From Stephen to Stephanie Pt. 01

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A story of feminisation from the side of a submissive.
3.3k words
4.39
85.1k
57

Part 1 of the 5 part series

Updated 06/07/2023
Created 12/10/2015
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It's a beautiful day and I'm sitting writing this at home, my wife is talking to a friend on the phone, in fact an everyday picture of everyday life.

That is until I glance across to the mirror and I see myself beautifully made up, my blonde hair in a ponytail and I'm dressed totally as a woman, this is the story of how Stephen became Stephanie.

I'd always been a bit of a 'Jack the lad', enjoying evenings in the pub and going to sporting events, looking back I'm certain that I wasn't a particularly good husband and certainly didn't support my wife properly in her efforts to grow her own business, she'd opened a small women's boutique and was doing quite well. She tried at times to ask my advice as to what she should stock, in her words to get the man's perspective, I tended to dismiss this as being 'woman's work.

It was still a huge shock for me when she left me, I never saw it coming, I knew she'd gained new friends and a new social life but the time I came home and found a note telling me she wanted a trial separation and that I was not to contact her until she was ready, I did try but was told firmly that if I tried again our separation would turn to divorce, I had to accept things on her terms.

At least life looked up on the jobs front, I'd always worked as a freelance and had been offered a contract by the owner of a small specialist publishing company (a bubbly and very attractive lady called Samantha in her mid-forties), she needed someone with specialist IT skills to sort her archives and I'd been offered a twelve month contract at a very generous salary, the initial part of the job was to sort the archives that were stored at her house on a small Scottish Island, once the archive was dealt with I'd be based in her London office

She asked me to start as soon as possible as the forecasts were bad and she was concerned about me getting to her. I flew out to the main island and took a boat to the outer island, the boat was operated by a young girl who was very friendly, and when I told I was going to work for the owner of the island she seemed amused, I couldn't quite work out why. The weather was pretty foul and I must admit feeling very queasy by the time I set foot ashore. My luggage had been held up at the airport and would catch up with me tomorrow; at least I had my laptop to start work. Samantha greeted me warmly and provided me with an early supper; I went to bed early to be ready to start tomorrow

I had a walk around the Island first thing, it was beautiful, there appeared to be only about six other houses and I only saw one that looked to be occupied, the sun was out but there still was a near gale force wind and the sea was amazing with masses of white horses and crashing waves breaking on to the shore.

Back at the house I had breakfast with Samantha, she gave me the bad news that the boat to the Island was not running due to the weather and that the airport had called to say my luggage had somehow been sent back to London and would arrive back later in the week, she was very sympathetic and said we'd muddle through, it did cause one major problem the fact that I had no clean clothes and more to the point no clean underwear.

Samantha said the fact that she'd had a friend staying who was about my size and who had left some clothes behind would solve the problem, I naturally assumed that friend was male and was very surprised when she returned with a pair of black satin French knickers, the lustre from the rich satin, shone in the light, My male ego insisted that should protest, but as she said no one was going to see them and I was being stupid. When I changed into them I found the caress of the satin really arousing, it was something I enjoyed but at the same time felt unsettled by. I made no mention of them during the day and we caught up with a mountain of paperwork

Little did I know that today was the start of my feminisation, Samantha later told me that she had felt a shiver of anticipation at the enjoyment she was going to experience becoming my Domme, the start had been easy and she had felt a moment of triumph, the first hurdle had been overcome.

The next day after I came out of the shower I found that Samantha had put a pair of a pair of ivory satin knickers on my bed, I didn't protest this time which she told me afterwards felt was a step forward, it was the first moment I had become submissive and was the start of my new role in life.

The gale force winds continued, I asked Samantha about the Island, she told me there were just seven houses on the Island, all of them were holiday cottages owned by friends of hers from London except one occupied by her sister who was an artist, she was working on a large project and it was unlikely we'd see any sign of her till the end of the week.

Samantha gave me the task of moving boxes of files from the archive room, the last dozen or so were much heavier (something she admitted later to have deliberately made so) I spent the whole day working and by the end of it was rubbing my back which was pretty painful from these unusual exertions, she suggested that I should have a soak in a hot bath and go to bed early, that should she reassured me relieve the back pain

The next day the foul weather continued and the Island remained cut off from the world, it was back to the black satin knickers for me, again I didn't protest, my back was still very painful, at this point I wasn't aware that she was planning the next stage of my transformation, she suggested that I needed some support for my back and went off and fetched a black satin corset, when I saw it I thanked her but said there was no way I would wear it, she was really upset and disappointed, she said that was only trying to help, I would only have to wear for a couple of days at worst, no one would know, it would sort out my back problem and she felt that I was being really ungrateful

After a while I gave in, she after all was such a lovely person and I did not want to offend her, the corset was an under-bust one and as she laced it tightly had the effect of lifting my chest to form small breasts, I was very embarrassed by this and kept my arms folded over my chest, at intervals over the next few hours she tightened the laces reassuring me that it would help my back

