Magic Dress - Emily Pt. 04

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Martin and Martha and more.
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Part 29 of the 82 part series

Updated 06/09/2023
Created 02/01/2019
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CHAPTER 12

I guess we rather mellowed for a couple of years. No-one dominated anyone very much. I sucked and was fucked by Robert, though less often. Emily did not have sex, but was out more and more socially and was happy. We enjoyed our weekly dancing, after which I secretly lusted after Jason.

It was Lucille who initiated the next chapter in our lives. She invited us over for dinner and to meet someone. We were introduced to a young person, who had entered university as Martin, and come home with a degree as Martha. Her parents had thrown her out. She had early on been helped by Lucille's Ladies' Walking Club, and came to them.

"Look," said Lucille. "I think Martha would be much better off staying with you than with us. She's a heterosexual man who just likes dressing up. She doesn't want to transition or have sex with men. And she's a virgin, so needs protection and some help to change that. Robert and Emily should understand."

We took her in, and I was reminded of Shakespeare's play Twelfth Night "Some are born great, some achieve greatness and some have greatness thrust upon 'em." Looking at our new household, I can say Claire was born feminine, Martha achieved femininity, and Emily had femininity thrust upon her.

Martin and Martha interchanged quite easily, by which I don't mean that they magically looked quite different, quite the opposite. It was just that with the face, slim build and medium length hair, plus the large glasses, you could believe either sex. In loose casual neutral clothing, you would probably not be sure. Perhaps this was part of the reason Martin had as yet no success with girls. In stereotypical female clothing (which she liked), you would just assume a woman and treat her as such. Her voice was soft and not deep. On the other hand, if your first impression was male, then Martin seemed quite natural.

Like many young women today, Martha did not wear high heels, just trainers. I told her a woman has to have several pairs of shoes, so took her to our special shoe shop to get something smart but practical for the office, another with a slight heel for evenings out, and sandals as it was summer. She understood these things no more than Robert or most men, so appreciated the help. (I think - or was I just being a bit controlling? Good either way.) The assistant seemed surprised to see me with what looked like a woman, but was happier when she decided that it was a man, complimenting Martha on how nice she looked and quietly to me how well I was doing with him. She was surprised that Martha did not want any heels, and managed to persuade us to take a pair with kitten heels. Actually, with a bit of practice, Martha quite liked them. I paid, of course.

I took Martha to my favourite brassiere fitter, and she was well pleased with the comfort of the bra set suggested, and took the larger of the two cup sizes proposed (as expected). We later paid for some breast forms which even got a sincere thank you.

We had never had children, so in one way, Martin and Martha were like a son and daughter to us, being somewhat exasperating, thinking they knew it all, and getting us to pay for things. Two for the price of one.

Martin's good degree in sociology resulted in an office job in local government, where they were happy with the situation, and accepted Martha as the working name for their new employee. However, Martin was not presenting anywhere as a man, so had little chance of finding a girlfriend in the usual arrangement. Nevertheless, he was a hormonally a typical young man who masturbated every day. (Morning and evening, we found out quite soon.)

Martin/Martha and Robert/Emily were fascinated with each other and their opposite experiences, though sharing the same beginning as randy men.

Finally, it was Robert who came to see me. There was an obvious solution to Martin's virginity, but first he wanted to speak on behalf of Emily. It was a long shot, but just suppose Martin might like being sucked off by Emily? Emily would really like it, if it was possible.

You may not understand it, but we really were bound by Jason's commands. Some sort of self-hypnosis, I suppose. Thus I could only have sex with Martin if ordered by my husband, and Emily could only do the same if ordered by me. Neither could offer ourselves to Martin, and we really were not sure. We felt we had a duty to help this young person start their sex life, but perhaps it should not be with a couple old enough to be her parents, and we should not take advantage of the situation for our selfish pleasure.

We telephoned Lucille, who said that she had just expected us to introduce Martin to some nice understanding girls, but it might be a start to get his confidence up. She apologized as a gay male she was perhaps not the one to ask. However, she agreed to come over and arranged a time with Martha next evening.

