tagBDSMThe Naughtiest Doctor

The Naughtiest Doctor


If you are very lucky, you might meet someone at work that you really connect with. Someone who brightens your day. Someone you have more in common with than walking around on the same bit of carpet for 8-12 hours a day. For me that person was Dr Stephanie Benz.

As the Hospital's lawyer, doctors were rarely happy to have me rattling around their hallways. Hearing that I was looking for them usually meant a pending malpractice lawsuit, or their contract was up for negotiation in less favourable times.

Dr. Benz was an attending urologist. All I knew about her before becoming acquainted was that she was one of the hardest working doctors on staff. Patients and staff alike loved her. When a position opened up for the Chief of the Division, management wisely set me the task of tendering an offer, finally able to recognise her contribution to the hospital. This was one of those scarce scenarios when the good doctor was happy to see me. I set a meeting via her assistant. When our meeting came around I was not prepared for what I saw.

Despite being in her mid-forties, and having a couple children, she was breath taking. Wondrous copper skin, hair the color of almond butter, and piercing green eyes. She was like a fine wine: aged perfectly. Introducing herself, she shook my hand. Her hands were warm, and softer than I anticipated from a surgeon. I felt extremely awkward being in close proximity to someone as far out of my league as I considered her to be. My heart raced the entire meeting. She was charming, and ecstatic about the pending promotion.

Subsequently, every time I caught sight of her around the hospital a smile came to my lips, and my blood rushed to my crotch. I would pop into her office every chance I could during contract negotiations. Our exchanges were always affable, and wonderfully easy, which naturally evolved into friendship. Once her new contract was complete, Stephanie (since she insisted I call her by her first name), and I took to having lunch together when our schedules would permit. Our colleagues joked she was my "work wife." I didn't mind the jokes, I knew they were well intentioned. Besides, who wouldn't want to be closely associated with such a lovely woman? I loved being near her, loved the smell of her shampoo, loved the warm laughter she exuded. I had a crush.

On a tedious Tuesday that felt like any other I was enjoying a drink and a cozy haven from the blisteringly cold winter's day at my work's preferred drinking haunt, when I slighted Stephanie pushing her weight against the heavy door of the bar. Stepping inside she wrestled with her many outer layers, freeing herself from her bulky winter protection. Once succeeding with the task at hand, she nervously cast around the room searching for friendly faces. She didn't usually socialize with colleagues outside of work, and an adorable frown creased her forehead as social anxiety made her second guess her joining us. Spotting me she smiled in relief, and gave a small wave and hand gesture denoting she was going to grab a drink. Drink in hand she made a b-line to the safety of my side.

Stephanie talked my ear off all night, and I drank up word, savoring our personal conversations as always. As the alcohol flowed our innocuous chit-chat about work, television, and shop talk eventually gave way, to more serious discussion. Letting down her guard Stephanie opened up about herself as she never had before. She explained that she always felt underestimated because of her looks, that in turn led to her need to overachieve. Doctors work a lot of hours; overachieving, hardworking ones even more. Taking a deep breath she confided that her husband had decided he had had enough. He wasn't coping with the neglect her work caused on their marriage. Her newly won promotion was the straw which broke the camel's back. He knew he couldn't deal with the kids, in conjunction with the stress levels the increased burden her new promotion was sure to induce. As such, they had recently separated. I didn't know what to think of this. We were close, and I felt regret at her loss.

Since I could relate, I did. I had never spoken to anyone at work about my marriage, but that evening I opened up. I explained how I had been working late hours on a major project for the Hospital, then there was another big project, followed by another, and another. My wife couldn't deal with me being an absent husband. She didn't sign up to be alone. She was more of a house keeper or personal assistant running all the household affairs by the end. By not spending quality time together, we grew apart. When it ended, we both just knew it was time to move on. My wife agreed our separation was just a formality by that point. Neither of us felt shame or sadness, it just happened. 'Moving forward' we called it. Stephanie sat there silently and attentively, never uttering a peep as I relayed my story. When I was done she leaned forward throwing her arms around me pulling me into a deep hug. I breathed deep, smelling her hair that awkwardly planted in my face. It smelt wonderful; of coconut and vanilla.

