Saturday 28 July 2007

Lesson 10: Lingerie Humiliation - Part 3

Here is the final post for my training.

Having returned home and changed into my outfit for the evening (see previous Lesson 10 posts). I got ready for the more enjoyable parts of the evening.

One thing I have learnt from this lesson is that PVC gets extremely hot and sweaty very quickly!
Having spent time in my new outfit - I couldn't stop feeling the fishnet hold ups which made me feel particularly slutty and drove me to distraction, I felt ready to complete the last part of Lesson 10.

Positioning myself in front of the mirror I watched myself sucking happily on my pink jelly dildo, again pushing the limits of my throat as I tried to imagine taking your lovely strap on cock without complaint and without flinching. I thought about all of the lessons that as a sissy slut I had completed. More importantly I thought about which bits I could have done better in terms of improving it for Akasha. I also thought about the question that had been posed - what have I become.

In the mirror I saw quite an embarrassing site of me squeezed into a big white lacy bra and wearing a PVC policewoman's outfit. This was whilst sliding a pink dildo as far down my throat as possible, trying not to smudge my lipstick and sporting a bulging sissy clittie in a permanent state of leakage over some white lacy french panties. Oddly this was a proud moment as I had to admit to myself that my actions over the course of the lessons had made me a lesser man...but better sissy slut. This was incredibly erotic and humiliating to me knowing that I had willingly transformed as the request of a series of lessons, posts and responses.
Fantasies of cock sucking and being humiliated have been creeping into my daydreams and thoughts, also the thought of what limits that I could be pushed to make me a little apprehensive, turned on and extremely curious. Just how far would I go?

Switching the Dildo, after lubing up, to work on my ass made me feel fully stretched and vulnerable again and I wanted to keep the dildo in as I swung my legs over my head ready for my final climax of the training, as this felt fitting based on all of you encouragement and pictures that you have painted in my mind. Again I was leaking precum profusely and just about ready to burst with excitement. I spent a lot of the early evening licking the precum off my fingers.

My cum facial definitely felt like a reward after the preparation of the shopping trip, the outfit and the cocksucking.
Predictably it was less than 90 seconds before I came all over my face and mouth - not a drop split on either the new outfit, lingerie or bedclothes.
I also came with a big smile on my face that I had made it all the way through - a little late - but all the way through nonetheless. I scooped my mess from my face and drank down the cum in my mouth before sucking my fingers clean and generally tidying myself up.

I fell back onto my bed with a mixture of relief, mental exhaustion, and a slight tinge of sadness that the training was over. Not with a sense of revulsion that I had got cum over my face seconds earlier which is how I would have felt at the beginning of the training...perhaps this is a measure of how far I have come....and certainly not forgetting the main driver which was to try and make Akasha smile at the very least, and turned on at best.

I am writing this up the day after and realised that I could have gone to the toilet standing up or worn male underwear but strangely these habits have not stopped, and I am sitting here (rather poetically , but not planned) in the same pink underwear that I was wearing for lesson 1.

I have learnt lots about me, hopefully I have entertained you and although I am a little disappointed that the training is over - I can't stop wondering when my next butt plugging will come.

As ever - thank you and I hope you got something out of it as well.

Friday 27 July 2007

Lesson 10: Lingerie Humiliation - Part 2

Having got home from the shopping experience I decided that I would post pictures of myself in the outfit that was chosen for me by the girls at the Lingerie store. I am sure that they enjoyed themselves more than I did!

Here is me ready for my night in with Akasha's instructions.



This has been incredibly erotic so far and I am now at bursting point. I hope that you (Akasha) enjoy the pictures.



Many thanks for this lesson so far

Lesson 10: Lingerie Humiliation - Part 1

This morning I spent my time in the shower lathering myself up with floral shower gel, tidying myself up with a razor, and then applying lavender oil to my body. This was a fairly hollow experience as my mind was on one thing really - the envelope.

Even though the lesson hinted at the potential contents I was far from happy. This really was a case of being utterly vunerable and in someone hands.
All that I could think about is that I would be wearing pink, lacy, crotchless training panties; the "Gates of Hell" and have my ass plugged and would handing over a note which could potentially say anything.
I tried to reason with all this but whichever way I looked at it I was full of fear and dread.

Before my trip to the mall I put on the Gates of Hell. With the lacy thong panties this did nothing to help hold the Gates of hell into my body so I decided to wear my jeans to help hide it. The fear was causing my sissie clittie to basically disappear and there for the last two ring ended up clinking together with each step even when I had my jeans on. This was not the best start to give me the confidence I needed.

