I am five years older than my brother. Our parents divorced when I was twelve and my brother was seven. Unusually, I went with our mother, he with our father. It made sense in that I took after my mother whereas he was unmistakably our father's son.
I, Jeremy, am now twenty-four years old. I am five feet ten inches tall and slim. I weigh about 140 pounds (a bit more when I indulge my liking for chocolate). My face has a feminine cast and I have large brown eyes, delicately shaped eye-brows and brown hair, which falls naturally in waves, as my mother's did. I realised years ago that I am attracted to female clothing and men in more or less equal measure. I often dress at home but I have never gone out in public and I have never had a boyfriend; I am virgin. In other words, I am a closeted, gay, screwed-up transvestite. I earn my living in advertising, on the creative side, and work mainly from home, so I am able to spend many of my days as a woman, which is when I am at my happiest, though, more and more, I long for a sexual relationship with a virile man.
I enjoy the whole business of making myself into the woman I know myself to be. I love shaving every bit of my body, particularly my bush, cock and balls to make a really smooth clity and then securing my male bits between my legs with a tight pair of panties. I love the feeling as I draw my stockings up my smooth legs and fasten the lacy tops to my suspender belt. I put on my bra, being careful to push up my breasts and, sometimes, I enhance my cleavage with a touch of makeup. Making up my face follows. I tend to keep my makeup light; my facial hair is blond and fine so I have no real shadow to cover, so, except on the rare days when I decide on an elaborate toilette, it is mainly a matter of applying a brushing of powder over a minimal base, eye-shadow, perhaps mascara, and lipstick . I arrange my hair. I select a pair of shoes, sometimes with heels, sometimes not, and then I am ready for my day as a working girl. At night I either sleep naked or I wear a short see-through nighty, which will ride up easily. I have a selection of dildos.
My brother, Karl, is a rugby playing hunk like our father. He is six feet two inches tall and weighs nearly 200 pounds. Our father died over a year ago and our mother died whilst I was in college. Each of them left their money for us to receive, divided equally between us, when we reached twenty-one. I was already of age when our mother died and, with her bequest, I bought an apartment with views over the river and park.
Our parents had insisted that, as we were growing up, we spend at least a month in each other's company with one or other of them each year, so we were not strangers, but we had nothing in common except our parentage. I felt some slight affection for my younger brother and I imagined that his feelings about me were equally lukewarm..
Karl has gained an engineering apprenticeship in the city where I live, so, it seemed to me, I had to offer him accommodation until he settled and sorted out something for himself. It would mean that my feminine life would have to go on hold in the evenings, but I should still be able to dress during the day when he would be out at work. Depressing but unavoidable in the circumstances. I hoped it wouldn't be for long.
I hadn't seen Karl since our father's funeral and then we had both been too involved with fending off the sickly reminiscences and condolences of our legion of relations to take much notice of each other.
We had arranged that he would arrive early one evening in time for dinner. I was a good, though not spectacular, cook, and I thought it best if we could get to know each other in private to begin with. When I opened the front door of my apartment to him I almost fell on my knees and worshipped. He was gorgeous. Even in a jacket and trousers which had seen much better days I could tell that my brother had become the most beautiful, sexy man I had ever clapped eyes on.
To work from the top: he had our father's waving golden hair, his strongly marked, arched eye-brows and his piercing blue eyes. Karl's nose was classically aquiline and his lips were strong, firm and masculine. His face was that of a god in a book of Norse myths. His shoulders could have held up the world; his chest was broad, with magnificently defined pecs and a six pack his tatty checked shirt did nothing to disguise; a mat of golden chest hair peeked out from his open collar; his hips were narrow but shapely. When he deposited his luggage and turned around to take in the view of the living room, I saw that his buttocks were tight and I immediately imagined dimpled muscles swelling into his magnificent thighs and calves. I fell in love at once. But that raised a problem, or rather several problems, as you can, no doubt, imagine. The first being that I needed to disguise a raging hard-on.
