A Lady in the Streets Ch. 04

"You're doing great, just a little more," said Keith. It was easy for him to say.

Anna took another deep breath, gathered her focus, then resumed her leg curls. She was sure her legs must have had more lactic acid than blood at this point, but this body wasn't going to maintain itself. Five. Six. Seven. Eight. Nine. Ten. She let her muscles relax and the ache shot through them again. She leaned over and grabbed her phone, the fingerprint unlocking it before it had reached her line of sight.

"A little distracted today, love?"

There were no notifications. She sighed.

"Oh um, yeah. Just waiting on an important message."

She stared at the time. It had been half an hour. Why isn't he responding to me?

"Do you need to step out for a minute?"

"No, it's fine," she said, then nervously giggled, although she felt like a concentrated ball of anxiety and dread. She almost didn't notice the physical aspects of her exhaustion for a moment.

She put her phone down again and stood up.

"Ok, time for the cool down darl," he said.

Keith was a total hottie, like a younger, ripped Keanu. He was from some middle-of-nowhere rural town originally, which was kind of charming in it's own way. He wasn't on the menu, though. Anna had long ago been informed by some of the regulars that he batted exclusively for the other team. That suited her just fine, and some of the women who came here felt safer around him because of it. Anna got into position and started moving her arms around to loosen up.

"Jogging on the spot," he said.

Her body went through the motions, but her mind was firmly fixed on something else.

"Ok, let's do some static stretching today."

The hamstring stretch felt particularly good, but she still kept stealing glances over to her phone. The seventh time she looked over, the notification LED was flashing. Anna stood up mid stretch and raced over to it.

"Sorry, I have to respond to this," she said. Keith just shrugged.

She unlocked the phone and opened the message.

"Ok," it read. She waited to see if he was typing a followup, but it didn't seem like he was.

Her heart sank. She'd told the Doctor that she was going to the gym, and she was hoping that he would like that. She couldn't remember a lot of her therapy, but she did know that external validation was very important to her, and keeping her body in top shape was a part of that. It made perfect sense once he'd pointed that out. So many of her behaviours were based around it and she'd never even really noticed. Sometimes it felt like the Doctor knew more about her than she did, but she supposed that was why he was paid the big-bucks. He was a true professional, and she really, really cared about what he thought of her. Sure, a lot of the guys at the gym gave her stares, but that wasn't the same. I wish he could see me here.

She resumed her cool down exercises, but an idea started forming in her head.

"I'm sorry, I'm going to have to cut this short today," she said.

"Ok," he said, scepticism coating his voice. "Just take care of yourself, alright? If there's anything I can do to help, just let me know."

"Thanks Keith," she said.

Anna grabbed her towel and phone and darted into the change rooms. She found a mirror, then unlocked the phone and opened the camera. She raised the towel to her forehead then stopped. Would he prefer it with the slight sheen? What if he likes women kinda sweaty? Oh god, but what if he hates it? She decided not to risk it and wiped herself down. She quickly found her favourite angle and snapped a photo, making sure to catch her gym clothes in the frame.

She opened up the chat window and hesitated. What the hell am I doing? He's my therapist! But then she was struck by another thought. He might be able to tell me if people would like this. If he would like this. She shuddered at the thought. She looked down at her phone and realised that she'd already sent it.

Doctor Nicholas J. Stewart has seen this.

She couldn't breathe.

Pop. The pleasure struck her -- hard.

"Oh fuck," she said aloud to nobody. Her knees were jelly and her jaw hung open and the feeling washed through her. Her eyes rolled back slightly.

The doctor hadn't just liked something. The doctor had liked her.

She sat and basked in the feeling. She looked at his reaction over and over again, each time feeling a smaller and smaller jolt of pleasure. Anna was unsure about a lot of things in her life. What she wanted to do, who she wanted to be with. But she was sure of one thing -- she needed more of that.

She opened up her photo gallery and scrolled through. There was no shortage to choose from. She hovered over one that she liked, but froze. I can't just send him pictures of myself with no context. Can I? She stood in silence. Get a hold of yourself girl! He's my therapist! She took some slow, deep breaths, then attempted to summoned the motivation to move. The trouble was, she didn't want to. Her thumb was still hovering over the screen when it suddenly dimmed. She scarcely noticed her thumb moving before it hit send again. Oh fuck oh fuck oh fuck...

