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This is a work of FICTION for ADULTS only. Do NOT read this if you are under 18 or if you are not an adult according to the laws of your state or country. Do NOT read this if you are offended by fantasies involving sexually explicit material.
Comments welcome to bethjac@hotmail.com
A series of stories with TG themes, dedicated to women, and to men who like to be women (which includes me!)
H is for Helen - A Very Different Sort of Student
by Bethany Jacques
It really all began in late-ish teenage for me. OK so I realise now there had been signs before that, but I'd not paid them much notice. Little things, significant now that I could put them into context, but seemingly unimportant at first.
The acne started it, typical teenage problem really, with all the raging hormones and so on, it wasn't too bad but it did cause me some concern. Mum and Dad both kept trying to reassure me, tell me that I'd grow out of it and so on, but like all teenagers I thought it was the end of the world. It did hammer my chances with the girls at school, at a time when everyone else in class was pairing off I was at something of a disadvantage.
Eventually my parents decided to do something about it, before at the start of my last year. With exams due at the end of the year and the possibility of college I really did want to do well. I went to the doctors and was prescribed some tablets, nothing really special about that. And they did begin to have an effect, my skin began to clear. OK it may not have been the pills, I was on a health-food kick at the time, salads and low-fat and low-cholesterol foods, anything which might make a difference. My friend Peter said he'd tried some sort of herbal derivative and it had helped him, so I gave that a go.
It was about a month after that I noticed the beginnings of my 'problem'. It had started with a bit of a rash, just itchy, nothing nasty, under my arms of all places. Again I'd gone to the doc and he'd prescribed a mild steroid cream, just to smear gently over the affected area for a week or two.
The itching stopped. And the swelling started. And I began to get hungry, specially for cheese and milk and cream and stuff. I began to put weight on, but not on my waist. On my breasts! The swelling got out of hand quite quickly, after only ten days or so my flattish manly-ish chest was sporting two definite mounds. It was embarrassing! I didn't tell my parents at first, just carried on going to school, wearing a loose sweater whenever I could but things soon couldn't be hidden any more. I just had to tell them.
One evening I did. Naturally they were both very worried, as soon as they saw the evidence, Mum went with me to the doctor's again the very next morning. He was worried too, I think he'd not come across a case like mine before. He referred me as a matter of urgency to the local hospital for some tests, he even rang them up there and then to be sure I could be fitted in immediately. And Mum drove us straight there. They did blood tests, urine tests, various others, rather mechanical really. And then we went home.
It didn't ease my mind when our own doctor rang Mum at home that evening. He'd had the tests rushed through and the results faxed to him, and could we come in again the next morning at the end of the surgery to see him?
"Well, Harry, the good news is that we've got something positive from the results. I admit yesterday I was puzzled but I did some research last night. I found seven cases like yours in the UK, all in the past five years. And every one has been cleared up totally satisfactorily"
"Well doctor" said my mother. "That's a relief. A big relief. So you can suggest some treatment."
"Yes I can, Mrs. Davies. But not yet. That's the bad news. It has happened rather more quickly than in any of the other cases but the blood tests do show that it is totally reversible. The difficulty is that it's going to take a little time, maybe as much as several months, even a year."
"A year! Oh no!"
That was my comment.
"Oh no!" was my Mum's comment.
"Well, maybe not so long. But there have been major changes in Harry's hormonal system, we can't just rush in and try to undo them. It might do more harm than good."
The doctor went on to explain. As some sort of side-effect to the treatments I'd been having, as well as a minor initial condition, I was developing MPMs - 'masculine pseudo-mammaries'. They weren't real breasts, obviously, but they did look like female breasts. It would take some time to settle down my hormones before I could be given the best treatment.
"Look, Mrs. Davies. Like I said, I was worried yesterday but the prognosis really is very positive. By this time next year Harry should be totally back to normal, and permanently so."
We left the surgery, both of us with confused emotions. Dad's reaction was the same when he got home that evening and we told him.
"But what about Harry's exams? OK, he'll be able to do them next June bit this is going to disrupt his education. He won't be ready for the exams."
I was sitting in a large armchair, feeling sorry for myself, and feeling the weight of the two bulges in front of me. "Mum, Dad, there is NO WAY I'm going into class looking like this. I could take a bit of general ribbing, but like this I'd be a total laughing stock. You HAVE to do something about that."
And they did. Give Dad his due, when he decides someone has to do something he will write and call and chase to get it done. Within a week, just before the very end of the holidays, we had a visitor. I didn't really want to see any visitors at that time but Dad had persuaded me, even taken the day off work for it. He showed the man into our living room.
"Harry, this is David Carlisle. He's a home-study tutor. I've got the school governors to fund his coming here, or you going to his house, to give you individual tuition until you're able to go back into class. Mr. Carlisle, this is my son, Harry."
I got up carefully, so as not to cause any frontal 'wobbling' on my part, and shook his hand. Then I sat down again, equally carefully, while Mr. Carlisle asked exactly what stage I was at in my various studies, taking copious notes.
"Well, Mr. Davies. And Harry. I think I can help you. The Maths and Geography and Biology aren't a problem, I've tutored students in all those at this level. And the English Language I know of a decent self-study programme Harry can follow. Maybe one or two afternoons a week. I have one other student at the moment, she sees me each afternoon. So if mornings are all right for you we can go ahead, Mondays to Thursdays if that's OK. Starting Monday?"
Dad and Mum were both pleased, this Mr Carlisle seemed a nice man. And, while I'd been telling him about my various courses and so on, he clearly knew his stuff.
"Harry, you never know" said Mum. "With this private tuition you may be able to do even better in your exams next year." Good point.
The first awkward moment came the following Monday, when we broke for a bit of air in the middle of our Maths session. We were sitting in Mr Carlisle's garden in the late summer sunshine when he asked me if I wanted to tell him just why I was getting the home tuition.
"You don't have to tell me, Harry, if you don't want to. But some of the students I've had in the past like to get it off their chest."
I almost choked on my orange squash!
"I know yours is some sort of medical problem, the school governors told me that when they approached me. You know, I've had pupils with all sorts of problems. Broken homes, drug problems, youngsters with criminal backgrounds. And disabled pupils too."
"Oh I wouldn't count myself as disabled" I said. "Just a very embarrassing medical problem. That's why I wear loose sweaters."
"Yes?"
I decided to tell him.
"I've got a hormonal problem, I've developed female-looking breasts. They won't stay, though, it'll take quite a few months but they will go away. I should be back to normal in a year."
He didn't say anything for a while, he looked rather worried. Anyway, we got on with the Maths. It was on the Wednesday, in Maths again, that he commented again. I was a little unsettled, physically that is, though the worst of my symptoms had lessened since I'd stopped all the medications the acne was coming back again a little and I itched in other places on my body. Not in a major way but the weather was still quite warm and the big sweater and baggy trousers were uncomfortable.
"You OK, Harry? You don't seem it. If you're going to study properly, you know, you really do have to be comfortable."
"It's OK, Mr Carlisle. Just a bit uncomfortable, that's all."
"Uncomfortable?"
"Yes, just a bit tender in some places."
"Can I see?" There was nothing at all untoward in his request. Just a concerned adult, a tutor indeed, wanting to find out what a pupil's problem was. I decided, I had thought about it, to be honest with him, to show him what my problem was. It was indeed the entire reason I was there.
"I need to warn you, Mr Carlisle, I am wearing a bra. It's one my Mum got for me, a sports bra, to try to hold things in so I don't get too embarrassed when I come here." We'd decided, since Mr Carlisle had all his books and stuff at his house it was easier for me to be tutored there, he was only five minutes walk from where we lived and I could manage that. Suitably clothed of course. And in that respect the bra helped, though it really did itch.
I lifted up my sweater to show him. I suppose he could see my 'swellings', the two of them, though I didn't take the bra off.
"And in case you're wondering, they're a 38-C at the moment. The doctor says they'll probably peak at about 42-D and then subside."
"Oh my! And when will that be?"
"A few weeks, maybe months. He can't really tell. But he did say once that starts happening they should go down quite quickly."
Mr Carlisle thought for a moment. He seemed to be day-dreaming. Then he coughed a little.
"OK, Harry, try to concentrate. Meanwhile I'll have a think, see how you could maybe manage things better."
And for a few days that was that, we just got on with the studying. Then one day a week or so later he came up with a suggestion.
"Harry, look, I've got something to show you. It might make things a little better for a while. I spent a rather embarrassing afternoon in the Ladies' Dept in Roddhams yesterday. Please, if these aren't alright please say so."
He took a bag from a drawer in the old-fashioned dresser we ware sitting next to in his dining room. I saw the big green-and-white Roddhams logo. I opened the bag and pulled out the package
'Lingerie set, 38-D, Deep Purple'.
