From Stephen to Stephanie Pt. 02

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Story of growing feminization.
4.4k words
4.33
57.8k
25

Part 2 of the 5 part series

Updated 06/07/2023
Created 12/10/2015
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Chapter one

Samantha and Karen had set up the two meetings; they were both with friends of theirs, both with domme tendencies. My role was purely to take notes, at the first meeting I was introduced to their friend Louise as their secretary which I clearly found embarrassing, both Karen and Samantha both appeared to inadvertently used the word 'she' rather than 'he' to describe me, saying things like 'she'll be taking notes'. Karen made quite a lot of mistakes in her presentation which I without thinking corrected.

Once the meeting was over and we were alone Karen vented her fury on me telling me that I was there to take notes and not to contradict her, at the next meeting there would be no possibility of this as she would be taking the precaution of gagging me beforehand, I could not believe what I was hearing.

On arrival at the next appointment while we were waiting for their second friend to join us Karen produced a small black silk scarf from her handbag asking me as she did so to open my mouth, I refused to be gagged, Karen reminded me that I was dressed in female clothes, had no money on me and no ID, and if I refused she would just walk away and leave me, I simply had no choice but to agree. She forced the black scarf as a ball into my mouth then took the scarf from the strap of her handbag and after folding it into a strip tied it tightly between my lips forcing the first scarf deeper into my mouth. The final touch was for her to take the scarf from the strap of my handbag and liberally spray it with perfume, she folded it into a triangle and tied it over the lower half of my face bringing the two ends around to the front and tying them tightly in a double knot beneath my chin

This scarf has three effects, it hid the fact I was gagged, the tight silk moved in and out with every breath heightening the feel of it against my skin and the perfume filled my nostrils with every breath. I found my arousal rising again and longed for this whole charade to end

Jayne their friend at this second meeting joined us and fussed over me, she even commented how much she liked the scarf mask I was wearing, they all during this meeting at all times used the words 'she' and 'her' to describe me.

Once the meeting was over I felt huge relief, I reached up to remove my gag and mask, Karen insisted I kept it on until we arrived at the shops, at last I found myself thinking I'm going to escape from this nightmare

Chapter two

We arrived at the shop owned by another friend of hers, it had a plain exterior that gave away none of the secrets that lay within, in the foyer Karen told me to put my hands behind my back, before I realised what was happening she swiftly handcuffed me, I was now completely helpless.

'Now for some shopping' she said, I shook my head trying to loosen my gag and at the same time was trying to wriggle out of my handcuffs, both were much too tight for that, she led me through the door and I saw a shop very far to my expectations.

There was rack upon rack of skirts, blouses, dresses and gowns, one area at the end had a range of bondage equipment and crops and whips, there was obviously no male clothing anywhere and it was dawning on me that getting away might not be that easy.

Kate the store owner joined us, her first idea was that I should change my shoes, these were the low heeled ones I had worn all day, as I sat down I had a moment of relief thinking that I might be returning to normal male shoes. Kate then untied my gag; things seemed to be getter better however my relief was short lived as she almost immediately replaced it tying it painfully tight.

I saw that Karen had found a black satin hood on the bondage shelves, it was made with double satin so looked thick enough to exclude all light from the wearer and at the same time meant the wearer had the slippery satin against their skin, she pulled the hood tight over my head, I struggling and kicking out all the time, there was to be no escape for me, as she pulled the hood down over my head I'm sure that I sensed a shudder of excitement passed through her, perhaps it was the feeling of having total control over me that she was enjoying so much.

I gave up my struggles and immediately became still, all resistance had gone from me, I felt Kate remove my shoes and replace them with a new pair.

I was helped to my feet and made to walk, I was very unsteady initially, Karen said afterwards that she saw an immediate change in my walk; my shorter steps really began to make me look more feminine

I was then helped to sit before my blouse was unbuttoned and something placed on my chest, whatever it was appeared to be then glued in place.

