My First Date as My True Self at Last

Hi, my name is Renata. I’m thirty-one years old, and this is the first time I’ve dared to write here, even though I’ve been reading all of you silently for a long time. Today I finally found the courage to tell you about my first time with a man, my first boyfriend, and the night I stopped hiding and gave myself to him as the woman I’d always known I was.

From a very young age, I felt there was something different about me. I didn’t feel like the other kids my age. What really caught my attention was women’s clothing—its softness, its colors, the way it fell over the body. I have a younger sister, just a year and a half younger than me, and it was with her things that I began discovering all this. I tried on her dresses when no one was home, looked at myself in the mirror, and for the first time recognized myself.

That’s how I grew up, caught between fear and desire. I had one or two encounters with friends from the neighborhood, but it never went beyond a caress or a quick, nervous blowjob, with guilt always hot on my heels. I turned eighteen and started working, driving freight trucks along the southern highways. At last I had my own money and, above all, my own freedom.

I’ll never forget the first time I walked into a store alone to buy women’s clothes for myself. My hands were shaking. I felt that everyone passing me was guessing what I was doing, reading it on my face. I left with a full bag: a couple of lingerie sets, a dress, and a brown wig that fell a little below my shoulders. I walked to my parents’ house clutching the bag to my chest as if I were carrying stolen treasure.

I ran to my room and locked myself in to try everything on. I put on the wig and the dress, looked at myself, and something inside me finally clicked into place. Because of work, I was hardly ever home; I came back on weekends, sometimes not even then. But little by little I began wearing women’s underwear every day, beneath my men’s clothes, in the truck cab, at roadside stops. It became the most natural thing in the world. No one had seen me transformed yet, and a couple of times I was nearly discovered at home, but luckily I always managed to hide everything in time.

Until one day, the message that changed everything arrived.

***

It was strange from the beginning because he wrote to my male account, not the other one, the one I used as a woman. He was a guy. The message began with a simple “hi,” nothing more. Before replying, I carefully checked his profile. The truth was, he was handsome: broad shoulders, a confident smile, the kind of look that disarms you. So I gathered my courage and answered him.

After a few brief exchanges, he got straight to the point. He told me he’d seen me pass through town several times and that he liked me. I was speechless. It took me a couple of days to figure out what to say, and when I did, I confessed that I liked men too. His reply was immediate: he wanted to meet me in person.

I told him yes, but that it would take me a while to get there because I was traveling with the truck. And before going any further, I made the most important thing clear: I transformed into a woman, that was my truth, and I was still a virgin too. I blurted it all out, my heart in my mouth, certain that would be the end of everything.

It took him a while to answer. So long that I thought I’d scared him off and would never hear from him again. But after an agonizingly long time, his message appeared. He said he’d never been with anyone like me, that he’d only ever been with men, and that even so, he still wanted just as badly to meet me. I read those lines three times. I couldn’t believe it.

Several days passed before we could see each other. During that time, we texted all day and talked on the phone until we fell asleep with our cell phones against our ears. That’s how I ended up accepting him as my boyfriend over a phone call, just like that, without ever having seen each other in person. Crazy, I know, but by then we told each other everything. His name was Damián, and his voice had crept into every corner of my days on the road.

At last I was told I’d get a few days off as soon as I returned from my final trip. The moment I hung up with my boss, I called my love.

—Hi, sweetheart. Guess what? I’ve got fantastic news —I said, unable to contain my smile.

—Let’s hear it. Tell me —he replied.

—They’re finally giving me a few days off. And I’m dying to see you in person.

—That’s wonderful, gorgeous. At last I’ll get to have you right in front of me —he said, and just hearing him made my legs go weak.

***

We agreed to meet the day after I arrived, so I’d have time to get ready calmly and prepare everything I was going to take. I knew there would be no one at my parents’ house that day: they were going to a party and would be back late. I arrived and went straight to take a long bath, carefully shaved the little body hair I had, spread scented creams all over myself, and sat in front of the mirror to decide what to wear for my first real date.

I chose a black thong, bra, and garter set, with sheer stockings fitted tightly around my legs. I borrowed a pair of my sister’s high heels without permission, brushed the wig, prepared my makeup, and finally chose a black dress so short it barely covered the top of the stockings. That night I hardly slept from nerves. I tossed and turned in bed, imagining what it would be like to have him close, what it would feel like to have a real cock entering my ass for the first time.

When I woke up, I already had a message from him. He told me how anxious he was, that he hadn’t been able to sleep either. I didn’t really understand what was happening inside me, but I think I was falling in love, even though I hadn’t seen him in person yet. Then he wrote again: his parents had taken the car, and he asked me, if it wasn’t a problem, to come pick him up.

I told him yes, gladly, even though that changed my plans. I’d intended to wait for him already transformed into Renata. So I put on all my lingerie and the dress beneath my men’s clothes, so I wouldn’t waste time when we got to the hotel and could finish getting ready quickly. We lived in the same town, so the trip was short.