Waiting for his reply was bringing back feelings she hadn't felt since the day her final exam results were being released.

Doctor Nicholas J. Stewart has seen this.

Her heart skipped a beat, but the feeling was quickly burred by anxiety again. She waited for a reaction or a reply. And waited. And waited. When five minutes had passed, she was ready to cry.

Oh my god what am I doing? Why did I even send the stupid ugly picture? Somebody opened the door to the change rooms. She stood up and tried to act cool. The stranger smiled at her, and she smiled back, then moved to the exit. She couldn't keep her breathing steady. She scampered down to her car, got inside, then opened her phone again.

Doctor Nicholas J. Stewart is typing a message.

"I preferred some of the others you posted online."

Her feelings couldn't settle on anything concrete. Which ones did he like? She wasn't bothered at all by the implication of what he'd just said. The most important thing in the world was to figure out what Doctor Stewart would like.

She looked through the photo reel again. She thought she looked great in the photo she'd just sent, but looking more closely now, she realised that she wasn't really showing off much of her body, just her face. She skimmed through to find something that might be a little more suitable. She found one of her beach pictures from last weekend that she remembered getting quite a few comments on. She froze at the last second -- should I try something that shows off my cleavage, or something that shows off more of my legs? She thought about it for a moment. Why not both? She noted that in the current image she was barefoot on the sand, and for some reason she felt like that was really adding to the composition.

She selected two images, one side profile taken with a timer and the other a high angle selfie. They were both bikini shots. In the first her toes were curled up at the bottom of the frame. There was no hesitation this time, not when she was so close to finding what he liked. She fired them off.

Pop. Pop.

It was rapture. Doctor Stewart liked both of the images. Doctor Stewart liked her that much. Her eyelids fluttered, her hips bucked and she couldn't stop herself from moaning -- loudly. It was the hardest she'd cum in weeks. When she finally came to her senses, she looked around and saw that someone was staring at her from the other side of the parking lot. Her face now a bright red, she put on her seatbelt, turned the ignition and left.

The next message she received wasn't a question. It was a command.

"I've got an opening this evening. Come and see me at the practice."

* * *

Doctor Stewart did not keep files on his clients. On the off-chance that somebody were to ever uncover what he was doing, the last thing he needed was a series of notes on his own criminal activities. While this helped him sleep easier at night, it also sometimes made it hard to keep track of things. That's what Grace was for.

"Yes Doctor," she mumbled as she rushed into the room. "What do you need?" Remembering what he expected of her when they were alone, she dropped to her knees and bowed her head. "I mean... how may I serve you, Doctor?"

Doctor Stewart reached out and ran his hand along her face, then slipped one finger into her mouth. She sucked on it as he thought about his upcoming appointments.

"Is she still out there?"

"Yes Doctor," she said as best she could under the circumstances. He pulled his finger out. "Would you like me to send her in?"

Doctor Stewart leaned back and Grace reverted to her submissive pose.

"No. Not yet I think. It'll be good for her to be kept waiting. Now, remind me Grace, what was the phrase for Ms Barkley again?"

"That was the Roy Orbison, Doctor."

Doctor Stewart didn't say anything. He rarely needed to with Grace. He simply looked at her with disapproval in his eyes.

"From Pretty Woman" she said, slightly panicked.

"Ah yes! That was it." His expression softened, and relief visibly overcame her. "I'll be needing to make another deposit," he continued, and started dialling her number.

Grace crawled forward on the carpet and traced her hand gently up his leg. She looked up into his eyes, pleading, and gently brushed her fingers over him. Doctor Stewart waved her off and mouthed "Not now" silently.

Not wanting to disappoint, but still wanting to serve, she approached from the other side and started massaging his neck and shoulders. Doctor Stewart let out some sounds of approval as the phone connected.

"Hello?" said the silky feminine voice on the other end. There was a lot of ambient noise coming through -- music, glasses tapping, people stepping.