I looked at the label. I looked at the contents through the clear packaging.
"I thought they might be OK. The size is the nearest they had to what you said. And the colour might not be perfect but it was either that or red in that size, I thought that might be best."
I was amazed. Puzzled and amazed. I split open the seal at the top of the packet carefully, I always did that in case the size might be wrong and they might have to go back. I slid the contents out onto the table in front of me. They looked incongruous on top of my Biology folder.
"Well, I think ...."
"That's OK Harry. Leave it if you don't think it's a good idea.
"Er - no. It's not that. I just wasn't expecting this."
"I thought it might suit better than what your mother has got you, that's all."
"Well, it might I suppose."
"OK. If you want to try them on you can go into my daughter's room. I thought it might be more comfortable to wear while you study."
"Your daughter?"
"Yes, my daughter Marion. She doesn't actually live here of course, but she keeps some of her stuff here for when she visits. It's mainly clothes she used to wear when she was younger, she's just never got round to clearing them out. No need to really, they don't get in my way, she lives in London now. She's in Australia at the moment though, back-packing, says she's trying to forget her birthday. It's a special one, you know, one with a '0' at the end."
I thought for a moment. I hadn't asked about Mr Carlisle's family, well, you don't do you? I knew his wife had died quite some time ago. His daughter must be - forty? No, surely not, that would have made him over 60 probably. And twenty was too young, she must be thirty. That must be it.
"OK then. I'll give it a go. Like you said, if it works, ...."
Mr Carlisle showed me upstairs into Marion's room. There wasn't much in there, probably most of her stuff was in London. I didn't look in the drawers or the wardrobe, maybe she'd left some clothes and so on in there. There was just one pair of shoes near the bed, that's all. Anyway I inspected my package again. I looked at the bra, then at the label. '38-D under-wired padded, brassiere.'
I pulled the curtains closed, then took off my sweater and the white sports bra I was wearing. I slipped my arms between the straps of the bra, clipped it at the front and then slid the shoulder straps up into place. And then I adjusted the 'cups' so that my own swollen breasts settled into the right places. It seemed that they didn't really hold things up, then I realised the shoulder straps were adjustable. Again I nestled my breasts in the cups. Now, it made a difference. The straps definitely did support the weight of my 'MPMs' and felt so much better than the white one mother had given me.
I looked in the mirror. Obviously, apart from the silkier smoother texture and the colour, this was an item with a different purpose from the tight-ish sports bra I had been having to wear. This didn't just grab things and squash them in to prevent any unnecessary movement. It was supposed to support the breasts of course, but as well as that it was designed to be attractive, to allow a woman to show off her breasts and her cleavage to an extent. It did push my own MPMs up and together rather, giving me what I could only describe as quite an impressive cleavage. I smiled. I was thinking about Holly Tomkinson in my class, she of the large boobs and prominent nipples. I'd noticed hers from quite close up a few times but she'd have been jealous if she'd seen mine there and then! And I was also thinking I'd like to see her in a plunge bra like mine.
I shook myself out of it, got my thoughts back on track. Basically it worked. The texture of the bra was much nicer next to my rather sensitive skin, and it did indeed support me very comfortably. I pulled my sweater on. Luckily I'd chosen a dark blue one, the bra didn't show through at all.
Then I looked at the panties in the bag, the same purple colour and the same material, but very skimpy indeed. It occurred to me that these might help too. The troubles with my skin had started up again a week or two earlier, again not as seriously as when I'd been on the medications but this time more widespread. Maybe these would feel better than my ordinary boxers? I slid off my trousers and shorts and stepped into them. I pulled them up rather tightly and again fiddled to adjust them round my own , this time male, bodily parts! Indeed they did feel rather nice. Quickly putting on my trousers and shoving my own bra and boxers back into the Roddhams bag, I headed back down the stairs.
"Well, Harry? Any comments?"
"Yes, Mr Carlisle. Thanks for the idea. They do actually feel much better, less liable to rub and cause my skin problems to worsen. Thanks."
"No problem."
"But you really shouldn't have, you know. I'm sure that's not part of your job. You shouldn't have to buy things like that for your students."
"Oh, I'm not paying. I'll put it down as expenses, probably as 'special clothing'. The Authority will pay it. I don't claim big expenses, they know that, they'll probably pay it without even looking."
I just had to smile. "You mean they are paying, basically, for me to have women's sexy lingerie while I'm not attending school. That's weird."
Mr Carlisle smiled widely too though with a bit of a strange look on his face when I'd said 'women's sexy lingerie'. "I suppose it is, I hadn't thought of it that way. Anyway, come on, back to your studies."
"OK. Oh, I tried to leave things tidy in your daughter's bedroom. You may want to check before she comes back, she might get the wrong idea."
Mr Carlisle grinned. "Don't worry, she's not due back for some months, sometime before Christmas I hope."
And we got on with the Biology. The different underclothes really did improve things, quite a lot, I was surprised. And I was also taken aback at the comment I made at the end of the session.
"Thanks for thinking about the comfort thing, Mr Carlisle. The bra is fine, I'm not too sure about the panties. They are rather brief. Maybe having something smooth over the whole of my leg surface might help."
I really couldn't read Mr Carlisle's reaction to my comments, he looked rather uncomfortable himself.
"Sorry, Mr Carlisle. Maybe I shouldn't anyway. But I'd better change before I go home, Mum will probably be back when I get in. Bye sir."
Funny that. I had got into the habit of calling him 'Sir' at the end of our sessions, though it was always 'Mr Carlisle' during them, and when talking to Mum and Dad.
The next day was a Friday, and I went for my medical check-up which I did every other week. This time at the hospital I had two doctors to myself, one an attractive younger woman, the other the same older man I saw most weeks. They tested and measured my MPMs and went into a huddle to whisper something.
"Don't worry, Harry, it's just that yours is a rather rare case" said Dr Hill, the usual doctor. "I wanted Dr Weston to see, maybe give me her opinion."
"Yes Harry" she continued. "I've read up on the literature. As Dr Hill has told you, we're looking at a full recovery in a few months time. I think the swelling has maybe finished, certainly it shouldn't carry on for more that a few more weeks. I reckon your breasts would be a 38-DD at this stage, did your mother choose the sports bra? It seems a good idea. Anyway, how are you doing in other respects?"
I told her about the skin problems, and the irritation I was feeling.
"Well, Harry, I'm sorry but unless that gets really bad you're just having to endure it. I know it's difficult. But your original problem has been caused by the complications in the different medications you were prescribed. I'd like to keep you drug-free, in all respects, for a while yet. OK?"
I nodded my agreement, I could see the sense in that. I put on my big sweater again and went back, head down, out to the car park where Mum was waiting. I could probably have coped on a bus then but I didn't want to risk the ridicule or embarrassment.
At the start of the next week I turned up again at Mr Carlisle's house and started off by presenting him with my Biology homework.
"OK Harry, I'll have a look through it now. Do you want to go up and change? You don't have to, you know."
"No, I'd like to."
"OK then. And there's something else up there you mentioned" he said, burying his head in my notes. I went up. The bra and panties were on the bed. And another packet. A pair of tights. I again looked at the label again before opening them. 'Sheer, black, 10D'.
I put on the bra and thong and then opened the packet. I was surprised at how flimsy the tights seemed, so I handled them extremely carefully. They really did seem silky-smooth, I think because the '10D' label meant they were of a good quality. I rolled up each of the legs in turn and slid it smoothly into place, then stood and pulled them tight.
I was at that moment wearing only that set of lingerie, I hadn't put my sweater on after sorting out my bra again. OK so I'd inspected myself previously in Marion's large mirror when I'd first put the fancy bra on, I was intrigued to know just what I did look like now. AND - I realised - I had to make sure my tights were on correctly. I looked in the mirror.
Wow, what a figure. There was a reaction inside my panties! I just had to stop looking as soon as I'd checked my legs, I had to settle down. I was here to study after all. I put on my sweater and trousers and pushed my feet into my trainers, standing to accustom myself to the rather strange feeling of the tights covering my legs. The feet felt - wrong. They just didn't seem right in my trainers, probably because I wasn't wearing my thick-ish trainers. I would have to put the socks on over my tights.
Then I caught sight of the pair of shoes, probably Marion Carlisle's, which I'd noticed a few days earlier. Though I knew women's feet were in general smaller than men's, these shoes didn't look too small. In fact with thin tights on instead of thick socks they could even fit. I thought of Mr Carlisle's reaction. These weren't something he'd bought for me in order that I could feel more comfortable, these were his daughter's shoes. Yet I really did feel they would do the job, enable me to wear the tights. And that was the point after all, wasn't it? So I'd feel more relaxed despite my medical condition, and be able to study more effectively. Since Dr Weston had said she couldn't help my skin condition with medication, surely I was justified in trying other methods? I had convinced myself.
