Magic Dress - Yvette Pt. 03

If I was truly to be a woman, it could not just be at home, so we started venturing out. The first time was just a walk down the street and back again. I wore trainers as many women do, the original dress (of course) for good luck, and a coat as it was quite cool. I was shaking, but managed. Slowly we increased the time and range of our adventures, but always together. I was of course terrified that someone would recognise me.

Then the big one. "We're going shopping!" said Kathy brightly. "We'll go to town, look at some clothes, have lunch in a department store café, and get you some shoes. A good girls' day out. What could be nicer?"

We took a taxi and strolled around the pedestrian shopping area. I saw a couple of people I knew, but they did not seem to recognise me. Then into a department store looking at clothes. We each tried on a couple, but did not buy anything. (We still had to be careful with money.) The cafeteria was fairly crowded, mainly with women. We had lunch and chatted like anyone else. We went to the Ladies' toilet together. Then to the shoe department, which was a different experience compared with being a man.

We first looked through lots of high-heeled and expensive shoes, while Kathy made comments and I nodded, yes they were nice, but was mainly baffled. An assistant came to ask if we needed help, and Kathy suggested we were measured. (I guess I did not fool her, but a sale is a sale.) Then Kathy said that we spend a lot of time on our feet and could they recommend some stylish but low-heeled ones, and not too expensive, please. After being provided with a lot, Yvette bought a pair of black pumps and a pair of sandals, and a pair of peep-toe "mid heel" ones which looked a bit high to me. All of them went on my feet and I was able to stand up, but I did not risk walking in the heels. Kathy paid with her credit card (as mine says 'Mr' on it).

One day Kathy said "Yvette, I've fixed you a date. This Saturday, dinner at a restaurant with a man."

"What!" I could scarcely believe my ears. "A date? What are you trying to do?"

"It's all right. It is just a nice dinner with a man and a woman having conversation. But you'll be on your own and have to act like a lady - especially with the toilets, of course! Don't worry. He's gay and used to men in drag. You'll probably get a kiss and a bit of a grope, but no sex on the first date. You don't have to convince him you're a woman as he knows: just seem unremarkable in a public place."

"This is all part of the experience of being a normal woman. I'm not expecting him to marry you, just for you to know what it feels like from our point of view."

My arguments fell on deaf ears, and anyway I was excited as I was fearful. Saturday came, as did my frequent need for the toilet. I was shaved and my fingernails and toenails painted. She gave me my final instructions. She showed me his picture again. His name was Simon, and I think any man or woman would have described him as quite good looking.

"This is a girl and a boy on a first date. They think they like each other, and if it goes well you will accept his suggestion of a second date. You will also let him kiss you. These days that means with tongues and you will hold him close. With luck you will feel his stiff cock. We hope he does not feel yours. But if he does, that's OK, he will not be alarmed. Remember your answers to his questions are what a woman would say, so be limited with your old chauvinistic experiences, and don't say you like action movies. We've watched enough girly ones for you to be able to discuss them. Don't drink too much and don't eat too much. Above all, don't ask your way to the Gents'!"

I was in the lucky dress, of course, and had my new pumps. I was hesitant about going alone in the taxi, but managed it, giving him £10 for the £8 fare and saying "keep the change". "Thank you, miss," was a nice response for me.

Whatever my performance, Simon's was perfect. He was a gentleman, starting by holding the chair for me to sit down, and he stood up when I went to the toilet (yes, the Ladies'!) I pretty well relaxed with the conversation and two (but only two) glasses of wine. He said how nice I looked and admired the dress. I found myself patting my hair and putting my hand to my face with the compliments, and quite enjoyed his gentle conversation. I actually volunteered very little about myself, but listened carefully as he described his work and outside interests.

When it was over, I made a last visit to the Ladies' to adjust my makeup while he paid the bill. He said his car was not far away, and he would drive me home. On the way to the car he stopped and said "Yvette, it's been a lovely evening, and you are a lovely woman. May I kiss you?" I nodded and he held me close. He was a jolly good kisser! He was much taller than me so I sort of lay back a little in his arms, looking up at him and closed my eyes, giving myself up to the lips and tongue possessing me. I definitely felt like a woman on a successful date. His hands stroked my back and my bum, but I did not resist. He pressed me close and I realised there was a big stiff cock pressing into my belly. His hand came down and patted my limp one. "Good," he said.

