Magic Dress - Kelly

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From gay man to girlfriend.
7k words
4.12
14.7k
6

Part 41 of the 82 part series

Updated 04/30/2024
Created 02/01/2019
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CHAPTER 1

There have been three revelations in my life: when I realised I was gay; when I realised I was in love; and when I put on a dress. I suppose I should add when I had a fitted kitchen as a fourth.

The first was at university. I had done the subjects I liked for A levels: chemistry, physics and geography, despite my teachers' pleading for me to do maths instead of geography so that I could get a career in engineering. But I didn't like maths that much, so did geology instead of chemical engineering. Ironic, as it turned out.

There were some introductory talks including one on safe sex which scared the shit out of us, especially with AIDS, then known as the 'gay plague'. There was also a gay man and a lesbian to explain about their lives. I can hardly express how grateful I was to learn that I was not a failed heterosexual as I had been, wanking almost out of duty over girlie magazines. (This was the 20th century before free internet porn and web pages about everything.) Yes, they excited me a bit, but not the way they did most lads. At last I understood.

I like women, I like them a lot, but I am sexually attracted to men, which I discovered was not that unusual. I liked dicks, and there was no reason to pretend to myself or anyone else that I didn't.

Except that I told my parents and was thrown out. My dad refused to speak to me again. It was his wife (my stepmum of only 3 years) who handled the practical side of dealing with my things, and said goodbye. I moved in with my older brother Harry for a while, and he supported me in every way, like an angel.

Hesitantly (and safely) I developed relationships at university. I actually have quite a small dick, which I really like, because of the contrast with others. Even an average one is nicely bigger, which adds to the self-confidence of my partner, along with my honest appreciation. It was just handjobs for quite a while: giving and receiving. I liked the giving more, but accepted it from a partner for his sake.

Eventually it came to anal sex, where it was quite clear that I had little interest in giving. I am a receptive homosexual. Most of all I enjoy a nice dick thrusting in my arse until it comes! There is wonderful satisfaction in being filled and in the joy of my partner. An arsehole has other functions of course, and these sometimes make being fucked less pleasant or advisable, so then I am glad to give a handjob. Obviously, we used condoms, and because of the fear of AIDS I never used my mouth.

My geology degree took me onto drilling rigs for oil and gas, looking down a microscope at drill cuttings to determine the type of rock, and hints of oil. (Microfossils are a good sign, since oil comes from life.) Samples were often brought to me by the drilling fluid engineer, commonly known as the mud engineer, which sounds amusing until you find out how much money these guys make. The drilling fluid is the lubricant for the drill, constantly pumped down the drill pipe.

To cut a long story short, I eventually trained and became a mud engineer, with exams which were harder than those at university. I needed to understand geology and to do some very important calculations. Getting things wrong with the drilling fluid can hold up progress at best, or worse break the drill off, and at very worst mean the hole has to be abandoned. So the maths is critical!

In this all-male environment, I became popular even with some men who were otherwise straight. Conditions were sometimes hard, but I was doing a challenging job with good comrades, getting my arse well fucked and being paid well!

My name is Keith, but someone compared me to the kelly on a drilling rig and I got the nickname Kelly. (It is the item on top of the drill pipe which is rotated. It is constantly being screwed into the ground, and has the drilling fluid - a thick slimy liquid - pumped into it. Not a particularly good joke).

CHAPTER 2

I admit the fact that it was Bill's big dick that I first noticed in the showers. I could not wait to get that magnificent dong in my arse! However, that was unlikely to happen, since he was recently married and in love with his curvaceous bride.

Yet there was something else. We clicked immediately. I can't explain it, it is just something that happens: friends immediately and for life. However, he was the new tool-pusher: the person whose job it is to get the hole done as quickly as possible; minimizing downtime and making all operations slick and effective. Part of my job was to tell him we had to stop to change the mud formula, that the drill needed to slow or it would jam in the next formation, that we could only run on half flow for a while to change some screens and so on. This meant we had vigorous technical discussions, swearing heavily at each other.

