Lesson 6: Sissy Titties

First let me come clean and state that the thought of you in a sexy sundress was extremely appealing particularly as it was hot whether here and the Maxipads were acting like a small oven keeping my clittie warm but making it pretty uncomfortable for most of the day.

Then there was the rather large distraction of making a choice...I had got rather used to being told what to do so this needed extra care. I decided to go for the Titty Torture in the end, although the makeup counter would have been pretty difficult I felt that I should do some thing to cheer you up and make you laugh if you have another stressful day.

Therefore I decided to humiliate myself to the max by sissying up and dancing for you.

I purchased the archetypal slut-red 1/4 cup bra with peepholes and was served by a man trying to make polite chat and in an effort to get out of the shop as quickly as possible got upsold a pair of crotchless skirt/panties to match. Anything for an easy life.



Resplendent in my new outfit I started to stroke my clittie, which again was oozing precum into my panties which was soon applied to my nipples that were now standing to attention because of the lacy trim around the bra and the peepholes.
Thirty minutes was a big test as there was alot of precum and having to slow down as I neared the edge of my clittie wanting to fill my panties.
I now realise that this was not even the start of the trial as I applied the clothespins for 15 mins.
The first 3 minutes were bad and every time I caught the clothespins pain shot through my nipples. After 10 minutes I got into the swing of things and got a bit more daring with my twisting and tweaking.
15 minutes were up and the pins came off. Owwwwwwwwww....Thank you for that. As the blood rushed back in I felt stomach churning pain particularly when I tried to tweak, twist or gently rub them.
I was counting down the minutes until 15 and then greatfully started to ice my nipples. This was a great relief and I am sure steam came off them.



Next was the dancing...and the realisation to my dismay that the clothespins would have to go back on!
With a lot of lip biting, wincing and the odd tear in my eye the clothespins were reapplied and I began to dance to a slut collection of tracks that I had been planning earlier in the day.
I have sent Akasha a seperate email with a sample in...not out of vanity, not to show off, but just to make her laugh if her day has been stressful.

I finish this post with my nipples still glowing red hot...

As always thank you for the lesson.

Lesson 5: Sissy gets her period

Having not had an internet connection for 2 days has been bad as I have been desperate to find out what Lesson 5 would be..and hear it is - again a mixture of excitement, apprehension and examining myself again and a very tight deadline...

My nipples are still glowing and tender after the twisting and pulling and digging in of nails. Each time I catch them under my work shirt they give out a little protest but it reminds me of my training.

Having managed a number of shopping trips already I wasn't nervous about this one - it was more important for me to get it done to get the task completed for today. Perhaps this is my pride/self conscious slowly being stripped away but I was happy searching through the aisles of feminine products for the Lesson shopping list - or perhaps I am just a desperate sissy slut.

Dressed in panties, hose, tucked and without socks I went to the supermarket and purchased the items. It was very clear that the checkout girl thought that the purchases were funny, I hadn't really been ready for this and dropped my wallet and came up a fairly pink shade. She knew that something was up.



So armed with my Maxipad, Scented Pink application Tampons and FemFresh Deodorant I set about the next part of the lesson. As I was due for a business meeting around the corner at 9:45am I had got to the store at 9:00 knowing that I wouldn't be able to complete the next part of the lesson at home.
I went around the store again and bought my trusty cucumber ( I already had the condoms) and headed for the store restrooms. I locked myself in the cubicle and with my hose and panties around my knees practised my cocksucking for 30 mins.

I was worried that I would be late for my appointment so I left the store (only to realise that the toilets were monitored by CCTV!) and drove round to my clients.

I was 10 minutes early so I stashed a maxipad and the lipstick into my laptop bag and went into my clients and asked to use the restrooms - I snuck into the disable toilet so no one could be in there at the same time.
The cocksucking, anticipation of the task and general excitement had meant my clittie was still oozing precum. I applied the maxipad to my panties and then I took off my work shirt and rubbed the precum over my lips and nipples. I felt pretty decadent and desperate and my clittie was throbbing with excitement.



I remembered the instructions to apply lipstick over the precum so I took this literally and applied my slut red lipstick to both my lips and my nipples.



The effect of the lipstick on my nipples was a big mental blow to any ego I had left. I don't know why but this made me think that I must be pretty pathetic and desperate to be standing in my clients disabled bathroom, licking and smearing my own precum, wearing lipstick, maxipads desperate to try and provide entertainment someone who had told you to do it.
I'll leave it to the imagination as to what I saw and thought looking into the bathroom mirror as I told photos as evidence.

I was far to cowardly to go to a meeting with lipstick on so I removed the bright red from my lips and scrubbed had at my nipples with wet toilet tissue. This just enhanced the fact that my nipples were still sore after the tweaking.
Then there was the experience of walking wearing a maxipad - or should I say rolled up hotel towel. It felt like Iwas tring to walk with a small pillow between my legs. When I sat down it just made me aware that I could feel it pressing against my clittie and ass.

