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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Stretching my anal capabilities with a 17-inch dildo and begging my ex-wife for a strap-on session

Sex is no longer about my tiny manhood – these days it’s all about my cock-hungry arsehole.

Cross-dressing sissy in tight mini-dress

Sissy Anal Training

My ex wife came round with a surprise present for me quite recently – a present that confirmed her increasingly dominant nature and showed just how much fun she appears to be having in helping with my feminisation. I had already let slip to her that I rather liked using dildos and vibrators to pleasure my anus, but I wasn’t ever expecting her to go out and buy an anal sex toy for me. And certainly not a 17-inch Dick Rambone dildo! Yes, SEVENTEEN-INCHES of big thick dick!

‘This is what a real man’s cock should look like,’ my ex wife told me, as she handed me the dildo and saw the startled look of wonder in my eyes. She then said it sort of made sense to her that I was now using anal toys for pleasure instead of trying and failing to have sex with women. ‘After all, it’s pointless trying to do anything with that tiny little thing in your knickers,’ she teased me, ‘so I’m glad you’ve finally found your true erogenous zone.’ Then she patted my bottom to hammer home the fact that my true erogenous zone from this day forward is the sissy hole between my smooth-shaven arse cheeks!

Sissy transvestite exposed in tiny frock

Dildos For Sissies

I was tempted to ask my wife to actually use the 17-inch dildo on me, but she had to hurry off that evening. So, instead I pulled my knickers down, squirted lots of anal muscle relaxant up my arsehole, greased up the dildo with loads of lube and then slid it inside my pliable ring. And I was amazed by just how easily it slotted inside my back door hole – and also by just how accustomed my arsehole has become to taken giant lengths of prick. And though I didn’t quite take the dildo’s full-length, I must have inserted at least 12-inches of prick, then I slowly pumped it back and forward till I was overcome with sissy anal bliss.

And having loved the dildo, I’m rather hoping that my ex wife’s next present will be a strap-on harness, so I recently sent her a cheeky email with a link to the ones available from Honour Fetish Clothing. I can think of nothing more horny than the thought of bending over and feeling my ex wife fucking my arse – and if she fancies bringing her new boyfriend along and turning it into a spit-roast session, then that’s totally fine by me. Apparently, he’s almost as hung as my new dildo, so I’d love to have his meat in my mouth while my ex-wife screws my anal hole.


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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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A teasing tale of one married sissy’s destruction at the hands of his dominant, sex-starved wife

My review of the new hardcore sissy novel by T-girl author Chantelle Cage.

Cross-dressing sissy in tiny green dress

Sissy Sex Stories

I have always been an avid reader of both adult magazines and erotic fiction; and I love few things better than curling up in bed with a copy of X-DRESSER MAGAZINE or an erotic tale of forced femme and sissy training. And I love it even more when I can clearly identify with a novel’s central character, which is definitely the case with the character of Jodie in SHAMED SISSY SLUT by Chantelle Cage. He is a man who has a passion for wearing lingerie and stockings, but really not much more than that – until his wife discovers his secret and takes control of his fetish, pushing it further and further, till it spirals totally out of control.

My early experiments with cross-dressing sound very much like the guy in this book’s – basically, wanking in front of the mirror in a bra and a pair of knickers. But unlike him, I never came out to my wife till long after our marriage was over, so I was never forcibly waxed by her, then transformed into a lingerie model. And I was certainly never forced to act as a model at a lingerie party she was throwing at her friends, who would all join in to humiliate the size of my dick and even end up spanking me.

Gay sissy slut in clingy green dress

Forced Sissy Exposure

What a shame! I would have loved to experience some of the humiliation and control that Jodie gets put through at the hands of his wife during his/her night of sissy hell. He gets teased and tormented in so many ways, but he also gets the pleasure of wearing a pink babydoll nightie, a French maid uniform and then a slutty red dress that makes him look like a whore. What’s more, once dressed as a whore, he’s made to totally act like one, too, and gets fucked up the arse by one of the female guest’s husbands before being turned into a Bukkake slut.

All-in-all, SHAMED SISSY SLUT is a very well-written and evocative novella – but if you don’t like extreme hardcore action, then please be warned that it’s filled with some genuinely dirty stuff. It explores so many different kinky ideas, including forced femme, cuckoldry, chastity, bondage, discipline and public exposure; and is very obviously written by a limp-dicked sissy who has tons of experience with this kind of thing. And I bet he/she must have a really small dick, because the small dick humiliation scenes are just so spot on and definitely not to be missed.

You can order Chantelle Cage’s new hardcore novella in ebook format at A1Adultebooks.


