My Boobs & Me - Part 3 (Patreon)

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"All right. There was a girl, when I was in junior school, I used to like a lot, she was called 'Helen'. Her family moved away, pity really. But the name's stuck in my mind."

"OK then. Right, Helen. I quite like that. Ready for off?"

I picked up my folder and my 'handbag'. "Ready as I'll ever be."

I was a little nervous even going out of the front door of Mr. Carlisle's house and towards his car. As I approached it, he walked past me and opened the passenger door for me.

"Let's do this right from the word go, Helen. Careful getting in, you're female now. Sit first, then swing your legs in. That's right, well done."

Just sitting in the car as we drove wasn't too bad, I was somewhat hidden from everyone we passed. But when Mr. Carlisle parked at the back of the Council Offices and we had to walk down the narrow street and onto the High Street, my nerves got the better of me.

"Mr. Carlisle. I can't do this. Really. I mean, I want to but I can't."

"Helen. Look at me" he said, standing just in front of me. "There is no problem, believe me. Nobody will stare. Or at least, if they do, the men are eyeing you up, and the woman is just jealous. You look gorgeous. And you've come too far now. Not in distance terms, we've only come a few miles. But in dressing and making yourself up, you've made yourself into a woman. So enjoy the feeling. But remember, we're here to work. You've got things to do. So - OK?"

He took my hand and squeezed it. I realized that people were watching. They had seen what they would see as a symbol of affection. And nobody came over and started going on at me, for going out in public dressed like that. And - one person, a man, probably in his mid-twenties, walked past the two of us. I saw his eyes move from my legs to my cleavage, then to my eyes. And he smiled! I shivered, but I did realize, I could do this.

Though we'd had some doubts about actually how to do this, my project stuff that is, we had discussed in some detail just what needed to be done. So I did it. I actually walked up and down the High Street, slowly at first. Stopping every few yards to make a note about the buildings on the other side of the street, the style of architecture, the approximate age, and the current use.

My project was to be about the 'Built Environment' - an aspect of Human Geography, what buildings are used for, how big they are, not just shops of course, offices and flats and houses and so on. Sure I could get some of the data from the Internet, I would have to, but these observations together with the photographs I took as I walked back down the street, they would form the bulk of my study. And as I walked along Mr. Carlisle stayed a few yards behind me, basically just window-shopping. We'd reckoned it ought to take just over an hour, in fact, I'd got what I needed in about fifty minutes.

"OK, Mr. Carlisle. I think I've done."

I'd approached him looking in a dress shop, of all places, there happened to be one close by as I completed my task.

"Right, well done Helen. So - what do you think of that? The black one, there."

I looked in the Roddhams' window. The theme for the window-dressing seemed to be something like 'Party-wear' or 'Formal evenings' or something like that. And in the middle of the display was a mannequin, surely that should be a mannequin, wearing a tight glitzy silver-colored top, and an indecently tight, short, black leather skirt.

"How would you like to wear that?" he asked. I looked again. Basically, it was a very attractive ensemble. It seemed a strange word for me to use but that's what I thought. And I said so.

"It's lovely."

"And, though I hesitate to say so, Helen, you would look stunning in it!"

I didn't know how to react to that comment. I just looked at it. It really was a very strange thought, to try to imagine myself wearing something like that. So I imagined Holly Tomkinson wearing it. Wow!

"Do you think we'd better be heading home now, Helen?" asked Mr. Carlisle.

I agreed, and we turned and began to walk back in the direction of the car park.

"Shit!" I muttered. Though quietly, Mr. Carlisle heard it.

"Helen?!" he hissed, not wishing to draw attention.

"Mr. Carlisle. Twenty yards ahead, at twelve o'clock. My parents!"

He was flustered. Probably thinking the worst, straight away. He, a trusted tutor, was found in town with students dressed in women's clothes. One helluva scandal. But I reacted quicker, probably a case of needs must. I just had to get by them in some way. They'd just stopped to do some window shopping of their own so I grabbed Mr. Carlisle by the arm and steered him across the road. I let go as soon as I could, and veered into WHS and out of sight of my parents. I hoped.

We spent a minute or two looking at the magazine rack in there. Mr. Carlisle was inspecting one about cars, I surprised myself by skimming through 'Marie Claire', actually enjoying looking at an article by a celebrity about very high heels and how she didn't like to wear them but felt she had to. I asked Mr. Carlisle to have a look outside, and he came back to report that he couldn't see them anymore. I breathed an almost-audible sigh of relief when we got back to the car.

As we went into his house, Mr. Carlisle did exactly the same.