We got to his car and he drove me home. At the entrance we embraced and kissed. He said "I will wish you good night, but Yvette, will you please come on a date with me next week?"

"Yes, Simon," I said, and kissed him. "In that case, I have a little present for you," he said and went back to the car for a little packet. "For next time," he said and gave me final kiss before waving and getting in.

Apparently Simon had texted Kathy several times, so she knew the score. "Well done," she said as she kissed me in a sisterly fashion. "How did Yvette like her date with Simon?"

"It was lovely," I said. "Thank you, I really felt like a woman. But should I go on another date?"

"Of course," she said. "Every week for a while, and on the third or fourth one, he is going to fuck you, depending on how well you get on." I was incredulous.

"What?! I thought we were going to get married, and you have arranged for a man to fuck my arse?"

She hugged me and said soothingly "It's OK to have sex with several people before you get married, but in your case, we had better find out what Yvette really wants. Perhaps she will prefer sex with men to sex with women. Perhaps she won't want it at all. The only way to be sure is to try it a few times."

"Like women do," she added.

I was confused. "Is he gay or what?"

"Technically he is bisexual, and according to the texts he really appreciated you as a woman. There are quite a few men that have sex this way. Of course, you don't have a vagina, so he will use the only hole you have, and we must get in some practice first, so that it doesn't hurt. We have three or four weeks to get you ready. We can make a start now."

"A start at what?"

"Getting your little bumhole ready for his great big cock. By the way, did you feel it?" I nodded. And was yours stiff as well?" I shook my head. "Oh well done! We can treat you like a woman, not a man that gets excited from women's clothes. I thought you were, but it's good to check. Which reminds me, did he give you a present?"

I held it out and she opened it. It was some sort of stretchy pants along with some medical tape. "This is called a gaff," she explained "and it is used to hide your bulge. We will check it later, as you might not manage it. But for now, let's work on getting you ready for Simon's cock. Take off that lovely dress and knickers, but keep the rest, as I want you to remember that you are a woman. It is a good job we chose holdups rather than tights."

We went to the bedroom, and she asked "You went to the toilet a lot beforehand, because you were nervous. That's probably good. Do you think you are empty?" I said I thought so.

I noticed there was a towel on the bed and some bits and pieces. She put on a rubber glove, and got some lube. I knew what was going to happen, but she told me anyway. "I'm going to put a finger up your bum, and we are going to practise till you can relax it. Try not to resist."

Obviously I tightened up, but eventually we managed it. Gradually I learned to relax and she was able to slide in and out, which she did for quite a while with lots and lots of lube. I got used to it and it was not unpleasant. "See," she said. "It's quite nice. Now if you were a man, I would be trying to stimulate your prostate, but as you are a woman we will just concentrate on the hole."

"Now I think most women have anal sex at some time, and many enjoy it a lot. It is only right that if you are to be a woman that you should learn how to do it, and it would be best if you tried to enjoy it. As a straight woman, that is, not a gay man. It's good that you have practised with a butt plug. We will find the largest you can take. You must practise, and we will work our way up." There was a set of three on the table, the largest one looking very intimidating.

The first one was slightly larger than my tampon one. "Don't push against it. Try to pull it in." I tried and had a sense of triumph as it slipped in, the narrow neck holding it in place. She got me to get up and walk around until I was used to it.

"Good girl, Yvette! You've done really well. Now leave it in and go and clean off your makeup and have a shower. Your favourite nightie is ready." I did and asked if I should keep it in for the night. She said no, that was enough for the first time, but I would be spending time with it tomorrow.

We got up late on Sunday, but it was not to be a day of rest. Kathy inserted the next butt plug which was a bit painful and I wore it while I did some chores, cleaning the bathroom, sorting washing and so on. Moving around physically being the idea. I was aware of it, but it ceased to bother me.

"That's enough for now," she said and took it out. "We have got a couple of weeks to prepare your love hole, but only a few days to make you presentable for Simon. It's time to try the gaff, and here I can't help, you will just have to read the instructions and see if you can make it work. Some men can, some can't, apparently. It's no shame if it does not work, but you should try, that's why I gave him your size."

