Doctor Casandra Wilson had been lonely for a while. While it was true her last relationship ended several years ago, she had only really gotten lonely in the past few months. She had heard from a friend of hers about a pretty decent local dating site, especially for people looking for what Dr. Wilson was looking for.

While a relationship would be nice, she was really needing a little sexual gratification. She had joined the site with an email she had set up just for such purposes. She paid for a year’s membership with a gift card to keep it isolated from her credit cards.

She had been browsing for a while, almost regretting signing up for a year membership because most of the profiles she had seen so far were just trying too hard. Profile pictures of dicks as far as the eye could see, and men wanting a fleshlight with a pulse. Then she saw one of her matches that wasn't like the other.

His profile picture was part of his face. It had enough details that maybe someone who knew him wouldn't recognize him, but it showed he was a little heavy-set with a warm smile. His list of likes matched hers.

She wasn't sure if his "looking for" age range was set from eighteen and up for the purpose of casting as wide a net as possible or if he was specifically looking for teens. She was in her mid-forties, so she was close to his age. He seemed pretty articulate in his profile describing himself.

What really drew her attention, though, was in the section describing what he was looking for.

“Hi, I’m a D/s Switch interested in exploring his submissive side. In particular, I have an interest in some medical adjacent fantasies that would dove-tail into some of my other interests including (but not limited to) CFNM, Mild CBT, embarrassment/humiliation, orgasm control, teasing and denial, and anything clinical.

"I'm looking for something with a slow build-up over weeks or even months, with the woman setting the pace she enjoys and feels most comfortable at. I am hoping to find an articulate, interesting woman with a bit of a dirty mind who enjoys exploring me as much as I will enjoy learning about her and exploring her mind and eventually her body if she is willing.

"In a perfect world, this would turn into a real relationship. Even if we don't click I'm looking to make a few exciting new memories and explore a fantasy I've never realized. Feel free to contact me here. I look forward to hearing from you.”

What she found the most exciting was the way he used the word realized. Not like someone came to understand a thing, but in the sense that a thing was made real. It showed a level of literacy that was light years beyond most of the other profiles she had seen. She knew she was going to respond, but first, she needed wine.

She moved from her computer to the kitchen, grabbed a glass from the hanging rack under her cabinet, and opened the fridge to take out the nice bottle of white she had started on yesterday with her friend. She poured herself a tall glass and replaced the cork in the bottle. She took a long slow drink from the glass and made her way back to the computer and clicked the button to send this man a message.

"Hello there!

"Your profile was very interesting to me. You seemed articulate, intelligent, and interesting. I would be very curious to talk to you a little about some of your fantasies, especially those related to your medical interests.

"I've never been a real dominant before, but I have had an interest in BDSM almost since I got interested in sex. I also may have a unique way to indulge some of your medical fantasies in particular, though I am a little nervous about explaining exactly how that is. Would you mind if we spent some time getting to know each other and building trust before we agree to meet?"

She reread her message a few times while sipping her wine. She finally reached the point where she knew if she didn't hit the send button then she might not ever. She moved the mouse to the send button and clicked it. She watched the message disappear on its journey to this man who had sparked her interest.

She continued browsing, looking to see if there were any other interesting men. She found a few, but nothing quite like that first profile that caught her attention. She did send a few other messages in the interest of not putting all her eggs in one basket.

Suddenly there was a chiming noise and a little indicator on her profile picture. She had received a new message! She shifted in her chair and clicked the message to open it.

"Hello!

Thank you for responding to my profile! You seem very interesting, articulate, and intelligent yourself. That means a lot to me. Since you said you were curious about some of my medical fantasies, I thought I would mention a few of the tamer sorts of ideas, 'first dates' of medical kink if you will.

"I'm not saying I'd expect this on a first date or anything, just saying that it's the tamer end of the spectrum. I love the idea of a sort of basic physical examination, including having to strip naked in front of you, letting you weigh, measure, examine, and scrutinize any part of me you want.

"It doesn't have to be an examination of my genitals, but being naked while you are dressed would be a thrill and that clinical, detached sort of feeling would leave me in an isolated headspace, making me feel very vulnerable. If you were interested in anything more than a basic sort of 'playing doctor' I would love to hear what you think.