I put on the shoes. They were, to be honest, just a little tight. But then so were my trainers, I'd almost grown out of them. Mum had mentioned something about getting me some new ones only a few days earlier. I stood up. I walked round a little. I looked down. I was amazed. My feet actually looked - attractive. I'd never ever thought that of my feet before but the combination of the sheer tights and the shiny black high-heeled shoes, I really did think they looked nice. Not just any old pair of feet in trainers. I realised that what I was looking at was basically a pair of female feet. I mean, you never saw male ones like that, did you? And it was that aspect of the whole tights-and-high-heels thing I found attractive.
"You OK, Harry?" called a voice up the stairs. "Come on, time's a' going, I need to sort out one or two things with this Biology of yours."
"OK. Coming."
I entered the room nervously. Basically it was the shoes. I'd been presumptive in trying them on, maybe I'd gone too far. Mr Carlisle and I had a good working relationship, I didn't want to spoil it.
"So how are things. You've got the tights on, I see. Oh my! You've got Marion's shoes on too."
"I'm sorry, it seemed a good idea. The tights are fine but they felt wrong with my trainers. I hoped you wouldn't mind."
"I don't mind at all, Harry. They were to throw out anyway, I'd forgotten about them. Marion told me about them before she left, she says they're the wrong size, not labelled correctly. They're too big for her. If they help you, that's fine. OK now, this Biology, come on. The first section is good but you've got your head round something totally wrong in the second part, look here."
I looked. We discussed. I studied. And I like to think I was doing well. Maybe Mum had been right, I was learning stuff better with a home tutor than I would have done at school. OK so it was only eight hours a week but I did my homeworks and so on. And we carried on like that for four or five more weeks, me changing as I got to Mr Carlisle's house, doing my studying, changing before I went home. And my breasts? They seem to have stabilised. And the skin condition. Well, to be honest it did clear up from my body, but I'd got used to the routine, and really in a way I liked the underwear.
But it didn't clear entirely. It was mid-November, just after the half-term break (which was really boring for me, stuck at home on my own, no lessons, no mates to visit except Jake, my one really good friend). During the week, for some reason, the skin problems returned to my face. Very embarrassing, I couldn't effectively hide it at all. Just walked to Mr Carlisle's house with my head down yet again, I was getting used to that. No calling in at shops or anything, just straight there and straight back afterwards.
"Doctor Hill has promised me she'll give me some medication which should help in a couple of weeks. She's reluctant," I told Mr Carlisle one morning "because my - other problem - seems to be slow in subsiding, in fact - they haven't started yet."
"So you're stuck in - entirely?"
"Yes"
Mr Carlisle carried on the lesson, then stopped about half an hour early.
"Harry, I just wonder. Maybe there is something more we can do to help. To hide the problem, just for a couple of weeks maybe?"
"That would do, certainly."
"Well, it's a rather strange idea but I do think it might work. Can I ask you to try something for me? Come upstairs, I want to show you something in Marion's room. "
We went up, it did seem a little odd, this was the first time we'd both been in there together. Since I did my own changing in there I regarded it to an extent as 'my' room even though obviously it wasn't. Mr Carlisle asked me to sit on the chair, the only chair in the room, and then opened one of the drawers in the dresser.
"My daughter, Marion, she has rather a sensitive skin too. Not as bad as yours of course."
He stopped. "Oh dear, Harry, that sounded awful."
"No, that's all right." I wondered where this was going.
"So she uses a very light form of make-up, something which just does the job, enhances her appearance, that sort of thing. In the sort of job she's in, in PR that is, she has to look good. Well, I just wondered if you'd like to try something like that yourself. Just to see the effect, it's really a good quality product, dermatologically tested and all that. It might help."
I thought for a moment. Makeup? "So what would that involve. I'm not sure that would help. And I'm certainly not sure I could do it properly."
"OK Harry, let's leave it for now. How about we try it just a little at the start of tomorrow's session. You change now, it's almost time, I'll look through these drawers and see what I can find. OK?"
"OK then." I said. "I'll try anything once."
The next morning I went straight up to change. Then Mr Carlisle came in, he brought another chair and sat beside me.
"I don't want to spend a lot of time on this, just a quick go. OK?"
"Sure."
He had arranged quite a few bottles and tubes along the dresser. He started with one flesh-coloured tube, squirting the thin paste onto a sponge and spreading it over my face.
"Here, Harry, you continue, it seems to be covering, and it doesn't look too bad, does it?"
Indeed it didn't. On the one hand it did cover the irregularities in my skin very well, and on the other it gave my face a pleasant sheen. I took a minute to smoothe it into place, then Mr Carlisle took a brush and spread some powder over some areas of my face, basically to give the rather flat surface some sort of relief. Then he got a bigger brush and some deeper pink powder.
"And just a little blusher, I think. OK?"
After that he got a pot of deeper pink paste, basically a lip colour, and applied it very carefully with a brush over my lips, finishing by coating them with a gloss liquid.
"Now, I have to admit, Harry, I think that looks very good."
I looked. I rather liked what I saw. My skin had become rather badly marked over the previous week, Dr Weston had said it was a sign that things were finally coming to a close. But the effect of the make-up was to cover all the flaws, very effectively. I knew I couldn't go out in the street like that, Mr Carlisle agreed, but he was quite happy for me to continue with our studying with me made up. I didn't do it on the next few days, but at the end of the following week I suggested I try the make-up again.
"You want to do it yourself?"
So I did. I managed very well with the foundation, the highlighter, the blusher, then the lip-colourant and the blusher. The result looked - quite good, I thought. Finally I looked in the wardrobe. OK, so Marion's shoes were a little smaller than mine, what about her clothes. I took off my sweater and trousers, and slipped on a pair of her jeans. They were tight, yes, but wearable. I got a sweater too, with a V-neck, again tight-ish. I liked the way it felt. I looked in the mirror. I wasn't hiding my breasts, my cleavage any more. I was revelling in it. But what would Mr Carlisle say?
I walked out of the bedroom, down the stairs, and into the dining room.
"Well, Mr Carlisle. What do you think?"
He looked at me. A strange sort-of glint came into his eyes. "Well, Harry. I see you've decided not to hide things any more."
"Well, just here, Mr Carlisle. I mean, just for today. I couldn't go out looking like this, obviously. But just for in here, I borrowed some of Marion's clothes. I hope, that is, if you don't like ..."
"Harry, it's fine. Really. You look nice. Will you excuse me for a moment?"
He rushed out. He looked weird, like that first time I'd tried on the purple bra, somehow it wasn't the reaction I'd expected. I sat and looked at my books for a couple of minutes before he came back.
"Harry, you look great. Feel like some studying?"
"Definitely."
We actually got through a lot of stuff that session, and in the next couple of mornings though I didn't go so far with the dressing and the make-up. But I just felt good. The whole combination, the lingerie, the tight jeans and more than anything the revealing sweater, they all contributed to a feeling of well-being. We both worked, hard, tutor and student, we made a lot of progress.
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 have to 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 specially, 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 realised 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 be 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, none of my friends would see me. I hated to think of the teasing I could get if I got recognised.
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 colour for you, Harry. You can get it in all sorts of dark colours, this one is a very deep blue. I think it will suit with 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 colour, spread the deep-ish red paste over my lips, adding another slightly darker colour 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 longer 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 it's 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 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 eye-shadow. It had a somewhat mottled appearance, not just plain blue, 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 colour, 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 realised my bra was clearly visible through the fine light-coloured 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 waist-band. 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 realised 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 colour 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 finger-nails quite quickly and effectively, having seen some of the small bottles in Marion's drawer. And jewellery. I knew I'd feel better, maybe even look better, wearing jewellery. 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 round 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, realised 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?
"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 eye-ing you up, and the woman are 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 realised 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 realise, 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, 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 womannequin - wearing a tight glitzy silver-coloured 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 me 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, we turned and began to walk back in the direction of the car park.
"Shit!" I muttered. Though quietly, but 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. Himself, trusted tutor, found in town with student 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, he came back to report that he couldn't see them any more. 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, after a couple more sessions I wouldn't be seeing Mr Carlisle for a couple of weeks. No chance to dress myself 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 - er - 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 if wine. I just stood up and took my jacket off. Just stretched a little, then I realised 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 stabilised, 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 - er - 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 specially with this kind of bra, well, they're well supported, 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 round 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 which 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 colour, 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, this time - I just had to - I kissed him. Once, very lightly - on the lips.
