Magic Dress - Bobbie Pt. 02

CHAPTER 7

It was a key moment in my life. I was wearing a nice green dress, which I was sure was only the start.

In addition, I had just sucked off a man in a dress, who was going to teach me to be a girl. And had handjobs to look forward to.

Thinking about it, my feelings when I first stood there in a dress were something like "Hee hee hee!" I was like a child, reading comics under the bedcovers with a torch when you are supposed to be asleep, or eating cake and ice-cream from the fridge which is supposed to be for tomorrow. Delicious in itself, of course, but much more so because it was forbidden.

I was a man. It wasn't allowed. I was being naughty!

A naughty girl, in fact! That was what it turned out to be as a sissy. Delicious and naughty. And twice as good because it was naughty.

But Georgie was tired.

"Look," she said. "Why don't we have a sleepover, and start again in the morning?"

We had a cup of decaffeinated tea, then took off makeup and prepared for the night.

"I actually bought this nightdress for you," she said of the one we had bought together. "I just didn't know when I could offer it to you."

There was one more detail. Washing our male parts and underarms well, and a little spray so that we could be smelling female only.

I suppose the point of a girls' sleepover is of course not the sleeping, but the whispering together in bed. That is when Georgie started on my education.

"I don't know how far you'll want to take it," she said. "Maybe it will be just this once, or maybe you'll have a bit of fun and then go back to the real world. Or maybe you'll go all the way and have surgery and end up married to a lovely man. Though I'll warn you, that is a long and difficult road."

She hugged me and kissed me on the forehead.

"I think you're a lovely person, and I wish you happiness in any way that suits you," she added. I snuggled closer.

"I can tell you what it was like being me, and a few things I have observed, that's all."

"For me and people like me, being a sissy was essentially a hobby. I had to work and deal with all the other things in life to keep things going. To actually live as a woman full time never occurred to me. It was just my off time."

"I was very limited when living at home, but when I got my own flat, I could do more, so evenings and weekends became my girl time. Eventually I got the courage to go to a gay club, and finally made some friends who accepted me for what I was, as I accepted them. It is just so much better to share. I suppose it is the same for people who collect stamps or like model railways. Yes, fascinating by yourself, but great to see other people for mutual appreciation."

"It wasn't all plain sailing, but I was lucky enough to meet some men who treated me well and introduced me to sex in a nice way. So I became a slut. That means having sex with lots of men, but it does not mean being careless, just having a lot of friends with cocks to share."

"Sissies don't have to be sluts, though I'm guessing you might be. The first thing though, is to try being a thoroughgoing sissy. See if you like it, or if all the palaver is worth it."

She was tired, so we slept.

It was strange sleeping in a nightdress, but not in any way wrong. I was sure I would do it often.

I came awake several times and thought of how I had felt in the dress. What was that feeling?

I eventually decided it was hope.

CHAPTER 8

The next few weeks were an intensive course, but a lot of it was how to be slow. Washing, shaving, putting on makeup, taking it off: these were things that were best not hurried. Not a chore, a privilege. Similarly choosing clothes, whether in a shop or just getting dressed, was a little pleasure. Not like a man's quick routine. Putting something on; taking it off again; trying different combinations, was not indecisive: it was enjoying the possibility of choice. Getting the two of us ready could use up half the evening, but in a pleasant way.

And clothes were something to feel as well as look at. Most particularly underwear: silk, satin and lace. With practice fastening a bra became routine, but always a welcome step in the evening to leave the boring man behind. I liked to feel my hands move from a slip or knickers to my smooth thighs. But even a cotton dress moving against my legs as I walked about the room, or a clinging woollen one keeping close to me, these were all tiny girly sensations.

Georgie had several outfits I could wear, but I had to buy some more, of course.

Eventually I grew bold enough. It turned out to be quite simple. Take the goods, hand over cash or a card and don't say anything. Maybe it was for my wife -- maybe it was for me -- that was not their concern and I did not need to explain. Of course, I had seen how the beauty parlour and the lingerie shop had accepted a male customer, though it would be some time before I had the courage to try it myself.

I didn't have much money, of course. Some things could be found in charity shops, but underwear had to be new. A sissy has to have standards.