I took my black bag with me to the mall as I decided to apply the butt plug there - as I am new to wearing one and wasn't sure how long I should leave it in.


Arriving at the mall I headed straight for the public restrooms and found myself a cubicle.
Coaxing myself out of the Gates of Hell was not too bad...and I pushed in my buttplug to fill my ass. My sissie clittie was already straining and had made a precum mess on my jeans in the journey to the mall. I rubbed myself and came to the edge in just over a minute - I didn't even get my clit fully hard. Like a good slut any precum went on my lips or was sucked off my fingers. I gave myself a few minutes, thinking only about the training and feeling the expanse in my hole before I brought myself to the edge again.
Like the slut that I am more precum followed and more licking of fingers. I managed two more cycles of stroking my clittie in the 15 minutes I had before I painfully now bent my clit in two to force it back into the Gates of Hell...and then suffered the constriction of the rings. My panties were hitched up and then My Jeans pulled tight desperately trying to hide the Gates of Hell.

I left the cubilcle with the intention of washing my hands and hading to the perfume counter...

The first three steps with the Butt Plug in probably made me look like a tottering camel (or novice in Heels). This was the first time I had ever walked with a butt plug...Oh my god!
It was like having something constantly pound my hole - It was likethere were no other feeling in my body execpt the nervers in my ass!

Leaning on the sink and not moving was a great comfort as I washed my hand and made to leave the restroom.
The butt plug completely changed my way of walking - I was instinctively clenching my butt cheeks and lifting them just to get comfortable and walk without looking too ungainly.
I soon learnt to shorten my stride and almost walk with one foot in front of the other like a catwalk model as this seemed to ease the pressure.
The short walk to the perfume counters was a blur. I didn't browse to long and chose the Estee Lauder counter where the girls we only to please to give me a squirt of perfume...I am pretty sure that it was called "Beyond Paradise" but if I am honest all I could think about was the plug in my ass and "the letter".
Having bee sprayed to increase my femininity I headed for the lingerie shop. My hear was banging and I felt physically sick.
I went in a looked around at all the bra's, basques, etc. and panicked and left the shop.

I sat down on the bench an composed myself again...and went into the shop and headed over to the counter. There were two girls behind the counter, it was a do or die moment, the older of the two asked if she could help me. I said Yes, and explained that I had been given this letter and asked to give it to them. They looked suspiscious and then said who gave you it? I simply replied "My partner - I am afraid I do not know what it says"...This reassured them and they opened up the letter. They both read the letter and started to read bits out. I turned bright red and was shaking a little. They commented how this was a great idea as there Boyfriends could never get the right things. They then talked about a costume party and asked me what sort of party. I confessed that I didn't know I was going to a party.
Then the younger one grinned and said "There for him." - I didn't know where to look or what to do, I was bright red and wanted the floor to swallow me up.
They then pointed out that the costume needed to be over the top and the bra and nightie needed to be lacy rather than functional. Hearing the letter read out in snippets while I was just standing there just made it worse.
They loved the part that I knew nothing about this and laughed when and pointed out the bit in the letter about giving me a hard time.
I think they took pitty on me because they both said "Don't worry, we will sort it out". I was then asked my chest size - which was bigger than most of the things in the shop. The older assistant said that the biggest nightie would probably be a bit of a squeeze - but that they did have some play costumes that might work. She went off to the nightie section and sent the younger assistant off to the costume section to see what could be found. The nightie that came back was an elegant red with black trim. She said that they had a great pair of black lacy knickers and stocking to go with it. Again I just flushed red..and stammered "nice". Then the assistant came back with PVC uniforms for nurse and police. My eyes nearly popped out as I would never have picked these.
"What do you think" they asked..."The nightie looks good" I suggested.
"Hmm- your partner did say that it should be over the top...I think the costume is much better, you don't want to let her down."

This was the killer comment as from this point on I knew that I would go along with whatever they said.


The attendants enthusiasm increased. "Go and get the white lacy bra and panties - they will look best under the costume showing through.
When they returned - she gave me tips on padding out the bra and then held up the knickers saying "I don't mean to be rude but these should fit you". Again - I could have died of embarrasment.
"What do you think" they both said.
"Great" I managed to mutter - I was starting to feel that the whole experience was coming to an end and my esteem was lifted slightly.
"You need hold up stockings as well"
"Do I ?" I questioned.
"It will complete the whole over the top look...she will appreciate it" - Again another killer blow and I agreed.
"Do you want us to wrap them so you can give it back to your partner as a gift?" they asked.
"It should be alright like that" I said and proceeded to pay.
"I would love to talk and meet your partner" said the older girl, "This is a great idea, I'm going to have to try this out on my other half". I simply smiled, probably for the first time in the whole experience.
Then came a sentence that I could never have prepared for...
"We do have one request. In return for helping you with the outfit we would like to see a photo of you in it."
I was completely lost for words...and must have looked like a rabbit in some headlights.
"We would like to see a photo of you dressed up in this" she repeated.
"OK" I stammered, as I took the bag and left the shop.



