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A Nanny Femtastic - Chapter 1


Chapter 1

My story starts during a very bleak time in my life where I was unable to find continuous work of any meaningful type.

I had, I suppose, looking back now, rather stupidly pursued Child and Nursery Care as a further education route. Much to my parents consternation! 

Yes I was the only guy in the college but I thought I would soon move into management positions and my career path would take off! It was actually cool to have so many women around me, and I did have many flings with various girls off my course. However at the end of the course they all moved into work, I didn’t! 

Despite interview after interview I got nothing. It was clearly due to my sex.  I stacked shelves for a while but that didn’t pay properly,  plus I would never develop my career that way and I wanted to prove myself to my condescending father that I had made the right decision.

Anyway I had a period of over 6 months with no work. I was on the breadline.

I was living with two very close girl friends I had become close with on the course. They were like the sisters I never had. 

My name is Tony and my two best friends were Alexandra and  Louise. They were virtually supporting me at this time, so things were getting desperate. I couldn’t go home to my parents cap in hand, and had told them that I had a job working in a children's nursery.

One night we were having a few bottles of wine as was becoming a habit! Lou suggested that if Id been a girl with my qualifications I would be earning good money now.

Alex piped up and suggested I would make a pretty girl. 

I of course told them to stop being stupid,  I was all man!  I wasn’t the tallest or butchest guy out , but I was a guy! I was now 24 years old and had peaked out at only 5ft 8 tall and was toned but slim. Lou and Alex with heels on were taller than me just about.

And that’s when the suggestion was first made that I should pretend to be a girl and I would be able to earn a living. 

Despite my objections and much hilarity they had decided to prove to me I would make a pretty girl. Alex was pretty much a similar height and a size 12, which they assured me was my dress size! 

“Ok., ok go on then,” I said  “just for a laugh.”

“First we need to get all that hair off your body sister,”  Alex giggled.

I laughed and said “be gentle!”  What a laugh I thought!

They took me to the bathroom and I stripped. They had seen me naked before, in fact I had slept with them many times altogether as a threesome. They were bisexual and slept together normally. But as Lesbians there was nothing butch about them. They were both very glamorous girls, and I had spent many nights having sex with both of them, and it was a real treat when they let me!

I wore my dark brown hair long as I was into heavy rock music so it went with my style. It was about shoulder lengthy currently. I usually wore it in a pony tail.

They both got to work smearing this cold cream on me, and after a while with a bit of shaving too I emerged from the shower hairless!  They had even trimmed my pubic hair into a neat little triangle above my penis!

I laughed ,“well done girls! This feels weird!”

“Life's better hairless Tony you’ll see!” Lou giggled. 

“Firstly underwear Tony,” Alex explained.

“Make sure they are sexy, lover,” I laughed out.  And she didn’t disappoint.

She came back from her room with a pink, slightly padded lace bra and knickers. She very quickly placed the thin straps over my shoulders and did up the clasp at the back. She adjusted it and  then filled it with tissues to pad it out. Once I had slipped the knickers on there was much hilarity.

“Sister you have a penis! “Alex joked. She made me tuck it back between my legs held in place be the tight knicker shorts.

I looked in the mirror and laughed . “What an idiot I feel girls!” 

They carried on and went to work on my make up. I was by now getting a bit bored but let them carry on. I looked again in the mirror and was surprised to see me but with this painted face! Sitting there in pink bra and knickers.

I looked something like a girl, but not a lot I thought. However when they undid my pony tail and started curling my hair, things changed!

When they had finished my hair was wavy and set across one eye, and with a hair clasp pulled over one side. I did look like a girl now and I didn’t recognise me! “Wow girls, I'm one of you!“I joked. 

They led me giggling to Alex’s bedroom. She was always fashionably dressed and opened up her wardrobe to expose hundreds of clothes.

“I think Toni, and that’s spelt T, O, N, I now,” she giggled ,“needs a sexy little dress for tonight.”

“Of course darling,” I joked in a girly way. This was fun I thought.

She pulled out a pink chiffon dress that had little fabric covered buttons all the way up the front to a v necked sleeveless top part. There was a frill along the hem and the sleeves. It had a tie at the back .

