The Day I Went Out Dressed as a Tranny for the First Time
Don’t expect a story full of penetrative sex. To a certain extent it’s going to sound boring, I know. But girls like me understand the thrill and the kink of that first day we dare to go out on the street as who we really are. That step, the first one, is never forgotten. And although that night there was no real fucking, there were hands, mouths, hard cocks pressing between my ass cheeks, and a brutish arousal that still makes me put my hand between my legs when I remember it.
It happened years ago, in a town in the center of the country that I’m not going to name so as not to give myself away. What I can tell you is that I didn’t do it alone. Renata, my girlfriend at the time, helped me. An incredible woman with whom I also shared a liberal scene: we were in an open relationship and had a wonderful time discovering things together. She was the one who gently pushed me to stop hiding inside four walls.
—Today we go out —she told me that morning, while I was still hesitating in front of the mirror—. Today the world sees you. And if someone gets a hard-on for you, even better.
The outfit had been chosen the night before, amid laughter and nerves. A jumpsuit with a denim skirt and white platforms like the pole dancers wear, sky-high, shiny, impossible to ignore. I still have them. I shaved my legs centimeter by centimeter, slowly, feeling how the razor left my skin smooth and strange to the touch. I also ran the blade over my balls and over my ass crack, perched on the edge of the tub, with Renata watching me from the doorway and biting her lips. When I finished, she came over, spread my ass cheeks with both hands, and stuck her tongue into the freshly shaved hole.
—Not yet —I said, laughing, pushing her away—. If you get me to a hundred now I won’t be able to go out.
—You’re going to have a hard-on all day —she answered, squeezing me over my panties—. It’s going to show on your face, babe.
She was right. The bulge was already showing in my lace panties, and she knew it. She squeezed one fake tit with the other hand, gave me a sharp slap on the ass, and shoved me toward the mirror.
This is serious. Today I’m really going to do it.
I adjusted the wig, put on my makeup with my hands trembling a little, and when I finally looked at myself full on, I didn’t recognize myself. And I loved that. I looked good. I looked sexy. I looked like a gorgeous little slut ready to be looked at. Renata appeared behind me in the reflection, wrapped her arms around my waist, and whispered in my ear that I was beautiful. I believed her.
***
The first destination was a burger joint on the main avenue. It was early and the place was full of ladies drinking coffee, the kind who seem to keep an eye on everything. While we stood in line, I was convinced that at any moment someone would call us out, point at us, tell us to leave.
None of that happened.
On the contrary. An older woman came up to the table with a huge smile.
—Sorry to bother you —she said—, but that wig looks divine on you. Where did you buy it?
I was speechless for a second. Renata answered for me, delighted, and suddenly we had two or three women weighing in on the color, the cut, how well it matched my skin tone. The real triumph, though, was the platforms. Everyone wanted to know where to get the same ones. I walked out of there several centimeters taller than when I walked in, and not just because of the shoes.
—See? —Renata told me in the car, squeezing my hand and taking it straight to the bulge that had refused to go down since morning—. I told you. And look how hard you are, you little slut.
I still didn’t quite believe it. All my life I had imagined contempt, mockery, the judging look. I had whole scripts memorized about how to defend myself, what to answer if someone insulted me. And it turned out the first person who spoke to me on the street did so to pay me a sincere compliment. Something settled inside me that morning, a piece that had been crooked for years and finally fit into place.
***
Buoyed by the first victory, we went to a notary’s office to pick up some papers from her job. Renata went inside; I stayed outside. And that was where I committed my little madness of the day: instead of waiting in the car, I got out and stood on the sidewalk, in full view of everyone.
The people passing by kept looking at me. Men, women, people in a hurry who still turned their heads. A guy in a suit looked me up and down, stopped for a second to watch how the skirt clung to my ass in the breeze, and I felt myself getting wet with pure excitement, front and back. My cock throbbed inside my tight panties. My heart pounded in my throat. My most concrete fear, the one squeezing my stomach, was that someone would get the idea to call the police and I’d end up arrested for soliciting on the street. It sounds exaggerated, but at that moment, freshly out of the shell, it seemed like the worst possible ending.
