The recovering crossdresser?

To crossdress or not crossdress – that is the question…

Clearing the decks — January 18, 2019

Clearing the decks

It started with what was deemed the most explicit material – videos on an explicit XXX website.  I signed in, I deleted the videos, I deleted the profile and in feeding back for the reasons, merely said that it was ‘time to go’ but ‘thanks’.

Next, Skype. Logging in soon revealed that the program had changed.  It seemed that, by default, a user was automatically hidden until choosing to make themselves visible.  I reasoned that this was useful under the circumstances and, having taken a quick look at the missed messages from a wide range of anonymous folk from the opportunistic to the friendly, I stopped only to take momentary objection to the fact that I might be unfairly ignoring those with whom I had valued apparently genuine, time, interest and friendship.

My focus though was on a thread where I had shared more video.  The hatchet was wielded, the videos were removed, and I very quickly logged out.  That seemed enough for that particular day and I busied myself with something else.

The next day, I ventured on to my favoured web cam site, logged in, took an almost reflective spin through a few uploaded images I’d spun through and had seen many times before before switching off every single element of the profile bar the account itself.  Off went former captured images, off went the gallery, off went the ‘about me’ profile, off went the questionnaire, off went the link to Fiona’s Twitter account, and having wielded the hatchet there, all that was left was the avatar and basic details.

That was enough – I took a quick browse through the latest timeline posts doing my utmost to avoid being overtly drawn in any way, shape or form, and almost celebrated the fact that the entries from those being followed were, at the time, very heterosexual rather than being more bisexual or overtly crossdressing related.

I had spent only brief moments in recent days wondering quite whether the DM box would be full of inquisitive ‘where have you been?’ or ‘where are you?‘ messages from my chastity keyholder, or anyone else for that matter, me not having left any tweets, or made any DMs, or having even accessed the social media site for fear of being drawn like a moth to a flame.

How vain was I?  What did I REALLY expect?   There was nothing but a few notifications about new followers or ‘likes’ to previous posts.   Somehow, I’d expected something from my symbolic keyholder, but there had been nothing.  Nothing.  Nothing despite having lavished hard earned cash on all manner of things for them, having lavished vast amounts of my valuable spare time, home and away, on communicating via direct messaging.  See?  I was as unimportant to them as I had perhaps always been – I’d allowed myself to be used perhaps.  After all, I had usually opened dialogue, 99.9% of the time anyway and if there was nothing to respond to, why on earth would they want to open any dialogue with me – especially given that I’d apparently vanished?

There had been warnings of my disappearance and silence anyway.  I’d previously but recently said in no uncertain terms that the turn of the New Year had caused a monumental wobble and a serious bout of questioning one’s self.     Having taken momentary objection to no one giving a damn on my self imposed almost full Twitter abandonment, I brushed any disappointment away by simply logging out.

There have been occasions when my browser of choice allowed me to see my DMs, yet this was another occasion when the virus software, no doubt having done another of its off peak updates, seemed to decide that it would not show me the various DM threads this time around.

This prevented me from going through them and deleting what is probably a vast amount of imagery of me, dressed and undressed.  I supposed that it was therefore a deck to be cleared another day and moved on.

Earlier in a week wracked by the return of the ill health that plagued me in the run up to and over the festive season, I surfaced one morning, stripped out of the pyjamas to my birthday suit, prepared the dildo and took some naked anal, the suction cup dildo against a wardrobe mirror and with the smart phone filming away, the file only staying until the clear up afterwards when it was swiftly deleted.

Overall, and certainly in retrospect, the whole thing wasn’t great for all the usual reasons associated with such sexual activity, apart from the fact that, at some points during, it was.  Having seen a Twitter post about which muscles to use to grip, I revelled in the feelings caused by that sexual exploration and feeling that it was pushing the right buttons further than they had been pushed before, pressed the proverbial fast forward button and brought myself to climax whilst still feeling full penetration and applying what seemed a rather uncomfortable withdrawal.   For the first time ever, I was not crossdressed whilst I enjoyed this period of sex, and during the experience, spoke out to myself that, despite everything going off right now, it appeared that I STILL loved a bit of anal.

Since then, I’ve not craved it again.  Far from it.  In fact, as indicated in a previous blog entry, I have since given more, brief thought to finding a box large enough for everything bar perhaps the cock pump and Fleshlight to be put into a box and remotely stored away.