Fortunately there were shops like Primark as well as the more exotic and expensive specialist lingerie shops. (But there was no reason not to spend time looking. Maybe I wanted a present for my girlfriend -- maybe it was for me -- it didn't matter if I was only looking.) I could not try on, but could return things (not knickers), so it was OK to make some errors.

The biggest change was in my head. It became easier and easier to slip into a feminine feeling. All the clothes and rituals were sort of hypnotic. By the time I was nicely made up I had become content. Despite what the mirror said, I was a pretty girl. All of this I learned from Georgie, of course.

I took to wearing as much female clothing as I could for my cock services. Not just knickers, but a slip with lacey bra details, and stockings or tights. My remarks of encouragement to the two men concerned probably betrayed the fact that this was more than a chore, but they raised no objections.

We two girls now were sucked off and sucked each other off twice a week, but not on the same day. I knew that it took about three days for seminal volume to build up so we both got about the maximum load that our bodies could manage.

Under these circumstances being sucked off gave me an orgasm which seemed better than any I had had before. The following day I was so calm and feminine it was an equal pleasure. The next day I began to feel excited in a girly way at the prospect of cock, so really enjoyed it in the evening. It was best to give a handjob during the day and suck off Georgie in the evening. Two cocks in one day!

Until the time of my own next coming, I was in a sort of sexy satisfied but yearning state, which was delicious in its own way. I was so glad to give Georgie a good load, and so grateful when she gave me hers.

CHAPTER 9

It was mainly about the clothes (and the feminine feelings in our heads). We both knew that it could not remain indoors for ever. Georgie was longing to go out as a girl again, and I was both fearing it and wanting it.

It was OK prancing around in private and pretending, but the only dress that gave me even the slightest feeling of confidence was the original green one.

Georgie said it suited me very well, but she had not worn it much, though she didn't know why. Then one day she decided what the issue was.

"It's too ladylike! You don't look like a slut at all, more like a lady. That's it. I'm a sissy slut, so it never really suited me."

From the charity shops I managed to get Georgie what she sadly called 'age-appropriate' items for every day wear at home. The visiting nurse had been surprised, but had not objected, and noted she seemed both more cheerful and generally in better health.

It was a warm day. People were at work; children were at school. We went to the park.

I was in the green dress and a wig. Georgie was in her dowdy outfit, but her own hair, done as well as I could manage. I wheeled her around, and we went home. Five minutes each way in the car, a slow walk around, straight back. Half an hour at most. Two hours getting ready, getting courage and using the toilet several times, but I had done it! I knew I would eventually manage the rest.

There was one thing missing: shoes. I could not be a proper girl until I had some high-heeled shoes, and certainly not a slut, said Georgie. But her shoes were too small for me. We had to buy a pair.

I was in my man clothes, and Georgie was in the wheelchair at the shopping centre again. There was only one proper shoe shop selling the kind of things she thought were suitable. The shoes were visible immediately: green and glittery, and in a larger size. But they were too expensive, and I could not really buy them without trying on. Georgie tried on several, just for fun. Although she could not walk in heels any more, she liked to sit in them at home, and in the wheelchair.

Still we looked around some other shops and had a cake and coffee looking out at the people around.

It was a week later when I finally got the courage. In the green dress and wig and trainers I drove to the shopping centre and wheeled Georgie in. The shoes had gone from the window.

Georgie insisted we go in. An assistant looked at us oddly, and not in a friendly way. There on a rack were items reduced for quick sale, including the green shoes, now half price! I took them and put them on. Sitting down, they seemed to fit. Standing up, I nearly fell over, but with one hand on a rack took a couple of steps. Really strange and a bit worrying, but that was it. I bought them.

"Will that be all, er... madam?" said the assistant, and I nodded and paid.

With our loot, we were heading out when I heard a familiar voice.

"Georgie! Is that really you?"

It was Tony, but he was looking at me. As he got closer, his smile faded.

"Sorry, I thought you were..." then he did a double take.

"Hello Tony," said Georgie, and he looked at her, and his mouth fell open. "Long time no see," she added.

He looked back and forth between us, then laughed.

"Small world!" he said.