"OK," I said. "That's over. I need a drink." With a combination of relief and, in a way, regret. It was almost the end of term, and after a couple more sessions I wouldn't be seeing Mr. Carlisle for a couple of weeks. No chance to dress me up - had I really just thought that? And why did I feel disappointed about it?

I remembered. "I'm sorry, sir, I forgot. My Dad wanted to thank you for all the help you've given me. He gave me something for you." I tripped up the stairs and came back down with the bottle of wine. "You know, we really are all very grateful. Mum and Dad and me, we all are. Even though they don't know about this stuff today. I'd have had all sorts of problems if you hadn't been there to help. Thank you."

I handed over the bottle. And, while Mr. Carlisle had both of his hands full, I leaned over - and kissed him on the cheek.

"I hope that's OK, sir."

Yet again Mr. Carlisle looked concerned. He did smile a little and turned towards the kitchen.

"Thanks very much, Helen. Now excuse me, please, now I really need a drink after that."

He emerged with a corkscrew and two glasses. "Join me? After the shock of seeing your parents, you could probably do with one too."

We sat in the lounge this time, not in the study-cum-dining-room where we'd always done our schoolwork. I sipped the drink quietly, wondering if Mr. Carlisle was going to suggest we got on with the project there and then. Or should I change out of my feminine clothes first? And what about the project? If I had another drink or two I probably wouldn't be able to concentrate. After a few minutes, Mr. Carlisle offered me another glass of wine. I took it and sipped it, a little more slowly this time.

"Mr. Carlisle. What did you mean when you showed me that outfit in that window. Did you really mean you think it would suit me?"

"I meant it, Helen. You'd look knockout."

"Thank you, Mr. Carlisle. That's a very flattering thing to say. "

"That's OK. Helen."

He was staring at me. I was staring intently at him. I had something to say. "Mr. Carlisle. I've been coming here for over three months now. OK, so you know about my problems. The reason I have to have special tuition, I mean. But I'm a bit puzzled. You obviously are concerned, I suppose that's why you've been so supportive, with me needing to be comfortable and so on. And with dressing up so we could do the project data stuff today. But you've never actually asked to see - my 'problem'. I'd have thought you would have, at some time in all this time, that is."

Now what I did next wasn't really a follow-on from that. Honest, it wasn't. It's just that I was getting a bit warm, what with all the excitement and the glasses of wine. I just stood up and took my jacket off. Just stretched a little, then I realized that in doing so I was giving Mr. Carlisle a clear view of the front of my blouse, and the purple bra showing through it. And of the effect caused by my 'breasts'. However, I continued.

"I saw my doctor again on Friday. Apparently, they are going to start going down. The hormone tests showed that the skin condition has cleared up, but that was always going to decrease first. Now, these - they've stabilized, the doctor said."

Mr. Carlisle stared even harder. I felt he wanted to say something but for some reason didn't dare. I walked over towards him, actually enjoying the sensations I was experiencing as the tops of my tights rubbed lightly against the inside of the hem of my mini-skirt. I deliberately, carefully, took his hand.

"Would you like to see them?"

He gulped. My tutor gulped, visibly. I'd hoped I might relax him by holding his hand but it only seemed to make him more agitated.

"Would you like to?"

"Oh yes. Yes, please. Helen." He was breathing heavily.

"You can call me Harry now, you know."

"I think I'd prefer 'Helen'. After all, you are - you do look like - an attractive woman."

"OK, Mr. Carlisle. Enough of the flattery. Come here."

I led him across towards the door, it seemed a good idea to go through and sit on the sofa. There we could be side-by-side comfortably. I began to undo the buttons on the front of my blouse. Mr. Carlisle was still staring.

"Oh, Helen. They look gorgeous" he said as I pulled the front of my blouse apart to reveal my bra-covered 'bosom' in all its glory. "May I feel them?"

"If you'd like to, yes, of course."

I watched as his hand moved closer and cupped the underside of my right breast. I felt good as his hand began to stroke under the swelling mound. "Do they, I mean, do they - hurt, or ache? What does it really feel like?"

"Oh, no. They don't hurt at all. It was odd at first, with the weight and so on, but especially with this kind of bra, well, they're well supported and don't ache at all. In fact, they feel rather nice. In a strange way, I'll be sorry to lose them. They're a 42 DD now."

"Oh my!" muttered Mr. Carlisle as his hand began to move further around the breast, and to begin to stroke and feel my left boob. It felt good. I said so.

"Here, let me show you."

I un-fastened the small clip between the cups of the bra, releasing my boobs. They sprung outwards a little, free from the tension of the bra. Then, suddenly, they sprung outwards a lot.

"Oh my GOD!" exclaimed Mr. Carlisle. "They are just so beautiful, Helen."