Somehow we needed to separate our personal and our professional life. We didn't make a formal decision, it was just that he called me Keith for business as an engineer, and Kelly as a friend. I ended up talking to Bill the toolpusher or William the friend. (Easier to distinguish than Will in a noisy environment.)

Again I didn't make a decision, but found I was acting a bit camp around William, sort of effeminate, which the guys found amusing. In hindsight I was of course trying to attract him.

I don't know if it was my efforts, or just simply the sexual frustration of some extra weeks stuck in the North Sea during bad weather, but William eventually accepted my offer of a handjob. It was then I knew I was in love. That dong was the most beautiful thing in the world, and when it came like an oil well gushing in a cartoon, I felt a thrill like never before. He must have been holding off, because it was a lot. He was embarrassed how much he had enjoyed it, but shyly agreed to another a couple of days later. I think he felt something for me, though he wouldn't admit it.

It is not unusual (though not always possible) for the companies to try to keep successful teams together, and after quite a number of successful holes we were obviously a good team, along with a few others. He accepted a handjob from me on a routine basis, and our private time also developed in a more intimate way, though nothing overt. I liked letting him treat me in a way I would never do as Keith and Bill. A bit like a woman.

It was one of the other guys who had used my arse who recommended it to him, when he must have been missing his wife a lot. Thus after a few years together I finally got my wish. The guy who recommended me had quite a big dick, so I was not unprepared, but even so I could tell the difference, and it was divine. It was perfect. I did not want anything bigger; I just wanted that dick to fuck me longer and more often.

I was delirious with joy, and he was shocked how good it had been. That was the thing that made him guilty. I don't know if it was better than his wife's cunt, but I think there was not a lot of difference. He hadn't talked much about her in the last couple of years, but now it came out. He loved her, but her boobs were too big. She had slimmed for the wedding, but now had put on weight. He loved her, but it was difficult being away from her, and just wanking wasn't enough.

Of course, I said he was not being unfaithful, since it was not another woman, and it would be best if he was not sexually frustrated as this might affect his judgement at work. Thankfully he was easily persuaded, so began to fuck me regularly when on the rig. This could hardly be secret, so I was sometimes referred to as Bill's girlfriend, and the guys began to talk to me a little in that way. He was still Bill to everyone but Kelly.

CHAPTER 3

It was one of those times when everything seems against you: the weather, the equipment, the geology. It was an exhausting time for all: stopping, starting, fixing machines, changing mud, finding another problem, missing sleep. But we finally got through it to regular drilling.

Once we had had a shower, I did a round of handjobs which were much appreciated, then we went to William's tiny bedroom and office.

For the first time, I actually took his dick into my mouth and sucked him a little bit, before applying lube up my arse, putting on a condom and bending over. I think because he was tired, it just went on and on, which was what we both wanted. I was gently dribbling on the towel on my bed.

When he finally came it was not an explosion, just a relief, but I couldn't have been happier.

That's when he said it.

"God, I wish you were a woman. If you only had tits, you'd be perfect."

He pulled out, I turned around, and suddenly we were kissing. I really don't know who started it, and I don't care, it was just lovely, even better than the fuck. I knew I loved him, and I think he knew it too.

Back on shore, I went to see a friend from university. A very pretty lesbian named Sue who liked nice dresses and probably had plenty of men lusting after her. But they had no chance as she had a very nice woman as her husband. It may seem odd, but she really was my best friend and female; someone I trusted.

I explained what had happened.

"Come with me," she said. "Let's try something."

We went to a little boutique where she was known to the manager, and she explained what she wanted. I was measured up and waited in the little fitting room, while they brought me some clothes. I just stood there in my underpants. In most cases they just held things up against me, shook their heads and left. We tried a couple of dresses. One felt wrong. One looked wrong.

Then they gave me a green dress. I put it on and felt a great sense of relief. It was a bit like when William had first fucked me. Something right at last. What I had been waiting for.