My exhale of relief was audible just over the threshold of the shop - the butt plug didn't bother me - and my thoughts were now to the latter part of the lesson. It is not an outfit I would have picked...but all in all my fears about the shopping were now over and I could enjoy the last part of the lesson.
A few paces into my stride back to the car I realised that I had leaked a great deal of precum during my embarrasment in the shop. What a desperate, humilated sissy slut I have become...but I was proud that I completed the shopping task without cheating and as I hope it was meant to go.
The conversation I remember vividly and have not been altered for emphasis or dramatic effect - I am sure the girls behind the counter would vouch for me.

Thank you for this part of the journey.

Lesson 9: Filling Sissy's hole

APOLOGY: First of all this Lesson and the next one are late and probably after the end of the training. After Lesson 8 I picked up a serious virus from my overseas travels which has laid me completely low for about a week. However I am determined to finish the course come what may.

It is funny but one of the greatest worries for me whilst being ill was how I was going to finish the training...and how I felt I was missing out. But I am now back in panties, with a stable digestive system, and raring to go.

Reading Akasha's words in Lesson 9 simply reinforced the idea that I am happy to be a slutty sissy bitch for her. All of her descriptions hit the spot with me - the begging to suck cock, the interaction with her girlfriends and then the acts of being stuffed at both ends just confirmed that I found this incredibly exciting, terrifying and making me want to do more.


Deep throat Cocksucking is still the thing I find most challenging even now I have replace the Cucumber for a Dildo...(there was not much choice in the shop that I chose!)





Here is my before cocksucking picture of the lipstick that I reapplied at least twice to try and do a proper job. I even wet my lips a little for the photo to try and get that glossy look!



Twenty minutes of deep throat cocksucking is tiring, mentally and physically...trying desperately not to smear the lipstick, trying to stop the gag reflex and trying not to dribble saliva too much. I think that I only made it through because of taking the tortoise approach and not the hare!
I am probably OK if I'm controlling the pace...but then again if Akasha was there that would not be the point. No doubt she would wait until I had breathed out before upping the tempo so that I struggle to not only control my reflexes but also to breathe...but then I might be being presumptuous.


Here is the After picture of my lips. I seem to have managed to get a little lipstick on the side of my face but I've no idea how!



Next came the ass fucking...this was more difficult than had I been able to complete the lesson last week having worked my hole with fingers and butt plug. I felt basically like I was starting from scratch again.
With my training panties provided by Akasha now round my ankles my elbows on the floor I came face to face with the dildo I was now lube-ing up to violate my ass with. Having my panties around my ankles somewhat "hobbling" me felt especially demeaning as I then reached my had around with the lubed-up dildo and started to work it into my hole.

That instant feeling of being filled versus trying to push back and get it out washed over me as I then with my head on the floor started to work the dildo in and out at a slow pace. The complete fullness and vulnerability of having a cock inside made me shut my eyes and forget all about my own sissy clit. Quite frankly it felt like it wasn't there as all of the sensations were now internal to my body sending confusing signals all over.
After only about 3 minutes already the precum was oozing and dripping from my sissy clit.
These sensations were repeated over the next 10 minutes as I began to alternate between fast thrusts and slow deep thrusts until I was again physically drained and glowing with sweat working so hard.

As to my most humiliating fantasy?

It would be too easy to say that Akasha hit the nail on the head with most of the descriptions laid out in Lesson 9. I absolutely get massively turned on by all of the Corporate Slut series.


For me my humiliation fantasy is pretty simple...it would be a state of mind that I would reach where I know that I had gone way beyond what I thought that I would think and "allow" as in my comfort zone and possible...and that I did this because a dominant person that I had put my trust in had simply asked me to and that my only reaction was to simply to comply, not for my own reasons but purely for the dominant.


Hmm perhaps this is a little deep - but it has translated and showed itself in many ways in this training - sending video clips, purchasing butt plug, being completely absorbed by nothing else than knowing a training kit will arrive, that sealed envelope, wearing panties each day, cumming over my own face...fantastic. I am sure I am living some of my fantasy now.


Thank you for my somewhat belated lesson.

Friday 20 July 2007

Lesson 8: Sissy Party Service

Now is not the time for excuses, but the for the las two day I have not felt better than extremely grotty...

