My Cross-Dressing Fantasy: One Night with a Stranger

This time I’m not coming to tell you something that already happened. I’m here to confess a fantasy I’ve been carrying for far too long and that, with luck, I’m going to dare to fulfill soon. I say «with luck» because at thirty-three there are many things that scare me, and insecurity weighs on me more than I’d like to admit.

Before going on, it’s worth telling you something about me. My cross-dressing side is strictly closeted. No one in my daytime life suspects that Mora exists, which is what I call myself when I transform. At this stage of my life I enjoy receiving much more than giving, and I think you already understand what I mean. I like giving myself over, spreading my legs, letting myself be fucked slowly and deep, letting go of the control I have to hold onto all day long with my teeth clenched.

If you’ve followed my stories, you know I have a strange weakness: mature men. And when I say mature, I’m not talking about a guy who’s just turned forty. I mean fifty, sixty, even older. Men who have already lived enough not to be in a hurry, who enjoy a cross-dresser willing to be treated like a submissive little slut, eager to have their cock emptied inside her.

I haven’t had many experiences, I’m not going to exaggerate. But the few I’ve had were delicious. The difference with an older man is noticeable in everything: in the patience of his hands, in the way he spoke to me in my ear while he was fucking me, in how he took me without rushing, as if we had the whole night ahead of us and nothing else mattered. That calm melts me. A twenty-year-old goes straight for what he wants, comes in three minutes and leaves; a sixty-year-old savors the path, opens me up properly and makes me beg for more.

All right, but I owe you the fantasy. Here it is.

I want to convince a stranger to spend a night with me in a hotel and transform myself for him. But not just any stranger. I’d like it to be someone who has read my stories, someone who already knows me through these words and knows exactly what kind of cross-dresser he’s going to find. Someone who arrives with a hard cock from imagining me for so long, wanting what I want to give.

One single night. No promises, no tomorrow, no real names if he doesn’t want to give them. Doing everything to each other, without prejudice or reservations: letting him fuck my mouth, my ass, in every position that occurs to him, letting him cum wherever he wants, and then staying behind as a beautiful memory each of us keeps to ourselves. I’m not looking for a boyfriend or a love story. I’m looking for one perfect, filthy night, the kind you remember years later with your hand between your legs.

I imagine him healthy, discreet, masculine, well kept. A man who wouldn’t be bothered that I’m a cross-dresser, who wouldn’t live it as a shameful secret but as a desire he’s embraced. Someone willing to suck me too, to lick my ass if he likes it, to enjoy every part of my body without leaving a single corner out. I’d like to feel that immediate chemistry, the kind you can’t fake, the one that appears the moment two glances meet and you know the night is going to end with both of you soaked in sweat and cum.

I wonder if I already know him. If right this very moment someone is reading this with his cock in his hand, thinking he could be the one.

Let me tell you how I imagine it, because the fantasy isn’t just the what, it’s the how. It’s the details that rob me of sleep and force me to masturbate in the middle of the night, biting the pillow so I don’t make noise.

***

I imagine him early, in the room of some random hotel in the city. One of those anonymous rooms with heavy curtains and a warm light that forgives everything. I would arrive before him to get ready calmly, because the transformation is part of the ritual and I don’t want to do it in a rush.

In front of the bathroom mirror I would take my time. First the foundation, then the eyes, the eyeliner I struggle so much to make even, the lipstick in a red I would never wear in my other life, a red meant to leave its mark on the base of a cock. And finally the wig, that exact moment when I stop being who I am by day and Mora appears. It’s hard to explain what it feels like. It’s like putting on a skin that fits better than your own, a skin that begs to be touched, licked, penetrated.

I imagine myself waiting for him seated on the edge of the bed, in black lingerie chosen with him in mind, my panties barely covering my cock, already half hard, stockings with a garter belt, freshly shaved legs and a sweet perfume floating in the air. Hearing the key card at the door. The doorknob. And then seeing him come in.

I want him to look at me from the threshold, still saying nothing, taking me in slowly with his eyes. To see the bulge of my cock held under the fabric and lick his lips. For the first word to be a compliment spoken softly, the kind an older man knows how to say without sounding rehearsed.

