Sir's Diary

Sir's Diary September 2021

Preface:

My subbie likes her daily tasks. I keep trying to take a step backwards from giving them to her, knowing full well that she has a life, kids and dating to contend with. But something draws her back each time. Something evocative. Something addictive.

Something emotive.

(By the way - all of this is still a true story!)

Monday 21st

I woke this morning wondering if I was being too harsh on subbie. Her body is now attuned to regular orgasms and she is being so good. She agreed last night to give herself three away from the house with none allowed at home, but worry if this is possible.

I know that she has a lover and is probably confused about her online relationship with me. I was helping her quit that disgusting habit but having seen her pictures, she is a hot girl and far better looking than I had imaged. I wish I lived closer lol.

I keep thinking and trying to step back to let her make her own mind up about the direction she wants her life to take but think she is loving the sub/Dom aspect of our relationship and is becoming addicted to daily tasks. Maybe she will want the physical one with her lover and want to continue a remote one with me? I don't know how I feel about that. As long as she doesn't smoke I suppose. If she did, I would be so fucked off with her - a destruction of everything we have worked together towards.

I love creating the daily tasks and hearing about them from her point of view. She has turned me on more often than I will let on to her as I am trying to maintain an aloof Dom profile but I wake with a very stiff cock. I would love to see her in some of the poses that are her tasks but how do I get across to her that I would love a picture but not necessarily one of her open intimate bits!?

And how do I convince her that she doesn't need to worry about her pictures? I have no need to keep them, but they do inspire another fun task for her. Seeing her body makes me wonder how it would look doing certain things. How it would look to her. I don't think she has thought about herself in that way before.

Hmmm.

I tried this morning to take the step back again so as she doesn't need to be confused about this bloke from across the other side of the country. I left her with an ongoing yoga task which she has promised to do daily now. I put this in due to the fact she has told me she is now eating more chocolate than usual. Told her that if she was alone to do it naked and in heels to make it more sexy. (I wish I could see her stretching and flexing in an overtly sexual way. Can only imagine how it would make her tits shimmer or swing enticingly and how pert her ass would look pushed into the air. My cock is hard at that thought.)

Mid morning today though she sounded like she needed another hit, so to speak, and I had an almost pleading txt asking for a motivational task.

I set her a 'Wall Wait' in the toilet, stark naked and I know this turned her on as the toilet is quite surrounded by people at all times.

I decided to oblige her needs so now her task on Tuesday is to take her knickers off while driving.

Simple.

Effective.

Fun.

Hopefully she will do it in heavy traffic whilst stationary so as her heart will pound and she will have the sense of public nudity but in a safe controlled way. It should bring her further out of herself and make her more confident that she is a very attractive woman. I would love to see her all demure, dressed and professional from the waist up but open, available and fuckable from the waist down.

She was txtn an appreciation of being dressed and used as my maid yesterday. A horny thought but she would need some much sexier footwear. I can just imagine those breasts trying to escape a little pinny and that full mouth being used to clear my own build up of stress!)

Anyway she now has promised to do yoga naked in heels which I would absolutely love to be a fly on the wall for, and remove her knickers whilst driving home Tuesday but it was a knee jerk reaction to ban her from cumming...

I am going to recant that.

Sir is going to allow her to cum at home, but to promise to try to cum out too. I know this is going to sound woolly but i think this is a fair compromise.

I will tell her tomorrow.

I will try to once again take half a step back to give her space to decide what she wants. I don't want to force my thoughts onto her - she is a busy woman...

but the subbie

whether she realises it or not

is always in the driving seat.

Tuesday 12th

Reflecting on today and subbie has told me she completed her task with an exhilerating outcome. Removing her knickers whilst driving turned her on more than I think she originally thought it would.

She sent me a picture of herself in a skirt earlier in the morning and then later on a selfie of her open mouth as though available to give a blow job. I was holding a meeting at the time and missed a step when I saw it. I suppose I shouldn't have had my phone available but I feel a certain compulsion for obvious reasons.