"Ms Barkley, this is Doctor Stewart calling," he said, raising his voice instinctively.

"Oh! Lovely to hear from you Doctor, what can I help you with?"

"It's slightly personal, I'm afraid. Are you alone right now?"

"Hang on, let me just duck into one of the back rooms for a minute," she said. Thank goodness, he thought.

Doctor Stewart sat up straight and tweaked his neck slightly to give Grace better access. It felt wonderful, although it had taken a while to get her to this point. Her hands weren't very strong, but she was eager to avoid disappointing him.

"Ok, I'm alone now," said Ms Barkley.

"I was hoping you could give your smile to me," he said.

Ms Barkley inhaled sharply as the trigger did it's work.

"Oh my love, it's been far too long," she said. Doctor Stewart winced. He didn't have a lot of regrets, but this came close. Wrangling her could be a right royal pain sometimes. "I just can't stand it! I need to see you again!"

"Soon, my dear, very soon. I hate to ask, but I was wondering if you could take care of some more money for me. Do you remember the arrangement?"

"Yes, of course! It's no trouble at all. But um..."

"Yes, what is it my sweet?"

"Oh I just... wouldn't it be wonderful if we could spend some time together first?"

The Doctor's shoulders knotted up. Grace, who could hear all of this, redoubled her efforts.

"Of course, of course we can. It's just that I'm so busy these days, and you know we can't be seen together..."

The line went silent.

"I understand," she said shakily. Soon after, he could hear her gently sobbing.

The doctor covered the microphone to sigh.

"Look, I think we could fit something in. How about a nice dinner?"

Ms Barkley almost squealed with delight.

"Ohhh yes Doctor! Oh that would be so wonderful."

"How about tonight," he said, looking at his watch. "8pm at mine? You could pick up the money while you're over?"

"Yes, yes! Oh my love I simply can't wait!"

"Nor I, precious. I'll see you then."

He hung up and turned to Grace.

"Remind me that I need to fix her at some point."

"Yes Doctor!"

Doctor Stewart couldn't very well walk around with duffle bags of cash that his girls had brought in. At some point, the majority of that money needed to be converted into a useful format. Several imaginary clients took care of a portion of that, but that too would look suspicious in too high of a volume. For that, there were "investments" that were made in more legitimate businesses.

Doctor Stewart considered himself to be an expert in matters of mind, but not in finances. When Grace had proposed investing into a strip club, he'd been sceptical. But the owner, one Ms Barkley, proved to be amenable to a partnership. Too amenable, in some ways. But the results, he couldn't deny -- and high cash flow businesses like that were the perfect way to legitimise that money, even if it meant the tax-man taking a cut.

For now, he had somebody else on his mind.

"Fetch her for me, would you?"

"Yes Doctor! At once!"

Grace scurried out the room, and Doctor Stewart kicked back and waited.

* * *

When Anna arrived at quarter to five, she had no idea what to expect. The Doctor had told her to come around, but when? "This evening" could have meant anything, and she dared not ask. After all, what if he didn't like that? And thus, in the corner she sat, stewing with doubts.

At least I look nice, she thought. She had an idea of what the Doctor might like her to wear based on her photos. She couldn't quite walk in here with a Bikini, but she could wear the next best thing, which was a skimpy ensemble involving a short black tank top and a fairly short red skirt. A lot of her skin was showing, and it left her midriff completely exposed. It was a part of her body she worked hard to keep looking this good, and she'd be damned if she didn't get the chance to show it off every now and again.

At five thirty, the receptionist, Grace, smiled over at her. Anna stood up, ready to go straight in, but then she apologised and said that the Doctor wasn't ready for her yet. Anna waited as patiently as she could. Her brain performed dozens of trial runs of how she might walk into the office and greet the doctor.

A hair after six, Grace stood up and walked into his office. For the next five minutes, Anna stared at the office door, praying for any sign of movement. Her prayers were eventually answered.

"Doctor Stewart will see you now," said the young woman.

"Thank you," said Anna, trembling slightly.