When I arrived where he was waiting, I moved to the passenger seat so he could drive and take me wherever he wanted. On the way, we were both so nervous that we barely said a word. He stopped to buy some beers, and we continued on. My stomach was tied in knots as I glanced at him, thinking that before long I’d be naked in front of a man for the first time in my life, my legs spread and his cock sinking into me.

We reached the hotel, and I went straight to the bathroom to finish getting ready. I let down my wig, touched up my makeup, adjusted my dress, and took a deep breath. When I came out, he looked me up and down. I was the one who broke the silence.

—How do I look, love? Do you like me? —I asked, playing with the edge of my dress.

—You look beautiful —he said, unable to take his eyes off me—. If I hadn’t seen you as a man a little while ago, I wouldn’t recognize you.

—Do you really mean that, or are you just saying it so I won’t feel bad? —I insisted, still insecure.

—It’s the honest truth. You’re gorgeous. And your body—don’t even get me started. You’ve had my cock hard since you came out of the bathroom.

***

I sat on the edge of the bed, and he came over with a beer in his hand. I accepted it and, out of nerves, drank it far too quickly. We laughed. We had a couple more while we talked, and little by little the room filled with the kind of tension you feel on your skin before something happens. I crossed and uncrossed my legs, and every time I did, he followed the movement with his eyes, fixed on the edge of my dress as though breathing were difficult.

Suddenly I saw him lean toward me. He kissed me. It was a slow, deep kiss, so delicious that I couldn’t resist kissing him back, pressing my body against his. Our tongues searched for each other and twisted together, and he sucked mine as though he wanted to pull it out of me. His hands began roaming over me through the dress, moving slowly down to my legs, then traveling up the inside of my thigh until they brushed the garter. I didn’t remain still: I pulled off his shirt and ran my palms over his sculpted chest, moving down to the hard bulge stretching his pants. I squeezed it through the fabric and felt his cock throbbing against my hand. A moan escaped into his mouth.

—You’ve got such a big one —I whispered, my voice trembling with pure desire.

—All yours, gorgeous —he answered, biting my lip.

One of his hands was already under my dress, squeezing my ass, spreading my cheeks with his fingers, searching for my asshole through my thong. When he found the fabric, he pushed it aside and ran his fingertip right over my hole. I jerked. No one had ever touched me there that way, with such possessiveness, and I felt my legs opening by themselves. The intensity rose with every second. Before I knew it, he had taken off my dress, leaving me standing trembling in the garter, thong, and heels.

—Turn around. Let me get a good look at you —he asked in a hoarse voice.

I obeyed. I turned slowly, my hands resting on my thighs, feeling his gaze burn my skin. He pawed at my ass with both hands, spreading my cheeks, and I felt the cool air hit me directly on my hole. Then he made me turn around again and buried his mouth against mine while I opened his pants. I pulled them down along with his briefs in one motion, and there it was—the first time I saw it: his cock sprang out hard and thick, its tip glistening and a prominent vein running down its shaft. I lost my breath.

He lay back on the bed without taking his eyes off me, his cock pointing toward the ceiling, and crooked a finger for me to come to him. I climbed onto the bed on all fours, burning with lust.

I began moving down his body with my mouth. I kissed his neck, bit his collarbone, ran my tongue over his chest, and sucked one of his nipples until I heard him moan. I continued down his flat stomach, along that fine trail of hair leading to his pubic bone, and when I was in front of his cock, I paused for a second to look at it. It was the first time I’d had one so close. I grabbed the base and gave him a long lick from his balls to the tip. He let out a moan that made me even hotter.

I put it in my mouth as far as I could. I closed my lips around the shaft and began moving slowly up and down, learning to suck cock in the moment, letting saliva run from the corner of my mouth. I ran my tongue over the tip, wrapped my mouth all the way around it, pulled it out to lick his balls, and put it back in until I gagged. I looked up at him through watery eyes, enjoying the way he held my wig without tugging it, guiding my rhythm. His cock swelled in my mouth, growing harder every second, and I felt mine wetting the inside of my thong. I sucked him eagerly, swallowing my saliva and his, moaning with my mouth full, until he pulled me away.

—Stop, gorgeous, you’re going to make me come like that —he said, breathing hard—. And not yet. I want to enjoy all of you.

He handed me a condom, and I put it on him myself, slowly sliding it over that hard cock that was soon going to split me in two. Then he made me turn onto my stomach, lifted my hips so I was on all fours, and pulled my thong down with a slowness that drove me crazy. I felt his hands spread my ass cheeks wide, exposing my asshole to the air, and then his hot, wet tongue passing right over my still-virgin opening. A long, high-pitched moan escaped me before I could stop it. He pushed his tongue into my hole, pulled it out, licked me from top to bottom, slipped the tip inside, and twisted it around. My face was buried in the pillow, biting the fabric, my own cock dripping between my legs from sheer pleasure.

