ABCD

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A female's first four sexual encounters with trans-women.
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NormaJane
NormaJane
217 Followers

Obviously trans-women vary, like cis-woman, in psychology as much as in appearance, and my first four encounters with trans-women illustrate this. I have given them these names, because they are appropriate to their behaviour. I met them some years ago, through a free online dating site, which covered the English region I was living in. You posted a note about yourself, a photo, if you wished, and a description of what you hoped for from a date. The site closed down after a while, probably on account of the misunderstandings which occurred.

Having invited Alpha to my flat, I prepared a light supper, showered and dressed in bra, panties, easily removable light summer dress and sandals. I was hoping for some conversation over the meal in the kitchen and coffee in the sitting-room, getting to know a little about each other. This would help to find out if we both wanted to proceed.

The woman who rang the door-bell was taller, slimmer and younger than me. She was wearing a tight tee-shirt over bra-less shallow breasts with prominent nipples, and a short skirt. She had wide-set, slightly protuberant blue eyes, a short, broad nose and fleshy, naturally shiny, red lips. She confirmed my name, announced her own, and, before I could bid her enter, she took me by the shoulders, pushed me backwards into the hallway and swung the door shut behind her with a swing of her hips. She threw her arms round me, hugging me so tight I could hardly breath, and clamped her lips over mine. She jabbed her tongue between my teeth and forced my head backwards with the force of this buccal assault. She was panting through her nose and meanwhile her hands had gone to, and were gripping, my buttocks.

As she loosened her hold enough to lift the back of my dress and grab my bottom again, over my panties, I tore my mouth away to ask, 'Would you like some supper before we go any further?' What I meant was, 'Before you go any further,' since I wasn't 'going' at all.

'Maybe later,' she said. 'You've no idea how much I need this.' The 'this' was clearly not me, but my body, which was confirmed as she plunged her hands down the back of my panties and kneaded my cheeks with bruising vigour. She thrust her pelvis at me rhythmically, so that I could readily detect her hard cock

This was my home and I was supposedly the hostess, so I could, with considerable effort, have pushed her away and either ordered her out of the house or asked her to proceed rather more circumspectly. Had this been a man I would probably have done that, regarding this approach as tantamount to rape. But this was my first encounter with a trans-woman, and I was keen to see what might happen. I was even wryly amused, a little detached from, and observant, of the proceedings. I also felt a commitment to easing the frustration of another woman. If she needed an orgasm, as she clearly did, and I could enable it, well, maybe.

She withdrew her hands, stepped away a little and suddenly picked me up, arms under my shoulders and knees. 'Can we go to your bedroom?' she said,' though it was more a command than a question.

'Urgent, is it?' I said.

The ironical tone was lost on her. 'Going crazy,' she said.

I directed her, aware of her strength. She might be slim but it was all bone and muscle.

She put me down on the bed, so that I was lying across it on my back, my feet on the floor. She stood back and ripped off her tree-shirt, revealing breasts like targets, nipples like bullseyes on shallow mounds. She unzipped and stepped out of the skirt.

Raising my head, I nearly laughed to see her erect penis sticking forth incongruously from the lower edge of little lacy panties. There was a moment of difficulty as she eased them over the distended cock, which, I could see already showed a drop of liquid at its opening.

She looked at her organ, as if reassured to note its presence and rigidity, and briefly squeezed it with her right hand. 'Ready,' she said. For a moment, I thought she was asking me if I was ready, but she quickly corrected this by casting my skirt over my chest and face, remarking, 'Let's see how things are.' Which was the signal to reach either side of my hips and drag down my clean white cotton panties. She lifted my feet to draw them off and tossed them onto the bed.

Still watching events as if from a short distance I wondered whether she would actually involve me in whatever action she intended. I suspected she wouldn't, and I was right, because she took me below the knees and drew my legs up and opened them so that my thighs were resting on my stomach. Giving her a gynaecologist's view.

'Look at that,' she said. 'Just look at that. Perfect!' But she didn't spend long looking, because she rubbed two fingers across my vulva and lifted them to her face. 'Sweet, but a bit dry.' She sucked them, gathered saliva on them and rubbed it onto my entrance. What did she expect, since so far, the foreplay had not been exactly involving?