He jolted backwards. 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 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 - what this could lead to. I think you'd better go and change now. I just hope we can continue until Thursday, 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 which 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 realise, 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 web-sites, 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 admit, 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 realised 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 realise 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, specially 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."
I turned and went up to Marion's room to change. That evening Mum and Dad were latish home. I'd done myself a snack, I was just sitting, thinking about how things had developed, waiting for them when Jake turned up at my door. Jake was just about the only real friend I could trust in school, he was the only one I'd told about my own problems in any sort of detail. But even with him I still wore the baggy sweater. And I'd never shown him my MPMs.
As soon as he arrived I realised. The image of my own earrings, worn that morning, for the first time, shot into my head. Or rather Marion's earrings.
"Jake! You've had your ear pierced!"
"OK, Harry. Cool, isn't it? Rib me if you like, but it worked."
"Worked?"
"Yeah. Real cool, it worked on Holly. I'm taking her to the Christmas party. Friday. At the 'Dragon'. Do you think you'll be able to come?"
I'd known he would ask me that. Jake kept going on about how my mates would understand but I knew that wasn't entirely true. Like in any class, there are some all too willing to poke fun at anyone different, whether he has thick glasses, or he's black, or - whether he has big swollen tits. It just wasn't on. I still had to stay out of sight.
I changed the topic again. "So - where did you get your ear done? Was it painful?"
"Only a bit. My mother did it. Cheaper that way of course."
At which moment Mum and Dad appeared. "Hello Jake, how's things?" asked Dad.
"Fine, Mr Davies" replied Jake.
"OK at school? Did you get your Geography project started, Harry's been doing his today?" added my mother. And, as she did so, for a reason I just couldn't see, my Dad smiled as she asked.
"Sure, got it in last Thursday. No problem."
"Harry, you were doing yours this morning with Mr Carlisle weren't you?" queried my Dad. His smile grew.
"Er - yes." What was this about? Surely he hadn't recognised me - no, of course not, the reaction would have been much more explosive. But something was going on I didn't know about.
"We reckon Mr Carlisle has had a busy day, Harry. We saw him in town this afternoon, after we left the restaurant."
"Oh. Did you?" Maybe they'd just seen him, not noticed me.
"You remember he said he has another student, Harry. A girl, I think he said. Well we saw her. She was obviously doing some project or other, she had a clipboard, you know, a bit like yours. They were just off the High Street."
"Was she?" I replied, rather weakly, not at all sure where this was going.
"Pity you've not met her, Harry" continued my Dad, smiling even wider now. "Drop-dead gorgeous, she is."
"Jim!" exclaimed Mum, not too sure about her husband saying things like that, clearly about a young woman or so he thought.
"Well, she is dear. Very attractive, at least. Long red hair, tight top, short skirt, you'd like her, Harry. And gorgeous tits"
"JIM!!" My mother was almost shouting. But she wasn't really embarrassed, she was smiling too. "Jim, I think we'd better change the topic. Jake, I've just noticed, you've had your ear pierced."
Jake told her about it, about his Mum doing it, said it hurt a bit but not a lot. He didn't mention Holly Tomkinson. I was still recovering a bit from my Dad's comments, I was really glad I'd spotted them in town. Clearly he had noticed me and Mr Carlisle. And if he'd got up close to us...... I hated to think. I moved onto the new topic of conversation, suddenly keen to take advantage.
"Maybe your Mum would do mine, Jake. Do you think?"
I waited for my own parents' reaction. They surprised me, I might have expected some hassle. I struck while the iron was hot. Within forty-five minutes I'd gone back with Jake to his house, up the road and round the corner, chatted with his Mum, had BOTH my ears pierced and small 'sleepers' put in, and walked home again. It was dark by then, I was OK with that, specially with my big padded coat on. No problem.
Mr Carlisle noticed, of course, the next morning almost as soon as I'd walked in. But he didn't make any adverse comment, just muttered something like 'very nice'. For the first time in several weeks I didn't go up to Marion's room to change or anything. And we didn't say much about the events of the previous day at first, not about the subterfuge I'd used in order to collect the data for my project. We did deal with the data of course, even though I was supposed to be doing Biology that morning. But he did say something about ten minutes before we were due to finish, we had in fact reached a suitable stopping point.
"Harry, I think you were wise, not to dress up or anything today. We have to get things back on a professional footing, there really could be problems otherwise. Please, what I said, about my liking transvestites and so on, you won't mention that to anyone, will you?"
"No way, Mr Carlisle. Nobody at all, not mates, not family, nobody."
I wondered whether to say anything about my Dad's remarks. I decided I should. He looked rather horrified when I told him, then grinned at the 'gorgeous tits' comment.
"Harry. I think we got away with it. And, though I shouldn't say this but it was worth it. From what I've seen that's going to be a damn good project, maybe an 'A'."
Dad was pleased when I told him that. "Well done, Harry. This tuition thing seems to be working very well. Finish on Thursday, isn't it? Oh yes, while I remember. On Friday Mum and I are off out again. For the night this time. That hotel we had lunch at, they've sent us a special offer, so we're re-celebrating our anniversary on Friday, which is the actual day. And staying there overnight, you'll be OK on your own for the night?"
Friday. So I'd be on my own. Mum and Dad having a sort-of dirty night of it reliving their wedding night, Jake and everyone at the 'Dragon', and me at home with the TV. Oh well. "Sure Dad." I could have said more, but I didn't.
A couple of days later, at the end of our session, Mr Carlisle and I had sorted out the stuff I was going to do over the Christmas holidays.
"Maybe you'll be - partly at least - back to normal by then. Physically, that is. Anyway, Harry, have a good holiday. See you in January."
Mr Carlisle came to the door with me. I was just about to go. But there was something else I'd been thinking about, wondering whether I should say anything. I decided I had to. There may never be another chance. I turned to face Mr Carlisle.
"Sir. Just one thing."
"Yes, Harry."
"I enjoyed Monday."
Mr Carlisle paused. "So did I."
I hesitated again. "Look, sir. You said you like transvestites, you've looked at web-sites and magazines and so on. Well. How would you like - to take me out? "
I stuttered. No. Not that, not go out with Harry. "I mean - take Helen out. On a date, just out to a pub maybe. Would you like to?"
"Well, I'm not sure about that...."
"Oh go on, Mr Carlisle. Look, on Friday Mum and Dad are away for the night." I went on to tell him why, it wasn't really any sort of secret. And I told him about the party. The one I couldn't go to. The one where Jake and Darren and George would be getting very tipsy, Jake would end up feeling up Holly, at least he hoped he would. And there was me, with the television.
"So. Friday. How about it?"
He looked at me. He thought. I mean, I KNEW he wanted to but he was hesitant. A big step, and with a student too.
"Well, since Marion's due back on Monday, this would be the last chance. The only chance really."
"Marion? Your daughter?" Quite why I asked that, I just don't know. He was obviously talking about his daughter. After all, she is the only Marion we had in common. In a sense.
"Yes. She's flying in on Thursday night I think, staying with a friend near Heathrow for a few days. "
He stood still. He was thinking.
"OK Harry. You're on."
I was pleased. Obviously. Like I said, this may be the last chance. And going out on Monday had been SUCH a thrill.
"OK, Mum and Dad are off about half-seven. How about I come here at half-eight, you can do my make-up again, and I can wear that top and skirt again if you like. Get to a pub about half-nine or ten just for half an hour, maybe an hour. How does that sound?"
"You've thought this through, Harry, haven't you? I bet that's why you had both ears pierced, so you can wear one of Marion's other pairs of earrings."
"No, sir. Not at all. Sure I've been thinking about this, but only since Dad told me I'd be on my own tomorrow night. The ear-piercing, well, it was Jake prompted that."
The rest of the day I was on tenterhooks, worrying that Mr Carlisle might ring up and cancel. It was just after eight when the phone rang and Mum answered it.
"Oh hello Mr Carlisle." I heard her say. Bother! He's thought twice about it. "No, don't mention it .... Yes, we really are very grateful .... Yes ... Yes, he's here, one moment."
Mum called me from the hall. "Harry, it's Mr Carlisle. He's just rung to say thanks in person for the wine. He'd like a quick word, Harry."
I took the phone as Mum went back towards the kitchen. "Hello."
"Harry. Can you speak?" An odd question really, then I realised. What he meant was 'Can anyone else hear you?' I pulled shut the door from the living room and spoke quietly. "OK, go on."
"Harry. I've been thinking." And he didn't sound as if he was going to pull out. There was a bit of an excited tremor in his voice. "You said your friends are going to their party at the Dragon? I assume that's the Green Dragon, just off the by-pass. Well, they've got a separate lounge there, a bit upmarket, it's well away from the Function Room. I just wondered if - if you'd like me to take you there - as Helen that is. If that's OK. So maybe you could get here a little earlier, have some time to prepare and so on, I've got something a little special for you."
