About Her

Kevin had once heard that that sex with a penis and sex with a vagina were different experiences; that for people with penises, (penis-in-vagina) sex is something that happens outside of themselves, like taking a journey somewhere else; and that with vaginas, it's an invitation to enter inside your body. That sounded more vulnerable, in a good way, and the answer was obvious: if you had a penis, your ass was the only invitation inside you that you could give to someone else. Come inside, you're so welcome here. Enter me. To be full of another person, to feel their pleasure happening inside you, their skin warming up your whole core. I dunno, I'm theorizing here, maybe that's what happens. More so if there's cum involved?

Kevin's thoughts had turned to these things about an hour after he saw her; saw maybe 'me'. He had been reading a Shared article asking cis people not to treat SnapChat Gender filters as punchlines; that most trans people had lived most of their lives with a Gender Filter they couldn't take off and it wasn't fun. Kevin hadn't known there was a gender one now, just about giving oneself dog ears or something; and the thought Kevin had been too tired and depressed to think about in a long time returned, involving something far more elaborate than My hair looks better longer and I don't like traditional scripts of masculinity. Kevin worried that maybe this was a rejection of toxic masculinity, not a gender thing, and that it would be offensive to start talking about Identity and Gender.

But, having rushed to his office's bathroom, Kevin tentatively opened it up in a moment breath-shortening curiosity, and, after two minutes of fumbling, found the button. And was suddenly looking at his cousin Lena? But different, a little rounder in the cheeks, the lustrous hair bigger and wavier. The flirty and dancing hair made of the serious eyes a cyclops, fluttering about in front of the face flirtily. Something was happening, though it seemed incomplete, in progress, like an image still loading its details. Kevin, not having breathed now in some time, attempted a tiny smile; and liked it; and a toothy half-grin; and liked it; and a little hair toss, shoulder presentation, and comehither; and loved it. Yes, it's a problem that this is the presentation given as definitively feminine; but it worked here, worked really really well, for this one person in particular. Kevin was wearing a tie but something that had been tried-before in the mirror with combs and mousse and razors was actually manifesting instantly.

And it was terrifying, unless thought of as a Question or a Secret. But it was his. Should I? Should I say this inside my head? Let's try it. Okay. I'm going to do it. I'll see how it feels. Just for fun Kevin. Okay. It's a Question or a Secret; but it's hers. Hers.

...Hello!

And something came to her lips, paused for a moment until after the footsteps outside the washroom went by instead of in, a word she had never heard before but just came to mind and instantly made sense:

Kelsey.

This wasn't sudden, as was in retrospect obvious, this was a long time in coming, moments spent thinking about it elaborately and then shushed as the day continued, over long times, at first justified as guilty little fantasies, either sexual or sci-fi, or reading an article about a trans women who decided to keep her gender secret forever, and being shaken after reading it for two days.

And all this wasn't about sex; it wasn't, not at all, not completely, it was a whole identity, about who she belonged to, about who she was, about how she presented and felt good and felt herself, but the erotic landscape was there, a part of this moment. Because as soon as she whispered words like She and Kelsey, there was an enormous and hopeful erection, glistening with the precum of long moments spent in elaborate sensual thought. She looked down at herself in the phone image. And considered what to do next, in the stall, at home, in her life, but her thoughts were interrupted - the lights went out. She had been there so long the motion detector no longer registered the room as occupied. Kelsey waved her arms frantically, but due to a ridiculous design flaw she had just discovered, the sensors in the room wouldn't detect her until she was outside the stall. The washroom wasn't designed for people that took more than a couple of minutes.

Even as a Secret Question, there were a few initial scripts for what came next in this enquiry. One junk swap and one trip to the grocery store later, there was an experiment involving a soft and shiny slightly revealing blouse, and after the first glance in the mirror she felt a need to use only the filter, for now. Even though that would probably just hurt more later, turning this crutch into a Mirror of Erised if things progressed in the Real World.

Whatever this is, whatever this means.

She still had a huge desktop screen in her office, untouched for a couple of years now, and set up a screen projection in the living room. She daren't embarrass herself with anything like mascara without any context or skill, and only half-admitting anything to herself at this juncture, but one YouTube video later and she was ready to clumsily attempt some bought lipstick, a dark red, nothing shiny but not exactly subtle either.

It was at first reaffirming and lovely and flirty and a little fun, sort of like dancing alone, something she hadn't done since she was five, where it's fun and beautiful as long as you don't get self-conscious. She resented even the term self-conscious, implying that you were your own enemy and the only way to allow yourself what you want to do is to stealth it by yourself so you don't notice yourself doing it. Kelsey put away all judgemental monsters out of her mind in a fierce but gentle act of sheer will - mother, brother, boss - and let herself explore.

