Magic Dress – Serena


Note: The early part of this story can be found in Cream and Lace.



It was the biggest surprise I had ever had on a birthday, and it turned out to be the best birthday present of my life. My darling wife Samantha bought a dress for me.

To some extent it should not have been such a surprise. My brother Frank was staying with us, and he liked dressing up in female clothes, especially underwear. It got him really excited before he fucked Sam. I couldn’t get erect or ejaculate since having surgery and radiation treatment for prostate cancer, so I was glad to see her so sexually satisfied, and I loved my brother, so it was better him than anyone else.

It also enabled my wife and me to enjoy creampie eating, where I licked the sperms from her pussy. We had discovered this before my cancer, and now with Frank’s help we had this part of our married life back.

Although we had all three been together for sex at the beginning, we quickly separated the two activities. Frank and my wife would go to our bedroom, while I would stay in the living room. I did not need to see anything: I just felt happy that she was getting fucked. When a man in a dress came out of the room, I went in to find the love of my life lying naked on the bed with her hand on her pussy, like Venus in a classical painting. I would put my mouth close and put it to her lovely vulva as quickly as I could when she removed her hand, to catch all the sperms. Sometimes I would lie down and she would kneel carefully over me. And always I would lick and love her till she was quite clean and she had had a nice orgasm. Though we were nearly sixty, it was the best sex ever for me.

Frank was ten years younger, so still had plenty of spunk for us. He said he was not looking for any other woman.

Before this I had never really thought about men dressing as women. I knew it happened, but it had never occurred to me and I had never been interested. However, much the same could be said for creampie eating!

Seeing the great sexual enjoyment my brother Frank got from dressing up was quite a surprise for me. It was only something he discovered when he was about forty, so it had been a surprise to him, too. Seeing it regularly in our home, naturally I became interested. I also discovered what women did with makeup, seeing my wife teach him. For the previous decades it had just been something that women did while men were waiting or doing other things. At last I understood why it took so long.

I began to notice things. A woman in a short skirt with blue-streaked hair in a shop in town had quite broad shoulders and a voice which was not totally feminine. It was a techie store, so they were probably quite liberal with gender roles. There were other women I saw around which also made me wonder, and transgender characters seemed to be more common on TV.

I had honestly never considered putting on a dress or makeup, but reading online about crossdressers, tgirls, shemales and all the other terms, I began to wonder very vaguely what it was like. Not that I had any desire, just wondering what the fuss was all about.

I didn’t say anything, and I don’t think I showed anything. But there it was: for my birthday, Sam had bought me a dress. It was green, high cut and sleeveless with a pleated skirt. There seemed no harm in putting it on. After all, both my wife and my brother were in female clothes.

Of course, first of all there was underwear: knickers, tights and a bra padded with socks. I had to sit for ages while some basic makeup was applied, and was getting quite annoyed.

Then the dress.

For Frank this process would have resulted in him becoming excited. For me it was the opposite.

A tremendous feeling of calm satisfaction depended on me. Serenity – that was the word. I was serene. So that was what the fuss was about! Well, if every man who put on a dress felt this good, I am not surprised there are a lot about.

I must have been in some kind of trance, because I heard Frank say “Is he OK?”

“Alan, are you all right?” said Sam. Oh how I loved her!

“Absolutely serene,” I said dreamily. “In fact, call me Serena.” It seemed so obvious.

After that initial something – I don’t know what – feeling, I began to feel happy and lively. Sparkling was perhaps the word. How good the world was, how glad I was to be with these two precious people, how life was so worth living!


That green dress had exerted its magic spell. At sixty years old I had discovered the secret of happiness. Over the next few weeks, my main interest was in building up a female wardrobe.

Apart from work (where I was always cheerful), I spent as much time as I could in lovely women’s things. Why had I never had a nightdress before? Weren’t lace and satin just right for underwear? Wasn’t a dress or skirt better than trousers? Frank favoured stockings and suspenders, but they were not for me. I was not trying to excite men: I was just enjoying clothes for themselves. Bostancı Yabancı Escort And I was dressing as a sixty-year old, not some young woman with a fabulous figure. I could still have nice clothes, though. For both of us, dressing up was strictly at home, of course. We both had wigs to suit our characters.