It didn’t happen. Renata came out with the papers, found me standing there, and burst out laughing when she saw my face, a mix of panic and pride.
—You’re enjoying this more than you’ll admit —she said, slipping her hand under my skirt right there, with a quick gesture, and feeling my cock dripping pre-cum inside my panties—. Look at you, you’re soaked, you filthy girl.
She was right.
***
From there we went to a shopping mall. We were euphoric, both of us talking at once, going over every look, every comment, every gesture. There was only one practical problem, and it was pretty awkward to deal with: the excitement wouldn’t go down. I’d spent the whole day with an erection that gave me no respite, and the jumpsuit didn’t help hide it. I walked carefully, minding my angles, crossing my legs when I sat, praying no one would notice how the tip of my cock was pressing against the fabric.
We decided to go into the movie theater to watch a comedy that was in style, one of those that fill up the screening rooms. The movie was the least important thing. What was odd was the procession of theater employees who kept going in and out of the auditorium, passing by our row again and again with flashlights on. I was sure they were looking for something, hoping to see something, maybe hoping we would do something.
—They’re checking us out —I whispered to Renata.
—Let them look —she answered, and slid her hand over my naked thigh in the dark.
Her hand didn’t stop at my thigh. It kept climbing slowly, pushing aside the denim skirt, until her fingers slipped into the waistband of my panties and found my cock completely soaked. She took hold of it with a firm fist, squeezed the head until I let out a gasp I had to smother into my own hand, and started jerking me off very slowly, very discreetly, taking advantage of every burst of laughter in the room to pump a little faster.
—You’re leaking, pig —she whispered in my ear—. Your stains are going to show on the jumpsuit and they’ll kick us out of the theater.
I couldn’t even answer. One of the employees passed by again with the flashlight, the beam brushed my knees, and Renata didn’t even flinch: she kept wanking me while the guy walked away down the aisle. With her other hand she reached behind me, slipped two fingers between my ass cheeks over the fabric, and started pressing my shaved hole, the one she had licked that morning. I almost came right there, in the seat, with two employees circling three meters away. I grabbed her wrist and stopped her just in time.
—Save some for tonight —I begged, voice breaking.
She laughed, brought her fingers to her mouth, and sucked them slowly, looking me straight in the eyes.
Since none of the employees dared say anything out loud, it all stayed as pure tension, sidelong glances, and that tingling feeling of being watched. For me, who had spent my whole life hiding, being watched with desire instead of rejection was a new and powerful drug.
***
But the total success, the one I still remember with my heart racing to this day, came at the end of the afternoon. There’s a food market on the way out of town, right on the highway heading toward the capital. A stopover place, with long tables and steaming broths, where truckers and haulers pull in to eat before hitting the road again.
A lot of truckers. A lot of haulers. And that night we confirmed something: they’re bold, direct people, no beating around the bush.
As soon as we sat down, the looks started. Different from the movie theater, different from the notary’s office. These were hungry male looks, looks that held, that didn’t look away, that ran over you completely and stayed there waiting for an answer. Renata was just as turned on as I was; I could tell by the way she squeezed my knee under the table and by how her hard nipples showed through her blouse.
One of them, a big guy in a plaid shirt, came over with two beers we hadn’t ordered.
—Can I buy you those? —he asked, and sat down without waiting for an answer.
Two others came after him, one younger and another with a graying mustache who looked like the boss of the group. Conversation, laughter, hands brushing “by accident” over the plastic table. They asked where we were from, where we were going, whether we came here often. I answered in monosyllables at first, still testing the waters, but little by little I loosened up and started flirting, returning their looks, laughing at their bad jokes. The mustached one slipped his hand under the table onto my thigh and kept moving it upward with complete calm until he touched my bulge over the fabric and stayed there, squeezing, staring at me with a wicked smile.
—Well now, what a little surprise, mommy —he said quietly, so only I could hear—. And you’ve got it nice and hard.
He didn’t pull away. On the contrary: he licked his mustache and kept squeezing. The guy in the plaid shirt, on the other side, had already draped his arm over Renata’s shoulders and had a hand inside her blouse, playing with her nipples without the slightest attempt to hide it. One of them suggested, with a naturalness that left me breathless, that I go up with him to the cab of his trailer, parked a few meters away, in the dark.
