My Boobs & Me - Part 2 (Patreon)

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Then, a couple of days later as I was going to leave, Mr. Carlisle surprised me.

"Harry, I know you've been working really hard recently but we do need to sort out something. Your Geography is coming along really well but there's a problem looming. You have a Project Study to do."

"I know that, I had thought of using the High Street as an example, looking at the building styles and so on, that sort of thing. I thought I'd mentioned that?"

"You did, Harry. But I've been in touch with your school. The teacher there wants to get all the projects started before Christmas. And that should really include yours."

"So what does that involve. Internet searches, I thought, I could do it all on PC."

"You could, Harry, but I must tell you the examiners are not so fond of what they call Net-projects. They like you to actually get into the real world."

"Shit."

"Harry!"

"Sorry, Mr. Carlisle. Maybe I could do it in the evenings?"

"Yes you could, but you really need photographs, you should do it in the daytime. There is a way, Harry. Please don't be surprised, but from what I've seen recently I think you might be able to get away with it."

"Yes?"

"Harry, in many ways, your figure especially, you look as much like a girl as a boy. I don't think it would take much for you to be able to carry it off. I could drive you into town, then you could spend an hour or so on the High Street. With your notebook, and the camera. See what you need to see, get all the data that is and the photos. Then do all the analysis the next day. If you're prepared to do it, that is."

I'd listened carefully to the last part of what Mr. Carlisle had said, then I realized just how he'd started the sentence.

"You mean - dress as a girl, a woman. And go out?"

"Yes, dressed like you are now. Not in that big sweater, those jeans would be OK though. It would just have to be for an hour, Harry. I can't do the actual research for you, it's your project. You have to collect the data yourself. How about next Monday? My other student won't be with me then, she's - er - had to go away for a while. We could spend a bit more time on it then, maybe do some of the analysis later, even."

"Do you really think I could do it? I mean, it sounds a bit extreme really."

"I'm sure you could."

At the end of the week, I had my regular medical assessment, more tests, and measuring. It was Dr. Weston again, she sat down with me after all the tests.

"OK, Harry. I really do think we're coming to the end of this. The swellings have just about peaked and your skin is beginning to clear. Now it won't happen instantaneously but things will change quite quickly. After the next week or so I imagine you'll notice a decrease in the swelling. You might consider a bigger bra in the meantime, in women's terms you are pretty massive right now. Look, let's actually measure the cup size. OK, lift up your arms."

She fed a tape round under my swellings, then repeated over the widest part. She looked at the tape, her eyebrows lifted. "I think, Harry, even just for a few weeks, you definitely need a bigger bra!"

I didn't tell Mum and Dad what Mr. Carlisle and I had planned. Obviously. I mean I did tell them I was going to be out studying all day, just said I had to do a special project, probably I'd go to the library in the afternoon. Which was partly true. As I was leaving the house, Dad thrust a package into my hands.

"Just a small present, Harry, for your tutor. It's only a bottle of wine, not a lot really, but we are all grateful for his efforts. You really have made progress, I'm sure, and an awful lot of it is down to him. Oh, and Mum and I may not be in when you get home, Harry, we're celebrating our anniversary. We're having a long lunch at the 'Regency'. You are OK?"

"Sure Dad."

I arrived at Mr. Carlisle's house a little early. The thought of actually going out in public was beginning to disturb me, I hadn't done that for so long apart from my brief excursions, head down, four or five times a week. And in Marion's clothes too, that caused me concern as well. But at least it was in school time, and none of my friends would see me. I hated to think of the teasing I could get if I got recognized.

It really hadn't occurred to me to ask Mr. Carlisle quite how he knew about make-up, and indeed how he was so good at it. That first time he'd shown me how to do it had surprised me. And I was no less amazed that morning. After I'd changed into my usual lingerie, and put back on my old trousers and sweater, he began to augment the basic make-up I'd done.

"This is probably the best mascara color for you, Harry. You can get it in all sorts of dark colors, this one is an intense blue. I think it will suit the sort of eye shadow You'll be wearing.  OK now, hold still, let me do your eyeliner and just a little eyebrow pencil ... there, that looks OK. Now I'd thought of a rather darker lipstick, what do you think?"

What did I think? How the hell was I supposed to know? "OK Mr. Carlisle, you choose, I think that one does look all right."

He very gently and meticulously, with a brush this time and a small pot of color, spread the deep-ish red paste over my lips, adding another slightly darker color at the edges.

"There. That's a lip-liner, it marks out the edges quite clearly, but I think you need quite a thick gloss coat over the edges, that will look really good."