Lucille came as Luke and spent more than an hour in Martha's room, before coming to tell us. Emily was wearing the lucky green dress in anticipation.

"The bad news is that Martin is a typical shallow young man who thinks you two are far too old to fancy. The good news is that Martin is a typical shallow young man who is desperate to get his rocks off. I told him a mouth is a mouth, and he has agreed to be sucked off by both of you and to fuck Claire. After that there may be nothing, or it will be for the three of you to negotiate. He is sitting there with a raging erection which he will toss off unless someone goes up quickly, which I have decided should be Emily. He will be unable to refuse because he is so desperate, so now is a good chance. It will probably not take you long, but is a start. Then this evening he is expecting you, Claire, and I suggest you actually stay the night to give him the full experience."

I looked at my husband. "Go and suck him off," I said, and upstairs she went. Meanwhile, I took Luke to task.

"What the hell did you mean by telling Martin he could fuck me?!"

"Well," he said, "You don't have to, but I thought you probably would, just to give him a start. I know how much you fancy Jason, but unfortunately I can't offer him to you. I thought maybe a young man half your age, might just appeal for a change. Perhaps you can think of Jason. Do note that your husband did not object. I think he rather likes the idea."

"Well!" I said. "If you think..." but rather ran out of arguments. "OK, just this once."

Meanwhile, Luke told me some more. "Martin is intelligent but shallow, and the same applies to Martha. She is just a woman on the surface: there's no depth to her femininity, unlike Emily. I suspect it started as a trick by Martin, being able to fool people so easily, and of course feeling a bit outrageous by going against society's norms. I don't think he's ever going to transition, unless he meets some young woman like Gladys, of course!" We both laughed.

Emily reported that the encounter had been short but sweet for both. He had an average size cock and was otherwise unremarkable.

It was unusual for me to spend so much time getting ready for bed, and to be wearing makeup, but I was to be a girlfriend with a boy losing his virginity, so did my best, including my sexiest nightdress and panties. Which were soon to be removed, of course.

"Go and have as much sex as you want with Martin," ordered my loving husband.

Martin of course was already stiff and ready to go, but I told him he had to treat a woman right, kissing and fondling me. I held his cock, which was a pleasant size. It was all nice, and I would have liked more, but he was so desperate that I relented very soon. I lay back in what I imagined was the glory of my womanhood (who am I kidding?) Well, I had boobs and a cunt and I was there. My vulva proved slightly more complex than he had appreciated, so it took a couple of goes before he got it right. Then I thoroughly enjoyed his inexpert thrusting until he came and collapsed on me. Since he had been sucked off earlier, it wasn't too short, though he didn't come very much, which was to be expected.

Eventually the lack of breath made me push him off and out. I wiped myself with a tissue and sucked his cock clean, which was nice, and surprised him. We cuddled a bit; then I went to the bathroom for a wipe with a flannel. When I got back he was asleep. I was quite touched. I had to move him a bit to get in, and settled down. Eventually I went to sleep as well. During the night he put his head on my chest, which I also felt was touching.

It was just before 6 a.m. when I heard the immortal words "Are you awake?" traditionally used to wake someone up. Sleepily I allowed him to mount me. It was longer and better this time. Immediately afterwards I kissed his cock and his cheek (wishing to avoid morning breath) and got up.

Martha was very cheerful as she went to work, and who could blame her? So was I, having been fucked twice by a man half my age, so who could blame me? Rob said he was pleased for both of us, and Emily had had a good time as well.

Naturally, Martin thought he would be fucking me all the time, so was disappointed when I explained the situation that evening. In short, I was in charge. As the owner of the sole cunt in the house it was my choice who got to use it and when. My husband was the priority user, but Martin could be a guest as and when it suited me. I told him this was an important lesson for future girlfriends. That is why men had to be nice and respectful to the owners of these magic organs, and accept that it was a privilege not a right to be allowed to enjoy them.

I said he would probably still have to toss himself off most days, but Emily might be surprising reasonable in providing an alternative. Of course, if I preferred to suck him off that is what I would expect.

Yes! I was controlling a man again! (With only a tiny bit of humiliation - honestly, hardly any, just making sure he knew his place.)

