My Cross-Dressing Fantasy: One Night with a Stranger

This time I haven’t come to tell you about something that already happened. I’ve come to confess a fantasy I’ve been carrying around for far too long and that, with any luck, I’ll dare to fulfill soon. I say “with any 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 I go on, you should know 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 to surrender, spread my legs, let myself be fucked slowly and deeply, to let go of the control I have to maintain all day 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 some guy who has just turned forty. I mean fifty, sixty, even older. Men who have lived long enough not to be in a hurry, who enjoy a cross-dresser willing to be treated like a submissive, compliant little slut, made to have his 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 shows in everything: in the patience of his hands, in the way he spoke into my ear while he fucked 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 to what he wants, comes in three minutes, and leaves; a sixty-year-old savors the journey, 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 him 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 meet. Someone who arrives with his cock hard from imagining me, wanting what I want to give.

One night. No promises, no tomorrow, no real names if he doesn’t want to give them. Do everything to each other, without prejudice or reservations: let him put it in my mouth, my ass, in every position he feels like, let him come wherever he wants, and afterward let us remain a beautiful memory that 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-groomed. A man who isn’t uncomfortable with me being a cross-dresser, who doesn’t experience it as a shameful secret but as an acknowledged desire. Someone willing to suck me too, to lick my ass if he likes, to enjoy every part of my body without leaving a corner untouched. I’d like to feel that immediate chemistry, the kind you can’t fake, the kind that appears the moment two eyes meet and you know the night will end with both of you drenched in sweat and cum.

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

Let me tell you how I imagine it, because fantasy isn’t only about what, but how. It’s the detail that keeps me awake and makes me masturbate in the early hours, biting the pillow so I won’t make a sound.

***

I imagine him arriving early, in the room of some ordinary hotel in the city. One of those anonymous rooms with heavy curtains and warm lighting that forgives everything. I would arrive first so I could get ready calmly, because the transformation is part of the ritual and I don’t want to do it in a hurry.

In front of the bathroom mirror, I would take my time. First the foundation, then the eyes, the eyeliner that’s so difficult for me to get even, the lipstick in a red I would never wear in my other life, a red meant to leave a mark at 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 difficult to explain how it feels. It’s like putting on a skin that fits better than my own, a skin asking to be touched, licked, penetrated.

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

I want him to look at me from the doorway without saying anything yet, slowly taking me in with his eyes. Let him see the bulge of my cock contained beneath the fabric and lick his lips. Let his first words be a compliment spoken softly, the sort an older man knows how to give without making it sound rehearsed.

—You’re beautiful —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 small gesture of respect puts me in the place I want to occupy that night: the well-brought-up little slut who is going to do everything he asks.

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

I want to feel those mature hands holding my hips, pulling me against him, his hard bulge pressing against mine. I want him to caress my buttocks with that calm firmness only men who no longer need to prove anything possess, to part my cheeks over the fabric and run a finger between them, searching for my hole, marking his territory. Let him trace my thighs upward, slowly, until he makes me tremble and beg for more before he’s even stripped me completely.

***

I imagine him taking off my clothes, piece by piece, without ripping anything away, uncovering me like someone opening a gift he knows he’s going to enjoy. The panties sliding down my thighs, my cock springing free, hard and curved, wetting itself at the tip. I’d like to stand before him, exposed, my cock erect and my silicone breasts throbbing beneath my skin with nervousness, 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; to me it’s proof of everything that man already knows how to do with a cross-dresser like me. Run my fingers over the nape of his neck, feel the roughness of his freshly shaved cheek, kiss that masculine face I’m so attracted to while I unbuckle his belt without taking my eyes from his.

And then move lower. Kiss his neck, his gray-haired chest, feel his breathing change beneath my lips. Go lower still, slowly, listening to the air escaping between his teeth when I kiss his belly. Pull down his pants, then his briefs, and come face-to-face with his cock: big, thick at the base, with those prominent veins only big men’s cocks have. I’d like to kneel before him and look up from below with my mouth slightly open before I began, because that look says everything: tonight I’m his, do whatever you want to me, use my mouth however you like.