"Also, I want to be clear, I'm not looking for sexual release from you, though that would also be greatly appreciated and enjoyed. If you decided you wanted a release I would be glad to give it to you. I would expect nothing in return.

"As to your question about getting to know each other, I would love nothing more. If you want to chat in real-time or keep sending messages back and forth like this, both are fine with me. If you want to meet face to face, look me in the eyes and judge my character... you pick the time and place and I will be there with bells on. Literally, if you like.

Yours sincerely,

Jackson"

She felt a little thrill in her chest as she read his words. She liked his response and how he seemed to be saying all the right things. She had heard men who had an almost preternatural ability to say the right thing even if they didn't mean it, but he felt earnest to her.

She liked the idea of meeting him before agreeing to get sexual with him. She also liked the fact that he had answered her questions and offered information but not demanding anything like her boob size or pictures other than what she had put on her profile. She thought about her response with a second glass of wine.

Part of her wanted to chat with him, either through the website or something else, but a bigger part of her felt like that technological divide might allow him to conceal some truth from her. She trusted her instincts more than words on a screen. She enjoyed about half of the second glass of wine while rereading his message.

She imagined having him undress for a physical examination. Cassandra giggled at the thought of taking his temperature rectally in a completely unnecessary way. She wasn't a proctologist by any stretch, but the thought of a prostate examination made her smile.

Cassandra had heard that a man could orgasm from prostate stimulation alone and had always wondered if that was true. She was getting a little turned on by all this and came to a conclusion as to what her response to his message would be.

"Two days from now, on Friday. Lunch at Garcia's on West. Wear a red tie so I know it's you. My schedule can be pretty tight so I need to be at the table with you at noon sharp."

She hit send and before she could give in to any other temptation, she closed her browser and shut the machine down. Cassandra drank the last of her wine and decided that she was going to enjoy herself a bit before bed. She made her way to the upstairs bathroom and looked at her face in the mirror.

She had taken her makeup off after work, but her long, dark brown hair framed her face nicely. Her brown eyes were bright and clear. They were a little bloodshot from staring at the screen of her computer for a few hours. She was pretty enough, and she was reasonably fit if not toned.

She began stripping for the shower, removing her top first. She never liked that comfortable bras were always so plain. She idly wondered if it would kill the bra manufacturers to put a print on them.

At least this one didn't dig anywhere and kept her chest supported without too much of a fuss. She unclasped it and breathed a sigh of relief at the release as she cast the bra into the hamper. She slid her pants down with her panties which were also a plain affair.

"Jackson. I like that name. Not Jack, but Jackson. Sort of how I'm Casandra, not Cassie or Sandra."

She stepped out of her pants and was now fully nude. Her hand made its way slowly over her stomach and pubic mound. Her fingers clipped through her trimmed hair like a lover’s caress while feeling their length.

Cassandra kept herself trimmed short not for any man, but because she just didn't feel clean with longer hair. It's also why she shaved her legs and armpits. Not for a man or society, but for her own feeling of cleanliness.

She turned on the water and stepped into the shower once the water had reached her preferred temperature. Cassandra set the shower head to its massage setting and took the wand off its holder. She was careful not to wet her hair, as she didn't want to have to dry it before bed.

Cassandra let the pounding water impact on her chest as she pictured a sexy doctor's visit. The first thing she decided was the stripping needed to happen very slowly and in front of her. She wanted to drag this out as much as possible.

She moved the stream of water to her left breast first and moaned softly as it impacted her. Cassandra let the stream meander from the top of her breast to the outside and then inside over and over as she pictured a strange man getting undressed for her.

When she pictured him finally dropping his underwear to the floor, exposing his cock and balls, Cassandra aimed the water right at her dark, sensitive areola. She moaned in pleasure and pictured him having to turn around. The stream wandered to her other breast as her hand moved to tease her labia.

She spread her legs and rested her butt on the cool tile of the shower wall. Her lone finger ran up and down her opening, feeling that she was surprisingly wet already. Cassandra hoped the meeting went well because she needed something in her sex that wasn't hers.