Keeping those fingers where they were, still rubbing, she gathered spit on the fingers of the other hand and wiped it on the distended, glistening head of her penis and moved forward, still holding it, to aim it at my opening, and with the fingers in my vulva she prized me open. Then she slid the other hand along her penis and back, as if cocking a gun, or gunning a cock, and introduced the tip into my vestibule.

I wasn't exactly dripping with lubricant other than her saliva, so it was not easy for her to penetrate me. It occurred to me, laid out in this undignified position, skirt half over my face, feet, still slippered, waving in the air above me, to suggest that if we backed off a little and adopted a more co-operative approach she might find entry easier. But she was going in there regardless, for, grunting with the effort and with the pleasure of my vagina creeping along her cock, she was forcing her way home.

'Oh boy, oh boy, oh boy,' she commented, thrusting and withdrawing a little before thrusting again. 'That is so good. So good.'

Of course, as vaginas are primed by nature to do, mine began to secrete, in self-defence if nothing else, and as her passage into my passage suddenly became easier she let out a 'Woof!' of success. 'That's better. Much better. Now I'm in. Oh, it's so, so damn good in there.'

She paused, as if gathering her forces for the next phase, breathing hard, still holding her penis at the base, as if checking it really was inside. She had only to ask and I could tell her that, yes, it really was. However, asking was not on the agenda.

'Right!' she said, in the tone of a workman about to operate a tool. Well, she was about to operate a tool sure enough. 'Here goes,' and she pulled out till only the head was in me and then plunged back in with a throaty sound like a chesty cough. 'Couple more of those and I'm there,' she informed me, starting to pant harder and beginning to shake.

'Here it comes! Here it comes!' she shouted, completing the second thrust and pushing in her last fraction of an inch. 'Yes! Yes! Cummiiiiing!'

I felt the pulsing of her penis, mostly round my entrance, and the impact of her thick cum, for thick it was, oozing out of me with the consistency of custard.

She held her position, and even clasped my thighs, as if to prevent me moving till she had emptied her last ounce into me and had relished the last buzz of pleasure. 'That's better,' she announced. 'Did I need that!'

When she was ready she abruptly pulled out. Her subsiding cock slid down my crack, till she took it in hand again, and wiped it carefully on my panties. Leaving me to lower my legs, sit up and then stand, she put on the lacy panties, tucking her penis away between her thighs, resumed the tee-shirt and skirt and looked expectantly into my face. 'Bite to eat?' she asked. 'Then maybe we could go again.'

I didn't think there had been much 'we' about it. Just before her orgasm I had begun to feel a little tingling in the pussy and clit, but were trans-woman all as ruthlessly selfish as some men? 'No, I don't think so,' I said, leading the way to the front door and opening it.

'All right,' she said, 'Well, thanks, anyway,' and she strode away.

I put my panties in the laundry basket, put on one of the old pairs I used when periodic, and enjoyed a solitary supper. Then I got onto the website and amended my entry which said, 'I like to give satisfaction.'

Bravo was different. The woman at my door was about my height but bigger in bust and bum, and older than me, with expensively coiffed greying hair, and crow's feet. She was smartly dressed in a maroon-coloured suit, a grey, ruffled blouse, hose and grey high heels.

She gave her name and we shook hands formally. I invited her in and we went straight to table in the kitchen. There, over a leisurely meal, we gave accounts of ourselves. After that we adjourned to the sitting-room for coffee and further conversation, before she went to the bathroom to refresh her make-up.

She was in her fifties, a successful former businesswoman, who had, having sold her business, only recently finished her metamorphosis to trans-womanhood, realising a long-held aspiration, patiently awaiting the necessary time and money. The crucial sentence in her softly spoken confession was, 'I read your post on the site with interest, and hope, you being an older woman than most of the others. Because, you see, I'm a virgin. I did have opportunities for relationships with women, but that was before. I didn't want to make love with a woman until I could do so as I am now, woman to woman, so to speak. Can you understand that?'

'You know I can,' I said. 'You wouldn't be talking like this otherwise. I think you're brave to be here and be open.'

'Then, would you be...?'

'Of course. You know I would. I think we could manage fine.'

'And would you teach me what a woman needs, too?' she asked.

'That would, of course, be part of it. We have only to be honest with each other.'

'I'm so relieved. I thought it might be difficult to...'

