This is the story of how I came to be Annabel.

The First Evening (Part 1 – synopsis)

Ian Naismith went on a tour to the South West of England with his field hockey club. At the farewell dinner dance on the last evening, he met Helen. He went back to her house and she encouraged him to live out his fantasy of being a lady's maid.

 

Annabel's Story

by Annabel Naismith

 

The First Day (Part 2)

"Good morning, Annabel," Helen entered the room breezily. "It's eight o'clock and we have a lot to do today."

"Hi Helen." I turned over in bed and remembered I was wearing a slinky black nightdress Helen had provided the previous evening.

"You need a shower and then we must go to your hotel so you can collect your things. I'll drive you over."

How she could think of things like this at eight o'clock on a Sunday morning, when I'm hung over, I thought. However, I got up slowly and carefully and shambled into the bathroom. The shower woke me up and Helen brought my male clothes from the previous evening.

After a quick breakfast of coffee and cereal, Helen drove the short distance to the hotel. I went to my room and packed quickly, hoping to get checked out before I met any of the tour party. Fortunately it was Sunday and the hotel did not serve breakfast until nine o'clock, so I was able to check out of the hotel and go to my car without being seen. Helen was waiting and I followed her car back to her house to drop off my car.

"Right Ian," said Helen. "We need to go shopping to get you a lot of things. You will need make-up and clothes. I need to measure you. Let me get a tape-measure"

The matter-of-fact way she did everything gave me no choice but to go along with everything she said.

She slipped the tape-measure behind my back to measure my waist.

"Hmm. 33 inches, we may be able to reduce that to 30, so you can fit in size 16. You don't want to be a size 18 because your hips are too small and anyway, clothes for size 18 and bigger are just horrible."

She lifted the tape measure to my chest.

"36 inches, that'll be OK. You can be a 38B once you have boobs."

She made a note of the measurements and put them in her bag.

"Put these on, you'll need them when you get your shoes," said Helen giving a pair of black ladies knee high stockings.

I had serious doubts about trying women's shoes on in a busy mall shop. However, I took my socks off and put the stockings on. They were quite opaque and would easily pass for male socks unless you looked very closely.

Then we got into Helen's car and drove to the shopping mall. Helen passed me her handbag and, with broad grin and a mischievous twinkle in her eye, told me to keep it on my lap "for a bit of practice". We reached the shopping mall just as it was opening.

The first stop was to a specialist lingerie shop. Helen approached the assistant.

"Hello, we need a corset for this young man, lace-up preferably."

I thought I was going to die of embarrassment. I was surprised at how utterly unfazed the assistant was; I guessed this was an everyday occurrence in her shop.

"Of course madam. What size is the young gentleman?"

His waist is 33 inches at the moment but I would like to train him to 28. Would that be possible?" asked Helen.

"Oh certainly, given time and a careful diet," replied the assistant.

She produced several garments. Helen selected two particularly feminine items, the first was a pastel pink and the second was black with red trim. Both had garter belts and laced up at the back.

"Now he is going to need panties, bras and stockings. He is a 38 bust and I thought his breasts should be B cup." Again Helen managed to cause me the maximum humiliation.

Just when I thought things couldn't get any worse, two teenage girls came into the shop and started looking around idly. They glanced over at us as Helen's selections were assembled on the counter and started wandering towards us.

"Oh, and he'll need slips and a petticoat."

This was too much for the girls, who giggled loudly.

"Can I help you," asked the assistant sternly.

"We're just looking," said one of the girls.

The assistant glared at them and they went towards the front of the shop, still giggling quietly.

"I'm sorry about that," said the assistant.

"Oh that's all right, no harm done," said Helen. Maybe not to Helen but I was just squirming with embarrassment.

"What length of slip do you require?" asked the assistant.

"Ian, are you happy to wear your skirts above the knee?" asked Helen.

"Yes," I mumbled.

"Ok. Try this one for length." With that Helen took a short waist slip from the counter and held it in front of my waist.

"Hold that," Helen instructed and stepped back so she and the assistant could check the length of the slip. At the front of the shop the two girls looked over at me holding the slip in front of me and burst into another fit of giggles.

Thankfully, that was the last of my torture in the lingerie shop. Helen paid for all the clothes, including several pairs of stockings.

The next shop, to my horror, was a shoe shop. We went into the shop and again Helen went straight up to an assistant.