I had to think quickly, obviously Mr Carlisle had been doing just that. I spoke quietly. "But what if someone recognises me? I mean, they might, Jake or somebody, I don't know, Mr Carlisle."
"Harry. I promise you. Nobody will. I mean, your parents didn't the other day, did they? And really dressed up for the evening, no way will anybody recognise 'Harry'. Trust me."
I did trust him. "OK. So, about eight then?"
"Great. And, just so there's an excuse for us talking, don't forget your Biology homework this holiday. OK?"
Mum and Dad accepted the excuse when I told them, and went on a bit about what a nice man Mr Carlisle was, calling to thank them like that. I was still nervous about Mr Carlisle ringing to cancel, all through the next day. But I have to admit my excitement level rose, even though it was high to start with. 'Something a bit special'? What did Mr Carlisle mean by that? It had to be something to wear, jewellery maybe, or a different top to wear with the skirt I'd worn before? It was just a few minutes after eight when I arrived at Mr Carlisle's front door. He greeted me, obviously still rather excited himself.
"OK Harry, let's get straight on with it. I've got all the clothes ready, in Marion's room of course. Come on, let me show you."
I followed him up, and I really did gasp in amazement when I saw the garment hanging there on the outside of Marion's wardrobe.
"Mr Carlisle! Is that - THAT skirt - and the top as well?" I could see it was. The black one, from Roddhams' window. The one we'd seen a few days earlier. And the shiny silver top too.
"I said I thought it would suit you. Just the thing for an attractive young lady to wear on a special night out. Which this is, of course. I really did think it would be a good idea not to borrow any of Marion's things, I don't think she'd realise, but just to be sure."
I was speechless. Literally. I just touched the skirt, slid my fingers over it, and over the sheer material on the sleeves of the blouse, revelled in the texture, the shape of the bodice, goggled at the incredible plunge neckline.
"You want me to wear - THAT!" Of course I wanted to. It was beautiful. Shiny and silver, a clingy material which would obviously show off my 'assets'.
"Well, Harry. Let's see what it looks like shall we? But I really did think you might want to, after all this may well be your only chance."
"Mr Carlisle. Don't try to tell me you're going to claim that on expenses." I smiled, he laughed too.
We settled down to prepare for the evening. Mr Carlisle had assembled the cosmetics on the dresser. From what I could see he had been spending, I recognised the brand names of several of the items. This wasn't cheap stuff, he'd gone for up-market cosmetics too. I shivered yet again at the thought.
And the surprises didn't end there. Mr Carlisle had a rather self-satisfied smile on his face when he opened the wardrobe and removed a large bag . The first item he pulled out to show me was a new lingerie set, not purple this time but black, and very exotic. It seemed so sheer to me, so smooth, black and ever-so-slightly lacy round the top edges, of the bra and the thong, each with a small jewelled insert, on the bra just above-left of the left cup, on the thong it was on the left too, near the top. They looked lovely. And it had a garter belt too. And stockings.
"Harry. Believe me. Every transvestite in the world, every single one of them, totally loves wearing stockings. And you're going to look great in them. Now, let's begin to sort things. I think it would be a good idea to get the make-up done first, but you may like to shower before we start. We have to get you smelling sweet."
He handed me a robe. Not a pink one, at least. My change-over was about to start but hadn't started yet. I was still male, still Harry.
"OK, Harry, you have a shower. I've left some things in there, gel, foam, whatever. It's called 'White Linen', it's a famous fragrance. Something I used to like to buy for my wife though she wasn't awfully keen on it herself I must admit. And a razor and things. You go and sort that, I'll shower in our room - I mean my room - and get changed myself. OK?"
"Sure, Mr Carlisle " I replied.
He left to do his own thing and I set to my own preparations. I had shaved already that day, twice, but after showering I did so again. I felt clean. Refreshed. And indeed sweet-smelling. Back in 'my' room I stepped into the black thong with its diamante motif, somewhat surprised but delighted that it did its job rather well, its extended job that is. Not just of covering what it might have been expected to cover if worn by a real female, but also that it just about managed to compress and hide my - extra bit!
I slipped my bra into place and noticed it didn't have any shoulder straps. I clipped it in the centre, then adjusted the cups. Of all the items I had tried, and in fact the ones which came after, this was so definitely the best. The very best. Simply, because it worked. It did its job, or rather its jobs. One, even though it was strapless it supported me in a way none of my other bras, not Mum's sports bras, not the purple one Mr Carlisle had got me, had managed to do. My MPMs nestled snugly in the bulging cups, the stiffening and the under-wiring working together to support my bulging boobs. I resolved, there and then, whatever happened that night, to get Mum to get me one just like it or at least get one myself. Maybe white, she would probably not be happy with me wearing a sexy black bra but this one was SO comfortable.
And two, it looked good. Now that aspect, I wasn't at all sure I could convince my mother of. I checked its label. 'Black poly/cotton Bra, 42-DD, Padded, Strapless and Under-wired, Plunge, Diamanté motif'. And plunge it most certainly did, the edges of the cups just manages to cover my enlarged nipples, and in the middle - wow. A cleavage, and what a cleavage. I stood admiring my figure in the mirror for a few minutes.
The suspender belt, by comparison with the rest of my lingerie, was easy to put on. But the stockings, well! They were labelled as 'Nearly Black, 10D, seamed'. They were incredibly sheer, or so it seemed to me. And they felt just plain gorgeous. As I heard Mr Carlisle coming back, I quickly put the robe back on, gathering it at the neck. I wanted to surprise him with the effect of my lingerie, but not yet.
"All right, Mr Carlisle. Barbie doll time again?"
We'd joked earlier about why Mr Carlisle had liked to dress me up, something about him having a full-size Barbie doll to play with, to make up, to in some way 'make' a woman. It seemed a rather insulting thing to say, both about him and about me in a sense, but we both knew we were playing at something. That hadn't been serious. And now, this was. I was going to be his real-life Barbie, his escort for the evening.
"I thought the better-quality make-up might be a good idea, your skin seems so much better now. No need for the medicinal stuff, is there?"
Of course, he was right. No need at all. And good though Mr Carlisle's previous efforts had been, he did an even better job on me this time. He actually showed me a full-page print-out, one which showed a woman - or rather a transvestite - he'd found on the web, one which showed very clearly the sort of make-up he had used and the effect it produced. He was using that picture as some sort of model for me, changing things a bit of course but basically going for that 'look'. Well, it worked. After less than a quarter of an hour he'd finished doing my face. When I looked in the mirror I wasn't that impressed, the hair and the robe didn't look at all feminine. Basically I looked like a young man with make-up on. And a rather silly one at that.
"OK, let's try the wig, Harry."
That made a big difference. I looked again, at the same face, big dark eyes, smooth skin, thick lashes, cheeks lightly highlighted with blusher and all augmented by the same red wig I'd had the previous time. Well, there was a definite feminine feel to the whole 'look'. We were getting close.
"I thought a darker lip colouring this time, Harry, this dark red will match your nails. " Mr Carlisle showed me the pack of longish, stick-on false nails. "OK, shall I do the mouth now? Then you can show me the full effect, lingerie and all."
But I really didn't have time to comment - the phone rang. He seemed annoyed. He was obviously enjoying himself, wanting to see my reaction when he showed me things. But he was interrupted, mid-enthuse, by the phone ringing downstairs in the living room.
"OK. Back in a minute, Harry." I didn't want to look at the other stuff Mr Carlisle had bought for me, I didn't want to spoil his fun in surprising me. But, when he came back up about three or four minutes later, the smile had gone.
"Harry. Sorry, problems. That was my Aunt Harriet on the phone. She wants me to go over and fix her electricity, her power has gone off again. This has happened before, it's only her circuit-breakers but she can't reach them."
"Where is she?"
"Just the other side of Halesowen. It takes me about fifteen minutes to get there."
"And how long to fix it?"
"About a minute. Longer if I let her give me tea. I am SO sorry, this has ruined the evening."
"Why? I can still change, can't I? Now that you've done the make-up. It should take you about forty minutes, if you drive carefully. There'll still be lots of time when you come back. If it's all right, I mean, me stopping here - on my own."
Mr Carlisle thought for just a moment. He didn't take long. "OK." Was all he said, disappearing from sight rapidly, I heard his car start up a minute or so later. I looked round. Mr Carlisle had gone to a lot of trouble. But, if he was an admirer of transvestites, liked the dressing-up and make-up stuff, then he'd probably had a lot of fun, planning things and shopping and so on. OK, so now to add to the fun, to really have a good go at this myself and - I shivered once more at the thought - to be his transvestite date for the evening.