She imagined him having to demonstrate his flexibility and balance for her, like a slow-motion nude dance. Cassandra’s finger parted her lips finally and slipped it slowly in her wet pussy. Her finger went straight to her G-Spot. She loved how that little bundle of nerves made her feel as she pressed into it gently.

Cassandra gave herself a second finger as she pictured taking his temperature in more detail. She imagined spreading the lubricant over his anus, and then inside him with a gloved finger. She wondered if he would like her throwing the soiled glove away the moment it was out of his ass, replacing it with a clean one as if he were intrinsically foul?

Her thumb moved to her clit as she saw the thermometer disappearing into his hole and making him hold it for a few minutes. He was bent over, afraid to move with a glass tube in his rectum. Cassandra wondered if it would be possible to fuck him with it?

Cassandra was sure she could find some other medical implement safer than a glass tube. Probably something from an enema kit. Could an enema be sexy, she wondered?

Her thumb circled her clit a little faster and her fingers pressed more greedily into her pussy. The water pounding on her breasts had left them both tingling, and she wanted that pleasure elsewhere. She slowly traced the stream of water over her chest and stomach, then aimed it right at her pussy.

"Ohhh that is what I want!"

Cassandra slapped the wall of the tub as intense pleasure rushed through her. She was near an orgasm and beyond thinking about his fantasy and instead focused on what she wanted. To leave him exposed, to make him feel vulnerable and weak as she pleasured herself without him seeing anything.

That shame and humiliation on his face that so many other women had felt naked at a doctor's on his, and her being the one to take blatant pleasure in it was intoxicating. She could see why so many men abused their power. Cassandra wanted to abuse this man, and this was just a fantasy!

Picturing the look on his face that said 'I'm just a piece of meat' was what sent her over the edge. She had a potent, vocal orgasm as she trembled in the shower. Cassandra thumbed the shower head to its cascade function to prevent herself from becoming overstimulated.

She cleaned up, feeling the lingering joy of her orgasm. As she rinsed her body off, she deeply hoped that her meeting would be fruitful. Turning off the water, Cassandra dried herself with a giant, fluffy white towel.

Cassandra felt so alive she decided she would sleep in the nude. She slipped into bed and shuddered in pleasure at the feel of her sheets on her bare skin. She drifted off to sleep peppered with erotic thoughts and dreams.

That Friday...

Friday morning, Casandra put on a lacy bra and panty set in light blue. She knew no one would see it but her, but the fact she knew how she looked would add to her confidence. She wanted to exude sexiness.

She picked a pair of pantyhose that was suitable for work and a nice black skirt that just covered her knees. Cassandra opted for a white button-up blouse that she could undo a few extras when she left the office to be a little sexy while still being professional. Her final choice was shoes.

Cassandra had a closet full of shoes. She wanted something a little playful for lunch but still professional. She picked a black peep toe with a sensible heel. She slipped them on her slender feet and settled into them.

The day could not go fast enough for her. The clock kept winding backward as she was eager to meet her man for lunch in Cassandra’s perception. Finally, she was out of her morning patients and out of the office like a shot. She waited until she got to her first red light to undo a few buttons of her blouse to hint at cleavage.

She made it to Garcia's and told the hostess she was meeting someone for lunch. As the hostess started to ask if she could give the name of her party, but Cassandra saw him. She would recognize that smile anywhere, and he was in a red tie!

"He's right there."

The hostess lead her over and Jackson rose to greet her and to take her seat out for her, letting her scoot herself forward.

"Chivalry or sexism?" She asked.

"Respect. Chivalric codes were about how to treat horses."

His voice was nice. Rich in tone and flowing in cadence, it made her smile. He was smart, but not arrogant about it. He was witty and made a good first impression.

"Nice to meet you, Jackson. I'm Casandra."

She held out her hand and he took it. Shaking it, then bringing it to his lips to kiss it gently and respectfully.

"A pleasure, Casandra. I didn't know what you wanted, so I started with the queso. I figured it would be hard to go wrong with melted cheese unless you are lactose intolerant."

"A great choice. I love the queso here."

Things were off to a good start. How well could this lunch go?