"Hello, we need a pair of size 8 ladies black court shoes for this young man. Something with a two inch heel would be ideal."

"Certainly madam," said the assistant, again unfazed by the request. I was sure that if I had asked to buy a pair of ladies shoes for myself, the police would have been called and I would have been arrested. But Helen always managed to be so practical and assertive in a pleasant way that no-one thought there would be anything unusual in her requests.

The assistant returned to the busy shop-floor with several boxes. Helen and I looked at the shoes.

"I think something plain would be best," said Helen. "Do you like the patent leather?"

"Yes," I said quietly, hoping not to draw attention to myself.

"Well, try them on then," said Helen.

"Oh God," I thought. Can this get any worse? Surely I won't have to mince up and down in a crowded shop dressed as a man and wearing patent leather high heels.

I sat on a chair, slipped of my shoes and tried on the first shoe. It was a little tight but not too bad, then I tried on the other shoe, which also was a little tight. I felt that several people were looking at me and was dreading being asked to walk in the heels.

"How do they feel?" asked Helen.

"Fine," I replied honestly

"Are you sure they will be OK?" asked Helen.

"Oh, yes. They're very nice," I replied.

"We'll take them," said Helen to the assistant and I breathed a major sigh of relief as I slipped off the heels and put my man's shoes back on.

Then we went to a major department store, to get skirts and blouses.

"I think you will get on better with skirts and blouses for work rather than a maid's dress to start with. You will need a couple of black skirts and several plain white blouses to start with." said Helen as we entered the store.

I was in a daze, how could Helen remember all the things I would need. She selected several blouses in white cotton with short sleeves and two black skirts in size 16 with a length of 15 inches. Fortunately, I was spared the embarrassment of having to hold the skirts up in front of me to check the length. She also bought a white apron, some girls' pyjamas and another nightdress, the same length as the one I had one the previous night and in a pale pink with white lace.

"Now we have the clothes, we need to sort out the cosmetics," said Helen decisively.

The drugstore supermarket was quite full; there were groups of teenage girls chattering about nail varnish colours, hair colours and so on. Married couples were also meandering to and fro among the aisles; the wives were always the ones doing the purchases and the husbands appeared to be wishing they were somewhere else. Seeing the husbands reminded me of my new role and I made an effort to take notice of the purchases that Helen was selecting for me. There was moisturiser, foundation, blusher, lipstick, eye shadow, mascara, nail varnish, emery boards, eye-brow pluckers, shampoo and hair conditioner, shower gel, bubble bath and de-odorant, and finally 3 bottles of depilatory cream.

Once again, Helen paid for all the items and we carried all the items to the car.

"Let's have lunch," said Helen as we left the mall. "I know a nice Italian restaurant but remember, we need to get your waist to 28 inches, so no massive steak dinners."

Lunch was delicious; I had the same as Helen, chicken in a creamy mushroom sauce and side salad.

After lunch, we had one more shop to visit before returning to Helen's home. A sex shop.

I had never been in one before and had imagined they would be dark, seedy places selling sex magazines and dildos. However, this shop was bright and welcoming and there were a few couples in there looking at the displays.

Helen, as usual, took command of the situation.

She picked a basket and began to put the most unlikely items in it. A butt plug (what was that going to be used for, I wondered), a small vibrator and a larger one, a weird sort of harness thing which I couldn't identify, some lubricating jelly and a pair of leather cuffs joined together by a chain.

Then she walked over to the rack where a variety of uniforms was hanging up. There were uniforms for school girls, cheer leaders, nurses, various items in rubber and leather and a number of maid's dresses of different designs.

"We need a dress you will be comfortable in," she announced to everyone in the shop. People looked round but no-one seemed to mind. After my experience of the morning, I was becoming used to being humiliated like this in front of shoppers. Besides, they must have guilty secrets themselves, or they wouldn't be in a shop like this, I reasoned.

I looked at a black satin dress with a short skirt and white satin frilly petticoats.

"That looks nice," I said

Helen removed it from the rack and held it up against me. Yet again, I had the humiliation of being shown up as a transvestite in front of a shop full of people.

"It's a bit short," said Helen "let's go over to the mirror, and then you can see what you think."