Having caught a stomach virus for two day overseas I have been laid up in bed for two days feeling sorry for myself, rushing to the bathroom and fell just generally dirty.

Today has been the first day when I had had a chance to feel girly and sissy again.

The description and thoughts of being used at the party by your girlfriends is always instantaneous and gets my clittie hard, the pink ball gag and restricictive skirt, the tinge of humiliation in the service and the undeniable excited of being used. As usual at the moment this just sets me off again and I have been pretty much oozing and juicing my panties on an ongoing basis.

At about 10:15am, 3:11pm and 8:48pm I have managed to slip away from my previous routine and bring myslef to the edge in seconds and coat my lips with my own special "cum-gloss". I have been able to hide my lubricant in my pants pockets and have felt this almost burning a hole in my pocket as it travels with me.
The 10:15am stop was in my office toilets at work, the 3:11pm in a local mall and 8:48pm in the comfort of my own home.

There was nothing comfortable about being bent over in the bathroom with a lubed finger worked in my ass with my panties around my ankles or on the mall occasion simply slipped to the side in an effort to be discreet. It is amazing how quiet everything seems to be when you are desperate not to make a sound! By the end of today I have been fully aware that my hole does npot belong to me. There is something deliciously dirty about knowing that I may be called upon at your whim to do whatever you wish and receive anything in my ass for you.
Although I have only had a chance of fingering my hole for today I completed the cum part of the challenge today in an effort to keep up.
I am getting less and less fond of cumming each time.
The taste of the condom lubricant on my new dildo is still with me and make my stomach feel rough. but rubbbing my protected clittie and also sucking on my dildo made me excited in seconds and feeling very desperate and wanton again. Within a minute I was on the edge and squirting my juicing deep into the condom. I carefully rolled the condomw off and then sqeezed down the condom (like a tube of toothpaste) so that my juicies were collected in the tip and my large load of mess was sitting pretty in the condom.
I then put the condom in a drinking glass on the desk with the tail of the condom draped ofver the edge of the glass so that nothing would spill.
15 minutes is a very long time to be staring at my own mess knowing what I was about to do.
All I could think about was how much of a desperate slut I must be to want to do this...
The quarter of an hour was up and deciding that speed was the best policy, I tipped up the condom and draing as much of the liquid as possible into my mouth. The now familiear luke warm, nearly cold salty tase mixed with the lubricant stuck in my throat, ut went down. Then came the working into the condom with my tongue and the eventual turning inside out of my clittie sock until it was like sucking and chewing on rubber cum, licking and cleaning the inside of the condom.
This is not a pleasant experience and one that could only be worse if it was another mans condom.
All in all a horrific experience and one in which I couldn't get the condom out quick enough.

Thank you for my lesson.

Sunday 15 July 2007

Lesson 7: CBT to Delight Me!


The first thing that I can say about this lesson is that it has certainly ramped up the intensity of the training several fold on an emotional and discomfort level.

Being able to piss sitting down is quite a relief at the moment as it gives me a change to re-adjust the "gates of hell" that are now a pretty much permanent fixture on my body, and when not on have left a permanent reminder that they were there.
The sexy, sissy slut toy is bit by bit, day by day emerging as I try to push myself further because Akasha asks it of me. For me this is no easy thing to admit and is not a flippant throw away statement.

It was very strange for me this time because when first reading the lesson an seeing that we were allowed to cum, I was more focused on getting this bit out of the way and trying on the gates of hell.
Re-reading the lesson again made my clittie get hard as I prepared to try and video myself being allowed to cum. It then hit home to me what I was not only willing but desperate to do. I was setting up furniture, preparing my body with lipstick wearing the training panties and Slave tag you picked out for me and a the slut bra that bought; I was desperately trying to create a contraption to hold my video phone so that I could capture myself for Akasha. I even had a trial run of how it might look to make sure legs weren't in the way. Is this the action of a rational person? What lengths would I continue to go to? Would I ever say enough is enough? This is now an inherent small fear factor in me that I am thinking like this. (Sorry sounding a bit self indulgent).

The video that I have sent to Akasha is testament that the whole process lasted under a minute. What a sad sissy slut with no will power I have become. Watching back the video was horrific. It was made me fell seedy, cheap, humiliated, pathetic as I could see in myself that I was so determined that I wanted to put on a show to try and please Akasha. Having stopped the video, I was standing in the mirror looking at my cum covered face with my mind totally messed up, with thought ranging from "Had I done enough to please Akasha", "What the f**k do you look like", "You sad, sad man" - It was definitely a moment where I felt everything was stripped away from me...even now I am not sure why I did it and if I enjoyed it!