I noticed that the corset changed the way I moved, even with my loose fitting jeans and shirt I somehow looked more feminine and more worryingly felt more feminine, her plan of which I was still totally unaware of was to speed up my transformation, the thought of me totally feminised and in bondage was exciting her and she felt that her new submissive was appearing slowly before her eyes, she knew however that she would have to proceed carefully to make sure she trapped me completely

The next day we were still cut off from the rest of the world by the weather, my back was little better so once again she laced me into the corset, it seemed tighter than the previous day, I didn't argue about the corset or the knickers however when she produced a pair of opaque stockings I refused point blank to wear them, she pointed out my stupidity, firstly I had been wearing the same socks since I had arrived and they needed washing, secondly the corset had suspenders attached and I might as well use them, her arguments failed to convince me and she burst into tears, she sobbed that she was trying to help me and that I was being ungrateful before storming out of the room. I waited what appeared an age before I decided to give in and asked for her help to put them on, she did and made sure (unknown to me) the suspenders were as taut as possible.

I was by this stage increasingly confused, I felt that I didn't want to offend my new employer by refusing her loans of clothing but at the same time I found the stockings added another dimension to the sensual nature of what I was wearing, I wondered what my wife would have made of how I was dressed!

It was now Saturday, the day my luggage was supposed to arrive, the weather had actually worsened and not only were there still no boats were running but even the flights had been cancelled, the next one not due for another three days.

Samantha suggested we went over to her sisters for lunch, the jeans I had been wearing all week were by now filthy, she offered to lend me a pair of jeans but explained they were probably a size too small meaning that I would have to wear the corset, I agreed after a little hesitation as I was keen to get out of the house for a while, I didn't even protest about wearing stockings.

Samantha fetched the jeans and also a cream silk blouse, it was quite plain and she told me that it would be hidden under my sweater and that would be better than wearing a dirty shirt, I hesitated for a long eventually I agreed to wear it, we had really good time at her sisters though I did feel embarrassed about my feelings in being dressed almost completely in female clothes realising at that moment that the only male items of clothing I was still wearing were my shoes and sweater.

It was dark and cold when we came to leave, Karen (Samantha's sister), lent both of us coats, mine was a quilted knee length one, I struggled with the unfamiliarity of doing the buttons from the 'feminine' side, Samantha was by this time putting on beautiful large silk scarf as a 'Kelly' style headscarf, the black silk gleaming in the light. Karen went off and returning an identical scarf and handed it to me suggesting that I must wear it as it was going to be cold on the walk, she insisted and helped me with the double knot at the nape of my neck making sure she smoothed the silk over my head, I'm certain that she noticed me shiver slightly as she did so, catching a glimpse of myself in the hall mirror, I was quite shocked just how feminine I looked.

Chapter two

I'd had a lazy day on Sunday and found it amazing that I'd been here for nearly a week, on Monday the gale force winds still blew but were due to drop later in the week which at last would give me an opportunity to leave the island, I had real concerns as to what was happening to me, somehow the process of feminisation had made me more compliant, I found myself asking for help with my corset, by now I was used to dealing with my stockings but the new corset had eight suspenders meaning I had to spend more time clipping them to my stockings. Samantha tightened my corset more this morning giving me a narrower waist and enhancing my 'breasts' more.

I was eager to hide my new 'feminine' assets and was in a hurry to put on the blouse Samantha handed me, it was a rich dark blue satin one which was satin lined, the cool material against my skin felt amazing, the long very full sleeves were gathered at the wrists with three button cuffs, the tiny pearl buttons were fiddly to do up and I had to ask for help with them. As I was working at in the house all day Samantha persuaded me to leave off my sweater, this of course showed off my blouse to full effect, unbeknown to me she couldn't wait to complete my feminisation and had set herself a target to have me in a skirt by the end of the week.

In the afternoon Karen called and picked up my male clothes, she had a washer drier and had offered to wash them ready for my departure later in the week, she even took my suede shoes to clean off the scuffs I had collected on them, I was so grateful to her

On Tuesday morning I got up and took a shower, Samantha had provided me with a black silk dressing gown to wear between the bathroom and the bedroom, back at my room I found my clothes laid out for me, the only thing different was the blouse which was now an Ivory one in heavy satin, it had long sleeves and a high collar, more importantly it was back fastened, I struggled with the buttons at the back and had to ask Samantha to help me, I heard a faint click as she fastened the top button of the collar, there was no way that this blouse could be seen as anything but totally feminine, I tolerated this as I knew that tomorrow I'd be able to leave all this behind me when I left the island

We worked through the morning, at lunchtime the doorbell rang, I heard Karen's voice, I rushed to put my sweater on to hide my blouse, then realised that she'd had taken it yesterday as part of the washing, I then went to find one of the slightly less feminine blouses, when I tried to change I found a small padlock had replaced the top button at the back of my neck, I was trapped and could hardly raise the issue of the lock with Karen present, I had no option but to join them in the living room.

When I got there I was amazed to find that both of them were dressed identically to me apart from the knee length high heeled boots they were wearing.

Karen said how lovely I looked and I was fairly certain that she referred to me as 'she', I wanted things to stop but could hardly raise the subject of my locked blouse with Samantha with Karen present, Karen realising she still had my shoes found a pair of boots similar to hers and somehow persuaded me to wear them, at least thank goodness they had flat heels!