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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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Flirting with coming out to my daughter and wanting to be exposed as a sissy to the world

Some of my girlie clothing and sexy lingerie is just too damn pretty not to be seen!

Transvestite steals daughter's dress

Sissy Exposure

I’m sure I’m not the only cross-dressing sissy who gets all dolled up in the privacy of his own home and thinks: ‘What a waste that there’s no one here to see how cute I look right now!’ I’m spending more and more time on my transformations now – doing full hair, nails and make-up almost every time – and I always wish a big strong man was there to appreciate the effort I’d made, as well as fantasising about my ex-wife seeing me fully feminised and playing with anal toys. But apart from online sissy exposure, the only time my feminine outfits ever get seen is when I drive out to toilet blocks to suck off strangers! But that takes a hell of a lot of nerve, so I only pluck up the courage every once in a while.


Sissy T-girl borrows daughter's cute prom dress

Coming out as T-girl

So, I’m mostly still pretty much stuck in the closet, although I have thought about coming out as a transvestite to my 19-year-old daughter (who stays at my place quite regularly). I’m not sure she needs to know that I often borrow her knickers (including her dirty ones) or that I’ve nicked a few of her dresses (including the purple prom dress in these pics), but I have a feeling she’d be okay with the general idea of me dressing up. And I wouldn’t be surprised if she’d be willing to help me with my nails and make-up, or even to go out clothes shopping with me. She’s a really great girl, and I almost told her the other night, but finding the words came really hard! I just couldn’t quite manage to blurt it out.

I think one thing that probably held me back was the chance that she’d be unable to keep the secret and would tell her mum. And while a part of me would love my ex-wife and her hunky new man to know I’m a cross-dressing sissy slut, another part of me is terrified about the prospect of opening up the closet door and never being able to shut it again.  But I guess that’s always the risk with coming out – once you’ve done it, there’s really no way of going back. But I know I cannot keep these sexy outfits hidden from the real world forever. And more and more, with each passing day, I have the desperate urge to be shown off as a girl.


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Cross-dressing sissy expanding his anal horizons with ever-larger dildos and vibrators‌

My dick might be tiny, but my dildos certainly aren’t!

Transvestite in black lingerie

Sissy Anal Training

I took my anal play to a whole new level last night during a three-hour session of cross-dressing, porn watching and dildo training. I put on a black lingerie set that had I originally bought for my ex wife as a birthday present. It was one of the many underwear sets that she never showed any interest in wearing for me, but at least it got some usage last night. I teamed it with some black stockings and a pair of strappy silver high heel shoes, then I took a Max Strength Golden Root hard-on pill and waited for my knickers to start to bulge. Then as soon as I was hard and horny, I put a gay porn DVD in the DVD player, then took out one of my biggest dildos and shoved it deep inside my arse.

I’ve been practicing with ever-larger dildos in the past few months; and my anus is really enjoying the ride.  If I use enough anal lube, then I can now easily handle a 9-inch length and I’m steadily getting used to bigger girths, as well, all of which adds to the sweet sensations I feel in my arsehole. I can remember how my wife always used to look at my tiny penis and try to pretend that size didn’t matter, but now that I’m the one on the receiving end, I know only too well that extra inches means extra fun. There’s just something really special about being jammed to the brim with a rock-hard phallus; and my penis always throbs when I’m working a big dildo back and forth inside my back passage.

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Transvestite Dildo Play

Of course, dildos are fantastic and help deliver some incredibly intense and creamy climaxes, but nothing can beat the real thing – and I’m getting hornier and hornier for cock all the time. I’ve made two visits to toilet blocks with lingerie on under my male clothes this week, but not had any luck in getting laid. I’ve also been out to a dogging spot; but there was nothing happening there either. But that’s the trouble with hunting for dick in public places. Sometimes you get lucky and sometimes you don’t. It won’t stop me from keeping on trying, though!

And if I go to a place and nothing happens, then I can always come back home and play by myself. And I’m getting used to lubing up my anal tract now and steering a dildo inside my ring. I’ll normally stand one upright on a chair, so I can bounce up and down to my heart’s content. I also have one with a suction cup that can be fixed to a wall, which means I can back onto it and pretend I’m being shafted from behind. It’s a Loving Joy Mr Big realistic dildo that you can purchase online from SexToysUK. I bought the 7.5-incher originally, but I’ve just placed an order for the 10-incher today. And I simply cannot wait to sit down on that!

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The sweet humiliation of meeting my ex wife’s incredibly hunky new boyfriend‌

He’s taller than me, more muscular than me – and he’s undoubtedly far better hung than me!