"Why don't we have a chat over a coffee?" suggested Georgie, "but first would someone take me to the disabled toilet? Tony?"

"Glad to oblige," he chuckled. They both went into the cabin while I hung around outside praying that I wouldn't be challenged by security staff. It took quite a while, but they both came out smiling.

"Yes I did," whispered Georgie to me.

Over coffee it came out that they had both been friends with benefits but had both moved away about ten years ago, and had come back to the area without knowing about the other. In the dress and wig I had looked like Georgie when younger, but now he recognised her as older.

She had sucked him off in the toilet, of course.

CHAPTER 10 -- Sid

Tony changed a lot of things. There had been some problems with money from the sale of his parents' house, and with his industrial accident, but these were now sorted and he had some compensation. Georgie sold her little house (for not very much) and they moved into a bungalow together. I think that in Tony's eyes Georgie had always been more special than she realised.

Now rather than being a part-time good-time girl, she was a woman all the time, and down to only one cock (but plenty of that, I gathered). With a partner, she was no longer entitled to home care visits.

And now I was dressing up on my own in the evenings and weekends. But not entirely alone.

Sometimes I visited them and I was invited to suck Tony's cock occasionally.

This is what Georgie told me.

"As a nurse, you will be aware of the possibility of infection, so cock sucking has to be done very carefully, and only with men you are sure about. For fucking, you can make them use a rubber, and for handjobs make sure the spunk keeps out of your mouth and eyes for any casual one."

She said she had made sure Tony was clean and not going with anyone else. Obviously his cock was mainly for her, but she wanted me to practise serving a straight man.

The final phase of my training was in fucking. Tony taught me to take and enjoy anal sex. It was uncomfortable and odd at first, but I soon grew to like it, and eventually had my first anal orgasm, which was indeed better than I would have believed.

Meanwhile it was Sid who (as he put it) 'sussed' me out.

"Yer a poofter, right?" he said. I said nothing.

"Ya like me old todger, don't you? Well, yer not the first. I know me face is nothing to write home about, but me trouser snake has had a few friends in its time."

He had been in prison a couple of times, and men giving handjobs was not unusual. There was rape, of course, but he swore he had never done that, only been tossed off by those who liked doing it.

"Do yer dress up?" he asked without hesitation.

"Well..."

"I knew it!" he said triumphantly. "It'd be great if you did fer me. Fucking great, in fact!"

I told him I wouldn't do anything but a handjob, and he shrugged.

"Look at me. I can't force yer," he said with a wry smile. "But a bit of female company would be nice. See ya on Saturday!"

Georgie was delighted.

I went round to their house early. Georgie talked about her experiences to get me really excited, then sucked me off, so that I could be soft. In some control pants with my cock tucked back, and a bit of padding at the back I had a decent shape for the miniskirt she chose.

With my wig and makeup, Tony looked me over.

"You look a right slut!" he said. To hear it from a man was wonderful! I kissed him, and Georgie said "Attagirl!"

Tony drove me to Sid's house, and said he would be back in two hours, or if I rang.

I had practised, but was still not perfect on high heels, and the miniskirt was a bit restrictive, so I wobbled with little steps down the path and pressed the keysafe combination to get the key and open the door.

I got some honest appreciation from Sid.

"Yer a right little slapper!" he said. "Fucking gorgeous!"

I did as usual, and went to unzip his trousers.

"Whoa, girl!" he said in alarm. "Steady on!"

I was flummoxed. What was wrong.

"What's the point of yer dressing up, if we ain't gonna play the game?"

"Play the game?" I asked.

"A drink, a chat, a bit of flirting. We both know what we want but you act reluctant, and I feel good when I finally persuade yer. That's what boy-girl dates is all about."

I felt so stupid.

"Shall I come in again?"

"Fucking right, you should!"

So out I went.

In I went.

"Hello Sidney, thanks for inviting me."

"Great ter see yer, Bobbie! You look fucking fantastic!"

I turned around slowly.

"Do you like my outfit?"

"Not arf! Come and sit down and have a drink."

There were two wine glasses with red wine.

"I shouldn't when I'm driving," I said. (Just a little lie. I wanted to be careful.)

