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Night Trawling: The Crossdresser
By
Milik_the_Red

Night Trawling: The Crossdresser

Sometimes the streets offer the most delicious surprises.

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. 

During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the streets around them. 

It’s a vibrant town, filled with the chaos and bedlam of regular life, but that is only half of its twin personalities. Once the sun drops away, the quaint nostalgia of those decades-old storefronts become as desolate as they are foreboding.

In that shadowed darkness, an eerie quiescence settles. Like malevolent spirits, the gangs emerge from their dens, plying drugs and sex to anyone brave or foolish enough to roam their turf after the kiddies go to bed. 

From Philadelphia Avenue to Mission Street and on through the infamous Holt Boulevard, an underworld hierarchy of criminals and deviants control the night. On the bottom rung of that insidious ladder are those unfortunate souls who sell themselves for nothing more than a few scraps of cash. It’s when those girls walk the streets that men like me go hunting for cheap and willing ass. 

I'd been cruising for an hour or so that night, driving those streets in a lazy 'Z', heading west along Philadelphia, only to move north and reverse my course down Mission. Then, up to Holt — and back to where I started. Some nights, it was easy to find a whore who fits my taste. Ten minutes on the strip to pick her up and then off to the seclusion of a quiet side street or an empty industrial park.

For a few bucks, I could relax in the seat of my car while some anonymous slut filled her mouth with my cock until I fed her my hot cream. If I wanted something different, I could bend her over the hood and fuck from behind. I enjoyed that. Taking a whore in the open was risky, but that could turn an often boring and impersonal fuck into something much more intense. 

A rented room for an hour in a seedy, roadside motel was the way to go when I really wanted to get my freak on. Most girls would give it all up for an extra hundred. Fucking a hooker in the ass, knowing she’d feel that burn for the rest of the night, left me feeling high. 

Part of the rush when hunting was that I never knew what kind of girl I might find. I had a few regulars, but they usually got picked up so quickly I may not see them at all. I can't imagine how many guys they fucked every night, but none of those girls spent much time actually having to hook. There were enough guys prowling for quick sex to keep them busy. 

That's why I was so shocked to see Toni that night. I'd never seen her before, but her slight build, lacy black dress, and easy stride, just screamed of youth. She looked like a tasty sheep, ready to be devoured by the wolves who roamed the night. 

I'd seen her as I passed in the other direction. She looked positively mouth-watering and I turned left at the next street. A quick U-turn brought me to a conspicuous stop about twenty yards in front of her. Sitting at the corner of a minor side street off Holt, I waited anxiously as she walked toward my car. 

This was the moment I loved. Making a deal for sex right out in the open was so obvious, but no one even slowed. In this town at night, hookers and their Johns were part of the background, and being invisible to all but my tasty little treat, made my cock twitch and swell. 

Damn, she was fucking sexy. Every step she took brought her closer to my lair. She'd seen me, of course, sitting in my car and smoking. Knowing what I wanted, she slowed her approach, wearily coming within earshot of my open window. I couldn't believe this tender young thing hadn't been scooped up, but as she passed under the amber glow of the corner light, I understood. 

"I'm not a girl, okay? I'm a boy, but I'll do anything you want." The voice was a distinctly young, male soprano. 

Fuck me! All that sexy, feminine style and she was a dude? I chuckled as she stopped just out of reach of my door. Clearly, she expected me to bolt, but when I simply crooked my finger at her, she walked up and leaned through my open window. 

"If you have a place and like it in the ass, I'll take you." My gaze burned as brightly as the cherry on my smoke and she swallowed nervously before nodding.

"Yeah, for a hundred and fifty I'll do it all. A hundred and fifty, okay?” 

Up close, I saw she was an effeminate Latino with delicate features and a flawless complexion. Her flat chest was distinctly male and I assessed she was more a crossdresser than someone transitioning. Dark eyes shined with an excited fear and hands trembled oh-so-slightly as they rested on my door. 

She was maybe seventeen years old. 

This kid hadn't been hooking for long, I was sure of that. No doubt she'd announced early that she was a boy to avoid being violently abused if I discovered that fact too late. That need to pre-warn me spoke volumes of her inexperience. Her innocence made her all the more desirable, and I guessed this could even be her very first trick. 

Hell, she's probably doing this as much to live out a fantasy as she is for the money.

As timid as she was, I figured this was her way to be used, fucked like a real woman, and that meant finding a man who’d take her without concern of her physical nature. It was a delicious thought, and I resolved to give her exactly what she craved. 

