Sophie's Story : by (c) Joyce Hamilton. tg mm Mm FM

Like the author, Sophie is a crossdresser, who has affaires with boys, men,           a woman, and a couple, as she grows up.

Sophie was born when I was thirteen.

Remember, or imagine if you can, an age before personal computers, when the 
word  'teenager' did not exist, before the teen-pound, when 'gay' meant 
happy-clappy, almost but not quite before rock n roll.

A wet Saturday afternoon in the Christmas holidays. My room. Me in the 
deep, red-leather armchair I'd had brought up from the Library in the other 
wing of the house. A football commentary on the large, mahogany-cased 
wireless set. My best friend Jack lying on my bed across the room, propped 
up on the pillows, torso bare and his grey flannel shorts round his ankles. 
He's leafing through a dog-eared magazine, once glossy but now creased and 
tatty: he's leisurely wanking, running his hand loosely up and down his 
cock.

His cock is longer than mine, but not as broad. He's 'cut', like me. Most 
boys were then.

He throws the magazine onto the floor beside the bed. 'You'll have to get 
some more cunt books, Simon. I know these by heart...and they're about as 
likely to bring me off as Miss Crabbe.' (Miss Crabbe was the old prune-face 
who ran the village shop.)

'And where will I get more cunt books? You know I knicked them from Uncle 
Richard when he visited last Easter. And why don't you just come-off? 
You've been jerking away for an hour now. You'll wear it out...grow hairs 
in your palm.'

'Fucking boring fucking wet fucking Saturday...nothing else to do.' He 
turned over on his belly, and started to fuck the pillow. I watched his 
buttocks as they rose and fell. White and smooth triangle framing his 
crease, deep healthy sun-tan the rest. More muscular than mine. Each time 
his arse lifted, I could make out the secret rose of his anus. I felt my 
own cock getting stiff. 'Nice tits your sister's got.' He closed his eyes. 
'Lovely bristols. D-cup, or at least C-cup. Huge.' His oh-so-desirable hips 
were moving faster.

'Crap! They're tiny. A-cup. And in any case how would you know, Jack?'

'Fiona showed them to me. Last summer in Nice...on the beach. And she knew 
I was looking, I tell you. Lovely. Big.'

'Bet you they're A-cup. Bet you ten cigs.'

'You're on.' He turned over again, and I could see his red knob twitching 
with the memory of his recent sham-fucking, and probably the thought of 
Fi's tits.

At the end of the corridor was the bathroom my sister and I used. We used 
to dump our dirty clothes in a tall woven-basket that stood in the corner. 
A chambermaid would empty it from time to time. I was lucky..it was nearly 
full.

I came back into the room with an arm-full of silky and lacy underwear, all 
white. 'See, look. The label. It says Silk Handwash. Size 30A.' I threw it 
over to him.' I knew very well the size. How many times, door locked and 
water running, had I slipped it up over my buttocks and arranged it over my 
chest. Slipped on her sexy french knickers, her suspender belt and 
stockings. And stood looking at myself in the mirror, jerking off into the 
sink.

Jack inspected the label. 'You're a devious sod, Simon. Here you are.' He 
threw the packet of Players at me. He was holding the white silk to his 
cheek. 'Smells lovely. Lilly of the valley.' He ran the lace through his 
fingers and then stretched it across his chest. His nipples showed through 
the lace. 'Too small for me. Would fit you, though.' He threw it over to 
me.

As if it were a new idea, I slipped into the bra...and then the suspender 
belt and stockings. I clasped it skilfully...and then her french knickers. 
I posed, one foot on the seat of my armchair. I was very aware my cock was 
as hard as Jack's now, and almost as visible through the transparent white 
nylon of the knickers' crotch. I ran my hands up my thighs, and then round 
to my arsecheeks, lingering at the silky smoothness there. I turned round 
and leant over the armchair wiggling my arse provocatively, lifting one leg 
to show off the fully-fashioned nylons.

Jack was sitting up on the bed now...his cock stretched angry and red in 
front of him. 'Jesus, Si. You look good enough to...'

'Well, why not, Jack?' I was crossing over to the bed, and kneeling beside 
him. 'Come on!'

Me kneeling for the first time, my little heart racing with excitement, my 
right hand reaching down under me and gripping my cock inside my knickers. 
I felt his knob push against my anus, protected from penetration this first 
time by that thin film of nylon. Then the pleasure of his weight against my 
buttocks, his hands on my shoulders as he rubbed his cock franticly up and 
down between my thighs and into my arse-crease. I was jerking hard, but 
knew I didn't want to come until I felt him coming. His delight was 
expressing itself in a string of oaths and flattering comments. I felt my 
heart and my cock would burst together. And then he was coming...I felt his 
open lips on my naked shoulder, kissing and licking me, as the spunk 
spurted, rubbed, spread over my bottom. I came, spurting into the pillow 
under me.

He rolled off me, and I giggled as I used my discarded underpants to wipe 
up our cum. 

'Hey, Si. That beats jerking. By a long road. Fuckin hell that was good.'

'It was good, Jack. Much better than just tossing off. I tell you, I like 
wearing these, too!  But they're soaked. Fucking hell, you got a lot of 
spunk today. I'm covered in it.'

We lit a couple of Players, and smoked, listening to the football. I think 
we both had a lot to think about. Then I undressed and put the laundry back 
where the maid would wonder how my sis managed to get cum on her knickers.

                            

Over the years   I've met a lot of cross-dressers, and between the sheets 
or over a coffee we've often discussed our shared pleasure. Most of them 
have experimented with dressing since their teen or even pre-teen years. 
They say they feel a real sense of appropriateness when they switch sex, 
however temporarily or secretly. But I know I'm different. For me it's the 
lingerie, stockings and high heels, and I know I'm a fetishist rather than 
a true transvestite.  I feel excitement rather than a sense of 'rightness'. 
In fact it is the very perversity of the act of dressing that makes me do 
it. For me it isn't 'natural', but nonetheless very exciting. Well it's 
that and the early experience with Jack, which taught me a lesson I have 
never really forgotten. Dressed in fine lingerie, and with a discrete use 
of make-up, no male I want, however straight, is beyond my reach.