I am now onto my second maxipad and now carry two laptop bags with me. One with a laptop in it and one full of hose, panties, pads, tampons, femme fresh spray, lubricant, lipsticks, whipped cream, cucumbers and condoms.
Getting stopped at customs when I fly later this week might be interesting!

The thought of the being pumped full of hormones to feel really female is pretty frightening, the thought of losing that much control over my body would probably have me near tears and pleading for leniency....and that wasn't a complaint or whining just being a little bit scared about what might come next.

Once again thank you for the lesson.

Apres-Chat Wind down and Thank you

NOTE: This was written on Friday evening but due to tech issues is not posted until today.


Quite frankly I don't know if I'm coming or going at the moment after the web chat with Akasha and the other sluts last night. Very early morning for me.

A work colleague remarked to me this morning that "I looked buggered!" (English colloquial for tired, also meaning emotionally up a creek without a paddle - check out any Hugh Grant films for reference e.g. Notting Hill, and also meaning being taken anally!)

How correct on all three counts and astute - my reply however was a simple "If only you knew". I still have a grin on my face and my hips and ass are still sore from the rocking on my fingers!

Anyway I wanted to keep it short and thank everyone on the chat last night - it was great fun, a fantastic group effort and I trust everyone got overexcited.

Butler

P.S. Gifted with hindsight and Akasha mentioned she would like to put a link to my blog I have a couple of questions and would like the advice of any readers:

1. Can anyone recommend a type/style of Butt Plug for beginners (after the Chat on Thursday I'm still suffering from my long nails!)

2. The same again for a Dildo is any type and style better? (Through the training I have now got through 4 cucumbers and they go mushy at the end after one use and being left overnight!)

3. Can anyone recommend a way of getting lipstick marks out of panties (see Lesson 4 Part 2) otherwise I will have to write that pair off!

Lesson 4: Sissy laps it up - Part 2

Well having struggled for many hours I sent my video clips off to Akasha and I sit here hot, bothered, and very submissive.

I decided to put on the bright red lipstick for that extra slut factor.
Having spend days tucked, pantied and taped my sissy clittie was finally aloud a cum explosion.
It took less than 30 seconds for me to explode fom having got down on all fours and played with my clittie through my hose and panties.



It was a relief, short lived and a little hollow knowing what was to come next. I eased off my pantyhose and stared down at the oozing mess my clittie had made of my panties. I eased my training panties down my legs being carefuly not to drop any as I really didn't want to start licking the floor. I then got back on all fours, shut my eyes and then started to slurp up my cum from my panties.
I felt almost numb as I knew that this was going to happen before the event, and resigned myself to the fact that I was licking up my own mess that I had made.
Cum on my lips, my panties and now swallowing and licking it down. I felt shameful and a little bit apprehensive about what I might do next? Where would I stop? Would I?

Then the picture that had been painted about cleaning up for Akasha came back into my head and my pride lifted a bit. At least I would be useful for something...and I sucked on my panties with a little more enthusiasm after the initial shock.



I sit here typing away, in a bit of limbo but can't quite stop wondering...What are you going to do with me next?

Well - reality check panty laundry to be done.

Thank you once again for my lesson.

Lesson 4: Sissy laps it up - Part 1

The lesson for me is all the things that I was warned about by my brothers not to go near when trying to deal with the dominant sex!

The Quality vs Desperation Dilemma in selecting a clip

...and the

Do you think he looks attractive Dilemma in trying to second guess what guy is hot

The first part of lesson four left off straight from Lesson 3 - it is the first time in my life that I have ever come to edge in about 6 strokes through my panties and hose without even having an semi hard clittie. Having read the rest of the lesson cleaned up the precum with my fingers and sucked them clean knowing now that messes will not be tolerated. The next two times to the edge were achieved by rubbing my clittie again within another 3 minutes of each other.

Creamy Cocksucking was a relief after this as it distracted me from my now constant arousal, desperation and embarrasment about my need to rub my little clittie to explosion.

My days and nights now seem to be more frequently puncutated by wondering about the training. How can I best do this, what the hell with the training kit bring and a whole host of apprehension, fear and excitement.

As I don't have a webcam I am unable to offer my services and participate in a live performance. I still do not think that I am good enough as I cannot stop the gagging and choking still. It is one thing to practise in private but either by cam or phone under instruction/monitoring would no doubt throw me off my stride and I would only embarrass myself.

Well after an initial 4 hours searching on YouTube I haven't found the perfect thing yet...having trawled through clips of gay bondage, straight bondage, strange Smallville compilations and it seems to me endless video of College/high School kids messing about with Duct tape.

The search goes on...

Lesson 3 - Creamy Cocksucking Day 2

Just a quick update today...

I must admit that my clittie is a mess at the moment. Every time I need to relieve myself when I untape and untuck it now seems to always be accompanied by a string of precum. It is looking a little red from the pulling of the tape and I seem to be in a state of arousal without any effect on my clittie without except little leaks of precum throughout the day. I think that this may have been caused by the fact that I ordered the Slave Training Kit and I haven't stopped thinking about it - I even lost sleep thinking about it last night.