Conversely, there have been times when my mind’s eye has projected images of stockings and suspenders, reminders of the feelings and look of wearing a bra, the feelings of pulling on those stockings and admiring the stocking tops.   Perusing the many blog entries and Twitter accounts that I follow, I have been confronted by images of women wearing lingerie, bras, stockings and suspenders but there has only been the briefest of sparks of interest of taking things further.

Nothing has sparked a desire to dress, although there have been moments when I asked myself whether it was worth dressing before deciding firmly against having come up with less than NO reasons to do so.  I have also asked myself whether it was worth putting on a chastity device, but after the two months or so of exploration and indulgence, other than concluding that it prevented guilt as it also prevented or at least discouraged orgasm, I have been left questioning exactly how and why I was wearing it, other than for some sort of evidently unexplainable sexual kick.

The man bag has been carried around for days with two chastity devices packed away within (read ‘hidden away’ if you like’) and the remaining elements of my own lingerie, the suspender belt and stockings, taking up valuable space with no intent of being worn yet best left there in the absence of any secure plans to be put elsewhere.

Ill health means that elements of medication carried with me are more yearned for items, but I have needed to snap myself to my senses in the midst of feeling distinctly off colour and reaching almost desperately for it, by reminding myself to avoid leaving the man bag with the top open, and, in my mind at least, open to the casual investigation of others for things to be discovered that I don’t want to be discovered.

One day this week, sitting at my desk at the day job, I decided to pick up my bunch of keys, locate the two chastity keys retained in my possession, that had previously put me into and taken me out of my partial lock up, and merely removed them before casting them into the bags in which the chastity devices resided, in the dark depths of the man bag – this was another step towards an evident and all encompassing desire and drive to clear the decks.

Crossdressing hasn’t been on my mind.  Sexual activity hasn’t been on my mind.  Prioritising more deck clearing hasn’t been on my mind really either.  Other things, other people, the day job and, unfortunately, right now, ill health have been somehow refreshingly at times, keeping the mindset more focused away from the former.  Ill health has been at the forefront of my thoughts – and when we are ill, we can rarely concentrate on anything else anyway, as we fight our way through it all for however long it takes – these days – too long.

The sex toys remain in their various stored locations, the box of lingerie and the breast forms is hidden where it has been for sometime, and the man bag continues to have my chastity devices and lingerie remnants as necessary squatters for the time being until I decide upon and/or fashion something else.

Having recently benefitted from a partial body wax, I’m not in bad shape, yet occasional observations acknowledge or even expect that it is all coming back through again and right now, I’ve almost given in, conceded defeat to body hair even though I will continue to have it removed as I have been doing so for years as I don’t want it.   My dysphoria continually sees me finger tip search for and pluck in certain areas of my body recently waxed whilst critically analysing the areas next up for waxing, hatred pouring over every glance and stare.

I have carried out the day job without worrying as to whether my lingerie was properly covered up, whether anyone suspected that day, whether anyone was talking in corners, paranoia a-plenty perhaps, now no longer an issue.   No more was I checking and double checking browsers, whether everything really, really, REALLY had been put away properly at home, or whether I’d left tell-tale signs to finally burn all bridges.   This peace of mind was somehow massively comforting and reassuring right now.

All good?  Right and proper?  Something to take comfort from?  Not really.   Relapse and resumption are still very real possibilities.  I know that – you know that.  It has happened before after all.   I could quite suddenly and easily snap out of the current mindset tomorrow, the next day, next week or even next month.

However long it lasts, whether it is for good, for a medium to long term or otherwise – for now, the decks continue to be cleared.   Make of that what you will – because I can’t.

The pendulum swings, the pendulum stops — January 12, 2019

The pendulum swings, the pendulum stops

One of my previous entries at this time of year has been ‘Crappy New Year‘ – an indication perhaps of the effects that a change of year has on quite a lot of us I would guess.

There has been a distinct change to my approach to crossdressing as 2018 drew to a close.  I recall a previous remark along the lines that I was almost reluctant to get into the lingerie yet still did.

The end of 2018 saw a clear ‘ramping up’ of sexual exploration, of bi-curious tendencies, of explicit converation via social media messaging, of posting of explicit photographs and videos but conversely, an acknowledgement that perhaps the track I was on really wasn’t the right one, both clear display and recognition of deceitful traits, more blatant than ever before, in the company of those closest to me.

Last week, the pendulum of moods was swinging.  One way, indulging as per usual, the other, the complete opposite, no intent whatsoever to indulge in any way, shape or form.

Bizarrely, there was one day when I didn’t dress nor wear a chastity device, yet the items were available to me in the man bag as I went about the business of the day job.  The day wore on as I began remonstrating with myself that, somehow, I should be locked up.