Cross-dresser in lingerie

Transvestite Sissy Cuckold

According to my 19-year-old, my wife has had a couple of boyfriend since leaving me. Neither of those have been serious, though, but that’s all changed in the past few weeks when it seems like she’s fallen head over heels in lust with a guy who I got to meet last week. And I can see why she fell for him!  Cos, Jesus wept! He’s 6 foot 4, with a bodybuilder’s physique and he almost broke my arm when he shook my hand. He was towering over me like some masculine god and I actually felt quite weak at the knees. We’re talking about a genuine macho stud – and he rather appealed to the simpering sissy side of me.

In fact, a part of me wanted to let him know that I was wearing knickers and stockings under my suit when we met. Or to maybe suggest he comes inside and fucks my ex wife in front of me – or even for me to dress up in my girl clothes and for my ex wife and I to share him together. I haven’t always had cuckold fantasies, but when I was going through my three years of total impotence, the thought of my wife with another man was always strangely appealing to me. And now, having discovered she was setting up home with a proper hunk of beef, I found myself getting really horny at the thought of watching her in action with her real man lover!

British tranny in white lingerie

Limp-dicked Sissy Loser

But I was in a state of shock, in some ways. Even though my daughter had already warned me about how tall, muscled and manly my ex wife’s new partner was, I wasn’t expecting such a crushing blow to what remains of my masculinity. I mean, he completely dwarfed me in every way – and I had a damn good look at the front of his jeans and could tell he would have dwarfed me in the bedroom, too. Not that that’s particularly difficult, of course! Even with the help of a hard-on pill, I’m lucky to push beyond four-inches in length. But this guy – I’m guessing eight or nine at full-length. And I bet he doesn’t need impotence cures to be able to get a hard-on each night like I do.

No, the whole thing was really rather humiliating when you think about it. They’d only come to pick up my daughter, but I invited them in for a coffee and had to watch them hold hands, put their arms round each other – and just generally behaving like two teenage lovers. And there was pathetic, little me, wearing women’s lingerie under my male clothes and not really knowing quite what to say. And worst of all, was knowing that as soon as they left, I’d be swallowing a Max Strength Golden Root sex pill and jerking off while imaging the two of them having sex together. So, it’s no wonder my ex wife left me, really. Because a woman needs a real man – not a limp-dicked sissy like me.

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A shopping spree for poppers, pills and other things that turn me on‌

You just can’t beat browsing the magazines and DVDs in a good, old-fashioned sex shop.

Impotent cross-dressing sissy

Shopping for Sex Supplements

I still do nearly all my shopping offline and have a particular fondness for the look and feel of a proper British sex shop. We used to have a couple here in Ipswich, but now we just have a really good branch of Pulse & Cocktails, but it’s not much of a drive to get to Secrets in Bury St Edmunds or the Private Shops in Southend, Peterborough or Cambridge. I could spend hours in these places checking out the top shelf magazines and fetish mags or choosing some hardcore DVDs to watch. I also stock up on sex pills when I’m there and room aromas like Liquid Gold. And I occasionally buy myself a sex toy, too, because I like to be able to see how big the length and girth of a dildo is before I take it home, lube it up and shove it up my arse.

I have mates – grown men – who tell me they’re terrified about going into sex shops, but I’ve never once felt nervous in any of these places. The staff are always really friendly and they couldn’t give a shit what stock you buy. I’ve gone into the Cambridge Private Shop a lot in the past few months and bought MILF DVDs, lesbian DVDs, plus a couple of gay mags and some tranny magazines, as well as a big black dildo and a realistic white rubber cock. And the staff don’t think it’s weird at all that I’m trying all these different fetishes. They’re just totally matter-of-fact about it.

Divorced man explores cross-dressing

Wigs for Cross-dressing

The other thing I love about shopping in sex shops is that you get to buy real products like DVDs and print mags. Because I still prefer to look at porn the old ways – and I love the feel of a mag in my hands or the excitement of popping a DVD into the player and pressing ‘Play’. I also currently have this recurring fantasy about reading a dirty magazine with another man. I’d have popped a sex pill well-in-advance, and as we turned the pages together, our dicks would get all big and stiff. And so we’d pleasure each other manually while enjoying the pictures of the naked girlies on the pages. Then we’d spill our loads all over the mag and make the pages stick together with our spunk.

So most of my sex life is offline based, although I’m not a total luddite. The one thing I’ve found to be lacking in most sex shops is good stuff for cross-dressers, so I bought my fake tits and new wig online from Nice’n’Naughty and I buy lots of my lingerie from Sex Toys UK. Oh, and did you spot the new wig in the pictures? I’m experimenting a bit more with cross-dressing at the moment and have now worn a wig and some lipstick for the first time. And who knows where that might lead?

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