend Michelle). It excited me without me understanding why. After looking through it I put the book back where I found it and even at that age I knew better than to talk about it.

Anyway the point of this is that apparently on this reunion Mummy told Dana and Michelle that I'm a sissy now, which they found really funny. The thought of them talking and laughing about my treatment makes me feel so ashamed! First Chlöe the tattooist saw me dressed up and now Dana and Michelle have been told about it and seen pictures - it seems any woman who finds out about me really enjoys the idea of my situation, especially the part about how I'm teased but not allowed to ejaculate. There must be something about me that makes them think I deserve that, and the only thing I can think of is that it's because I used to masturbate about Mummy.

When Mummy came home from that holiday I was still in disgrace about writing to Auntie Helga without asking Mistress Emma first. Before I was allowed out of disgrace they gave me another punishment. I was stripped naked except for high heels and had a bag tied over my head, filled with Mistress Emma and Mummy's worn panties. Mistress Emma put crocodile clips on my boy parts, tied to cords which were attached to my neck, knees and ankles. It meant I was bent over in a sort of crouching position and if I tried to straighten up even slightly, the clips would be pulled and hurt even more. I don't know how long they kept me like that exactly, but they took turns to thrash me with a whip called "the stinger", which is made of leather thongs. It's terrible being whipped when I can't see, because I can't tell when or where the next stroke will land. At least if I can seeing comingI can mentally prepare for it.

Mummy said the point of putting the bag of panties over my head was to symbolise my inferiority by putting my face in with their dirty laundry. Because my crime had been writing to Auntie Helga she added that this will now be known as "Auntie Helga Treatment" whenever they use it on me.

Oh, it was such a relief when my period of disgrace came to an end. I had my nice, pretty dresses back and lighter restraints for housework, but best of all I was treated affectionately again and was allowed to pee in the toilet instead of my food bowl. I resolved to be extra good so I could stay out of trouble. The only challenge was that Mistress Emma decided to be very attentive to my boy parts most evenings, stroking and petting them in a way that meant I was often very close to "squirting my mess" as she calls ejaculation. But I was very careful to warn her whenever my excitement got too much. It's very frustrating having to say "please don't make me squirt Mistress" when really that's exactly what I long for. I can hardly remember what it feels like to cum any more, it's been so long.

One day when I went to Mummy's house to clean she told me I'd need to hide, because her neighbour Sally was coming over. She has a rattan trunk in her sitting room so after strapping my arms behind my back she helped me climb into it and lie down on my side with my knees drawn up, then closed and fastened the lid. Actually it wasn't just Sally who showed up, but her daughter as well - I could see them through the gaps even though I was hidden. I've seen Sally before but not the daughter. She looked about eighteen. Mummy got them to sit opposite me and brought drinks in, actually setting the tray on top of the trunk!

The visitors stayed for maybe an hour and a half and I had to lie really still so the trunk wouldn't creak and give me away.

When Sally complimented Mummy on her home she thanked her but said some of the credit should go to her son who came over to help with chores on a weekly basis. Sally remarked that Mummy was lucky because her own son was useless around the house, to which Mummy replied that I'd been the same as a teenager, adding that it was my girlfriend who'd made the difference and now had me "well trained"; so Sally joked that perhaps she ought to find a girl like that for Marcus, to "lick him into shape". Then the daughter sort of sneered and said her brother was useless, no girl would be interested. From the conversation that followed I gathered that Sophie (the daughter) had been one of the popular girls at school but her younger brother was the awkward, studious type and "always on his computer". Mummy confirmed that I'd been that way at his age too, so there was still hope; "Emma doesn't tolerate any nonsense, believe me... and now nor do I" she added. "It sounds to me as if the two of you just need to take Marcus in hand."

For me, listening to all this, it felt like Mummy was close to telling Sally and Sophie everything about me, but she didn't do that. I think she was choosing her words very carefully for my benefit, seeing how close she could get to describing me as a submissive slave without actually saying it. She even mentioned how sweet I looked in a frilly apron, but of course the visitors had no way of knowing that's quite often all I wear!

This was another instance of me realising the low opinion women seem to have of the male sex; I couldn't help thinking that if Sally and her daughter DID know the whole story they'd probably react with as much enthusiasm as Dana and Michelle had done, in which case this Marcus might find himself in a similar situation to me. But maybe I just wanted to believe that because it would mean I wasn't the only one who deserves this. Probably Marcus is normal and doesn't think about his mother or sister when he masturbates.

Mummy has really changed towards me this month. The biggest change is that Mistress Emma told her she should let me give her tongue service. It's something I've thought about and never dreamed would really happen, but it did. I don't think I ought to describe such a private thing here but it was wonderful to be allowed to do this for her. I don't think I was very good at it but Mummy was nice and said that was just because I'm used to doing what Mistress Emma likes and every woman is different in what works for them. The main thing is she says she will let me work on it, so there is scope for me to improve.