Why?  Goodness only knows, but the mood continued, and eventually, I nipped off to the gents and locked myself up in the holy trainer before returning to my desk and seeing the afternoon out in a slightly more contented mood.

Anyway, back to last week.  The night before, I had immersed myself so deeply in my apparent sexual persuasions that I hatched a plan to indulge in dressing in a black lingerie set and of using a dildo against a mirror, all whilst locked up in the holy trainer chastity device.

The plan was duly hatched the following day, despite there being no time, despite there being a need to get off to work, despite a need to have breakfast and make some lunch before I went, despite the need to catch a train etc.

Filming it all, didn’t really go to plan, yet the footage remained on my smart phone device for the time being.  Inside, I craved a sexual peak, arguing with myself that it probably wasn’t the best thing I could do, given how I tend to feel afterwards, yet I pushed on.

Sure enough, with no further urges to anything else in the immediate aftermath, the lingerie and chastity device was removed, the detritus of condom wrappers, boxes, sex toys and other items of relevance were cleared away as applicable and that was it.

Since then, there has been a sort of brightness in my stride, I have seemed somehow more relaxed, more at ease, more likely to apply myself to something else and in all honesty, I have done.

I haven’t even been on Fiona’s social media presences, most notably – Twitter.  Sure, this is abandoning the ongoing DMs with my chastity keyholder and others than I pledged to offer support and friendship to, and is in the wake of somewhat irrationally signing up to a chastity website which seems to have little substance or membership.

The mindset has turned to opportunities that might present themselves to bundle all of the crossdressing paraphernalia, toys and outfits together and return them to the aforementioned ‘remote’ storage location.

I am, of course, mindful that this could be a mere blip and something might trigger a fall back in to the embracing arms of crossdressing, much as happened all too frequently before.  Just this morning, whilst dressing, I admired the smoothness of my recently waxed chest and my fairly hair-free body, just as I like it, and for a moment or so, pondered as to whether being this way just for comfort was enough for my inner psyche.

I didn’t really get an answer together, instead, throwing myself into applying deodorant, creams and potions as applicable, then daytime clothes, then applying myself into the activities of another all too likely quickly disappearing weekend, no lingerie, no chastity, no intention.

What is it that has led to what I have often described on social media as a ‘mindf**k’?  Plain and simply, a change of year – no more, no less.  There have been instances this week when I concluded to myself that the earlier indecision had been a temporary blip and that I was back on track with my crossdressing.

However, the unavoidable guilt felt after orgasm post-anal has been a bitter pill to swallow yet again.  I have blogged before about keeping a lid on reaching such peaks during indulgences, hence the self-imposed partial chastity, but being brought to one’s senses as part of a come-down from reaching ever heightening sexual peaks and overtones, is beginning to resonate a lot more than it did before.

When I stopped crossdressing last time, one of the driving forces was that I didn’t want to perceive myself as becoming a ‘dirty, sad old man’ and this very thought has been in my head again in the last few days.  I’m pushing 50 for goodness’ sake.

I have some good things going on in my life and I have also set myself some new year resolutions, some already in draft form before the turn of the year, and now being put into place.

My inbox has given me indications of things that I need to be doing now, soon or later this year, and there are other things in my mind to apply similarly.  None, or little of those things will be done, if I cannot shake myself off what is a rather intense, all controlling addiction.

It’s probably relevant to place another of those lines in here that many have said, many times historically since goodness only knows when I started this thing.  “If it’s not hurting anyone….”.

What if it is hurting me somehow?  It must be hurting others too indirectly.  If this thing is on my mind as much as it is – there is no ‘if’ about it really – then surely anyone holding something in without being able to adequately talk about it to anyone to any significant and/or helpful lengths, must find that their mood and behaviour impacts on others, or that my actions impact on other things that one day might blow up in my face.

I’m going to have to see how long this cessation and mindset lasts.   For now, the clock has stopped.  The pendulum has swung, but for now at least, it swings no more.

Fantasy figure — January 1, 2019

Fantasy figure

I was in a prolonged, smart phone battery sapping exchange of direct messages with my keyholder when the conversation took a turn in an all new direction.

They had an ‘abdi’ fantasy.

Now, I like to think of myself as at least partially knowledgeable on any number of subjects, a willingness to read and learn about all manner of things has led, on occasion, historically at least, to my other half asking how I know such things.  My answer is simple – that I have just read something along the way and committed it to file somewhere in the darkest recessess of the old grey matter.