                             

Chapter Two

'You have a good Christmas, Simon?'

'Fuckin awful...You?'

'Ditto repeato. What you get?'

'Fuckin golf clubs. Would you fucking adam-and-eve it. I'll pawn them I 
swear I will.'

'Subscription to Book Club for me. But it's about to get better for you, 
because I got you a present.'

'But we never....'

'It's as much for me as you! Unwrap it.'

'They're lovely, Jack. I held the black satin and lace suspender belt 
against myself...and then the black silk french knickers, and then the see-
through black nylon jacket. They're beautiful...and fully fashioned. Hey, 
and stiletto heels...my size. They're so sexy. Hey look at these.' The 
little black silk bikini panties were crotchless. 'I could hug you.'

'Later, Si. When you've got them on! I thought you should have your own, 
and not just Fiona's.'

He was undressed before me, and sat on my bed while he watched me dress. I 
was flattered to see his cock harden as I pulled the stockings up and ran 
my hands up and down to make them tight, enjoying the glossy finish. 
'Hey...make sure the seams are straight for me.' I stood by the bed, and 
enjoyed the feel of his hands adjusting the stockings, and then fastening 
the clasps. He took the opportunity to squeeze the flesh at the top of my 
thighs, and briefly grasp my erect cock.

'You know, Si, I've been thinking about seeing you in these all the bloody week.' His hands had left my stockings and were making sure my cock was hard.

'Later, Jack. Let me dress first. Which panties?'

'The bikini first, Si.'

My cock stood proud from the waistband as I made sure the thin lace fitted 
properly between my legs and over my bottom cheeks. And then the seethrough 
jacket with its fluffy black trimmings. I stood by the bed, one foot on it in front of him. 'Fix my shoe,Jack. Bit tighter. Yes. Hey! Hands off. Cheeky! I told you to leave that 
till I was dressed!  Now the other one. Hey it's not so difficult as it 
looks.' I was walking easily, and turning round and round to admire myself 
in the mirror I'd had shifted down from an attic storeroom. The shoes 
transformed my legs.

'Come here!' His voice was a tone deeper. I giggled. 'You want me, Jack? 
You think I look tasty? A tasty little tart for randy Jack!' I posed 
again...classic cheesecake pose with my hands on my knees, side on so he 
could appreciate my arse and my legs.

'I said come here!'

I was as eager as he. I lay beside him and he was all over me. 'I haven't 
jerked for a week, so I'm full of spunk for you, Si.' I'm not sure whether 
it was flesh or satin he wanted to feel. Perhaps it was flesh under satin. 
Anyway, his hands were on my bottom, my hips, tweaking my nipples through 
the jacket, rubbing his body against me, his cock hard against mine.

He broke away from me for a second, and I saw he was holding a tube. 'I 
want to try this, Si.' As he was speaking he put a globule of clear gel on 
his index finger, and reached across to touch it into the crease of my 
arse. My greatest pleasure at our first lovemaking had been to feel his 
knob pushing against my arsehole. How much better, now, to feel his index 
finger slip into me, an inch, two, and then right in. He was gently finger-
fucking me as we hugged and murmured to each other. We never kissed on the 
lips, but we were licking and kissing each others' shoulders as we hugged 
and fondled. And still his finger slipped in and out. 

'Stop, Jack. Or I'll come. I haven't wanked for a week either. You'll make 
me come doing that. Shall we...? Would you...?'

'What? You want me to try? That? Really?'

'Let's try. I'm so excited.'

'Kneel, like last time...but no knickers to stop it this time...The black 
nylon makes a nice frame. Is that right? OK? I'm in. God I'm in you, Si. 
I'm in you...I'm right in you. Jeez you look good. OK?'

My groans were pain at first...but pleasure by now. I could feel his thighs 
against my arse, his cock filling me, his hands holding and caressing my 
hips. He was gentle. Too gentle! 'Harder, Jack. Hard as you want....'

It was slipping in and out so easy...and I could feel my cock getting 
closer and closer to coming, even without touching it. I'd never known 
anything like it. His thighs were crashing into me each thrust...harder, 
yes, and faster. And then I heard him coming as he swore and shouted, and 
could feel it suddenly slipping even easier, come flooding down my thighs 
as he pumped me. My cock exploded with that full week of come spurting into 
the bedclothes.

Later, I cleaned the mess up with my (boy's) underpants. We smoked, and 
then we wanked each other...I was feeling just a little bit used up there!
                         

                           Chapter Three 

Back at School for the Spring Term I soon applied what I'd learned with 
Jack. At my School 'Tart' was the word used to describe a pretty boy who 
would give himself as a sex object to more than one lover. Most boys at 
that time had affaires, often masturbating with an older boy they had a 
crush on (we called them 'items'), but only a 'Tart' would take on several 
lovers. At that time fucking was unusual, and, strangely, sucking 
completely unknown. 

I soon discovered that life could be much smoother for a successful tart!

Of course you had to be pretty to be a 'tart', and it did me no harm to 
have such beautiful lingerie! And I loved a prick in my arse!

                    

Sunday afternoon with nothing to do for a couple of hours before Chapel. I 
was walking across the quad when a window opened three floors up and the 
powerful voice of Tom Anderson, Captain of Cricket, echoed across it. 'You, 
boy. Bring some coal up. Chopchop!'

                    

I staggered across his room and emptied my bucket into the coal scuttle. I 
was panting from the effort of climbing the stairs.

'Are you the boy the other boys call Sophie?'

'Yes sir, that's me.' I was making my way to the door.

'No. Put that down and come here.'

I put the bucket down and stood beside his easychair. 'I've heard some 
fascinating tales about you, little Sophie.' His hand was on my thigh as I 
stood in front of him. As he spoke it crept sensuously higher up the back 
of my leg. 'I wonder how many of them are true or how many wishful 
thinking.' His hand reached my panties, which were silk french 
knickers...pale blue as I remember it...and rested on my right buttock. 'Well. 
That's one story that's true, little Sophie. You do wear silk panties. 
Where do you get them?'

'Boys give them to me, sir. Often.'

'So that's another story that's true then. One can only hope all the others 
are too.' His deep voice had a sexy, sophisticated drawl.

