Things I’ve learnt – and not being ‘a man’ by sissy jessie

Over the many years I’ve been lucky enough to be owned by Mistress Virago, I’ve enjoyed too much to ever mention… And it would take a lifetime on my knees thanking her to even try to adequately showcase my gratitude.

But her recent post on this wonderful blog about ‘courtship’ and all of the horrible connotations that brings up has got me thinking about the other elements she’s brought into my ‘in real life’ persona. As she says – sissification and ownership isn’t just about sashaying into a pretty dress (or being consistently degraded in my everyday life) – it’s a lot about learning, and translating what she teaches and reinforces in me and her other lucky sluts.

When we first ‘met’ I was an average boy. I flirted inappropriately with colleagues, snogged girls in clubs, masturbated over traditionally hot pornstars getting cum facials on the internet and came often several times a day. I had dabbled in being a submissive, stealing panties and visiting the occasional dominant – but I was very much a man. “How fit is she?” and other derogatory put downs as I aimed to live the life I wanted, grab my pound of flesh – and let’s face it… Enjoy myself! (because with the tiny thing I’m packing, my conquests certainly weren’t getting any pleasure out of what I was offering!)

Nice guy, very bad sissy

I was regularly described as a nice guy, and I guess I was… But underneath I was a pathetic submissive, and a very bad sissy. Mistress persevered with me, buying me gorgeous gifts and showering me with affection and attention, but oh so often – after graciously allowing me to cum at the end of a particularly fun session, I’d lose the plot. Switch my phone off and go back to my masculine ways. Sure – at this point I was starting to learn… Being a little less overtly masculine and thinking a little about my responsibilities. We also had a LOT of fun. But I wasn’t a good sissy. Wasn’t a good submissive – and though I am, and always have been, a beta… I was allowing myself to forget what Daddy was teaching me. Sure – by day She was allowing me to strip to my panties and edge in the workplace toilets… But by night we (my pals and I) were out, snogging, drinking, leering. A classic, useless ‘man’.

Chastity and conditioning to help reinforce change

So, Mistress did what she had to do. Tightening my chastity. Keeping me locked for long periods of time, and started to move my sexuality around her desires. Plugging became more common, with specific scenes of porn I was allowed to watch. At one point she [being the most creative and inspirational person on this earth] locked a pair of her used panties in a bottle of fizzy water I regularly drank, until I couldn’t help but get a sexual rush whenever I was in that drink aisle in Sainsburys. My sexual conditioning became so intently linked with the toilet (humping them/ dressing in them/ edging) that I couldn’t visit a public toilet without being intensely turned on… At one point She even gifted me with the opportunity of naming my work toilet Sasha and having her as my girlfriend – complete with sexy times, whispering sweet nothings to her and cleaning her every night before I went home.

And it changed me. Cutting off my stupid male need to ‘jerk and go’, reinforcing the genuinely pointless nature of my clitty. Showering me with love and discipline and allowing me to focus on what pleased her. Kindness, compassion, politics, the history of the women’s rights movement and the fact that it wasn’t enough to just standby. That it wasn’t enough to say, ‘yeah’ Equality is great’ without actually doing anything about it. Because the things I was loving, and consensually drinking in were an option to me. A joy. The depraved desires of my darkest fantasies. But other people were being ritually humiliated and downtrodden every day of their lives – and they hadn’t asked for it. Hadn’t wanted to be touched, manhandled, slapped, dressed like a slut, fucked in the mouth, forced to clean, fondled, talked over. More than that – they hadn’t been loved. Hadn’t been able to stop at the end of an intense session and switch off, all happy and glowing and safe in the knowledge that it had been the shared desires of consenting adults.

Doing better every day – as a sissy and a person

And her teachings. Her kind words. Her discipline has taught me everything! Made me a better person. A person who is at least starting to learn. Sure – I’ve a million miles to go (as I believe 99% of men do), but entirely down to Mistress Virago I’ve been able to make small changes in my personal and work life to make things better. To try and understand that my stupid, fragile ego is there to be challenged. If a woman tells me I’m wrong. To listen and not answer back. To understand the outrageous privileges of my upbringing (being white, male and middle class) and to do my best to battle them – and do something about it. To accept myself as LGBTQ+ and trans, and to start to be really proud of it.

Twice this year in my work life, Mistress has told me she’s proud of what I’ve done – and for all the thrilling fun, sexual humiliation and downright wonderful times we’ve had together… Those words from my Owner, my Daddy, my Muse and my Goddess mean more than anything. Because, put simply, I know I would have never done those things if it wasn’t for her ownership. Her guide and her patient and kindly dominance. Put simply, Mistress is always right. She knows me better than I could ever possibly know myself and I love her.

Gosh – when I started this short essay (sorry for all the words if you’ve got this far) – it was intended to be a list of some of the things Mistress has taught me. But in some ways it feels a bit silly to say ‘this is the right way of thinking’ – when I am, by my very nature, exactly the last person to give life advice… But I do hope you’ll forgive me, dear reader, for having a go to do just that anyway *giggles*

Stand up (or kneel down) for what you believe in

Rules of living from a (former) straight, white man. Just what you want to read eh 😉 But these are just some of the most important things I’ve learnt from my wonderful years with Mistress Virago – and I’d love to share them, if you don’t mind ❤

–          Don’t think with your cock

(Or in my case ‘clitty’ as Mistress has termed my fun-size sissystick) – My virtually ever-present chastity has been one of the most important things in my life for the last few years, and although it’s hard – it has allowed me to focus on better things, being a good sissy and trying to focus on positives in my everyday life. I genuinely think, much like the excellent Green Party idea of an experimental 6pm curfew for men, some level of male chastity should be mandatory – with it used more heavily for anyone who shows signs of sexual aggression. Tags are common, right? Why not enforced periods of chastity?