—You’re gorgeous —he’d say, setting the keys on the table without hurrying—. A little doll.

—I did it for you —I’d answer, and I’d like to address him formally at first, because that little gesture of respect puts me in the place I want to occupy that night: the well-behaved little slut who is going to do everything he asks.

For him to come closer without rushing. To take my face with one large, warm hand and tilt my head to kiss me. A long, deep kiss, with tongue inside, the kind you feel in your stomach and between your legs at the same time. And while he kisses me, for his fingers to slide down my neck, over my collarbone, down my back, and for one hand to slip under my panties to grab my cock and feel how hard it gets all at once between his fingers.

I want to feel those mature hands holding my hips, pressing me against him, noticing his hard bulge against mine. I want him to stroke my ass with that calm firmness only men who no longer need to prove anything have, to part my cheeks over the fabric and run a finger between them, searching for the hole, marking territory. To trail up my thighs slowly until I’m trembling and begging for more before he’s even taken my clothes off completely.

***

I imagine how he would take my clothes off, piece by piece, without ripping them, uncovering me like someone opening a gift they know they’re going to enjoy. The panties sliding down my thighs, my cock popping free, hard and curved, the tip wet on its own. I’d like to stand in front of him, exposed, with my cock standing and the silicone tits under my skin throbbing from nerves, letting his eyes do the first work before his hands.

I want to stroke his hair while he looks at me. Hair full of gray, because I like gray hair; it seems to me proof of everything that man already knows how to do with a cross-dresser like me. To run my fingers over the back of his neck, feel the roughness of his freshly shaved cheek, kiss that masculine face that attracts me so much while I unbuckle his belt without ever breaking eye contact.

And then keep going down. Kiss his neck, his graying chest, feel his breathing change rhythm beneath my lips. Go lower, slowly, hearing the air escape between his teeth when I kiss his stomach. Pull down his pants, then his boxers, and find myself face-to-face with his cock: thick, heavy at the base, with those pronounced veins only the cocks of big men have. I’d like to kneel in front of him and look up at him, mouth parted, before I begin, because that look says it all: tonight I’m yours, do whatever you want with me, use my mouth however you want.

It’s there, in that exact instant, where my fantasy becomes unbearably real.

I want to run my tongue along the entire length of his cock, from bottom to top, slowly, feeling it pulse against my lips. Kiss his balls one by one, suck them carefully, look at him while I do it to see the face he makes. And then wrap the head in my mouth, press it with my red-painted lips, sink it in slowly until it reaches the back of my throat and brings tears to my eyes. I’d like to gag a little, leave strands of saliva hanging from my chin, that saliva that only appears when a woman is doing her job well.

I want to suck his cock taking all the time in the world, attentive to every reaction of his, to the way he rests a hand on the back of my neck, not to push, but to guide me. Pull it out and jerk it against my face, smear it over my lips, over my cheeks, over my tongue sticking out. Take it back in to the hilt and feel it throb. I like feeling a man truly enjoying himself, not pretending, his shoulders loosening, his voice breaking, beginning to say «like that, slut, like that,» low, rough, almost to himself.

And then I’d like him to lift me by the hair carefully, take me to the bed face down, and have his turn. To kiss my whole body, without skipping a single corner, as if every inch deserved attention. To part my ass cheeks with both hands and bury his face there, to lick my ass slowly, wetting my hole with his tongue, pushing it in, circling it, until I’m moaning into the pillow like a bitch in heat. To whisper dirty things in my ear while he does it, the kind an older man knows how to say and that make me feel like the little slut I become when I transform: «what a tasty little ass you’ve got,» «I’m going to fuck you slowly,» «you’re going to be my little woman tonight.»

Then the lube. One finger. Two. Feel him open me patiently while with the other hand he jerks my cock, dripping onto the sheets. When I was open enough, turn me onto my back, put a pillow under my hip, hook my legs over his shoulders, and slide his cock into me slowly, centimeter by centimeter, looking at my face to read whether he’s hurting me or pleasing me. And when he was all the way in, stay still for a moment, inside, deep, letting me feel his weight.