But this whole ‘abdi’ thing was a new one on me and I couldn’t help but continue the direct messaging exchanges by batting it back.  “A ‘what’?” I asked.  In reply, I was asked to ‘google’ it and, impulsive as I am, had to do so immediately, despite sitting at my desk at work.

‘Abdi is a sexy and hot person, he is also a lovely friend, he is there when you are upset and is really funny.  Once you get hold of a abdi, never let go of him because you will never find another one.’

‘Meaning a perfect being with no flaws, could do whatever he wants. The worlds fate is in his hands, but he refuses to help.  He is worshiped as a god in some arab religions.’

‘Abdi is a loving, caring person he knows what to do when to do it… When you get a hold of abdi never let go because there’s no one like him.  He’s always saving people never looking back.  He’s destined for greatness keep an eye out.’
(Source: Urban Dictionary)

Of course, there may be many more descriptions and even some of the above quotes have been trimmed to edit out unrelatable elements.

My keyholder went further.  They dreamt about me day and night.  I had become their fantasy figure, this because, although they may yearn and want me for themselves, they had reasoned and accepted that they cannot, for a multitude of reasons, have me for themselves.

I have already said in a recent blog entry and indeed to them directly via messaging on more than one occasion, that I do not seek to string them along, give them false impressions, and most importantly of all, hurt them in any way, but I suppose that my own vivid imagination, allowed to be poured out via direct messaging, may well do that.

Although they have sent me direct message images of their own, the inner slut that is Fiona far outnumbers them with the sheer extent, variety and nature of images sent the other way, even as far as exclusively sharing an explicit video via Skype – none of these images have ever been taken down so, I suppose, act as a gallery on which a fantasy can be based.

I have graciously, humbly but reluctantly accepted the ‘abdi’ title yet have related to some elements of its apparent on-line descriptors, those of being someone there to talk to when upset, and yes, I do seem able to make people laugh from time to time too it seems.

Sexy and hot?  Certainly not.  IWell, I don’t think I am but there lies the epitome of the phrase “Beauty is in the eye of the beholder”.  Though of slim build, the protruding belly caused by a mild hernia has caused me to hold it in on an all too many number of occasions when displaying my sexuality.   Without flaws?  Again, certainly not.  Loving and caring? I like to think so.  Saving people and never looking back?  Destined for greatness?  Perhaps I do plough on getting things done, but destined for greatness?   Not me, not I.  I’m just quietly trying to blend in.

Then there is that bloody hair growth.  I will confess to having a deeply rooted dysphoria about my body, especially in the period immediately before another appointment for some sort of partial removal by body waxing.

I am usually left immensely frustrated that some of it, not enough of it, is ready to be removed, even though I know that there is a good reason for that, that it is a race, not a sprint, that my body is being conditioned to rid itself of its hair, that the growth patterns differ right across the body, that it is dying off in some parts, thinning out in others, but I still hate it with a passion.

To me, it looks horrible and the periods where I am largely hair free are not long enough by any shadow of the imagination.   It was the way I was made, contrary though it is to my inner sexual tendencies.   To my keyholder, the holder of the ‘abdi’ fantasy about me, I am ‘gorgeous’.

I blush.  I am flattered, but know only too well that, whilst flavour of the month today, I could be cast aside the next minute, let alone tomorrow.

I know that whilst I continue to arguably shower them with underwear and chastity devices, my generosity reflecting an apparent ‘abdi’ status, and my repeated sharing of explicit photos via direct messaging, any cessation of any definitive kind may well render that fantasy over.

I was ‘married‘ then apparently ‘divorced‘ after all as my blog entries fully detail, yet the many and varied direct messages via social media have included those where the subject of that conjoining was broached.  The carriage of contact and social media exchanges, the provision of underwear and a chastity device and of explicit conversation have served to somehow reaffirm that electronic union.

Damn you New Year.  The feelings that a New Year brings have only served to send me into a no man’s land of a mindset – where the only thing I can do is write a blog entry.

The thought of doing anything else, dressing, putting myself into chastity, indulging and immersing oneself as Fiona, even logging into her social media presences and a likely direct message or two, is right now, akin to being on a diet – wanting all manner of goodies, yet telling oneself that you shouldn’t.

That doesn’t seem fair on anyone, but then seems fair on everyone.  My head is, once more, all over the place and I am seeking a multitude of distractions to numb the pain.

Happy New Year?  It’s only the 1st but dread is already here.

Resolution? — December 29, 2018


Christmas.  A time for families, persons closest to you spending time together, eating lots, exchanging presents, going overdrawn at the bank etc.

