Magic Dress - Toni Ch. 01

My name is Toni, with an 'i', though it used to be Tony with a 'y'. You would not think me a pretty woman, because of the face and frame from my life as a man. You would not think to look at me that I was a sexy woman, but I am. A woman and sexy.

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ABOUT ME

I was the eldest of four brothers in a bad family environment. My father beat my mother and his kids, often being sly about it. He would say he was teaching us boxing, which was an excuse to hit someone smaller than him. When I got able to defend myself, he moved to my younger brother, and so on. It was a relief when he died in a car crash, but put the family in a difficult financial position. I attended his funeral only as support for my mother who had suffered more from the beatings than I realised and her life was shortened. My Dad's sister was there and she told me she thought Dad had mostly been angry at himself for his own homosexual feelings.

I left home at 16 and joined the navy where I actually became a boxing champion. I also became a skilled technician. I loved the technical work, the physical activity and comradeship. I had some really good mates, in particular Steve, who became my best mate. As a very fit guy, it was not difficult to find girls to fuck, but my heart was in it less than Steve.

There were also some great women there, including Carol, another technician, who became a friend rather than a girlfriend. It was her who recognised something (though we didn't realise it at the time) when me and Steve were rather drunk and he had his arm around my shoulders. Steve was slurring "You're my best mate, I love you Tony," and Carol said "Oh you two! Get a room!" Which was a laugh, since Steve was clearly not gay, and I really liked women.

I didn't think I was gay either. If I saw a fit guy with his shirt off, I might think about what sort of exercises he was doing for his muscles and his likely performance as a boxer, not in bed. Now the naval community had gays, lesbians and bisexual people and was surprisingly tolerant. Many guys tried it, including me and Steve. Sort of as a dare, we agreed to toss each other off. We just said it was a laugh. We decided we had found out that we were not gay, which turned out to be correct. Many years later, Steve said he had been frightened how good it felt when I wanked him, but thought I was uncomfortable when he did it to me, though he desperately wanted to give me the same. I didn't enjoy it from him actually, more a feeling that it wasn't right, but quite liked doing it to him. But we never said this at the time. How could we?

After leaving the navy, Steve and I shared a flat. We wanked ourselves, not each other, and Steve sometimes had a girl round, though less often after a while. The fact was we liked each other, and we were a couple. Although I had stopped boxing competitively, we both liked keeping fit and went to the gym and jogging together.

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THE START OF THE CHANGE

It was the saddest day of my life: my mother's funeral. Of the four brothers, three were there. Freddy had flown over from Canada, but Simon was unavailable. I later worked out that he was in the middle of an operation with Special Forces. Jim, the youngest, had made all the arrangements.

Steve had driven me there, as I would be too upset. I spotted Freddy first and asked him where Jim was. He pointed, but all I could see was two women in smart black clothes. The one on the left looked at me and I saw her green eyes. It reminded me so much of my Mum, I guessed she must be some cousin of mine, so I went over to say hello. As I got closer, I got a shock. It was Jim. He was the only one of us to inherit Mum's eyes. And it was him. Or rather, her. "Hello, Tony," she said and hugged me.

It turned out he was what they call cross-dressing, effectively living part of the time as a woman but without any operation. I knew Mum had always wanted a daughter, and he/she said that in the last couple of years he had effectively become that daughter called Jane, and that is who Mum would have wanted at the funeral. I was crying, and Steve put his arms around my shoulder. I was so sad, and yet so happy to think that Mum had had her daughter even for a little bit.

We stayed the night with Jim/Jane and his wife Nancy. They only had one spare room with a double bed, so Steve and I shared it. No, we didn't have sex. But I started crying, thinking about Mum and he held me, as I sobbed. He is taller than me, six feet one, so it felt quite comforting to lie there with my head on his chest.

In the morning it was Jim, not Jane, and we talked about Mum and some of the happy times, and avoided mentioning Dad. Nancy explained how Jim had secretly been wearing women's underwear, and she had eventually bought him a dress, so now he was very happy as a man at work and a woman at weekends. She showed us the first one, which they called the magic dress, but Jim did not put it on.

After that Steve and I hugged casually at home, especially when I was upset thinking about my Mum.

Some time later we were walking down the street and Steve stopped.