'To describe your situation and ask for help. I know. But remember that if we have affection and regard for each other it won't be helper and helped but two people finding their way to mutual understanding and enjoyment.'

She smiled with her perfectly coloured lips, matching her suit. Her perfectly shaped dark eyebrows rose a little over dark brown eyes. They were wise eyes, I thought. Although short on sexual experience she had gained insight in other fields.

We stood, I took her hand and conducted her to the bedroom and we folded back the bedclothes together. I said, 'Now I'm going to take off that snazzy suit.' As well as the blouse, she was wearing a silk slip. I removed both, so she stood in her bra and panties.

She said, 'I'd like to undress you, too. I've never seen a real naked woman.' Gently she unbuttoned and removed my poly-cotton shirt and floral-patterned skirt. I was not wearing a slip, so she studied my flowered cotton panties. After which I unhooked and drew off her bra. Her breasts were heavy and sagged when released, the nipples and aureoles rather purplish in hue, and erecting in the air.

'They're rather droopy, I'm afraid. They just grew like that.'

They're lovely,' I told her, and bent to kiss them.

She shuddered. 'I never guessed they'd be that sensitive. Can I see yours?'

I turned for her to unlatch my bra and turned back, my nipples, too, erecting, and she said, 'I've seen a million photos and paintings and videos of breasts, but none of them can match up to those real-life ones. And I want to hold and caress them so much.'

'You shall, Cinders,' I said. 'But for now, let's take off those smart shoes and sheer hose. Ah, I see you wear your panties over your hose.'

'I don't normally wear anything but pantyhose, but thought it was right the first time...'

'How polite,' I said, 'And such lovely silk French ones, too.'

I kicked off my slippers and stood ready for her to take down my panties. She did so, slowly and reverently, watching my face from her kneeling position, as if asking permission to contemplate my pussy-fur and vulva. She understood that that was not just fine by me but part of the giving one woman can render to another. Here is my womanhood. Rejoice in it.

It was my turn to slide her pantyhose down and off, kneeling and looking up to let her know I was going to gaze at and rejoice in her womancock. And there it was, quite small, only a little stiffened. I took it in my mouth and ran my tongue over it.

She flinched and gave a little gasp. 'I've wondered so much about that,' she, 'What it would feel like. I know it's supposed to get hard, like the videos.'

'It's not supposed to do anything except what you'd like it to do, and what you'd like me to help it to do,' I said.

'I want to see you completely,' she said.

I drew her into my arms and we kissed. Her mouth was so soft and gentle and the feeling of our breasts pressed together was exciting her as much as me. So that I felt her cock begin to stiffen against my thigh. I drew her down onto the bed and we lay down and resumed our kissing. I ran my hands own her back and stroked her bottom. It was soft, yielding, appropriate for a middle-aged woman, but at my touch she instinctively pushed her penis in my groin. When our lips parted I put my mouth to one of her nipples and began to massage it with my lips and tongue, so that she said, 'So much nicer than stroking them myself. Let me do that to yours, another first.' She sucked, gently at first and then harder as my breast swelled and the nipple hardened.

'That's magic,' she said, 'The way they do that.'

'Time for you to look now,' I said, withdrawing a little to open my legs. 'That's where you're going to go. You can lick or suck or stroke as you wish. I shall enjoy whatever you do.'

She bent close to study me, and ran a finger along my vulva-crease. 'There it is, then,' she said, 'Your vagina begins right there. And this is your clitoris. I'm going to lick it.'

I lifted my hips towards her in response. 'If you go on doing that I shall come,' I said.

'Oh, I'd love you to come,' she said. 'Can I?'

'Of course,' I said, 'Put a finger or two inside me as well and move them about.'

She put her lips to my clitoris and licked alongside it and beneath its tip, meanwhile gaining confidence in sliding her fingers about inside me. Till I felt the orgasm gathering in thighs and bottom, and said, 'I'm going to come. Feel me coming. Feel the tingling in my pussy. Feel it sweeping through me. It's coming. Now!'

She stiffened and uttered a little gasp as I peaked, and said a little later, 'A woman's orgasm. I really helped a beautiful woman to...come, that's the word, I know. It was like a coming, coming to me, coming for me.'

Her cock had actually softened while she concentrated on me, which was a good sign. We adjusted our positions, so that I could bring my mouth to that flaccid penis. Which readily swelled as I slid it in and out through my lips.