I was led across the room and was forced to kneel on some type of stool, my captors were quick enough in releasing my handcuffs and then attaching my wrists to the straps on the side of the stool giving me no time to resist, my ankles were then to the stool, I was by now totally helpless with my bottom raised slightly

This was obviously too much temptation for them, they began to beat me with what felt like a riding crop, I tried to call for mercy through my hood and gag, those cries seemed merely urged them on to make them want to beat me more, I heard one of the girls say how aroused she was by the scenario.

After a while the beating stopped and someone began to caress my hood and blouse, ensuring the satin rubbed into every pore of my skin, they stopped and I relaxed only for the beating to resume again.

This process of pleasure and pain for continued for around an hour, I found myself intensely aroused and was leaking pre-cum into my panties, why was pain arousing me I thought. At last I was left alone with my thoughts, I just wished at this moment I could return to my old life, I wished that I treated my wife better, her leaving had been the start of a chain of events leading to the situation I was now in.

Chapter three

I passed a very difficult night, my restrictions were tight and I could hardly move, my jaw ached from being gagged and had virtually no sleep, on top of all this I was terrified as to what was to happen next. I then heard the click of high heels on the stone floor of the shop, whoever it was took their time knowing full well that the fact I was still hooded would increase my sense of anticipation, I tried to plead for release as the person came closer but the only sound the tight gag allowed me to make was a mumble, my useless pleadings became more urgent as this unknown person ran the soft leather of some sort of flogger down my back

Quite suddenly my hood was removed, once I got used to the light I saw Karen in front of me, she was dressed in a long leather fishtail dress with matching full length leather gloves, she looked very feminine but at the same time very dominant, what alarmed me more was the leather flogger that she was carrying in her gloved hand, I was terrified and I'm sure that fact was obvious to her, I realised I was totally under her control and she could do anything she liked to me. She gave me a few strokes with the flogger, just hard enough to sting and to give me more pain.

At last my gag was removed and I was untied, I stretched out trying to remove the cramp from my night in bondage, I was taken aback at the sight of my 'breasts' straining the satin of my blouse, these had been applied these after I had been hooded the previous night, I then reached down to remove my high heeled shoes quickly realizing they were locked in place, I looked at Karen pleadingly, She shook her head saying that she would decide when they were to removed.

Karen and Samantha and sat in front of me, I was thinking 'what have I done to deserve this?'

Karen and Samantha spoke in turn telling me that they would let me ask questions in a minute, firstly they wanted to discuss the fact that they were sure that at this moment all I wanted to do was escape. They pointed out that physically would be difficult as I still was locked into the high heeled shoes making running impossible, I was in fact still dressed exactly as when we had left the island all of my clothing was feminine, again they said even if I did escape it would be very difficult for me to explain that! The final thing to ensure my compliance appeared on a TV screen across the room, they must have had hidden cameras everywhere for there was a slide show of me during the time on the Island, the pictures showed me dressing in my room with no apparent coercion, showed the moment I asked for my corset to be tightened and even showed me asking for help putting my stockings on. The final pictures showed me smiling as we left Karen's house as I fastened the knot on my headscarf and being gagged in the office of Karen's friend, my hands down at my side and apparently very compliant. They were damming shots, I appeared due to the way they had been taken to be happy and very willing to be female.

Just as though that wasn't enough Samantha explained that Karen would confirm her story that I had asked to work on the Island so I could express my feminine side, they had even used the bank details I had given them for my pay to make most of the clothing purchases so it looked as though I had bought them. Kate the owner of the shop joined us as did the two ladies who had been present at the meetings earlier in the day, all three of them gave what would be their version of events if I tried to get help, those versions showed me as a willing participant, I was by now shaking with fear, this before Karen said if I tried to get help or escaped she would publish all of the photos on the internet, I knew now that I was totally trapped