"You know your brother Jim? Did you ever think about wearing women's clothes?"

"Sod off!" I said, because I didn't want to say yes and it would be a lie to say no.

"I have," he said. "Jim said it was very calming for him. I think I'd like to try it. Let's both have a go. It'd be a laugh, anyway."

"Fuck you, you great pansy! You can if you want!" I kindly replied.

We had stopped outside a small shop selling women's clothes which had a closing down sale. There was a man hanging clothes on an outside rail marked "Final Reductions £10".

"Hey, mate," said Steve. "Got anything that might fit us? It's for a party!" He was like that- he'd dare anything. Fucking crackers, that man!

The man looked at us.

"Well," he said, there are some for the larger lady here, though they might be a bit short on you."

He rummaged, and produced a yellow dress, just straight up and down, which he held against Steve.

"You tie it in with a belt," he said, "so your shape doesn't matter. Most sleeves would be too tight on your shoulders, so straps are what you need. Hold that a moment."

He went inside and came out with a large pink nightdress.

"If that doesn't work, a nightie will. You can wear it with shorts for the party."

I had to laugh. Steve in a pink nightie!

"That's so you!" I said.

At that point I could hardly refuse, or I would look chicken.

He went through the rack, and produced a flowery thing.

"I think your friend could manage this. Hmm." He held it up against me.

"Oh yes, a nightdress to be sure." He went back into the shop.

He came back with a blue nightdress and a green dress very similar to the one my brother had shown me, but a larger size.

"Fuck me!" said Steve. "That's a bit of a coincidence! We'll have to take it." I couldn't speak.

The man had a bag in his other hand.

"I took the liberty of bringing a couple of bra sets. You'll need them for the dresses to look right. There are a couple of extenders as well. You fit them at the back if the bra is too tight."

He paused. "Fifty quid the lot. The price of one dress elsewhere if you're lucky. You'll be the stars of the party."

"The belles of the ball," he added.

Steve paid, and we took our bags home from what I noticed was called "Magic Dresses".

Back at the flat we put our bargains on my bed, but didn't say anything.

After dinner and a drink, Steve said "Right, I'm going to go for it. Action stations!"

He undressed but left on his underpants, and started with a bra, which proved more of a technical challenge than we had anticipated.

"These things should come with a manual!" he joked.

Straps had to be adjusted to get the cups in a plausible place. He couldn't deal with the back, so I had to, using an extender to allow a couple of inches. With cups stuffed with socks he admired himself in the mirror.

"Hello, I'm Stephanie," he said, fluttering his eyelashes. "Shame we didn't buy lipstick."

He was really getting into this. Was he gay or at least a crossdresser like Jim?

The yellow dress worked, with his belt, though it was rather short, well up his thighs.

He pranced around, making camp gestures and pouting. It really was rather funny!

"Time for bed," he said in a husky voice and went to put on the pink nightdress.

With just his underpants and the nightie he looked so ridiculous that we both started laughing and couldn't stop.

God! As if putting on a dress could make either of us look like a woman! Jim was different, smaller and quite delicate (or a puny runt, as Dad had often taunted him.) I felt quite angry thinking about my father and it spoiled the mood.

Steve noticed. "Is something up?" he asked with a look of concern.

"Sorry, I was just thinking what a bastard Dad was, especially to Mum and Jim."

Then the man in the pink nightie gave me a hug, and patted my back.

"OK," he said. "Let's forget it for now and watch some TV."

After an hour or so, I heard myself say "OK, my turn." I don't know why, but it seemed I was obliged somehow.

Steve helped me with the bra. I looked at myself in male underpants and a bra. I looked silly, but neither of us laughed. I put on the blue nightdress. It felt all right.

We stood side by side and looked in the mirror. Steve looked ridiculous in a pink nightie. I was in a blue one, and it looked, well, nothing, just a cloth covering. I felt comfortable, nothing else.

Then the flowery dress. Yes, I looked stupid, but something else. I wanted to walk around. I didn't prance or pout like Steve, I just walked around. Not striding like I usually did, more like a boxer's dance. I put up my fists and yes that looked ridiculous, so I put them down and walked around sedately.