I didn't reply. I couldn't. I was tingling. It wasn't just the breasts that were excited, a shiver was going through my entire body. This was something new. Someone was actually - fondling - that's the only word for it - my breasts. And rubbing his fingers over my nipples. And my nipples were going wild. I'd felt something like this the previous week while the doctor was measuring things, but this was better. Bigger and better. I was shaking with excitement.

"Oh wow. Sir. That really does feel good." I looked down, I didn't really need to but I could feel something extraordinary was going on. Blood was coursing through to my nipples, they were swollen, turning a much deeper red color, and they were suddenly so sensitive. I could feel so much pleasure as Mr. Carlisle stroked them gently.

"I don't understand. Why is this happening?" I think I was almost crying, the waves of pleasure were so exquisite. I looked up. Mr. Carlisle was sitting there, stroking gently. A tear began to roll down his face. I couldn't help myself. I'd kissed him on the cheek earlier, but this time - I just had to - I kissed him. Once, very lightly - on the lips.

He jolted backward. As we parted, his hand stopped moving. We sat very still for a minute. I fastened my bra and buttoned up my blouse.

"Helen. Harry, that is. I know it's nearly the end of the term. Look, this shouldn't be happening like this. It isn't right. I'm sorry. I'm going to ring your school tomorrow and suggest they arrange for a different tutor next term. I think it would be for the best. "

Which is exactly what I didn't want to hear. "Why?"

"Because this isn't right, Harry. Though it's OK to get involved with a student's problems, a tutor should be interested of course in order to provide support. And I am. But I'm rather worried, about what this could lead to. I think you'd better go and change now. I just hope we can continue until Thursday, and get this project sorted before the end of term."

I was really disappointed. I mean, the day had all gone brilliantly, certainly as far as I was concerned. I got up to go up and change.

"Mr. Carlisle. I do understand some of what you've said, but, hell, things seem to be going so well. And if it is the dressing up that is worrying you, maybe I can see why. But I don't have to, if my condition is going to improve soon there won't be a need to, will there?"

"Harry. Please. Sit down for a moment. There's something you should know."

I sat. Mr. Carlisle cleared his throat. He was obviously going to say something very important to him but had some difficulty in starting out. I was unsettled too, obviously.

"OK then. But please, before you start, do you think I could have another glass of wine?"

He got up and poured me another glass. I sat and crossed my legs again, and sipped it slowly. I knew I had to listen.

"The trouble is - Helen - you look so fucking sexy if you'll excuse my language. I'm sorry but I don't know another way to put it, to express what I think. I just don't know if I can trust myself. Hell, I'm not saying this right. Helen, do you know what a transvestite is?"

"Yes, I do. And I do realize, though I hadn't thought about it, right now I'm really a transvestite. Dressed like this, I mean."

"Well, for several years now, since not long after my wife died, I've had a 'thing', some sort of obsession, with transvestites. Not in a big way, you understand, I'm just fascinated. I like to look on the Internet, look at their websites, pictures of men dressed up and so on. Some of them look very convincing, very sexy indeed. "

I sipped my wine. OK, young and somewhat naïve I may have been but I was beginning to understand Mr. Carlisle's situation. And why he had helped me initially, with the ladies' lingerie and so on.

"I have admitted, I've been 'playing with you to an extent over the past few months. Helping with make-up and clothes and so on. And when I saw you this morning, in a skirt for the first time, well, you probably wouldn't understand. But seeing you dressed and made up like that, in your short skirt, I was sexually aroused. And that's not a good thing for a tutor to be with a student. I knew I had to go ahead with our outing but, since then - I think things have begun to get out of hand. I'm afraid - this has to stop."

I got up and walked around a little. I had to think. This did explain a lot. How Mr. Carlisle had been able to help me with the make-up and so on, how he had been able to do it so well. And the frequent looks he'd given me, maybe not quite the looks from tutor to student. Basically, he liked 'Helen'. It was then I realized how my own slant on recent events had changed. I liked being Helen.

"Mr. Carlisle. You said you don't really trust yourself."

"Yes"

"Do you trust me? I mean, you're older. Older and wiser, as they say. And maybe with all the transvestite stuff I didn't really realize what was happening. But - I like being like this. Today has been a wonderful day, maybe except for seeing Mum and Dad in town, that was scary. But just being out, and being looked at, I've enjoyed it. So much. And I may be younger than you but I do know what I'm doing. Maybe it would be best if I stopped dressing up, especially if my symptoms are going to subside. But I'd still like to continue the sessions next term, at least until I can go back to school."

Mr. Carlisle sat thinking for maybe half a minute. "OK, Harry. I won't ring the school yet, we'll see how the next few days go."