I was paraded 15 feet across the shop floor carrying the maid's dress in front of me. I held up the dress to my shoulders and looked in the mirror. I could see the dress of my dreams, my blushing red face and several other shoppers looking at me.

"It seems OK," I said, as the skirt seemed to reach to about 12 inches above me knee and 4 or 5 inches below where I guessed my stocking tops would be.

"Well it's your choice but the skirt will be higher when you are wearing the petticoats. And I won't have my maid flashing her panties when she's serving tea to my guests." This was audible to several of the other shoppers.

Still, Helen put the dress in the basket.

"And the last thing we will need is some shoes for your training," Helen announced. More shoes, I wondered.

Helen led the way to the section of the shop where there were a variety of shoes, all of which seemed to have impossibly high heels.

"These are the ones," said Helen picking up a pair of shoes with 6 inch heels and a strap around the ankles with a tiny padlock attached to each strap.

"Try these on," said Helen

I sat down and placed my feet in each of the shoes. My ankle joints were fully extended. I didn't think I would be able to stand, never mind walk in these.

Helen bent down and did up the straps around my ankles.

"Perfect," she said, "come on, we'll take all these and pay for them."

I struggled to undo the straps and followed Helen to the queue at the till.

"When we get home," Helen informed the queue, "we can start your training properly.

While Helen drove back to the house, I began to wonder what I had let myself in for and if I would be imprisoned against my will. On the other hand, I reasoned, I was much stronger than Helen and could easily escape. Besides, I was living out my fantasy and I might never have an opportunity like this again. And Helen did seem very pleasant, despite being very direct and assertive.

In a few minutes, the car pulled into Helen's drive and I carried all the shopping into the house.

"Right Annabel," said Helen, "Put your new clothes away in the closet in your room and I will decide which clothes you are going to wear. Then go into the bathroom and let me know when you are ready for me."

I carefully unwrapped all the clothes and hung the blouses, skirts and dress in the closet before putting the underwear and nightwear into drawers.

I went into the bathroom and called for Helen.

Helen came into the bathroom carrying the depilatory cream, shower gel, shampoo and conditioner that we had bought earlier.

"Right, get undressed." She ordered.

I did as I was told and stood, rather nervously as she applied the depilatory cream to my face, body arms and legs.

"Wait for 10 minutes, then get in the shower and wash off the cream. It may sting a bit but don't worry, it's perfectly safe. We girls have to suffer to look nice, you know.

"Now while you are here Annabel, I will take all your man clothes. You won't be wearing them again unless I say you can wear them." With that Helen picked up my clothes and left the bathroom.

I checked the time. 10 minutes can be an age when you are just standing around watching the seconds tick by. Eventually 10 minutes passed and I got into the shower. To my horror all the hair on my arms legs and body washed away into the bath. "Oh my god, she really is going to turn me into a woman," I thought. Then I reflected, if I am going to be a maid, the least I can do is be the prettiest maid I can be. And Helen has gone to a lot of trouble and spent hundreds of pounds on getting me some lovely clothes, why not go with the flow and enjoy it.

I finished the shower and started to rub myself down with a towel. My skin felt so soft without the hair. Then I looked at the bath. "Oh my god," I thought, there was a bird's nest of hair in the plug hole, not to mention stray hairs on the side of the bath and on the tiles around the bath.

I could not see anything to clean the bath with and was just starting to panic then I thought, why not just be direct and honest. After all, Helen herself had told me I was a trainee maid and she wanted to train me, why not just ask her how she would like me to clean the bath.

"Helen," I called, "the bath is a bit of a mess. Could you show me where the cleaning things are, please."

Helen smiled as she came through the door. "I have to agree with you but let's get you into your working clothes before you start work."

While I had been in the shower, Helen had been in my room and had arranged the clothes I was to wear. The pink corset, a bra, panties, slip and stockings were carefully laid out on the bed and a blouse and skirt were hanging on the handle of the closet door.

"I'll need to help you into the corset. It's very difficult to lace yourself into one without help." Helen picked up the corset and slipped it around my front then started to lace it up, loosely at first then she pulled tighter.

"Breathe in," she said. I pulled in my stomach muscles as far as I could and I felt Helen's knee in the small of my back as she pulled the laces tight.

"That should be OK to start with," she said. I was having difficulty breathing and could only draw in shallow breaths.

"Good," said Helen, "now put on your bra and panties and I'll show you how to do your hair, nails and make up".