Many drinks in I asked her if she wouldn't mind putting on her doctor's hat for a minute. She mimed putting a hat on her head.

"Haha, very funny. But I am being serious now. I am pushing 40. Since we friends and all, and I know you're a great doctor and all that, would you mind if I picked your professional brain about a personal issue?" I asked her.

I knew I had an issue that really should be treated by a doctor. I stupidly kept putting it off, telling myself it was 'nothing' or even if it was 'something' a doctor probably couldn't help. Abetted by bourbon, and my trust in Stephanie, I found the nerve to say 'I have a problem' and ask for help.

"Of course. You're my favorite lawyer." She answered warmly.

I mumbled something about it being embarrassing prompting her to slip reassuringly into her wonderful bedside manner. Placing her hand on my arm she told me in a tone of unadulterated sincerity, that she wanted to know what was wrong, and how she could help. Her grip was firm, one that offered reassurance, inspiring a sense of courage. Unperturbed she asked me plain and straight: what symptoms did I have? What was wrong? I mentioned having to pee a lot. She cocked an eyebrow as if saying "Aaand?" Answering in an almost inaudible whisper I tell her about my failure to keep myself hard. Due to the din of the bar, she smiled asking me to repeat that last bit.

"I sometimes can't keep it up. I can get hard, but then it just goes limp." I told her, my personal shame spewing forth.

"Oh." She nodded her head gravely, her brow knitted down into a frown of consideration. "Well, I know it sounds cliché, but that happens to lots of men. No really, I know, because I am a doctor. Men tell me about it literally all day. Every. Single. Day. You have no idea how many dicks can't stay hard out there."

She laughs lightly trying to ease my tension. I laugh nervously at her jokes. It was a dry sense of humor, delivered in the perfect manner. I allow myself to relax a little.

"Look, from the sounds of it, I am leaning towards a potentially enlarged prostate. We can do a blood test or I can check it for you myself. The blood test takes a bit of time to come back, but if I do a manual check then it would be quick and easy."

"You'll check it?" I ask her, not fully comprehending what a 'manual check' would entail.

"Of course. I won't go back into the Hospital after drinking, but my brand spanking new apartment is 2 blocks away. Come over. I'll check you out." She reaffirms the grip on my arm telling me "Look, I am sure you have nothing to worry about, but it never hurts to get things checked out by a doctor."

"Come over... Like now?" I ask nervously. A part of me cannot believe that this woman wants me to come home with her, even if it's just a course of treatment.

"No time like the present. Finish that drink and let's get out of here."

The wind bites both of us on our walk, regardless of how bundled up we were. Luckily, she really was only a couple of blocks away. Before long we're in her apartment.

Stephanie was a slob. Suitcases open with strewn clothes everywhere. I didn't know that a single person could own as many pairs of green scrubs as she did. Stale coffee sat left in the percolator pot. The place reeked of neglect and charm. It was incredibly endearing to see someone whom was in complete control of their professional life, someone at such a high level in their professional field, brought down to earth by simply having a messy apartment.

I mentioned having to use the restroom, she pointed me in the direction. It wasn't much neater in there. Spying a black lace bra hanging from the doorknob, I reach out hesitantly, knowing I was crossing a line, but unable to control the impulse. Picking up the black lace garment I gently stroked the soft textured fabric. Bringing it up to my nose I inhale deeply. It smelt musky, with a hint of lingering perfume. As if caught red handed I hastily fumble it back onto the doorknob as Stephanie's rustling around close to the bathroom door startles me.

"Sorry, I wasn't expecting company." she told me as I sheepishly re-entered her living area.

She is frantically stumbling around, picking up clothes, tossing them into a pile in the corner in a vain attempt at gaining a semblance of cleanliness.

"Since Josh filed for divorce, I've sorta just been living out of suitcases."

Clearly proud of her handiwork, she put her hands on her hips, and cast around admiring her 'clean' apartment.

"There, clean enough for your procedure" She proclaimed proudly.

My nervousness and trepidation of being in alone with a beautiful woman in her apartment, something I hadn't done since before meeting my ex-wife, combined with concern about my condition must have shown on my face. I nodded in affirmation, but she sensed something was amiss.

"I get that you're nervous. A lot of men are when they have this done. I promise you, I am gentle."

