Bending over and dropping my girlie knickers for anal sex in chastity

A sissy slut doesn’t deserve to get hard while a real man fucks his arsehole!

Cross-dressing sissy in tiny blue dress and white stilettos

Locked Sissy Transvestite

Being in lockdown has given me plenty of chance to think about some of the sexual fantasies I’m yet to fulfil. The last few months have seen me tick off lots of long-held sissy dreams, most notably coming out to my ex-wife and agreeing to let her have the key to my chastity cage. And that last one has set me thinking about another dream of mine. And that dream is to be shafted by a well-hung stranger with my cock remaining locked throughout.

I have always had a strange relationship with my penis and love seeing it locked in its silver cage. It deserves to be in prison because it’s far too small to please a woman; it never used to get hard for my ex wife; and I always had to use sex enhancement pills to have any hope of achieving an erection. Of course, my dream would be to have it replaced with a vagina, but caging it is the next best thing – and I love the thought of teasing it by getting fucked while it’s trapped in its cage. Because the only thing that ever seems to get it excited is when something big and hard penetrates my rear-end.

Sissy transvestite hitches up dress to expose black knickers through nude tights

Chastity Devices For Sissies

I have had anal toilet meets with studs in the past, but not since my ex wife has taken ownership of my chastity device. She keeps the key in her underwear drawer and only lets me release my cock if I beg for it and agree to tell her exactly why I need to be released. So if I do fancy masturbating next week, my wife will want to know what I will be wearing and what I will be thinking about, reading or watching – and pretty much every juicy detail of what I’m planning to do while released. I have to either put it all down in an email to her, or tell her over the phone.

It’s humiliating, of course, but I get a real submissive thrill from telling my ex wife all my forbidden sissy fantasies. I especially love telling her what outfits I enjoy wearing and discussing with her how those outfits make me long to suck cock and get fucked by real men. These were the kinds of things I would have loved to tell during all those years of marriage when I was failing to get hard and pleasure her. She deserved to know back that then she was married to a failed sissy slut, but at least she knows the truth now and is getting some payback. Because with the key to my clit in her underwear drawer, she definitely owns me now!

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Being threatened with total worldwide sissy exposure by my unforgiving former wife

If my ex wife has any say in the matter, then soon the whole world will know the truth about my shameful sissy ways.

Forced sissy exposure by ex wife

Sissy in Female-Led Relationship

Coming out to my ex wife is without doubt the best and worst thing I’ve ever done in my life. Of course, I love that she’s been so willing to help me with make-up and is even encouraging me to date real men, but lately she has been taking a bit of a ‘forced femme’ approach when we meet together. She absolutely insists I dress up if I visit her now, and expects me to be dressed if she ever visits me; and she’s also started taking photos of me while I’m wearing my favourite girlie outfits. And she’s threatening to show them to everyone!

She’s playing on my weakness, of course! She knows I cannot resist the desire to put on tight dresses, knickers and bras – and she knows that once I’m all dolled up, then I love to pose in front of camera. But I’m not so sure about those pictures being shared with my wife’s best friend, her colleagues at work and even some of the people who know me as a man. But I’m pretty sure that’s what she’s doing with them, because lots of people seem to look at me differently now. And I even get the impression that some of them are trying not to laugh as they talk to me.

Sissy cross-dresser exposed by ex wife

Forced Sissification

One person I don’t mind her showing my sissy photos to is the hunky boyfriend she lives with since our marriage failed. He’s met me dressed up a few times now and seems to enjoy cuckolding me. He’ll fondle and kiss my ex wife right in front of me and they’ll even make little jokes between them about my tiny cock and me being a closet faggot. And I wouldn’t put it past them to actually fuck in front of me before too long. They seem to like watching me squirm with discomfort and to taunt me for being such a failure of a man!

Anyway, I can cope with my ex wife’s boyfriend being shown all my sissy photos – and I’m not going to lie, I rather like the thought that he might even get turned on by them. But since I’m very much living two lives now – a male one in the real world and a female one at home – then I do get extremely anxious at the prospect of being found out by workmates, guys at the pub, guys at the football and certain women I know. I’ve been growing my fingernails and trimming my eyebrows lately, so already lots of people are probably starting to suspect something’s up. But I’d like to keep some air of mystery about it – and not to be totally exposed as sissy, like my ex wife seems to want.


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