I’ve spent a few nights away over the last month or so, shopping and enjoying some family QT, only my on-line relationship with my keyholder has led me to at least partially regrettably use some of that time to chat via direct message, share photographs of me in a state of undress in the hotel bathroom, showering and becoming sexually excited for them.

It’s wrong isn’t it?  Yet I’ve done it – twice and recently too.  I’ll be honest.  Although my relationship with my wife is fine (well take my deceit away and it is), there are issues on the periphery of the family in virtually all corners, and though I know that it is wrong, I see my indulgences in crossdressing, anal play and chastity as some sort of much needed escapism from all of that almost constant misery and stress.

Another weekend away with the wife was yet again tainted by the effects of family problems, and somehow, I sought some sort of escape and solace in those private periods of direct messaging and photo exchange.  I’ve become more daring of late with how and when I make those DM exchanges, even doing so whilst the wife is in the room, in close proximity and even laying on me below camera shot as I took a pic of me in a towelling dressing gown but otherwise naked before quietly DMing it away.

I am impulsive.  Of that I know.  Whilst DMing my keyholder, they said that they would quite like to see me in a holy trainer chastity device.   A lack of viable finance mattered little. Within a matter of minutes, I’d rediscovered a site I’d once browsed for a suitable but reasonably priced trainer and *ping*, the order was put in and the item was in fact at home before I had returned from my weekend away – the arrival of the item at my home address shrouded by the conceivability that it was yet another mail ordered Christmas present.   Well it was – sort of – but for me.

Ill health always has an effect on my mindset and approach to all things that I indulge in and the virus has led to me begin using back up medication to avoid it really taking a toll.   Christmas coupled with ill health really did remove all opportunities and urges to get dressed.

Having considered what I’ve just written, that was actually a lie.  Christmas Eve when the wife was at work, I dressed and put on holy trainer (Why are they called that?  I can’t find anything that explains it but I’m not giving up on my hunt for information).   I had to be out early and went on that errand in the lingerie and wearing the trainer.

I returned home and craved anal penetration.  I utilised an opportunity in the bathroom to secrete the 6” dildo in with me, and finding any flat surface to attach the suction cup to, duly and lustfully drove myself onto it or it into me in a number of positions.

Orgasm, something I’ve rarely experienced of late in any way,shape or form all things considered, was something I just had to have.  The inner slut determined that at the peak moment, the trainer sheath having been removed, I would bring myself to climax into the toilet bowl but with the camera phone running, the footage albeit later deleted and going unpublished.

The peak achieved, the clothing was put back on, everything was cleaned up, the dildo put back into the box and secreted out to its usual storage point in the man cave, although the dildo had not helped me reached my peak, as has been the case before, my bi-curious training continuing.

In the bedroom, I removed my outer clothing, removed the lingerie, removed the trainer and slipped back into what I frequently call ‘civvies’, content with having satisfied my urges for the time being.

Ill health had been conquered by sexual energy and adrenalin but the following few days were racked with more ill health as the tablets continued to be swallowed.  At the same time, the urges towards any future dressing and in fact, even accessing Fiona’s social media presences seemed way off the table.  I told myself that I would not log in as if setting an early new year resolution was the only way forward.

“Sod that!” said a voice within.  Day 1 back at work after the Christmas break and that urge to remain in civvies motivated by ill health above everything else seemed right and exact – the right way forward, but by Day 2, today, I put myself into the trainer as soon as possible, covered up with one of my favourite outfits, and prepared some lunch and breakfast in the kitchen downstairs, blinds down, or windows distant.

Inside, the urge to feel the penetration of my dildo began to surge around my mind.  I analysed the available time and managed to avoid giving in to temptation, instead remaining in the trainer, the daytime lingerie, recently laundered one early morning whilst home alone whilst doing other items, was put on.

This was the first prolonged period in the trainer, and at work in it too.  Bizarrely, retrospectively, at least, the lingerie I was wearing, felt normal – as if I was always wearing such items.  The focus was definitely on the trainer.

Over the course of the day, I exchanged so many DMs with my keyholder that my smartphone battery went critical, the tone of conversation ranging from explicit, lustful and fantasy to general conversation as my cock stirred as far as it could within the confines of the practically all encasing holy trainer.   Time elapsed.  The day wore on and when the work day had finished, off came the trainer, off came the lingerie and in it all went into the man bag.