I nod, trying to permit myself to feel comforted.

"So, here's how I check the prostate. I am going to press a finger into your anus, reach forward and manually check the gland. I will feel around to see how big it is, check if there are any lumps or other growths on it. It's called a digital rectal exam." She explained in a professional breezy manner.

"I was worried that's what the exam was." I replied nervously "Do I cough or something?"

"Ha-ha... no. You turn around facing away from me, just pull your pants and underwear down, spread your legs and try to relax."

Try to relax? Easier said than done. I stand up looking dumbly around for an appropriate place to stand.

"Go on. I won't bite. Look, I even bought you a drink before telling you to take off your pants." Stephanie encouraged.

I genuinely laugh at that one. Her sense of humor waylaying my fears.

Following the Doctor's orders, I turned around to face the wall. Whilst admiring the lovely brickwork of her apartment, with numb fumbling fingers, I slowly unbuckle my belt and pull down my slacks and briefs.

"Don't worry, this doesn't hurt." Stephanie soothed.

SNAP, a latex glove gets pulled into place. I turn around, startled at the sharp sound. I am rewarded with a gorgeous smile on her face.

"Just having fun with you. Really though, I am gentle. Just gonna get some lubricating gel on my finger. This might be a little cold. You might even turn out to like it."

With a resolute sigh, I spread my legs.

Never having experienced anything like a rectal exam, my mind starts to race. What will this feel like? Am I going to like it? Will she think I am gross? What if I get hard? What if I accidentally cum... will she just throw me out and not speak to me again?

Her left hand firmly grips my left hip. I feel a cold wetness on my asshole. My body shivers involuntarily. I am surprised when there is no poking or prodding, just a little gentle rub on the surface of my hole. This wasn't so bad. The rubbing continues until my sphincter relaxes.

"There we go, you're all lubed up. Now, I am going to very slowly, and very gently insert my finger to feel around. Just... try to relax." Her voice was calm, clinical and soothing speaking authoritatively with an air of total confidence, and reassurance. It had her desired effect, as I felt a bit more at ease.

"While I check you out, I have some questions I need you to answer. Be honest." Stephanie explained.

"Sure thing."

"When was the last time you ejaculated?" Stephanie asked me as she begins to increase the pressure of her finger.

"Uhm. I am not sure" I respond, a bit taken back by her directness, and by the foreign pressure on my asshole.

"Not sure or embarrassed?"


"Don't be embarrassed. When was it?"

"Two weeks or so ago." I answer her.

"That may have something to do with this. When was last time you had sex?" She followed up.

"Not since I was married, so a year or so ago?" I respond quickly, trying to keep my voice straight.

"I am going to apply more pressure now." She cautioned.

The sudden, albeit warned, pressure of her deft finger against my prostate saw me squeak involuntarily.

"Shhh... it's okay sweetie. I am in, just let me work."

Sweetie? I thought.

Never having taken anything in my rear end before, her forefinger felt expansive. It feels almost overwhelmingly large as she prodded around, pushing and expanding on my ring. As she wriggles her finger around a sense of pressure inside of me builds. Unbidden my cock stirs from her ministrations. Her finger's swirling gives me an insight of pleasure, the like of such I had never experienced. Desire from the new sense of physical pleasure clouded my mind. Her finger continued to work its magic. I was rendered unable to think of nothing but the sensations her finger is causing.

Unfortunately, as quickly as it started, the finger was gone. A disappointed moan escapes my lips.

"Pull your pants up." She tells me, stepping back "Good news. I think you're fine, but I want to take another longer, more in depth examination of you."

Fear and reality crashed into me. I didn't know what to say. I was floored. Am I sick? Oh my god... I am going die, aren't I?! Do they cut off your cock to save the rest of your body like a tumor? These and a myriad of other horrible thoughts penetrated my consciousness.

Taking in my panic-stricken face, Stephanie steps in to reassure me.

"No, no, no, please don't worry. You feel completely normal. But we've been drinking... I've been drinking... heavily. I just want to make sure." She explained in a rush. "Tomorrow, I have a full schedule at my private practice downtown, but stop in after work for my last appointment. I want to give you a proper exam."

She took the glove off tossing it in the trash.

Looking down at the ground, I mumble "sure thing" as I buckle up my pants.

