This is the story of how Ian 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.

The First Day (Part 2 - synopsis)  Ian is now living full-time as Annabel. She has been shopping for her uniform and received her first lessons in becoming a lady's maid.

The Second Day (Part 3 – synopsis)  Annabel's first working day, which ends with her meeting Becky, the hairdresser of her mistress Helen.

 

Annabel's Story

by Annabel Naismith

 

Part 4. The Lingerie Party

The rest of the first week my working days passed in a similar way to Monday. I did the washing and cleaning chores and prepared Helen's evening meal. Every day, Helen laced me ever tighter in the corset and padlocked the straps on my 6 inch heels to help with my training.

While Helen was at work on Thursday, after 4 full days of life as Annabel, the doorbell rang. It was the postman and he needed me to sign for a parcel. I could feel him looking lecherously at my long legs, while I signed the receipt for the parcel. As I stood in the hall I was on a step, so I must have appeared incredibly tall to him. I don't think he read me as a guy in a dress though, now that my hair had been dyed and curled by Becky a few evenings previously and my make-up was now quite well practiced under Helen's critical eye. Also the tightly laced corset, which now reduced my waist to 26 inches, gave me a slim girl's figure.

I left the parcel on the occasional table in the hall and thought no more about it as I continued with my chores.

When Helen arrived home, she noticed the parcel.

"Oh good, I'm glad that has arrived. I ordered some things on the internet which will complete your training, Annabel," she told me. "We will try them out after dinner."

I was intrigued and finished eating, wondering what surprises Helen had for me.

While I cleared the dinner table, Helen opened the parcel and I could hear the sound of rustling paper as she opened the various items. Then she called me into the living room.

"OK Annabel," said Helen, "I need you to take all your clothes off."

I slipped off my shoes and unzipped my dress, and taking it of by lifting the hem of the skirt over my head. Then I slid my petticoats down my stockinged legs and stepped out of them. I picked them up and put them neatly on a chair. Next I unclipped the garters holding my stocking tops and slid them off my smooth legs, putting them on the chair next to my petticoats. Helen came over and undid the laces on my corset and slipped it off. Finally, I unhooked my bra and took off my panties.

Helen inspected my body. There were red marks from the boning in the corsets having been tightly laced since the morning. Otherwise, I had the body of a slim young man and the face of a pretty blonde girl.

"Annabel," she said, "I have bought some items to complete your look. There are two obvious things wrong with your body; you have no boobs and you still have a penis. First of all put these on," she said, handing me a flesh-coloured thong-like garment.

I slipped it on and slid it up my legs. As I tucked my balls and penis back between my legs, I was amazed to see my manhood disappear, to be replaced by a realistic looking vagina.

Helen looked critically at me. "Yes, that's good," she said. "The web site said it was life-like and I have to say, I'm impressed. You wouldn't know there was a penis lurking behind your pussy. OK, let's try your boobs."

Helen picked a pair of prosthetic breasts and placed them on my chest.

"I got you a B-cup as you haven't had a chance to get used to growing them. I hope you won't be disappointed."

"No, Helen, I'm sure I won't," I said. "I really appreciate the trouble you're taking for me."

"OK, hold still. The boobs are held in place with double sided medical adhesive patches. They say you can go bra-less up to 50 times."

How was I to get them off?

"They have supplied some special adhesive to remove them." Helen must have known what I was thinking. "I'll keep that to stop Ian trying to come back and take my Annabel away from me."

With that, she pressed the first breast firmly in place. I was surprised at how heavy it felt as it pulled the skin on my chest. However much must large breast weigh? Helen pressed the other breast in place and stepped back to inspect her handiwork.

"Excellent," she said, "now you like a girl even when you are naked. Turn round."

I performed a slow twirl. Even moving slowly, I was aware that my breasts were moving slightly as I moved. What would they do if I ran, I wondered.

"Not bad," said Helen, "I would like to see more flesh on your hips. How do you feel about hormones to fill out your hips? Your skirts and dresses will hang much better."

"I don't really know," I said indecisively, "I have wondered what it would be like to be a woman. My main doubts are whether I can pass well enough to get a job and whether I could enjoy sexual satisfaction."

"You can certainly pass well enough. I can't say whether you would get sexual satisfaction. It seems to me you are more comfortable in the submissive role; traditionally the female role in a relationship. Just taking hormones is not the same as a complete sex-change, although, admittedly it could be a first step. Why don't you try for a few weeks and see how you feel. All that will happen is your hips will become a bit fleshier and you will just start to start to develop boobs. If you want to stop after a week or two, there will be hardly any difference. But if you really want to become a woman, you can make that decision later."

