Magic Dress - April

CHAPTER 1

My new underpants were too small. I told Mum they were great.

"Are you sure they're not too small, dear?" she asked. "I just thought you needed some new ones, but maybe I made a mistake with the size."

"No, Mum, they're...er,...very supportive."

She relaxed and asked me what I wanted for tea.

I was a 34-year-old man, and my mother bought my underwear. Of course she did! She bothered about things that would never occur to me. I had decent clothes for work. Sometimes they got replaced. I didn't have to think about it, as I didn't have to think about meals or shopping. Or washing or cleaning the place.

Apart from the fact that we didn't have sex, Mum was better than any girlfriend or wife.

I had been wondering how to get tight underpants when they appeared by magic!

It was curiosity really. I had often noticed one of my balls disappearing into my body, and popped it out again. I found they would both go in. And if I tucked my cock back between my legs and closed my thighs, it looked like a girl's bush.

If I pulled my underpants tight from the back, it looked as if there was nothing in them. But of course, it all came apart when I moved.

The new pants had a good strong elastic waist. I put them on backwards and pulled them up tight. Carefully I steered my balls back inside my body, and tucked my cock back between my legs. Holding everything in place, I put another pair in and pulled them up. I massaged my balls up as high as I could. It held in place!

I had an inspiration and tucked what was supposed to be the front of the garment between my butt cheeks. It was as if I was wearing a thong! I stroked my buttcheeks and looked down at the female mound between my legs.

I put on my tracksuit trousers and went to my computer. My balls ached a bit, but after twenty minutes they settled down. Walking around I was not uncomfortable. Maybe just a tiny bit, which meant I was aware of my groin but not as a cock and balls. My ass was drawing attention to itself, and it was nice to feel through the cloth with no elastic in the way.

There was a sense of satisfaction from this pointless achievement. It was stimulating in some way, but I never got hard.

After a whole hour, I put one pair of pants back in the drawer, and the other on the normal way.

I did it again and actually went outside like this under my jeans to take out the rubbish, and felt a bit excited. Not stiff cock excited, something else.

Mum bought me singlets for vests to keep warm. I realised that if I rolled one up and put some socks in, it was like a bra, though I could only do it in my bedroom. However, if instead I folded carefully up so that it was just covering my pectorals, it felt a bit like a bra, but did not show under clothes.

Even better, if I stepped down into the head hole of a singlet, and rolled up the straps it made a miniskirt. The only problem had been that my male bits showed through. Not any longer! In my room I could parade around in what looked like a bra top and skirt, like a girl!

I started doing little jobs in what I thought of as my 'girl' state. Nothing strenuous, and just for a few minutes, then a little longer. By the house, but outside, in public. Nothing in my jeans at the front, and what felt like a bra under my T-shirt.

Important pro tip! If wearing a thong, make sure your asshole is really clean. Poo anywhere is unwelcome, but on the front of underpants is odd, and requires secret cleaning and drying.

CHAPTER 2

It was strange but there was a series on the TV about drag queens and Mum watched it. She said it was funny. Some of them had tight costumes with a flat crotch and she remarked she didn't know where they put their dangly bits.

I laughed with her and said I didn't know. But I did.

After the next week's show, I said "Mum, do you like men in makeup?"

"Of course," she said. "It's fun. A bit silly and a bit rude."

"Would you like to see me in makeup?"

"How did you know?" she said. "I was just wondering that. How did you guess?"

"Man's intuition," I said, and she laughed. "Seriously, you can have a go if you like."

She hesitated.

"Sure you don't mind?"

"Of course not. It's just a laugh. You can show me why women take so long to get ready."

She did. There was more to it than I thought.

"I'll just make you up as I know how," she added. "Like a girl going out, but not too extreme."

She did well. So well that it wasn't quite as funny as she thought, and she started making excuses.

"Spare me the technicalities," I said. "I think it's great. Just excuse me for a few minutes."

I went upstairs, took off my jeans and put on her pink dressing gown.

She did laugh then, as I posed and pouted.

I got her to take a couple of pictures on my phone. We had a cup of tea, and then she cleaned me off.

"I always wanted to see your Dad in makeup," she laughed, "but he'd never let me."

"We can do it again next week, if you like," I said.

"Nah," she said. "Maybe," she said in little while.

