Magic Dress - Nancy Pt. 03

CHAPTER 9

It was such a trivial thing. A man and a woman meeting over coffee in a friend's flat. Just a couple of hours on a Saturday afternoon. However, the preparations were only slightly less than for a Royal Wedding. Becky played the part of Jeremy in sort of rehearsals and we (or rather they) decided how the room should be arranged, who would sit where, what would be served and when, plus plans for toilet and contingencies such as my bursting into tears. I practised moving around the room in a ladylike manner without bumping into the furniture, plus standing and sitting and various scenarios from shaking hands to being hugged and kissed. I wanted to rehearse some questions and answers, but they refused, saying the whole point was for me to be myself.

There was no question but I was going to be in the green dress. I wanted suspenders and stockings, but they both forbade it. This was not supposed to be a seduction, just an introductory chat.

I thought they were starting early, but it took longer than I expected to get me ready to their satisfaction. Becky shaved what I had missed on my face, and trimmed and styled my hair a little, with some spray. They agreed that a "no makeup" style would be right, which took a surprising lot of effort with cosmetics to achieve. Becky shaped and tutted over my fingernails and applied a discreet pearl polish. For some reason she also put it on my toenails, though I would be wearing trainers all the time. I was sprayed with perfume.

Becky departed and I waited nervously while Amy tried to distract me.

Finally, the doorbell went. Amy went to answer it and brought Jeremy back into the room. He had a casual jacket, open-necked shirt and smart jeans. He did look handsome, I had to admit.

"Nancy, this is Jeremy from the finance department. Jeremy, this is my best friend Nancy, who works in the same office as me."

He stared at me open-mouthed. I realised I was doing the same, so closed mine, and he followed. He didn't put out his hand or try to kiss me, just said "Nice to meet you," in a slightly strangled voice.

I sat down on the sofa, and Amy motioned him to the chair opposite.

"I'll get coffee," she said brightly.

When she came back with coffee and snacks, we had not spoken or moved.

She poured coffee and remarked "Jeremy says he likes the Discworld books. I think you've got some of them, haven't you, Nancy?"

"All of them," I responded automatically.

"I've only read one," she continued. It was very good, and unusual because all the main characters were female, both goodies and baddies. Witches Around."

"Abroad," Jeremy and I corrected simultaneously, and smiled a little.

He made an effort. "If you've read all of them, Nancy, which is your favourite character?"

"Death," I said immediately.

"Oh," he said. "I would have said Rincewind or Vimes, but now you come to mention it, Death is really good, isn't he? I think he's in a couple I haven't read yet."

"You're welcome to borrow them," I was able to say, "providing I get them back."

The ice was broken. Amy cleverly steered the conversation, so it was not questions and answers between two people, just three friends chatting about their interests. We didn't talk about our histories or what we had done. Just things we liked or had opinions on from the news.

We had similar views, though not identical about several things. It was a bit halting and uncertain, but we managed for a couple of hours, until Amy said it had been lovely to see him, and he took the hint. They kissed each other on the cheek (as she was the hostess, I suppose) and he left saying "Nice to have met you, Nancy. Hope to see you around." I just smiled.

"Right," said Amy. "I'm going to the loo."

She came back with my jacket.

"I'll just clean up and change," I said.

"No, no miss. You and I are going for a little walk to discuss what you thought of him. Some fresh air will be good."

"No, I can't!" I said as I automatically put on the jacket.

("Yes, I can!" I thought.)

"All right," I said.

"Attagirl!" said Amy with a big grin.

So we went out for a walk. It was good to be in discussion, because I was not looking around and thinking about what other people thought. I wasn't even trying to walk like a woman or pretend in any way.

I had to admit he had not done anything wrong, and not knowing anything about him, I would just have said he was a nice man. We had both been nervous, which was not surprising. Amy also told me what she had found out from asking around. He had done some work for charity, and people said he was kind. She had even indirectly found out from someone he had dated that he was funny and considerate, but the girlfriend had moved on with no hard feelings.

I eventually agreed that there would be no harm in seeing him again. At this point we seemed to have arrived back at her flat, where Becky was waiting. Unexpectedly she hugged and kissed me and said "Well, done Nancy! What a big girl you are, going out like this!" Amy and I laughed.

They told me that crossdressing men often took years before they dared to go outside. The fact that I had managed it was brave, but also proved who I was meant to be. Nevertheless, I cleaned up and went back to my own flat as Nigel.

CHAPTER 10

On Sunday she passed on a message. Would Nancy be willing to have dinner at the Kings Hotel on Thursday at 7.30? I said no, because I had been there before and been drunk. Amy said it was unlikely they would connect a drunk young man with Nancy. Anyway, they must have lots of customers and probably didn't care so long as the bill was paid, especially if they got a tip. I guessed Jeremy would have left a generous one, so they would probably treat us well.