I no longer wanted to be a woman. I was a woman.

I whispered to Sue what I felt and she gave a big grin.

"Biology makes sex, but gender is in the mind," she said. "The rest is detail and decoration."

With her help I got a full set of female clothes and learned some basic makeup. She chose a couple of wigs for me. I still went to the office as Keith, but spent more time as Kelly with her and at home.

On the next offshore tour, I took some nice underwear to show William, and took to wearing lipstick, which went down OK with the guys who came to me for handjobs. I no longer had my arse available for anyone but William.

My brother Harry and his wife Fran had already accepted me as gay, so it was not too much of a step to accept me in a dress. I was able to spend some time with them and Fran helped me with various things. I mentioned I had a special man friend, but not that he was married.

One evening on the rig, William and I were actually joined together when the tilt alarm went off (i.e. the rig was falling over). We scrambled into boiler suits and got into the lifeboats. The tilt was rectified and we got back aboard, but it was a terrifying experience. We didn't feel like fucking but clutched each other on his narrow bunk and kissed. I think it demonstrated how much we cared for each other.

But we also agreed that we were going to give up offshore work.

Bill got out of it first, so I found myself on a rig with people I knew, but a new toolpusher.

"I've been told about you, Keith or Kelly," he said brusquely "and I don't really care."

"There's only one hole I am interested in drilling and that's all. You and the lads can do whatever you like so long as we keep going down as fast as possible, and you're available anytime if the mud system needs it."

Something unexpected and unpleasant happened, now that William was no longer around. I was still treated as Kelly off duty, but in William's absence I was expected to be available for sex. Just for convenience. A leisure facility. Everyone who had ever fucked me now felt they had a right, and a couple who had formerly had handjobs wanted to try out my arse. I suppose I was in the situation many women find themselves. It wasn't exactly rape, but I didn't like it and didn't really know how to refuse.

I had mixed feelings. Part of it was annoyance that I enjoyed being fucked often, but also anger that it wasn't my choice, and overall guilt that it was my fault not theirs. Handjobs were just a chore, not an entertainment for me. There was no-one I could turn to. The new toolpusher certainly would not help.

When I had finished the contract, William was far away on a set of long tours not using my company for drilling fluids. I decided to take a big step.

I ended my employment, and lived off my savings till William came back, being female as best I could day and night. Fran was very supportive, though I don't think she entirely approved. With her and Sue to guide me and escort me when possible, I adjusted to the different way the world treated me. There were more than a few difficulties, and I was threatened but not actually hit when out shopping.

Obviously, William's wife was eager for him but he did manage to come and see me a couple of times, and seemed pleased with the new me. I took an even bigger step. He wanted tits and I would give him some. As soon as he was away again, I went for the operation.

In Britain, the doctors generally won't carry out the operation unless someone has been living as woman for two years and has received extensive psychological assessment and counselling. However, there are other countries where the ability to pay is the sole requirement.

I went to see the surgeon wearing the green dress, and we agreed that they should be just the right size for me to continue to wear it. I don't know why this seemed important: it just did.

I took the best quality he could provide, and was pleased with the result. They were still a bit sore when William came back but he was thunderstruck and obviously pleased. I had also had electrolysis for my facial hair and waxed my body hair. My own hair had grown long enough to be styled so that I did not need a wig, and I took advantage of being given a full makeover to learn the best makeup for me and how to apply it.

By the time he returned I was more than passable. It had taken about six months for me to be confident and just be accepted. I had needed practice with things like the voice and walking, but also the attitude and clothes. I was glad I did not have too big a bust.

Of course, I still had my dick and balls, but with a combination of elastic underwear and choice of outer clothes they were not noticeable, and I was sufficiently comfortable to forget them when out and about. Any further surgery was something to be considered for the future.

Sue and Fran helped me to a fairly good wardrobe for a businesswoman, and I approached a consultancy to see if I could sell my skills. They found my knowledge and experience acceptable, and were glad to have a woman on the staff. The job might entail the occasional trip offshore to make an evaluation, but not for lengthy periods.