The man bag is now practically bulging with crossdressing paraphernalia and to this, I must remain vigilant.   The cage is contained within a cloth bag, the holy trainer in its see-through brown zip case, a black cloth bag regularly housing my lingerie and from a point when I had enjoyed a day of anal stimulation, a now nigh on fully empty bottle of lube.

All of this is so wrong.  Yet all of this is so right.  To the average person who knows me, there is nothing unusual going off – everything happens sub-surface, intimately, personally, privately, constantly running risks, constantly shrouded in a need to vigilant, careful, checking, double checking, triple checking that everything is back where it is.

That hasn’t stopped me irrationally wondering what has gone wrong on the occasions where the other half doesn’t answer her phone to me, only for there to be a completely innocent reason, my meticulous attention of detail in covering my closeted tracts continuing to hold me in good stead, complacency to be avoided at all costs.

I’m a crossdresser.  I succumbed to it again in June 2018, but I have also succumbed to the on-line relationship with someone I’ve never met.  We know so much about each other, yet so little – they want me, yet can’t have me.  I see a parallel universe where I am with them and I move from bicuriousness to being fully bisexual, dressed, caged, released, taken, owned.

I have regularly signalled that I do not seek to string this person along, reiterating that they know how I am fixed this end, despite the explicit nature of conversations, the fantasies, the nature of discussions, the fact that I am, to all intents and purposes, owned, sexually to an extent at least by them.

I told myself that I would not open dialogue through social media again, but then I did and immersed myself fully in it once more and some.  It is needed – it is necessary, I can’t stop, and right now, I won’t stop.  This sexual journey absolutely HAS to continue.

..and now, given the restrictions between me and my keyholder, I have become a fantasy figure…that is for next time.

Resumption — December 28, 2018


It was always going to happen.  I was always going to let it happen at some point, especially given the heady empowering temptation and experimentation of chastity, and also given the fact that I was home alone for the weekend.

On arriving at home at the end of a busy week of whatever the word is of not doing something, the blog was updated with a previously penned two entries, but chastity brought on a third entry in one day.  In self-imposed chastity, the urge came to be dressed and as the evening wore on, only a couple more hours were allowed to pass before the lingerie came back on again.

And it stayed on all weekend.  The first night saw a state of almost constant arousal, the erogenous zones being teased as the pressure forced flesh against metal repeatedly as chastity struck at full pelt.

The night-time hours were met with little sleep, dressed for bed in a lingerie outfit of choice, the state of arousal continuing, waking me from the sleep I did manage to have.   As the correct fitting of the cage had yet to be learned, there was a need to unlock, and recage from time to time, me wondering whether I had in fact ordered the right size after all.

I vowed to try a smaller size in the event I decided to order a second such item but for now, it was about getting used to this one.  With a necessity to be up very early in the morning to run an errand, I was awake before the alarm anyway as sexual energy continued to pour through my body, struggling to deal with this new voyage of sexual discovery, all that it offered and the feelings it created.

The energy used in merely getting me through the Saturday, coupled with the constant state of arousal to some extent, coupled with the necessary early start left me shattered by lunchtime, a need to sleep, but an urge not to and make best use of the day instead.

And so it went on.  I threw myself into watching some mundane television in the hope that it would take my mind of experiencing chastity for the first time, and it did indeed work to a degree.  But when it drew as close as possible to a semi-normal bedtime, I used the opportunity to turn in for the night, albeit changing from a bra, high waist suspender belt and see through g-string to a favourite red and black cami-suspender outfit to wear to bed and as it turned out, throughout the following day.

Still the eroticism and state of arousal powered on as I busied myself by day, attending to voluntary work remaining underdressed and caged, continuing to share the experiences on line.

Days later, two of the three keys that came with the cage were packaged up and sent to my keyholder, if nothing else, a symbolic acceptance of being in albeit partial chastity.

The beginning of that partial chastity now spans back more weeks than I can remember but numbering at least four.  Over most days of late, I have spent almost twelve hours a day in chastity and many of those hours in some sort of state of being underdressed in lingerie whilst at home alone or at work.

So with that period of chastity having elapsed, I have taken it upon myself to notify my keyholder when I am both caged again and released for the day with the sole key that I retain.  They never asked for such notification, nor have they chased on the rare occasion when I have not notified them – I have merely been praised when I have done so.  My life, lifestyle and commitments outside of my closeted activities do not allow for total ownership or indulgence in any other way, so the arrangement is a good fit as is the cage, which has since been supplemented by pink ribbon binding, recommended after a request was made by social media, the trial flat shoelaces consigned to the history books.

