Category: sissy

The loser takes it all

Or at least, as much as she decides he can take.

Right now, I really need to know what she’s been watching on that VR headset…
That is very bad luck. I mean, whether they look it or not, sissies are technically male and males can easily go several days at a time without thinking even once.
Nice clean t-shirt, though. Always such a thoughtful gesture, when subs make an effort to look smart for their dommes, who’ve typically spent ages on their appearance.
I took an escort to a work party once, and I have to say she did an amazingly good job convincing them she was really my girlfriend. Her mocking descriptions of my sexual failures were all startlingly accurate, despite that being the first time we’d met and later all my co-workers wanted to know whether we’d got back together after she dumped me so brutally that night – and whether my balls had recovered from such a hard kneeing. What a pro.
Oh, the lesbian sex thing’s just a bonus.
Oh Lord, I pray that Annie Hathaway forgives me… but not yet.

A hard woman is good to find

She seems very confident (women on this blog often are, actually) she knows how bad it’s going to be for you. I wonder how?
Even experienced submissives can sometimes forget themselves and indulge in shockingly challenging behaviour. Just the other day, I was thanking my SO for a punishment beating – down on my knees with my tear-stained face against the floor, as you do – when all of a sudden a note of insufficiently sincere gratitude crept into my voice. Apparently. I can’t imagine what provoked me into such a blatant act of insubordination, but you can be sure my good lady didn’t deal with it lightly.
She’ll be delighted to hear the ice bucket challenge is back, but this time it’s in February, which should be a lot more fun for almost everyone involved.
The healthy diet might lead to a long life, but he might perhaps want to remember, when dealing with the supervisor or other ‘carers’, that the longer his life goes on, the worse a deal the one-off financial settlement ends up being for the institution. But I’m sure they’ll do the right thing, whatever they decide that to be. Anyway, it’s very reasonable as the food and heating bills are remarkably low, leaving his loving daughters plenty of money to spend however they like, secure in the knowledge that he is being properly looked after.
After a while he’ll be desperate to be let out – which is weird, really, because he must realise that soon after that he’ll start to become increasingly desperate to flee back inside.
Truly, madly, shallowly.

… and a couple of topical extras today, with thanks to shorty for the inspiration:

More Jutta perfection in Friday’s post.

Tears are not enough

Slam that door, slap my face.

That damn flicker. Better try to get it under control, now you’re married.
She likes locks. She likes the look of them, she likes the sound they make gently clinking inside your trousers when you’re out together…
I got lost once, Followed the wrong pair of heels… suddenly looked up and gulp! The lady was very nice, though and took me home, where she got talking to my SO and one thing led to another and… well, let’s just say I didn’t get my whipping for being lost until quite late the following morning!
He’s going to be your friend too, now.
Dommes say the funniest things. One beautiful lady once tied me to the bed and giggled sexily in my ear about how much she’d like to take my cock in her mouth and nibble it gently before taking firm hold with her hand and pumping… pumping… The silly thing must have forgotten she’d locked me in a tight chastity restrainer! But I didn’t say anything to embarass her.
In the event, she did turn up, about an hour late, with some of her friends, all wearing tight boob tubes and leather miniskirts. They got drunk and started shouting mocking abuse at all the sad little physics spods and speccy chemistry nerds sharing the stage, and made them hand over their medals, which they referred to as ‘lunch money’.

Finally, a quick note about comments here on this blog. The anti-spam thingy (to use a technical term) seems to have been a bit too cautious of late, with some commenters being blocked. Sorry about that. If you are, I think you can request approval. I do see those (might take a day or two) and I’ll always approve any that aren’t obvious spam marketers. I think once you’re on the approved list you’re fine forever but I’m not sure – the anti-spam stuff keeps having to change to stay ahead. I’d love to just switch it off, but I see the list of spammy comments it has blocked and believe me, there are hundreds every week so that’s not an option.

