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The Feminization of Michael - Chapter 1

The Feminization of Michael.

Chapter 1

How I had found myself in this predicament Ill never fully understand.

Ok I guess it was my own fault but why I didn’t kick against it when I could Ill never know.

I had been involved in a sordid night of drink drugs and sex with a young transsexual hooker! Including her/him putting a bra and panties on me! I didn’t know any of this until my wife, Sue, confronted me with the brown envelope with pictures and a blackmail note.

I had been caught before having sex outside the relationship, but this must have been the last straw for her.

She was now blackmailing me!

She had set up an elaborate sequence of emails that could be triggered at any time sending these images to my family, boss, the guys at the Club, and other important people, I wouldn’t want them  to see me dressed in a pink bra and knickers and in the arms of a transsexual! In particular I was the sole beneficiary of my very rich Aunts will. She was a puritan and had already cut my sister out of the will due to her sexual promiscuity. I wouldn’t risk my inheritance under any cost.

She started setting down , what seemed an unusual at first, set of rules. I would have to comply!

Whilst I was at work she was a busy girl!  I returned home that evening and she told me she had moved me into the spare room, and that she had bought me some new things. Strange I thought, I thought she wanted to punish me!

I went to the room with her in tow.  The wardrobe had a few new grey and black suits hanging in it which looked ok and a rack of white, blue and striped shirts .

“Where are my other suits Hun,” I said.

“I burnt them,” she said. I didn’t get it? She had then bought new ones?

“Go and have a shower,” she instructed.

I went and did as I was told.

She popped her head around the door and produced a can of some foam. I want you to apply this and remove all your body hair Mike.”

“What!”  I said , “why?”

“Because I say!” She snapped.

This was madness but I couldn’t risk her circulating those pics! So I dutifully did it.

I looked weird afterwards.

It was then that it all fell into place. She had opened the draw in the bedroom that was full of flimsy lycra white, pink and black  things! She had also removed the clothes I had taken off! The last of my old clothes I suspected. But there were at least new business suits and shirts in the wardrobe .

She had laid out a white lace nightdress on the bed also! Ok so she wanted to humiliate me in the house and make me wear bras again. I could manage that.

“Put this bra on honey for me, and then you can slip your pretty nightie on dear” she smirked.

“You really are sick aren’t you, but I‘m not bothered ,” I said.

“Oh you will be,” she said under her breath as she left the room.

I slid between the pink sheets and fell asleep in my night dress!

I slept heavily and was woken early by Sue. “Come on sweetness time to get up you have work.”

I stumbled out of bed in the night dress and bra. What the hell I thought, then I remembered! Whatever.

“As you don’t have any male underwear anymore honey you’ll wear a bra and lace short knickers today.” She snapped.

“No fucking way!” I shouted.

“You will honey or…,” she threatened.

I thought at least I can keep them covered, The bra?  I would have to keep my jacket on.

I slipped on a plain white unpadded bra thankfully it didn’t change my shape! She had supplied me thankfully with what I guessed were plain sports type bras, although there was a little satin bow on the front! The knickers were full on elasticated lace however and they seemed to constrict tightly my penis and scrotum.

“That’s better Mike, I may start to prefer you like this,” she chuckled.  I glared at her.

“Your new shirts and suits are hanging up, go and get dressed now. Oh there’s also some new shoes in there for you.” She left leaving me to get changed.


The bra was clearly going to be visible through the shirt but I would keep my jacket on and buttoned up. I picked the white cotton shirt out. As I put it on it seemed tight. wrong size I thought. As I pulled it together to button it up it clung tightly to my waist, it was a very fitted shirt I thought. I then realised I couldn’t button it up! The buttons were on the wrong side! Whilst it had a collar in a shirt style, and I spotted some new slim ties in the wardrobe, it was in fact a woman’s blouse!

As I turned to go and object, Sue was in the doorway and barked “get dressed!”

Shit I thought this is going to be difficult!  The tie will cover the buttons and with the jacket on I could hide it.

The ties all had some pink in them! I put a grey and pink striped one on. It was really thin like a bootlace tie! I was going to be the laughing stock in the office. It was to get worse.

I picked a plain black suit out. However when I started to put the trouser on I realised there was no fly in them! I pulled them up and they seemed like hipsters! Oh my god I thought they are women’s trousers! Sue made me zip the side zip up and button up the top. There was a double slim black belt with two chrome slim buckles fastening. They were quite full and baggy as well! The combined effect of the tight lace shorts and flat fronted tight hipster trousers flattened my manhood completely. I could see Sue was pleased!

“I cant go in like this honey ! Come on!” I pleaded.

“You have no choice, or I have no choice other than to circulate that information!” She stated.

