Dear Nude Town USA,
I stared at myself in the full-length mirror, hardly recognizing the reflection looking back. The blonde wig sat perfectly styled, framing what I’d always thought was too masculine a jawline—but tonight, with careful contouring and that deep red lipstick, I almost believed the lie. The paisley dress clung to my body, the fabric smooth against my shaved skin. Stockings ran up my legs, the delicate material making me shiver each time I moved, my small three inch penis neatly and easily tucked away in the pretty thong panties and four-inch heels forced my posture into something feminine, something vulnerable.
My heart hammered against my ribs. Three months of talking to him on the app. Three months of building up to this moment. He called himself BigDaddy47, and he knew exactly what I was—what I wanted to become. He’d seen my photos, the ones where I’d carefully tucked and posed, and he’d told me I was a good little sissy who needed to be used by a real man.
I grabbed my purse and walked out to my car, the heels clicking on the pavement of my driveway. The night air rushed up my dress, cool against my thighs. This was it. My first time out in public. My first time meeting a man who promised to treat me like the woman I desperately wanted to be.
The parking lot of the abandoned K-Mart was nearly empty, just a few scattered cars and one pickup truck idling near the back. I pulled in three spaces away and killed my headlights. My hands shook as I checked my phone.
*Behind the building. Don’t keep me waiting.*
I got out of my car, each step in these heels a deliberate act of balance and submission. The click-click-click of my steps echoed in the quiet night. I rounded the corner of the building and saw him standing near a rusted dumpster, his face illuminated by the distant streetlight.
He was stocky, thick-shouldered, with a barrel chest straining against his flannel shirt. Hair curled out from the collar, thick and dark. A beard covered most of his face, and his eyes tracked my approach with a predatory stillness that made my stomach drop.
“You’re smaller than I expected,” he said, his voice a low rumble. He didn’t smile. He didn’t move. He just watched me with those flat, assessing eyes.
“I—I tried my best,” I managed, my voice pitched higher than natural. I’d practiced for hours.
He snorted. “Get over here.”
I walked toward him, my heels unsteady on the cracked asphalt. The smell hit me first—sweat, cigarettes, something muskier underneath. He grabbed my arm when I was close enough, his grip hard enough to bruise.
“You’re really going through with this,” he said, not a question. His free hand reached up and grabbed my wig, yanking it slightly askew. “Pretty little thing. Too bad you’re just a faggot in a dress.”
The words burned through me. I should have been offended. Instead, my cock twitched beneath my tucked panties.
“On your knees,” he ordered, pushing me down. I stumbled, the heels making the descent awkward, and landed hard on the asphalt. Pain shot through my kneecaps, sharp and immediate. “That’s where you belong. That’s where all you sissy bitches belong.”
He released my arm and reached for his belt. The metal clinked as he undid it, the sound obscenely loud in the empty lot. His zipper came down next, and then he was pulling out the fattest cock I’d ever seen in person. Thick, veined, already half-hard and growing.
I parted my lips, and he didn’t wait. He shoved forward, the head of his cock pushing past my lips and slamming against the back of my throat. I gagged immediately, my eyes watering, but he held my head in place with both hands fisted in my wig.
“That’s it, choke on it,” he growled. He pulled back and thrust forward again, harder this time. My lipstick smeared along his shaft, the red leaving streaks on his skin. “Fucking queer bitch. You wanted this, didn’t you? Wanted to be treated like the slut you are.”
Tears ran down my cheeks, ruining my careful makeup. He fucked my face with brutal, selfish strokes, using my mouth like a toy. Each thrust made my jaw ache, made my throat spasm around his thickness. Drool spilled from the corners of my mouth, running down my chin and dripping onto the paisley fabric of my dress.
“Look at you,” he said, his voice thick with contempt and arousal. “Dressed up like a woman, on your knees in a parking lot, getting your face fucked by a stranger. You’re pathetic. A pathetic little sissy bitch.”
I couldn’t respond. Could barely breathe. His cock filled my mouth completely, cutting off air each time he pushed deep. My hands hung uselessly at my sides, my carefully painted fingernails catching the distant light.
He yanked my wig completely off, exposing my short-cropped hair underneath. The cool night air hit my scalp, a shocking contrast to the heat of his body. He threw the wig somewhere behind him, into the darkness near the dumpster.
“Don’t need that fucking thing,” he muttered. “I know what you are… barely a man, a faggot who dresses up and begs for cock.”
His thrusts grew faster, more erratic. His breathing came in harsh grunts, his belly pressing against my forehead with each forward motion. The wet, obscene sounds of my mouth around his cock filled the air—slick, slurping noises that made me feel even more degraded.
“Play with yourself,” he commanded. “Play with your little clitty through your dress. Show me how much you love being used.”
My hand moved without conscious thought, pressing against the front of my dress where my cock strained against the tucked panties. I rubbed myself through the layers of fabric, the friction making me moan around his cock. The vibration must have felt good because he groaned and fucked deeper.
“That’s it, you dirty whore. Get yourself wet while I use your mouth. That’s all you’re good for—taking cock and being a cum dumpster.”
My jaw ached. My knees screamed against the rough asphalt. My makeup was destroyed, my wig gone, my dignity scattered somewhere in the dark. And I’d never been more turned on in my life.
He pulled back enough that just the head of his cock rested on my tongue. I could taste the precum leaking from him, salty and bitter. His hand wrapped around his shaft, stroking fast.
“Look at me,” he ordered.
I raised my watery gaze to his face. His expression was twisted, almost angry, his teeth bared in a snarl of pleasure.
“Take it.”
The first spurt hit the back of my throat, hot and thick. I swallowed instinctively, but there was too much. Cum filled my mouth, coating my tongue and leaking from the corners of my lips. He groaned, a low animal sound, and pumped more into me. I swallowed again and again, my throat working around the bitter fluid.
When he finished, he pulled out immediately. His cock was already softening, glistening with my spit and his cum. He tucked himself back into his jeans without looking at me, zipped up, refastened his belt.
I stayed on my knees, cum on my chin, my dress ruined, my wig somewhere in the trash. The asphalt had torn holes in my stockings. My knees throbbed. My jaw ached.
He turned and walked to his truck. Didn’t say goodbye. Didn’t offer me a tissue or a hand up. Didn’t even look back.
The engine started, headlights flared, and then he was gone, taillights disappearing around the corner of the building.
I knelt there alone in the dark, beside a rusted dumpster, with the taste of a stranger’s cum still coating my mouth. A cum dumpster next to an actual dumpster. The thought made something twist in my chest—shame and satisfaction tangled together.
I reached for my wig in the darkness, my fingers finding the synthetic hair tangled against old newspapers and garbage. My reflection in my car window later would show a ruined thing—mascara running, lipstick smeared, hair a mess.
But I’d finally done it. I’d finally been used like the cock whore I wanted to be, used dressed as the woman I am deep down and I know this first time will not be the last time!
Sincerely,
Just a faggot in a dress…