Steve's face was a puzzle. Bemused, that's the word. We neither of us knew what to make of this 5 ft 10 boxer in a flowery dress.

We both knew what we were waiting for. It was with a mixture of fear and excitement I put on the green dress.

Suddenly the world was all right. I had arrived. It was a bit having defeated a good opponent in nice clean boxing match. Success, but not exuberant, more calm and satisfied. I can't describe it any better.

I walked around.

"How do you feel in your magic dress?" asked the man in the pink nightie.

"Lovely," I answered. "Thank you so much for buying it for me. And the others."

I didn't normally talk like this, but as I was to discover, my swearing had all but vanished.

Then the man in the pink nightie kissed me in my green dress. And I kissed him back.

As we held each other I could feel his cock stiffening in his pants and felt somehow pleased. It was natural for me to reach down and put my hand in.

"Oh yes," he sighed. I started to wank it gently while we still kissed. In about a minute I felt him coming in my hand and up my wrist, with a mixture of satisfaction and disappointment, while he said "I love you!"

Absent-mindedly I licked the sperms off my hand, then we both washed. Steve took off his nightdress and put back his jeans and T-shirt. He offered to give me wank, but I refused. I was slightly offended to be reminded of my own cock, for some reason. Actually, it was strange that it had stayed soft, as we discussed later.

I didn't want anything but to be in that dress and home with Steve, the man that I now knew I loved. He went back to the bags and produced some knickers to match the bra, which I exchanged for my male ones.

We had solved the puzzle. Steve loved me, but was not gay, because he wanted to love me as a woman. And I was not gay because I did not want him to love me as a man, but as a woman.

"I didn't quite tell the truth," he admitted in a while. "I hadn't been thinking about me in a dress at all, but only about you in a dress. Ever since we saw Jim, I've wanted it. And I've often wished you were a woman before then. When we got to that shop, I got the idea that if I put on a dress, you might, and I desperately hoped you would."

We didn't discuss it more then, but simply chatted about other things. About work, friends, sport and so on. Like any evening except that I was in a dress.

He was relaxed because he had just been tossed off, and I was relaxed wearing a dress. I had not felt the instant change that Jim described. I did not yet feel exactly feminine, but it somehow had felt more appropriate to toss Steve off while wearing a dress, and it was better for him. I did not yet understand it, but my compliance showed I was on the way to being a woman, though I did not know that road yet.

That night I put on my nightdress. I kept the bra and pants, but the bra was uncomfortable in bed, so I had to take it off. He was naked, and I lay with my head on his chest. Then we hugged and kissed for a while. We were both waiting for the same thing. Eventually, my hand went to his cock and it started to stiffen in my hand. It was lovely feeling this. When I had wanked him off, he had already been hard, but to feel it slowly swell was nice.

I didn't just wank him, I sucked him off. Because it was the first time it was one of the most wonderful experiences of my life. I was sort of wanting it desperately and feeling apprehension and disgust.

The first response was - so what was the problem? It is just a bit of warm meat, no more disgusting than my own thumb. Steve is taller than me, but his cock is smaller, so it filled me up, but I did not have to strain. Probably the perfect size.

Before it was totally hard, I explored it and the sensations. It was really interesting to consider a cock from the other side as it were. The knob peeking from the foreskin, the double cylinders on the shaft, the tube underneath, and the veins to decorate it. All of these things I examined with my mouth. I put my tongue into the little hole, and went all around the knob, feeling the shape. I had almost forgotten Steve in my exploration, but it was natural to suck it deeper into my mouth, and then move my head back and forth. I later developed techniques, but my natural instincts did well enough in this first occasion. I held the lovely cock in my hand with just the knob in my mouth as he was gasping "I'm coming! I'm coming!" and I felt him spurt into my mouth. I later worked out that it reminded me of some jelly stuff (possibly made from seaweed) I had been served in Singapore, in both taste and consistency. Not bad, but not wonderful. I never thought to do anything but swallow, and to milk his cock with my hand for the last bits.

My own cock was hard by the end, but I didn't want to do anything with it, and it eventually went down, after Steve was already snoring.

Next day we went to work as usual. In the evening, Steve presented me with some knickers and tights he had bought on his lunch hour. The yellow dress was not so short on me, and I wore it for that evening. Then the pink nightdress.