That’s the exact moment when 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 throb against my lips. Kiss his balls one by one, suck them gently, look at him while I do it to see the expression on his face. And then wrap my mouth around his glans, squeeze it with my red-painted lips, slowly take it in until it reaches the back of my throat and makes my eyes water. I’d like to gag a little, let strings of saliva hang from my chin, the kind of saliva that only appears when a girl is doing her job properly.

I want to suck his cock while taking all the time in the world, attentive to every reaction, to the way he rests one hand on the back of my neck, not to push, but to guide me. Pull it out and masturbate him against my face, rub it over my lips, my cheeks, my tongue sticking out. Take it back in all the way and feel it vibrate. I like feeling that a man is truly enjoying himself, that he isn’t acting, that his shoulders loosen and his voice grows uneven, that he begins to say “that’s it, slut, that’s it,” softly, hoarsely, almost to himself.

And afterward I’d like him to lift me carefully by the hair, take me to the bed face down, and have his turn. Let him kiss my entire body without skipping a single spot, as if every inch deserved attention. Let him spread my cheeks with both hands and bury his face there, lick my ass slowly, wet my hole with his tongue, slipping it in and turning it until he makes me moan into the pillow like a bitch in heat. Let him whisper to me while he does it, the dirty things an older man knows how to say that make me feel like the little slut I am when I transform: “what a sweet little ass you have,” “I’m going to fuck you slowly,” “you’re going to be my little woman tonight.”

Then the lubricant. One finger. Two. Feeling him open me patiently while his other hand masturbates my cock, dripping onto the sheets. Once I was opened properly, he would turn me onto my back, put a pillow beneath my hips, hook my legs over his shoulders, and ease his cock into me, inch by inch, looking me in the face to read whether he was hurting me or whether I was enjoying it. And when he was all the way in, he would stay still for a moment, deep inside me, letting me feel his weight.

Then he would start moving. At first gently, with long, deep thrusts, never pulling all the way out. Then harder, gripping my hips, making his balls slap against my ass with every thrust. Change positions without coming out: put me on my side, spoon me, fuck me from behind while biting my shoulder. Then put me on all fours and grab me by the wig as if it were my own hair, pull me backward, and fuck me the way you fuck a female who asked to be treated that way.

I want to come 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 grunt, feel his whole body tense over mine and his warm semen fill me from within. Let him stay still there, breathing against the nape of my neck, until his cock slowly begins to soften inside my ass.

***

I’m not going to lie to you: the part I like most about the entire fantasy isn’t the sex itself, although sex is the main course. It’s what happens during it. It’s that feeling of being fucked and cared for at the same time, of having a cock inside me and a warm hand caressing my face, of being able to let everything go and obey, of not having to decide anything because there’s someone above me who knows what he’s doing and takes me where he wants me to go.

I imagine surrendering completely, letting him dispose of my body as he pleases, attentive to his most intimate desires, opening my legs when he wants them open, kneeling when he wants me at 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 everything, the one who endures. With him, even if only for one night, I wouldn’t have to hold up anything except his thrusts.

And I’d like things not to end abruptly. Let us stay there in silence for a while afterward, his arm across my waist, his semen slowly running down my thigh, our breathing gradually returning to normal. I like that part as much as the other. Sex gives me pleasure, but that time afterward, dirty, used, held, gives me peace.

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

***

I think this fantasy became so recurring for a reason I hadn’t dared say out loud. I’m fairly sure the time is approaching when Mora will have to hang up her heels for good.

I don’t see myself doing this for many more years. There’s a time 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, my cock gets hard on its own at the thought of scenes like these, and I still like my face when I see myself made up in the mirror. But the logic of life is merciless, and everything starts going downhill with age. I know that. That’s why this fantasy presses against my chest with a new urgency.

I don’t want to reach Mora’s final stage with my head full of “if onlys.” I don’t want to look back and realize fear won. I want to have at least that night, one perfect, filthy night, to keep with me. Something of my own that no one can take away when there’s nothing left of the woman I am before the mirror.

I’m afraid, of course I am. Afraid the stranger won’t be as I imagine him. Afraid reality won’t resemble the fantasy. Afraid, above all, of daring to do it. It’s easier to write this with my free 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 left unspoken die quietly, and I don’t want this one to die. That’s why I’m writing it. Writing it is my way of beginning to make it real, of releasing it into the world to see if someone picks it up.

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

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