The next months were frankly wonderful. I had a vigorous new lover to train up in the nicest possible way, plus of course my loving husband and two female companions. Having trained Robert to be a woman, I was now training Martha to be a man. I said that on any evening when he hoped to have sex with me, I wanted to see Martin as a man. Thus quite often Robert came home and put on a dress, while Martha came home and changed out of one. I insisted he was a little bit smarter, as a boy wanting to impress a girlfriend might be. Our lodger had a bedroom, not a flat, so we were rather like a family, though an incestuous one, I suppose.

Martin's limited copulation meant that he soon started to ask Emily for relief, and discovered that although she was in principle pleased to swallow his sperms, it was also not a right, and he needed to be very nice to her.

My use of the vibrator was greatly reduced, though I occasionally refused both Martin and Robert for several days, but made sure they heard me using it. Just to keep them on their toes, and remind them who was in control. Otherwise Robert my husband fucked me as often as he wanted, and Martin was limited to the gaps in my diary and my personal fancy. But I did get fucked a lot, so I was not being hard on anyone.

Yes, I was a controlling bitch, but I had a plan with good intent. Eventually I dropped the bombshell. Emily also needed to be fucked, and Martin had to do it if he wanted to continue fucking me. Of course, Martin would have to wear a condom, which was good practice for any future sexual partners. We were in a special situation which allowed free sperming, but he had better not assume that was generally the case. I had been training Emily with dildos, and she had found it very pleasant, so had become keen to enjoy the ultimate female sexperience of a real cock, enthusiastically applied.

Martin didn't want to, but eventually gave in and found it rather nice. Another man had been forced to do something against his will and learned to like it! (Admittedly it took only one fuck to convince him that this was an acceptable alternative, and better than self-release. However, I was still better than Emily, having the advantage of the genuine articles both down below and on my chest.)

Basically, if my husband fucked, sucked and was fucked enough to his satisfaction, then I was more than willing to let Martin enjoy me in his vigorous young way.

+ - + - + - + - +

CHAPTER 13

It was Martha's turn to drop a bombshell. I had to confess that I had been a bit remiss in our supposed target of young women for Martin to fuck. It had been a year now, and nothing had been achieved (unless you count the more or less continuous orgy in our household). Now he had got himself a date. To be precise someone at work wanted to take Martha out, but it was a man. And yes, he knew what Martha was, but still liked her a lot.

We called for Lucille. Who said of course there were gay men like Jason who liked men who dressed as women, Lucille being a case in point. The only issue was whether Martha would appreciate the sex between two men. However, going out did not automatically mean sex. Many lifelong friends went out to enjoy each other's company. On what was probably the third hand, it was possible that the new man would not want to fuck Martha but just be fucked, by a man in a dress. Sex is in the head.

I fussed over Martha like a mother, getting her ready for a big date. I was trying to reassure, but probably made her nervous.

When Martha came home, we were the nervous ones. She shyly informed us that it had been nice. They had gone to the theatre, had a glass of wine, held hands and he had kissed her. They agreed they would take things slowly.

The next day the person who came home was in Martha's clothes but was definitely Martin. It had been a dare. A photograph of them kissing had been the proof, and some guys were laughing at him.

I kissed him and said "Poor baby. Do you think a fuck would make it better?" He said no, but it would do for now. We went quickly to his room and I was treated to the most vigorous fuck of my life. I stayed with him. Robert eventually knocked and said he had made some dinner if we wanted.

We went down, ate and went back to bed. I told Robert I would be staying the night. I was fucked twice more. Yes, they were pleasant, but I was mainly feeling mother love in the release they gave him.

It was the weekend. Martin stayed as Martin for all of it. Martha had been spoiled. He got morose, but cheered up a little when Emily sucked him off. That evening, he asked could he fuck Emily please? We were his family, and it would sort of seem right if he fucked us both. Of course we agreed. He fucked us both on Sunday, but he still looked so down that Emily offered to suck him off in the morning instead of his usual wank. (It was just Robert with the wig, not the full gear.)