Next week, she had got some bit of clothing I didn't recognise. It was cheerful in its bright colours.

"It's actually a dressing gown or what some call a house coat, but it's too good to use every day, so it's never used, if you get me," she said with a laugh. "If I tie the strings together, then it'll look like a dress, and is a bit like what the queens wear. Shall we try it?"

"If you like," I said trying not to sound too eager, but also not wanting her to say "Never mind."

She must have been thinking about it because we started good and early, and she had what she called a fun wig from the back of her closet.

Oh god, it was good! If only I could hide my cock and balls and swan around the house like this! Better still go out!

"You're blushing!" she said. "D'you want to take it off and clean up? We don't have to."

"It's fine!" I said. "It's a bit embarrassing, but it's sort of fun. I don't mind doing it every week."

"If you're sure?"

I said I was. And when the programme finished, I said I might as wear it until I got ready for bed.

In my room, I hid my genitals away, and strutted around, smoothing the dress around my groin. I was blushing, but feeling great.

All too soon it was time to restore my cock and balls. I returned the dress(ing gown) and cleaned my face. I felt sad in my pyjamas.

A couple of days later, Mum asked me to look at a drawer she was having difficulty closing. I struggled and finally got it out. There was a black rubber object caught in the mechanism.

She blushed.

"Oh, that's your Dad's butt plug. I should have guessed."

She gave a wry smile, and turned to me.

"It's a bit embarrassing, but it shouldn't be these days. He used to like it when we, you know, made love. I'm told it's good for, er, masturbation, so you probably have one yourself."

"No, Mum," I said, a bit stunned. Of course, she was right, people used all sorts of sex toys these days. She probably had a vibrator, and why not? Still, my parents!

"You can have it, if you want," she said. "There's half a tube of lube as well. He won't be wanting it for at least three years. He's never said, but he may be getting all the anal satisfaction he can handle in prison."

Then she had a little cry about what a foolish man my Dad had been, and how much better things would be when he was released, so the subject was dropped. I still took the plug and the lube.

Dad must have been well practised, because I still hadn't managed to get it in by the time the next drag show came round, and I realised with horror it was the end of the series.

"D'you want to bother dressing up?" Mum said. I said we ought to as it was the end of the series, and did she have anything else for me to wear, so she went and looked in her closets.

It was a green dress.

"Another one too good to wear every day, but not special enough for events," she remarked wryly. "It wouldn't fit me now, anyway. I'm not sure it'll fit you, but just try it before we put on your face, then we can see if there's anything else."

It was better than either of us expected. What we had been doing before had been rude and exciting, but this felt like the real thing. She found a bra and helped me into it, with a pair of knickers in each cup, and the dress looked perfect.

Mum made me up, and in the mirror, I didn't look draggy at all. Just nicely made up, like Mum did on herself. She looked a bit puzzled but we went to watch the show, and for the first time I properly understood it and really enjoyed it. We laughed together, which was lovely.

I excused myself to go to the toilet for a dump. Afterwards I immediately knew what I wanted. I went to my room, and used some lube. The butt plug went in.

I don't mean it slipped in painlessly by magic. I mean this time, I pushed slowly and hard enough for my ass to seem to stretch to the absolute limit, which was fantastic in itself. Then just as it began to hurt too much, it went in, and my sphincter was around the neck, still stretched, but not so much, just nice.

And inside! I guess it was like the satisfaction of a good dump, but sort of backwards and prolonged. Somehow deep inside I felt good. (I later realised it was the prostate of course.)

I felt very sexy. My cock had grown from being shrunk but was still floppy. The dress had a flared skirt, so I did not need to be tucked back, as I would not show unless I got properly hard. I liked myself in a dress and makeup.

I also felt more confident and went down to tell Mum.

"Mum, I'd like to do this again sometime," I said.

"You've got the butt plug in," she said, with a smile. "Your Dad had the same smirk when he did. What do you mean, do this again?"

"You know, put on makeup and a dress for a couple of hours just for fun each week."

I was feeling less confident, as she looked at me the way Mums do when they know you've been naughty but don't know how yet.

"Are you telling me you're gay? Or do you want to be a drag queen? You don't seem to be bringing girls home for sex."

"No, I'm not gay, and I don't want to be a drag queen. I just sort of like it for a change. I can't explain it."