I was enjoying this now. His hand was fondling my bottom, up under my 
shorts, and he leaned forward to touch my cock with his other hand, through 
my shorts. I moved a bit closer and wriggled a bit to show him I liked it. 
Not that he was shy...I'm certain I wasn't the first boy he'd 
propositioned! I could see his bulge growing under his dressing gown. One 
of his hands was feeling my bottom, through my satins: I took his other 
hand resting on my fly-buttons and slipped it up the front of my shorts, so 
it gripped my cock...again through my silks. 'I'm sure the stories about me 
are chiefly just stories, sir. But I can see what they say about you, sir, 
is absolutely true.' I leaned forward and opened his gown, so his cock 
stood out proud. Tall..and, wedge-shaped, with a magnificent helmet that 
was nontheless not as wide as the shaft. It immediately occurred to me that 
shape would penetrate easily despite its size. 'I've never seen one as big 
as that, sir...' That was true. So far all my experience had been with 
boys. Anderson was nearly a man. I couldn't take my eyes of it, and 
immediately wondered what it would feel like to have the base of that 
wedge-shaped tool stretching my bottom, its length filling me, its knob 
exciting me as it rubbed in and out.

'Yours seems very adequate, Sophie.' He was gently wanking it now, rubbing 
it through the satin. 'They say you like to be fucked, Sophie. Often and 
hard.'

'People talk too much, sir. But I must admit it's true.'

'And you do it in return for being given lingerie and shoes and things.'

'Yes, sir. I love it. But I do need my finery. I'm afraid some of the boys 
steal it from linen lines in town...but some buy them for me. I'd love to 
have that, sir, for free.'  I touched his cock with a tentative hand, and 
saw it twitch in anticipation. 

'Well,Sophie. Run along and get your prettiest things, and we'll see what 
we can do. Don't bother with shoes, though. I've got you a lovely pair that 
will exactly fit you.'




                          
I stood outside his door, and my breathlessness was only partly due to the 
exertion of climbing the stairs:I kept thinking about that huge prick. I 
had put on grey flannel trousers instead of shorts, to hide the suspender 
belt and brassiere that matched the knickers Tom Anderson had enjoyed 
caressing. My stockings were glossy and fully-fashioned...a gift from 
Philbert, as a token of his appreciation for a night spent in his bed...and 
at least three visits to my bottom.

Anderson had removed his dressing gown, and was waiting for me naked, 
leaning on the mantle-piece smoking a cigarette. One thing about schools in 
those days, all that sport and healthy exercise produced young men with 
extraordinarily beautiful bodies. I can see him now in my mind's eye.

In the 'fifties there was a magazine called Health And Efficiency. It 
pretended to be a nudist publication, but its main purpose was to provide 
pictures for boys to jerk off to before the launch of Playboy. The girls 
were airbrushed...no hair or cuntlips...and the boys always had a leg or a 
book or something hiding their cocks. But in that pose Tom Anderson looked 
to me like one of their beautiful young athletes: and he had the same 
immediate effect on my cock as I saw him standing there. Like those pics he 
was suntanned except for the white of his belly and hips, where summer 
swimming trunks had discretely hidden his pride. No hairs on his chest, and 
the sandy wisps of hair around his cock did nothing to diminish the effect 
of it as it pointed towards me, magnificently erect. Shoulders, arms, legs, 
belly...all were hard, slim and muscular. I could hardly wait! 

Without being asked, I kicked off my shoes, pulled my shirt up over my 
head, undid my belt and lowered my trousers. And there I was. Sophie!

'Your present is on the bed, Sophie.'

I opened the shoebox. 'Oh, they're lovely, sir.' Silver high-heeled 
slippers. Mules, with no straps, but a line of glittering diamonds across 
the front. I slipped them on. Perfect fit. I walked towards him, conscious 
that my legs and bottom would be even more appetising as the four-inch 
heels altered my posture. 'They're perfect, sir.'

'And so are you, my little darling.' He took me in his arms, and I could 
feel his cock against my belly. He was at least a foot taller than me, and 
he leaned down as if to kiss me. As you know, I wasn't much into kissing 
yet, and I turned my face away, instead licking and kissing his nipple, 
feeling it harden under my lips. His hands were on my bottom, and mine on 
his. He laughed, and picked me up bodily, without effort, carrying me back 
to the bed.

On the bed we lay together exploring each others' bodies...mainly handling 
each others' cocks. He must have done that so often, with so many 
boys...but not with one so seductively dressed, and perhaps not as a 
prelude to more serious sex.

'I've never done this before, Sophie...'

'Never mind. Just treat me as if I was a real girl.' But suddenly I 
realised that not only had he never buggered a boy, he had never fucked a 
girl either. My heart leapt. The great Tom Anderson was a virgin...and he 
was my virgin. 'I'll show you. Have you any oil or something?'

He jumped as if scalded. As if I had caught him out in his planning of this 
seduction. 'On the shelf there, beside you. It was an expensive scented 
oil, from Willoughby's, the department store in town...where he must have 
bought my mules...which I was still wearing in the bed. I told you I was a 
Tart!

I uncorked it, and put a little dab in my arse. Then poured a handful, and 
re-corked the bottle. His cock now! I spread the oil, and treated myself to 
fondling his balls as well...scarcely more hairy than mine. Later I would 
shave my pubes daily...but at that time it was hardly necessary as my 
blonde hair was very fine. His cock glistened as I ran my hand voluptuously 
up and down it.

Still holding his prick I rolled over on my back. 'On top of me lover...and 
have me. I'm so wanting you.' I bent my legs up...I was very lithe in those 
days, and as he lay on top of me his knob pressed against my anus...just as 
I so liked. I was still holding it, my hand under my leg and between our 
two bodies. 'Now push!'

'I sighed and moaned as the long shaft slipped in, easily at first, and 
then more laboriously as my anus accepted the uncustomary breadth of his 
tool. He looked alarmed at my moan. 'Don't stop! More. Right in. It's 
lovely.' And his body rested against mine, his cock completely held by my 
anus and rectum. 'Now fuck me!'

