From Stephen to Stephanie Pt. 03

Story Info
The ongoing feminisation.
3.7k words
4.24
42.8k
15

Part 3 of the 5 part series

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

As we drove towards the airport my mind was a mass of emotions, the last ten days had been a complete transformation in my life, one of the things I was struggling to understand was how permanently sexually aroused I was, it seemed that I was enjoying expressing my feminine side, something I still wanted to fight against.

I found this really difficult, the sensation of the tight corset and of the silk and satin around my body seemed to raise every part of my sensuality, the tight skirt forcing my legs together further increased my arousal, even the way my headscarf was tied with the silk on the edge of my cheeks and the silk knot just touching my lips was a part of this new sensuality I was experiencing. The fact that I still had the butt plug inside me made the feelings of femininity stronger

I closed my eyes and tried to blot out everything and tried to think of things outside of the sensations I was experiencing, I felt myself drifting off to sleep and beginning to relax as I remembered life as it had been and as I could forget about the situation I was in.

My peace was short lived, a low buzzing noise started and the plug inside me began to vibrate, it was almost unbearably arousing, I opened my eyes to see Karen smiling at me from the front seat of the car, she held a small remote control in her hand, I saw her fingers move and the vibration started to increase. I tried to fight against the sensations but found myself crying out as I got closer to orgasm, at that moment her smile broadened and she switched off the plug, I was trembling violently and almost sobbing with frustration. Karen's smile broadened as she said that next time she might just leave it on!

My headscarf had slid off during this interlude and Karen told me to put it back on and to ensure that it was tied exactly as before with the silk just caressing my face, the action of doing this made all of the sensations and sensuality of my femininity heightened, Karen made these feelings even stronger by asking me if the satin of my blouse and skirt felt good, I at this moment both hated and loved feeling feminine.

We stopped for lunch at a small pub, this was the first time that I'd been in a totally public place, I tried to insist that I wasn't hungry and that I'd stay in the car, Samantha and Karen would have none of this and insisted that I joined them reminding me that all of the photos of me were just at the click of a button waiting to go on to social media, as I walked from the car to the pub the high heels and hobble skirt I was wearing at least helped making me walk in a very feminine way that matched my appearance

At one stage during lunch Samantha suggested that as I was not hungry she might as well gag me, she opened her handbag a little and I could see the ball gag inside, I was so frightened but luckily she laughed and said on this occasion she was only joking.

After lunch we drove on to the airport and took the flight back to the main Island to catch the boat back to the smaller island where Karen and Samantha lived, it was evident to me that climbing on to a boat in my hobble skirt and high heels would be impossible, I asked Karen how I would deal with it, she replied that I shouldn't worry as we were going to stop at a friend's house to enable to change into a pleated skirt and some flat shoes, I reflected at this point how much had changed over the last two weeks, if anyone had suggested at the start of that time that I be relieved to be putting on a pleated skirt I would have thought it a mad idea

We stopped at their friends house, they were away and Karen had a key, we let ourselves in and Karen handed me a carrier bag and told me to change , the bag contained a pair of flat shoes and a pleated skirt as promised, it was only when I took the skirt out that I found it was made of heavy black satin and was incredibly short, I put it on and found it just covered my stocking tops, it would be very difficult to wear and to retain any form of modesty, I asked if there was an alternative but was told firmly that I had to wear what I was told to, I had no choice in the matter. At least I found some relief once I was dressed in wearing flat shoes, I was allowed to retie my headscarf in a Kelly style and I was ready to go

At least the weight of the satin of my skirt stopped it blowing up too much with the wind, I found however that I kept having to adjust to remain decent, both Karen and Samantha were obviously amused at this, when we arrived at the island they had one last trick up their sleeve as they handed me two carrier bags to carry, this of course meant that as I left the boat I gave the crew a flash of stocking top, I felt so embarrassed but at the same time was quite enjoying the breeze around my legs, another confusing emotion for me.

