The New Boss

Karen had just moved to town after taking a job with a new company. She smiled whenever she saw her new boss. He was very distinguished looking, tall with graying hair. He had an air of authority about him that made Karen’s heart skip a beat. She thought about him often while she unpacked her things and arranged them in her new apartment. For the next several months though they exchanged nothing more than smiles and casual “Good Mornings”. All that changed though when Karen came down with some kind of “bug”.

She hadn’t been feeling well the day before but refused to call in sick having only started working at this job a few months ago. So she had gone in and continued working but that Friday she began to feel even worse. She knocked on John’s door and entered. “Mr. Simpson”, she began but was interrupted, “Please call me John”, he smiled at her. Karen smiled back, their eyes met and something seemed to click between them. “I’m sorry, but I’m really not feeling too well and I think I’m going to have to go home early today”, she told him. “You do look a little pale” he replied with some concern and reached out to feel her forehead. “I think you’re running a temperature, yes, you should go home and take care of yourself”, he said with some tenderness as he removed his hand.

Karen found herself blushing as she drove home, remembering the cool feeling of Mr. Simpson’s hand upon her forehead, becoming excited again just remembering his touch and look of concern. “He sure is good looking” she told herself.

John watched from his office window as Karen drove out of the employee parking lot. He was attracted to her for some reason. She wasn’t tall and beautiful like his ex-wife, but more short and average looking. But she seemed to have a good sense of humor and a nice smile. He would we drawn to her laughter as he passed through the office. He found himself

watching her as she interacted with the other employees, most of whom were male and had a bad habit of telling off color jokes and kidding around. But he was pleased to see she could handle herself just fine, she gave as good as she got and never seemed to get bent out of shape or upset when some rather crude remark was made when kidding around with them.

He went to the cabinet holding the employee folders and extracted hers. He began to read through it. She was single with no kids. He wrote down her address and phone number on a small piece of paper and slipped it into his pocket.

Karen lay in bed not feeling much better than yesterday. “At least it’s Saturday and I won’t have to call in sick again” she realized. She eventually got up and made a pot of coffee and sat down in the living room to slowly sip it. She hadn’t been able to keep anything more substantial in her stomach. She had been living on coffee for the last several days, but found that the constipation she was also suffering through even worse. She laughed to herself as she prayed for a good bowel movement. “Cute Karen” she told herself. She was surprised when she heard the knock at the door. She got up slowly and peaked through the little hole, her stomach began to flutter when she saw Mr. Simpson on the other side. It was only after she had opened the door that she realized she was wearing only her “sleep t-shirt and her hair was going in all directions, quite a pretty picture she thought silently”.

John smiled at her, his groin stirred a bit as he saw her standing there dressed only in a t-shirt. The image of her in a hospital gown popped into his mind. “I just wanted to stop by and see if you were feeling any better, you really did look awful the other day”, he said awkwardly. Karen couldn’t imagine looking any more awful than she did at the moment, but knew what he was trying to say and responded… “I’m feeling a little better, and it sure is nice of you to be so concerned, would you like a cup of coffee?”, she asked and opened the door wider, inviting him in.

John stepped in and stood nervously as she brought the coffee. They sat on the couch and sipped their coffee and talked about nothing in particular. “You know, you still look pretty flushed, are you running a temperature?” John finally asked bringing up the subject that was so dear to his heart. “I’m not really sure, I don’t have a thermometer, I just moved here a few months ago and I never thought to get one”, she replied quietly. John jumped up and started for the door… “There’s a drug store down the street, I’ll go get you one right now, be back in a few minutes”, he called out as he left. He had a habit of acting impulsively, a trait his ex-wife did not find very indearing.

Karen was left staring at the door as Mr. Simpson left. She felt a little tingle in her groin as she thought of thermometers and having her temperature taken. For some reason she found the idea of having her temperature taken rectally really exciting to her. “Surely, he won’t get a rectal thermometer”, she sighed to herself and returned to her coffee. Twenty minutes later he was back with an unusually large bag for something so small as a thermometer. “Uhhh….I picked up a few other things I thought you might need”, he said as he saw her looking at the large, brown paper bag. He began to pull some items out and place them on the coffee table.

Karen looked down at the coffee table but said nothing as John placed first the small jar of vaseline and rectal thermometer down. He purposefully left the other items in the bag and set it down. He noticed the slight blush that appeared on her face as she saw the vaseline and rectal thermometer come into view. He knew exactly what she was thinking of. “If you want, I can wait here while you take your temperature in the other room, I don’t mind”. He waited for Karen to respond but she remained silent, still staring down at the glass rod laying on the table. Finally she spoke.. “Umm..isn’t that a rectal thermometer” she

stammered. “I don’t think I can do that”.