It was a prolonged and at times painful experience, which would have seemed very funny to any outside observer. I had to push my balls back into the cavities from which they came. I wasn't aware that I had such cavities, but found I had. Surprisingly, they went in fairly easily, but it took me many goes with adhesive tape to secure them so that they did not come out. Then I had to bend my cock backwards between my legs. This effort stimulated it to grow, so I had to wait for it to go down. Standing in a draught helped. Then I wrestled the pants on and bingo! No male genitals!

"Great!" said Kathy. "Now get dressed and put on some makeup. We'll see how you get on for the rest of the day. Now remember. You are a lovely woman. You haven't got a willy, so there are some more clothes you can wear."

"What about the toilet?" I asked. "Don't know," she shrugged. "That is for you to find out." Which I did. In summary, it was going to be bloody difficult in a small cubicle, and I would be advised not to drink too much liquid.

On Monday when I came home from work, I put in the butt plug for an hour or so, and the gaff for the rest of the evening. It was a big relief to escape from both of them into the freedom of a nightdress. On Tuesday, I wore the plug and the gaff together for a couple of hours, and the same on Wednesday. On Thursday we took half a day's holiday. She gave me a wank, to drain me, I put on the gaff and we went shopping for a dress. We came home with three which all required a smooth front, and which had looked good in the changing room. I felt so good as I posed and wiggled about, and Kathy said what a sexy woman I was. I was glad I had lost some weight. The original dress was now a bit loose on me, but I still liked to wear it. By contrast the new ones fitted closely.

On Friday we managed to get the third butt plug in, which was a triumph, and I wore it while we decided which dress to wear on Saturday. Kathy made a small adjustment for an even better fit. I was no longer nervous, but really looking forward to it.

On Saturday she insisted on wanking me off in the afternoon to make sure. I was so excited as I walked into the restaurant, and Simon was pleased. "What a lovely dress!" he said, "And what a gorgeous woman you look in it. I gather you liked my present." I said that I did.

The meal was good, both food and conversation, but then I got a surprise. "Let's not bother with dessert and coffee," he said. "I'd like to take you dancing." Oh.

"I'm not very good at dancing," I said.

"Nonsense!" he said. "It's not ballroom, just swaying about to music. Anything you do more than standing still will look good." These are the sort of things which make it worthwhile being a woman, and I almost forgot about my differences. Then I had a thought.

"Is this one of these LBGT places?" I whispered. "No," he said. "You don't need a place like that. It's just a normal dance club, though all sorts go there."

We got there and there was a queue, so we stood at the end. Then came a really happy moment as a bouncer looked me over, and motioned us forward to the front. I was considered a beautiful woman! (Later I realised that he was probably a friend of Simon, but I never asked.)

Well, it was crowded and noisy, with lights flashing, so what I did probably did not matter. However, Simon moved with grace and elegance, and I tried to match him. As it was hot, I made the mistake of accepting a drink, then discovered one of the drawbacks of being a woman - the long queue for the Ladies'. I was bursting and my cock stiffening with the effort of containing it before I got into a cubicle. It then took me a long time to get the gaff back in place as one of my balls had come free. Half the tape had come off with my sweat and the rest tangled, so I had to manage without it. It still wasn't perfect and I felt so guilty when I finally emerged.

"Time of the month?" said the girl hopping up and down outside, before rushing in. (I decided that I was only going to wear a gaff for limited periods with dresses which really needed it.)

The played some slow music and couples started smooching, as did we. I enjoyed his body as we moved slowly together, and he pushed his erection into my not entirely smooth crotch. "Like to come back to my place?" he asked.

"Sorry, not ready for that," said. "But next week should be OK." So the die was cast. I had set a date to have sex as a woman. Kathy was delighted, but said "We have got to get you ready. Butt plug now, then shower and we will make a plan."

She tried pushing it in and out and said "You're doing really well, let's try a vibrator, and see how that goes." She took a smooth and pointed one maybe a little bigger, and with lots of lube and the vibrations it was soon sliding in and out. I was pleased with myself and quite enjoying the sensation.

"Excellent!" said Kathy. "You are nearly ready to have sex like a woman. Simon is going enjoy you, so I hope it is good for you. Now let's get some sleep."