'Where do you want me?' he asked.
'What?'
'Where shall I put my stuff? Where am I sleeping?'
'Oh, sorry. I was in the middle of seeing to a client on-line. Let's start again. Hello, Karl.'
'Hello, Jeremy.'
'Bring your luggage in here,' I said, opening the door to what would be his bedroom for the short time he was staying. I had made up the bed and laid out towels for him.
As he started hanging up his suits and jackets and folding his clothes into his chest of drawers he looked over his shoulder at me and said, 'I really appreciate this, Jer.. I hope we can get to know each other better. I'll try not to do anything to get in the way of the life you've made for yourself. Just tell me if you want me to make myself scarce any time.'
'What a sweet guy,' I thought. 'There's nothing to disturb in the way he means but he's already blown my existing life out of the water.'
''Dinner's in the oven,' I said. 'I hope you like lasagne.'
'Favourite,' he said and I thought 'He's still only a boy, despite his looks and his nineteen years on this earth. I shall have to be very careful. He is my brother and I don't want to frighten him or make him uncomfortable around me.'
I smiled and said, 'Make yourself at home and the food will be on the table.'
I went back into the living room and had to lean up against the sideboard. I felt faint with the vision of this stunning brother of mine. Then I went into the kitchen and served out our meal.
That night, after he had gone to bed, I lay on my bed, imagining my little brother was fucking the living daylights out of me. I came like a fountain from using my hands, as I should like him to use his, in working my cock and balls, before I pushed my favourite dildo into my pussy, making believe it was his cock entering me and filling me with his baby batter and making me his girl. At which point I came again.
*****
We soon got into a regular pattern. It was based on the pattern I had developed for myself. I made breakfast and settled down to my work whilst Karl went off to his work. After Karl had gone out I would dress and live my day as a woman, then prepare our evening meal and change into my male clothing before Karl got home. I liked to be in my female clothes for the food preparation because I could pretend I was a wife waiting for her husband. Karl always made a late- night drink and snack for us.
I had expected that a boy of Karl's age would want to be out every night but he seemed quite content staying in, reading and watching television with me. For two or three weeks he became obsessed with 1950s situation comedies, where the husband always called out, 'Honey, I'm home,' when he got in from work. Karl took to doing the same thing which allowed me to respond, 'I'm in here, darling,' as the wife always did. Karl had no idea how turned on I was by this little exchange.
He found an amateur rugby team which played on Saturday afternoons. In the morning he helped me with shopping. We had a light lunch out and then, if there was a match, rather than just training, I went with him to watch. I should have liked to watch him training too but realised that the team would think that odd. However, I soon found that I benefited from his Saturday rugby in another way. For several years I had sent my washing to a laundry but I always washed my flimsies by hand and dried and ironed them at home. Now I added Karl's underpants and his jockstrap, which he wore under his rugby shorts, to my hand-wash items. The first time I picked his jockstrap out of the laundry basket the smell of him was more than I could resist. I pushed my nose into the fabric which had held his cock and balls and inhaled as deeply as I could. I licked at the place where I thought his piss slit had been and was rewarded with such a taste and smell of manhood I came in my panties.
As you can tell I was utterly infatuated with my little brother.
As time went by we both came to accept that he was not looking for his own place. I asked him what he would like for his approaching twentieth birthday and I was touched when he said, 'Nothing, except will you allow me to take you out for a special dinner.'
'That is a present to me, not to you.'
'I want to say thank you for the months of meals and for the way you have taken me into your home. You obviously have cut down your social life to nothing to make me comfortable.'
'Karl, most of my life has always been work. I don't have a social life in the way you mean, so I'm missing nothing, and I have the pleasure of your company.'
'But you're a good looking man. Don't you have a boy friend?'
It took me a moment to register what he had just asked.
'How do you know I'm gay?' I asked.