She thought for a while.

"Do you think you'd like to go out dressed like that? Is that what you want?"

"Yes!" I screamed inside.

"Maybe," I said.

"OK. There's a woman at work. Her son likes to go out once a week dressed as a girl. I'll ask if you can meet him. If you are gay, just say so. I won't mind you bringing a boy home, you know."

I went and hugged and kissed her.

CHAPTER 3

It had been a bit of an anti-climax. I had revealed my filthy perversion to my Mum, and she was OK about it. I guess, having been through what happened with Dad, anything else was quite small.

She sorted out some more clothes and we found which ones I could wear. I suppose it was something interesting, at least. I dressed as a girl sometimes in the evenings.

I went out and bought my own underpants! Pretty lacy ones. Men do buy them for their girlfriends.

I was just in my usual sloppy man clothes, when the boy Mum had told me about came round.

His name was Simon, and he was in similar clothes to me, just smarter. A man. A shy man, a bit slender, with his hair back in a ponytail. He was twenty-four.

There was polite small talk with Mum and a cup of tea, then we went to my room, and I showed him my clothes.

"You've not been crossdressing long, my Mum said, and you've never been out?"

"Yes, but I've sort of been thinking about being a girl. We watched that drag series on TV."

He shuddered, and I could see he was quite annoyed.

"A travesty! Men mocking women! It shouldn't be allowed! If that's what you're into, I can't help you!"

He stood up, ready to leave.

"No, no! It's only because Mum watches it that we talked about me crossdressing, and she mentioned you. I definitely don't want to be a drag artist!"

That mollified him a bit, and he sat down, then continued.

"It's like white people putting on black face and doing jolly negro songs to be amusing. They used to do that, but it wouldn't be allowed today on TV. I don't know why they can mock women in this way. Women are wonderful. You and me are not lucky enough to be women, but if we are permitted to be Tgirls for a while we should appreciate the privilege."

I asked him about Tgirls and he said it meant transvestite or transgender girls -- men who liked being girls. Some had operations, but a lot were like him, just dressing and being a girl socially. It was misused in porn, so some completely transgender women were offended, but he was one of the ones who liked it. He thought the T stood for 'trying'. He didn't claim to be a real girl, but was trying to be like them. It was the opposite of drag: total respect and humble appreciation of how wonderful they were.

The truth is I had not been out much with girls or boys for that matter. I mainly played computer games and watched TV. Part of it was hiding from publicity with Dad's trial, but I was a bit shy before that.

As diplomatically as I could, I asked what happened when he was out as Simone. Did he have a particular boyfriend?

"Well, there are boys who are friends, but none in that sense. I mainly dance with girls and socialize in mixed groups as a girl. I do kissing, but don't look for sex, though it's as well to be prepared to give the occasional handjob to stop a boy going further. So if you're looking for an orgy, don't ask me."

"That sounds wonderful," I said, sincerely. "Much better than my life now."

He turned sympathetic.

"Yeah, Mum said you two had had a hard time, so it's understandable. Would you like to go out on Friday next week? You could come as a boy or a girl with me."

I didn't have to think about it.

"A girl, please."

He asked to see the clothes I had, and got me to put on the green dress.

"It's the best you've got. Very nice, though maybe a bit old. It's your Mum's after all. I doubt you're ready for a short tight skirt, yet, so we'll try it. Do the best you can for makeup and wear that fun wig. The places tend to be a bit dark anyway. Girls spend a fortune in time and money looking pretty then dance in the dark!"

"You'll need some shoes, of course. I think you're the same size as me, so I'll lend you a pair. Almost no heels, so you should manage. They might not be comfortable, but girls have to put up with that. When you buy your own, we'll know you're committed."

He noticed something.

"That's a big butt plug you've got there."

I was pleased to get what I took as a compliment.

"Oh, do you use them?" I said brightly.

He shuddered.

"Perish the thought! I can't stand the idea. Everyone thinks if you're a crossdresser you must want to be fucked up the arse, and there's guys who really fancy it but kid themselves they're not gay."

"No offence. Do what you want, mate, and enjoy it, but not my cup of tea, thank you very much."

On the day, Mum helped me with makeup and the wig. My legs were shaved and my nails were varnished. I had the shoes which had been sent via Mum's work. They were women's shoes, but not high heels. With a handbag from Mum, I got a taxi to Simon's house.