I looked in the mirror. Yet again I was surprised, not just at the fact that I was clearly wearing make-up, but also that I was doing so very overtly this time. It wasn't just a case of trying to cover over my skin blemishes, which had indeed receded in the previous few days. But I was wearing quite heavy makeup, obviously so, but of course, if people saw me and thought of me as a girl or a woman maybe that would be OK.

I inspected my reflection. I was just going to make a comment about my hair, it was just a little long by then since I hadn't dared go to have it cut for several months. But Mr. Carlisle was ahead of me. I noticed him getting something from a bag beside the chair.

"Right Harry. The crowning touch, literally. This should do the trick."

He had a wig in his hands. Oddly enough I'd not really thought about that. For some reason, my own thoughts over the preceding few days had been concerning my own problems, the breast-like swelling, the skin blemishes, and so on, and the steps I'd taken, with Mr. Carlisle's encouragement, to overcome them or hide them. I hadn't really considered my hair. In some way, I'd just assumed having slightly long hair would be OK, as far as me resembling a woman was concerned, that is.

"I have to admit, Harry, that I bought this some time ago. Somehow I knew you were heading in this direction, that in some way you'd need to resemble a woman more closely to be able to go out in public. Since your hair has a reddish tinge, I know it's mainly mid-brown but there is some red there, I thought long hair, red hair really, would look OK. Are you ready for this, then?"

Mr. Carlisle slid the wig on from the front, trapping my own rather unkempt locks invisibly under the 'cap'.

"It's quite a cheap wig, really, but even so I thought it would look realistic enough, that it could make quite a difference."

He took a brush from the dresser and smoothed the long strands down at the sides and the back of my head, returning to briefly tease the fringe into place. He stood back. "There."

I was impressed. Very impressed. I actually looked female, from the neck up at least. The make-up and wig combination worked well together, looking back at me from the mirror was - a woman. OK, a woman, not a girl, I reckon the overall effect had put about five years on me, maybe as much as eight. Definitely a woman. And as I looked downwards, to see the baggy shape of my sweater and thought about its contents, when the image of my 'breasts' came into my mind, yes, definitely a woman.

"I've put the top and the jeans in the wardrobe, Harry. If you want to change now? I'm just going downstairs to sort a few things."

And, sounding very 'squeaky' I thought, somewhat excited by all this and yet again seeming not quite right in some way, Mr. Carlisle left me in 'my' room. To finish my dressing. My transformation, from a swollen slightly spotty young man - into a woman. I took the hanger with the jeans and the sweater from the wardrobe, then looked in there again. Why wear the same things again? Why not something else? By now I was sure Mr. Carlisle wouldn't mind, and Marion couldn't object, she was half a world away. I inspected the hangers. Quite a few of the things in there were not really suitable, pants which I knew would be too tight, sweaters too, but at the end, my eyes lit up. I put the jeans back.

There was a suit. A sort-of business suit, jacket, and trousers, which looked as if they might fit. I took the hanger out and inspected it. The jacket was a deep blue, maybe it could work, after all, I was wearing blue eyeshadow. It had a somewhat mottled appearance, not just plain blue, with a bit of a silvery glint to the fabric. Indeed, though I was in no way an expert, it looked quite expensive to me. I looked at the label. It was a designer I'd actually heard of. Not one of the top-notch names but someone reasonably famous. Certainly, it would have been expensive. I could wear the jacket over - I reached into the wardrobe again - that blouse. It was a creamy white color, very shiny, maybe even silk, long-sleeved, and hopefully not too tight. Which was good since it would have to cover up my bulging boobs.

I took off my big sweater and slipped the blouse on. Now THAT felt good. I was sure it was real silk, I really didn't know why Marion had left it behind after she'd moved. And it fitted too, quite snugly over my shoulders, it had slightly flouncy sleeves and amazingly it wasn't too tight over my breasts. I was a little worried when I realized my bra was clearly visible through the fine light-colored material but if I was going to be wearing the jacket over it, that should be OK.

I picked up the matching pants and then noticed - there was a button missing from the waistband. I couldn't wear them, I was SO disappointed. I mean, the jacket was fine, I checked that, nothing wrong with it. Maybe this was why Marion hadn't taken the suit with her, at least. I still wondered about the blouse, that seemed fine. But - no trousers. Slacks. Pants, whatever. OK, so the jeans I'd had on the other day would have to do. 'Pity' I thought, I really had hoped to wear something smarter.

Mr. Carlisle had hung the jeans up at the end of the rail. I was just reaching out to get them when I realized there was a skirt hanging next to them. A skirt? Well, why not? If I was going to be pretending to be a female so that I could get my project data, I could wear a skirt. Of course, I could.