Do it. This is the night.
I didn’t do it. For safety, because I didn’t trust them, because they were strangers in a remote place, and because I still didn’t feel ready for that much. To this day I still regret it a little. But what did happen that night stayed burned into me.
We got up from the table and let ourselves be led a few meters farther, to a dark corner between parked trucks where the market light didn’t reach. The three of them surrounded us. The mustached one grabbed me by the back of the neck and kissed me with his whole tongue in my mouth, while the younger one slipped his hands inside my jumpsuit from behind, groped my fake tits, and pinched my fake nipples until I moaned. The guy in the plaid shirt had already opened his fly and had Renata’s hand inside his pants. Out of the corner of my eye I could see my girlfriend taking it out and wanking him while she stared at my face, dying of kink.
—Touch it, babe —the mustached one whispered, grabbing my wrist and bringing my hand to his crotch—. You won’t regret it.
His cock was rock hard, thick, hot over his jeans. I unbuttoned him without a second thought and pulled it out. It was big, with an swollen glans and a thread of pre-cum sliding down to his fingers. I wrapped my hand around it and started jerking him off slowly, feeling it throb against my palm. The younger one, behind me, had already pulled down the waistband of my jumpsuit and my panties to halfway down my ass, and was jamming his cock between my shaved cheeks, not pushing it in, rubbing it up and down along my crack while he squeezed my hips with both hands.
—What a little ass, you bitch —he panted in my ear—. What a whorish little ass you’ve got.
Mine was bulging against the fabric of the jumpsuit in front, dripping again, and the mustached one bent down, pulled it out of my panties, and put it in his mouth for a moment, just a long suck with his lips sealed that made my legs tremble. Renata, meanwhile, had one trucker jerking off in her hand and the other kissing her neck, and she didn’t take her eyes off me. She was smiling, proud, aroused, enjoying seeing me turned into the center of the feast.
I had arrived thinking they would smell like the road, travel sweat, fatigue. And to my surprise, all three smelled good, of freshly applied cologne, as if they had dressed up on purpose before coming down to eat. Feeling their big hands on my waist, their beards scraping my neck, three hard cocks rubbing against me at once front and back, three hungry mouths focused on me, was far more than I ever imagined for my first day out.
I didn’t let any of them come, and I didn’t come either. When the younger one started pressing the head too hard against the hole, when I felt that any second he was going to push in and there’d be no turning back, I pulled away, grabbed Renata’s hand, and told her in her ear that we should go. She understood instantly. We got our clothes back in order as best we could, thighs trembling and mouths swollen from so much kissing, and walked out of there fast, leaving them with their cocks out and a rough laugh of a man only half-satisfied.
***
We had gone quite far from town, so the walk back to the car was a whole procession. So many people saw us. I walked on those impossible platforms, still tasting kisses in my mouth, with my panties soaked in my own pre-cum and my fake nipples burning from how much they had been squeezed. I could feel everyone turning to look at me as I passed.
I imagined what they were thinking. There goes the roadside little slut, arm in arm with her girlfriend, with her cock still hard under the jumpsuit. And the strange thing, the thing it took me years to understand, is that thought didn’t hurt me. It made me feel alive. For the first time in my life I wasn’t hiding inside a room or disguised as something I wasn’t. I was out there, in plain view, being desired, being looked at, being exactly who I wanted to be: a beautiful whore, standing her ground in the world, without asking permission.
Renata opened the car door for me, kissed my temple, and we drove off in silence, both of us grinning like idiots, hands intertwined and our panties both a sticky mess.
There was no real fucking that night, I already said that. But there were three hard cocks in my hands, someone else’s tongue in my ass that morning, a discreet handjob in the cinema, and the certainty that from then on I could go out into the street to be looked at, to be touched, to be desired. And there was something that for me was worth far more than all of that together: the day I stopped being afraid of myself. I still keep those white platforms. Every time I see them in the closet, I feel again the thrill, the kink, and the happiness of that first step onto the street. And I remember again how lucky I was to take it hand in hand with someone who loved me.