Why

By Amy Redek

Published on Nov 5, 2023

Transgender

What!' She exploded, her face went rigid, her pencil still halfway up in the air. How...Why?'

Why,' I smiled. Because I found out that though he said he loved only me, I found that he was fucking another boy from the village when I wasn't there.'

You...you can't mean this?' she asked, her face white. You're making this up just to shock me.'

`No I'm not, honest. You can check the records if you wish but you'll only find that the coroner recorded his death as an accident, but I know better,' I said with a smile. She gave a little shiver but kept on.

`You said the why but how?' she asked in a low voice, her pad and pencil in her lap now forgotten.

`When I found out, I went storming up to his bedroom. He was now sleeping in a separate room from my aunt because of her illness. It was late in the evening and I'd just come from the village when I had been told by a smirking youth at how he was the lover boy of my uncle. Well I wanted the truth out of him. He'd just got undressed and was naked when I confronted him with the accusation of him having had this other boy the same way as he had me. He laughed and waggled his prick at me. This doesn't pick and choose, he goes into any hole he can find. I was really mad and charged at him and head butted him in the chest. I had collided with him with some force and he staggered back towards the open window and then he just seemed to topple over backwards out into space. I heard the thud of him landing but didn't hear any other sound, like him crying out at the fall or any kinds of moans and groans. I went and looked out and saw him sprawled on the terrace below and guessed that he'd bounced off the balustrade that surrounded it. He wasn't moving and I didn't dare go down to look but went off to what was my bedroom and spent a sleepless night wondering if I had indeed killed him.

I must have slept for I woke up to shouts from downstairs and after dressing and going down, found that my uncle had been found and was now laid out in the lounge. The doctor soon arrived and pronounced him dead, which was obvious at the time. The autopsy showed quite an amount of alcohol in his body, broken ribs and a broken neck, so a verdict of accidental death by falling from his bedroom while under the influence of alcohol was recorded. That's why he cannot now be prosecuted.'

This is a pack of lies,' Heather stormed at me as she stood up, her face very red and looking really angry. You're just trying to wind me up.'

`It's the truth Heather, so help me God, it's all true,' I said.

`We'll see! I'll see you next week!' and she stormed out of the flat. Good luck then I said to myself for it was true. The one part that I didn't tell her was that the other village boy that my uncle had corrupted, was now working with me in the same club and that he was known by the name of Sally.

Now whether my aunt had been faking her illness or not, I never knew the truth, but after my uncle's death, she appeared to recover and was now mobile again ever since the funeral. As her favourite nephew, well the only one really, I was still welcome back for my holidays and I saw to her comfort as best as I could whilst there. I also tracked down this other boy from the village and got us together by relating all that had happened to me with my uncle, omitting the scene of his death.

As promised, Heather returned the following week and gave me a trite apology for she had checked up on my story and found out about the autopsy and coroner's verdict, but added a rider to it.

`You could be tried for murder you know,' she said.

How?' I asked which was different from using the word why. What I have said to you was a private conversation that should be as sacrosanct as the confessional. Besides, it would be your word against mine with you not having a shred of evidence to support any accusation that may be made against me. So the question is do you want to continue in this, shall I say, the whys and wherefores of me wanting to stay always dressed as a woman?'

`I think I've bitten off more than I can chew, but yes, by all means, let us continue,' she replied.

`Are you a virgin?' I asked.

`What? My being a virgin or not has nothing to do with what we are discussing,' she said, a little red in the face.

Oh yes it is,' I countered, leaning forward. I'm a virgin when it comes to whether or not I've had sex with a woman, but not one in the case of knowing a man. The reason for my asking is because if you are a virgin then you'll have no concept of what I'm talking about when I say that having a man's prick up inside you, feeling it throb and pulsate, knowing that he is going to spill his seed and in your case, get you pregnant if you're not on the pill, whereas in my case, it's a biological impossibility. If you've not had the experience of having a man fuck you, then you are wasting the time of both of us. Now, I'll ask you again, are you a virgin?'

`No,' she said in a low voice, her face quite red as she looked down at her notebook.

`Have you ever had sex with another female?'