Doubts appeared in my mind as soon as I looked closely at the skirt. Maybe there was another one? But I had a good look at the one in my hand first. The color was OK, it was a sort of dark blue, slightly denim-like. And the fabric was basically neutral too, probably just polyester or polyester-cotton. But it looked as if it might be too small for me. I took off my own trousers and stepped into the skirt. It was not that easy to pull up over my bum, it really was rather tight. But I did get it on and fastened at the waist. I looked at the blouse-skirt combination in the mirror. It was rather short but OK, at least it didn't fit into the 'extremely short' category, I couldn't see the tops of my tights below the hem which was about seven or eight inches above my knee.

And with the jacket? I slipped that on and grabbed one of the two shoulder bags hanging on the rail inside the door. I looked again. Perfect. Female. Definitely. I shuddered. This had begun as a practical exercise, it was turning into something more, very much more. I was going out as a woman, OK, but no longer did I just want to 'pass' as female. I imagined myself on the High Street. I didn't just want to look female, I wanted to look good. So there were a couple of other things to consider.

I was hurrying now but still managed to varnish my fingernails quite quickly and effectively, having seen some of the small bottles in Marion's drawer. And jewelry. I knew I'd feel better, maybe even look better, wearing jewelry. I was prepared to be disappointed when I started hunting through the largish collection of earrings, they were all for pierced ears. Then I found one gold hoop with a clip-on, I desperately searched for the other one, hoping I wouldn't find it damaged as I had the suit trousers. I found it.

The necklet and rings were easier, not so much problem there, I just slid three gold rings onto whichever fingers they fitted, and slipped one thick-ish gold-effect chain around my neck. It hung there, its small pendant dipping into my blouse. I undid the top two buttons to show it off, enjoying the fact that it revealed a bit of my cleavage. I stood up. Ready!

When I walked into the dining room Mr. Carlisle wasn't there. I heard a car engine noise from outside and realized he was backing out. I was glad. Though very confident by now, almost proud of my appearance, I didn't fancy public transport. I picked up my project folder and put a couple of pens into my bag. Then I had to go back upstairs to get a few personal items from my jacket pocket. Mr. Carlisle came back in and saw me.

"Well, Mr. Carlisle. Will I do?"

I had expected him to come very close to me, to inspect for flaws, to see if he thought I could pass OK as female. But he just stood there.

"Harry, you look - wonderful."

I glowed. I was so pleased. I had wondered if he'd make a fuss about what I'd chosen to wear, go on about my wanting to wear a skirt, maybe compromising my position and him as well if it didn't suit if he thought I wouldn't pass. But he didn't. He just stood there. He didn't say anything, he was just staring. I walked over towards him, probably for the first time really aware of the effect of my 'boobs' on my general posture and appearance. The bra was doing a great job of showing them off, even through my blouse. And it was doing a pretty good job of controlling them too, as I walked towards him in the short-ish skirt they seemed to begin to wobble up and down. I got the impression that walking like that, in short, jerky steps, they would have oscillated madly without the bra doing its job.

I was going to say something else when Mr. Carlisle interrupted my train of thought.

"Harry. Really. You look incredible. I just thought you'd do the jeans and top, and maybe a little make-up. But this - well, you look gorgeous."

"Mr. Carlisle, really?"

"Really Harry. There is absolutely no way anyone would know. You look totally female. Maybe this is going to be easier than I thought, I was trying to come up with ways of doing the photos and the inspection from the car. Perhaps driving slowly up the High Street."

"Er - you can't. I mean, it's pedestrians only, isn't it?"

"That's why I was having difficulty coming up with some sort of plan. But now, really, there is no need. Nobody will 'read' you."

" What do you mean 'read' me?" I asked.

"Oh sorry. I didn't really mean to say that. What I mean is, nobody will spot you as male. nobody at all."

He thought for a moment. "Unless of course, I call you 'Harry'."

"Sorry?"

"If I call you Harry and somebody overhears, they're going to be very confused. That could be an issue. So, Harry, just in case, you need a female mane. We've not had to think about it before, just the two of us at home if you like, but if you are going out you're going to need a girl's name, aren't you? Any ideas - what would you like to be called?"

So then I had to think. I'd been happy, for many years, with 'Harry'. There weren't so many Harry's around. I was pleased Mum and Dad had chosen that name, not something ordinary like John or Peter. Or even Clyde, apparently that had been in the offing just before I was born. But - a girl's name? I thought about 'Harry'. Something a bit similar, maybe, but not too similar?