I put on the bra as I had the previous evening, by fastening it round my waist then sliding it up and putting my arms through the arm holes. Helen put a pair of panties into each cup and adjusted the straps. I put on the panties and followed her over to the vanity.

"The secret with make-up is not to overdo it, or you'll look like a slut," said Helen, "unless, of course you're that sort of girl," she added with a grin.

"I don't know yet," I replied cheekily, "I might be, it depends on my training."

Helen looked at me meaningfully and I was sure I could sense her plotting a different additional line of training to what she had already planned.

Helen blow-dried my hair and the she quickly and expertly applied foundation, blusher, eye-shadow, mascara and lipstick and I was astonished at how feminine my face had become.

Helen looked critically at me.

"Not bad, but the hair is not right yet," she observed, "Don't worry, my hairdresser is coming on Tuesday evening and I am sure she will be able to do something with it." My hair was not too long and a honey blonde colour.

"OK, now for your nails. Take the emery board and hold you hands out with fingers away from you and start to shape a point in the middle. Always work towards the middle." I started to file as she told me.

"Good, but be gentle, we need them to grow out to be feminine." After I had filed each nail a little, I sat back and looked at my hands. It was hard to tell the difference from before.

"Right, now for the nail varnish." She opened the bottle of scarlet nail varnish and handed it to me. "Off you go, use long, gentle strokes and then you will have to wait for it to dry before you go to work. And don't forget to paint your toe-nails".

Painting toe-nails is not easy when wearing a corset, I discovered. But I was able to lift my foot up so my heel was on the front of the chair and reach over to paint them.

While we were waiting for the nail varnish to dry, Helen told me where she kept the cleaning things and the hand washing powder. I was told that I was not allowed to use the washing machine until I had been shown how to use it. She also told me that if the telephone rang the answering machine would take the call.

Eventually the nail varnish dried.

"Now put on your stockings carefully," said Helen. I carefully sat on the edge of the bed and put my thumbs to the toe of the stocking and gently caressed it up my newly smooth leg, then repeated with the other leg. Carefully, I fastened the garters on the corset to the stockings. Next, I put on my blouse, skirt and the patent leather court shoes. With the waist reduction from the corset, I was able to do the skirt up fully and fasten the button at the back.

Helen stood next to me as I looked at myself in the mirror.

"What do you think?" she asked, "I think you make a passable girl and once your hair is sorted out, no-one would know unless you told them. We'll have to do something about that though," she said giving the slight bulge in the front of my skirt a friendly pat.

"Right, now would clean the bath, please Annabel, and then there is the washing. When you have finished that, I would like you to join me in the living room".

I cleaned the bathroom, following Helen's directions and washed the items that needed washing. These include some really pretty, lacy underwear and the dress Helen had worn the previous evening. The dress had been severely stained as both Helen and I had cum onto it. It took several washes and rinses before I thought it was properly clean. I carefully squeezed out most of the water and carefully hung it flat on the rack over the bath.

After 20 minutes or so, I joined Helen in the living room.

"Annabel," said Helen seriously, "I have made a considerable investment in you today and I need to be certain that you will run off. With this in mind, while you are in the house I will lock you in the training shoes, before I leave each morning and unlock you when I return.

"Now, I want you to have your first lesson in walking like a girl. Change into these shoes please." I slipped off the court shoes and put on the 6 inch heels, fastening the straps around my ankles. I stood up carefully; it was difficult to balance on such high heels.

"Good, now walk to the end of the room and back". I tottered slowly using tiny steps as this was all the heels would allow me to take.

"When you walk in heels, always remember to lift your knees and plant your heel in front of your middle and with your foot pointing slightly outwards, that will give you a feminine walk and a sexy wiggle. And hold your elbows close to your ribs with your palms towards the front. Men always walk like gorillas, with their elbows out and their knuckles facing forwards, unless they're actually dragging their knuckles along the ground."

I laughed at this image of men and Helen smiled fondly at me. She was clearly glad I was happy with the situation.

"Now you've finished your work, would you like to try on your maid's dress?" asked Helen.

Would I? "Yes please Helen," I said

"Well go and get it then, but do be careful on the stairs in those shoes."