We supper together and Samantha after unlocking the padlock at the fastening of my blouse asked me to change into my ivory nightdress and dressing gown so we could watch television together, It felt lovely to be out of my corset after wearing it all day and the flowing satin of my nightdress was cool and slippery, for a brief moment I felt relaxed

When I got back to the living room both Karen and Samantha were there, Karen was carrying oddly enough an ice bucket and Samantha was holding something behind her back, they told me to lift up my nightdress, this of course left me exposed and showed that I had an erection, Samantha took her hands from behind her back revealing that she was wearing satin gloves and had a blindfold in her hands, she blindfolded me and then I felt her hand gently brushing my erection, the satin of her glove making it even more sensual, I thought for a moment that my sexual frustration might just be relieved

At that moment I suddenly felt something very cold, my erection shrank away and I felt something being slid over my penis with a click happening next, I took off my blindfold to find something like a plastic cage around my penis, I tugged at it but it was firmly locked in place, Karen spoke first saying that it was a CB2000 chastity device, I would be wearing at any time that I didn't have the locked gaffe in place and that meant I would be sleeping in it, the girls had decided that their domination of me must be total.

I started to cry, this was just too much for me to bear, Karen sat beside me her arm around me as she stroked the satin covering my body, she began to tease my nipples and I felt myself becoming hard, of course the CB2000 prevented any full erection, it was so frustrating, the other issue with the device was that I now had to sit down to pee, yet another item of feminisation

Chapter two

Karen and Samantha liked to taunt me, I discovered that my male clothing had never been lost but had in fact been in the house the whole time, Karen had a glass fronted cabinet in her study and all of my male things including my ID and my wallet were locked inside on clear display, the cabinet had toughened glass and a substantial lock, even if I was alone in the house it would have been impossible for me to break into it.

The worst thing for me was that the whipping horse that Karen had installed faced directly at it, the result was that during my punishments I was within inches of this vision of my old life.

I did on one occasion manage to use Karen's mobile to call my wife to ask her to forgive me and to come back to me, my wife's response was very cold, that upset me greatly.

The next two weeks were a blur, my training continued, I had to wear heels all day to allow my feet to adjust to them, by the end of each day I was so relieved to take them off! My training in walking and moving like a woman was continuous, the training even covered my hand movements, as the time went by I could feel it almost natural. My corset training continued with it being tightened every day and included me sleeping in a training corset; I was also taught how to do my own make up. I was disciplined if I got things wrong and had quite a few beatings during each day. A voice coach was brought in and I did daily lessons to change my voice to a more feminine one. On the last day of my initial training Karen and Samantha said how pleased they were with my progress.

What they said next was alarming, they were planning a party for a few of their girlfriend's, the whole idea of this party was to show off Stephanie, that was to be my name in future, I was to act as maid greeting the guests and serving drinks during the party, Karen showed me the dress I was to wear, it was a classic French maids outfit in heavy black satin, it had a high collar with a lock at the back, long sleeves with locks on the cuffs and a very short skirt pushed out by a layer of petticoats, I could see that it would barely cover my stocking tops when I was standing upright, bending over to serve drinks would make me feel incredibly vulnerable, Karen also said that I would need training in how to curtsy properly before the party. I pleaded with her not to make me wear this dress; the reaction to my pleadings was to be gagged for the rest of the day until I learned some manners.

I was going through real uncertainty; it now felt normal to be dressed totally as Stephanie, wearing high heels and a tight corset were part of my everyday life and being surrounded by satin and silk everyday almost made me forget my old life. However I was still determined to escape, the fact that I could see my male clothing on display gave me hope that one day this nightmare would come to an end, the opportunity to escape came sooner than expected.