She watched herself. Every time she liked an experimental expression, or got better at talking with a higher tamber, honed her smile to be gentle without being timid - a kind of proud, loving but warning gleam - the same strange phenomenon occurred involving a seismic, vibrating sexual arousal. Kelsey sighed, still smiling a little, and tossing her (imaginary for now) hair a little at the computer screen.

The next day she surreptitiously bought a pair of everyday-but-reasonably-skimpy panties, put them on, and experimentally looked behind her at the mirror. Kelsey realized she was using the words Experimentally a lot these days.

She glanced this way and that, though obviously still alone at home, before she let herself flirt a little with the reflection. Her bum looked... nice! Suddenly she was noticing herself forgiving, if not (nearly) celebrating the various lumps across her body, as part of what was attractive rather than something to fix or hide. But the effect only took hold in a very certain mindset. It was so fragile, so ready to fall apart.

But for now, looking up and down, she enjoyed the way she moved. She could angle her body, animate it when she identified as a woman. It was all deeply problematic, in a way, because men can feel this way too, they should be allowed to and coaxed to, but something about seeing herself as she is (?) unleashed some things formerly indomitable struggles. And, as she began to feel interest in her own body, within the cute little panties her penis stirred and unfurled a little.

Kelsey smiled sheepishly at her reflection and sighed.

I have to do it. I have to get it out of my system. I have to give Kelsey her first orgasm. As she returned to the electronic mirror, the one that showed her the face she felt right in, she processed whether that was the right way to put it. Inasmuch as this is really happening, she'd always been this, always been her; but there had to date been a certain naturally occurring presentation, a performance, even in her most vulnerable moments. What is it like to be this version of me? How do I walk? How do I experience intimacy?

And it would be perfectly valid to touch her penis and call it a woman's orgasm. That's perfectly on point and fine. But something well inside Kelsey's ass was humming and tickling with request. She had the toys, though something told Kelsey it would all feel different now. Was it time to try? Her penis and ass chorused yesplease!

The curtains and blinds were all closed. For once, she wasn't going to treat her own body and its pleasure as something to hide in her own home, there was no lurker in the next room, she had her whole home in which to unleash herself. She left the windows wide open, always enjoying the feeling of cold air on her skin. She kept on a satin pyjama top but nothing else, and her penis peaked up from it and arched high upwards, already giving her a very erotic countenance. A matching satin sheet was draped across a comfy office chair and atop it was placed her toy, a rather large orange buttplug, already slick and ready. She loaded up her actualized reflection in front of her a little below eye level, looking away until the image manifested.

Kelsey smiled at herself like a new friend coming to her door.

She was ready for it all, but Kelsey still affectionately touched her chest through the satin, her neck, her tummy. She had always loved touch, but seeing herself with tresses of mid-length hair and reddened lips had somehow opened up interests in new kinds of touch, gentle explorations.

Allowing herself to now become explicitly sexual, but maintaining eye contact, she now soaked her left hand in lube and began her first touch tantamount to fucking herself: a lovely little angel touch in teeny circles around her opening, and then more broadly gently played back and forth with her ass. Kelsey found she liked watching herself in pleasure now, it was a rather attractive thing: the open mouth, the arch back of her neck, the bashful smile... She was flirting with herself as she teased the crack of her bum and the warm opening into herself.

There was no rush, there mustn't be. She just watched herself and let her ass tell her how far outside/inside to go. Slowly her relaxing muscles invited the fingers further in, centimeter by centimeter; and still she slid around, only occasionally probing a little inside, a little further, a little further, and gently around the area. Progress into her body was strictly by her body's request, and the permission to stay closed coaxed her body to gladly open.

When the next "moreplease" sensation came from inside her, Kelsey withdrew her fingers, and, transferring them to her silk-soft and sensitive scrotum with soft caress, she inched down on to the toy, preparing for the beginnings of contact.

Kelsey gazed at her reflection's affectionate look back at her. She smiled approvingly at herself, a sensual gleam and then a stare of fondness. And she moved down. The cool yielding material of the toy began to part the folds of her opening and enquiringly slide a little inside. With a big breath in and a deep breath out, Kelsey descended. It went further in, and it felt full and lovely, and then more, until a threshold of size was felt halfway down the plug. The woman held the reflected gaze and touched her penis with her right hand, softly tickling all around. Her ass tightened with the pleasure and anticipation, and she paused the various stimulations to relax her opening again.

