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Reveries of a Solitary Night Walker

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It's not the streets that are dangerous, it's the people you meet there.

Somehow, the streets never quite felt like his own until the night really set in. Most of the pubs in town were only just getting started at 9pm. Craig had always felt there was no point in going out to work until at least 11pm, when there was a decent chance of being picked up, and getting away with charging them a little more for the privilege.

He was still getting ready at 9pm. He was lucky that he was good enough to get most of his business done between 11pm and 5am, so he didn't have to work all night like some of the other sex workers in town. Andrew, his flatmate, had to work longer hours than he did, and as he didn't play up the drag like Craig did, he got fewer punters.

Not that Craig was in drag, necessarily. He'd run to Brisbane to escape his old life, because coming out as a woman had destroyed his marriage, lost him his job, and had left him with nothing. Even now, when he was more known as a woman than a man, he was still reluctant to transition properly. He knew full well what would happen to him if he was a proper transsexual prostitute, and while he hated his body for what it was, and wished he could change it, it would never happen until he had a much more safe and secure job that wouldn't put him in a vulnerable position every night with lonely drunken bastards who wanted to fuck a bloke, but only if he was dressed like a lady.

He sighed as he stared at his reflection in the mirror. He was half-made up. His body was waxed and shaved completely, leaving it smooth and as feminine as he was capable of achieving without a good rigorous dose of hormones. His dress was tight-fitting, but flattered all the right regions, including the small padded bra he was wearing. He wanted to look like a woman, not a drag queen, and big tits just didn't suit his frame. The wig was a long blonde number he'd picked up from a colleague who was getting out of the industry. It was old, and had seen better days, but it suited him perfectly. He'd taken good care of it, and had it reconditioned and repaired. His heels, well, they were magnificent, if hard to wear.

Craig, five years ago
Craig gasped as he was pushed against a wall, the breath knocked from him. He smiled as his lover kissed him, a hand sinking down underneath his dress. He shivered at the sensation of a hand curling around his cock, much as he hated it being there, and squeezed a leg around the man in front of him.

"So beautiful," came the murmur against his neck.

It almost made him cry, because he knew he wasn't, and he didn't want him lying. Instead, he let himself be distracted by his hands slipping his dress from his shoulders, caressing his skin.

Craig walked the streets into town, his heels clicking on the pavement. He was all dolled up now, and as he walked, he let himself get into character. He wasn't Craig when he was working. The name he'd chosen was Lucy, and she was altogether different. She still had Craig's sassiness, but she was more docile, more submissive. More demure.

She allowed herself to embrace her femininity in a way Craig never allowed himself to do, and her hips moved more naturally. She knew she was beautiful like this. She wore a short dress, this one a dark blue with gold trim, and chunky heels. Her hair trailed down her back, hanging loose. Her make-up was subtle and effective, hiding all trace of the male body underneath.

It was the packing and tucking that always took the longest. She did wish she didn't have to deal with that, that she could have surgery to make it female, but she earnt far more as a 'chick with a dick', as she was often called. She hated it. If she hadn't been so reliant on sex work to pay her way, if she hadn't trained her body to get her through the night, she'd be dead.

The suburban streets were the favourite part of the walk into town. They were well-lit, and quiet most of the time. Cars and buses might come by every now and then, but she had managed to secure a flat in a good neighbourhood, so she and Andrew had a nice place to live, with less chance of being robbed on the way to work. Less chance of being catcalled, too. She was never quite ready to deal with that until she started work, and the later that happened, the better. She had no time for dickheads.

Craig, four years ago
It wasn't like he had planned to get into sex work. It had started mostly in Melbourne, before life had become what it was. His work had taken him down there quite frequently, and as he'd explored the nightlife, and tried to find safe places to let the woman inside him come out, he'd sort of stumbled into selling sex for money.

Not that it had been for money at first. He'd found some entertainers, comedians, perhaps, who were quite willing to let him trail around with them when he could in exchange for sex. It wasn't exploitative, or it hadn't started that way. Craig had wanted a chance to be a woman, away from where people knew him, and trailing around with comedians had proved to be a good way to do that.

Adam kept him safe, though, no matter where they were. Adam, with his strong arms, and his ability to usher him safely away from danger when Craig's cover was almost blown, he was his rock. Adam knew him like no one else did. He never had to lie to him.