After that happened Mummy seems to have got more strict with me for some reason. A few days after I gave her tongue service she turned up at our house with a terrifying new device called an elastrator, which vets use to castrate animals. She showed me how it works by putting a rubber ring round the testicles so they eventually just fall off! Mummy says she won't hesitate to use it on me if she or Mistress Emma ever suspect me of masturbating. Well I never do that now, but I got the impression Mummy is quite tempted by the idea of removing my balls so I still don't feel safe - what if they suspect me and don't believe it when I say I haven't? I really don't want her to castrate me, it would be awful. I hope they are just saying it to tease me.

Last time I went to Mummy's house she put me in very strict bondage. I knew when I arrived that she was going to be cruel because she had a new outfit on that made her look even sexier than normal, with thigh length boots and a bodysuit with mesh cutout parts. I've noticed that the sexier she looks the stricter she is, and that was definitely the case on this occasion. Mummy had borrowed that steel plug from Mistress: the one that opens up inside my bottom and locks so it can't come out. She put a bar through the ring on the plug, with heavy weights taped either end and explained I'd have to do the cleaning with a duster in my mouth, because my hands would be needed to hold the bar up - and to make it even harder my ankles were fettered together. It was obvious she didn't care about the cleaning at all, but just wanted to humiliate me. All the time I was like that she was watching me, laughing, and telling me what a useless slut I am while flicking my legs with her whip. I cried so much my make up was running down my face.

When I got home I asked Mistress Emma why Mummy did that to me when I've been so good lately. Mistress smiled and remarked that I still seemed not to understand women very well. She said Mummy could do whatever she wanted and didn't need a reason - although she might want to show me that giving her tongue service wouldn't earn me any privileges, but only take me to a new level of submission. Mistress says that rules are for males and women can do as they please.

The latest thing that has happened is that Mummy and Emma say I can get my tongue pierced. It was my idea because I hope it will make me better at giving Mummy intimate service. I have also had some sexy thoughts about how a tongue piercing could be used in bondage. I suppose normal males would find it hard to understand why I'd get aroused by the thought of being chained up by my tongue but for some reason I just do. I'm sending a drawing I did showing me with a tongue stud chained to my boy-bits.

I'm hoping that they'll ask Chloe who did my penis tattoo to do the piercing because I would like to see her again.

Mistress Emma writes:

Fifi had a dream this month in which Auntie Helga visited and told him he was "ready for the next step". I think that serving his mother orally marks that step and I'm delighted she and I can now share him in this intimate way. I'm also pleased he has the sense of deference not to go into details about it. I will mention, however, that Fifi was blindfolded - the general rule of "look but don't touch" is reversed when it comes to cunnilingus on one's mother.

I suppose he's right in his observation that this month I've kind of taken the "good cop" role and Julia has been "bad cop". I dare say this will switch to and fro at random, just as there will be times when we gang up on him or both go easy. It's always useful to keep the sissy guessing. Feminine power is as fickle as the weather.

It intrigues me that Fifi thinks we only bought the elastrator to tease him. I would strongly advise him not to test that theory.

Mummy Julia writes:

I totally agree with Emma's observations. My son has been on a long journey of discovery but still needs to let go of the typically male notion that he can control what happens to him. It seems to me that a sissy should serve and obey only to give pleasure, not in hope of reward. A penis is like an arrow: totally unimportant apart from what it points towards. And we all know where Fifi's penis points as soon as it's out of its little cage!

As for his childhood recollections, obviously all female teachers know their boy students masturbate about them and it's my impression that most find the thought rather amusing. I realised my son had a thing for Dana, as did she, and we often joked about it. I also recall that she visited the house once when he was doing "corner time" pressing a coin to the wall with his nose. He was so embarrassed when she saw him that he started crying, and Dana had to stifle her giggles to save him further heartache.

I had completely forgotten about that book though! It was called "Mistress of The Manor" and it wasn't really Victorian, it was just kinky erotica set in that era. I think Michelle found it in a charity store and it was passed surreptitiously between the younger female teachers in the staff room. It was appallingly badly written but gave us all considerable amusement at the time. How funny that my son found it and that it played a part in shaping his fantasies - and how interesting that he's only mentioned it now!

Come to think of it, Fifi is owed a long overdue punishment for rifling through my bag. How much penalty should be accrued on something owed for thirteen years? Let's say twenty smacks at 15% compound interest... Fifi can do the arithmetic, but by my rough estimate I think his late confession will earn him a VERY sore penis!

Putting Fifi in the trunk when my neighbours called was great fun, it felt a bit risky but that was the idea; and yes, I was fully aware the whole time that the content of our conversation would reinforce the message that pretty much all females look down on the inferior sex nowadays. But he's also correct that his incestuous masturbation marks him out as especially pathetic and punishable. Still, his mouth has proved useful this month - whether it's holding a feather duster or doing other things for me.

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