This is the start.
This was me, in the mid-sixties in a minor public school somewhere in England. I've changed names and tried to disguise people, so you can't sue me if you think you recognise yourself. Please tell me what you think; good/bad/write more/don't even bother . . . nickwyatt42@yahoo.co.uk.
Sorry that there isn't much sex until we get to word number 1,500, but this is the truth – and it's stranger than fiction. Now read on . . .
Part One
As was traditional in our Lower Sixth year, we sat our end of year exams relatively early in order that the GCE O and A level examinations could take place unimpeded in June and July. And so we sixteen and seventeen year olds found ourselves finished with the academic year by the Whitsun Holidays in May, and lest the devil find work for our idle hands in the remaining seven weeks or so, we were set to work by the school on essential non-essentials.
Part of the function was to keep us busy, of course, but part of the idea was to entertain and motivate the other years and take some pressure off the teaching staff who were invigilating the exams.
Thus we found ourselves taking games lessons for the lower years, sitting in on prep sessions, and even overseeing discipline and detentions.
Oh, and there was the school play as well. This piece of notorious torture was devised as a way of involving as many of the Lower Sixth in as long a project as possible. From scene painters to props managers, principal actors to members of the chorus, a production of sufficient complexity could involve forty or so boys for weeks on end. The plan was that we would start work as soon as we came back after Whitsun and have the play ready for first performance in mid-July.
We had no say in the selection of the play itself, of course. That was handed down by the head of English, one Mrs French. Now having a female teacher in an all male school was unusual in itself. But a Head of Department was a real rarity, and she was a real harridan. Thin as a stick, pursed lips, tightly drawn back hair into a vicious bun and strict, joyless clothes; Mrs French was no fun at all.
She was ably assisted by Mr Gibson, and wherever Mr Gibson stood, you could find Mr Trelawny (who taught art) right behind; sometimes too close behind. Mr Trelawny was universally referred to as Mrs Trellis, of course.
As we left for the Whitsun Half term Holidays, we were all given instructions and directions for the second half of the Summer term, and that's when we learned that the school play we were to perform would be Romeo and Juliet. Not a particularly demanding play, and plenty of relatively identifiable characters and events. But doing a love play with all-boys would in itself be challenging.
On the listing enclosed, I was down as Play Company, which meant that I was expected to do something towards the performance, and I'd be expected to make myself available for whatever was wanted. No problem: I was a decent painter and I automatically expected to be involved with painting the flats, dressing the stage, even making costumes perhaps. Lots to do and quite enjoyable as well.
We of the Play Company cheerfully assembled on the first morning after the holiday break in one of the rooms behind the school stage where Mr Gibson was already waiting for us.
"Come in! Come along, squeeze in here please, you lot. And do shut up!"
He tilted his head back and peered through his bifocals towards the door. "Who's still out there - is it Wyatt?"
"No sir, I'm over here."
He glanced over towards me "So you are. Well whoever it is out there had better look sharpish;- I'm going to count to five! One . . . Two. . ."
A couple more pupils, Richardson and Smith squeezed in. "That's it sir" called Paul Smith.
Mr Gibson nodded as Smith pulled the door closed behind him. Here in this tiny, wood panelled room were 38 of my school chums and me, facing the most potentially embarrassing or character–building six weeks of our lives.
"At last. Now pay attention, the play is A Midsummer Night's Dream!" He announced.
There were muffled noises of surprise as people were taken aback by Mr Gibson's declaration.
"No, sorry. Sorry, been mugging that one up for Year Five in the Autumn."
He grimaced and pinched the bridge of his nose behind his spectacles. For a moment, he looked down and collected his thoughts.
"It's Shakespeare's Rome-ette and Julio, I think. Or maybe it's Thirteenth Night – Merchant of Croydon?"
We laughed as expected, Gibson had us back on his side.
"I've worked on this list of who I want to do what. I'll read it out, if any of you are not happy with your appointed task - or would like to volunteer for additional duties -" He stopped,, lowered his glasses and grinned around the room at us. "I would be delighted to discuss with you personally later."
"Now. Principal members of the company - or actors, as I should like you to become known. Arkley, Bennet, Brown, Davison . . ."
The list included Hugh Montague - the most handsome lad in the year - and Adrian Stanley of course. Adrian was a beautiful boy, delicate and almost fragrant. His complexion was real 'English Rose' and his skin was almost translucent. His blue eyes, slight chin and pretty mouth marked him out as someone special in my eyes and I had worshipped from afar since I joined the school two years before. I'd hardly spoken to him, but I knew he would be Gibson's choice for Juliet - and I think I envied Romeo.
Adrian was sitting next to Smith AJ on the other side of the room, and now he looked across at me and smiled, for absolutely no reason.
" . .Oh, and you, Wyatt."
"Me sir? I can't act!"
"Then you shall learn, my dear boy. Learn"
Adrian had smiled at me before my name was called. He knew!
"Next, I shall be directing and producing and the following boys will be working with me on scenery, stage and back-of-house:- Bennet, Denby, Carlisle, Evans, Jacobson . . ." And of course, the list ended with me, "Wyatt" again.