It didn't take him long, of course. But he was energetic and very strong.  
All his energy was in his hips and cock...there was no fondling or 
caressing, and he hardly looked at my body as he fucked me. Normally I 
would like a bit more 'play' and a longer, slower build-up. But this virgin 
was very exciting, and as I saw his face redden and his eyes close with the 
power of his coming, so I came off too, spurting between our two bodies as 
he filled me with cum. Another one who had been saving it up for me, I 
thought contentedly.

I cleaned us up. He smoked, but did not offer me one. 'Mullins wants to 
have you as well, Sophie.'

I must have made a face. 'You don't fancy Mullins, then?'

'He's rather an ugly brute...not like you.' I kissed his flat stomach. 
Mullins was a rugby forward. Short, squat, very heavy-bodied, pug-faced. 
Immensely strong.

'You'll like his prick though. It's huge. Much bigger than mine. Believe 
me, I know!'

Of course, Anderson and Mullins must have been an item when they were 
younger. Mullins would be at least a year, perhaps two older than 
Anderson...he was thick and would have repeated a year or two. With his 
strength and forceful, bullying personality he might well have appealed to 
the young lad or maybe forced him to play. Whatever...they had indulged in 
mutual masturbation.

I wouldn't let Anderson down. 'Tell Mullins there's a white satin basque in 
Willoughby's window, trimmed with coffee coloured lace. If he gets it for 
me, size eight, I'll wear it for him...all night if he likes.




                              Chapter Four 

I hated Rugby and Cross Country, which were the Spring Term sport 
options..every afternoon except Sunday. So I was overjoyed when my Senior 
lovers got together and had me excused all sport 'on health grounds'. So 
what with one of the Seniors every afternoon, and one of my Housemates 
every night, I was getting more sex in a month than most get in a lifetime.

My wardrobe of pretties and my collection of jewellery was growing all the 
time. At the sight of an erect cock, mine sprang to attention...and when I 
was excited my arse would twitch open of its own accord. I was a very 
successful little 'tart'. 

I had just spent a happy couple of hours between Lunch and Supper with 
Ponsonby. I still had my lingerie on under my shirt and flannels, and was 
carrying my shoes (the 'Dazzle' mules Anderson had given me) in a paper bag 
as I made my way back to House.

'You there, Boy! It's Montrose isn't it.'

'Sir.' The shout had come from Cannon Runcible, our Housemaster. 

'I need to speak to you, Montrose.' I followed him to his room. He shut the 
heavy oak door behind him, and then, unusually, the lighter inner door. I 
heard the lock click on this as he did so. So, as I stood in front of his 
desk, I knew something a bit unusual was going to happen.

'It's got to stop, you know!'

'Sir?'

'You know perfectly well what I mean, Montrose. I turn a blind eye to a bit 
of fumbling and fondling, a bit of innocent hanky-panky among the boys, as 
you know. But this is really too much.'

'Sir?'

'I mean, knife fights... Too much. Just too much...'

'Knives, sir? 

'Anderson and Mullins have fought...over you...and Mullins pulled a knife 
on him.'

'Was Anderson hurt, sir. Oh I do hope he's all right.'

'I expect you do. And that does you credit.' A smile crossed his lips, and 
I realised I wasn't really in too much trouble. 'He's all right, but he 
broke Mullins' wrist. The wrist with the knife. I've had to send Mullins 
home...he started it. And now I have to decide what to do with you.'

'It's not my fault sir. I don't show I've got favourites. I like Anderson 
and I don't like Mullins...but I still let Mullins.... Well, he gets what 
he wants. And I only let Mullins do it because Anderson asked me to.'

Do what? Do what boy?'

I was silent, embarrassed.

'Do what, boy?' He got up, came round the front of the desk and stood over 
me. 'Do what, boy? Spit it out.'

'Have me...sir, have me like the Greeks used to. Sir, in my bottom, sir.'

'Who told you the Greeks did that?'

'Everyone knows, sir.'

'I suppose they do. Yes the Greek men and boys did that...all of them... 
but for some strange reason it's frowned upon in this country in our 
times.' He was musing to himself. 'I wonder when that happened...when it 
went from being a harmless and pleasant pass-time to being a cardinal 
sin?... Must research that one day...But to the point. Montrose, the boys 
call you Sophie?'

'Yessir.'

'And you dress as a girl for them?'

'Sir.'

'And do you feel like a girl, Sophie?'

'Not really, sir. I like to feel silk and satin, and to look at myself. And 
I like to get the other boys excited, and then satisfy them. I've got my 
lingerie on under these, sir.'

'Have you, indeed. Well, Sophie, I think I should have a look.' He leaned 
over me and loosened my tie, undoing the top button of my shirt. I giggled 
and let him continue, not helping him. The tie fell to the floor as he 
popped my buttons, Finally my shirt slipped from my shoulders and hung down 
from the waistband of my trousers. I remember I was wearing a black nylon 
see-thru top...so tight across my chest that my nipples made lovely little 
bumps in it.

'Quite, quite charming,' he murmured as he fumbled with the buckle of my 
belt. He succeeded at last, and trousers and shirt fell to my ankles. I 
kicked them away...and my shoes too. I recall I was wearing glossy tan 
stockings, a black satin suspender belt, and matching french knickers. 
Without a word I took my shoes from their paper bag and slipped them on.

'Delightful! Quite, quite delightful. I was never a lady's man, Sophie, but 
I find you quite, quite delightful.

I could see he did...there was a bead of perspiration on his forehead...and 
his hard-on was making a tent in his clerical surplice. He had pulled me 
close to him...I could feel the rough cloth of his hassock against my 
cheek, while he caressed my bottom, muttering to himself all the while, in 
a world of his own.

'But what shall we do with you, Sophie? Pretty little Sophie. Greeks, 
indeed! Knife-fights! They fought over Hellen of Troy, Sophie. And they 
fought over you, you little darling. No! There's no alternative. I shall 
have to punish you....'

'Oh no, sir. Not the cane....'

'Spanking, perhaps. This pretty little bottom and its pretty little 
knickers.'

'Woodson spanks me, sir.'

'Then that is what we shall do, Sophie. But you will tell the boys you were 
caned for causing a fight.'