I have to admit, I was very turned on imagining (as was her desired outcome) my cock pushed deep inside her mouth whilst we were perhaps together at work. Best we don't work together. I can't imagine much work getting done. Can however, imagine instructing her to stand in the toilet naked and facing the wall, and wait for

I sent her some extra messages whilst I believed she was playing with herself and hope they helped her over the edge.

I'm glad I recanted on letting her cum at her own home but think I need to train her to achieve orgasm elsewhere.

I have ideas for further tasks but need more of an idea about some of her routines and clothing options. For some reason, despite having an extremely graceful and attractive chest, she insists on wearing almost turtleneck clothing.

How cool will it be when she can show the top of those amazing breasts within a fantastic cleavage.

My only sadness is that ironically, she is going to dressing for everyone around her and not for me.

Oh well.

Roll on tomorrow's naughty task.

Wednesday 13th

Subbie sent me pictures of all her skirts last night. I like that she has a range and that she isn't afraid to show her beautiful legs off in shorter denim. One of her skirts has buttons all the way up and would look amazing I think with the lower half of them undone offering a glimpse of inner thigh perhaps as she walks.

I am seeing her face more often now which is putting a personality and giving her Dom tasks a reality, and this morning she sent me a picture of herself on all fours. One tit hanging open and exposed and looking very needy with her hair covering the other and shading the view of her pussy between her breasts. Very erotic. Am wondering if she had planned the shot or it had happened organically. Whichever, it was very arty and arousing. Made me wonder what her body would look like from different angles and whether her previous lovers (or herself) appreciated it? Her breast has a voluptuous round look to it and lovely colouring around a very proud nipple.

Nice to see her on all fours. There are a couple of other subbie poses she has yet to see and practice which are only a short step from basic yoga. If she wishes to continue her training, then they will be slowly introduced. She can already produce 'Wait at Wall' and 'Kneel Exposed' perfectly like an excellent, well behaved slave.

Her task today is to wear a skirt but to never sit on the material. A tough ask but she is capable. It means that she has to think about Sir and her obedience for most of the day. It will probably exhaust her and might mean a suction dildo moment in the bathroom tonight before bed.

The point of all this originally was to occupy her mind from being silly, but I honestly think that she would never go backwards now. I do feel proud of my good girl.

Reading her diary entry, she seemed to have thoroughly enjoyed her knickers removal task. I personally hope that that was in some small part to being under direction to do so from a mysterious, stern dominant, wearing total black, as well as the physical naughtiness of doing so whilst driving. That concept could be explored in future tasks and I believe she likes her own taste, telling me she sucked her fingers clean this time. Maybe I could get her to masturbate over a saucer and then told to lick up any residue moisture.

Many many thoughts mulling in my head right now.

Thursday 14th

My good girl spent yesterday braless and in a G-string and making sure that every time she sat down, she didn't sit on the leather of her skirt.

Wow!

That would have taken some dedication and commitment if she has done it properly and from every communication from her, it seems that she did take it seriously and did it honestly.

I told her that if she was with children, then to either remain standing or to kneel and to only sit on the material if she had no other course of action. (There is no way I am creating problems for her job or upsetting anyone else.)

She sent me a picture of herself seated at home before she left that morning, her quite longish skirt ruffled up at the back and exposing a lot of a well-toned and shapely leg. I left her the choice of skirt despite requesting and receiving pictures of her possible wardrobe the previous night and was intrigued at her choice of the long leather one.

Having warned her already that there was another quick task halfway through the day, I instructed her to add the word SUBBIE across her pussy in drywipe. This I think caused her a little bit of a moral dilemma. She is enjoying the sub/Dom scene remotely as we are but worrying that she is being redefined as a sub from the confident but staid, buttoned up young mother always with sensible shoes and constant hiding of her figure.

The problem for her now though, is that I think I have inadvertly changed her drug of choice from cancer sticks to the sub/Dom scene. We discussed how far it went and I think she is now more aware of its limitations; aware now that there is extremely limited (if any) pain involved and everything is consensual, safe and sexy rather than worrying.