I have orgasmed only a handful (!) of times since putting myself into chastity.  A week into it, one morning, I reached a peak of needing to achieve what would be a ruined orgasm apparently.   I tried anal play but experimentation has only carried me close but not fully to orgasm.   One morning, I managed to establish a Skype session with my keyholder which had reached the point of failure anally.   However, within minutes, I had realised that the very small margin of space between the minimum and maximum extremes of the lock mechanism allowed enough room and jiggle space to somehow reach climax.

I re-established the Skype session and, asking what my keyholder had evidently done to me in my fit of sexual euphoria, without seeking an answer, eventually felt a huge urge as two rapid watery bursts of semen powered out like a hose reel jet, splattering in all directions – I’d never experienced anything like it sexually and I was somewhat taken aback.

A few days later, a further caged orgasm was achieved, but this time, with the semen more akin to a regular consistency, the inner psyche having come to terms with chastity and having overcome the first release and the period immediately after going into chastity.

Anal playtime has increased in regularity of late including on the first weekend of chastity, where such playtime just had to be experienced, the dildo being ridden and used in a variety of positions as exploration of one’s bi-sexual side was allowed to take precedence, going so far as posting a video of a 10 minute part of a total 45 minute bedroom session on a X-rated video website, my first ever posting of its type.

Weeks have drawn on, direct messages including explicit photos have been shared with my keyholder and posted on my social media presences, Skype and webcam site chats enquire about who it is that has caged me, request that I am released etc. but without success as I remain loyal to my albeit symbolic keyholder who I have confessed to, who asks who it is that makes these requests, but quickly accepts my honesty to them and refusal to others.  Some viewers relish in the fact that I am caged and it keeps them online whilst for others, it is clearly not their thing to see my restricted, particularly for those that have been used to seeing me free, released and at play over the years.

But here’s the thing – being in chastity avoids me falling into such low periods of guilt experienced after orgasm.  If I cannot reach orgasm because I restrict myself through chastity, I cannot feel that way in the aftermath, and am instead, arguably ready for the intimate moments that really matter.

There is a potentially dark side to chastity – prostate health.  I have been told on more than on occasion that it is good to release what is stored on a regular basis to keep the prostate healthy, so somehow, there is a part of me that seeks to achieve a balance between inner feelings, a need to avoid the overwhelming sense of guilt felt after dressing and orgasm,, prostate health and applying myself to the life everyone sees me in.

However, even though the onslaught of winter and ill health has got in the way, chastity has taken another turn within the last week…

Caged — November 23, 2018


I was home after another day at work.

I was soon in the bedroom and undressed.

The cardbox box was hacked open, the packing removed to reveal a plain white box within, only slightly branded.

The sealing sticker circles that covered openings appeared far too stubborn, but with persistence, one was eventually picked open.  Inside, the cage was well wrapped in tissue paper, tucked down the shaft.

With the cage, there was the ring.  I quickly fathomed that both the ring and the cage seemed to be the right size – for once, I’d guessed something correctly.

A small rectangular shape, again, tissue wrapped but stuck down, sat nearby – the padlock.

The fitting of the ring, cock and balls threaded through, was eventually completed – metal striking cold after the box had been stored in the car for more than a few hours.  The ring sat close to perineum beneath the balls, and just above the shaft, which seemed to have become stimulated all by itself, and there then being some trouble adjusting mindset in order to fit in, the shaft, in that state of semi-erection, eventually fitted fully in to fill the available space.

The fitting of the cage to the ring, sliding it over the protruding bar, was being hindered by swollen and in the case of the balls, retracted tissue., but with a bit of prodding and poking, one piece of metal met with the other.

A quick test of the padlock and key to assure that it was in working order was completed and the padlock was fitted and locked on, conveniently at a time when I was home alone for a time anyway.  It seemed OK to proceed.

Body warmth ultimately warmed the metal to temperature and all felt fine.  The g-string worn for the day was put back on but it struggled to accommodate everything now being asked of it and so was quickly discarded, a dressing gown thrown on instead.  As I moved around, the padlock clinked on the metal of the cage in such close proximity.

Then, came the knock at the door – a late postal delivery!

I threw on some jeans and a t-shirt, and answered, the padlock still giving what, to me, was an audible clinking on the cage, yet slightly more restricted and muted due to the close proximity of the material around it.

It wasn’t long before the delivery had been accepted, the door locked again, and, having returned back upstairs, discarded the clothing, put the dressing gown back on again and began posting two previously written entries, and then, as it was convenient, necessary and overall, desired, this, the third blog entry of the day.