He lay me over his knees. 'Your hassock is terrible rough, sir. On my skin. 
It would be nicer across your bare knees...like Woodson does.'

'It would indeed.' He was pulling his skirts up, under me, and they made a 
great roll of cloth between my body and his belly. 'No good at all...no 
room to spank! All off!' He heaved the whole lot off over his head and they 
joined my bits and pieces of uniform on the floor. Except for his black 
socks and shoes he was naked...and I could feel his hard cock pressing into 
my belly...mine too against his legs, to be honest.

He fondled me with both hands before the first slap, his hands round and 
round my arsecheeks, and then his fingers slipping just under the elastic 
of the legs. The first slap was a light, playful affair, but I wriggled 
nonetheless, as I knew he wanted.

More caressing, his hands venturing under the satin now, handling my bare 
bottom. The second slap harder, but still playful. More caressing. His 
finger reaching into the crack of my arse...still slightly relaxed and oily 
from my earlier frolics. Another , heavier slap, this one stinging and 
making me squirm genuinely. One hand on my naked arse cheek, under the 
satin, and the other index finger tip-tapping against my anus. The heaviest 
slap yet. I feel him pulling my panties down to my thighs. Handling me more 
roughly now, squeezing and kneading me.

'Woodson puts his finger right in me when he spanks me, sir.'  I wriggled 
provocatively.

'Does he indeed?' He sounded disapproving, but his finger slipped easily in 
me, as his other hand fell like a thunder-clap on my naked bottom. 

'I like that, sir!' Another thunderclap.

'Plese, sir. Put your thing in me...I mean right up me...'

Wordless, he stood up and carried me to the great green-leather sofa. I 
knelt where he placed me...and he was behind me and in me in a moment. I 
still had had only a glimpse of his cock, but knew I would have no problem 
with it. Frankly it was smaller than most I enjoyed...and rather battered 
in appearance. Still, he made up for that with the energy he put into 
fucking me. I'm afraid I came all over his shiny leather, and it was a 
minute or two, with a lot of groaning and panting that he came as well.

Some men are remote after sex. He was tender. As we stood, he bent down and 
kissed me lightly on my forehead. 'We shall do that again, Sophie. And I 
shall invite Fanshaw...would you like that?'

Fanshaw was the new Biology teacher...a tall, rangy, muscular Australian. 
'I would indeed sir. I didn't know you and Mr Fanshaw were an item, sir.'

'Nor must anyone else, Sophie.' He laughed. 'Let's just say he studies 
Greek with me.' 



                    

 Chapter Five


I don't count childish fumblings with Jack and other school-friends as 
anything other than sex. My first experience of the real thing was with the 
first person I ever fell in love with, when sex was deepened by emotional 
involvement. His physical type has remained my masculine ideal all these 
years, and across all these different bed-partners.

I was fifteen in the summer of 1960. I had been on holiday with my parents, 
camping in France, and was coming home early, by myself, for something (I 
forget what) at school.

Most of the passengers on the ferry were dressed casual...in my case 
downright scruffy, though I expect I looked quite seductive with my deep 
suntan and faded blue jeans. Photos of me from that summer show a slender 
and willowy lad, with golden, sun-bleached hair, curly and not at all the 
short-back-and-sides de rigueur for the next few years. Also a provocative 
way of standing with his pelvis pushed slightly forward to force the 
watcher's attention to the interesting bulge that seems to figure in every 
picture. Michel was the exception to the general casual scruffiness. I 
never saw him anything but immaculately turned-out, and that day he had a 
grey silk suit, highly polished shoes, and a silver tie, exactly matching 
the silver of his wavy hair. I noticed he had a gold watch and a gold 
ring...on his little finger. He was manicured, polished, groomed. And he 
flattered me by talking to me in French, and treating me as an adult whose 
views were worth listening to. No, he didn't try to pick me up then and 
there...though I might have been willing. He was a radio producer with the 
BBC Overseas Programmes, and he took my telephone number in case they 
needed a student with fluent french for a show.

It was just before Christmas he called me at home. The programme was a 
discussion about the political situation in France. It would take two days 
to make, and the pay would be fifty pounds. Doesn't sound much now, but 
believe me it was then. My dad was rich, but not over-generous with my 
allowance.

We recorded on a Friday afternoon, and I enjoyed doing it. Michel was very 
much in control of his programme-guests. I remember a fierce woman lawyer, 
and a backbench MP (who many years later was 'outed'). After, he took me to 
a fish bar where we had oysters and white wine. Then to a pub in Soho for a 
few drinks. In those days there were only a few gay pubs in London, and 
this was one of them...gay sex was still illegal. He was showing me off to 
his envious friends. I was pretty, wavy blonde hair, and still tanned from 
the summer. His media friends kept drifting over to chat. The conversation 
was intelligent and witty....with lots of sexual undertones and innuendos. 
I flirted openly with them, to Michel's delight.

I knew he would make a pass at me, and was happy just being passive and 
waiting for him to move. At his flat I showered after him, and when I 
returned he was, like me, in a fluffy, white bathrobe. He had shaved again, 
and brushed his hair till it shone silver.

'Only one bed, I'm afraid. I'll sleep on the settee if you like...'

'No. That's all right, Michel.'

'And only one pair of pyjamas. I'll have the tops, you the bottoms...'

It was not a question, this, and as he turned back the green satin 
bedspread I pulled up the grey silk pyjama trousers, and threw the robe 
across a chair. I slipped into the bed, and watched as he too took off the 
robe and did up the pyjama jacket. He may have been in his fifties, but he 
had a good body, I thought. As he stood by the bed I took in his very 
white, trim buttocks, long, slender legs, and above all his cock, semi-
erect, and arching so gracefully. I saw he had been cut, like me. He was 
not as long as Jack or as broad as me. But there was something elegant 
about that cock, like everything about him. I was hard now.

He lay beside me, and must have read consent in my eyes because, without 
speaking , he took me in his arms and kissed me very passionately. I was 
squirming against him as his hands caressed my bottom (inside those stupid 
pyjamas). I could feel his cock hard against mine. 

'Have you done this before, Simon?'

'No Michel...not really.' It was a lie, but a white one! And I really 
hadn't often kissed!  'No, don't stop, Michel. That's nice.'