She wears the most unflattering cardigan for work. I have an idea for tomorrow's task which is going to jangle her and test her obedience. I have decided she is to remove all clothing underneath the cardigan and to go shopping on her way home after work

Friday 15th

Well, yesterday didn't start the way I had expected. I had told her that she had until 9:30 pm to cum and after that, she was to go without, no matter how wet, horny or desperate to cum she was.

And then I heard nothing.

First thought was IT problems or out with friends or a hot date or just family issues causing her to alter her headspace from being an obedient subbie to responsible mother.

As it transpires, she had managed to make it in time and actually given herself three massive orgasms before pretty much passing out straight after, with the excitement of the day still tumbling around in her head.

I felt quite humbled actually.

She has since been honest in telling me that she had forgotten a couple of times during the day to lift her skirt before sitting down and had to spring back up in order to remove it surreptitiously. Driving was a pretty cold ass affair as her car's leather seats didn't offer much in the way of warmth to sit on. I can imagine that her pussy lips would have gaped either quite happily or in shock.

I am pleased she has been so honest with me. It was a tough ask and one I am going to repeat with her with my choice of skirt next time. She had chosen a longish leather one for herself, most likely because it ruffled up easily. Her shorter ones look a little tighter on her thighs and harder to raise and lower. This might make it more of a naughty weekend task.

She had had further thoughts too about her 'self decorations' and has suggested that with her arty flair, she was happy drawing flowers and such like across her pubic area. I did mention that in time, I would like to see what she produces after that instruction.

Halfway through the day she was ordered to pull her jumper up and to take a selfie of whatever she had underneath. I think she was relieved to be wearing a bra and that it was a very attractive leopard print creating a very impressive cleavage. A good waist too, by the obvious hint of it. She does have nice teeth too - thank goodness she is being sensible with what she puts in her mouth. If she needs that amount of 'oral comfort', my cock always enjoys that particular part of a woman's anatomy. I could guide her head with my hand on the back of her head.

It appears that the shopping trip was a total success. She had felt her tits taking their shape through the wool with the weight of them moving really erotically and from her vantage, she was really aware of them swaying and bobbing.

She had asked a young guy to reach something off a top shelf and wondered if he could see? She then apparently smirked and thanked him which felt very naughty, no doubt holding his eyeline but aware of his desire to look down at her body.

At the checkout she deliberately required assistance and while waiting, watched herself on the self-serve video, then revelled in the attention paid by the overly helpful store assistant.

I do hope she didn't touch the belt tie holding the cardigan closed. Wool normally starts to work itself open, and the original idea was that she had too much in her hands to stop it, hopefully creating a lot of excitement and a little bit of fear.

I think that by the time she got back to her car whilst carrying a couple of bags of shopping, her cardigan had started to gape quite considerably. The fact that she could see her breasts more openly, I think, turned her on a lot. She was concerned about running into someone she knew but secretly, I think she had been looking forward to it.

I wish I knew more about her wardrobe options in order to be more inventive with my tasks. We chatted about sex toys earlier but there is just as much eroticism to be had with knowing her wardrobe and having an inventive mind.

Saturday 16th

Yesterday I sent her:

"When you do your yoga this morning, naked and in your heels, set the phone camera for a 10 second shutter and position it and yourself to take a side shot of yourself. Make sure you get your whole body in a stretching pose.

I should be able to see your stretched elegant body, how it looks in heels, your flowing rich hair, a hanging gorgeous breast, and a smiling face."

Fuck.

Getting this picture back was an eye-opener. She has the most elegant and feline looking body. So much muscle definition in her legs and her oblique muscles are amazing.

A subtle soft curve of belly and extremely gorgeous womanly hips. No wonder she looks amazing in leopard print. She definitely needs some leopard print stiletto heels to go with her bra design.

Trying to keep my mind on work after seeing that was a challenge in itself.