`I...er, no.'

`Do you have any sexual feelings at all at seeing me dress as you are and yet knowing that it is a man beneath the outer covering?'

`I...er, we're not here for me to answer your questions but you to answer mine,' she blurted out, her face now a flaming red and I noticed that she had to cross her legs, a sure sign that she had some kind of stirring within her. I gave her a sweet smile.

I had hoped that there might be, what with me being a virgin in this sense and that you could possibly turn me into a heterosexual and lead me out of my life of depravity as you see it.' I gave out a big sigh and watched as she crossed her legs again. For with you crossing and uncrossing your legs like that shows me that you are getting rather wet between your thighs. Body language tells me a lot as well as your facial features. You do blush a pretty colour.'

Please Jackie!' she cried out. We're not her to discuss me but you.'

`I know, but this is the very first time that I've sat down with a woman that has attracted me and you didn't really answer my question.'

`What question was that?' she asked, all flustered now.

`Was there any sexual curiosity as to what is under this dress knowing that it is a man?' I then stood up in front of her.

`I...no,' she stuttered.

`You're not telling the truth now Heather,' I said as I pushed the straps from my shoulders and let the dress drop to the floor, revealing myself in my ladies underwear and sporting a nice healthy erection.

Oh my God! No Jackie, no,' she said, her eyes fixed on my throbbing penis as it swayed from side to side as I moved over to the settee and sat down beside her. This is not professional,' she said, seeming to have difficulty in getting these words out. I put my arm round her shoulders and with the other hand, turned her face towards mine and pull it close so that I could kiss her. She tried to mumble something as our lips met and I felt her shudder and lose some of the stiffness that I felt at first in her body. Her hand moved down and grasped my cock and she held it tight as we kissed.

With our lips now glued to one another, I let my hand go down and cup her breast and gently knead it as her body began to tremble and I didn't get any resistance when I pushed my hand between the buttons of her blouse and down into her bra to feel the real thing that was covered.

`Jackie, no,' she said without conviction as we broke off our kiss for breath. She made a half hearted attempt to pull my hand out from her blouse but gave up when I kissed her again and now that arm came up to hold me as we did so. Her nipple was roused and now as hard as a little nut under the palm of my hand and her hand on my cock began to move on its own as she slowly began to rub me.

I released her breast and began to fumble and get the buttons of her blouse undone and soon was pushing it back over her shoulders. There was no resistance to this and none when I pushed the bra up for both of her breasts to fall free for me to massage and gently squeeze.

As if in slow motion, we slowly rolled and fell to the floor where she was forced to let go of my cock but this free hand came up to hold my head as we carried on with the kiss. I got my free hand to wander up her thigh up on the inside of her skirt and my fingers moved the gusset of her panties to one side and found that she really was wet and pushed two fingers inside her.

She gave a gurgle and a slight squirm but made no effort to stop my questing fingers as they began to play with her clit.

We were both panting heavily now and she broke away from the kiss to quickly use her hand to pull off her panties and hoist her skirt up as I rolled over on top of her. The wetness between her thighs was like a flight guide path for my throbbing cock to home into the waiting field for me to land.

I moved over her more and slid into my first ever woman and revelled in that warm wetness that surrounded my cock, softer and less pressure than when inside the backside of a man. Also there were many more muscles that came into play to ripple along the length of my erection as I slowly eased myself in and out of her as we fucked there on the carpet of my sitting room.

Her legs came up to my waist and over my hips as I moved ever deeper inside her. It must have looked incongruous at this female clad body on top of another woman as the arse moved back and forth in the fucking motion. My first time of being inside a woman was blissful for the pressure on my cock was less intense, but there nonetheless.

`Oh God! And this is your first time?' she gasped out as we moved together.

`Yes,' I replied, making almost the same kind of noise that she was in between our gasps for breath.

So...ooooh, don't stop. There...oooh, keep going, I'm coming,' she cried, her voice getting higher and then she convulsed under me, bucking like crazy making me bounce even harder inside her. Now!' she screamed and held me in a vice like grip between her thighs as she shuddered, her back arched and well clear of the floor, triggering me to come at the same time.