"A hundred and fifty? Shit. You're no whore. I think you're just out here to get fucked. I ought to make you pay me." 

Christ, the way her eyes dropped, was priceless. She looked like a kicked puppy, but she didn't snap back or stomp off in anger. This self-described 'boy' was as submissive as a kitten, and my cock throbbed as I realized how lucky I was to find her. 

"Come on, man. Don't be like that. I'll make it good for you, you'll see." 

Goddamn, I bet I can make her beg! The thought was intoxicating, but my cock was already itching to get into her ass and I grimaced, forgoing my need to make her squirm. 

Flicking my cigarette butt out of the window, I popped the lock on the door. "Fine. One-fifty, but we do this my way. Get in, and tell me where we're going." In a flash, we were heading west toward the Tiki Motel. 

These cheap-ass motels were shit holes but they did have their own, peculiar charm. Though the furniture was often beat up and the carpet worn, the beds were soft enough to be comfortable. I enjoyed how the colored neon glowing through the drapes silhouetted passers-by as I savored the illicit fruits of my hunt. These rooms were distinctly cookie-cutter in appearance, the perfect backdrop for the impersonal brand of sex I enjoyed most. 

Guiding Toni with a hand on her back, I smiled inwardly at the attendant’s knowing look. 

That’s right, motherfucker, she's a got a cock, and I’m gonna fuck her tight little ass until she screams.

Door closed, I paused long enough to consider how I might best use my new toy. I've found that handing money to a whore has a way of empowering her. It's strange really because taking my money should make her an employee, but in the sex trade, dominance is not so easily bought. Not yet wanting to grant Toni that bit of control, I tossed cash onto the bed. 

"Count it and put it away," I said as I headed toward the bathroom. "I don't want to hear another word about paying you. Understand?” 

It might seem I was being cruel, but I had nothing against the kid. She was obviously submissive, and I wanted to keep her off balance until she could earn my kindness. I was in it for the sex, but as I said, I was certain she was living her fantasy as well. 

It was a dangerous fantasy, considering the testosterone-powered violence afflicting these streets. I was aware enough of that to make this as memorable for her as I could. When I returned, she was sitting on the bed, nervously tapping a heeled toe. 

Holding out a hand, I indicated she should stand. "You're still here. I'm impressed." 

Head slightly tilted, eyebrows crinkled in confusion, she said, "Ah, what? Why would I leave?"

This kid just doesn’t get it. Flashing a predatory smile, I ran my fingers over the black satin of her dress. 

"You had the money. I was in the bathroom for a good five minutes, but you waited. Don't you see what that means?" 

Toni looked as if running had never occurred to her and I'm sure it hadn't. When she didn't answer, I cupped her cheeks in my hands and kissed her, sucking her bottom lip into my mouth. 

"It means you want this. You want to give yourself to me, don't you? It's okay, you can tell me. I think you’re beautiful. I'm not going to look down on you for being who you are.” 

A tremble passed through her and she sighed heavily, her nerves fading. "You don't think I'm some kind of freak? I mean, being gay is one thing, but the way I'm dressed?" Raising her hands, she looked down at her clothing, as if she were seeing herself for the first time. I recognized self-doubt, and my heart went out to her. 

To a more enlightened person, the need to crossdress isn't an unusual nuance of sexuality, but in these gang-controlled streets, where hetero-machismo means respect, it must have been terribly difficult for someone with her desires. I thought she was incredibly brave, daring to step out and live her life the way she was born to live it. 

Kissing her again, I felt her respond with passion. Slipping my arms around her waist, I pulled her against me, holding her tight until she melted into my chest. 

"Tell me, do you identify as a woman all the time, or is it the dressing up that really turns you on?" 

"This is kind of new to me," she quietly admitted. "I mean, I'm gay and all, but I usually live like a guy. Thing is, whenever I think of wearing something like this, it just makes me feel so different. I don't know… like I'm beautiful or something." 

She was adorable. The more I learned about her, the more fascinated and sympathetic I became. Who would have thought, in these streets filled with cheap and meaningless sex, that I'd actually connect with someone? That connection made this night one for the ages. 

"I love your dress,” I said. "You look sexy, just like a girl. Would you mind leaving it on for now? I promise not to ruin it." 

Toni nodded, clearly unsure of where I was going. But as I knelt, running my fingers down the gossamer fabric, her breath caught and she rested her hands on my shoulders. 