They asked me for any questions that I might have, my mind was racing at this point, the first question was why me? Karen answered that one 'because you were lucky enough to be chosen by us, you happened to come into our lives at the right moment'; my next question was' how long was I to be kept a virtual prisoner?' Samantha dealt with that one 'until we choose to release you, that could be weeks, months or even years, you are totally in our hands'; Next question I had was why the feminization? Karen's turn to answer; 'because eventually you will accept it and it will make you a better person, you will not be allowed to wear any male clothing again and in fact even female trousers are banned, you'll always be in skirts or dresses, we will be the ones who decide what you wear'; The next question I had was about the bondage, Samantha spoke ' Because it emphasises your submission to us and you will grow to enjoy it', my final question regarded the punishment I'd received would the beatings continue? Samantha smiled as she answered that ' it was all about submission and dominance, it gives us a great deal of pleasure to inflict pain on you, pain and pleasure will to be a permanent part of your new life.'

At this point I started to plead with her to let me go and return to my old male life, she was prepared for this and while the other two girls held me down she took a large ball gag with a leather strap and forced the ball into my mouth and locked the strap in place, despite the fact my hands were free there was no way I could remove it.

Karen then told me that my next job to choose her my wardrobe, I had the run of the shop for the next two hours, she wanted me to choose the most feminine items I could find, they had all to accentuate my new persona, as an encouragement to be careful what I selected, any item I selected that I deemed not in keeping would result in five strokes from the flogger.

I walked into the main body of the shop, my corseted body felt even more feminine with the addition of the breast forms and the high heels really did change my walk, there was one thing missing Karen realised, she called me back and placed a leather shackle around each of my ankles before linking them with a short chain, my stride was now effectively hobbled..

Two hours later they came back to the shop, I had placed a pile of clothing on the counter and I stood meekly beside it her eyes downcast, I was obviously desperately hoping I had made the right decisions.

They went through the clothes separating the items into two piles, one that they found acceptable, the other pile the clothes that they did not find feminine enough. I appeared to have done well, virtually all of the clothes were in tactile materials such as silk, satin, leather and PVC, they were in the main very feminine with high neck and back fastened blouses included, the longer skirts were a mixture of hobble and pencil whilst the mini-skirts were all pleated or just simply flared and all short enough to ensure they would barely cover my stocking tops, the dresses I had chosen included some really tight fitting gowns which would have the effect of restricting my movement. I had also done well with the underwear and nightwear with a selection of corsets and suspender belts catching their eyes, they were pleased to see that I had without prompting selected some bra's, I obviously had accepted that the breast forms were to be a permanent part of her future life, I had chosen a selection of scarves, this included several small black ones, the only purpose of these would be to use as gags, again showing my acceptance of future bondage.

Where I had failed were two cotton blouses, (these were definitely not sensual enough), two pairs of tights (something they would never allow me to wear in place of stockings), I had also failed to select the satin maids outfit and the cream satin wedding dress which they had placed in a prominent position. They collected all these things into one pile slowly counting them out. I must have looked crestfallen; these errors meant I would receive thirty strokes with the flogger!

They wanted to make the anticipation part of my punishment so they blindfolded me with a silk scarf and told me to stand facing the wall with my hands in front of me. I was to wait there until they decided the time was right to start

Obviously my hands were free and I could remove my blindfold (unlike my gag which was still firmly locked in place), they told that if I did remove my blindfold my punishment would be much more severe. They left the room making sure I heard the click of their heels on the hard floor, there was a web cam in the shop which they could watch from the back office, it was fascinating they told me afterwards to watch me, I had remained motionless waiting for my punishment to start, Karen had deliberately tied the blindfold quite loosely and being slippery silk it gradually slid off, I was so frightened by the possibility of more punishment so I re-tied it myself, doing so really tightly, another sign of my submission.

The thirty minutes that I waited seemed interminable, I felt myself tense as I heard someone in high heels walking slowly and very deliberately towards me, I was expecting the sting of the flogger at any moment, and was also uncomfortable from standing motionless for such a long period in the unaccustomed high heels.