Karen and Samantha were going to be away for a couple of days, they had no concerns about me trying to escape as I had no money, no ID and no access to male clothing, they left on the Sunday and I was now desperately trying to think of a plan of escape

I went into Karen's study not thinking clearly, I noticed the roll top of her desk was ajar by a fraction, opening it up revealed the keys to the cabinet that contained my male clothing, she had obviously failed to shut the desk properly, this was my chance. I opened the cabinet and retrieved my clothing; I was pleased to find my wallet intact with cash in it and my driving licence and credit cards that would mean once on the mainland I could hire a car.

I took the clothes upstairs and firstly removed my make up before undressing, the major problem I had was that my breast forms were securely glued to my chest, the adhesive had only been replaced that morning and I knew from experience that it would be at least 24 hours before I could remove them, I then remembered that to wear during my exercises to lose weight that had been part of my training I had been provided with a sports bra, I put this on and it flattened by breasts enough before I got dressed, it felt strange to be wearing male clothes again, my waterproof jacket hid the shape of my breasts and I was ready to go.

I just made it to the last boat and got a taxi from the quay to the Island Airport, I managed to get a ticket for a flight that was due to depart within an hour, all looked good so I enjoyed a drink at the bar and began to relax, the check in desk opened and I went straight through to security, taking my jacket off for the scanner did expose my 'breasts' a little but not enough to arouse suspicion, the scanner however did bleep despite me removing my watch and belt, the female security officer checked me over and I'm sure she felt the outline of my bra under my shirt, she asked me if I'd mind stepping into a side office so she could fully check my ID, I could then be on my way as this was merely a formality.

Once in the office she left locking the door behind her, I thought that a bit strange but dismissed it quickly; it was only when the other door at the back of the office opened to admit Samantha and Karen that my heart missed a beat. They were both smiling, Karen spoke first saying she knew that I would try to escape and that they had set the whole thing up with friends to test me, I was to return to the island with them or I would be exposed via social media, she showed pictures and videos of me on her phone which had been edited by them, these showed me asking to be feminised, if these were in the public domain my life would be impossible, I had no other option but to accompany them back to the island.

Chapter three

Once back I had to change back to Stephanie, once I had done that they asked me to come out into the garden, they then burnt all of my male clothing and ID in front of me. I was now trapped completely and have to admit that I wept at that moment.

My training for the party continued, I was made to wear the dreaded French maids dress and made to continue with every aspect of my feminisation, there seemed to be no chance of ever escaping

One morning Karen called me into her study, she handcuffed me and then produced a pill, by simply pinching my nostrils she forced me to open my mouth, she slipped the pill in and held her hand over my mouth until I had no option but to swallow

It was at that point she revealed what the pill was, it was a female hormone pill, my attempt to escape had led her to think that she needed to speed up my feminisation, I would in future take them every day, the results would be less body hair, a reduction in my waist as fat moved to my hips and a growth in the size of my nipples with a resulting increased sensitivity

Again I pleaded with her to stop and to release me, her answer was an emphatic no, I would never be going back to my old life, I would never wear male clothes again and I would slowly become more feminine. My feeble attempt at escaping had confirmed to her that the hormones needed to start earlier than they had planned, however there was one small piece of good news; as a reward,I would be allowed to have sexual relief soon.

The party was getting ever closer, I was taking my hormone pills on a daily basis, there seemed little immediate change apart from the fact I was a little more emotional at times, my skin felt softer and my nipple sensitivity was definitely increasing. My training was now all day, my movements were now really feminine and I had mastered wearing heels to such a point that I was regularly wearing 4'' ones. I still was embarrassed about wearing my maids dress and hated the clicks as the locks closed on my wrists and neck that seemed such a moment of total submission.

The day finally arrived, I was in the hallway waiting for our guests, my dress flared out by the petticoats, my apron in place, my wrists chained to my belt, my ankles joined with a short chain in a way that gave me some movement and my mouth filled with a locking ball gag, I looked the perfect submissive, I wished at that moment that I was anywhere else but in that hallway.