—Please, put it in me now —I begged, trembling—. I can’t take it anymore. I want to feel it inside.

—Are you sure, gorgeous? It’s going to hurt —he whispered against my ass.

—Put it in anyway. I want to be yours.

He settled behind me, grabbed my waist with one hand, and guided his cock with the other until the tip rested right against my asshole. He pushed slowly, and I felt the head begin to open me. It hurt. It hurt terribly, because he was far from small, and my body was clenching instinctively. I bit my lip and took a deep breath, forcing myself to relax, letting that huge intruder claim me inch by inch. He entered gradually, pulling out and pushing back in a little farther each time, until I felt his balls bump against my skin. He was completely inside me.

He stayed still, breathing against the nape of my neck, giving me time. He kissed my shoulders and my back, whispering that I was beautiful and that I felt incredibly tight. When the pain began to ease, he started a gentle, patient rocking motion, moving in and out calmly. Little by little I asked him to go harder. He began fucking me with more rhythm, gripping my hips, and I was moaning nonstop, pushing my ass backward to take all of him. His cock stretched me from the inside, filling me in a way I hadn’t known was possible, and every thrust tore another moan from me.

—That’s it, love, just like that, don’t stop —I begged with my face against the pillow—. Fuck me, I’m yours.

—You’ve got such a delicious ass, gorgeous. You’re squeezing my whole cock.

He drove it all the way in and pulled almost completely out, and I felt my own cock—which he hadn’t even touched—dripping come onto the sheet from the sheer pleasure of being fucked in the ass. He grabbed my wig with one hand, pulling my head back, and gave me several harder, deeper thrusts until I felt him tense.

—I’m coming, I’m coming —he panted.

He pulled out of me and lay on his back, breathless, the condom filled with cum. I removed it with my mouth, looking into his eyes, and licked what had leaked over the edge. Still sore, my asshole open and throbbing, I curled up against his chest. Only a moment passed before I kissed him again, telling him in his ear how much I’d liked it, how good I felt with him, how he’d broken me open inside. While I kissed him, I lowered my hand and began stroking his cock again. I felt it harden immediately beneath my fingers, throbbing hot in my palm.

—Do you have another condom? —I asked, unable to hide my desire anymore.

—No, that was the only one —he said.

Lust won out over prudence. I spit into my hand and rubbed his cock with my own saliva, wetting it thoroughly. Then I climbed on top of him astride, with my knees on either side of his hips, and took his cock in my hand. I pressed it against my asshole, still dilated from the first fuck, and began lowering myself onto it, feeling that this time it entered more easily, sliding inside bare, skin against skin. When I had taken all of him, I stayed still for a moment, feeling him pulse inside me, much hotter without the rubber between us.

I began moving at my own pace, in charge of my own pleasure for the first time. I raised my hips and lowered them again, impaling myself, bracing my hands on his chest to gain momentum. I looked into his eyes while I fucked myself on him, my wig falling over my face, moaning every time his cock reached deep inside me. He squeezed my fake breasts through the bra, then ripped the bra off to caress my hard nipples, raised his hands to my neck, and squeezed it lightly, as if marking me as his.

—Ride me, gorgeous. Just like that, don’t stop.

—I love your cock, love. I love how it feels without anything between us.

I picked up the pace. I bounced on him, my ass smacking against his thighs, listening to the sound of flesh hitting flesh. My own cock sprang hard against my stomach with every movement, dripping pre-cum onto him. I felt him breathing harder beneath me, tensing as he gripped my waist to drive himself deeper.

—I’m going to come inside you, gorgeous. I’m coming…

—Yes, my love, give me all your milk, fill me —I begged, moving faster.

I rode him until I felt him come again, and this time he filled me from the inside. I felt the hot spurts emptying into my ass, one after another, and the sensation made me come too, spilling over his stomach without even touching my cock. I stayed like that for a few seconds, impaled on him, feeling him pulse inside me as he finished unloading. Then I slowly pulled him out and bent over his semen-covered cock. I cleaned it with my mouth, licking from his balls to the tip, swallowing what remained without taking my eyes off him. I sucked the tip until the last drop was gone.

***

We stayed wrapped in each other’s arms a while longer, kissing unhurriedly, his semen trickling down my ass, until reality reminded us that we had to leave. We dressed in silence, stealing glances at each other, and went out. I dropped him off at the same place where I’d picked him up. It was already getting dark, and without caring who might see us, we said goodbye with a long kiss I still remember.

I hope I haven’t bored you with this little story. For me, it was the night I stopped hiding and finally became myself, whole and without masks. Very soon I’ll tell you about the next time I saw my love, and also another, even more intense story: that of the married truck driver whose secret woman I was for quite some time. But that, my dears, will be another time.