I emptied the bag out onto the bed and began to look through its contents. One item was obvious - a shoebox. As always I looked at the label first - 'Black Patent Classic Pumps, style Stephanie, heel 6 Silver Gloss.' Then I opened it and took the shoes out. They were beautiful! Which is a word I'd never ever used about a pair of shoes before. But this pair were, such high heels, oh-so shiny and with black ankle straps with silver-coloured buckles. I wondered how on Earth I was going to get them on. And even if I did, would I be able to walk in them? The sense of anticipation grew as I looked at the other items from the bag.
I'd had a quick look at the rest of the items Mr Carlisle had got for me, I knew the fingernails, stick-on false ones of course, would take some time. However, I was ready for the main feature, or rather features, the silver top and the tight leather micro-skirt. The first wasn't as easy as I'd thought it would be - until I worked out just how to do it. Or rather how to wear it. The fabric was silver-coloured and stretchy, a little like old-fashioned 'chain mail' but much finer. I slid my arms in and pulled the two halves of the front together, then had difficulties, my long red nails again, coping with the tiny zip up the front. Eventually I got it zipped up, and spent some time arranging the sleeves and the bodice to properly cover my bra. When finally I was satisfied that I was wearing it correctly I turned to the skirt. The black leather was rather more flexible than I'd imagined it would be, this time it didn't take me long to pull and zip it up, just about managing to encase my bum and cover the tops of my stockings.
Then I tackled the jewellery, there were two small boxes, the sort of padded packaging used for that sort of thing. The first was - well - cheap. It even still had its price ticket with it, it was a 'Dress Ring Multi-pack'. But I wasn't disappointed, not at all. £2.99 for what was basically a pack of ten cheap, rather flash dress rings, assorted, not gold or silver of course. The silver-coloured metal ones were probably steel, the gold ones would be maybe brass. And all the 'stones' were glass, of course. But they actually looked quite good. OK, four of them looked awful, and one was badly made, the 'stone' was stuck on way off-centre.
But I chose five of them as 'acceptable', all with silver-coloured settings, and fitted them onto whichever fingers they fitted. The result was - acceptable. Now I didn't know exactly what sort of criteria a woman might use in choosing rings, what type, what should go where, what combinations worked and what didn't and so on. All I knew was that the result looked fine. The five rings enhanced the appearance of my hands, added to the effect of femininity created by my elongated deep-red fingernails.
But the second box - that wasn't cheap. Definitely not. You could tell, the black padded package was of a substantially superior quality. And so were the contents. None of this 'Multi-pack' stuff. The box contained a necklace, and a pair of earrings. Proper earrings, that is, not clips. And these weren't brass or steel, whether they were real silver or just silver-plated I didn't know but they looked good. I wanted to wear them. Big, pendant, diamond-like earrings, with the little hooks pressed through my piercings they dangled about three inches below my ears, glittering and sparking as my head moved slightly from side to side.
I could feel the weight, I could 'feel' the attractiveness when I saw them in the mirror. Even with my newly-acquired long fingernails I managed to fit them quite easily, but the small clip on the matching necklace, that took me several minutes to negotiate. Eventually though it just clipped into place. The overall result, as the heavy gem-studded centre of the necklace nestled against my chest, at its lowest point just dipping into the very top of my cleavage, was very satisfying. Real diamonds even? Maybe. Logic told me Mr Carlisle hadn't just bought this for me to wear for the evening. This had to be his wife's. I felt strangely 'honoured'.
I realised that the fiddling with the jewellery had taken time. Mr Carlisle would be back soon. All I had left to do, basically, was to put my shoes on. Strange how packets and boxes and labels intruded into my life that evening. Basically, I suppose, providing information about their contents which was not at all obvious to a member of the male half of the species. I looked at the shoe-box again. 'Heel 6 inch Silver Gloss'. High heels. Very high heels. OK, if I was to play the part fully, the part of a sexy woman, I had to try this.
I stood the two shoes beside my feet by the bed and slid my feet into them. The fit was as near perfect as I could have hoped for. I'd mentioned to Mr Carlisle that Marion's shoes, the other pair I'd worn, were basically OK but just a little bit tight. He'd obviously taken that into account in choosing these. But where the hell had he got them? I just couldn't imagine myself, Harry that is, going into a shoe shop and buying a pair of Ladies' shoes. Not a pair like this.
Again the long finger-nails gave me a little trouble as I fiddled with the small buckles on the ankle straps. Eventually the first slipped into place, then the second was easier. Then I stood up. Strange. Very strange. Then I moved, the simple task of moving one foot in front of the other. 'Walking' it's called, but this was a different version of the 'walking' I'd been doing for the whole of my previous existence. This was on my toes, nearly, I wobbled a little. Then I got into a 'run', in a sense, took about ten steps across the whole width of the room. This was fun! This was different. And to my surprise, it was nothing like as difficult as I'd imagined. Very quickly indeed, as I tottered back and forth across the room, basic balancing techniques came into play. This was indeed fun. 'OK, Helen' I thought. 'Time to move'.
With my bag in hand, the last of the 'special' items Mr Carlisle had bought for me - or should that be for him - I carefully negotiated the stairs and went into the kitchen. A quick glance at the clock told me he was maybe due back in about five minutes. I wanted to make an impression. Earlier, as he was doing my make-up, he'd shown me some pictures he'd down-loaded of 'Lucy', the transvestite he'd used to model my make-up. In different outfits, of course, and in a variety of poses. But one I'd specially liked showed her sitting on a high stool in a bar, legs crossed, chatting to a man who was clearly very interested in her. In fact he'd had a hand on her exposed thigh. Maybe a little later in the evening .... - hell, what was I thinking?
But for now, I could do that in the kitchen. I filled a glass - a wine glass, that is - with orange squash and sat in one of the two high stools at the breakfast bar. And I heard a car outside, braking rather hard. I crossed my legs. I sipped my drink. I waited. The door opened. I looked up and smiled.
"So, Mr Carlisle, how does your Barbie look tonight?"
Mr Carlisle didn't freeze, he didn't stare, he wasn't rendered speechless. He just grinned, extremely widely. Then he recovered. "Barbie never looked like that! Helen, you look - stunning!!"
Which was, of course, exactly what I wanted him to say. I sipped my drink. "So, Mr Carlisle , are you ready? For your big transvestite adventure?"
"I fucking am!"
After going upstairs himself, to finish dressing, it only took a couple of minutes, my 'date' reappeared fully regaled in dress suit and bow-tie.
"Mmmm. Handsome" I said, and I meant it. Insofar as I was any sort of judge of masculine desirability, he fitted the bill. Nice suit, neat shirt, well-groomed. Yes, attractive. Handsome even.
As Mr Carlisle drove us through the town centre and out towards the by-pass, I asked him about his Aunt Harriet, what he'd done, what she'd said, I really wanted to keep the topic of conversation neutral. I had to try to stay calm. This really was about to be a big adventure. Going into town a few days earlier in a skirt had been one thing, but this - going into a pub so provocatively dressed, this was in another league. And the same pub as all my mates at their end-of-term party, well, the word 'insane' came to mind. But the danger, the risk, the however-remote possibility of being found out, these all added to the experience.
Mr Carlisle pulled up in the car park and got out, coming round to offer a hand to assist me in getting out of the car. We walked together towards the front door of the pub. I was glad to get inside the lobby, it was actually quite cold and I was revealing quite a large amount of bare flesh. Just inside the door Mr Carlisle pulled me to one side. He spoke quietly.
"Harry. Listen, this seemed like a good idea the other day. But - really - we can turn round and go home right now if you like."
I was tempted. This was beyond what we'd done on Monday. So far beyond. Maybe it was going too far. Perhaps we should just drive back and sit in Mr Carlisle's living room, maybe have a drink or two, flash my thighs at him, that sort of thing. Leave it at that. I might have suggesting doing just that if, the very next moment, the main door hadn't opened behind us. And if Darren Harris, class dork, hadn't walked into the pub. Obviously nobody had told him the pub's function room was at the other side of the building, and that you had to use the other door. Or, more likely, someone had told him and the full meaning of the words 'other door' hadn't sunk in.
But it wasn't just the fact that he'd come into that door that decided me, it was what he said a few seconds later. He actually looked me straight in the face as he came in. And then his eyes moved downwards. Somebody, one of the others in his little party pulled him back, realising their mistake, knowing they'd have to seek out the other entrance. And as the door swung shut I heard his voice say "Christ Jake. Did you see those tits, Christ they're gigantic! Wish I could ..." and I didn't hear the rest. But that was enough. I wanted to do this and I knew Mr Carlisle did too.