CHAPTER 4

William settled into a shore role with his company and I was working as a consultant which was patchy but overall good. The only problem, of course, was that he was with his wife most of the time, and had to make imaginary business trips to see me. I lived and worked on the other side of the city: near enough but not very likely that his wife and I would cross paths, or that her friends would see us together.

In order to occupy myself I decided to renovate where I was now living. As my brother Harry is a plumber, he knew reliable tradesmen and of course did the plumbing himself. I was just having the kitchen done when Harry hurt his wrist and asked a friend called Ben to fill in.

I was slightly upset when Ben broke the only picture I had of William and me together, celebrating my new tits at a restaurant. But it was not really a big deal and he had stayed late to apologise, so I made him dinner and we talked.

Funnily enough he looked quite a lot like William: handsome in a similar way. If I had not been spoken for, I would have been very interested. Unfortunately, I said more than I should about my situation because I was upset. However, he just got on with the job over the next few days and I was pleased with the result. Looking at his business card, I noticed he had the same surname as William and lived not far away from him.

I mentioned to Harry that Ben looked a bit like someone I knew and he said he thought he had a brother in the oil industry.

Eventually I phoned William's wife, Henriette, introducing myself as Keith the mud engineer, whom she had heard of, and confirmed that my suspicions were correct: he and my plumber were brothers.

In all honesty, I decided that she deserved to know, and made an arrangement to meet her. Of course, she had suspected something, but had never thought of her husband with another man. Initially my transformation made it worse. This was partly because she had never come across anything like this (few have) but also because she knew that Bill preferred women with smaller busts.

I thought she actually looked very good. She was a different style: generous, you might say, and I knew from the rigs that many men appreciated big tits and a big bum.

I told her how sorry I was. Her husband was not the only man in the industry who had some satisfaction with other men when away but went back to their wives. But I couldn't help my attraction to him and also my need to change.

I said I had decided to split up to concentrate on my new life as a woman, probably with no sex at all, and I hoped they could repair their marriage. I knew Bill (as I was careful to call him) loved her, and was desperately sorry that I was the cause of unhappiness between them.

I was crying and she was crying, then things changed.

She was still crying but also starting to giggle. It was difficult for her to speak, but she managed to tell me.

"Bill's brother... we've been...sort of..."

"You mean?" I said incredulously.

"Yes. The thing is he loves my tits, worships them, in fact. It's the compliments as much as anything, maybe even more."

"I mean," she went on, "you've got a lovely bust, and I am sure Bill adores it." She was weeping again.

We were two very different people, yet the same in one way: the sort of person who would fall for William. I realised that it had been more than just being friends with a colleague right from the beginning. And we must both have been the sort of person he would fall for, so there was a lot in our characters the same.

Immediately that was it. We were great friends in a difficult situation, and would help each other.

I was particularly annoyed with him for misrepresenting this lovely woman who obviously adored him. I had in fact made up my mind to send him away to treat his wife as she deserved, until she mentioned the plumber.

It took some hesitant conversations, more tears and about half a bottle of wine before we began to get our heads sorted. I thought I should say it, not her.

"So you wouldn't mind William, that is, Bill, being away sometimes? If Ben was there to look after you?"

"And you knew where he was?" I added. "No pretence?"

She was embarrassed, but yes, she liked what she got from Ben.

William was actually away on a real business trip, and as I had drunk too much to drive, she invited me to stay over.

Curiosity got the better of both of us (plus a bit more wine) and it got to "I'll show you mine if you show me yours!", and we put our busts on display.

Well I have seen plenty of pinups, and I would say if you like big tits, these were excellent. They did not hang down too much, but enough so that you could really see the weight. I reckon most of the men on the rigs would have liked a picture of her up on the wall.

She said mine were very stylish and really suited my frame. She looked closely and felt them, and said the surgeon had really done an excellent job. (I agree, but was pleased to hear another woman say it.)

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