From Stephen to Stephanie Pt. 04

Story Info
Forced Feminisation increases.
3.3k words
4.29
45.3k
15

Part 4 of the 5 part series

Updated 06/07/2023
Created 12/10/2015
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Chapter one

The morning after the party I answered the phone, it was Emma who had tormented me so much the previous day, she asked to speak to Karen who then told me that Emma wanted her scarf back and wanted me to deliver it to her.

Karen insisted that I go and change into my maids outfit, she surely didn't intend for me to walk to Emma's house dressed like that! I refused point blank to change; I'd had enough and still had a spark of rebellion left in me. This decision would have been more sensible had I not been locked into high heels and was not wearing a short chain between my wrists, for my insolence I received the hardest thrashing I received to date, with tears running down my eyes I surrendered and dressed as directed, Karen used Emma's scarf to gag me as she said that was the most appropriate place for it, she fastened a steel collar around my neck, linked a chain to it and led me to Emma's house, the experience was so humiliating especially as with my wrists restrained I could nothing to keep my skirt from blowing up, I felt totally vulnerable and exposed especially as whilst I being led we met some of the other girls who had been at the party, Karen insisting that we stopped and chatted to each one to make my embarrassment worse.

Emma opened the door as soon as we arrived, she must have been waiting for us, she was dressed from head to toe in black leather, a halter neck top, tight leather trousers tucked into knee length high heeled boots and long leather opera gloves. Karen handed the chain she was leading me with to Emma.

I felt humiliated; I was being handed over to a stranger who I had only had the briefest acquaintance with. Emma smiled, her eyes however remained cold, and I felt a shiver run through me as I was led into the house.

Emma told me that my time with her for the next week would be tough, she believed in discipline and would not tolerate any infractions of her strict rules, I was told that I must only refer to her as 'Mistress' during my stay. Emma asked me the question 'what should you call me?' As I was still tightly gagged I was unable to reply, I grunted through my gag and immediately received a slap across my face, Emma said I was being rebellious, a trait that must be punished.

She dragged me through the house, my wrists were still chained so my resistance was ineffectual, as she opened the door at the end of the corridor my blood ran cold, what I saw in front of me was a fully equipped dungeon, Emma fastened me to a whipping horse, pulled my knickers down and began to beat me on my bare skin with a riding crop, it was harder and more painful than I had ever experienced before, I struggled to get free but the straps holding me down were impossibly tight, there was a mirror above me and I could see red wheals appearing on my skin.

The beating seemed to go on for ever, what made it worse was that it seemed to arouse me, something I found impossible to comprehend; my erection was painfully constrained by its chastity device, at last the blows stopped, Emma stood back breathing heavily before reaching down and unlocking my chastity cage, my erection sprang out as Emma took a step back, I relaxed slightly as she removed my gag. Before I had time to think it was replaced, this time forced tighter between my lips, the effect of this was to increase my state of arousal and also my state of fear.

She then surprisingly apologised for her treatment of me and began to gently stroke the very tip of my erection before asking me again to call her mistress, the tighter gag made speech even more impossible, my muffled speech was not the clear answer she wanted, I felt I was in the hands of a maniac who made the most impossible demands of me

Emma said at this point she would not beat me with the crop again; the marks it was leaving were too much, I thought that my punishment had ended, that certainly was not her intention as she then set about me with a paddle, in her words to show me mercy! By the end of this time she was sweating profusely and I was near to total exhaustion, the beating had now finally stopped, any resistance in me had been extinguished.

Emma at last removed my gag, for a minute I thought she'd put it back but I was at last free from it, she took down her leather trousers and as she approached I could actually smell her juices, she very aroused, she held her cunt against my face holding the back of my head with her hands, I could not pull away from her, it was obvious that she wanted me to orally satisfy her and tired as I was I tried to do so thinking that another beating might come if I failed, luckily I succeeded, I had never been good at oral love with my wife but this situation seemed very different, Emma shuddered to an orgasm and wiped off her juices with the scarf that had gagged me, she then took perverse delight in stuffing that back into my mouth before blindfolding me, I was left helpless with the aroma and taste of her all around me.

Chapter two

My time at Emma's continued, I longed to get back to Samantha and Karen's, and whilst I had to suffer feminisation and bondage there life had been much easier than it was now. My yearning to be away from the island had been replaced with a simple desire to escape from the daily ministrations of Emma

I was locked in a maids outfit virtually every day, Emma had had a second one made for with hidden flaps above my nipples enabling her to attach clamps at will, she had increased twofold the amount of hormones I was taking and this dosage increased further the sensitivity of my nipples with a resultant increase in the pain the clamps caused, it was worse when they were removed and the blood rushed back into them. Emma had removed both the chastity device and the locking gaff from my wardrobe, she had a thing about seeing my erection straining against the satin of my French knickers, she said it gave her an incredible feeling of power knowing that she controlled me totally, she did however take the precaution of putting me into restraints at night, this of course prevented from masturbating in secret.