I went back to the techie shop and browsed. The assistant in a short skirt was definitely a man. I noticed a tattoo on his neck combining male and female symbols. On the internet I discovered that it signified transgender. Good for him! Good for her, I supposed I should say. I wanted to say how I admired both her and her choice of clothes, but of course did not, and instead asked a bearded assistant to show me a gadget I didn’t want.

It went slowly, but over the next year things developed. In fact, Samantha developed the two female characters, but in quite different ways. Frank became ruder and sexier. She admitted that the contrast between his feminine clothes and his raging cock and male attitude was quite a turn-on for her. By contrast I found calm happiness in nice feminine clothes and ways. A serene sixty-year old woman in a secure marriage. Fucking was something I had enjoyed in the past, but not for now. No regrets.

Frank and Sam fucked whenever they wanted. However, once a week I was treated to a pussy well-filled with spunk. They often held off for a couple of days before to make sure it was a good load.

It is hard to explain, but it was a beautiful loving experience rather than a sexy one. I delighted in the fact that my darling wife was still so sexy and was being well satisfied by a younger man. My mouth full of spunk was proof of that, and the way she responded as I licked her clean was wonderful. She was already well excited so could easily give me the gift of her orgasm. I was in communion with this goddess, whom I worshipped.

We ended up with Sam sleeping with us on alternate nights.

I never went out, but was taught to act in female ways. We got some shoes with two-inch heels, and I became quite competent in them. Frank got four-inch ones, but could only totter about, as he only wore them in his preparations for fucking. My makeup became quite refined, his became more outrageous. He was always Frank even in a dress, but I was Serena when at home. But Sam and I were just the same as always in many ways. Frank was a lover, not a husband, that was clear.

Our birthdays were ten years and a few days apart, so Sam gave us our presents at the same time. Second best birthday present ever! They were realistic plastic breasts, quite wobbly with nipples. Mine were of a modest size and perfectly fitted the green dress. Frank’s were two sizes larger, and he was ecstatic with them!

I was also given some control pants which could make my cock and balls virtually disappear. The effect was quite good, I thought, so I might wear them if I ever went out. There was no need at home, of course.

Frank of course wanted nothing of the sort: he wanted to display his stiff cock to the world. He had to be satisfied with impressing me and Sam of course. He actually asked me if I would possibly give him a wank. Sam said it would be OK, but I refused. Not out of shame: I just did not want it.


Frank at last had found a job, actually better than his previous one. His regular sexual satisfaction seemed to make him more confident and even-tempered than he had ever been, so I think that helped. He started to socialize a bit with his new colleagues. He promised he would tell us if anything happened with a woman, but said he wasn’t looking except as window shopping. He thought he was getting the best sex he was likely to get with Sam, and it was unlikely that anyone else would appreciate his fetish.

I looked forward to retirement and being Serena full-time. I did not think my workplace would be very accepting, and there were some people there I was sure would give me grief.

However, Sam said I should start practising. I think my new breasts had given me a bit of a lift, and I sort of wanted to show them off, along with my skill in heels.

Finally, I was persuaded to go out. I put on the green dress but covered myself with a coat and did not have the wig. It was evening and Sam drove me to a housing estate with a few shops where we never went.

We parked and I put on the wig. Then out of the car with a nice female cardigan instead of the coat. We walked slowly to the shops, past them on to a little park and playground, which were deserted, and stood by a bench for a while. (I did not wish to risk dirtying the dress by sitting down.) So far so good!

We were both cheerful as we strolled back towards the car. As we were passing the shops a child came by on a bicycle on the pavement and we had to jump out of the way, knocking into someone coming out of the shop, a young woman. I nearly fell over, and she grabbed me to stop me.

Being English, we all three said “Sorry” and I recognised her as the man/woman Bostancı Yeni Escort from the techie shop.

“That Darren’s a bit of a menace,” she said. “Have you just moved in?”

“No, just visiting,” answered Sam, quickly.

“Well good night then,” said the woman.

She paused and looked at us.

“Do I know you?”

“We’ve been to your shop,” I said, forgetting that my male voice would be a giveaway.

She looked at me closely and I blushed.