On Monday it was Martin who went to work. He didn't want to eat much when he came home, didn't want to talk about it and didn't want sex. The same on Tuesday, but he was sucked off in the morning. On Wednesday I sucked him off in the morning, which cheered him up a bit. In the evening he agreed to fuck me, but still would not talk about it. On Thursday, Emily started his day and he fucked her in the evening. I sucked him off on Friday morning. In the evening he came home really cheerful with good news.

The guy who had caused the problem had been transferred at the request of the female staff. They had also asked to have Martha back next week, and wanted to invite her to some girly outings. In addition, two girls had actually asked him out! They had supposed he was gay, but having commiserated with him over the incident discovered that he was not, but liked wearing women's clothes, which they thought was quite cool.

It didn't happen quickly, but he started going out with girls in the office and fucking them. He swore that he always used a condom: they would insist anyway because they all worked in public health. Sometimes they came home with him, mostly he went to their places. In a few weeks the score was five. Sometimes Martha came home and changed into Martin to go out with a girl. Sometimes it was Martha who went out with a group of girls. It seems none of his girlfriends wanted him exclusively, and he knew they went with other men. He said they had complimented him both on his sexual technique and the respectful way he treated them, so thanked me as his teacher.

My husband is now Emily except at work and on rugby days, but is talking about being Emily at work, and possibly dropping the refereeing. That means at the moment I get Robert's cock twice a week, which I suppose is enough. Emily loves me with her mouth which is of course lovely. Obviously, Martin doesn't fuck Emily or me as often as before, but it is still quite often. He does us alternately to be fair. Unless he has a girl staying over (which is usually once a week) Emily sucks him off in the mornings and is happy to do so. I sometimes do at the weekend (thinking of Jason).

I have been successful in training two men: one to be a woman, one to be a man.

I think Martin believes he is now the man in control of us two women, but we are quite happy to let him have this misunderstanding. We do hope (in a sort of parental way) that he will move out to be with people his own age.

+ - + - + - + - +

CHAPTER 14

It was about a year later that we received an invitation from Charles and Gladys for dinner in a very expensive restaurant. We saw two smart and well-preserved ladies. Charles was now Charlotte, with a trim figure and a good bust. Gladys had also lost weight and looked good for her age.

We told them how we now had Martin and Martha, but thought it would not last for ever, so we were enjoying it while we could. They were pleased to hear that Emily had been enjoying cock. However, Charlotte looked if she had fully transformed, and we were anxious to hear more.

"Well," said Charlotte, "you know that I started taking hormones. I liked being a woman so much that we decided not to wait until retirement but get on with it. I went to Personnel Department (or Human Relations as they call it these days) to say that I was changing gender, and therefore requested early retirement before it became too obvious. The Head of the Department, Gareth came to see me and I repeated my request. He was clearly shocked, and asked me to wait. After a while he came back and took me to the office of one of the directors, Max, where I explained my situation again. I apologized if my intention to change gender had come as a shock, as I had valued my employment and did not want to cause embarrassment."

"Gareth said the shock was not my change, but retiring early, as they had hoped to persuade me to stay on for a few years after the normal retirement age, and was there any way to change my mind?"

"Max said that I could be Charlotte and come in dresses immediately if I wished, just so that they did not lose me. I was quite surprised but said how much I appreciated the confidence."

"Gareth remarked that having a transgender woman in such a senior role would certainly tick a box for inclusivity, and might encourage other employees to be more open."

"The upshot was that I eventually moved to a new office and higher paid position, starting as Charlotte. I was just going to get my male bits removed, but Max said no point in doing half a job, and encouraged me to get a working vagina. It's quite clever how they sort of turn the penis inside out, so I get feelings, and I can even come!"

We were fairly stunned, but I began "So you...?"

"Yes I do!" came the reply. "But let Gladys tell you about it."

"This is about Malcolm, who now lives with us. He's a maths teacher at my old school. Nice lad (well, I say lad, he's in his forties) but rather skint after his divorce. We converted the children's bedrooms into a sort of apartment with ensuite facilities and a study to do his marking. I invited him to stay with us and have now got him fully trained."

12