He gave a smile and a wink.

"It's only Ribena. Blackcurrant squash. I'm not allowed alcohol, anyway, but we have ter go through the motions, don't we?"

I sat down beside him on the sofa and sipped a couple of glasses of Ribena and talked. He put his arm around me and I was conscious of his poor crippled hand, and kissed him on the cheek. He turned a bit more, and looked pleading, so I kissed him briefly on the lips.

I had never kissed a man before. It wasn't marvellous, but it was significant.

I lowered my head a little and looked up at him through my eyelashes as Georgie had taught me.

"I quite like you," I said softly.

He took his arm away from my back and put his hand on my thigh. The poor crippled hand of an old man, but it must mean so much to him, and it meant something to me. My eyes were getting wet.

I carried on with light talk as he gently stroked me. He was definitely being near the knuckle in his comments, and I was getting excited to be on the receiving end. A man was not asking out loud, but trying to persuade me!

I turned and kissed him full on the lips -- a proper kiss -- and put my hands on his craggy face. My eyes were closed. He reached around and held me.

At last I knew what it was like to be a girl held by a man -- a man who wanted me. For sex!

My hand went down to feel his hard cock through the trousers.

I knew it was time, but not to rush.

We were kissing, and I was rubbing. He put his hand on my boob. He probably couldn't feel the difference, but it was the fact that he still did that was so nice. He was a proper man, and deserved a good wank.

I got his cock out, and was down on the floor with my face close, not like I had done before. It looked even larger. I held it in both hands and felt the awesome rigidity and the veins standing out. There was a bit of precum on the knob, so I spread it around a little with my finger, and he gasped.

Quickly I got lube from my handbag and put a blob on my palm. I then began a very slow wank, all the way from the tip down the long shaft and back again. It was more important to me than ever that he enjoyed it as much as possible. I realised that this was the feeling I had been wanting when I had wanked cocks before. But then I could not give in to it: it was just a kindness to a patient. Now I was a girl, and it was my pleasure to enjoy this magnificent organ.

As it dried a bit, I spat on my hand. I did not trust him to be free of infection (the nurse was still in my head) so would not put my mouth on directly. In any case it seemed impossibly large to suck, although the idea added to the excitement.

Although I had been sucked off, I could feel the blood going to my groin, and stiffness between my legs. Engorgement of my pussy, I thought to myself, and relished the discomfort.

Sid did not hide his feelings. He was groaning, swearing and telling me how good it was, all of which made me happy. I judged it was time to speed up, and his response told me I was right. Still, I was not too fast, to prolong it for both of us.

Then I could feel he was ready, and realised I had not put a towel down as I usually did. I was certainly not going to swallow it, but my face was quite close. All I could do was turn my head away and close my eyes as his spunk hit my cheek, neck and blouse.

"Fuck!" he said loudly, and groaned. I looked and saw his eyes were closed.

He opened them and saw me. He grinned in the dirtiest way ever.

"Now that's what I call a date!"

I cleaned us both up (though there was stain on my blouse and his trousers) and repaired my makeup. I went to the toilet to have a pee, and release my cock for a bit. It was soft enough for me to tuck it back.

Then we talked again. It was still he was still treating me as a girl, but now the deed had been done. We were friends. Friends with benefits. And I was having fun as a girl: a bit of a slut as well.

Sid was crude, but he was nice. And for a slut, crude wasn't bad.

He told me that he would still pay me for the two hours, but I should go, so I rang Tony, who turned out to be outside already. I don't know if he had waited.

Next time I was on my official visit, he told me he did not want a handjob because he now had a girlfriend! So I got on with the housework.

On our next date things had changed, of course. I was not experienced enough, but he knew exactly how the second date should go to its inevitable conclusion, and I had a lovely time.

But there was a problem. I refused his money. It would be like money for sex, and I couldn't do it.

Finally he made a proposition. Dates would only be in the evening, and no money, except he would pay for a takeaway meal. But if I could come along in my man clothes and do some housework, he would pay me. The extra money was useful, so on most Saturday mornings I actually did an hour or two. Part of this was drinking tea with him and being told exaggerated accounts of his hot girlfriend.