Out came Simone, and what a difference! In place of the shy man was a vivacious young woman in a short skirt trotting out on high heels. She smiled and tossed her head to show her hair. Getting into the taxi, she kissed me.

"Hello, Simone," I said.

"Hello,... er? What's your female name?"

"I don't know. Haven't got one, never thought about it."

"Hello, April" she said "It's the start of the month."

"Oh yes, it's All Fools' Day," I said and we both laughed.

I told him I had been born on the first of March, and I had been named Mark because of it. My parents had been sure I was going to be a girl, and had never thought of a boy's name.

Simone's excitement rubbed off on me. I was apprehensive, but hopeful.

The first stop was a café bar, where Simone was evidently well-known, and several girls, all in short skirts, waved or called out.

"Hello, gang," Simone began, and one of the girls gave me a snooty look.

"I see she's brought her Mum," said the snooty girl, loud enough for me and Simone to hear.

"Mum, I'd like you to meet Sandra," she said, pointing to the snooty girl, whose face fell.

"Trish, Abigail, Claire..." I lost track.

"Nice to meet you, Mrs Ashley," said Sandra with a nervous grin.

"Likewise, Sandra" I said, "And it's April, please!"

Then I was pretty much out of it as they chattered away nineteen to the dozen. I just gave grunts and smiles, and sipped at a diet coke.

Well, I was ten years older than Simone, but perhaps not too bad for her mum's age.

At some invisible signal they got up and started walking down the road. I kept close to Simone, who was having at least three simultaneous conversations. I was aware I might not be totally convincing in the street lights but hoped they were too busy talking, checking out other girls and some men, and watching their footing on some of the paving.

We went to a club. As promised, it was dark enough to hide my sins. In fact, it was mostly girls dancing with other girls where we were, though there were obviously some boys who knew Simone, usually in pairs, and the loser danced with me. She got kissed several times, but I didn't, which was no loss to me or the boy. Some of her friends went off with boys and didn't come back.

I went through the painful ritual of a queue for the loo.

By the end of the evening, I was exhausted. It had been a long time since I had gone out like this and never so active. I had been one of the boys standing around and eventually asking for a dance near the end of the evening and getting turned down.

CHAPTER 4

In the taxi I arranged to meet Simon for a debriefing. He came round a couple of days later.

I understood what he got out of the experience and wanted to learn myself. It had been so much better than going out as a man. Apparently, Sandra had soon tumbled to what I was, but accepted the joke was on her.

Simone normally hid her genitals with some special thing, so I showed what I did with my underpants, and Simon was impressed.

"Why don't you try it next time? When it becomes uncomfortable, or you need a pee, just rearrange yourself in the loo. You'll be OK with that dress. Don't try too hard the first time."

We went out once a week, to different places. Simone pretty much had a different one for each day of the week, but rarely went out twice.

There were different places and different people. Some were loud, and some allowed a bit of talking. We were always with a crowd of girls. Simone borrowed a wig off someone, which she and Mum agreed was better, and I got my makeup improved.

Simone probably looked like a girl to most men. I was, of course, far less convincing, but it seemed a lot of young people now accepted this kind of thing. There was a trans man who sometimes danced with Simone and a couple of other girls. The occasional guy (usually a bit drunk) who started to get abusive about me was quickly faced with several stroppy girls. Tiny Abigail was by far and away the most intimidating!

The days I was going out I spent in eager anticipation. Being immersed in girlness was just heaven. To be one of these smart and sexy beings was fantastic. And yes, it was sexy, but somehow my cock behaved. That is, it did, providing I kept thinking of myself as a girl, not sexually or anything, just socially, I suppose. It was only if I thought about being a man dressed up that it did, and if I was tucked back, the erection was so painful I had to go to the toilet and rearrange. There was always a queue, so I couldn't stay too long in the cubicle, but the green dress hid things if I was careful.

Each day after my girl night out, I was in an afterglow of femininity! At work I was a bit distracted but so cheerful. If I was at home, I spent the day in makeup and nice clothes and Mum called me April. This mostly happened with a Friday night, so Saturday was good as well. On Sunday morning I put in the butt plug and had a magnificent wank. There was another one in the evening. Then it was back to my male self.