"Now the last squadron; the immensely important backroom boys- Administration. Y'know, ticket sales, auditorium, publicity et cetera: Arkley, Brown, Davison, Denby . . ."
Everyone was on two lists. I was on Acting and Production, Stanley was on Acting and Administration. Hugh Montague was on the Acting and Production lists.
"Right! Everyone got that and know where they are or should be? I'm pinning the list up here" Mr Gibson gestured vaguely behind him.
"And this is important! This will be the place where all important information and updates will be posted. I won't be able to talk to you all individually all the time, so watch this space!" And with some theatre, he span around quickly so that his black gown flared out behind him and thrust a drawing pin through the typewritten list and into the pinboard behind him. Pleased with the effect, he stepped back.
"Members of the Company; Actors if you will! We have a meeting in . . . " he flourished his wristwatch. "In ten minutes, in room Q."
Forward to Room Q; where Mr Gibson announced that Adrian Stanley - the perfect Juliet - would not be able to take the part in the production as he was leaving to join the National Youth Orchestra's tour of Scandinavia just before the run concluded, we were all a little nonplussed and disappointed. We all clapped and hoorayed for Adrian, and he nearly cried. I wanted to hold him and kiss those pretty tears way. And then the next announcement from Mr Gibson left me reeling.
"So, Adrian and I have had a careful look around to see who else might be able to take on this fiendishly difficult role - I won't pretend to you, portraying a thirteen year old Italian girl is not going to be easy – we need a consummate pretender or `actor' to carry it off believably. So, after a long deliberation, I decided that Wyatt, I'd like you to have a go."
There was a bit of clapping, but my mouth just sagged open. I'd never done anything like this before. How on earth could Mr Gibson believe I could carry this off? Was I really a `pretender'?
"You'll be playing opposite Romeo, of course. And for that role I've selected Hugh Montague."
We clapped again. Oh thank goodness. It was going to be big, beautiful Hugh. I could believe in him and enjoy whatever contact we were to have.
It must have been the time when I joined the school or soon after, but at one point of a particular school year I realised that Hugh was actually extremely beautiful. It must have been when we were changing from rugby, and either on the way into or out of the showers.
Hugh was taller than me, broad and muscular, and very well tanned, and his buttocks were a delicious, very pale coffee colour in contrast to his deeply tanned back. Once I had taken that in, I was lucky enough to be able to examine his genitals in some detail. They made such an impression on me that I am able to describe them in detail all these years later.
He was circumcised, and his heavy, languorous penis hung over his scrotum like a sleeping serpent. Even in the cold rugby season, Hugh's scrotum remained deeply hung, with its two vital plums swaying loose in the skin bag. I loved the swag lines at each side of his penis that lead down to his bollocks. Even in the coldest months, Hugh's scrotum always seemed to be tropically abundant. As the owner of a scrotum that shrivelled up closed whenever the temperature dipped, I was most impressed.
His pubic hair was mid brown and sprouted in a neat aura of curls around his penis and testicles. Hugh had no other hair on his thighs or buttocks. I know, I checked.
Apart from his genitals, Hugh was most impressively put together. He had strong, wavy brown hair, excellent bone structure and perfectly pretty blue eyes. From the moment I first became aware of him, I was impressed and delighted. And I was not the only one; AJ Smith and Adrian Stanley were equally impressed. In fact, I'd say that AJ and Adrian had been besotted.
Stanley clapped politely when Hugh's role was announced and I noticed that he was watching carefully but obliquely. I knew he and Hugh had been close, probably very close. But I also knew that something had set Adrian against Hugh, but I had no idea what it could have been. Anyway, as far as Adrian was concerned, Hugh was, currently at least, out of favour. Another reason perhaps, why he did not want to play Juliet.
So here we were, a couple of weeks in and just getting ready for the first wardrobe fitting. Mr Trelawny was in charge of the costumes, the self-appointed Wardrobe Mistress, and he took us one by one into the store room beneath the stage where racks and racks of costumes hung on mobile clothes rails.
"Right, Wyatt – or should I say Juliet! We are very lucky as we have been able to borrow the costumes from the Hadfield College production at Easter, So top quality stuff and everything in place – and pretty period-precise too."
I didn't understand that. He bustled me in and steered me by holding me around the waist to a particular place in the racks of costumes.
"Here. We are using historically accurate stuff, so Juliet would have worn a shift and an embroidered dress or gown over the top – bit like the German Dirndl. Now, obviously you are a slightly different shape to her – unless you're hiding some pretty little bosoms in there – eh?"
He looked at me and then grinned quickly.
"So let's get you started. Get all your uniform off, please."
I started to unbutton my shirt. Mr Trelawny was watching; the shirt came off and I started on my trousers. He continued watching.
"That's it. And the socks too, please."
I stood there in my Y-fronts.
"Let's start here."
And he held out two rolled stockings in a thick, cream coloured knitted material.
"Foot in dear boy, and then we'll roll them up."
I was in a daze. I was being helped to dress in the most disgustingly lustful clothing by one of my teachers. A figure of authority was encouraging me in my most sinful perversion. It did not make any sense at all.