She would often walk about the house naked apart from high heeled thigh boots and long leather gloves, she said that her idea was to train me as her lesbian lover, to make me her total submissive, her training obviously worked but she still seemed insatiable despite the number of orgasms I was providing her with on a daily basis. Emma also now kept me butt plugged most of the time, gradually increasing the size of them, I still tried mentally to resist the pleasure these gave me but by now the combination of the hormones, the continuous feminisation and submission were slowly overcoming me, I was a very different person the man whose wife had left him at what seemed an age ago

One day and with no warning Emma told me that I could move back to Karen's, I felt a huge release of emotion and didn't even mind the shame of being led across the Island in my maids outfit, Both Karen and Samantha greeted me warmly saying that I looked exhausted and suggested an early night, I didn't even mind them putting me back into chastity, I was just so relieved to leave Emma's

In the morning I was introduced to a hairdresser who they knew, she coloured my by now long hair and cut in a style that was totally feminine before piercing my ears, a few weeks ago I would have protested violently at would only be seen as more permanent feminisation, my relief at my escape from Emma meant that there was no way I would upset Karen and Samantha, they chose my outfit, black satin underwear including a corset, black opaque stockings, a very short leather pencil skirt with a side split that showed off my stocking tops, a black silk halter neck blouse and a pair of knee length high heeled boots. With my new hair style, the changes to my figure that the hormones had started and the joy of being away from Emma I felt so happy and so relaxed, I realised later that this was the first time I relaxed as Stephanie, however that was only to last for a short time.

Chapter three

The doorbell rang and I went to answer it flicking back a stray blonde hair as I did so, my smile froze when I saw Emma framed in the doorway, she stood back to admire me and as Karen came up behind me Emma thanked her profusely for making me look so truly feminine, I turned around and looked at Karen pleading with my eyes and asking her not to send me back to Emma's, Karen just smiled and gently pushed me out of the door closing it behind me, as she did so Emma put her arm around me saying how much she'd missed me, that same cold smile I'd seen before coming over her face, I turned around and tried to push the door open but in a flash Emma had grabbed my wrists and handcuffed me.

We walked slowly back to her house, I for one was in no hurry to get back there! Emma chatted pleasantly until one part of the conversation stunned me. Emma said that she'd met my wife at a trade show the other day, Emma owned several dress shops and was now advising my wife on how to improve her store, she'd actually shown my wife some pictures of me but I had been unrecognisable to her in my new persona. I found myself crying at this point, I just wanted things to go back as they were. Emma continued chatting having dropped this bombshell only to follow it up with the fact she was planning to seduce my wife into a lesbian relationship as soon as possible, my tears flowed, I pleaded with her to leave my wife alone, the only result of that pleading on my part was to find myself gagged once more, Emma laughing as she did so.

We'd arrive back at Emma's house by this time, Emma led me to a tree in the garden and fastened my hands to a chain hanging from a branch, the chain was then pulled up so that I was on tiptoe before Emma added a spreader bar between my legs making me totally immobile, she went into the house and came back with a satin hood, my attempts to stop her pulling this down over my head plunging me into total darkness

I seemed to wait for an age before I heard voices around me, unseen hands started to stroke every part of my body whilst someone pulled down my knickers, I felt a finger coated in lube being pushed inside me, once that was removed it was replaced by a vibrator which was expertly handled, I was kept on the very brink of orgasm for an age and then left tingling with frustration,

After an hour I was lowered to the ground, I was still hooded whilst I was fastened to posts in the ground, my arms above my head, I was lying flat and unable to move a muscle, my hood was roughly pulled off and my gag removed, blinking I saw a group of women around me watching Emma squatting over me, I could see she had no knickers on and was thinking that she would lower herself on to my mouth for oral sex

I was horrified when I saw a stream of warm pee descending on my face, a so called 'golden shower', was there no end to my humiliation, at least I kept my mouth firmly closed and did not have to suffer the indignity of drinking it, I noticed one of the women go off into the into the house and return with something in her hand, Emma had by this time moved away from me, two of the women knelt down and strapped a gag into my mouth, this one was different with a ring at its heart holding my mouth open, the point of this became obvious as another woman peed copiously and directly into my mouth, I had no option but to swallow, It was a new low in my time of being dominated by females

There was a swimming pool in the garden with an outside shower, as much as I could be grateful to my captors I was at least pleased when I was stripped naked and taken to the shower, I felt clean again.

My breast forms had remained adhered, a bra was clipped on to support them, a garter belt and black stockings were the only other two pieces of clothing and my hands were chained to the shower head.

I felt worried as to what was to happen next, the women gathered around me and it was only when they parted that I saw Emma wearing just her thigh boots, what was terrifying was the strap-on she wore, it looked very realistic and pretty large, as she approached one of the other women began to lubricate me, it was like some kind of ritual, I felt the strap-on begin to enter me, I pulled away and screamed for mercy but Emma grabbed me round the waist and pulled me back, the strap-on was now fully inside me and touching my prostate, Emma slid backwards and forwards, I became more and more aroused despite me trying to block out what was happening to me, she moved faster and I felt the pent up orgasm that had been delayed for so long getting closer.

