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

  

Annabel's Story

by Annabel Naismith

 

The First Evening

5 years ago, when I was 19, I went on a tour with the field hockey club I used to play for. It was an annual event to the South West of England. After the last game, our hosts organised a dinner dance. By tradition, none of the tourists brought wives or girlfriends – obviously they would prevent us from enjoying ourselves in the evenings by restricting our male bonding activities, drinking, playing cards, etc. To balance the numbers at the dinner dance, the female section of the host club were encouraged to attend, together with unattached female friends. The encouragement was to see if they could "pull" any of the unattached tourists.

Over the years, a history of successful conquests had been established. For me, on my first experience of this kind, this was a source of immense interest. So much so that it was one of the main reasons to go on the tour.

The tables at the dinner seated 8 people, two men from the host club, two men from our club and four ladies. We all had name cards by our places and found myself sitting between Linda and Helen. Linda was a very pretty blonde, a few years older than I and Helen was an attractive brunette with strikingly dark eyes and a little older still. As soon as we were seated, it became clear that Linda and Helen worked together and were good friends. Linda played hockey and Helen was at the dinner dance to enjoy the evening and see what developed.

The meal was uneventful; the food was pleasant enough and there was plenty of wine. The conversation between Linda and Helen had concerned their work and their relationships. I learned that Helen was Linda's line manager in the financial services company where they worked. Linda had recently divorced and Helen had never married. They asked me about my family and job. I told them my parents divorced when I was 7 and my mother re-married and had 3 children with her new husband, I didn't see my father often and I worked in the accounts departments of different companies on temporary contracts.

By the time we finished eating, I was starting to feel rather drunk. Linda went off to dance with the guy sitting the other side of her.

"Come on, Ian" said Helen, getting up and taking hold of my arm. It would have been rude to refuse and anyway, for all that she was probably 15 years older than I, she was very attractive and had an athletic figure. She was wearing a black evening dress with a hem-line just above the knee. In her 3 inch heels, she was perhaps an inch taller than I. We had several dances and returned to the table for some more drink. Linda was still dancing with the other guy, so Helen and I returned to the dance-floor.

Eventually, the music slowed and Helen and I were still dancing. I held her close to me and she seemed happy for our bodies to be touching. As the music stopped, she gave me a quick kiss. I was rather embarrassed, being kissed by a woman nearly as old as my mother and in front of the entire hockey club!

"Don't worry," Helen reassured me "This won't be the most embarrassing thing that occurs this evening."

The time came to leave. Helen asked if I would like to go back to her house for a nightcap. I had started to like Helen – she had a friendly but quietly assertive manner. I am naturally rather shy and was perfectly happy to accept her invitation.

The taxi took us to a pleasant 3 bedroom house in a nice neighbourhood, not far from the hotel where we had been staying and where the dinner had been.

Helen opened her front door and showed me into her living room.

"Let me take your jacket," said Helen. "What can I get you to drink?"

"I've had enough wine, I think. Can I just have a black coffee, please."

"Of course," answered Helen "I'll have a coffee too. Have a seat while I put the kettle on." And with that she went into the kitchen and soon there was the familiar sound of kettle boiling. Helen returned with two steaming mugs.

"There you go, Ian" she said putting the mugs on the coffee table.

Then she sat next to me and lifted my right arm so it was behind her back and then she kissed me – a long lingering kiss. Her tongue flicked into my mouth and she put her hand onto mine and lifted it onto her leg, just above her knee. She removed her hand and I carefully inched my hand up her thigh and under the hem of her dress. I realised she was unbuttoning my shirt. She undid three or four buttons, then thrust her hand inside and started clawing at my chest. I was not sure what to do when she suddenly pinched one of my nipples and squeezed it gently. I was surprised and let out a small gasp.

"Is that all right?" asked Helen

"Oh yes, it's fine. It's just that no-one has ever touched me like that before."

"Please don't think I'm being too forward, but do you like it when the woman takes control?"

I was a bit surprised again. "Errm, I don't know really. All the girls I have dated have been teenagers and they – well – they didn't really – you know"

"You've never had a woman take control before?"

"No" I confessed, honestly.

