A Lady in the Streets
Chapter 4
by Alan Smithee
“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.
“Christ,” he said. “You really are a work of art, Anna.”
That might make her blush under normal circumstances, but her face was already so red. She was starting to feel close, and didn’t think she could speak coherently right now even if she wanted to.
Anna had never actually been to a strip club, but she’d seen them in movies and on TV. She had a general idea of what kind of moves the women did. At least, she thought she did. She turned away from him and unclasped her bra, catching it before it fell to the ground. She turned, bra still held up by her hands, drew close and started moving her hips rhythmically around. She really hoped he liked that.
“Mmm…”
She felt a slight pleasure, but she needed more. So much more.
Anna dropped the bra to the ground, and Doctor Stewart’s eyes went wide.
Pleasure.
Anna came closer, and Doctor Stewart moved the chair back to give her room to stand directly in front of him.
“Oh yeah…”
Pleasure.
Anna slowly stripped off her panties, then turned and gave him another quick show.
The Doctor was strictly professional the whole time. He didn’t wolf whistle, he didn’t make any crude comments, and he didn’t try to touch her. Anna was so grateful that she had such a gentleman for a therapist. So many people might try to take advantage in a situation like that – one that could so easily be misconstrued.
“Anna, I’m so proud of you,” he said. “And I just want you to know that I really, really liked that.”
She dropped to her knees and gaped. Her body shook. Her head arched back.
“Ohhhhhh fuuuuck…”
It took another minute before anybody said anything. Anna had fallen to the floor as the afterglow took hold.
“Anna… there’s… well there’s one thing I’d like you to do as well.”
Despite having just come, Anna was eager to hear what it was.
“And I want to remind you, that this is strictly for your benefit. While I do take pleasure in this, I hope you understand this is part of your therapy.”
“Mmm…. Yes Doctor…” she mumbled, still a pile jelly on the floor.
Doctor Stewart leaned down and helped her up onto her knees again. It was a bit of a struggle but she got there.
“I really just… I don’t want you to think I’m being untoward, you understand.”
Anna giggled.
“Really Doctor, I don’t know what you’re so worried about. I know that Doctor Stewart always has my best interests at heart.”
He still looked so concerned. Anna wondered what she could do to put his mind at ease.
“You’re positive that you won’t mind?”
“Absolutely, Doctor. Name it.”
He glanced around the room nervously.
“Well ok…”
Doctor Stewart unzipped his pants, and his cock sprang out.
“Oh my,” said Anna. It was the last thing she’d expected to see.
“I’m terribly sorry, dear, it’s just that… well you do know that I really liked what you were just doing. I’m afraid I am only human, after all.”
“Oh Doctor…” she said.
Anna stared at the throbbing penis. It was obvious in retrospect, really. Doctor Stewart liked what she was showing him, which meant that he was obviously attracted to women. If somebody you were attracted to was doing what she was just doing, then of course you’d get sexually aroused. If he really liked her that much, then that would mean he’d probably like it a lot if...
“I’m sorry, this is inappropriate…” he said, and moved his hand down to tuck it back into his pants.
“Oh no- no don’t do that,” she said, and reached a hand out to stop him.
She’d made up her mind.
“Are you sure it’s ok, Anna?”
“Absolutely.” She smiled, and his hands returned to a relaxed position.
She grabbed his cock and started slowly stroking him.
“Like this?”
“Oh yes,” he said. “Yes that’s a great start.”
Anna felt another little jolt of pleasure, knowing full well that he was feeling the same.
As she continued to pleasure Doctor Stewart – and therefore herself – she was struck by another thought. She leaned forward, her muscles now feeling a little bit more stable, and licked his shaft from the base to the tip in one slow movement.
“Oh fuck, Anna,” he said, and with that she felt another shot of pleasure pass through her.
It quickly turned into a full on blowjob. Anna actually kind of liked giving head, provided the recipient was clean. Although if they always felt so good to give, she probably wouldn’t have cared even if they weren’t.