The suit jacket was again fitted and clearly a woman’s cut. The problem was when it was done up with the single button fastening it pinched in the waist, with a flaring of the bottom of the jacket , which also seemed shorter than a mans jacket. It also seemed to have extra space at the front with darting obviously tailored to fit a bosom! I would have to do it up to cover the bra though!

Then the socks! Which were sheer black stocking material, with little black spots called Pop Sox!

The shoes were clearly women’s loafers. They were at least flat but had a flamboyant silver buckle on the front.

I went down stairs.

Sue chuckled, “well this may make you keep your dick in your…knickers.” She laughed some more.

“This is crazy, Ill get the sack!” I replied.

Sue would normally drop me off , as she did that morning. I walked from the car into reception feeling totally stupid. There were a few giggle and hushed comments but I went to my desk in the open plan office and got on with my work.

A couple of the guys took the  piss. “What’s with your new style Mike?” I dismissed their comments just shrugging.

I had a pre-planned meeting with my boss, who clearly looked at my new appearance and looked a bit confused but said nothing.

The first day went on as normal other than that. And I continued for the first month like this. I think they got used to it at work. But I still got sniggers constantly, but it was never directly discussed.

At weekends Sue made me change into significantly more feminine clothes. The bras were lightly padded and I wore lace edged vest tops and fitted cardigans. At least I only had jeans, albeit women’s jeans, and all my shoes were “dolly” shoes, at least without a heel!

Those were the only clothes I now had! I generally tried to stay in, but I was forced to go to the shops often. She had bought me a knee length women’s coat that I did up tightly and tried to hide in. I also put on a beanie hat and shades so I wasn’t recognised. I got the kids taking the piss a lot.

I used to get my hair cut monthly but she stopped this. Thankfully it was quite short, but it seemed to grow thickly and quickly now it wasn’t being cut regularly.

I returned from the shops one day to find she had replenished my wardrobe with new clothes! I saw immediately that they were more female! There were two suits in a burgundy shade one almost a light plum colour! And two paler grey suits, one with a pinkish stripe and one with a pink check. I checked quickly to see they had trousers, and they did!

The shirts were replaced, this time there were various shades of pink, cream and white. They didn’t have collars but open blouse neck lines and they all had some sort of subtle flower or frill detail.

The plain bras had been replaced by lace bras and they were slightly padded like my weekend ones !

“This has got to stop its ridiculous Sue?” I pleaded.

“No Mike it wont stop? You know what will happen if it does?” she snarled.

“I think this is worse to be honest than everyone knowing!” I said.

“Its up to you honey?” She chuckled knowing there was no way I could reveal what had happened.

At least Sue continued making me my food and drinks. In fact after dinner that night, me dressed in my bra and cardigan as usual!, I virtually fell asleep at the table!

I woke up the next  morning dreading the week ahead  and going into work in my new clothes.

Sue always insisted on me shaving very closely all over in the morning and in the evening, so I went to the bathroom and looked in the mirror. I nearly fainted!

My eyebrows had been plucked into a fine, high arched line, and my lips seemed fuller and plumper. As well as this I had a gold stud earring in each ear! My hair which had grown shaggy and down to my collar, seemed to have blonde streaks in it and had been styled into a short bob style!

“Sue!” I bellowed, “what the fucks going on!”

“Do you not like it dear? I drugged you so you would sleep well and then  plucked your brows and injected some collagen into those lips, you have a lovely pout now and look quite pretty.” she replied.

“what the hell can I do now?” I cried.

“Stick with the programme Mike, or else!”  She chuckled .“Oh and by the way you will wear that new pink bra today, choose your own suit and blouse dear. I also got you new dolly shoes for work now.” she said as she left the room.

I was flabbergasted, angry, upset and screwed!

I put the pink lace bra on, it was padded and clearly would show through the shirt, or blouse! I pulled on a tight pair of matching lace shorts that kept my genitalia flattened, and noticed that the Pop Sox had been replaced with sheer hold up tights that had elaborate lace tops.

Oh my god, I thought as I pulled them on. The best, or plainest blouse I found was pink to try and disguise the bra, but it had a small lace trim down the front around the buttons. The buttons finished short of the neck, revealing a lot of the top of my hairless chest. The collar was cut to be positioned over the jacket. It was fitted and had a ruched design around the bust area.

I selected the grey and pink striped suit. It had low slung trousers again, tight around the top and flaring out in the leg. The zip for these was again at the side. The jacket seemed more tailored than the last ones and had two buttons at the front and a wide collar.  I noticed the new shoes! They were flat and in black patent leather, like ballet shoes almost, with a little bow on the front!

I walked to the mirror and felt sick!  I looked like a butch woman! Whilst I was quite slim, I looked like a man in the face, even with the pouty lips and fine eyebrows! Work was going to be hell!