'My little darling, my sweetie....' His hand was on my cock now, as we 
kissed, and I felt for his.

'Fuck me, Simon. Fuck me with your lovely cock.'

'I've never....'

'I'll show you.' He reached for the bedside table and was rubbing gel on my 
cock. He lay on his back, pulling me on top. Then he raised his legs, and I 
felt him grasp me, under us. I pushed, and I was in. I'd longed to 
fuck...we still called it buggering back then...and I paused to savour the 
moment. All those times I'd been fucked...I felt proud. I was adult, an 
active fucker. This was the real thing. 'Hard. Fuck me hard.' He was 
wanking his cock between us, his hand speeding up and down the shaft. I was 
surprised how easy I slipped in and out. Then I saw him coming, and came 
myself.

We slept after that. In the night I woke up thirsty...too much wine and 
beer. As I stumbled back to the bed, I could just see Michel in the light 
from the street. Naked now, he looked very beautiful. I felt that sudden 
mix of tenderness and sexual excitement. That increase in heartbeat, and 
tension in the chest. That feeling of submission. And that erection. All 
these together I knew was love. I was in love with him! As he slept I 
leaned over, and took his cock between my lips...I had never done this 
before. I felt it stiffening inside my mouth.

He stirred and was awake. He didn't speak, but moved so my cock was in his 
mouth too. That warm wetness was new to me. We sucked. I followed every 
movement of his. When he caressed my bottom, I fondled his. When the tip of 
his finger slipped into my bottom, mine slipped into his. His tongue 
licking round my knob, mine round his. He came first, and as I swallowed, I 
came too.

In the morning it was my turn, and he fucked me from behind like Jack and 
the others, but for much longer and more cleverly finding out my sensitive 
place. And he insisted on wanking me as he fucked, whispering flattering 
endearments into my ear, or kissing my neck. After we came, I told him 
about Sophie.

The first Friday after Christmas I travelled up to town again, telling my 
parents I had a rugby practise at school and would stay overnight. (I hated 
rugby as I was too slender for the game). When I got to his flat he was 
waiting with...you've guessed! Lingerie, stockings, wig, shoes: all that I 
was used to at School, but now there were make-up, and a lovely evening 
dress. Sophie had changed from a schoolgirl into a woman. But that's 
another story for another chapter.



Chapter Six                                  

It seems amazing now that in the 'sixties, through my teen years, I faced a 
maximum sentence of life imprisonment every time I went to bed with a male. 
How could we have lived with that? But we did.  I went up to university 
four years before the repeal of the homophobic laws by the UK parliament, 
so in theory I risked Crown Court every time I committed acts of 'Gross 
Indecency' or 'Buggery'. And this threat was there all through my college 
years and beyond.

I was eighteen in 1963 and enjoying the freedom of being away from home for 
the first time. I could keep my pretty things in my own wardrobe, and my 
bedside table drawer was full of my own make-up. I could sleep in my silk 
nightie. And frankly I didn't give a toss about the law. The trick was not 
to be caught. Michel was in London, and I was looking for new friends.

This was not so easy. Gays (the word didn't yet exist) were cautious. Quite 
apart from the danger of scandal in the law courts and imprisonment, the 
College authorities usually sent down (expelled) any male students found 
fucking, sucking or wanking together. The culture of the university was 
homophobic to an extreme students just would not understand now. To be 
thought a 'poofter', 'shirt-lifter', 'mont' (after Lord Montague of 
Beaulieu), or 'queer' was to be subjected to scorn and ridicule. But most 
of those young homophobes, some of them repressed homosexuals of course, 
were innocent of any sex with girls too, for all their boasting. It was 
only gradually you found lovers, rescuing them from their emotional 
isolation.

We all rode bicycles then, and the sight of Hugo cycling with his black 
gown streaming behind him, his long legs at all angles as he pedalled a 
bike too small for him, and his dishevelled blonde hair...well, I'm only 
human and honestly he made me hard just looking at him. I almost took up 
rowing just to see him in the showers...not really. They wouldn't have had 
me, as I was too slenderly built. Anyway, one evening we got drunk together 
with some friends, and after the usual curry we all went back to his rooms 
for some more drink. 

No. Nothing happened. But in the morning, feeling dreadful (I'd slept in a 
chair and was hangovered too), I was hunting round his room for aspirins 
when I found his porno magazines. They were all gay! Innocent enough photos 
of young men posing...no sex, but the models had been chosen for the 
strength of their erections. He was, like me, in no state for anything, and 
the room was littered with bodies. I was not the only one who had not made 
it home; so I just invited him to my rooms the next evening to sample a 
special light rum my uncle had given me.

Now, my porno mags were not innocent, no, not innocent at all. 'Borrowed' 
from Michel, they included all the sucking and fucking that is now a 
commonplace on the internet, but in those days was dynamite. And I threw 
one down open on the table as Hugo walked in. 

'Jesus! You into this stuff, Simon?'

'I certainly am. You?'

He didn't answer, but stood there, hypnotised, leafing page after page of 
images that must have penetrated to his deepest fantasies. I laughed and 
slumped into the broken old settee, watching his bulge grow.

'You got many, Simon?'  

'You sit down there, and enjoy it, Hugo old man. I'll get some more.'

To be exact, two more mags, and both of them transexual. I sat beside him. 
'But this is what I really go for, Hugo.'

His eyes glazed, I swear, as he looked at those South American chicks the 
first time. 'I don't believe it. They must have used trick photography.'

'All gen, Hugo. Believe me. And here's the proof. I reached behind him to 
the chimney piece and took down the picture of my Mother. I turned it 
round. On the other side was a studio portrait of Sophie posing like a 
debutante, that Michel had had taken when I left home, and  left him. I 
must admit I looked very pretty, and very sexy with my pouting lips. This 
is still the only pic I have of Sophie as a young gal.

'Hey! Fucking hell, Simon! That's you.'

'It is...but I call myself Sophie when I'm feeling feminine. You like to 
see?' He nodded...gob-smacked would be the expression...'You'll have to 
give me ten minutes. Look you get round that while I dress.' I poured him a 
stiff rum.