It was time to make an important, if not final, decision. I knew I had always been interested in girls for two different reasons, firstly because I wanted to make love to them and secondly because I wanted to be one of them. I had always wanted to wear their clothes and their make-up and join in their conversations about fashion, relationships and even about boys. Besides, I was really enjoying my life as Annabel and would like to continue my exploration in my feminine role.

"Ok," I said, "I will start taking hormones just so we can see how it develops."

"I had a feeling you might say that," said Helen, "so I got some oestrogen patches. You just put one on and leave it. The oestrogen is absorbed through your skin and gradually you will develop a more feminine shape."

With that, she put a patch on my left shoulder blade, pressing it firmly into place.

"Now," said Helen, "there is just one last thing to do to show if you are really a submissive at heart. I need you to masturbate and cum into a bowl. You will see what this is for in a few minutes."

I just shrugged, it seemed a strange request but it would not cause me any discomfort. I pulled down the thong and started to stimulate my penis.

Helen left the room while I was masturbating and a few minutes after I had finished, she returned. She was wearing a masculine suit with a double-breasted jacket and flat black shoes. Her hair was tied back in a pony-tail.

"Put your thong back on Annabel," said Helen in a commanding tone of voice. I did so.

"Come here and suck me," said Helen, sitting on a chair and unbuttoning her jacket. I knelt in front of her and undid her zip. I was surprised to find a large and very realist strap-on dildo. I hesitated.

"I said suck me." Helen sounded insistent. I licked the tip of the dildo then opened my mouth kissed the tip sensually. I took the first inch or two of its length into my mouth and worked up and down. Helen pressed hard on the back of my head and forced me to take more of the dildo into my mouth. I realised that this was a double-ended dildo because of the moaning that Helen was doing. I recognised the sound she made as her g-spot was being stimulated. After a few minutes she paused. She dripped some of the cum from the bowl into which I had masturbated on the end of the dildo. Then she pulled my head towards the dildo. I took the dildo back into my mouth taking my own cum into my mouth and swallowing. After a few minutes, of oral stimulation, Helen became more aroused to the point of orgasm.

"Oh, Annabel," she said, "let's get rid of this dildo. I need you to lick me the way I know you can."

She stood up and took all her clothes off and removed the dildo. Before she had sat down, I had my nose in her musty bush and my tongue was exploring her clit, looking for her g-spot. I quickly found it and Helen gave a moan of pleasure. I licked her more urgently, thrusting my tongue in and out, while she gave cries and moans of pleasure. Soon she gave the familiar tensing and thrusting which were the precursors of her orgasm. She came with a cry of pure ecstasy.

"Whoa, Annabel, you're just wonderful. I just love they way you do that to me. Thank you."

I leaned back.

"Come and sit next to me, Annabel, darling," said Helen. "How did you feel sucking my penis?"

"It was OK, I guess," I replied. "I don't know how I would get on with a real man. I knew it was a lady with a fake penis."

"Maybe we need to try you with a real man one day," said Helen thoughtfully.

"But enough of that, tomorrow night, I will be having some girl friends round for a lingerie party. We will have a few bottles of wine and play some games while you serve wine and snacks. Then you might like to join us to see what a girly night is really like. The organiser will be bringing lingerie for us to try and girly toys for us to play with. I'd like you to wear your maid's dress and 6 inch heels, so you really look the part. And Becky will be coming," she added with meaningful emphasis. Becky had styled my hair a few nights previously and she and Annabel had become lesbian lovers on their first meeting.

"Thank you, Helen," I said, "I will love that. It will be a rare privilege for a man to go to party like that."

"Yes, but you won't be going as a man. As you will be wearing 6 inch heels in the evening, it would be sensible for you to wear your lower heels during the day tomorrow," continued Helen, in her pragmatic manner.

"Now you go and have your bath and I will come and lace your corset when you're ready."

For the rest of the evening, my thoughts were dominated by seeing Becky again and being at the girly lingerie party.

Friday morning arrived and Helen left for work as usual, leaving me to my chores for the day. The only changes my usual routine of washing and cleaning were that my chores were easier in the lower heels and that I was not going to have to make dinner for Helen.