The doorbell rang and I hesitated, Karen told me not to keep the guests waiting, I opened the door to greet an older but very stylish and attractive lady called Emma, she greeted Karen warmly then stood back to look at me, she complimented Karen on what a wonderful job she'd done and said she loved my gag, after all she said servants should be seen but not heard, there was a stream of guests after this and I was soon in the living room serving drinks, my chains just giving me enough movement to do so but at the same time ly reminding me of my restrictions. As I moved around the room I constantly felt wandering hands reaching up my skirt, it seemed that every time I leaned forward it was too much temptation for one of the guests, I had a whole new outlook on the words 'sexual harassment' as the afternoon drew on.

I ended up on in one corner of the room offering Emma (the lady I had met earlier) a drink from my tray, she very deliberately and very slowly ran her fingers around my stocking tops, my chained wrists making it impossible for me to fend her off, this was in full view of the other guests and incredibly embarrassing and at the same time very arousing, I groaned with frustration the noise just audible through my gag.

Emma immediately apologised and asked Karen for the key to unlock my gag.

I stretched my mouth which by this time was feeling a quite numb having been gagged for nearly three hours, Emma smiled at me before sliding the large heavy silk scarf from around her neck and then stuffing it fully into my mouth, I could taste her perfume on it. once Emma had tied a second scarf in place I could make no sound.

Emma said to me that she was sure I felt better now! I disliked it intensely, the moment of freedom was had been lovely but so very short, being gagged again seemed to heighten all my senses and bring back feelings of arousal and frustration in equal measure

What was interesting was the fact the nobody else in the room took the slightest notice as to what was happening, it seemed quite normal to them that someone could be dominated and humiliated in equal measure in front of them, I went back to serving drinks to the rest of the ladies and continuing to be groped by them as though I was their plaything.

I was really glad when they started to leave, they were all staying in the holiday cottages on the Island and several said as they left how envious of Karen and Samantha they were for having such a delightful maid and how much they loved my outfit, several of them taking another opportunity to stroke the satin of my dress sending shivers through my body.

Emma was the last to leave, she kissed me full on the lips through my gag, it was very erotic although I tried to think of anything else that would remove these thoughts from my mind, she said that I could keep her scarf as a present. Karen then asked Emma if she would like to tighten my gag before she left, Emma was delighted and took great pleasure in doing so ensuring that it was painfully tight

Karen and Samantha were delighted as to how the party had gone, they said that Emma had been really taken with me and I needed to watch out as she had both lesbian and domme tendencies, if I didn't behave myself they would lend me to her

They were so pleased with my work that I was promised a reward, I thought that it would perhaps a relaxing evening or even a chance to dress in a less formal way, this was not the case, the reward consisted of having my nipples clamped for the first time, even more painful due to the fact that the hormones I was taking had already made them more sensitive, the second part of my reward was to have a larger butt plug inserted before being taken to the living room where I was tied in a chair with my nipple clamps attached by thin wires to the arms of the chair. The vibrating butt plug was turned on at a very low speed, just enough to keep me incredibly aroused and on the very edge of orgasm, I found it impossible to keep still with the result that every movement I made tugged the wires of my clamps on my nipples heightening the pain I was experiencing. I wished for once that they had gagged me as my cries of frustration and pain greatly amused the girls as they watched television

Eventually I was allowed to go to be bed, my CB 2000 clearly locked in place, and I was exhausted and still very sexually frustrated!

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AnonymousAnonymousabout 8 years ago
You goofed.

When you had the CB2000 put on him, Karen teased Stephen's nipples. How can Karen do that when he is still wearing the breast forms which are still glued to his chest. She can not when they are covered up by the forms.

Stephen had gotten to the airport. He should have told them to go to hell when the women showed up. He should have fought to not go back with them. He should have said that he would have them arrested for kidnapping plus other charges if they did not let him go and to destroy the pictures and videos. He should have ended the ordeal right then.

rdoolittlerdoolittleover 8 years ago
Better and better

You have hit almost all my fetishes with this series. The cb2000 and the foiled escape made this chapter for me. (5)

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