John’s heart skipped a beat as he replied.. “Rectal temperatures are the most accurate, especially if someone has been drinking something hot like coffee… I can take your temperature if you like, I’ve done it before”….he trailed off, letting the question hang in the air between them. Karen didn’t answer but continued to look down at the thermometer and vaseline. John sat down on the couch and reached for her hand, taking it in his own and gently pulled her closer to him. “Lay down over my lap Karen”, he said softly as he guided her next to his right leg. His confidence grew along with his penis when Karen didn’t pull away from him in horror and run screaming for the phone to dial 911.

Karen allowed John to position her next to his right leg and finally bend her down over his lap. She closed her eyes tightly as he gripped her about her waist and raised her up a few inches before placing her back down so that her bottom was comfortably resting on top of his crotch. Her legs were stretched out on the couch to his right, her torso to his left. She wrapped her arms together and lay her head down waiting for what was to come next. Her mind raced back to the last time her temperature had been taken rectally. She had been about twelve years old, and had gotten sick at school, her mother had been called to

retrieve her and when they had gotten home her mother had placed her face down on her bed and pulled her panties down before inserting the thermometer. She could remember laying there for a long time hoping none of her brothers would walk down the hallway and look inside her bedroom and see her getting “the thermometer”.

John held his breath as Karen settled down over his lap, his penis growing larger. He reached down to the table and opened the jar of vaseline, then unwrapped the rectal thermometer and poked it in, letting it stand there until he was ready for it. He looked down and inhaled deeply as he saw Karen’s small form laying over his knees. He slowly pulled the back of her t-shirt up and out of the way. He slipped his finger under the waistband of her panties and began to pull them down until they rested at the back of her knees. He placed his large hand on her naked bottom and cupped her cheeks gently, “Are you OK?” he


“I’m ok” Karen responded covering her face as her bottom came into view. His hand felt very warm on her naked backside. She tensed her butt and felt John give it a quick, gentle squeeze before removing it. She could hear the rustle of his clothes as he reached over for the thermometer. She held still as John pried her cheeks apart and began to insert the cold thermometer into her rectum. Her head raised up a few inches as he slid it deeply into her and held into place. Her buttocks relaxed as she

got used to the feeling of the glass rod in her backside and lay her head back down with a sigh.

“That doesn’t hurt does it?” he asked ejoying the picture that lay before him. He had longed to play doctor with his beautiful ex-wife but when he had brought the subject up that one and only time she had almost laughed in his face. Things had gone downhill from there and they had soon parted company. There were a lot of other issues that helped drive a wedge between them, but the look of disgust on her face when he had suggested she “bend over” so he could give her an “exam” remained fresh in his mind.

“No, it doesn’t hurt” she answered truthfully, “but it’s kind of embarrassing to have my temperature taken this way, It’s been a long time since my mother held me down and did this, sometimes I would cry as she pulled my pajama bottoms down and put the thermometer in. She had a habit of leaving my bedroom door open and my brothers were able to look in and watch. I can still remember their stupid faces grinning as they punched each other and pointed at me as my mother held me across her lap.

John lifted the back of her t-shirt a little higher and began to massage her lower back as he waited for her temperature to register. He continued to hold the thermometer securely in place, his right palm cupping her small bottom, the glass rod between his fingers. He could almost feel it move slightly with each beat of her heart. “Have you been eating anything”, he finally asked, breaking the silence.

“No, I can’t seem to keep anything down” she answered. “That’s not good, you need to take something,… spending a lot of time in the bathroom?”, he asked suddenly almost wishing he hadn’t said it. Karen giggled, “Just the opposite!”. She groaned to herself when she realised what she had just said. She felt the thermometer being pulled from her bottom and suddenly felt a strange emptiness. She was thinking of some way to get up and off John’s lap gracefully when she felt his hand once again on

her backside.

John held the thermometer up and read it, she had a little bit of a fever, but it was the brown smudge on the bulb of the glass rod that drew his attention. “The best thing for constipation, is a nice warm soapy enema.” John said quietly as he lowered his hand back down and rested it on Karen’s white bottom. He ran it softly over both of her cheeks and down the back of her legs. “Has anyone ever given you an enema before?” he asked finally, desperately hoping for some sign of acceptance.

“No, never, but I know what they are…are you going to give me one?”, Karen finally answered just as quietly as John had asked the question. She had been reading some family “medical” book when she was a teenager and had come across a chapter on digestive disorders, it had contained a passage on how to give an enema. She had read it, then re-read it many

times, trying to imagine how it would feel to have a tube inserted in her rectum and be held down as warm water was forced into her backside. The thought of being completely naked, laying over a doctor’s lap as he gave her an enema became her fantasy. She had spent many quiet nights laying face down on her bed, a rectal thermometer deeply inserted in her rectum, pinching and pulling at her hard nipples, climaxing quietly as she lay atop a pile of pillows.

