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.
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