Doctor Stewart was waiting in a very relaxed position in his chair, a sight that Anna was starting to become very accustomed to. The casual arrogance in the way he seemed to hold himself was now something she found herself liking. He had such confidence. She smiled brilliantly as she walked through the door, and when he returned it she found herself giggling once again. God get a grip!

"Good evening Anna," he said.

"Good evening Doctor," she said.

Ok, I can do this, she thought. In a manoeuvre she had practised in her head at least five times, she turned away from him, closed the door, kicked off her shoes, then bent over very slowly to pick them up and place them neatly against the door-frame. She made sure to take her time and give him a good angle. She felt so stupid, like she was trying to seduce him or something, but it wasn't like that. It wasn't like that at all -- it's just that she thought that he might like it.

"Ah, saving some time taking them off now -- I like that."

She stopped and shivered with pleasure. She couldn't turn to face him or he might notice, which would be super-weird. How could she even explain that if he asked?

"Mmm yeah," she said a moment later. "I figure I'll end up on the couch eventually."

"Definitely," said Doctor Stewart, smirking. It took her half a second to realise the unintentional double-entendre in what she'd said. She blushed and let out a short, nervous giggle.

"You know, Anna, we've only been having these sessions for a short while now, but I really think we're making a lot of progress."

"I'm glad you think so. But um, I'm not really sure what we're progressing towards," she said. "I definitely enjoy these sessions, though."

"Well perhaps that's good enough," he said. "But you know, this is a mutual journey. We're both along for the ride here."

"Um, yeah! Totally."

"And I really like that you're enjoying yourself, but I'd like to enjoy myself too."

She barely noticed what he said after "I really like that". She clenched her jaw and hoped she wasn't being too obvious. God, what if he asks me why I keep squirming?

"Shall we start by talking about what happened today?"

"Um, what do you mean?"

But she did know what he meant. Why the hell did I send those pictures to him? Am I really that desperate?

"Well, I mean these photos you sent me," he continued. She shifted in her seat and averted her eyes. "And don't get me wrong, I liked them a lot."

Oh god. Oh Christ. She involuntarily moaned, but thankfully the Doctor didn't seem to notice.

"You're showing me almost as much right now."

"Doctor..."

"Don't interrupt, I'm not finished. I think it's very important for us to get to the bottom of your issues. And I know what you're going to say -- you don't think you have any. But I think somebody who decides to send their doctor borderline-lewd photographs and wear... that into your sessions is probably somebody who has a few deep seated problems. Problems you don't even know about."

Anna felt absolutely humiliated.

"You make it sound really bad when you put it like that," said Anna. "It's just... you know... you liked it."

"Yes Anna, it's honestly very flattering that you value my opinion so much. But have you ever stopped to think why that is?"

She shook her head.

"Hmm. Well I think we'll have to get to the bottom of that later. But as I said -- I'd like to enjoy myself too. And you know I have your best interests at heart, don't you Anna?"

"Yes Doctor, of course," she said, smiling again suddenly. "Doctor Stewart always has my best interests at heart."

"I think -- and correct me if I'm wrong -- but I think that you'd like to show me more than you already have. A lot more."

Anna's jaw dropped.

"Excuse me?"

"I know that sounds crazy, but if I liked what you showed me, and I liked you, then wouldn't it stand to reason that I'd like to see more? And therefore, that you'd like to show more? You see, by doing things I like, you're really doing things you like."

Anna could't believe what she was hearing, but at the same time, she couldn't find a fault in his logic. And the more she thought about it, the more correct she realised he was. The Doctor would like it a lot if she just showed off some more of herself. And would it really be so bad?

"I... yes..."

Doctor Stewart simply looked at her and smiled.

Anna inhaled sharply and stood up. She knew what she had to do. She reached up to her tank top and slowly, sensually lifted it away. She thanked her lucky stars that she'd decided to wear one of her nice bras today. She looked over at him expectantly.

"Mmm yes, I do like that, Anna."

Yeeessss. The pleasure washed over her once again.

"Don't stop now," he continued.

Anna dropped her skirt to the ground, then slowly pivoted to give him a good, long look at her tight young body. She saw the look on his face, and he didn't even have to say anything. She knew he liked that. She felt even more pleasure.