John sighed deeply, and reached into the paper bag at his feet and pulled out the small pack of rubber gloves. He snapped them into place and dipped his index finger into the vaseline. He spread Karens cool, white buttocks apart with his left index finger and thumb, before gently placing his right index finger up against her small crinkled anus. He began to circle his finger around her rosebud, lubricating it with the vaseline. He was pleased to feel Karen push back against his finger as he slowly pushed it into her. He slipped it all the way in and held it still, waiting and watching for her reaction.

“Unnhhh…” Karen answered as John entered her rectum. She closed her eyes and gritted her teeth as she felt his finger drive deeper. Her buttocks clamped tightly together and her toes curled up, she began to breath heavily as he finally came to a stop. She slowly began to relax and enjoy his examination. Her buttocks loosened and became soft and pliable again as John began massaging the inside of her rectum, spreading the vaseline in all directions.

John finally pulled his finger from Karen’s bottom only after making sure it was coated completely. He had had to re-apply vaseline to his finger and drive it back into her willing bottom several times before he was sure it would be able to take the enema nozzle. He stripped off the rubber glove and tossed it onto the coffee table before gripping her around her waist and pulling her up to face him. Her face was red, and flushed, he couldn’t tell if it was from his rectal probing or “the bug”, he hoped it was the former.

Karen stood silently as John pulled her panties all the way down and off before dropping them on the floor. She allowed herself to be walked into her bedroom and placed face down upon the bed . She closed her eyes and hugged one of her pillows as she felt John pull her right leg up and bend it so that her bottom cheeks spread apart. “Lay still, Karen” he instructed as he went into the bathroom, the brown grocery bag in one hand. He turned on the faucet to let the water warm up. He extracted the

douche kit he had bought at the drug store, it was one of those common ones with two nozzles, one a small, thin pipe that he tossed immediatley into the garbage, the other one which was longer with a flanged tip was the one he attached to the end of the hose. He filled the bag and loosened the clamp to let the air out. He carried it back into the bedroom and hung it on a hook that was poking out of the wall overlooking her bed.

Karen lay still on the bed waiting for John’s return. With her right leg bent at the knee and pulled up towards her head, her bottom cheeks were spread apart, her anus and vagina lips open to the cool air. She looked through half closed eyes as John returned with the enema bag. She felt him sit down on the edge of the bed and place his hand on her hip. “I’m going to slide the nozzle into you in a minute, it won’t hurt but you’re going to have to lay still..ok?”.

Karen nodded her agreement and obediantly lay still as John placed his hand on her right cheek and felt her cheeks being spread even farther apart. She gasped as the plastic nozzle first poked at her anus then slid in. John held the nozzle firmly in place and reached up to unclamp the hose. “Hold still now Karen”, he spoke as the enema hose stiffened and Karen began to stir as the first warm flow of water entered her.

“Oh…oh…unnhh”, Karen moaned as she felt the warm water begin to enter her rectum and fill her lower bowels. She clasped her hands into fists and began to shudder as her first orgasm began. John clamped the hose shut tightly and pulled Karen’s leg out so that she was laying flat on her belly. His dick strained against his pants as he looked down at Karen laying seductively on the bed, naked from the waist down, the white, flimsy enema hose snaking it’s way from the bag down to her buttocks. “Relax, Karen”, he said gently as he reached one of his hands under her t-shirt and began to massage her breasts.

“Oh..I really need to go to the bathroom John, please let me up”, she spoke with some urgency as the water gurgled within her. Her ass cheeks clenched together tightly, but her nipples stood out hard and firm as John’s warm hand began to run over them. “Not yet Karen, you need to take the entire enema for it to do any good”, he whispered and reached up and unclamped the hose again.

“Ahh….Please John..” Karen cried out as she felt the water begin to flow into her once again. “Lay still Karen”, John ordered sharply, his voice now as firm as his cock. “It’ll be finished soon”, he stated as he glanced up at the bag, now nearly flat. When it was, he clamped the hose again and looked down on Karen . “Lay still for a few minutes”.

“Oh…John….please…” Karen cried as she lay naked under his watchful eyes and climaxed once again. Her anus gripped the enema nozzle tightly as she held the warm water in. It seemed a long time before John helped her up from the bed and walked her into the bathroom. She almost staggered as John walked her to the bathroom. “Bend over a little”, he commanded as she leaned against him. John flipped up the toilet seat and positioned Karen carefully before pulling the enema nozzle from her

bottom. He stood by her side as she plopped down and began to release the water. She looked up at him several times, blushing as the water escaped from her backside making loud farting noises. “Just let it all out Karen” he said softly as he began filling the enema bag again.