Shall I indulge myself by describing what Hugo saw when I came back and sat 
beside him? It's only vanity I know, but I shall. I was one of the first in 
the 'sixties to wear my hair long, and I had brushed it till it shone, and 
tied it back with a silver headband. For the rest I was tarty-glamorous...a 
repressed boy's wet-dream! Silver high heeled slippers, a shimmering silver 
mini-skirt over fully fashioned nylons, and a tight white satin blouse...no 
pretence at tits, but just my hard nipples showing through. Under I had 
black silk french knickers and a black silk suspender-belt. Tarty red 
lipstick, nail-varnished fingers and toes, and just the lightest of powder 
as face make-up. No jewellery to get in the way, except for a few rings.

'I stood over him. 'You like, Hugo, sweetie?' I swear his jaw had actually 
dropped. I sat delicately beside him, my thigh pressed against his. 'And do 
you know what a girl wants, Hugo?' I pressed my thigh against him, and 
leaned towards him. We kissed, and he was lost.

The passion of an eighteen year old virgin who suddenly finds sex is, 
frankly, exciting. As we kissed his hands were feeling me all 
over...probably more for the silky nylon and satin than for the flesh 
beneath. But my hands were after the flesh. I was inside his flies, feeling 
his cock, his balls, and as his pants fell open, round the back to his 
hard, muscular, rower's arse. It is lovely to handle a cock for the first 
time, but doubly so when it has been the object of lust for weeks! I 
slipped between his legs till I was kneeling on the floor. His hands 
ruffled and then smoothed my hair as I sucked his knob. He was cut (most 
boys were then). Of course, he came far too quickly...but was soon looking 
for more. I persuaded him to wank me off after he had come a second time. 

He moved into the room opposite mine the next week, and within a few nights 
we were sucking each other off like experienced men, and I had taught him 
to enjoy being fucked in the arse. We were not 'faithful' to each other, 
but delighted in gradually uncovering other closet gays, and introducing 
them to what we called the 'magic circle'. I was the only crossdresser, 
though.



Chapter seven

'I'll need a few minutes to recover from that one, sweetie.'

'Me too'

'Light me a smoke, and tell me a story. Tell me about your first sex, 
Sophie'

'My first as Simon, you mean...?'

'Whatever....'

'Summer. Three years ago. No, four. Anyway, it was 'fifty seven and I was 
just twelve. I'd been wanking for a couple of years, but it was only in the 
last month or two there'd been any come. I know how you like come. 
Well there was just a bit by then. I used to imagine girls lying beside me, 
or often boys. Always boys I knew, but sometimes girls from the cinema or 
papers. And I would do it every evening and every morning, and sometimes in 
the day too. I walked about in constant danger of getting a hard on. The 
vibration of a bus seat, trousers rubbing as I walked, a bulge in a boy's 
trousers, a girl's breast. Constant state of excitement. And my pubic hair 
was still coming through, which itched a lot. Hey,you're getting hard again.
Can I have a suck?'

'Tell me about your first, first.'

'We used to 'ball' each other, us boys. That involved wrestling and trying 
to squeeze the other boy's balls. Not to hurt...just to feel, with a lot of 
struggling and giggling. Everyone did it ...so not only the boys who ended 
up gay or bi. Anyway, I had a friend called Johnny that year. He was plump, 
and like me not at all athletic. He was pretty in an 'English rose' sort of 
way, pale, clear skin, blue eyes, and blonde hair. 

'We used to go up to the golf course and walk around hunting up lost golf-
balls, to sell back to the club professional. Daft, really, given that both 
our families were wealthy...but his father like mine believed in keeping 
the children short of cash...and supposedly out of trouble.

'I remember it was hot...yes, like that. I love it when you suck 
me...Jesus! That's good...Where was I?'

'On the golf course, sweetie....'

'Oh, yes, it was hot. We sat down in a clearing in the gorse...that fine, 
soft heath-land grass, and the shade of a silver birch tree over it all.

'I bet mine's bigger than yours!'

'Well, you're certainly fatter than me, Johnny!'

Johnny pretended to take offence, and we had a 'balling' session, wrestling 
on the ground, seeking to grasp the other boy's privates ...to use the 
polite word of the 'fifties. I was suddenly aware that Johnny wasn't really 
trying to 'get' me, but was just as interested in grasping a handful of my 
buttocks. And I could feel his cock hard in my grasp. I let him get hold of 
my cock, and he would feel that stiff as well. We weren't wrestling now.

'Hey Si. I could do with a jerk-off now. You jerk off?'

'I do. Often. And I could too. Let's....'

We were sitting side-by-side now, backs to the bole of the tree. I undid my 
flies, as he did too, and as I slipped my shorts down to my ankles so did 
he. The fine grass was soft against my bottom. He was rubbing his cock up 
and down. So was I. He was longer than me!

'Let's...let's do each other...' As I spoke I reached out and felt his 
cock. So familiar that softness of exterior and springy steel within. And 
yet so strange that it should belong to another boy. He  reached for for 
mine, and we jerked each other.

'Steel within. I like that, Simon. You've got a fine turn of phrase...'

'Don't stop.I promise I won't come yet. Promise. Yes, that's good. 
Deep, and long and slow. Yes, like that.'

Johnny was that little bit older than me, and I was surprised, though 
excited, by the amount of come he spurted, and it's thick whiteness 
compared with my thin squirt. He wiped his hand on the grass, and pulled up 
his shorts. I would have liked to lick my hand, with his come on it, and to 
have kissed my thanks. But I didn't, fearing seeming 'girly', and the 
moment was lost.

'I wonder if we had kissed that first time we would have gone on to become 
more complete lovers. Anyway, we didn't, and we never progressed beyond 
mutual masturbation in the year before Johnnie's parents moved away, and I 
lost touch with him. 



Chapter eight

Neither Sophie nor Simon had sex with a girl until they were 23. I knew I 
was bisexual, because of dreams and also the effect a beautiful girl, real 
or picture, had on my young cock. But I was shy of girls, my sex-life quite 
full enough with boys and men, so I lacked the drive to break through that 
timidity.