She placed a hand on each of my shoulders, her strong grasp showing she was in control. Looking me right in the eyes, she says:

"I care about you... a lot." She reached a hand up to gently caressed my cheek. Her soft small fingers provide a soothing touch against my beard. "I will always take care of you. Tomorrow at 7pm, my office. Don't worry about a thing. Trust me."

She flashes her beautiful smile again.

"But before that, I have some 'medicine' to help ease your mind and put a smile on that pretty little face of yours. If you don't mind, I'll crack open a red?" Sauntering over to her wine rack she selects a bottle. Deftly removing the cork she pours us both a healthy glass.

"To your health" she toasts handing me a glass.

We chink our glasses together in a 'cheers' and drink deeply. We quickly polish off our glasses, drinking with minimal conversation. During our refill, Stephanie says:

"I didn't even realize it, but this was the last bottle Josh and I had from our wedding. I guess in some ways, it's like moving on." Her tone is bittersweet.

Holding up her glass to the light she examines its contents. Her expression is unreadable.

"Well, I'm glad I get to share it with you." I tell her, genuinely glad that I was a part of her life.

"There's no one else I would rather share it with. Really." She says with a smile.

Moving to her couch we drink and conversation, like the wine, flows freely. Her jovial personality allayed any niggling concerns I had. Before long she had me laughing full throatily, completely care-free. Stephanie was truly a marvel at making people feel better. It was like a part of me knew everything would be fine.

As we relaxed into the evening and each other's company, she picked her legs up, and swung them over my lap causally lounging on me. My arms resting on her thighs. A cheeky little voice in the back of my head tells me she might be more interested in me than I originally thought. I easily recall the sexual energy I felt while her finger was probing my rear end. My hand on her smooth upper thigh itched to slide the short journey upwards to that which I know is nestled between her legs. Would it be warm, wet, and welcoming? My heart skips a beat at the thought. My lack of confidence from being out of the dating game for years, coupled with the shear dread of humiliation at the possibility of not being able to sustain an erection for such a beautiful enticing woman kept my behavior in check. Still, I couldn't help but feel a stirring of my cock. Embarrassment crept over me as my cock kept getting harder, rising up against her leg. She must have felt its tumescence. She causally adjusts her leg, causing the back of her thigh to slightly rub against my length. She smiles like the cat whom got the cream, yet innocently upkeeps the pretense that she's not acutely aware of my rock-hard cock.

"You really haven't had sex in a year?" Stephanie asked me an incredulous eyebrow raised.

"Yeah, really." I nod, trying not to be embarrassed by the sad truth.

"Well... what about anything else?"

"No..." I say looking down at my lap, my face hot with shame.

"Well, I am sure that'll change before you know it." Her leg stilled.

I know it was a cue to make a move on her, but I wasn't sure what to do. It had been a long time since I had been to a girl's apartment, let alone attempted to be remotely physical with anyone that wasn't my wife. Decision paralysis set in. I didn't make any advances. Finishing off the bottle Stephine yawned sleepily. This time I do not miss the social cue. I tell her it's getting late and call an Uber. Walking me to the door, Stephanie gives me a goodbye hug. On my way out, I feel an unexpected slap on my ass.

"Can't wait to check this thing out again tomorrow. Good night." Stephanie chuckles to herself as she closes the door behind me.

During what seems like an eternity of a car ride home, I think to myself What does she mean by "can't wait?" Oh god, I should have made a move when she had her legs over mine! What if she thinks I'm not interested? She must think I'm a big impotent loser...


I had never been to Dr. Benz's private practice. Only tidbits about it from our lunchtime conversations. It was a small private practice, a bit too small for her liking, in the bottom floor of a brownstone near the Hospital. She absolutely adored the building, and neighborhood it was in. She was the sole doctor whom practiced out of it.

On my way over, I received a text telling me that the staff had left for the day and to call her when I arrived so she could let me in. Greeting me warmly, she looked professional as always, wearing her usual white physician's coat with her stethoscope around her neck. Her hair was tied back in a neat little ponytail which swayed gently as she walked. It was impossible not to notice her stilettos and her perfectly toned calves. Locking the front door behind her, Stephanie makes a sweeping gesture around the office.

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