Then start moving. First gentle, with long, deep thrusts, never pulling out completely. Then harder, gripping my hips, making his balls slap against my ass with every stroke. Change positions without pulling out: put me on my side, spooning me, fuck me from behind while he bites my shoulder. Then put me on all fours and grab me by the wig like it’s my own hair, pull me back and fuck me the way you fuck a female who asked to be treated that way.

I want to cum without touching myself, only with his cock inside me, splashing the sheets while he keeps fucking me mercilessly. And I want to feel him finish inside me, hear him growl, feel his whole body tense over mine and his warm semen fill me from the inside. For him to stay still there, breathing on my nape, until his cock starts slowly softening inside my ass.

***

I’m not going to lie to you: the part I like most about the whole fantasy isn’t the sex itself, even though sex is the main course. It’s the in-between. It’s that feeling of being fucked and cared for at the same time, of having a cock inside you and a warm hand stroking your face, of being able to let everything go and obey, of not having to decide anything because there’s someone on top of me who knows what he’s doing and takes me with him.

I imagine giving myself over completely, letting him use my body as he pleases, attentive to his most intimate desires, opening my legs when he wants to open them, getting on my knees when he wants me in his mouth, giving him my ass when he asks for it. That’s the word: surrender. A surrender I never allow myself in my daytime life, because there I’m the one who has to be in charge, the one who solves things, the one who endures. With him, even if only for one night, I wouldn’t have to hold anything up except his thrusts.

And I’d like things not to end abruptly. For us to stay a while in silence afterward, his arm crossed over my waist, his semen slowly dripping down my thigh, our breathing gradually returning to normal. I like that part just as much as the other. Sex gives me pleasure, but that little time afterward, dirty, used, held in an embrace, gives me peace.

Maybe we’d talk a little. Maybe not. Maybe I’d turn around and suck his cock one more time, soft, calmly, just for the pleasure of having it in my mouth. Maybe we’d fall asleep and when we woke he’d leave early, without a fuss, letting me sleep. And I’d stay a little longer in that чужой bed, with my ass still open and burning, my makeup smeared and the wig off to one side, smiling to myself, knowing that night was exactly what I wanted it to be.

***

I think this fantasy became so recurring for me for a reason I didn’t dare say out loud. I’m pretty sure the moment is approaching when Mora is going to have to hang up her heels for good.

I don’t see myself doing this for many more years. There’s a season for everything, and mine has an expiration date. Today I can say, without false modesty, that I’m at my best: my body still responds, I get hard just thinking about scenes like these, and I still like my face when I see myself made up in the mirror. But life’s logic is relentless, and everything starts going downhill with the years. I know it. That’s why this fantasy squeezes my chest with a new urgency.

I don’t want to reach Mora’s final stage with my head full of «what ifs.» I don’t want to look back and realize fear beat me. I want to have at least that night, just one, perfect, filthy, to keep for myself. Something of mine that no one can take away when there’s nothing left of the woman I am in front of the mirror.

I’m afraid, of course I am. Afraid the stranger won’t be like I imagine. Afraid reality won’t look anything like the fantasy. Afraid, above all, to dare. It’s easier to write this with one hand between my legs than to do it with a real man waiting for me in a hotel. I know that better than anyone.

But I also know that fantasies that aren’t told die in silence, and I don’t want this one to die. That’s why I’m writing it. Writing it is my way of starting to make it real, of setting it loose in the world to see if someone picks it up.

I’m going to find a way to find that special someone. That older man, patient and discreet, with the big cock and warm hands, who wants to give me a night like that without asking for anything in return except the memory of my ass squeezing his cock. And if everything goes the way I dream, you’ll know where to find me: right here, in one of my next stories, I’ll tell you in loving detail how he fucked me, where he came, how many times he made me come.

In the meantime, I keep imagining him in front of the mirror, wig in hand, his cock hard against the fabric of his briefs, waiting for the moment I dare. Maybe that man is already reading with his hand busy. Maybe it’s you.