I went up the stairs as fast as the six inch heels would allow. I took off the skirt, blouse and slip stepped carefully into the petticoats, holding onto the vanity to maintain my balance. Having put the petticoats on, it seemed the only way the dress would go over the flounces of the petticoats was over my head. I unzipped the back of the dress and lifted the skirt over my head, carefully pulling the bodice after it and putting my arms into the sleeves. I arranged the skirt over the petticoats and reached behind my back for the zip. I got it most of the way up without a problem but the last three or four inches were impossible to reach. I looked at myself in the mirror. "Wow," I thought, "I'm HOT". As Helen had said in the shop, the skirt was very short over the petticoats; the tops of my stockings were visible and that was looking down from a height of over six feet tall in my heels.

I went carefully down the stairs, taking care to bend my knees because my ankles were so straight in the heels.

I flounced carefully into the living room with the petticoats bouncing the skirt of my dress up and down as I walked. As Helen told me, I kept my elbows close to my ribs but had to bend my elbows so my hands didn't touch my skirt.

"Ooh, you little floozy, look at you," said Helen, "those legs, they go on for ever, you lucky girl. I am really going to enjoy training you. Can you pick up my coffee cup and take it into the kitchen, please Annabel." Knowing Helen was watching me, I bent me knees fully and, keeping my knees together, stood up again. It wasn't easy but I saw Helen smile at my effort to be a real girl.

I flounced into the kitchen and put the cup in the sink. Silently Helen had followed me and as I leant over the sink she pressed me from behind up against the sink.

"I could take you now, you gorgeous sexy thing, but it wouldn't be fair, not until you're properly trained."

I didn't know what she meant. I was powerless to move because of the heels. She reached round in front of my thigh, under my petticoats and gave my balls a squeeze. For the second time in two nights, I gave a gasp that was partly surprise, partly pain and partly pleasure.

Still holding me with my knees pinned to the sink she pulled down my panties and pressed something cold and slimy against my bottom.

"Lean forward and relax, Annabel darling, you will love this. She pressed the cold thing against my bottom and, as I relaxed, I felt it enter me. Then she hit the switch and I felt the vibrations coursing through my bottom and around to the base of my penis. I was squirming; the sensation was nothing like I had ever felt. I didn't want to cum but I was so aroused that I desperately wanted relief. Helen sensed this and while gently moving the vibrator to and fro in my bottom with her left hand, she started to rub my penis with her right. In a matter of seconds, I fired my load of cum into her hand but still she kept on with the vibrator.

"Oh Annabel, you've discovered your clit and you love it. You are really one of the girls now. What about a second orgasm, you know you want to."

Instead of the erection losing its strength as it usually did for me, the vibrations and all the other sensations kept it strong while she continued to rub my penis and move the vibrator gently in and out of my clit. I was squirming worse than ever; I thought my balls were going to explode.

"Annabel, you are the sexiest girl I have ever made love to," Helen whispered in my ear, "I'm so glad I've found you. We're going to give each other so much pleasure. You look so gorgeous in your petticoats and stockings and your corset gives you really pretty, girly curves."

The pressure was building again and with a gasp of pleasure and exertion I thrust violently and came again into my petticoats.

"Whoa, Annabel you go like a rattlesnake," said Helen appreciatively.

"Thank you Helen, that was amazing," I said honestly when I recovered my composure, "I have never had feelings like that before. It's so sexy being a girl."

"I think you deserve a cuddle, you've done a lot today and Annabel has lost her virginity. That's an important moment for a girl. Go back into the lounge and take those shoes off. You'll have time enough to practice walking in them in the week. Oh, and take your petticoats off and soak them or they will be ruined, the amount of cum that went into them."

I slipped the petticoats off and carefully stepped out of them while Helen filled the sink with water. I still felt sexy in dress without the petticoats but there was no doubt that the petticoats made the dress look really hot.

Helen mentioning the heels reminded me that their main function was to train me to walk correctly, so I carefully minced back to the living room and unbuckled them.

Helen followed and we sat together on her settee and cuddled while we watched a chick-flick on the TV.

Soon it was time for bed. Helen showed me how to take off my make-up and apply moisturiser.

"You need to sleep in your corset, to make the figure training work properly. I'll wake you when I have finished in the bathroom tomorrow morning because I need to lock you in your shoes before I go to work. And tomorrow will be your first full day as Annabel the trainee maid."

 

To be continued.

  

  

  

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