We had now established a nightly activity. My own cock was stiff each time and Steve offered to wank me, but I refused and actually never wanked again. Every so often I spurted in the night. I wore my man's underpants to catch the spunk if it came. After a while my erections grew weaker, until they were hardly noticeable, and I only wore women's panties. If anything, I enjoyed his cock more, when not distracted by my own.

I began to feel more relaxed and comfortable dressed in this way in the evenings and weekends. I wasn't desperate to be a woman, but I liked this new if unusual arrangement. We couldn't resist buying some plastic breasts, which felt quite good to both of us.

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CAROL

I got a phone call from Carol who asked if we could meet up again, and I said that would be nice. She asked if I had a girlfriend and I said not at the moment, and she said "Lucky me. By the way are you still living with Steve? He could bring his girlfriend and we could make up a foursome at that new Café Bar."

I said no, he was between girls at the moment and she said "Even luckier me. It'll be great to catch up." Steve thought it would be. Carol had been more a friend than a girlfriend. We had both fucked her, but she had a couple of long-term boyfriends. Serial monogamy they call it. I thought it would be good if he got a regular girlfriend, and Carol would do very well, because Steve did like fucking. I would not be jealous, but pleased for him. I had been tossing him off and sucking him, but he would appreciate a cunt and tits, and I wished him the pleasure.

The new place had an eating place, a drinking place and a dancing place, and we used all three. We laughed and reminisced and it was the best evening for a long time. We had had a few drinks and were nicely happy as we took a taxi back to our place, where she kissed both of us and said "Who's first?"

"Don't all rush at once!" she added as we looked nonplussed. "Who wants a fuck?"

"Me," said Steve and took her off to his bedroom. The door was closed, and I heard happy sounds. I was glad.

Eventually the door opened, and Steve was there, his cock hanging down, and he said "She wants you."

Obediently I went in and there she was: the picture of loveliness. Naked with her legs apart. She opened her arms and said "Come here, big boy!" At almost any time in the last ten years it would have been a dream come true, and I would not have hesitated.

I hesitated.

"What's the matter? Don't want sloppy seconds? It's all right - I made him wear protection because I don't know where you naughty boys have been." I stood there and she said "At least give me a kiss. Come to mama!"

I gave her a kiss and she pulled me down onto her lovely boobs. It was so warm and comforting. I was reminded of Mum, and started to cry.

"What's up?" she said, alarmed. "Have I done something wrong?"

"I was thinking of my Mum," I sobbed. Actually, now I thought about it, she did look rather like Mum, but with blue rather than green eyes. Maybe that is why I thought of her as a friend, not a girlfriend. The only time we fucked I think we both realised that something wasn't right. But didn't know what.

We cuddled, which was a great comfort, and I fell asleep, the alcohol having something to do with it. When I awoke, I was alone and realised she had gone off to sleep with Steve in my bed. I woke up with a start later to realise that she would have seen my nightdress on the bed. Fortunately the dresses and other clothing were in the wardrobe.

We had a late breakfast, as it was the weekend, and Carol teased me. "I thought you didn't have a girlfriend, or do you keep souvenirs? She's a big girl, isn't she? Or is it yours?" She laughed, then stopped. "Sorry, I was being silly. It's been lovely to see you boys again. Can we do the same next Friday?"

Eventually I realised that if there was one person in the world I could tell, it was her. And if there was one person I wanted to tell, now my Mum was gone, it was her. So we did.

"I always wondered about you two," she mused. "But you had plenty of girls, so I guess you're bi. Well, if you two are bumming each other I shall definitely insist on a rubber next week."

I was too embarrassed, but Steve explained that no, he was heterosexual, but loved me and wanted me to be a woman, so we had both got some satisfaction with me in dresses, though we had never (as she put it) bummed each other. If it made any sense, he thought I loved him but not man to man, and things were a bit uncertain at the moment.

Of course, she wanted to see, so I reluctantly got dressed. Obviously I looked really ridiculous, and felt stupid and embarrassed. I expected her to laugh when she first saw me, but bless her she just smiled. "Hello, Tony," she said as she kissed me. "Is that Toni with an 'i' now?" I had never thought about it, but she was right and I got my new name.