I moved closer to him. "Mr Carlisle. We're going to do this. But remember, none of this 'Harry' crap. I'm Helen. And, while we are at it, I suppose I should call you David for tonight. Now, come on, just what you've always wanted, going on a date with a sexy transvestite. Like you said, your only chance really so come on."
I took his hand and, with our fingers interlocked and me holding on very tightly indeed, we went through into the bar. Now it would not be true to say that as we entered absolutely everyone turned to look at us and to stare at my boobs and my figure and so on. But, there was a bit of a hush as we strolled across towards the bar, and several men moved out of the way to allow me through. And Mr Carlisle too of course since I was still gripping his hand tightly.
"Half of bitter" he called out as the barman came straight over towards us. He looked at me. All right, we should have sorted this out in advance. "And I think I'll have a vodka-and-tonic this time, darling" I added in response to his questioning look. Trying to give the impression we did know each other and that, in some way, I didn't always have the same drink and he'd had to ask me for that reason. And also trying to keep my voice quiet and in some way 'gentle'.
He paid for the drinks of course, and I settled down on one of the tall stools at the end of the bar, replaying the scene from the kitchen and from the pictures he'd shown me. He leaned over, the noise level in the bar was beginning to rise again.
"Helen, you do realise most of the men in here are staring at you."
I smiled. "Actually Mr Carlisle - er - David, I'm rather surprised at how nice a thought that is. And does it make you feel good?"
"Incredible" was his reply. He just grinned. Stupidly, really, and I told him so.
"David, my darling, stop it, people are going to wonder just what's wrong with you."
"I don't care, Helen. I dare say other guys have had as much fun before walking into a bar with a transvestite, but I guarantee nobody has ever had more fun. And nobody has ever had the pleasure of being with such a fuckable transvestite!"
"David!"
And we just chatted, quietly between ourselves, for maybe half-an-an hour or more, commenting on what we thought about what we'd done and what we were doing, both of us being really rather smug about our 'adventure'. Eventually I decided it would be rather nice to move on just a little, so after David had got us a second round of drinks I took hold of his hand, and began to stroke it gently.
"Helen, please, you really should stop that. Not that I don't like it, or course, but - oh hell, what's the use..."
He took hold of my hand and kissed it!
"David. You really do have to do better than that!" And I leaned over towards him and kissed him! Not passionately, just a sort of affectionate kiss, just for a second or so - but on the lips!
"Is that OK, David?" He looked round, clearly somewhat embarrassed.
"Helen - wow - you do know what you're doing, don't you?"
"I hope I'm exciting you, my darling."
"You certainly are!"
And before he could say or do anything else I grabbed his hand again and kissed it myself, and then laid it on my exposed thigh. "Excited now?" I asked.
Mr Carlisle swallowed a little, not totally sure what was going on and to be honest neither was I. There was a definite excitement here, being dressed so sexily in the bar and flirting with Mr Carlisle. But he realised and I did too that time was getting on.
"David, I think we'd better make a move. It's getting late, I think some of the gang from school may well be coming through to the bar soon, I really don't want to be seen like this - with you, you know."
"Helen, believe me, absolutely nobody will realise."
"Maybe so but ...."
We left it at that and started to get up to leave. I held on to Mr Carlisle's hand tightly again as we moved towards the exit. As we left the actual bar and were just going to go through the main door, a couple of girls came through from the other direction and turned right. I knew exactly where they were going, and a rather naughty thought came into my own mind.
"David, hang on, back in a minute." I released his hand and turned that way myself, following Anna whatever-her-name-was and the gorgeous Holly Tomkinson into the Ladies' Loo! Of course I didn't really NEED to go into there, I'd only had a couple of drinks and anyway we were due to be heading back 'home' very soon after. But it was just the thought - me, Harry, in the Ladies'. Wow!
I went in and was immediately slightly flustered. There was nobody there. Then I realised, of course, this was different. There were four cubicles in front of me, three had closed doors. I went in the other. Now I could have experimented, tried to pull down my panties and pee and so on but I thought it was better not to try. So I just sat there for a minute or so, I heard shufflings next door. I was inches away from Holly Tomkinson with her knickers down! The thought send a shiver through me but I resisted any temptation to look over or under the panelling in there, I just stayed seated.
Then I heard doors opening and water flushing so I pushed the press-button in my own cubicle and opened the door. I could see two girls with their backs to me, leaning towards the large mirrors in there. And the nearest bum to me was Holly Tomkinson's. I walked over to stand next to her, opening my handbag as I went and taking out my lip-gloss. I leaned towards the mirror myself and touched up my own make-up, totally un-necessarily but what the hell. I could see Holly clearly, she hadn't recognised me at all. Well, in that situation, she wouldn't have expected to see me - Harry, that is - at all.
And I enjoyed the sight, staring in front of me, the sheer delight of being able to look straight at Holly's tits. I made eye-contact with her briefly and smiled a little. Then I realised. She was staring at my cleavage too. I glimpsed across from one to the other, there was no comparison. Holly has the reputation in class of being a very well-developed girl in that department but, looking at the two pairs of tits I could see, she was nowhere. The combination of my swollen MPMs and the tight under-wired bra gave me a substantial advantage in the breast area. And I could see, and I'm sure Holly could too, that as I leaned over the weight of my 'tits' was pulling my bra forward and pulling my tits out! I could just see the deep pink circles of my aureoles jutting out above the top of my dress. It wasn't just the thrill of seeing them, it was the fact that Holly was seeing them too! I couldn't resist a slight wriggle, seeing my boobs wobble and seeing Holly gasp in amazement.
I walked out in front of her and the other girl who I didn't really know, hoping Holly was similarly staring at my too-short skirt and extra-revealing thighs. David was waiting - and he was talking to Jake!
Shit! Now what? Then I realised that Jake wasn't alone. He was with Darren, the lad who'd glimpsed me before when he'd come in the wrong door. Actually it was Darren that Mr Carlisle was talking to, though Jake was stood right next to him. I hoped Mr Carlisle was right about my being so well-disguised, I had no choice, I walked up to him and slid my fingers into his. "Hadn't we better be going, darling?" I asked, trying to keep calm and to keep the tone of my voice 'light'.
Both Jake and Darren had turned towards me. And, I'm glad to say, neither of them was really looking at my face. Obviously. That gave me a chance to turn a little and give them a full frontal view, or as near as they were going to get. Mr Carlisle had taken my hint, he began to lead me towards the outside door. I could feel the eyes of the two boys staring at us as we left, and in the reflection from the tall glass panels by the entrance I could see that, even as we walked away, one of them had pushed the door open with his foot. They were both still staring, Mr Carlisle had noticed too.
"I told you, Helen, they have no idea. And they're still staring."
I stopped. I turned towards my 'escort'. "OK then, let's give them something to REALLY stare at."
I still don't really know why I did it. Just seemed a good idea at the time. I slid my arms up around Mr Carlisle's neck and kissed him. Properly this time. I angled my head towards his and planted my lips firmly on his, at the same time running my fingers through his hair.
"Harry" he gasped quietly, breaking the clinch and pushing me away. "We shouldn't be doing this."
"Do you want to?"
"Of course I want to."
I didn't let him argue any more. I just kissed him yet again, opening my eyes to look back as I thrust my tongue into his mouth and felt his hand move up my thigh in response to my ardour. Jake and Darren were in the doorway, staring, while Holly had joined them and was trying to get them to go back inside. But they were too interested, wanting to see as much as they could as Mr Carlisle's hand slid up my thigh and began to edge my skirt higher and higher. When I became sure they'd had a good glimpse of my arse and my panties I stopped. I broke away this time. I just smiled.
"OK, David, darling. Now we can go home."
Mr Carlisle really didn't have an answer, he was in shock in a way.
"Helen..."
"OK, come on" I muttered, grabbing his hand and pulling him towards his car.
We were both quiet after that. Mr Carlisle drove back in silence, we didn't even hold hands as we went back into his house. That final event of the outing had surprised us both. First because it had been so unexpected, I really hadn't intended that at all. And second - it was obvious that we'd both enjoyed it so much. As soon as we went in Mr Carlisle took off his jacket and poured himself a stiff drink. I did too, we sat facing each other, me in an armchair, him on the sofa, recovering. Finally I couldn't stand the silence any longer. I knew what I had to do, what I wanted to do at least. I moved over to the sofa and sat beside him. I reached across and pulled on his tie, easing the knot. I took his tie off.
"Harry, wait."
"Helen" was all I said. I began to undo the buttons on his shirt.
"OK then, Helen. Look - no - wait!" I paused in attending to his shirt. I sipped my drink again.
"Please, Helen. Don't get the idea I don't want you to go on. I mean, that kiss, outside the pub, and sliding my hand up your thigh, feeling your breasts pressed against me, really that is every TV-lover's dream. It was lovely, but I'm just worried what it seems to be leading up to."