“Oh yes,” she said. “But you’re usually in drab. You look much better this way. Have you been doing it long?”

“I don’t know what you mean,” said Sam. “We must be going now.”

“No, wait a minute. I’m Sylvia, by the way, but I used to be Derek. I transitioned a few years ago, so I know how you feel. Please come and have a coffee with me. I’m just round the corner.”

“Well…er…,” I mumbled.

“We’d love to,” said Sam, taking charge. “Do you live with your family?”

“No, just my boyfriend,” she said as she started to lead us. “But he’s out and won’t be back till later.”

The flat was on the first floor of a low rise, and was small but pleasant.

We accepted a coffee and biscuits, while Sylvia told us a little about her experiences. She had obviously been very brave, having been bullied but knew what she wanted. I simply said that about a year ago I had realised I wanted to be like a woman (I didn’t say be a woman, only like one) and how Sam had helped me. I did not mention my kinky brother or what we had done with my son.

She said she thought it was tremendous when older men decided to embrace their feminine side and she admired me. Then she made her sales pitch.

“Look, all I wanted to say to you is if you need any help, or just want a bit of company who will be sympathetic, there are quite a few of us. Most are just crossdressers, but some of us have gone a bit further. We just meet and talk and protect each other. Give me a ring. Here’s a card.”

We heard the door open, and she got up.

“Oh, that’ll be Chris. He’s early.” She went out and spoke to her boyfriend.

They came back together and she began “Chris, this is…” but was cut short.

“Mum!” he said. “What are you doing here?”


Samantha got up and kissed him.

“We were just passing by, and nearly knocked each other down by the shops, so Sylvia invited us in. This is my friend Serena.”

He nodded in my direction and said “Nice to meet you,” before turning back to his mother.

“Are you checking up on me? You don’t approve of Sylvia?” he said, quite angrily.

“No, no! She’s lovely. You should have brought her round to see us. Why didn’t you?”

“Because Uncle Frank would be there, and I know he would make something of it, and I thought you wouldn’t understand anyway! So now you know and I hope…”

His angry tirade petered out as he looked at me.

“What the fuck? Is that you, Dad?”

“Yes, son, it is,” was all I could say. He sat down, quite heavily. Sylvia said she would make more coffee.

It was quite a conversation that eventually followed, though rather hesitantly on both sides.

“What about Sharon?” Sam asked.

“We both moved on,” said Chris. “She was my first girlfriend and it was great, but not for ever.”

“People do move on,” added Sylvia. “I know Sharon and her brother Bob. Lovely people. She used to say what a great boyfriend Chris was in every way, and she was right. You’ve raised a wonderful young man, one who really knows how to treat a woman right.” She kissed him on the cheek.

“Thanks to you, Mum,” said Chris, and patted her hand. I wondered how much he had told people.

“Never mind about me,” he carried on, “what about you? What’s happened to you, Dad?”

“I think she’s Serena, now,” cut in Sylvia.

“It’s all right, you can call me Dad,” I answered. “As you know, I couldn’t have sex after the cancer, and your Mum thought I was acting a bit feminine, so suggested we try it. As always, she was right. I can’t really explain it. I didn’t choose, it just sort of happened, and I’m very happy like this. We didn’t tell you because we thought it would shock you. I’m sorry.”

“I think you look lovely, Serena, and that’s a really nice dress,” said Sylvia.

“Thank you,” I answered. “When I first saw you in the shop, I thought how great you looked. When I thought you were or had been a man, I really wanted to tell you how much I admired you, but I didn’t dare. I always appreciated your style every time I was there. I suppose you might have given me the idea somehow.”

Everyone paused.

“Oh,” said Sylvia. “I’m not sure if I should be flattered or not.” Then she gave a big smile and came over and kissed me on the cheek.

“So, Chris, what your Mum and Dad want to know is what about me. I’d better tell them.” She looked at him and they exchanged fond glances.

“I’m transgender. I have had surgery and hormones. Chris and I make love as a man and Bostancı Masaj Salonu woman.”

“I’m so glad for both of you,” said Sam, and she went and kissed Sylvia and Chris both. “Bless you for telling us. We couldn’t possibly ask, but were bound to wonder. All that matters is that Chris is happy, and you seem like a lovely girl.”