Before it got dark Karen suggested we all went for a walk, she handed me a jacket saying that we had to get going before the light went, I put it on and was hustled out the door, it was only once I was outside that I realised that it didn't conceal my blouse, was buttoned on the wrong side and was cut in a tailored way to accentuate my corseted waist.

Once outside my discomfiture was made worse when Karen and Samantha both put on Kelly style headscarves and insisted I did the same, I caught sight of my refection in the French windows realising that I was not wearing a single piece of male clothing, I just wanted to hide but at the time was disturbed as to just how I felt surrounded by all of the sensual materials. Both Karen and Samantha were so happy, little did I realise that it was due to the fact they had taken me even further down the road of femininity.

When I went up to my room at the end of the evening Karen followed me up the stairs, she helped me unlace my corset before handing me a full length lace trimmed black silk nightdress with a matching gown, she explained that she needed me to wear the nightdress as I had a habit of getting up during the night and wandering down to the kitchen with little on, that had been ok when there were only two people in the house but now she was staying over it wouldn't be acceptable, I was to sleep in the nightdress so that I wouldn't forget to put it on if I got up, I would simply slip the gown over it if I needed to leave my room, I was too tired to argue, later she told me that she loved the thought as she closed the door of my room that there would be no escape from the touch of silk for me, I would now have spent a 24 hour period largely en femme. On my part I was incredibly aroused and found myself masturbating, I really was puzzled by what had happened to me

Wednesday morning, at last the day had arrived, the weather had calmed, the boat was due later in the morning and Karen had gone home to get my clean male clothing, I'd decided that once back on the mainland I'd resign my position, it was all getting too strange for me as I had very mixed emotions as to what had been happening!

We all had breakfast together in our nightdresses, the girls insisting that I joined them, Karen then went back to her cottage to collect my male attire and we started packing the items for our meetings.

Karen returned empty handed, she'd slipped on the cliff path and the bag containing all of my clean male clothes had slipped out of her grasp and fallen down a hundred foot drop, there was no chance of recovering them, Karen was devastated and I was distraught, I just wanted to leave.

Samantha took immediate charge, We had to visit two clients on the mainland, these meetings were as soon as our flight landed, once we had done that we could go shopping for some new clothing for me (this was of course a blatant lie on her part, the shopping would be of an entirely different nature!), she then laid out my clothing for the trip, it consisted of the feminine jacket, my normal corset, stockings and knickers, the ivory satin blouse, a satin gaff, a pair of soft woollen trousers with a side zip and a pair of low heeled loafer style shoes, she explained the point of the gaff, the trousers were tight fitting and because of the side zip would make my male parts very obvious, the gaff would hide these, I was so eager to escape from my captivity in silk and satin that I agreed to wear all of the clothes..

As I walked downstairs Karen commented as to how she could see that the heels made me walk differently, she handed me my 'briefcase' which was in fact a large handbag with a silk scarf tied to the strap. Once again I heard her make an aside to Samantha as to how lovely 'she' looks, all I actually wanted at this point was to get to the clothes shop and to be able to change out of these ultra-feminine clothes I was wearing, I would have made a bolt for as soon as we landed but for the fact that Karen had my wallet in her handbag, just a little longer I thought and I would be free.

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13 Comments
cdCindy1cdCindy1over 5 years ago
good start

This is a fantasy of mine - to be feminized by 2 dominant women. I can't wait to read the next chapters.

AnonymousAnonymousalmost 7 years ago
I so identify with this (wo)man

My feminization began in similar fashion. Identifying initially as a gay male in my teens and twenties when in a railway station toilet, a well known beat for commuters, I was handed a small bundle Under the partion wall by a man and told to put them on before we engaged in any sexual activity. I was so horny that I didn't argue I just changed into what turned out to be a pair of obviously pre worn panties and and stockings the man then had sex with me and as soon as he had cum he just zipped up and left me there in the panties an hose. (My own top clothes and underpants being in a carrier bag at my feet). I kept those panties and stockings and wore them every time I wanted to masterbate. Today my name is Linda Crystal, my fem wardrobe is now extensive and I Am the collared Sissy of my Topman Allholes and serve him and his invited guests as their Sissy slut and love it.

AnonymousAnonymousover 7 years ago

Great beginning. xxxx

AnonymousAnonymousabout 8 years ago
Well written story but has a few holes in it.

I would think that most guys would put their foot down and stop wearing the woman's clothes, except the ones that were really needed, no matter what the two women said and did. He could have hand washed his clothes every night and dried them for the next day to wear. And what man will give up his wallet to a woman to hold that is not his wife. Men do not leave home without their wallet in their pocket. And the job does seem a little suspicious and phony to be out on an island with little to no way off it and no luggage to arrive in a timely fashion.

AnonymousAnonymousover 8 years ago
Great Start

OMGosh....an eight garter strap corset is simply delicious....has me so very aroused in my nylon bikini panties, and thigh high stockings....and pretty, pink, lacy underwire push-up bra..... Mmmm!!! Thanks for a very erotic story.

SissyCrissy..................xoxoxo

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