Cocksucking Day 2 was alot better today, my jaw ached far less after 30 minutes of action. I tried to be more vocal today, but initially probably sounded like a 70's Porn film, I managed to push the cucumber to the back of my throat today and manage to sort of utter the words 'Thank you'. I am still having massive problems with my gag reflex. I will do some more research today to see if it can be trained other than practise.
This is something I am determined to get right.
Unfortunately I couldn't capture the "best" action (and in my case humiliating action) today on film as I need both hands to stop myself from retching.
Having started slowly at an easy pace yesterday sliding in and out it damned on me that perhaps a future user of my slut mouth would not be so gentile, so I stepped up the pace and started ramming the cucumber into my throat.
On my knees with my elbows on the floor, prone, both hands clasped the bottom of the cucumber dildo and rammed home as far as possible about once a second. The first 4-5 strokes were manageable but the I needed both air, breathing room, and a chance to regain my senses. Strokes 6-7 we met with garbled gurgling and choking, before stroke 8 caused me to go through the retching motion, tears in my eyes, almost bite into the cucumber and forcibly eject it out.
Not to be beaten I knelt there panting and breathing heavily for ten seconds before trying again. It was pretty much the same result, and by now even with my eyes open I was looking through tears and had left a trail of saliva down the cucumber, that had now started to run down my forearms.
I slackened of the pace again for about 10 min's gentle suckling, nurturing, licking, and swirling and then tried the more vigorous stuff again.

Lets see how I do tomorrow!

Lesson 3 - Creamy Cocksucking

After the weekend of running repairs, wash day for training panties and purchase of a new pair of Control Top hose after managing to put a ladder down my first pair, I wasn’t quite sure what to expect for Lesson 3.

I am starting to get used to the routine of taking medical tape with me to the bathroom, wondering if people can hear me ripping tape with my teeth before “tucking” away my clittie. All taking probably making anyone sharing the bathroom at the time wonder.

One thing that still sets me on edge is that the Hose make an audible “static” sound when they rub against my suit trousers making every step sound like I’m charging through Autumn leaves, which in turn reminds me that I “might be found out”, which in turn reminds me of the training.

I must admit to enjoying the feeling of being controlled by the tucking exercise.

Back to Lesson 3...

I no longer have a Dildo even though I previously completed a training last year. I was pretty embarrassed about myself at the end of the last training and I threw everything away, probably denial. Still all good things come to those who wait and I back enrolled in training with more even more purpose.

It is ironic with the shopping list given that I was most embarrassed choosing a cucumber as I actively had to make a selection rejecting too curved ones, too skinny ones, and generally having to guess how thick I may be able to manage. This again had the effect of straining my tucked clittie and causing that “pulling discomfort” making it difficult to stand let alone walk.

It was also the first time at the till that I felt that the cashier was wondering about my purchases as they were a bizarre lot.

Having returned from shopping I locked the door of the office and decided to get to work with the new lesson. I first put on the new red lipstick to try for color.

For me a condom goes a lot further down a cucumber than I remember, I had one of those out of body moments and felt pretty small and humiliated about what I was doing, rolling a condom onto a cucumber, squirting cream onto it knowing that I was about to lick, slurp and glide the cucumber into my mouth because Akasha had asked me and I was pathetic enough to do it because I wanted to not impress her, but to please her.

Fact 1- I have now decided that UHT Light Squirty Cream tastes foul and nearly makes me gag(!) on its own. Fact 2 – Mixed with lubricant doesn’t help it taste any better.

Licking around the tip and shaft of the cucumber again caused my tucked clittie to become more noticeably to me bound, contained and stretched by the tucking tape. After about ten second the taste of the cream mixed with the lubricant of the condom as I was working down the length in small circles and again made me sick at myself for what I was doing.

Having removed the cream from the cucumber and licked up the bits that had dropped onto the floor I closed my eyes and began to work taking the makeshift dildo into my mouth. After three or four thrusts I opened my eyes and was slightly humiliated and surprised to see the red lipstick that I had applied smeared around the top of the dildo. I think this was the point that crushed me more than anything else, and proved to me, that I was in fact pretty pathetic and desperate to do this lesson as well as I could.

I continued to work on shaft and head action remembering when I could to open my eyes and try and look bambi-eyed in case I am ever watched. Noises included little whimpers, sucking sounds, gentle kisses and myself catching my breath. When I had plucked up the courage I decided to take the Cucumber as deep into my throat as I could manage. Whimpers, sucking and light breathing were replaced instantly by shut eyes watering, guttural retching and panting.

I tried again with much the same effect and needed three or four attempts before I didn’t completely clamp down with my lips on the shaft so that if I am asked to perform on the phone my more base, gagging sounds could be heard. In this stage I even found myself thinking , Let me have another go – I can keep my mouth open, as if I was starting to beg for another chance to perform better.

Tomorrow I will work on deep throating with my eyes open. But all I can say is 30 minutes is a very long time to suck cock.

I am still slightly hoarse and have jaw ached from my first attempt.

Here are the photos that I managed to take. Trust me it’s even worse for me when I look at them.

All I see in the first is Chipmunk and Scared, Wild Eyes in the second!