She made me step into it and put my arms through the arm holes and it hung loose on me. When she did the side zip up it clinged to my slim body and my padded bra started to form a very feminine shape! She then tied up the back which made the feminine shape even more pronounced. This was starting to feel strange. 

“You’re a UK size 7 shoe aren't you young lady?” Alex said. “Fortunately ,so am I!”

She pulled out from the bottom of her wardrobe a pair of pink, strappy sandles, with gold buckles, and I guess about  a 4 inch heel. Once I had put these on they made me have to pull my shoulders back and push my chest out.

I looked in the full length mirror and my legs looked so long and I did look like a woman. I was astounded!

The girls eyed me up and down giggling. “So Toni, you can look like a very passable woman very easily,” Lou stated.

I laughed nervously, “ yes, now get me out of this stuff someone might call in!” I blurted out, not now laughing.

Alex came closer and held my wrists and said seriously to me, “ Toni I am proposing you stay like this now for a while, I have a night dress you can slip into later and come and sleep with me and Lou.” 

“Come on Alex I look stupid,” I said. 

“No you look gorgeous,” Lou chipped in.

Was I turning them on? If so this couldn’t be all bad I thought. “Ok whatever,” I sighed smiling.

We spent the rest of the evening sitting around talking as three women ! Later Alex produced a cream silk night dress that I slipped into and we all slept together. I felt very turned on by the silk material I was wrapped in, and must have had better sex than I can remember.

Through the following weeks this became a regular Friday night thing, which I sort of grudgingly agreed to, dressing me differently each time and teaching me how to apply the make up. They seemed to like it and the sex was great so why not.

After three or four weeks Lou came home with some B cup breast forms for me, which I laughed about, but when slipped inside the bra, felt so much more realistic and seemed to move like a real breast! 

About this time they also talked me into plucking my eyebrows and they formed them into a high arched shape! I regretted this, but I was housebound pretty much and thought they would grow before I saw my parents next.

They seemed to be enjoying feminising me, and we got on better than we ever had.

They encouraged me to grow my fingernails longer and we painted each others toes and nails regularly whilst watching TV giggling. 

After the sex with them I always removed all traces of my new feminine side! Secretly to myself however I quite enjoyed the dressing. I think they realised this as I took more and more interest in talking about fashion and make up.

Alex and Lou were out working all day so I had now started secretly going to Alex's room in the day and trying on various dresses and outfits.  She had so much I was mesmerised.

I also started trying out her more every day clothes, like denim mini skirts, clingy vest tops and cardigans. Also some of her formal business type skirt suits and blouses, and I started to spend longer and longer pottering about the house in these, more everyday clothes, like any girl would!

I think they suspected but never challenged me. Things moved on a pace when Lou came back one night to suggest we should all go out to a gay/tranny bar! I stated “No Way,” but I was easily persuaded.

I was intrigued. Was I really passable as they said? I thought I was in the mirror but to actually go out! I spent longer than them getting ready that night. 

I wore a tight fitting black mini dress, with a black crochet shrug,  that Alex leant me, along with some black very high platform sandles. The girls were just as glammed up as me, and as we climbed into the taxi I didn’t feel at all self conscious.

The night was a total blast and I had a great time as we all did. No one blinked an eye and I thought they must assume we were just three genetic girls having a laugh!

We returned home to bed, all changed into lingerie and slept together.

The next morning, Saturday,  Lou suggested I get showered and dressed as a girl for the day.

I didn’t object! And had almost wanted her to suggest this.

I borrowed a short denim skirt, that I had already tried before secretly, some  flat brown knee length boots that zipped up, and a fairly see through lace top. 

I wore a white lace bra and knickers under this. I wore my hair up in a high pony tail, not like my old boy pony tail. And I combed my now long fringe down to just above my brows.

The girls welcomed me downstairs and didn’t blink an eye carrying on as normal! I had the best day I had had in a long time.

We carried on spending most weekends like this and glamming up regularly to go to the gay bars.

Most days I got dressed in the morning as a girl and had dinner waiting for Alex and Lou dressed as a girl into the evening.

I had even let in the meter reader and taken postal deliveries as a girl with them not even blinking an eye, and calling me Miss !

I just couldn’t work out what was happening. I loved dressing in girl clothes, I felt relaxed and unstressed.

But where was this leading? How could this work?







This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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