She took him fully inside her mouth, and he gasped once again. She bobbed up and down, occasionally taking a break and letting her hand take over. With every sound of pleasure he made, Anna felt that returned straight back to her.
“Oh Anna, you have no idea how much I’m enjoying this,” he said.
Pleasure. So much pleasure.
“I’m so glad you understand,” he said, starting to buck and gyrate himself. As her head moved up and down, he started to slightly push in and out, matching her movements.
She could tell that he was close. He started moaning louder and louder, and his movements became less disciplined, more frantic.
She had him deep in her mouth when she felt the penis twitch. She pushed herself on even deeper, eager to catch it all.
“Uuhhhhhh,” he moaned.
She held still, waiting until the spurts of cum died down, and swallowed.
“Mmmm, that was so wonderful, Anna.”
Realising the magnitude of how much this pleased him, Anna followed soon after. The second orgasm was even better than the first. She screamed with joy, hips bucked, body trembling, world blurring. Nothing she’d done before had come close – she had scarcely known such a pleasure could exist.
They both sat where they were and enjoyed the moment. If somebody had walked in then and there, Anna couldn’t have explained the situation. It absolutely wasn’t what it looked like – this was not just for their gratification, this was a necessary part of the process. Her therapy had taken a strange turn to be sure, but she was very glad that it had.
As she laid still, Doctor Stewart’s phone rang. She didn’t move, but he sluggishly grabbed the device and answered.
“Hello?”
Anna stared out the window into the darkness and closed her eyes.
“Wait slow down, slow down Mia… take a deep breath. What’s wrong?”
She turned to look, and saw that he was quite upset by something.
“You saw what?!”
Thirty Minutes Earlier
On the way home, Mia was feeling optimistic. All things considered the day had gone really rather well. No fresh dramas, she got a whole bunch of work done, and to top it all off, Adam seemed to be genuinely repentant. She was feeling so good that she decided to treat herself to some Japanese for dinner. Not far from her home was a truly lovely restaurant. It was fairly traditional, and a little pricey, but her stomach had a hankering for the wagyu beef udon set.
Mia placed the order at the front desk, then took a seat while she waited. She opened up her phone and started catching up on her daily feeds. She took great care to curate her social media consumption – a steady stream of lovely little animals were the perfect antidote to the overwhelmingly negative things that used to populate it. She was unable to contain a smile as she looked over an animated image of a baby hedgehog waddling up to a cat, which leapt away in shock when it turned its head.
Not long after she exhausted her supply of adorable content, a message popped up on the side of her screen. It was from Cordelia from work.
“Um, holy shit.” Another message followed shortly after. “Holy shit Anna you need to get back to work right now.”
Mia frowned, then moved to reply.
“What’s wrong?”
“I don’t know if I can begin to describe this. You need to see it. Somebody has been posting this stuff up in the toilets.”
“I’m already almost home, can’t you just show me what it is?”
“It’s pretty fucked up. I’m warning you.”
Now she had to know what it was.
“Please tell me what I’m working with here. Or show me.”
There was a long pause.
“Ok, but I did warn you.”
A picture popped up on the screen. Mia nearly dropped the phone. The colour drained out of her face and she raced to cover the screen before somebody saw… that. She looked around her, dreading the possibility that somebody might have just seen it. Why the fuck would she sent me this?
She slowly uncovered her hand to look again. Had she imagined it? It quickly became apparent that she had not. It was pictures of people engaged in sexual acts. But there was something more unsettling than that. Something impossible. She turned the phone screen off. Mia stood and raced into the bathroom, heart pounding. It was unoccupied, to her relief, and she sat down on the stall. Her hand shook as she brought the phone up to her face again and pressed the button.
A man was standing at the top of the frame, only the very bottom of his chin visible, his arms wrapped around a woman. Her face was covered with… oh my god, oh my god…
The woman was her.
Mia screamed.