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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I’m beginning to regret coming out to my ex wife as a knicker-loving, cock-hungry TV slut

Oh, the horror as my ex wife takes an increasingly strong grip on my transvestite transformation!

Cross-dressing sissy red knickers upskirt

Dominated Sissy Husbands

I’m still not sure how I plucked up the courage to tell my wife I’ve been cross-dressing since she left me. But I’ve been doing a lot of online sissy exposure in recent months, so I think it was in the back of my mind that she might accidentally stumble upon something. And so I invited her round for a glass of wine and then showed her a couple of my girlie photos. And she burst out laughing, then gave me a hug – and told me that it all made perfect sense.

Now I wasn’t really sure what she meant by that, but I didn’t need to ask for an explanation, Because no sooner was my cross-dressing secret out in the open than she was hitting me with some proper home truths. She started saying how I’d always been quite effeminate and how my tiny dick was never much use in bed. And she even said she’s often wondered if I was a closet gay, due to my total lack of a real man’s sex drive, then she started to talk about her new man and how he was much bigger, butcher and manlier than me in every way.

Limp-dicked sissy transvestite swallows black dildo

Sissy men in knickers

Of course, hearing that when we were married would have been absolutely devastating, but the girl in me quite liked being told that I was naturally effeminate. But in some ways, it lulled me into a false sense of security, because I then agreed for my ex to come back the following week and meet me in girl mode. And that’s when she started to get a bit bossy and to start to take control of my feminisation process.

Yes, ‘bossy’ is definitely the word! Not only has she been telling me off for wearing dresses that are way too short and revealing, but she’s also put me in chastity and has taken ownership of the key. She’s also threatening to take me out for the night with a few of her female friends; and she’s even joked about me watching her having sex with her hunky boyfriend. She says she wants me to see what a real man looks like when he’s fucking a woman. And if I like what I see, she is even talking about setting me up on some dates with men.

So, it’s all got a bit weird. Because, yes, I’m glad to have got some help with make-up and things like that, but I never dreamed she would see this as some sort of project and want to take full control in this way. And am I happy with that? Er, well… I really don’t know.

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Shrinking my already tiny cock further with the aid of a padlocked chastity cage

My cock is such a worthless and pointless piece of meant that it makes perfect sense to lock it up and throw away the key.


Cross-dressing sissy with caged dick


Small Penis Humiliation

With every passing month I get more and more excited by the thought of eradicating all traces of my manhood. It’s pathetically small and limp, anyway, and is utterly useless when it comes to pleasing women, so I’m now liking the idea of shrinking it as small as possible. And to assist with this, I have recently purchased a padlocked silver chastity cage online. I have been wearing it under my knickers for a month now and have denied myself erections and orgasms throughout that time. I have also done something rather bold and daring – I have handed the keys to the padlock to my ex wife.


Silver cock cage for limp-dicked sissies



Sissies locked in chastity

It took me a long while to pluck up the courage to tell my ex wife about the new me. I thought she’d find it quite hard to accept, but it turns out she sort of knew along – and she now gets a great deal of pleasure seeing me transformed into a sissy princess. She has even helped me out with my make-up a bit and is apparently telling lots of my old friends about my kinky habit. I think she rather likes the thought of causing me shame and humiliation; and she recently told me about how my pathetic cock size had been a running joke between her and her female friends for years.

And I guess that joke will get even funnier as my silver metal cock cage helps to shrink my cock, helped along by a few of the female hormones I recently started to take. When I first showed the cage to my wife, she made a joke about how it was the first time she’d ever been able to notice something bulging through my underwear. And then she immediately texted her new hunky boyfriend and showed him a picture of my limp caged cock poking through a pair of pink knickers. She’s getting really quite bitchy and strict in a way, but the sissy slut in me is rather liking this version of her.

Anyways, the cage is comfortable to wear for long periods and you can still go to the toilet wearing it – as long as you sit down like a lady. I’ve tried a few of these things over the course of the year, but this is the nicest one so far. The silver metal matches most of my jewellery and kills any hint of a manly bulge stone dead. You can buy it from fetish store Honour.


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