Helen arrived home later than usual because she had been to the superstore to get snacks and wine for the party. By the time she arrived, I had changed from the skirt and blouse I wore to do my chores and into my maid's dress, with the full petticoats underneath. Beneath my panties I wore the special thong that hid my manhood and made it appear as if I had a vagina. I had also done my make-up, a little more dressily than for day wear, with blusher, eye-shadow and eye-liner, mascara and lip-liner and well as lipstick.

"Annabel, help me get the shopping in, please," said Helen.

Helen had parked the car on the drive with the rear of the car facing the road. The short skirt of my dress, flared out with the petticoats, meant that I had to be very careful to reach in and get the shopping bags without showing my stocking tops and panties to anyone passing. I carefully bent my knees and reached into the car trying to keep my back as straight as possible. I think I did OK; I didn't notice any car tyres screeching or hear any crashes.

Once all the bags were in the kitchen, I put all the shopping away and started to prepare the snacks, making sandwiches, setting up trays of dips and preparing salads.

Soon Helen joined me, having showered and changed.

"Good, Annabel," she said. "Now go upstairs and get your high shoes so you will be ready when our guests arrive."

After I came back downstairs, Helen checked the padlocks around the ankle straps were fastened, and then I started to put the snacks onto plates in the kitchen.

Shortly before 8 o'clock the first person to arrive rang the doorbell and I promptly answered it.

"Hello, I'm Carole, the party organiser. You must be Annabel," she said. "Helen told me to expect you. You look lovely. Can you help me with my cases, please."

"Yes, of course," I said and walked out into cool night air to her car. Carole had parked in the road and again I had to reach in to the rear of the car to get her cases. She had an estate car with the rear seats down, so some of the cases were out of reach of my arms. As a man it would have been so easy to just bend over from the waist and reach in. In a maid's dress, I had to be very careful. I could not sit on the rear of the car and reach in because I knew the petticoats would lift up the front of my dress. In the end, I knelt on one knee on the back of the car and managed to reach in and get the two cases. I don't think I caused too much of a distraction to traffic. Carrying two heavy cases, one in each hand, meant that my arms pushed into the sides of my petticoats. This in turn meant that my petticoats pushed the front and rear of my dress up even more than usual. Fortunately, I only had to walk twenty yards or so and I just looked straight ahead and hoped I was decent.

I was just walking into the drive as Carole came out.

"Well done, Annabel," said Carole. "That should be everything."

She locked her car and followed me into the house. I set her cases down in the lounge and returned to the kitchen.

A few minutes later the doorbell rang again. It was Linda, the pretty blonde colleague of Helen's whom I had met at the dinner the evening I first became Annabel. Linda was accompanied by another colleague, Jackie. Both were wearing simple tops and smart black trousers.

I greeted them with a curtsey and took their coats.

"Thank you, Annabel," said Linda. "You look a bit different from Saturday. And I thought Helen would make a man of you. Still never mind, you make a lovely maid."

"Thank you, Mistress Linda," I said with a little bob and showed the two ladies into the living room. Helen greeted her two colleagues and I went to get drinks for the new arrivals.

For the next 20 minutes or so I was kept pretty busy, answering the door and serving drinks and snacks. The last to arrive was Becky with her friend Donna; it was Becky who had done my hair a few evenings previously.

"Good evening, Mistress Becky," I greeted her.

"Hi Annabel," she said with a friendly smile. "God, you're so tall, those heels. How the hell do you walk in them?"

"I've been practising. Mistress Helen locks me into them every morning before work to train me."

"The sadistic cow!" Becky sounded shocked.

"Oh, that's not fair, I like them and it's not so bad once you get used to them."

I took Becky's coat and went to hang it in the closet. Instead of going into the living room, Becky followed me into the closet. She squeezed the back of right leg, just below my petticoats.

"Annabel, you look good enough to eat, you little minx," she whispered. "If I ever get you alone…." She did not finish her sentence but went into the living room to join the others.

I returned to my drink and snack serving duties. I lost count of the number of wine bottles I had opened. Most of the ladies were sitting and I had to bend my knees carefully to serve them, so as not to show my panties.

It was nearly 9 o'clock when Helen and Carole decided to start the lingerie party.

"Annabel, will you clear some of these things away, so we can start the party," said Helen. I picked up the dirty plates and took them into the kitchen, then started to wash them. I had been gone a few minutes, listening to the sounds of conversation and frequent laughter, when Helen came into the kitchen.