Both of us humping each other as we moved on the carpet as we came to our climax, her screaming and me crying out until we came to a shuddering halt and her hands came up and held my head tight as she fiercely kissed me.

Still on top of her though supporting some of my weight on my elbows, I stayed inside her as she flexed her muscles around my cock while I could only make mine twitch but it was enough for both of us know that it was still there.

`For a first time Jackie, that was one hell of a fuck,' she said and I don't know why but her use of the word fuck, was the first time I'd heard her say it, and it surprised me though she'd already heard me use it quite often.

`For which I thank you very much, you being the first woman I've ever had the pleasure of being service to.'

`You can service me any time if it would be as good as this first time,' she said, her eyes alight and really glowing with pleasure.

`Well let's see how we can prolong these interviews we're supposed to be having,' I said, giving a peck on the end of her nose.

`Now you're talking dirty by mentioning work,' she said as she wrinkled her nose that made me laugh and so I slipped out her along with her little cry of dismay. One that I've often made when the cock that had been hard and fast up inside my backside was pulled out and I knew just how bereft she felt. This was another little piece that she could add to her slowly growing manuscript on the love life of a transvestite.

I rolled off of her and we had parted with the squelching sound of two sweaty bodies parting, a sound once heard and experienced is never forgotten. Her skirt was bunched up at her waist and her bra up around her throat, her legs wide open, her sex clearly visible and she was looking the veritable picture of a woman who had just been well and truly fucked.

I got up off the floor and helped her up and led her through to the bedroom where at least, I had a bathroom that led off of it. She was undoing the clip of her skirt as she went and that fell to the floor as did her bra just before she disappeared from view, her bare backside looking very nice indeed that made me wonder if I could ever get to put my prick up in between those cheeks and fuck her that way as I would another man.

While she showered for a few minutes I took off my underwear and as she came out of the bathroom, gave my shrunken prick a stroke as I went in for my shower. I was only in there a few minutes and when I re-entered the bedroom, found her still naked but now lying out on my bed. The only items that were incongruous in this attitude of hers was the fact that she had her pad and pencil with her.

`I thought that we were going to take it easy over the real reason for you being here,' I said on seeing these items.

`Let's get the story of your life out of the way first,' she said with a lovely smile that was much better that the previous ones I'd seen. Oh shit, I said to myself for I'd seen that look before, not on a woman I must say, but on a man and it was one of love.

Why? Why did this have to happen with the very first woman I had sex with give me this loving look? I was a confirmed homosexual and only loved having a male penis, up, erect and rampant, throbbing and having the expectancy of having it shoved up my arse. Now having fucked this woman was I going to have her as a mill stone round my neck? She patted the bed beside her and I all meek and mild, did as I was bid and got onto the bed and lay down beside her. I had wanted to put on my underwear but she had stopped me from putting on my armour as what it seemed to me and now I was there naked on the bed with her and I felt so vulnerable at being in that condition.

`Now where were we before we got distracted?' she asked.

`Whether you were a virgin or not,' I said with a smile.

Well that's been answered,' she said as she pushed my hand away from trying to get in between her thighs. Later.'

`Let's say that you were thinking of having me indicted for murder for a start,' I replied, now moving my hand up to a breast.

`Right, let's go on from there,' she said all business like now though it seemed strange to be continuing this with her lying naked there next to me and when the inevitable happened, there was nothing I could do about it for in my reminiscing, thoughts and scenes came to my mind and it wasn't long before I had a throbbing erection lying up on my stomach. But before this happened, I took up the story at near enough where I'd left off earlier. I did renege a little on what I really didn't want to say.

`Well as I said before, my uncle had been having sex with another young boy from the village. He too was into dressing up as a girl and having my uncle fuck him which led to our confrontation.

It was after the funeral, I got this boy whose name I'm not going to divulge, to come up to the house and introduced him to my aunt saying that this was a boy who I'd made friends with and would like, with her permission, to have him stay over some nights and be a companion for me. My aunt, sweet thing that she was, thought it good that I had made a friend of one of the villagers and so let him sleep over at least four nights a week.