I paused for a moment to check the existence of one of the padlock keys which I had threaded on to a ring on a bunch of keys to life, keys to this, that and now, very clearly, the other.  After a short while, I used the key to unlock, and then lock the cage back up again, as if some further reassurance was needed.

I am then, for the very first time, in self-inflicted chastity, albeit of my own control, for what will probably be the weekend – and that is very thought provoking indeed.  Whether there will be any lingerie and crossdressing added to this already heady mix remains to be seen.

Annulled —


It was an experience.  What it was really about and what it really meant, I don’t think I will ever know but it was undoubtedly a case of “been there, done that” wherever ‘’there” was and is.

Having sent another pair of undies off to Safia, then came the silence around the time that they should have arrived the other end.  The last DM entry was that of Safia being seen wearing a pair of the previously mailed undies described by them as “panties”, which they said felt “amazing”.

I said that they were all I had ever been wearing having ditched boxers many years ago to which it was inferred that I had only ever been wearing women’s panties.

However, I said that I hated to shatter illusions adding that they were in fact male g-strings and made to accommodate one’s bits!  This was acknowledged with a one word answer. “True”.

From then, there were no further messages, nothing to acknowledge receipt of the latest item posted, a treasured pair of tartan undies, nothing.

As predicted in a previous blog entry, it would appear that the symbolic joining of crossdressers via social media has effectively been annulled in a very short space of time.

Reasons?  Well, from past blog entries, it is likely that you can work that out for yourself.  I shall say no more as is only right and proper.

Call it paranoid, obsessional or just inquisitive, but having kept an eye on Fiona’s Twitter presence, a check today saw an evident, visible, definite parting of the ways between Safia and I after no more than a fortnight and probably not even that.  The dual name has gone from their profile, the connection to Fiona on the social media profile has gone, but perhaps more telling, is that even the sisterhood has been erased from the same profile.

Fiona’s profile was similarly and arguably fairly and justifably reversed, the pinned post announcing the e-union thrown almost by cannon fire down the post list into comparative Twitter obscurity upon being unpinned.

This left things at a bit of an impasse for the foreseeable.  Firstly, there was the small matter of the item ordered from Safia’s wish list, something which also has long since been missing from her social media profile, but had been shared with Fiona in the interim.

Now, I/Fiona (work out the definitive as you will) have been mulling over the severing of ties throughout the day as the communication line remained silent and empty from both ends.  Deciding that I have never been one to intentionally hurt or mislead anyone, I felt it only right and proper to simply log on, open up the dialogue once more and apologise, expressing as above, that it was never my intent to mislead or cause upset.

A brief answer came back appearing to accept the apology – it was “no problem”.    Perhaps unsurprisingly, my reply was longer, as ever, more rambling, advising that if Safia would rather not receive the wish list item, I’d be happy to go on and try and cancel it.  Again came the short reply that it had just been received, as later confirmed by on-line notification.

I recalled how the three piece was not complete with stockings and felt that it was the least that I could do to offer to arrange for stockings of preference to be sent on.   That is where the conversation has, to date, stalled and probably for very good reason – we don’t live every second of our lives on line after all.

I’ve read between the lines.  I can see what has gone off here and I’m not about to document that on line now that things have changed in the way that they have, despite earlier permission for full disclosure of things as they were.

Back to me then and there was still the small matter of the chastity cage now in my possession that remained secreted in a box in a box.  This, I figured, would go one of three possible ways.

1) That I’ll open it, it will fit and I will keep it.
2) That I’ll open it, that it won’t be the right size and I’ll have to return it somehow.
3) It will end up as a £50 piece of scrap metal to become the first thing I’ve purged for a long time.

There was a part of my mind that sought to use it for some sort of further sexual exploration.   There was another part that wanted to claw back the investment, money being short as it is, somehow remonstrating with myself as to why I allowed myself to invest in this item when there was actually little apparent sense all along.

Instead, a few days ago, I allowed myself to be carried along on a wave of sexual euphoria – obsessive, compulsive, determined, driven.

The cynic within focussed on a default position, that being option 2.   Somehow an element of denial stopped me from ordering a small cage those short few days ago when in actual fact, that really is as good as Mother Nature permitted, instead opting for ‘standard’ whatever that means.

I have frequently joked, or done myself down on line by using the line “big things come in small packages”.  Again, you make up your own double entendres!

The obsessive compulsive side of me focussed on getting home from the day job and finding the moment to take it to the next level or perhaps the relationship with the cage was be something else soon to be annulled…