'I think it will come,' she said. 'You know, I've not masturbated, though I've been tempted. I've got it hard, but always stopped, because I want to give my first come in a woman.'

'Now you're going to,' I said, 'In my mouth or my vagina?'

'I would love to do both at once, but it would be right for my first time inside you. If I had a vagina I would take the penis in there to lose my virginity, wouldn't I? So, for me as I am I want to go in there and come.'

'It will be sweet to take you into me and hold you and receive your cum,' I said. 'Move between my legs. Yes, that's right. I bend my knees away, like this, and you bring your cock towards my pussy. Good. Closer and closer till I can guide you in.'

'I think my cock is only small,' she said.

'Its size doesn't matter at all,' I said. 'It will come inside me, and be a new experience for me, too. I've never been given a virginity like this. I'm going to guide you and hold your breasts and you're going to move as you feel. Closer now. That's right. You're going in.'

'It's so warm and wet! Oh, you're taking me into you, aren't you?'

'Yes. Give your cum into me.' I took her breasts in my hands and squeezed gently, thumbing the nipples. 'You're going to come. Here you come!'

'Yes. This must be it. It's so wonderful!'

The fact that her cock was quite small actually made it easier to feel its jerkings of ejaculation. The size of penis has little to do with quantity of cum, for she fairly flooded me, spurting again and again.

Later that night she came in my mouth, a second loss of virginity, and later still we came together and slept in each other's arms, as we were to do for some months. Till a post abroad drew me away. We parted with sorrow, but also with satisfaction, and she went on to marry a woman in her sixties who had yearned for such a marriage for many years.

The girl I call Charlie (derived from her real name) was no virgin. She had had numerous lovers, including other trans-women, and men. But, sadly for her, she was so passive as to bring out the worst in people of all genders, who wanted to exploit, even humiliate, her.

I even had to take her hand and draw her into my hallway, or she would have dithered on the step indefinitely. She was tiny, barely five feet tall, and looked positively pre-pubescent. Her heart-shaped face, under a tumble of long blonde hair, was smooth and freckled. Her blue eyes were so innocent-looking that, allied to her virginal air, it was hard to credit that she was not only a trans-girl but the possessor of a sizeable penis. For, when you took off her taffeta party frock and little girl panties a considerable length hung between her delicate thighs. She had almost no breasts, so a bra was superfluous and only the two garments needed removing. And you did have to do the removing, for the only active steps she took were to present herself for disrobing and insist on being treated as if she were totally female, happening to need engulfing by an active partner.

On the first occasion, I had got the dress and panties off and was unbuckling the shoes when she said, 'You must do the fucky. You'll do the fucky, won't you?'

'All right,' I said.

'You fuck it out of me. It's lovely when it comes out.'

'Well, good,' I said.

'And lots and lots of it. You keep doing fucky till it's all out.'

'All right,' I said.

'It takes a long time, so you can do fucky for yourself, too.'

Evidently there was to be no preparation. Just insertion and in-out, in-out.

'Some ladies can't get the fucky-feeling just by doing fucky,' she said. 'That's why I chose you, because I think you can.'

'All right,' I said, quite intrigued by these instructions and by the fact that as she issued them her cock had completely erected and exhibited the banana shape younger ones often do. At which point she lay on my bed on her back. Her cock lay amongst her pale fluff and she took hold of it and held it vertical, looking expectantly at me.

Hastily stripping I straddled her, wondering if I were slippery enough, with no preliminaries, to absorb that impressive organ. But there was apparently no delay allowed for her little girl voice quietly demanded, 'Put in now.'

Obediently I lowered my bottom till her tip was poking into my vestibule. At which point there was a pause, till I pushed down and her penis went in an inch and she said, 'It'll go soon. The lady gets slippy and it pops in.' The only contribution she was going to make was to hold her cock erect.

A little up and down, and, of course, it went in slowly and the obliging vagina produced its slime. Then, it was clear, I was to keep up the see-saw until her ladyship ejaculated. Which is what I did, and she encouraged me with occasional remarks, such as, 'Lovely fucky-fucky. She's getting ready.' Or, 'She's going hard.' And since it was a good solid cock and I got into the right mood and focused my attention within, I became confident that when she came it might well tip me over.

NormaJane
NormaJane
217 Followers
12