I felt a heavily perfumed silk scarf being tied over the lower half of my face just as it had done before with the double knot at the bottom of my chin, I could feel the silk moving with every breath and my senses were increased by the removal of my power of sight and speech, the silk against my face coupled with the perfume filling my nostrils was be a very erotic sensation, she walked away slowly after telling me not to remove either of the scarves

Afterwards they told me that watching me on the webcam I could see me shifting my weight from foot to foot to relieve the effect of the high heels, they could also see the silk of my mask move with every breath the lustre of the material catching the light.

Another thirty minutes had elapsed before Karen returned, I could somehow sense it was her, I was led to what I later found out to be the St Andrew's cross on display in the corner of the shop and my arms were raised above my head before they were fastened to the straps at the top of the cross, she ensured they were high and tight enough to make me stand on tiptoe even with the benefit of high heels, this she knew would increase my discomfort further, my legs were then forced wide apart before my ankles were strapped to the bottom straps of the cross, I was now totally helpless and immobile, next Karen ran her obviously gloved hands along the inside of my legs carefully avoiding any contact with any of my sexual areas, I felt myself shiver visibly at her touch. Her final action was to replace the satin hood over my head confining me to total darkness.

I was left for fifteen minutes on this occasion, despite my restrictions I felt myself tense as I heard the sound of her heels approaching, she began my punishment, and five very hard strokes with a minute between each one, then a wait of five minutes before a further five were administered with a two minute interval between each one. She stopped at this point, I was of course was expecting at total of thirty strokes and remained tensed expecting at any time more pain, she left me for a further fifteen minutes before returning to administer a final five strokes with a three minute interval between each one.

At this point she released me from the cross and removed my hood, blindfold and gag.

Chapter four

Karen took me to Kate's flat above the shop where I had some breakfast, I was completely exhausted by the events of the morning and the previous night, Karen suggested I took a bath which she would run for me, she called me once it was ready, helped me out of my clothes and left me to soak, she had unbeknown to me added a depilatory foam to the water, she knew it would sting slightly nut fortunately I fell asleep, only realizing the effects when I awoke and was shocked to have a nearly totally hairless body, all she needed to do afterwards was to help me shave any remaining areas.

Once I had dried off and put on a satin dressing gown she took me through to the adjoining room where Karen had laid out my clothes from the selection I had made from the shop. The first thing she did was to put on a black satin gaff, this one was lockable, incorporated a butt plug (which I initially resisted) and effectively worked like a chastity belt, she reminded me that her control over me was to be total and that included sexual dominance, I would only be allowed sexual relief when she chose. The thought of this was quite delicious to her, she knew that I was aroused by all of the new sensations she had introduced me to, allowing me little or no relief was another part of my domination that she clearly really enjoyed.

Next she took the responsibility of ensuring my breast forms were securely fixed, the removal of my bodily hair made the adhesion firmer made it impossible for me to remove them for at least twenty four hours. she helped me with my corset, this time an over-bust one in heavy black satin, I was by now becoming used to extreme corseting and it was easier for her to tie the laces even tighter than before giving me a really narrow waistline, this when combined with my breasts made me look so much more feminine than previously, black seamed satin topped stockings and a pair of black satin French knickers completed my underwear, she took her through to the next room where Kate was waiting to do my hair and make-up.

The room deliberately had no mirrors, they wanted me to wait until I could see my total transformation, despite my apparent submission so far they wanted me to feel dominated even at this point so they tied both my arms and legs to the chair making me totally helpless, Karen went back to the other room to wait for Kate to finish and for me to make my first public appearance totally en femme.

It seemed to take a long time for the make-up and for my nails to be painted, Kate put a bobbed blonde wig on me and then helped me dress, and Kate had changed Karen's selection of clothes to some that made even more feminine. I wore a black blouse, this was made of rich and heavy satin which caught the light as she walked, it was back fastened (and had I knew a small padlock at the top of the fastenings making it impossible for the me to remove it) it had a high collar and long very full sleeves gathered into long narrow cuffs, this blouse was teamed with an elegantly restrictive mid-calf satin hobble skirt, this had no splits just a small decorative kick pleat at the back, my shoes were high heeled stilettos in patent leather.

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