Divine displeasure

Very different from my SO’s attitude – she likes to hear about how much it hurts.
Bit pointless to book a heavy session and use a safeword anyway. It’s like…. I dunno, going to an expensive restaurant and only eating stale bread with water. I mean, I’ve done that, obviously but…
She’ll definitely tell them off: she’s very cross about what they did. But she has a sweet, forgiving nature, so don’t be surprised if she goes back on her intention to ban all of them except Tony. I mean, that is a lot of cock to deprive herself of, and it’s not as if it was really such a big deal, right? And there’s the question of fairness to them to consider too…
You can have one of his trainers as well, if you fancy a threesome.
It’s ridiculous you can’t have men’s brains fixed to stop them being annoying… seriously annoying, I mean, obviously. We need to fund the NHS properly.
Lots of things to think about… and plenty of time to think, too.

At my lady’s pleasure

You didn’t think there was anything better than an orgasm, did you? Apparently you were wrong.
It’s good she’s taking the trouble to be so reassuring.
He’s always been harmless, but when she first acquired him, she decided to make sure.
I’m sure she knows exactly what she’s doing, so best not to interfere.
Most customers only make use of this service when all the machines are in use, but she just went straight for it. Of course, it’s a lot cheaper.
One of a series of ‘Cooking with Mila’ videos. ‘Housework with Mila’, ‘Gardening with MIla’ and ‘Money management with Mila’ all take a similar approach, I understand.

It’s not her fault

It’s yours.

Fortunately she’s not easily embarassed – you can look quite absurd and be made to do lots of humiliating things before she begins to experience the least twinge.
Many women secretly prefer didoes to their male partners’ cocks. My SO is more open about it – says the dildo is even a better conversationalist, quite apart from the sexual aspects in which I’m obviously not a contender at all.
Dream job – and you’ll get to do twice as much of it.
The fivesome’s scheduled for next week, when Lucy’s cousins are in town too.
Gravity will do most of the work. All you have to do is suffer; and that’s easy enough when you’re in pain.
As if this sequence of photos (others from which I unfreely acknowledge I have used before) was not wonderful enough, it actually features twin sadistic Margot Robbies. I mean… why would anyone ever need to make another movie, about anything (except movies starring Mistress Annie, obviously).

Amorous anxiety

Passionate love should always come with a twinge of gut-wrenching fear.

Sometimes it’s best just to spend a whole session practising the one movement – exactly the same punch, on exactly the same spot – over and over again. Obviously, you’ll need not to move, but don’t worry if you find that difficult – she has some things to help you stay firmly fixed in the ideal position until she’s finished.
My SO can be a bit forgetful, too. Can you believe it, three times now gone home leaving me me tied up in a gay club and completely forgotten about me until the next day? Of course, it’s not her fault: it’s mine. That’s a basic principle of our marriage.
Oh, I expect she’s got nothing to worry about.
No one can humiliate you, unless you humiliate yourself, as a wise woman once told me.
Men who enjoy looking at women in tight outfits should try wearing something restrictive permanently.

Lovely Cruella shoot. Go buy the original magazines!

Don’t worry about something bad happening to you in the night, as you hang there all alone. I’m sure there’s nothing out there that’s half as terrifying as Gillian.

She walks in beauty, like the night

She’s right, of course (as women do tend to be in my experience). You can only feel frustrated while you retain hope.
Many rich man marrying younger second wives worry that they’ll be reckless with money, but in this case it does look as if he’s married someone capable and willing to exercise strict financial control.
Of course there’s nothing wrong with a sissy having opinions, as long as they are sensible opinions derived from someone else – someone without intellect-destroying Y-chromosomes.
The problem is, she’s a perfectionist, but really, why should she have to give up on the ideal of perfection? Looks to me like she’s determined to keep trying, despite these setbacks, which I find admirable.
And that’s a sin.
Typical selfish male behaviour on maggot’s part, there, not even managing to remain alive despite the two ladies having a clear use for him at least for the next hour or so. But as things turned out, the resulting photo-shoot went really well – in fact they resolved to use dead slaves more often, as they’re less annoying.

A classic from Cruella. And you can now download the originals, the stories in which are no less deliciously dismissive and brutal than my caption. Wonderful stuff.