–           Your industry is filled with awful people

It really is (almost certainly) and we need to stand against it. The fact that someone as powerful and brilliant as Mistress Virago has been patronised, bullied and scorned by male bosses is proof that it’s happening. Across the world. Across your industry. And we need to do something about it. I’m lucky enough to work for a strong and brilliant female boss, but a co-worker of mine right now is being treated like shit by male colleagues who bully and belittle her while they take the best jobs, despite the fact she’s brilliant, talented and able. So I’ve taken a stand, and spoken to my boss. To add my voice (as pointless as it may be) and to ask her to have a look at what’s going on. It’s a tiny example, but yet again inspired by Mistress Virago and her wonderful teachings.

–          Eat your own cum. Yum Yum Yum!

*Giggles* – it may be a very personal one this, but it was a massive barrier to break for me to eat my own cum and Mistress patiently guided me through it, as I failed consistently and pathetically, snapping back to that male moment as soon as I’d spurted my little sissy goo into my hand. But she persevered, and now I relish the taste of cum… It’s made me more cock-hungry (which pleases Daddy), means if I ever am permitted an orgasm I absolutely associate any pleasure I derive with that lovely taste – and, of course, it’s a suitably sissy activity! For anyone who’s ever watched sissy porn, the last thing you want is a sissy struggling to eat their/ someone else’s cum. Oh no! Be like Sasha De Sade and savour that thing. If a kind gentleman cums in my face, you better believe I’ll be so SO grateful. If I’m ever allowed to suck up cum from the floor this sissy will be beaming for weeks J It was a big barrier for me, and I feel Mistress breaking that down for me made me a much better sissy!

–          Accepting my failures:

Everyone fails. I do more than most. And we must accept them, and work through what we are good at. Long ago, Mistress taught me I was no good in terms of sexual stamina or size (or girth) so she set about teaching me that I could serve, be useful domestically and that I had a very good tongue when it came to going down on someone – as well as a sweet sissy nature that she could work on. So her decision to lock up my useless clit and focus on my better assets has allowed me to flourish, and become a slightly better person than I was. This year I aim to suck a lot more cock (safely and sanely – I’m not hanging round the toilets waiting for inebriated doggers ;-)) so that I can improve my technique and be a willing and pleasurable mouth for any guy she chooses to use me. Why worry about my orgasms, when I can provide good ones for others. A note actually – if you are based in East London and would like me to pop over for lunchtime blowjob practices, please do get in touch with Mistress (search MistressVirago on Fetlife). I would love to have someone to practice my technique on (safely, of course).

–          And finally, Mistress is always right. Not usually, or figuratively. Always.

Like, every time 😀


sissy jessie

A word from Mistress Virago

When I asked jessie to write a blog, I wasn’t sure what I’d get (in a good way). Her words and honesty in this blog caught me by surprise (and made me laugh in places). But the most important point that jessie makes is that lifestyle D/s and life aren’t separate things. I’m proud that jessie is sensitive to the wider, real-world struggles around equality, feminism and LGBTQIA+ issues, and takes action where she can.

I suspect there are other lifestyle sissies out there, quietly using their ‘male privilege’ to do the same. If that’s you, leave a comment and tell us what you’ve been doing.

2 thoughts on “Things I’ve learnt – and not being ‘a man’ by sissy jessie

Add yours

  1. Mistress Virago and her beloved sissy jessie,

    This is a very interesting article. There has been an absolute abundance of “Lads lads lads” culture in my life. Mainly professionally, though I too have certainly fallen foul of standards that I now try to abide by.

    Sadly, there aren’t very many women in my industry, although that is starting to change in more recent times. Minorities too, have always been under represented, in what must have been the last bastion of the oppressive, overbearing, entitled white male. Toxic masculinity was the daily staple. Bullying all those that were different.

    I have worked in my industry for twenty years. Since getting into a position of trust and power in the last 5 years or so, I have made it my personal mission to ensure that those who aren’t the loudest, funniest or brashest get the plaudits they deserve. As someone who is fairly mild mannered and meek, I have been tired of being looked over for those with the “Lads banter”, who amuse all, yet work the least effectively. Usually, these same people are the ones that are the most intolerant. Be it homophobia, racism or of course, sexism. I’ve found myself being very effective at shutting out those that have an opposite and backward mindset, and ensuring their ways are highlighted, discouraged or dealt with more severely.
    Finally now, in the last year or so, has my employer hired more women in “non-traditional” female roles and it’s been great seeing them contribute and thrive.

    However, as I said, I am white, male, middle class and a part of the problem. I am aware of my privilege but far from perfect. Thankfully leading females in my life over the years have steered me towards betterment but I know that I have not reached the end of that road yet. And I probably never will.

    I hope to continue to improve and to use my privilege to either help those that need it. Or ensure those that don’t need help, just get the opportunity they deserve. Whatever their sex, race, religion, creed or sexuality.

    Kind regards


  2. Thank you for sharing your wonderful experience. It gives hope to all of us out there. The part about tightening chastity and sexual reconditioning was particularly interesting to me. Such power and dominance is intoxicating. Carlsberg dont do Mistresses (sissy trainers) but if they did….;)


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