I had the idea ready for her day at work, so after that I instructed her to wear lipstick for the day.

To any other woman, this is not such a submissive thing to do but with my good girl, I believe that she doesn't spend that much time regarding herself or believing in her attractiveness. So the idea was that she had to maintain it throughout the day, periodically finding a mirror and to spend a minute watching herself administer the smoothing stick around her lips, opening her mouth as women do. It would provide her with the oral comfort I know she craves and also reinforce to her the beauty of her teeth and create encouragement to continue her journey of self discovery.

She has a fabulous mouth and very full lips. Since she has had her teeth whitened too, her mouth is very much a focal point of her body.

I am hoping that with a day constantly colouring it with, hopefully quite a bright red lipstick, she will imagine it being kissed and her mouth used to fully stiffen a cock before turning herself over and begging to be fucked.

To please me however, she not only coloured them red, but glossed them too. The picture I unexpectedly received from her showed an extremely attractive, exciting MILF in the prime of life and ready for passion. I had a hard time dragging my eyes off her image to return to my work once I had seen it.

She had a lunchtime task of course. I instructed her to remove her top clothing and to rouge her nipples. This should involve a heightened self awareness of her beauty and hopefully a general feeling of sluttiness whilst she took the 'Wall Wait' pose as though waiting patiently to be used or for a fuck.

I cannot picture the toilet layout but it would be amazing if she was standing facing a mirror and watching her breasts shimmy and shudder with her shift in weight, the tips gloriously coloured a bright red and offering a hypnotic allure.

The pictures I received in receipt of the task, fair to say, were amazing. She has the body of a much younger woman, and though she has had children, she has most obviously escaped any long term effects. The rouged nipples were especially erotic and her belly really showing a level of fitness I hadn't expected. Is it the yoga toning her up? She has only been doing it for a week. Maybe I find a more advanced class on YouTube for her to follow considering her excellent body condition.

I feel that she has had a fair few erotic experiences this week and I would imagine she needs some downtime now.

Maybe she will use the idea of sticking her suction dildo to the inside edge of the bath and then remaining on hands and knees to rock back and forth on it as gently as possible to prevent the water sloshing out of the bath. To my mind this will mean she will have to have the slowest and warmest fuck concentrating on all the physical stimuli as well as recalling her progressively more public experiences. If she squirts, then she will squirt harmlessly into the bath water.

I will set this as a personal choice task. She has been an amazing subbie this week and I worry about pushing her too far too quickly. If she accepts, she knows the words to use.

Sunday 17th

I know that my good girl has a family and know that her children are around this weekend. I thought that she should have a weekend off from anything too risque.

Instead, I gave her the task of remaining in her denim skirts for the weekend, without knickers and her brown heeled shoes whenever she left the house. Goodness knows she needs a few new pairs to wear. The idea here is to see what top she would pair with it and how sexy she would feel.

Would she just wear a blouse or the cardigan again. Would she swing free beneath? Would she wear a bra and a low cut top in order to show her considerably quite impressive cleavage? Would she be daring enough to own anything remotely cropped? And wear it?

I know she was with her kids but lots of women do and still dress to please themselves, happy and appreciative of positive attention while feeling good about themselves. Life does not stop with children.

I think she has spent far too long dressing so conservatively that most people would look at her and not realise that there was a hot, exciting, red-blooded, passionate woman beneath. Gorgeous and full bodied but with that layer now of obedient, slutty submissive and the wettest pussy with the capacity for such squirting.

She tells me that her work colleagues have made a few comments to her about the lipstick, but she must understand that it is human nature to notice and pass comment when something is different. I would suspect that she is walking more upright and proud than usual and that can be unsettling for other people used them being in 'their place'. Lips too, offer clues about their owner, whether they are aware of them doing so or not. Make up gives a woman a powerful demeanor, their lips now as emphasised and as coloured as their pussy, and when lips are parted showing the glimpse of their white teeth behind, it giving them a powerful and confident allure, happy with themselves and their body. Not someone who can be bullied.