Mr Trelawny knelt on the floor in front of me and rolled the thick stockings up beyond my knee and his fingers trailled up onto my naked thigh.
"And the other leg"
Fingers even further up my thigh. They strayed across my underpants, but I couldn't and didn't react.
"Now let's get you covered. No wait, I think you're going to need a bit of padding up top."
He rose and turned away to a holdall on a desk. Rummaging about for a moment, he called over his shoulder "How do you feel about all this, then?"
"Don't really know sir. I didn't expect to be Juliette at all - didn't expect to be acting!"
Finding what he wanted, Mr Trelawney turned towards me again.
"And how do you feel about the costumes? Dressing up." Pause "As a girl."
I was unable to answer. Nothing worked in my brain at all. I had been secretly dressing in my sister's clothes for years; loving the soft caress of her underwear against my skin and experimenting with her make-up. And now I was doing it out loud, with the knowledge and encouragement of others. I didn't dare say how I felt; I simply didn't know what I should say instead or who I could trust. So I said nothing.
"Turn around, now."
He stood close behind me and quickly wrapped something round the front of me.
"Put your arms in each side. That's it, good"
He drew it up my arms and across my shoulders. God! It was a bra!
"This will give you some shape. Takes a bit of getting used to - I expect though. Don't worry, you'll be fine."
He continued his comforting prattle as he clasped the bra across my back and adjusted the straps. Now he wrapped his arms around and lifted the padded breasts to where he thought they ought to be. Standing too close and for just a second too long behind me, Mr Trelawney revealed that inside his grey flannel trousers, he had an erection.
"Turn around for me, Nicky."
His voice had sunk to a scraping whisper; obediently I turned with his arms still around me. At last he released his hold and stepped back to look at my figure.
"That looks quite convincing, I think. Post-pubescent, but definitely a maiden. Lovely."
He said 'lovely', but I wasn't sure if that was applying to the maiden or to me.
"And now, the shift. Arms up and I'll pop it over your head."
The white linen came down to the floor. The previous Juliette must have been a bit taller than me. Mr Trelawney got down on his knees again in front of me and tucked the shift upwards around my ankles.
"A quick pin for now and a hem for later I think, otherwise you'll go tumbling across the stage on your first entrance."
He took a few pins from the lapel of his jacket and worked away at my feet. He shot a look up at me and grinned, and then bundled the shift a bit higher, almost sticking his head beneath the hem.
"I think we're going to need something to keep the stockings up. Lift up the shift a bit for me. Bit higher. Right up"
I held the shift almost to waist level and felt his hands roam up and down my thighs, tugging the stocking hems up and smoothing them into place as I held the shift aloft, his face about a foot from my crotch.
"So let's get rid of these, now."
And I felt his hands shoot up to the waistband of my Y-fronts and in one practiced movement they were down and off.
"Oh no, I must . . ."
"Nicholas, we're going for accuracy here! Juliet wouldn't have worn knickers! And neither should you; but I'll see what I can do to keep your stockings up."
He looked long and hard at my crotch as I still held the shift aloft. Suddenly, I realised what he was doing, and dropped the hem. I took a step back and smoothed the material into place over my belly, looking down at him rather defensively and a bit confused.
He began to struggle to his feet.
"And now the dress." He grinned at me again. It was a sort of green velvet with a tight, high waisted bodice and full skirt, split to just below the knee on each side so that the shift was revealed. And boy, was it ever hot.
We sort of struggled it on with me trying to hold enough of the shift in place to hide my padded chest at the same time. If it hadn't been so embarrassing it would have been funny. Mr Trelawny was happily running his hands all over me chattering away while pulling tugging and smoothing everything down until he felt I was presentable.
"There. Now turn around again and I'll lace you up."
I hadn't really bargained for that, but there was a sort of corset-type stringing to pull the bodice tight around my chest and waist. As he worked behind me, I felt my backbone and shoulders raised and stiffened. And my little pretend boobs were better defined in the bodice.
"Not too tight, but can you breath enough?"
"Just about." I answered breathlessly.
"Quick let's get you in front of the Director; see if he approves"
"Can I see myself first?"
"Mmm, over here's a mirror."
I walked forwards carefully, thinking about the pins in the hem of the shift and suddenly conscious of the fabric on my naked groin. And there I was. My god; there I was. I had a figure with the shift covering my pink stuffed boobs like shapely pillows, they actually looked convincing as a young girl's breasts. The bodice lacing pinched in my waist in prettily, but I didn't have much in the way of hips to bulk it back out again below. Nonetheless, I thought I looked marvellous. I certainly felt marvellous and tremendously excited to be wearing a dress - and a bra - in public and to be admired for doing so. I felt like a glittering princess.
Mr Trelawny rushed and pushed and shuffled me out and into the backstage area where I waited to be presented in costume: in drag: without underwear. It felt exciting. If I turned my torso to the left, the bodice of my dress pulled the shift with it and the rough material caressed my penis as it did so. Turning back the other way produced the same result and in just a minute or so, I had a partial erection beneath my dress. It felt wonderful.
End of Part One
(Part two will be here soon if you like. Tell me what you thin at nickwyatt42@yahoo.co.uk)