When it came the stream of cum was amazing, I tried to stop myself but I was gasping with joy and emotion, I scarcely noticed one of Emma's friends collecting the cum in a jar. As I came down from my high Emma stood in front of me still naked apart from her boots and holding the glass, I think this belongs to you she said as she took a spoon and scooped out a heaped spoonful, I realised that I was expected to eat this, the thought disgusted me and I shook my head, there was still a very tiny spark of resistance in me. I felt an unseen person hands hold my head in a vice like grip, Emma asked if I wanted another beating, I shook my head, she brought she spoon closer now just touching my lips, she said you have two choices, eat this or I will beat you harder than ever before. I opened my mouth, the taste was salty and pretty awful, I choked a little wanting just to spit it out but knowing what would happen if I did I just swallowed, Emma made me eat the whole contents of the jar, she took a long time to feed it to me which made the experience even more vile, this and the golden shower were the two lowest points on the island, hertotal domination of me had now been achieved.

Chapter four

The next morning Emma said she had some really good news for me, she looked pleased and I was hoping that at last my chance to return to my old life might be just around the corner

The news was not that, it was not even good news. One of the women who had a holiday cottage on the island had seen the pictures and videos that had been made of me. She had asked for an arranged marriage with me into a female led relationship, this news seemed to cement the continuation of my feminisation and probably meant no escape. Emma said I should be pleased, it was an honour to be asked, I felt very differently about this and remained silent. Emma said we should celebrate; her idea of celebration was to tie me down and beat me!

I was determined to make one last attempt to escape, I didn't care that I'd have to do so as Stephanie, I didn't even think how I would deal with things once off the island, I just wanted to be free and certainly did not want to be married to some stranger. I walked across the island to the quay, smiled nicely at the girl who operated the boat and said that I had to collect some paperwork from the main island for Emma. Things went like clockwork, no questions were asked and I settled down in the cabin for the short journey, after a few minutes I realised that the boat was not heading across the channel to the other island but was following the coast of the island I had been living on, I got up to ask what was happening thinking perhaps that it was low tide and we were taking a different route

It was at this point I found the door of the cabin was locked, I pounded on and shouted for help, the girl in the wheelhouse studiously ignored me and concentrated on steering the boat, I suddenly realised where we were, we had arrived at the small quay below Emma's house, I could see Emma and her friends waiting for the boat to dock, I think at that moment I would have had it been possible thrown myself into the sea.

I was bundled unceremoniously out of the boat, my wrists forced into painfully tight handcuffs and a very large ball-gag pushed into my mouth and locked in place, there was a whipping stool already in place on the lawn, I was stripped naked and quickly fastened to this and left wondering what my fate was to be. It became obvious very quickly as both Karen and Emma came back out of the house, both of them naked apart from high heeled thigh boots which gleamed in the sun, they looked incredibly powerful, my concerns when I saw they were both wearing strap ons, these looked very large and the thought of being penetrated by them was terrifying, I wished I had been blindfolded, at least then I would have not had to see them.

I asked to be blindfolded, this request was refused, I tried closing my eyes, however all that did was reward me with a painful slap in the face and a demand from Emma that I keep them open, I did as asked and saw that Emma and her enormous strap on were inches from my face whilst Karen was behind me, Emma came closer, the smell of her arousal combined with the leather of her boots filled my nostrils, I realised that she wanted me to take the strap on into my mouth, I had no option but to comply, I found myself nearly choking on it but was told in no uncertain terms to suck on it, it was a sensation I hated but it somehow aroused me. I then felt Karen's strap on penetrating me from behind, she pushed harder sending waves of pleasure through me, at that moment I felt used like never before, I realised that I had to accept whatever my fate was, and there was no chance of escape.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymousover 6 years ago
I never realised before this story

that I also need total domination by women. I will have to discover how to achieve this. But I think I will start by posting an advert on a local bulletin board.

GirlyclarkGirlyclarkabout 8 years ago
Hotter and harder

I do like the way you have built this story, and now with this latest chapter with the forced punishments and humiliations I find myself more interested and growing harder as I read and even wishing to be forced to change places with Stephanie, hope you continue with this line and more along her humiliations and punishments. Oh, how I would like to be taken too this island of women to be their only object to take out their focused frustrations on. They would not need the open gag for me during their golden release, I can only wish for their nectar.

aboychickaboychickover 8 years ago
Amazing story!

I can't wait for this amazing story to continue. It touches all the buttons. Great writing, too. (Thanks)

rdoolittlerdoolittleover 8 years ago
Hope there is more

Much more! (5)

satinshawnasatinshawnaover 8 years ago
Keep on writing

Keep on writing. I suspect the wife is involved.

Share this Story

Similar Stories

Forced to be Feminine Forced feminisation by a domme.in Transgender & Crossdressers
Humiliated Sissy Husband A wimp of a husband is forced to be a sissy by his wife.in Transgender & Crossdressers
Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
A Husband Named Cathy A husband's dream comes true. He becomes Cathy.in Transgender & Crossdressers
More Stories