"I see. What would you like us to do – I'm very broad minded. Is there a fantasy that you would like to try?"

"Well, I have often thought what it would be like to be the servant of a wealthy lady." I began, my mouth inexplicably went dry.

"Go on," Helen prompted.

I swallowed hard and went on. "A female servant."

"A female servant? So you would like to be a lady's maid?" Helen smiled mischievously as she looked intently into my eyes.

"Yes." I said hesitatingly.

"So you would like to wear a little black dress, stockings, petticoats and high heels and run about with a feather duster?"

"I guess." I was starting to regret having brought this up but Helen was just beginning to see her opportunity.

"And you would like to take her breakfast in bed. So, if you had sex with a woman, it would be with you being a woman? You know, like a lesbian."

"Well not necessarily," I replied, trying to keep my options open.

"Ian, you can't wear a dress and have a great big penis lolloping around. And you can't be called Ian. What name does your female persona have?"

How could she have known that I had given her a name? I replied quietly, "Anna, because my first name ends with the letters'a' and 'n' and my second name begins with the letters 'n' and 'a'. It's like a secret middle name, just like Anna is my secret persona."

"Anna is my mother's name – I can't possibly call you that. What about Annabel? Would you mind being called Annabel, just for tonight"

"No, not at all, it's a very pretty name."

"Ok Annabel, come upstairs and let me see if I have something you can wear to get you in the mood."

We went upstairs to her bedroom and she opened the closet. "There's a slip you could have and a white blouse and a plain black skirt. Let me see if I have an old bra and panties and some tights and some shoes. What size shoes do you take?"

"Size 8" I replied, unable to take in what was happening.

"Oh, I take a 7, so you should be able to get into an old pair of mine for now."

Helen rummaged around and found the underwear and shoes.

"Right," said Helen decisively. "Take off all your clothes and put these on, then you can come and serve me downstairs. Don't take too long, now. I don't want a servant who is going to keep me waiting."

With very mixed feelings, I obeyed. The bra was the first hurdle. I got my arms through the armholes OK but then found it impossible to fasten the clips behind my back. I decided to cheat and removed my arms and fastened the clips in front of me, then slid it around to the back and put my arms through the holes and lifted it into position. Next were the panties, fairly large cotton ones and I carefully tucked my penis down and back so as not to show too obviously. Next came the tights – I carefully rolled them down so I could get my thumbs to the toes, then rolled them one leg as far as the knee and then repeated for the other leg, then carefully slid them the rest of the way up my legs and fully into position. Then I put on the slip, blouse and skirt. Try as I might, I could not get the skirt to fasten at the waist, so I did the zip up as far as it would go and checked myself in the mirror. I did a twirl, not bad but not very convincing as a girl. The face and hair were still very much Ian but my legs looked OK in the mid-thigh length skirt.

Then the shoes. The tights helped them to slip on but they were still a little tight. I checked myself again in the mirror and then carefully went down the stairs and into the living room.

"Ah, hello Annabel," said Helen in a businesslike way. "You look very nice. Why do men have such gorgeous legs, it's not fair".

"Thank you, Helen" I said and gave a little bob.

Helen smiled, she seemed to be enjoying this game enormously and I was enjoying it too. It was my long-time fantasy and to be playing it out with this attractive and assertive but not overly dominant lady was more than I could have wished for.

"Turn around Annabel"

I did as instructed.

"Ah, I see your waist is too large, we may need to do something about that."

"I'm sorry, what do you mean?" I asked

"Corsets, Annabel, corsets. No maid of mine is going to be seen with a figure that won't allow her skirt to do up."

Before I could ask about the corsets or "maid of mine being seen", Helen continued.

"Come here my dear and kneel down."

As instructed, I knelt in front of Helen.

"Now Annabel, please give me oral sex."

Don't beat about the bush, in any sense, I thought. "Very good Helen," I said.

While I had been changing, she had removed her tights and panties. I slid my head towards her and she widened her thighs and pulled my head towards her. I inserted my tongue and started to lick vigorously at her vagina. I had never performed oral sex on a woman before; the smell and the taste were so strong. I quickly realised the spot she liked to be licked the most; she gave an involuntary flinch every time I licked her there. After a minute or so, she began to writhe and breathe heavily. She came with such a torrent that I had trouble breathing but she was thrusting into my face so I knew I should continue. She relaxed a little and my licking decreased in intensity and as well. I started to move away but she pulled my head back towards her.