"Are you hard?" I asked, caressing her thighs.

"Yeah, I'm really hard. I didn't think I'd get anyone to suck my cock tonight."

"Really? Because you're being paid? You've never turned a trick, have you?”

Toni shook her head.

“Don’t worry. I think you’ll find that most guys you service love sucking cock. I'm glad I get to be your first." Gathering her skirt as I spoke, I smiled in satisfaction when I discovered an impressive bulge rising within her panties. 

Sliding a hand up her inner thigh, I urged her legs apart and traced my fingers over her panty-covered cock. I felt it twitch and I flicked a fingertip over the head. Her knees trembled. 

"My-oh-my, Toni. What a nice cock you have." 

A hot blush spread across her face, a shy smile on her lips. It was an adorable reaction and I locked eyes with her as I drew her satin panties down her thighs. Toni leaned back, bracing herself on the bed, and I lowered them below her knees — and off.

“Hmm, lovely,” I murmured, running the satin between my fingers. “I bet these feel amazing on your cock.”

“Yeah, they do,” she hissed as I rubbed the panties over her rampant erection. For several moments, I caressed the smooth material over her head and I knew it would create a burning heat. Toni breathed deeply and fixated her gaze on me when I stopped and put her panties in my pocket. 

With the dress again concealing her cock, I sought it through the cloth, and wrapped the material around her shaft. 

"Oh, fuck," Toni sighed as my grip tightened, stroking and scraping the lace over her skin. I had a feeling she'd love being masturbated through her skirt and I stroked her cock until she was biting her bottom lip. 

"Better not pop," I warned. "You'll never get all that cum out of this taffeta.”

Toni swallowed hard, clearly torn between a desire to preserve the dress and a growing need to come. By then, I was sure the material was being moistened by pearls of pre-cum, and I tried to judge just how far I could take her before she lost it. When Toni’s knees began to quake, I lifted the skirt and put the fat, purple head in my mouth. 

"Mmm, yeah, that feels so fuckin good." Toni leaned over me, hands on my shoulders, pumping smoothly and gently into my mouth. I allowed her to set the pace, fucking my mouth to her heart’s content. 

She was wonderfully hard and the taste of pre-cum soon filled my senses. Her cock was pleasantly large, but not so much as to be difficult to take in my mouth. When her thrusts became more urgent, I opened my throat and took the cock in deep. As the head passed into my constricting embrace, I dug my fingers into her ass and pulled, driving that wonderful piece of meat all the way down. 

Toni gasped, her fingers tightening on my shoulders. Holding me steady, she kept her cock lodged in my throat for what seemed an eternity as I squeezed her ass. When my eyes began to water and my cheeks filled with heat, I finally pulled back, and her slick cock slid out of my mouth. 

Fisting it, I stroked her quickly, coating my fingers in the thick wads of saliva dripping from her head. I saw strained pleasure glowing in her eyes, and I knew she would soon cum. 

I was waiting for that moment. 

Diving down, I inhaled the entire length, right down to the root. As her head plunged into my throat, I sneaked a hand back to her ass and pressed my middle finger deep into her hole. She was very tight, so I was all the more pleased to find she had already lubed her clenching hole. My long, middle finger pumped in and out, massaging her until she stiffened. A deep, guttural moan passed through her lips, and fingers dug into my shoulders as her orgasm burst through her. 

Her cock grew even harder, pulsing wildly as cum flooded my mouth. With my finger fucking her ass and her head barely between my lips, I stroked fast, bringing a thick load to pool in a slimy mass on my tongue. Pulse after pulse, her jism shot into me, filling my mouth until she had no more. By the time I pushed her back onto the bed, Toni was covered in a glistening sheen of sweat. 

Breathing hard, weak from her orgasm, Toni didn't resist as I flipped her over. Pushing the dress up her back, I exposed her wonderfully firm ass. I’d been kind so far, forgoing my urge to dominate her until she’d probably forgotten my intent. Now, she was about to discover the storm after the calm. 

With my mouth still full of her juice. I dug my fingers roughly into her cheeks, spreading them wide enough to completely expose her winking hole. Bringing my lips to it, I dribbled her slippery mess onto her rose. 

"Fuck, that's nasty," she murmured. But, even as she spoke, her hips rose toward my invading tongue and she spread her legs in lurid invitation. 

"Maybe it is," I grunted, unbuckling my jeans, "but I want you wet and slick when I fuck you. I'm gonna go balls deep into that tight ass of yours. I want you to feel my cock right up to your throat."