And when they slept together, hiding in the dark of a hotel room, there was peace.

She'd been working for an hour now, but she could tell it would be a hard night. Tuesdays were always hard. The crowds were just that little bit smaller, more the regular clients who were out every night, as opposed to the swell of people on Friday and Saturday nights. She'd given two blow jobs, and earnt herself $50. It wasn't a great night, and she only ever did them because it passed the time.

As she sat at the bar, watching the crowds, she hoped she'd find some punters interested in a fuck. She needed their earnings to make the night worthwhile. Her drink was more of a ploy, and it was easier to fuck with her dick if she had to when she was, if not drunk, then at least not sober.

As she caressed the top of the glass with her finger, she felt a hand brush across her ear. She turned to see a very familiar face before her.

"Well, well, well. You have been a while," she said, smiling coyly.

Adam smiled, pleased to see her. "Wil said you were working up here. I couldn't resist seeing you again. Can I buy you a drink?"

Craig, three years ago
He was the one man from her past that she allowed herself to acknowledge. She'd search for him in the bars if she knew he was in town, but never dared to approach him. He was more identifiable now than he had been when they'd danced the comedy circuit in Melbourne together. She didn't want to risk being seen with him, because people would talk.

It wasn't that she was worried for his reputation, but for her own. Where she worked, they never had top-end clients. They picked up whoever was willing to pay at a bar at two in the morning, and there were no top-end clients there. It wasn't always the best way to work, but she was fiercely against working for someone else, so it was what she was left with after a long and drawn out compromise with the rest of the pimps in town. She could charge what she liked, but there were certain pubs she couldn't go to, and certain people she couldn't court, unless she wanted to get her head smashed in.

She'd always been very persuasive, though, and the days she'd spent with Adam had taught her many valuable skills that had her earning the money she did. She could make it pay, and she needed to make it pay, because what didn't go into rent and food, went into an account to save for her transition when she felt she could safely leave town and go somewhere else to become who she really was.

She dreamed of that day. She dreamed of the day when she could be the woman she really felt she was, when she could stop selling her ugly body for money, and work a proper job again. When she could finally be happy in her own skin.

She was safe in his arms again, back at his hotel. He'd offered to pay her a night's earnings if it meant he could have the whole night with her, just to catch up. He wasn't sure when he'd be back in Brisbane, and didn't want to waste the time he did have.

He held her, fucked her, undressed her with his gentle hands. He kissed her like he had always done, moved inside her the way she remembered, and when he whispered to her, when he brushed her hair softly, and called her beautiful, this time, she believed it.

Craig, two years ago
"You're lucky you're not on the list," she purred as Wil gazed up at her. "I'm not meant to court touring comedians. Not officially, anyway."

Wil raised an eyebrow. "Oh? Don't I count as a comedian anymore?"

She moved up his body, her silky dress making him shiver. "Not up here, not for this. I don't know why. But at least I can be with someone I know. Strangers are tiring."

He kissed her, and the way she was grinding against him made him finish the job of removing their clothes. She didn't look quite so feminine anymore, but she knew Wil. He didn't touch her cock; he touched her like a woman, affirming who she really was.

She licked down his chest, and grasped his cock, eager to get started. She did love her work, at least some of the time. Wil bit his lip as he watched her go down on him. She was taking him into her mouth, all of him, doing things with her tongue she hadn't known the last time they'd slept together three years ago.

"D-don't be too quick. I'd - I still want to fuck you," Wil managed to say as she sucked hard on the head, her hands squeezing him tight.

She offered a half smile as she gazed up at him, knowing she had him where she wnated him. She would enjoy fucking him, but there was no point in rushing it. Wil always needed a little more prep work before it was worth diving into the sex. Her own cock was limp, but all she cared about was making sure Wil got a good fuck.

She did love the way his cock got hard, though. She could tell when it was time to fuck him based on how hard he was. There was a little tremor, a small pulse she knew imtimately, and she began prepping him, and herself.

She was on her back, gazing off at the wall as he fucked her, leaning over her in the darkness. Her body was his, not her own, and as long as he was happy, she was happy. He held her close, stroked her hair, whispered how beautiful she was, just like they all did. She heard the affection in his voice mixed with lust. She felt him relax, and held him close, willing him to say with her, just for a moment.