I think that would have been Lesson enough but the weather must really be playing having with Akasha sadistic side as now the second part of the lesson was to come into play.

Gates of Hell. Pleasant - Absolutely Not. Weird - definitely the first time it finally goes on. Distracting - At least once every five minutes. Uncomfortable - Hell, yes. Painful - yes, that too.


I am sure that Akasha takes delight in the fact then when I was reading the instructions for the Gates of Hell that she constantly mocks that fact that my sissy clit will get hard. Which then makes it pretty much impossible to get the first ring of cock and balls.
In fact getting my balls through required five minutes of thought. Thank heavens for the tucking exercises, it was much easier to pull all of the sack through and then coax each testicle out again. (Not so easy after one day of wear as I swear they have a mind of their own and know that they don't really want to be trussed up) With a hard clittie it just isn't going to happen...no amount of bending in two, which was very painful, was going to help. It took three goes to finally get my clittie in. Then it was a race against time to feed the other rings over my clittie as it hardened straight away again. Only this time it was a case of meeting an immovable ring shaped object which chaffed the head of my clittie causing biting of the lip and a brief expletive. Sadly it is not like in the cartoons where you can thread a camel through the eye of a needle. There really is no way of getting anything through. which just leaves rubbing, straining, constriction and occasional pain. It was worse after the first time as my clittie would grow into the rings rather than against and after several repetitions each day really does rub the same spots each time. Here is a picture of said Gates of Hell. The blue tinge is not a filter but merely the end of a rather tormenting session.



Don't be fooled by the pain bit though. The Gates of Hell aren't designed to sit discreetly. You can feel each ring through outer clothing, through the panites and every time that I sit down I am utterly conscious both of the rings, my constrained clittie and my need to be trained.




Equally as humiliating is that my clittie when not aroused is very small and therefore doesn't sit in the rings and therefore movement can cause the rings to audible clank together, necessitating a readjust, which just reminds me that I am constrained, which then excites me, which then sees me fill the rings again in a catch 22 thing. At works I got my clittie pinched between two rings leaving a bruise on the skin...but then it is difficult to adjust yourself in public when at a face to face business meeting. Even worse is that the rings will occasionally turn and therefore a seam of metal may then be exposed and rub against my clittie until it is very sore. At the moment I am on a very intense regime of rubbing moisturiser into all of the places that are getting rubbed. Luckily I have not had to give myself an Ass ramming yet at night as quite frankly my clittie doesn't seem to get full aroused at the moment after two days of Gates of Hell wearing.

This lesson will very much be a mind over matter thing, it isn't pleasant but the effect of wearing the Gates of Hell is well calculated with the discomfort/arousal cycle.

However its not all bad...there is the occasional feeling of pride as you tick off another hour, preferably without having constricted yourself to oblivion.


On all levels this lesson is totally messing me up - in a good/strange submissive way.


Thank you for the lesson.

Return of the Chat & Slave Kit

Blimey what a hectic few days...first of all a few of my thoughts after the chat on Thursday...

Well done for all those who lasted the distance, what a lovely bonus from Miss Blue for those of us on training...
I thought that the chat pre-dungeon was very enlightening with a good number of people contributing and a great deal of imagery (main black patent leather) for most of us sub to feast off for the next week.
The Dungeon play was great fun again and Miss Blue and Akasha wre the perfect hosts as always and the crowd (us subs!) were quickly worked up into a frenzy.
Perhaps we should compile a list of Top 10 tunes to slut out on!

Friday, after I recovered from only 4 hours of sleep due to the chat saw the arrival of my Training Kit.
Instant excitement...my sissy clittie was pushing against my panties and precum spots were oozing (again!) and then realization that the "gates of hell" had arrived ready for the next lesson.
First reaction was there is no way that I am going to get my balls through that first ring let alone my sissy clit...I'll leave the rest of that for my lesson report.
I then saw the panites that Akasha had selected for me...or should I more accurately describe them as three strategic bit of pink lace with decorative bows! There are somethings that shouldn't be done in life due to the plain "wrong-ness" of them...one of them is men in thongs.
The first thing that I did after receiving the kit was to try the panties on. It was a mixture of pleasure in the fact that they had been picked out especially but also a massive amount of humilation when I caught the reflection of me wearing them.

After, I must admit a bit of prancing in my new panties, I saw the slave tag - and then got that sinking feeling when I saw the envelope with "Do not open until instructed" written on it. It is amazing how such a simple bit of stationery has played on my mind every since and will continue to do so...definately a case I suspect of curiousity killing the cat or very possibly humiliting and degrading the hell out of it.

Thank you to everyone on the chat again.

Thank you for my training kit.