Eventually I agreed. There was an argument during the week about what I should wear. Of course, I wanted the green dress, but Amy said Jeremy wasn't going out with a dress, and I shouldn't depend on it as a lucky charm. If Nancy couldn't manage without it, she was a fraud. However, I could wear suspenders and stockings. From my limited wardrobe we eventually settled on the grey dress, with my magic jacket at least.

After work I rushed round to Amy, where all the clothes were ready. I shaved, showered (followed by female deodorant) and had my hair and makeup done.

"We won't do this for ever," remarked Becky. "You'll have to look after your own face!"

It was more than the "no makeup" makeup, but proper "going out on a date" makeup with my lashes well enhanced and some definite eye shadow.

As I prepared to put on the bra, Amy handed me a package.

"A little present from me, with love and best wishes."

It was a pair of plastic tits. Not hard, quite wobbly and pink with nipples. They were to go in the bra instead of socks, and were a major improvement.

"They aren't from Jeremy?" I asked suspiciously. "He can't buy me."

"No, you silly girl! They're from me, from my own money, and don't ask how much, and no you can't return them!"

"Sorry," I said, adding "you're wonderful."

"I know," she answered with a smile. "Now you go and be wonderful too."

Amy took me to the door of the restaurant, gave me a last spray of perfume and more or less pushed me in. She had loaned me a handbag with what she thought were essentials as well as my phone and such. I saw him at the same table as before, and walked taking small steps as I had been instructed.

It turned out there were a few things I had not thought about in being a lady guest. It didn't really help when he moved the chair for me, and I was uncertain what to do about the handbag, but eventually put it on the floor.

He did not order a bottle of wine, we just had one glass each and a jug of water. Without Amy the conversation faltered quite a bit, but at least no-one was apologising or getting upset. He held my hand and said how glad he was that I had agreed to a date, and he hoped it would not be the last.

He asked if I had brought the Discworld book, but I had forgotten. I said I would bring it to work, but he said no, on the next date.

I suppose we learned a little more about each other, but not much. After the main course I went to the toilet: the ladies' of course, and renewed my lipstick. He was watching me as I walked back to the table, and on impulse I raised my skirt just a little with one hand to show a bit more stocking.

Dessert was served, and he said he would go to the toilet. As he got up, I could see he had an erection. For some reason I felt immensely cheerful, and we lingered over coffee. He was quite witty and the evening finished well.

We took a taxi back to Amy's. In the taxi, he asked if he could kiss me, and I said yes. Just a simple proper kiss, then another rather more enthusiastically back from me. He held my hand for the rest of the journey.

At Amy's he told the taxi to wait and took me to the door of the flats. Amy answered the intercom and released the door. "Don't forget the goodnight kiss!" she said. So we went in and had a tentative smooch. I was pleased to feel his stiff cock.

He went back to the taxi, and I went up to be transformed back into Nigel to go home. I kept on my underwear apart from the bra, and just put on a T-shirt and trousers. With the jacket back on and my wallet retrieved from the handbag, I took the dress and bra and breasts in a holdall and got a taxi.

It was late when I got back, but there was still time to tell myself the story. On with the bra, tits and dress. This time there was no nightdress. Off went the dress, down came the knickers and I was being fucked, not by a phantom cock but by Jeremy with no regrets! I hoped he was wanking and thinking of me.

Friday really dragged. Of course, Amy and me were desperate to discuss matters, but work was in the way, and particularly tedious and annoying it seemed to us when we spoke at lunch.

We restrained ourselves on the bus, but found we were holding hands. It had been agreed that we would go back to my flat and I would change, as it was Nancy that Amy wanted to hear from.

She insisted I put makeup on as well, which I did rather badly while she made coffee. I had the grey dress and my new tits, but just panties and no stockings.

I was then forced to say almost everything I could remember about the meal including the fact that I had not brought the book and that he had had an erection, which caused her to hoot "Result!"

She looked serious.

"There are two questions here, both important. How do you feel about Nancy and how do you feel about Jeremy?"

I thought carefully.

"Yes, I want to be Nancy. And yes, I want to see more of Jeremy."

"And...?"

"All right, I want to have sex with him!"

"Attagirl!" she exclaimed.

"If he wants to," I added.

"Of course he wants to! Unless that stiff cock meant he was lusting for the waiter! Now there's only one more dress, full seduction outfit, and I suggest your place, which means you had better do some serious tidying and cleaning, young lady!"

"By the way, he is very good looking, so I am not surprised he has had success with boys and girls. Which raises the question: is he safe? Has he picked up something? I suggest you have some condoms and insist he uses them, no matter what he promises you. You might ultimately go without, but not just yet."

Fortunately it was not long before he phoned, to thank me for a lovely evening and when could we meet again. He was very pleased to hear my suggestion of a takeaway at my place.