Sylvia seemed to be tearful, so said she had to go to the loo, and would anyone like some more coffee? No-one did.

While she was away, Chris came close and whispered.

“I haven’t said anything about you and me, Mum, and I never will. But you were such a sexy woman! Is Uncle Frank, you know?”

“Yes,” she whispered back. “He’s your Dad’s brother, so it does not seem wrong and we’re all happy with it.”

“That’s good,” he said and went back to his chair.

When Sylvia came back, he asked about me.

“So Dad, how is it being Serena? How much do you go out like that?”

“This is the very first time,” I said, “and I was scared stiff. It’s only been at home so far. But when I retire we might try it. I just feel so relaxed in women’s clothes, that’s all. I don’t think I’m any different apart from that.”

Sylvia said that was enough of that talk for now, so instead we all talked about our jobs and what we liked doing. Just being introduced to our son’s girlfriend. The more we talked the more we liked Sylvia and the happier we were for Chris.

After a loo break, we departed, promising to get together again. I kept my wig on and did not put on my coat.

Back home I walked as Serena all the way from the car. I was exhausted when I got in, but what a thrill!


Chris and Sylvia came round for dinner, while Frank made himself scarce. Sam and I were both in nice dresses, while Sylvia was in a very modest knee-length skirt and top, and Chris was well scrubbed. All trying to impress. We complimented each other on clothes, and of course the meal.

Eventually the conversation turned to other things.

“Chris has told be about your brother Frank,” remarked Sylvia. “I wasn’t shocked. I think it’s lovely, and so nice of you, Serena, to look after Sam in this way. I hope I can meet Frank some time.”

Sylvia told me of some shops where they were happy to measure and fit men for female clothes and would be discreet, and gave us a contact for a seamstress she used herself for alterations. We were also introduced to some other couples like us of a similar age.

Next time Frank was there in his regular clothes. He was a bit uncomfortable, but Chris said he thought our arrangement was wonderful, and he was so happy for Mum and Dad. (He never called me Serena.) Sylvia said she liked to be a bit outrageous and begged him to let her see his glamorous outfit some time, so another date was agreed.

Beforehand Frank was nearly panicking. I didn’t see it, but Sam tried to toss him off beforehand and failed. Unusually for him, he just couldn’t get it up. Sam moderated his makeup, but he did look like a man in drag, with a frilly dress and his large boobs, moving slowly in high heels.

Chris was wide-eyed and open mouthed. Sylvia put her hands to her cheeks and said “My God, you look fantastic! You really shouldn’t hide that glamour away!”

She walked around and looked him up and down from every angle, making approving sounds.

“Go on,” she continued. “Show me what’s under. I know you’re dying to.” He put his hands down to cover the front of the dress, but Sam and Sylvia looked at each other in a conspiratorial way. Sam moved his hands away and lifted up the dress.

There were stockings and suspenders – and a cock straining and peeking out of lacy knickers!

“Wonderful!” exclaimed Sylvia. “You look so hot! No wonder Sam fancies you! There’s a lot of women who would go for this, and a lot of men who would envy you. You really should share this with the world!”

“Would you excuse us for a few minutes,” said Sam, and took him to the bedroom.

When they came back everyone was smiling, though no-one said anything.

(Sylvia did actually take Frank to a club, but it was a bit of a disaster, apparently. He got lots of compliments, but also offers from gay men to fuck him or be fucked by him. This was not something he wanted at all.)


It was bad news, the consultant said. My cancer had evidently not been completely eradicated. He was afraid that the safest course of action was to reduce my testosterone levels. He supplied some leaflets and made an appointment with a counsellor, to discuss the side-effects.

At the next consultation, Sam and I surprised the counsellor. We were not afraid of the possible feminization that might result. My medical records showed I had not had any erection enhancing drugs for two years, and we said we had given up on sexual intercourse for the same time, because of the loss of sensation following surgery and radiotherapy. I would simply be glad to lose any residual desire which I could not satisfy.

In view of my age and our expressed preference, a simple treatment was orchidectomy (the removal of my testicles). I was offered fake ones to be put in the scrotum for appearance, but declined. Some medication would be required afterwards, but not as much as if I was still making testosterone. We required no persuasion.

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