After having talked over at how we both had been, as you would call it, turned into queers, we decided to carry on playing the games that my uncle had instigated. After breakfast, we would go down to the summer house and both dress up as women and then play at being lesbians. Sucking on each other's cocks as well as sticking our fingers up each other's arse, but took it further because not being real women, we still had cocks that could be used apart from being taken into the mouth.

It wasn't long, a couple of days, before we would be fucking each other and having a great time in the process. I don't think you would ever come up with a sexual position that we didn't try. I think I might have said already that it wasn't the size of the cock that was used to fuck you but how it was used. To probe, scratch, tickle, soothe or rasp, as long as it could be felt when it was moving up in your backside and whether it gave you an erection at the time was the criteria of how that cock being used determined at how successful the use of it was in arousing you to this state.

We both of us said that it would have been just perfect and the icing on the cake if there had been another two persons like us to join in. That meant that if it was I that was being fucked, I could also have had an erect penis for me to suck on while another mouth was sucking on me at the same time. Now that was our idea of pure heaven.

We would both be dressed in female underwear as we had sex together and I really loved that holiday with having him take me with both of us dressed in the same way. I found out that he had a good singing voice and as a surprise to me, found that I had a good voice too. We then got a record player down into the summerhouse and would, dressed as women, sing duets together. That was in between our usual congress together.

I, by now, hated wearing the constrictive attire of men, i.e. trousers and ties and much preferred the loose flowing garments of a female.

To please my aunt, who was quite good at the ivory keys, we would be in our normal boy's attire and sing while she played and really encouraged us in our singing and even got round to teaching us how to breath properly when doing so. She did more for me in this field than my own parents ever did. They never really had time for me in all aspects of my childhood. I was there and that was it and I think they were glad to get rid of me every summer.

I loved those next two years of being able to discard trousers and the like to wear flimsy costumes and act and be a female in all senses of the word. To be caressed and fucked as one. I was in my element which I have since carried on to this present day.

Sodomy is the word used and that is the name given to the act of a male fucking another person up the arse and the person being fucked and liking it be it another male or a boy is called a sodomite. The one who receives the male cock instead of giving it was called a catamite. These words only came about from the Bible, but people like us were there long before Christ and before women became prostitutes, for a male whore was more valued than a woman over a thousand years before Christ.

A catamite was a very much favoured person in any court and none more so than in Egypt. They were held in high esteem by the people who were fucking them and they rose to quite some powerful positions in their time. It had been learned that animals only copulated for procreation whereas humans joined together for pleasure too. The difference being that by a man going and fucking a catamite, didn't finish up with any unwanted offspring and possible threats to his reign as head of whatever position he held at the time.'

You might lie there and espouse this,' Heather interjected, but what you are talking about and saying that you do, is still against the law.' I snorted at this.

`The law? This only came about in the last two hundred years where people like me were doing this thousands of years ago and will continue to do so till the world ends. there are many people who are, what we call closet queens, hiding their sexuality in the closet. It is rife and cannot be controlled by any laws. We are talking about human nature and as soon as anything is banned by law, the problem it has tried to quell expands and grows all out of proportion.'

Be that as it may,' Heather said, It's still against the law.'

`God help us if they ban this,' I said as I rolled over onto my side and let her feel my erection pressing up tight to her thigh and caressed her breast. Her nipple rose up instantly into that tight little bud.

`God forbid,' she said as she pulled me over on top of her, her legs opening for me to get in between. She was wet and waiting and I slid in easily and fucked her to the pleasure of both of us.

Though it had been nice having Heather, she would never replace a tight arsehole and neither could she give me what I really wanted, a big cock up mine. That was to be found at the club and it was nice to be up on the small stage singing and knowing that many of the men out there in the dark wanted me. They would give me what I craved and even paid me for it, coming off the stage after my third song and being given a drink. The regulars knew that it was a large gin and tonic for me instead of the muck they served up under the name of champagne. My leg would be stroked and I knew that he wanted me and so the drink went down in one and I would lead him to the cottages. Not until we were inside would I hold out my hand for the money and depending at how much he gave me determined whether it was oral or anal. Some of the men were fastidious enough to want a condom and this I would produce and expertly roll it down the erection that had been pulled out of the trousers. They varied from thick to thin, long to short but most were of the average size of about six and half inches.