On Sunday and every evening we carried out the task of getting my rectum clean, which I will not describe to you. "Men may accept a bit of brown from a bum, but vaginas should be clear of poo. You are a woman being fucked, not a man being buggered. Remember that." By Saturday we had the technique right. By the time I was ready my new cunt was well washed and had been treated with a very large dose of lubricating jelly. The things a girl has to do for a date.

Meanwhile, Kathy had got a harness and a couple of strapon dildos, a medium one and a large one. She had never done anything like this before, so we made a comical pair. They were flexible so didn't go in well with her inexpert thrusts, but we finally got the technique and I was fucked (or rather pegged, as it is called) with the medium one each night. My cock expanded a bit and dribbled, but thankfully did not go rigid. By Thursday I had the larger dildo and a celebratory drink. Heaven knows what my performance was like at work, I was so distracted.

Well, I enjoyed being pegged, there is no doubt, though Kathy found it hard work. She could only manage ten minutes at a time. We did it from the front in the missionary position, which she found most difficult of all, and from the rear with me standing. Yes, I enjoyed it, but as we were not trying for my prostate and I wasn't thinking that way, I did not come. Of course I didn't have a clitoris, so there was no chance of a real female orgasm, I realised a little sadly. I was also a bit distracted.

Darling Kathy found something online and it fortunately arrived on Friday. It was a sort of combination of a suspender belt and thong, with a lacy front panel to cover my male bits. But instead of a single string, there were two, one on each side, leaving my butthole unprotected. I wore the gaff over the lacy panel and strings but under the suspenders.

He had arranged to pick me up, and arrived on time. I was ready inside and out but not psychologically. Logically, I knew I could take whatever he pushed in, and I did not love him, so had nothing to prove. I thought I was being a silly woman, which actually pleased me. I was wearing one of the three dresses we had recently bought, but he had not seen; stockings with suspenders and of course the gaff. Legs, pubes and buttocks had had a final shave. I had tried the mid heels but not managed them by this time, so was in the sandals. He complimented me and ran his hands down my body and over my pubes and thighs and was evidently pleased. "A real woman," he said.

He took me to his flat, not the restaurant, as I had expected. "I'm a fair cook," he said, so I thought we could have drinks, dinner and then make love, if you want to."

Suddenly I had a better idea. "Why don't you make love to me now, and after dinner as well?"

He was surprised, but not unhappy. But first we kissed and caressed. I was Yvette preparing to be fucked and enjoying the man now holding me as we moved and swayed to our own music and kissed deeply and passionately. It was not long before I said "I think I am ready, Simon. Just let me go to the bathroom for a moment." There it was off with the gaff and tape, my poor abused penis tucked under the front panel, and I returned sashaying in as well as I could.

I lifted the skirt to show the stocking tops, suspenders and front panel, then turned to present my bum, thrusting and wiggling it.

"How would you like it?" I said in what I intended to be a sexy voice.

"That will do very nicely," he replied, patting my buttock and leading me to the bed, where I instinctively bent over.

He parted my cheeks and then began running his tongue down my crack, which was a surprise but not unpleasant. Then he began tonguing my hole, which was new and a bit exciting. Then his finger in and out and side to side, then two. I realised this was it. Not Kathy, helping me out nor bits of plastic, but a real man who wanted to fill me and pump his seed inside a woman!

I suddenly realised I had not asked him to put on condom, and stiffened. He said "Don't worry, putting on a condom now." Then he was pushing against my hole, and saying "Yvette, you are so beautiful! I am so glad you want me to make love to you."

And the knob was in. I felt an electric thrill, and slowly his full length was in. It was at least as big as the biggest dildo, possibly larger (or that may have been psychological.) He moved slowly. I was now a complete woman: in a nice dress, being fucked by a man! I went into a sort of serene state as he fucked me; as time went on going harder and faster. I was tremendously excited, yet sort of calm as my cock slumbered quietly and I luxuriated in the thrusting and the feeling of just being filled up. I could feel his balls bouncing on me, his hands gripping my hips and his breathing getting faster as I realised I was responsible for this beautiful lust. I felt rather tender towards him as I felt him shake and pulse and grunt and swear. I wondered if women generally do that to a man coming inside them - I hoped so.