I was dropped in as usual. I sensed Sue enjoying my discomfort as I walked in looking more feminine than the previous month!

I endured a further, more obvious amount of giggles and comments behind my back, but just carried on.

I attended a meeting with my work colleagues and boss. Again my boss stared at me a few time during the meeting but passed no comment.

My boss called me into his office afterwards. “Mike I’ve heard the rumours and obviously your appearance has changed somewhat over the past couple of months. Your wife has already telephoned me to explain the situation.”

I nodded not knowing what to say!

“We have a very open policy here on gender and I want to assure you that we will support you in whatever you want to do.” he said.

“No its not like….,” I started to explain. He cut me short saying that no justification or explanation was needed. I think he wanted me out of the office.

“Oh and I have included you on a course that your wife suggests you are keen to take.”

I left the office angry that Sue had been in  touch with him.

The weeks continued and Sue made me wear the plum coloured suits and each new outfit that was forced on me caused much hilarity at the office.

I wasn’t asked to join the guys down the pub anymore, in fact they gave me a wide birth assuming people would think they were gay if they talked to me. The girls seemed to be sticking up for me against them from what I could make out.

I picked up a rumour that was flying around that I was a transsexual! I just ignored it all and carried on.

I had noticed my hair growing so thick these days and my skin seemed softer but that could have been the creams Sue made me use to remove hair. My nipples also ached a bit, again I thought the new bras might be rubbing them. I had given up football on Sues insistence and noticed that whilst I seemed to be thinner I was developing fat in strange places around my bottom and chest. I almost had the start of man boobs!

After two further  months in  the new business clothes, Sue introduced my new weekend wardrobe! These were accompanied by a list of rules!


1.0 Every Friday you will change from your work clothes into your new weekend clothes.
2.0 You will put on full make up. A new kit is on your dressing table.
3.0 You will find in your draw silicone breast forms that you will use in your bras. You will sleep in your bras and breast forms and wear a night dress.
4.0 You will continue to do my shopping dressed as a woman on Saturday etc.
5.0 You will now do all the ironing and cleaning. I will continue to cook.
6.0 You will adopt the name Michaela whenever you are at home.
Failure to comply with any of the above will result in emails being sent!

I was fuming! But what could I do!

I opened the cupboard and was horrified! Along side my business suits and blouses were lightweight chiffon dresses, skirts and tops. I hurriedly rifled through them but could see no jeans or trousers! On the bottom of the wardrobe were four pairs of women’s high heeled shoes! This was all I would be wearing at weekends!

As Sue applied my first night of make up I looked at her with hatred.

“You will learn how to do this for yourself from now on Michaela.” She stated.

I looked in the mirror once she was finished and was amazed how I was now starting to look like a not so butch woman!

I put on a white bra and inserted the breast forms. Fucking hell I thought I have tits! I stepped into a purple floral tea dress that had buttons all the way up the front and tied it at the back. My fake breasts filled the dress naturally. I felt sick. I slipped on a pair of the 4 inch heeled shoes. They were a deep purple colour with a little buckle on the toe. It was winter so I had to put on one of the cardigans also. These were lightweight and short and when done up emphasized further my feminine look!

I went downstairs and Sue beamed with delight.

“You look lovely Michaela!” she said. I couldn’t speak. “I’m going to throw you in the deep end and ask you to go to do the food shopping for me now dear.”

She had bought me a purple “swing” coat that had four double breasted large buttons on the front, and flared from around my bosom area and finished at my thigh level. She also gave me a large handbag that she put over my shoulder.

“Off you go my honey.” She said tapping my bottom as I left.

I got in my car and sat there in a daze.  I drove to the supermarket hoping no one would recognise the car, or more so me driving it!

I often bumped into work colleagues at the shops. Here I was in full make up, a dress  and heels walking into my local supermarket! My heart was bursting out of my chest!

I grabbed a trolley and clicked into the store. With the heels on I must have been over 6ft and I noticed kids pointing and husbands giving me aggressive looks and laughs.

I was about halfway through when I heard someone shout “Mike!” I turned away trying to ignore it but I heard it again. This time I turned to see two of my old football Mates approaching me with a few packs of beer.

“Mike, is that you?” one said.

“No fucking way man!” the other said. “Yes it is, fucking hell you’re wearing a dress and makeup, your a tranny!” They both burst out laughing.

One of them grabbed my breast, “Its got tits too!” he snarled.

“You fucking sissy faggot!” the other one said. “Wait till the guys hear this,” they left in hysterical laughter.

A few people had overheard and been watching. I carried on feeling sick.

When I got home I didn’t tell Sue what had happened. I guessed she would have found it amusing!

I unbuttoned the coat, hung it up and sat their silently in the kitchen in my dress and cardigan.

I was totally screwed!













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