I would bend over the basin in there and feel the hem of my dress lifted up to my waist as a hand held it up on my hip as his other hand guided him to where he wanted to go. It was lovely to feel the head of the cock nuzzle my entrance and then have it pushed in, widen me to fit him as he would slide into me as his other hand now held my other hip. Then it was chocks away and I would be flying as the man behind me started to move and drive his cock in as far as he could as he fucked me. His thighs, covered by his trousers, would press to the cheeks of my arse on his forward ramming and sometimes nearly pull out in his motions. Not many men lasted more than a minute of moving his cock in and out of me till he gripped my hips tighter as he pulled me close to him and began to jerk out his sperm into the rubber or me. It was glorious and I could never get enough of this pleasure.

Very seldom were we alone out there for there was nearly always one or more of the other girls being serviced in this way or down on their knees giving their trick a blow job. How we finished half of our shows I don't know for we were nearly always half pissed by the time the finale came having had quite a few drinks tossed down our throats.

The week flew by and I soon had Heather knock at the door to my flat. She gave me a smile and a peck on the cheek as she entered and now being familiar with the place, went straight over to where the drinks were and poured us both out a drink.

`Shall we take these into the bedroom with us?' she asked and without waiting for an answer, went ahead of me and after taking a sip of her drink, put the glass down on the bedside table.

`Get that dress off then,' she said as she slipped the straps off her shoulders and let hers fall to the floor. It was off quicker than mine and I saw that she was wearing just the same as me, a bra, suspender belt and stockings and no panties.

There were two differences between us as we faced each other, both quite beautiful to look but she was able to fill her bra and be seen to do so which I couldn't and I had a straining erection jutting out from my thighs where her flat tummy ran straight down to her small bush without any protuberances.

`It's a lovely shape,' she said as her fingers ran down the top of my shaft and she went down onto her knees as her hand grasped the base of my cock and put her mouth over the head. The inside of her mouth was hot and her tongue flicked over and round the head as she gave me some sucks while working her hand up and down on me.

`Not too much,' I groaned, loving to see her brunette hair weave about as she bobbed up and down on me.

No,' she said, letting go of me and standing up and moving back towards the bed. I want it to come inside me, but first, give me a lick and a suck.' She now laid back on the bed and opened her legs for me to see what she wanted me to attend to with my mouth and tongue.

Now I'd already had my cock stuck in there between those lips but never really looked at a real live one before. I'd seen pictures but not close up as I now was and I must say that it's not the best view in the world. There was nothing to really get hold of with either hand or mouth, not like a rampant cock. That you could feel properly and it was something that you could use your teeth on. With a woman it was mostly the tongue to be used and to me, it'll never take the place of giving head to another man. I didn't stay down there long and I soon moved up and pushed myself into what I'd just been tickling and got more pleasure this way though I would still rather it had been a man. But a hole is a hole and a fuck is a fuck so I did the best I could with what I had.

It must have made a good picture viewed from the side to see two female clad people together, one on top of the other and it would have been hard to tell which was which as I was squashing her breasts with my chest. Though it was her that cried out in the throes of an orgasm while I just grunted away as I came inside her.

The difference was also apparent when I pulled out and moved back onto my heels, my wet cock still pulsating as it stuck out from my thighs. As exhausted as she looked, Heather still turned round on the bed and took my cock into her mouth and sucked on me for several minutes as I stroked her hair not knowing that this was the last time I was going to see my psychiatrist. There was no hint of this as we got dressed again and she gave me a kiss before leaving.

It wasn't until the following week when I expected her and had Miss Winters standing at the door instead.

`No Heather with you?' I asked as I invited her in.

`No. She's finished her evaluation of you though before you ask, I haven't seen it yet. Now how are we coping back out in the real world?' For Christ's sake, you would have thought I'd been banged up for years with asking that question, but I told her that every-thing was going fine. Well it was at the time. I was getting banged regularly every night in the club and putting my money away for a rainy day. I didn't expect it to be a storm a week later.

Next: Chapter 4


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