"I'm not worried!" I replied, sliding a hand inside Mr Carlisle's shirt, and pressing my lips once more to his. Inevitably he reacted, not this time by pushing me away, quite the reverse. He pushed me down on the sofa, leaning over on top of me and beginning to undo my top, to caress the swelling breasts hidden in there.
"Oh yes, David!"
That really started it. It started both of us off. Or rather it encouraged us, both of us, just to get on with it. Right or wrong, the time for discussions and debate was over. The next kiss was - passionate, there's really no other word for it. Mr Carlisle was realising an ambition, he was groping a transvestite, and not just groping. 'Heavy petting' is I think the right term. His hands were all over my bra, mine were just getting inside his shirt, enjoying and appreciating the masculine musculature. OK, he was no Arnie but his body really did feel good to me.
Then I stopped. We both stopped. We were not alone, we'd both heard something. Outside the door of the lounge, but clearly inside the house. I looked up over my shoulder, the door was opening. And I heard "It's OK, Dad, it's only me. I just thought ...oh Christ!"
And a woman came in the door. It was obvious. This was Marion. Early.
"Er, hello Marion" said Mr Carlisle, quietly, calmly, surprisingly so given the circumstances.
I couldn't see Mr Carlisle's daughter clearly, I was somewhat twisted round on the sofa and Mr Carlisle was still on top of me, my own right leg wrapped round his arse, I'd just been considering just HOW far to go - basically if I wanted his pants off. I think I'd just decided 'Yes'. But things had changed.
"OK Dad, I'll be in the kitchen" was Marion's reply. The door swung to behind her, I just about heard the other door from the hall open. The kettle probably went on.
Very quickly, Mr Carlisle disentangled his body from mine and got up, eager to finish dressing himself and muttering.
"Jesus, Harry" he hissed. "What the fuck are we going to do now?"
I thought. Quickly. I had glimpsed Marion's face just before she had disappeared from view. And it was not a face showing an expression of disgust or disapproval or anything like that. What she had NOT thought was that she'd just seen her Dad fondling a transvestite. Exactly what she had thought, I didn't really know. But it wasn't that. OK then, if I could be a woman in the Ladies' loo in the pub and withstand the scrutiny of Holly staring at my face and down my tits, maybe I could do this. Mr Carlisle and I, both of us, we had nothing to lose.
"DON'T CALL ME HARRY!" I hissed. Not loudly but very definitely. "I'm Helen. Right, and you're David. Now get upstairs quick, pretend to go to the loo or something. And go into Marion's room before she does, re-arrange the make-up and get my clothes out and so on. Then get rid of the lipstick on your mouth and come down when her room is decent enough. We'll sort my clothes later."
"What do you mean?"
"I mean what I say. Come on, David, work with me here. We can get out of this." I turned towards the mirror and began dealing with my own face, wiping the slight mess as well as I could with a tissue and re-doing my own lipstick and lip gloss. "Come on, I've work to do, being your girlfriend. Now scoot!"
I squeezed his bum and shoved him out into the hall, then went through into the kitchen myself.
"Hello, I'm Helen. You must be Marion, I really am so very sorry about this."
Marion looked at me. OK, she'd had a bit of a glimpse when she'd interrupted me and her father a few minutes earlier but this time I was given a more complete once over. "Helen, please, don't worry. It's me who should be apologising for interrupting you two."
She poured and offered me a glass of wine. "Here, you probably need this. And don't worry, Helen, I'm delighted. Dad's been on his own for too long now, I'm thrilled he's found someone. You been on a date?"
"Just out for a drink."
"And, do tell, how long have you two been together?"
We sat there at the kitchen table for a few minutes, enjoying the wine together, while I explained that I'd known David for a few months and that this had been our first proper date.
"So you're not really an item quite yet?"
"Er - not yet, no."
"Helen, excuse me but - it's pretty obvious. I mean you look stunning, really, and no woman would wear a skirt like that or such high heels, or show off her breasts to a man - unless - "
She left the sentence unfinished. And there really was no need to complete it. We both knew. Mr Carlisle chose that moment to come into the kitchen and we all sat around for a few minutes more. Marion explained why she'd come back early, apparently the friend she had been going to stay with in London had dashed up to Newcastle on business. Though she'd left the key with a neighbour for Marion and wanted her to stay there and relax, Marion said she didn't want to stay there on her own. So she'd caught the train to Birmingham and then a taxi and, well, there she was.
"OK, you two. Excuse me being a bit rude but I really am bushed. I'm gonna have to get to bed."
She kissed David on the cheek. "I'll tell you all about Oz in the morning Dad, but I really do need to catch up on my sleep. Good night, you two. Oh, and don't make too much noise when you come up, will you?"
David looked at me as soon as she'd left. He realised the significance of that last remark. "Surely she can't mean - oh cripes, I guess she does."
I stood up and moved towards Mr Carlisle. David. I kissed him too, just as briefly though on the lips. Then I spoke quietly. And with no little determination.
"David. Look. You wanted to meet a transvestite, didn't you?"
"Yes, or course."
I kissed him again, our lips staying in contact for just a little longer. "And you liked helping me to dress up and make up and so on."
"Sure I did."
So I kissed him yet again, this time just teasing his lips open a little with my tongue. "And you've enjoyed taking a transvestite out to the pub tonight, I mean, it was a good date wasn't it?"
He was beginning to tremble just a little, he knew I was teasing, I think he also knew just what I was leading up to. "Jeez, of course, it was real fun."
I kissed him once more, really opening up this time, real French-kissing, he must have realised I was getting aroused too. "And you enjoyed kissing a transvestite outside the pub, and snogging on your sofa?. Despite the interruption?"
He was definitely aroused by now. "Oh my God, Helen, it's been a dream come true. Really."
I held his hand and moved it up to cup my breast. And for the first time I allowed my own left hand to move down, to slide between his legs. I felt his erection. I caressed it.
"So, David my darling. You ready? And you have to be quiet, Marion may well be asleep already."
"Helen, we can't!"
"We fucking can. And we're going to. Look, David, in so many ways I've had a really confusing evening. I was male when I came here, I've been female all evening. And now my boyfriend has an enormous erection. You can't know at all just how good it feels to me to know that it's me who has aroused you. OK, you've satisfied a dream tonight. Well, in a way so have I though maybe I didn't properly realise it."
We were still just standing there, holding hands. I picked up my wine glass, sipped the last of it. No, I wasn't drunk. I knew exactly what I was doing.
"Your daughter is so glad you've got a girlfriend. OK so we have absolutely no idea how long this is going to last. You may never see these again."
I looked down at my bulging tits, straining to escape my lingerie, my red nipples just peeping out of the top of my bra. "But I think we have to seize the day. Or rather the night. I want to do this so much, and I think you do too. Am I right?"
David didn't say anything but his eyes said it all. I turned and went up the stairs, not to 'my' room where Marion was recovering from her long journey but to his bedroom. David stayed down for just a minute, locking doors and seeing to lights and so on. I was standing looking in his long mirror when he came into the room. He slid his arms round my waist, caressing my breasts once more, teasing the swollen nipples through my top and bra.
I turned and unfastened my top, taking it off and then removing my skirt. While I did so David began to undress himself.
I spoke very quietly. "Lie down, my darling." I eased his pants down and saw for the first time in my life a throbbing swollen erect penis. I kissed it, then manoeuvred myself across his thighs so that his cock was between my legs.
"Fuck me, David" I whispered.
The next morning I woke up first. As quietly as I could I crept into the bathroom, stripped and showered and put on my lingerie again. I re-did my face, with razor, make-up, lipstick and so on. Then while my lover still slept I found one of his shirts in his wardrobe and slipped into it. I went down to the kitchen slowly. Marion was there.
She kissed me on the cheek when I went in. "I'm so glad you're still here, Helen. Without asking for any details at all, did you two have fun last night?"
"We did."
David came down about a quarter of an hour later, while I was having toast and coffee with his daughter. He kissed us both on the cheek. "Morning Ladies."
I remembered the night, well, some of it. The delight of David's first penetration of my arse, the ecstasy of his ejaculation, the sheer joy of the second and the third. He'd not had sex for so long, obviously he was making up for lost time. And when I'd woken up I'd gained such satisfaction from seeing his own sated smile.
I had so enjoyed being a woman. And really, was it true that 'all good things have to come to an end' ? Mum and Dad were due back later. They would expect to see 'Harry'. But I didn't want to be Harry. I didn't want my MPMs to subside, I enjoyed having boobs. Enjoyed showing them off, enjoyed their being stroked and caressed. And I enjoyed being shagged. The sex with David had been just brilliant.
So what the hell was I - Helen - going to do?
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