"Keep going, that's wonderful" she said.

I thrust my tongue back into the dampness of her clit again. It tasted so good. Soon Helen was twitching and breathing heavily again. She came again just as previously and this time I kept going with my tongue, frantically trying to keep in contact with her G-spot, which was thrusting at me like a creature possessed.

"Oooohh, Annabel, you are so good!" said Helen, as she collapsed on the edge of the chair. "Wherever did you learn to pleasure your mistress like that?"

"Thank you Helen, I try to give satisfaction," I said a little cheekily, and I was feeling pleased with myself for having given her so much pleasure.

"Now, as a special reward for giving me so much pleasure, you may masturbate".

Not for the first time that evening her directness surprised me.

"I cannot possibly pleasure you, my dear, but you may pleasure yourself. Would it help if I spoke of some of the treats I might have in store for you?"

I obediently lifted my skirt and slip, pulled down my tights and panties, took my penis in my hand and started rubbing its length, still kneeling in front of Helen.

"I would very much like to see you again, Annabel. I think we can develop this situation and both of us can derive a lot of satisfaction from it. There are some things you will need, such as your own underwear and uniform. I would like to see you in a pretty maid's dress with pretty petticoats. You do like petticoats, don't you?"

She could tell I did like petticoats from the increased vigour with which I rubbed my penis.

"Yes, we must get you petticoats that have enough material to make your dress stand out and be visible when you bend over. What colour shall we have? White is the usual but I like the idea of a different pastel shade, yellow possibly or pink. Perhaps all three and you could wear more than one at a time. White and pink would look pretty together and it would mean the skirt of your dress was pushed out so far, you would need to be very careful not to show your little panties. Imagine the feeling of all that satin rubbing against your bare thighs over the tops of your stockings. Ah there we are." She finished as I came onto her dress. "It's lucky this dress can be hand-washed; that can be your first job after breakfast in the morning."

"And now to bed, Annabel. We have a lot of things to sort out in the morning. You will sleep in the guest room and I will find you an old nightdress for tonight."

I meekly followed her up the stairs, felling tired and happy.

Helen showed me into the guest room. Slightly reluctantly, I started to take off the blouse, skirt and underwear while Helen went to her room. Soon Helen was back with a nightdress. The nightdress was black and satiny with little shoulder straps and lacy trim around the bust and hemline. It reached to my mid-thigh.

"This is really pretty, thank you," I said. "I love the feel of the satin next to my body."

Helen hugged me. "It's one of the great benefits of being a girl that you get to choose from so many different fabrics. And thank you for such a wonderful evening, Annabel. You have been really brave to tell a stranger your innermost secrets. I hope you had a good time too?"

"Oh yes," I said. "I really enjoyed the feel of the clothes and giving you so much pleasure."

"Annabel." She sat on the single bed and pulled me down on the bed towards her. "Would you like to stay being Annabel? If so, you will need to check out of your hotel in the morning and then we can do some shopping. Would you like that?"

"Well yes," I said "but I have work on Monday and I need to get home."

"You're a temp, the agency will be able to replace you. It's their job. You can tell them you have found another job, while you were down here. It's not even a lie," she smiled to herself. "You can be a trainee maid. You need training but I am happy to provide the training you need, if you would like me to. Would you like to be trained as a proper lady's maid? You know, things like deportment, make-up, dress-sense. I would love a maid to keep the house tidy and one that gives so much pleasure in the bedroom would be even better. How about it?" Again her deep brown eyes looked intently at me.

How could I refuse? I was living out the fantasy of my wildest dreams. I simply nodded and for no reason a tear started to fall down my cheek. Helen put her arm around me and kissed me.

"Ahh," she said tenderly. "You're even starting to have a girl's emotions. Now get into bed and get some sleep. We have a lot to do tomorrow."

With that she stood up and swung my legs under the duvet. "Goodnight, my sweet little maid." She said tenderly, stroking the hair over my ear.

 

To be continued

  

  

  

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