CHAPTER 11

It was Friday evening, to allow the possibility of him staying over if things went that way. The flat was spick and span (or at least cleaned up as well as I could) and I had been seriously put into seduction mode in the flowered dress. I felt just like before an exam where you haven't prepared (if you know what that is like), and nervous as a kitten. A very nervous kitten.

So when the doorbell went at eight o'clock I ran to the door and opened it, trying to look the picture of loveliness, and saw my neighbour.

"Sorry," he said. "I was going to ask Nigel round if he wanted some grub with us, as we seem to have got rather a lot. You're welcome too, of course."

"We're all right, thank you," I squeaked, aware of my blushing face.

Five minutes later Jeremy turned up with the takeaway, and asked me why I seemed upset. I told him and we both ended up laughing. From then on things went very well.

He admired my dress, and I pulled it up to show stocking tops.

"Wow!" he said. "Stockings and suspenders! Aren't I the lucky man?"

Then I spilled noodles on my dress, and in rushing to help me, he spilled sauce on his trousers.

I went to put the dress in soak, washed the affected area of the trousers, and hung them up in the bathroom to dry. I put on a nightdress, while he continued in his shirt and underpants. It was proving a disastrous but funny evening! He was, of course, getting a good view of my sexy underwear.

"When do you think my trousers will be ready?" he asked with a smile.

"Not till morning," I answered.

"Then I'll have to stay the night, unfortunately."

"You're welcome to the sofa," I said.

"Unless you'd prefer the bed..."

We had to digest, of course and there was time to talk, but also cuddle and have little kisses.

This was also the time when I had to mention the condom word. He said he had brought some for today, but we might discuss it in future if we had a future.

Finally I went to the bathroom to prepare and returned lubed and ready, also nervous. He also paid a visit and then we played out my fantasy story, or nearly did. Thinking about today, I had imagined taking down his trousers (but that had already been done), then taking his cock out of his underpants, before lying back to offer myself.

He came out of the bathroom naked, so no getting it out of underpants. This was something I had never seen in my life and, in fact, just the sort of thing I had not wanted to see in porn. A large naked man with an erection. I didn't know how it compared to average, but it looked big to me. I took it in my hand, something I had literally never done before. We stood and kissed while I held it, and decided this was a nice feeling. I didn't envy him or feel sad for myself. On the contrary, I was glad with what we each had. I bent down and kissed it gently, but did not suck it.

He asked me to put a condom on, but I didn't know how, and had to watch him do it.

I went to the bed, pulled back the covers, and took off my knickers. I lay back with my nightdress raised and parted my legs, ready for him to enter. He came over, but instead surprised me by kissing my clit! Fortunately I had not lubed it! But of course, we both knew what we wanted, and he positioned himself above me. He took his cock in his hand, and rubbed around the lube before guiding it in. We both stayed still for a while, then he started moving gently. It was simultaneously both the same and very different from my dildo. Of course, I was not controlling it, I could feel some of his weight as he thrust and I could see his face and body above me. It could not have been further from the phantom cock, but so much better. I was filled up as I had wanted to be and knew I wanted to be again. And again. And again, and again!

It did not take as long as most of my sessions and I did not come, but I did not care. It was wonderful to feel him jerking inside me and seeing the expression on his face.

I couldn't help it. I said "I love you!" and I did.

"I love you too," he grunted before collapsing on his elbows. I was happy to feel some of his weight, though not too much, and held him in my arms.

Eventually he pulled out and went to the bathroom.

"Stay there," he commanded, and I did.

He came back without the condom and his washed cock half limp. I opened my arms to welcome him, but he did not come to hug. Instead he went down again, inserted two fingers into me and started sucking my clit! I think those fingers were massaging my prostate as he licked and sucked me to coming! He swallowed it all, and licked me clean.

"I do love you," he said again. "I really do." And we kissed again, with a few sperms on his lips, but I didn't mind.

Then we hugged.

"Do you think you could take that underwear off?" he asked. "Suspenders are very nice, but not ideal for sleeping!"

I went to the bathroom to wipe myself clean, and came back in nightdress and knickers.

"Take those off as well," he ordered. "All I want is you in the bed."

I must have looked taken aback, because he continued.

"I love you, the person, not the name, then gender or the clothes. And I'll love you in trousers or a dress just the same, and I'll make love to you dressed or undressed any way. But I know you like to be feminine, and I'm glad to enjoy it with you. I'll buy you pretty dresses and sexy undies and be proud to have you as my woman."

It only took a moment for me to realise what to say.

"And I love you for the man you are and the woman I am today, and not anything we both were in the past. Let's forget all that and just concentrate on being nice to each other. But I would like some new clothes!"

As I snuggled down with a naked man for the first time in my life, I had a thought. I texted Amy "We're in love!" and switched off the phone.