“Oh, my gosh," was all she managed as I licked her back entrance. 

I felt as much as heard her moan, and her ass responded to my tongue with a slight pucker before she relaxed. When her hole began to blossom, I poked in a finger, fucking her slowly until her rose surrendered to its inevitable violation. 

“Fuck, that feels good. Mmm, maybe next time I will pay you. You can do this to me anytime. No fuckin' charge." 

"I might take you up on that. My name is Jake, by the way. Now, you about ready, kid? I gotta tap this ass soon or I'm gonna lose it." 

"Yeah - and nice to meet you, Jake. Now, stop talking and fuck me." 

With a hard slap on her ass, I climbed on top, crushing the black taffeta skirt against her flesh. Leaning on her back, I pressed the underside of my cock into her cleft, sliding it up and back, coating my shaft in the mess I'd left there.

Toni ground against me, gyrating her hips as if she were starving for my cock. When she reached back and spread her buns, she was ready. With a wet bite at her neck, I brought my throbbing cock to her most intimate entrance. Toni writhed, squirming and flexing her legs, as I guided my engorged head to the center of her clenching ring. 

"Here it comes, babe." Growling, one hand fisting the base of my shaft and my other arm under her head to hold her in place, I forced my thick head into her. Toni winced as she felt the strain and her body tensed. Soon, with steady pressure, I felt her hole opening until my head thrust into its grip. 

Her walls were hot and slick, and Toni pushed back, crying out as the thickest part of my helmet squeezed through. Her resistance broken, I drove hard into her passage. Toni gasped, her mouth slack as several inches of my pulsating cock pushed deep inside. 

"Fuck, you are so damn tight,” I grunted, climbing higher on the bed and sinking my cock all the way in. My groin slapped against her ass and I pressed hard, grinding myself fully into her.

Toni was breathing hard, biting the sheets as I began fucking. Her fingers clutched at the bed, gripping it as my penetration burned her ass. With a hand on the back of her neck, I pinned her down and finally pumped her with the long, deep strokes I’d longed to give her. 

"That's it, Toni. This is what it feels like to be my bitch." With a loud grunt, I hammered her ass hard, driving my cock into her like a spike. 

Toni's body shook and she hissed in pleasure as I reamed her tender ass. Unable to move or even slightly resist, she surrendered to me, giving up her body to sate my lust. Her hole was so wet, so slick, that my shaft glided in and out, massaging her ring just as it sucked in my cock. I heard her whimper each time I pulled back and I savored her huffs when I plunged back in. 

"Ah, yeah, you're ass feels so fucking good. I'm gonna cum way up inside you, Toni. I'm gonna empty my balls and flood your ass with my cum. Does that turn you on, knowing you're getting it bareback?" 

Those words came in grunts because I was fucking her so hard. She was completely open by then and my long, deep strokes easily slid up and down. Toni was flat on the bed taking my weight as I thrust over her ass. 

"Oh, shit, do it. Come in my ass. Fuck, I’ve always wanted to know what the real thing feels like." Toni was lost in the act, pushing her ass back up at me, making my cock slam into her even harder. 

We were reaching the end and my desire to own her increased. I wrapped an arm under her throat and stabbed my cock into her as hard as I could. The bed creaked loudly as I pushed her slim body into it again and again. When I felt that glorious pressure in my balls, I lunged forward, driving my cock as deep as I could. 

"Ahh, fuuck. Here it comes,” I gasped into her ear as my orgasm built. “Take it all, right up your asshole.”

Hot cum boiled from my balls, spewing into her in thick ropes. I filled her hole, coating and lubing my shaft. By then, her ass was no tighter than a woman's cunt, and I fucked hard and fast until my heaving, burning chest was desperate for breath. Only then did I collapse onto her back. 

Keeping my cock buried in that hot hole, I grunted and pushed, making sure she got every last drop of cum. "Yeah, that's it, take it all, bitch. Mmm, I love ass-fucking you bareback. Now you've got me inside you forever."

Toni, having obediently received my juice until I was expended, fell limp. By the time I rolled off and lay next to her, my balls were drained. 

I'd like to say we had some kind of future or friendship, but that isn't how it works. After all, she was simply a paid fuck, and minutes after I climbed off her sweaty, exhausted body, I was just another pair of tail lights disappearing down Holt.

Authors Note:

I want to thank JWren for his editing talents. His efforts on my story were superb.

 

 

 

 

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