"Annabel, we have decided we need a model. Models are tall and have long legs. So you can leave that for now and come and join us."

I had not expected this but I recovered myself quickly.

"Thank you, Mistress Helen. I will be happy to."

I went into the living room. Carole was holding a flimsy red baby doll and matching high-waisted panties. She was also grinning maniacally.

"You'll need to take your dress off," said Carole.

I looked to Helen to check this was OK. She smiled and nodded. Oh well, I thought and undid the zip of my dress. As always, the dress would not go down over my petticoats, so I had to lift the hem over my head and remove the dress that way. I then put the dress on a spare chair.

"And the petticoats." Carole was enjoying this. I was sure a lot of her enjoyment came from knowing there was really a man stripping.

I put my hands inside the elastic waist of the petticoats and eased them down my stocking-clad legs, then stepped carefully out of them and put them on the chair with the dress. I stood in front of 8 partially drunk and lustful women wearing 6 inch heels, sheer black stockings, pink satin corset and a pink satin bra and panty set.

"I think we can get the idea now," said Carole. "Put these on."

I took the tiny red panties she gave me and stepped carefully into them. I slid them up my legs and put them into place. I couldn't initially realise why they were all laughing lecherously, then it dawned. There was a large hole in the crotch of the panties, through which my pink satin panties could clearly be seen. Then Carole gave me the flimsy baby doll to put on, which I managed to do without further embarrassment, despite the fact it only reached to just below my waist.

"Give us twirl," said one of the girls. So I minced to the end of the living room, turned and as I did so the flimsy material of the baby doll swirled out. Then I walked as sexily as I could back to spot were I had been standing.

This was repeated with several other costumes. Some were more nightdresses and there were some role-play costumes. I was a nurse, a sexy Santa helper and a rather sexy Little Red Riding Hood.

Eventually, Carole said "Would anyone else like to try modelling. We seem to have side-tracked our serving girl and I need some more wine."

Other girls stepped forward enthusiastically after my performance, while I went to open yet more wine bottles, taking my petticoats and maid's dress with me. I put the petticoats and dress back on before returning to the living room to top up all the wine glasses. Then I returned to the kitchen to complete tidying up.

After several minutes the drunken laughter had reached a crescendo and Helen drunkenly lurched into the kitchen.

"Annabel, we need you again," was all she could manage. She was close to tears with laughter. Laughter is infectious and I smiled curiously as I followed her somewhat erratic progress back to the living room.

In the living room I was greeted with the sight of Becky gyrating provocatively and wearing an absolutely enormous strap-on dildo.

"…and if you can get your man to go down on you when you're wearing a Long John," Carole was saying, "you'll know you've got him."

With that Carole pushed me forward so that I stumbled on my heels and tripped, falling to my knees in front of Becky. I knew what was expected.

Becky thrust her enormous appendage at me and I started to lick the end. The girls were delirious with my performance, so I thought I would play up to them.

"Oooh, Becky you're such a big boy," I groaned while licking the obscene length of the thing. Then I put my hand on the base of it while I took the tip in my mouth and writhed sensually while letting it go in and out of my mouth. Becky continued to thrust and gyrate.

"I'm going to take you, bitch," she announced suddenly and spun me round, still on my knees, so my face was in Linda's lap. Becky knelt behind me and lifted my petticoats and thrust the enormous dildo at my bottom. This action was greeted with roars of approval from the other girls. "Get them off!" "Go Becky!" "Let her have it!" She pulled my panties down to my knees and thrust erratically at my anus. Instinctively, I reached behind me back, partly to help her aim and partly to move the flesh coloured thong that was struggling to hold my penis in check. "You always have to help them," came a catcall, accompanied by raucous laughter, followed by "Ooh, she really wants it," in a tone that was full of wonder.

"You'll need a drop of lube," said Carole and she applied a large drop to the end of the dildo, which Becky had now aimed accurately and was pushing hard, trying hard to enter me. The lube enabled my anus to expand to take the top of the monstrous dildo. Becky continued to thrust and I was able to relax enough to let the dildo enter me, gasping in pain more than once or twice. I thought my anus was going to tear, it was so tight, but after a few long strokes the dildo worked its way in.