After College, I got a job with the UN in Belgium. My immediate boss was an 
American woman a few years older than me, and a Phd. She was very pleasant, 
and really very lovely. Tall, long dark hair, slim hips, nice breasts if 
they were real, and a cool but pleasant manner.  I joined the department 
when there was a bit of a crisis on, and we got together quickly with the 
pressure of hard work.

Anyway, the crisis passed, and 'as a way of saying thanks for your hard 
work', she invited me to dinner...at her flat. I was reminded of my 
seduction by Michel; I knew she would make a pass, or expect me to, but as 
usual was content to be passive, to let things develop as they would. The 
dinner was successful...her steak was excellent, and I was pleased with 
myself for cooking a skilful and difficult souffle with Grand Marnier. We 
got well into the second bottle of wine, before we sat on the sofa with 
brandies. She lit a joint...this was 1968 after all...and we both used it 
before she stubbed it out. We were silent, listening to Hendrix on her 
record player.

She was direct. She took my arm and draped it over her bare shoulder, and 
my other hand, placing it on her breast. It was real, all right! Plump and 
firm...and a completely new experience for me. We kissed, and it was subtly 
different from all the men I'd embraced. Her hand rested on my crotch and I 
felt no embarrassment that she would feel it swelling, hard.

'That was the first time I've ever kissed a girl, Belle.'

'Really, Simon. You've never kissed anyone?'

'That's not quite what I said....'

She thought a moment. Oh! I see. Girl. But you've....'

'Often. Lots of boys....' I pulled her close and we kissed again. My hand 
down and inside her dress now, feeling the lacy lingerie (the Sophie in me 
loved that!) and the warm soft flesh, the hard nipple, larger than the men 
I'd teased. 'But I know what I've missed now.'

'I can see that!' She laughed and gripped my cock through the thin cotton 
of my trousers. 'And I go both ways too. I used to live with a girl in New 
York before transferring here.

I told her about Sophie.

'Now that's nice. Perhaps that what I've always wanted. A girl with a real' 
she squeezed my cock,'a girl with a real cock. You're nearly my 
size...let's play Sophie and Belle.'

Thirty three years on I can still remember the satin french knickers and 
matching green camisole top she lent me, the pale green suspender belt and 
the glossy, fully-fashioned nylons. Her shoes were a size too small for me, 
but I crushed my feet into her high heels. I borrowed her lipstick...my 
hair was shoulder length in those days, and cut by a ladies' hairdresser.

She was naked...me dressed...as we made love that night. We had each other 
orally, and conventionally. I was a tigress. The years of repressing my 
heterosexual urges broke out in a magnificent potency, the likes of which I 
have never experienced again.

We fucked, drank, fucked, smoked, fucked again all night. And then slept 
till mid-day.

We might have married, but she was transferred back to New York soon after. 
Over the years we have met from time to time as our paths crossed, and when 
we do it is always Sophie and Belle.



Chapter nine

In the days before the internet it was not so easy to find sexual partners, 
especially if you were looking for other than a simple hetero (ie wife of a 
neighbour) or gay (ie picked up in gay pub) affaire.  Simon had indulged in 
both, but perhaps more the second than the first. Anything different...in 
the crossdressing line.... would have been problematic. But there was a 
magazine called Rendezvous, which he first found in a hotel room, stuck 
inside the bedside Gideon Bible.

Simon had been married about five years, and it was 1975. He had never told 
his bride about Sophie. In fact he had bumped Sophie off a few weeks before 
the wedding by simply packing all her lovely clothes, wigs, shoes and make-
up in a couple of suitcases and shoving the lot in a skip at the local 
council dump. In passing, what a waste...especially one particular pair of 
silver high-heeled shoes and a spectacularly sexy black and red satin 
basque. Hey ho!

Anyway, leafing through the mag, which was devoted to all sorts of contact 
ads, he came to a tranny section, at the end. And in among the trannies, a 
few couples looking for transvestite partners. One couple in particular 
caught his eye...partly because they were in Manchester, where his work 
often took him, and partly because the woman was the sort he liked 
nowadays. Blonde, bubbly smile, petite, and from the look of her bra, small 
firm tits. There was no pic of her husband. There never was in those 
couple-ads. He answered, and enclosed a pic of himself in a tiny pouch, on 
a beach in Italy, telling them he looked much prettier as 'Sophie'.

My weekly visits to Rochdale always took the same course. Simon would go up 
to their bathroom, wash, shave, and dress, and Sophie would descend to 
their front room. We would drink some of the champagne I always brought, 
and then we would play. Sophie was always very careful to be exactly 
bisexual...not favouring either Muriel or Daniel with more caresses than 
the other. Daniel loved to be sucked, and we would tease him by making him 
guess whether his wife or Sophie had her mouth round his thin, springy 
cock. She loved to be sucked by Daniel while Sophie fucked her from 
underneath with long, slow strokes. After I'd come in his wife's cunt, I 
had to get out from under quickly for him to have her. She was the first 
multi-orgasmic woman I met (and the last too!).

I always reverted to Simon for the night, and would sleep naked between 
them on the double bed. I would fuck Muriel again while her husband fondled 
both of us...usually Daniel couldn't fuck a second time.

Muriel worked in a dairy, and had to get up early. I would get up with her, 
leaving her husband in bed, and we would drink tea, me naked, watching her 
dressing. Usually I'd have another quick fuck, but short of coming. Then 
I'd put on just stockings, suspenders and panties, and take his tea up to 
Daniel. Before he got up for work we would suck each other, and then he 
would come over my panties while I knelt, wanking myself furiously as he 
rubbed his cock in my satin-clad crotch. 

We both knew Muriel had other lovers, but she kept them to herself. Daniel 
had a really lovely boyfriend...not more than seventeen, and with a skin so 
black it was nearly blue. I'd met him once, but Daniel was jealous, and 
wouldn't do a threesome. Finally I got bored with the couple, and by now 
Sophie was well and truly alive again, and enjoying herself promiscuously 
with men, women, and other tvs. So I quietly dropped them. I noticed them 
advertising again a few weeks later.



Any reader who has got this far will recognise that little Sophie is a 
persona of the writer, who has several in fact. And that this piece is 
very-nearly autobiographical, only a few names and places being changed to 
protect friends and contacts who are not 'out'.