This went on for a moment, quite enjoyably but with the risk of becoming awkward and logistical. Kelsey got mentally ready to relax her sphincter to try again, breathing meditatively, until she looked at her flushed pleasure face again as she began her descent. As she came up to change her angle, what she saw wasn't someone awkwardly negotiating an object into her ass, but a flirty woman sashaying her hips back and forth up and down as she sultrily girl-on-top fucked someone. The way the phone had slipped down a little made of the image a woman looking down at her lover as she slid up and down, playfully and tenderly lovemaking.

Kelsey found in herself a moment of true beauty as a woman and fawned at herself as she slowly humped up and down, watching her whole body move sexually. Gradually Kelsey became more animated, more elaborate in her movements. This wasn't even just a performance, there was wondrous pleasure in her ass, and her penis was for the moment incidental as she eagerly sought stimulation and depth inside and far within her, again and again. Come deep within me, let me feel you, let me ride you, this is how I look as I fuck you and you love it.

As minutes went on she didn't mind one whit not having passed the buttplug's threshold, she was experimenting with this new series of movements in her hips, and as she let go to the moment her body developed a full and holistic script for how to move, some instinct brought alive in a sudden imperative. She touched her chest, so softly, letting her nipple and its surrounding area feel nice and activate other areas of interest across her pleasure network; and, moving on for a moment from her buttery-slick foreskin with its ample arousal she raised her arms together, hands reaching over and behind her head as she fucked the object deep within her. Her pelvis instinctually knew (or soon discovered) a kind of swiveling motion, grabbing tight with her ass while twisting to the left, twisting back to the right, and releasing, racing back to repeat the motion. If this was a penis with foreskin its owner would be overwhelmed and ecstatic, and Kelsey was enraptured with the pleasure, the discovered talent, and the feminine gorgeousness of what she was doing.

Leaving alone the image of herself for the moment Kelsey closed her eyes and let her body move freely in this unleashed fervour, only wishing she truly had this long hair so it would tickle her chest and back as she swiveled and thrusted.

Kelsey opened her eyes eventually, and smiled mischievously with a toothy gleam at her own flushed and joyous face, her body relaxing and opening up in more ways than one. Apparently it literally was, because as she relaxed her ass again to slide the object deeper inside her with increasing boldness and another playful twist of her bum, the toy's rather large base slipped past her ass' narrowest pigeonhole, the inner sphincter and was suddenly all the way in.

The surprised flex of that muscle as she felt the momentary hugeness made the object rush even deeper, in an artificial hump, farther than anything ever before, all a rush of surprised sensation. The feeling was for just an instant too much for her, and her body almost decided definitely she was in pain if not peril, until, once the threshold was past and filled only with the narrowest part, the larger swell of the toy in a comfortably open area deep inside and the tip in a deep exploration, her body insisted exactly where to be touched to transform the moment into the orgasm it nearly was.

So Kelsey tickled just in front of her ass where the object entered, with a single finger on the tip of her sphincter, and two fingers of the other hand encircled the soaked foreskin lovingly. Her own ass reacted with a rhythmic pulse, and all of a sudden the woman realized what a buttplug was for. Because of the exact shape between the handle and the base, every pleasure-flex of her ass grabbed the toy and thrust it deeper. It was as though some telepathic lover was fucking her in perfect synch with her own pleasure.

The inside of Kelsey's ass, the outside of Kelsey's ass, Kelsey's slick foreskin, those three places received abundant love and touch all at once, and while the touch on her penis was only slight, that penis, larger than it usually was from all this pleasure and erotic celebration, began its first orgasm as a woman. It was several seconds away but it was now inevitable.

Kelsey gazed again at her reflection and committed to watching the whole thing unfurl, like a lover does to a lover: the beholding at the point of orgasm, like being held through it. As her bum thrust forward and back in increasing bucks, she let herself indulgently groan and whimper, delighted at the undignified and full noise of her rather elaborate orgasm. It lasted for uncountable moments, not a single instant but a gradual full event across the system of her body. It continued even as she had completed a full ejaculation across her left palm, her ass and chest still celebrating the sensations, and experimentally she let one hand touch her open mouth as she watched the event continue. As the sex waned into completion, she watched the aftermath, a frazzled but elegant woman with cum across her mouth, visibly happy though too winded to smile, gazing as though at someone she was in love with that she had just invited into her body. As though she was now holding cum inside her like something precious.

This moment needs to happen for real. I am a woman; that much is obvious. And one day I'm going to let someone inside me and love their cum right out of them. I will just dance my body atop them until I sashay their orgasm right out of their body into mine. I can't fucking wait. But for tonight, I just made love to myself, and I'm not pretending.

"Hey, Kelsey: I love you."