"Suffer you bitch," said Becky coarsely and thrust still more vigorously. I still had my face in Linda's lap and she started to thrust her groin toward my face. I could feel the huge dildo pressing deep into me. The other girls were roaring their approval and encouraging Becky to greater effort. It was as if thousands of years of women being treated as sex-objects by men was being avenged in this one act of depravity. With all the thrusting, I was being forced rhythmically into Linda's groin area and I could feel her go tense and breathless; I realised she was close to a climax in her pants.

After two or three minutes, Becky gave four or five particularly long and violent thrusts accompanying each one with a loud grunt, then suddenly she withdrew the dildo, fell back on the floor and promptly feigned sleep by snoring loudly. Her performance brought cheers, clapping and laughter from all the girls.

Meanwhile, I was struggling to recover, still leaning on Linda's knees with my face in her lap and my panties by my knees.

"Just like a bloke, gets his satisfaction then falls asleep when we need ours," observed Jackie. There were murmurs of agreement.

"I can't believe she took all that," said Donna, "she took it all. And the size of it! It's obscene!"

"Ooh, look, she still wants more," continued Jackie, "and what is that thong thing you're wearing?"

"It helps hide his willy when he's in a skirt," said Helen.

"Let's see." Before I could do anything, I was helped up and had to hold my petticoats up, with my panties still around my knees so all the girls could inspect my thong and false vagina.

"God, that's amazing!" "It's really realistic." "Do your balls hurt being squeezed in like that?"

Becky was kneeling close to me on the floor and she extended a hand to pull the thong from the front and expose my manhood. "He's quite big really," she observed, "I'd have thought he would be really small to hide it so well."

"Erm, I think Annabel might like to go and fix her make-up," said Helen coming to my rescue. I pulled my panties up and went to the kitchen to try and recover some composure. As I was leaving, I heard Carole say "who's going to buy a nice surprise present for her man, then?"

I looked at my face in a compact mirror I saw in Helen's bag. I was a mess! My hair looked bedraggled; my lipstick was smudged and uneven. There was nothing for it; I went upstairs to my room to repair the damage as quickly as I could. I was only upstairs for 5 minutes or so and then I returned to the kitchen to resume cleaning up.

Eventually Helen came into the kitchen. By his time she was quite drunk. "The first taxis will be here soon, Annabel," she said. "Make sure you give our guests the right coats."

The first taxi to arrive was for Becky and Donna. I felt disappointed that Becky could not stay longer and she seemed a little distant as I gave her coat to her. I wondered if I had upset her with my performance.

Over the next 30 minutes or so taxis and husbands arrived regularly to collect the guests. I got to answer the door to several of the drivers. I don't think any of them guessed I was a guy; all of them looked at me with unashamed lust!

Carole was the last to leave. She was absolutely delighted with her evening's work.

"Annabel, you were sensational," she enthused. "That is the best evening's sale I have ever had in such a small party. I've been doing these parties for 15 years and I have never seen a performance like that. It was brilliant. You really got the girls going. Here take this." And she handed me a 20 pound note. I hesitated. "Go on," she insisted, "with the commission I make tonight I can afford it. Do you know," she added, "I have never sold strap-on dildos to EVERY girl at a party before. There are going to be a few painful arses in this town soon! All the men will be bandy! And they all bought lube. LOTS of lube. And dresses and lingerie.

"I'm ready to go now," Carole added, "Can you carry my cases to my car, please."

Yes of course, Mistress Carole."

"You are so precious," said Carole shaking her head.

I carried Carole's cases to her car, carefully lifting the cases into the back trying best not to bend at the waist and give anyone passing a flash of my panties and stocking tops. However it was after midnight and the road was very quiet.

"Good-night Annabel and thanks for everything you've done tonight," said Carole as she passed me on the way to her car. "Take care. I'm sure I'll see you again very soon."

"Good-night, Mistress Carole," I said and went back into the house.

I found Helen sitting in the living room. She looked tired and cross.

"Your behaviour was an absolute disgrace," she said. "That embarrassing performance in front of all my friends. And colleagues," she added, "People I work with. Important people. Senior managers, some of them." Helen paused as though she could not think of the words to express her anger. "I'll talk to you again about this in the morning. I'm going to bed now. Tidy this room up and be quiet while you're doing it."

With that she went upstairs to bed.

I felt really worried about my whole future as I put the furniture back in its proper place and carried the plates and glasses into the kitchen. I finished washing the dishes and glasses then dried them and put them away before going to up to bed.

I was still locked in my 6 inch heels, there was nothing for it. I would have to sleep in them!

To be continued.

  

  

  

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