This story, my first, is a tribute to Jane Marwood, whose writing I admire very much.
If Jane Marwood reads this story, please send me an email with your thoughts on the story, I’d love to have your feedback. Harrietmarwood@yahoo.dk
The doorbell rang. Upstairs, 14-year-old Billy was sitting in his bedroom reading some old comic books. Ever since his mother had passed away several years before he had been somewhat withdrawn, spending a lot of his time alone in his room. Downstairs, Billy’s father opened the door and welcomed the new babysitter in to their home.
"Welcome Jane, you're just in time, I’m leaving shortly," he said, while glancing at his watch. “Just time to introduce you to Billy and give you a quick tour of the house.”
Billy´s dad was going on a business trip for a month, and even though Billy had complained about being too old for a babysitter, his father had been rather overprotective of him ever since his mother had died, and insisted on the need to have a responsible adult present. Jane Marwood had come highly recommended and she had been available for the entire month.
"Billy is upstairs, let me just call him," he told the babysitter as she entered the house and took of her coat.
She was a beautiful woman in her late twenties, with a stern yet motherly look to her. She radiated a kind of feminine authority, and even Billy’s father noticed. Jane’s thick jet black hair tumbled about her shoulders, framing a face of perfect features, with deep, mesmerising green eyes and soft, red lips. Her figure was slim, yet feminine, with good sized breasts sitting firmly and proudly on her chest, the curve of her waist and hips leading to long, slender legs.
"Billy come down your babysitter is here!" he yelled up the stairs, before taking Jane’s coat. "He is very shy, but he's a good boy, he does as he is told.”
“I’m sure we will get along just fine,” Jane said with a kind smile.
They both heard the sound of soft footsteps, as Billy had left his room immediately and was already walking down the stairs. As he saw the beautiful babysitter who would be in charge of him for the next month, he blushed and looked down at his feet.
"Now Billy, you do everything your nanny tells you without questioning, is that understood?" His father said sternly.
"Yes," Billy said in a low voice as he kept looking at his feet.
"Now Jane you do as you see fit to make sure Billy is healthy and well,” his father said as he picked up his suitcase. “As you know I home school him and I’ve made a list on the refrigerator of the homework he must do while I’m gone. As I say, he’s a very good boy, but should he need disciplining, I shall leave it up to you to decide what form that will take. I’m sure you are quite experienced looking after young boys."
Jane gave only a soft smile and a nod of her head in reply. Billy for his part, blushed a little deeper.
"Now I really should be getting off to the airport,” Billy’s father continued, “here is my phone number and the address of where I will be staying, take care."
Billy's father handed her a note, nodded to Billy, and walked out the door towards the taxi that just arrived for him. As the door closed behind him, the house suddenly became very silent. Jane looked Billy up and down and liked what she saw. He had rich brown hair, with matching eyes and a very handsome face. He was slim built, probably around 5’6”, with a healthy looking body. He had beautiful, almost feminine skin and the blush on his face made him look adorably cute.
"I am Jane Marwood, but you can call me Miss Marwood," the nanny said as she stepped towards Billy and caressed his cheek, making Billy blush even further.
Jane couldn't believe her luck, to have this cute little teen under her control for the next month. But she was going to be gentle with him she thought to herself, take it slowly, for now.
"Yes Miss Marwood," Billy stammered as he looked into her eyes for just a moment before looking down again.
"Now I think I will prepare some lunch sweetie, are you hungry?" she asked as she ran her fingers through his hair, the simple act of her touch toying with his emotions.
"A little Miss Marwood," Billy said, overwhelmed by her care, no one had spoken to him so gently like that since his mother died.
"I will make you something really nice for being such a polite little boy," she said while caressing him. "As long as you do as I say we are going to get along just fine," she said before kissing him on the cheek and walking out into the kitchen.
A single tear formed in Billy´s eye as she walked away, she reminded him of his mother.
Jane had Billy take her bags up to her bedroom as she prepared his lunch. As Billy ate Jane took her time to study him closer. She couldn't wait to see what was underneath his clothes. He is probably a virgin, she thought to herself.
“So do you have a girlfriend Billy?" Jane asked trying to hide the excitement in her voice.
"No Miss Marwood," Billy answered, a blush spreading across his face.
"Have you ever had a girlfriend?" Jane was now stroking his hair again as she sat next to him at the dinner table.
"Eh.. no.. Miss Marwood," He stammered his face red from embarrassment.
"Surely not, you’re such a sweet boy," she said softly, a broad smile spreading across her face. "I think it´s time for your evening bath sweetie," Jane continued, enjoying the shock on Billy's face.
"Wh..what?" He stammered as he quickly looked up into her face.
"Evening bath I said! And I will have no nonsense or I will call your father at once, I’m sure he won't be pleased at all!" Jane said in a stern tone.
Billy looked down onto his plate "No Miss.. yes Miss.. sorry Miss," he mumbled, tears forming in his eyes.
"That's better, now go upstairs into the bathroom and fill up the bathtub,” she said. “I will be up shortly."
Billy quickly walked upstairs as Jane cleaned the dishes with a satisfied smile on her face.
As Jane entered the bathroom Billy was standing next to the large bathtub which was already filled. Jane sat down on the closed toilet seat and motioned Billy to come stand between her legs. Jane spoke softly again,
"Now just be a good little boy and I will be nice to you, okay sweetie?"
Billy nodded. Without further ado she took the hem of his shirt and lifted it upwards,
"Lift up your arms sweetie," she said as she slowly took off his shirt.
Then she untied the lace on his shorts and drew them down past his knees leaving him in just his simple white underpants. Billy was shaking and his face was red with utter embarrassment. Jane placed her hands on his hips and looked up into his face.
"Just relax sweetie, no reason to be shy, you have nothing I haven’t seen before. Is this the first time someone has seen you naked?" she asked, her heart pumping with excitement.
"O..Only m..my mother when I was little," Billy stammered trying to avoid her gaze.
"Well you better get used to it sweetie because I’m going to be taking care of you," Jane said softly as she placed her fingers on the waistband of his underwear. “From now on I will be undressing, bathing and examining your most intimate places.” Jane spoke softly with a gentle smile on her face. “You can’t afford false modesty baby.”
Slowly she pulled his underwear down, revealing a nicely sized penis with a nice pink glans and, to her delight, only very little pubic hair. She pulled the garment to his feet and made him step out of them. The rest of his body seemed to be completely hairless.
Billy quickly placed his hands on his genitals to try and hide himself, which she found very cute. I will let him have a little modesty for now, she thought to herself as she placed her hands on his hips and turned him around, admiring his cute, smooth little bottom. Jane licked her lips as she slowly let her hands slide down over the soft flesh of his bum.
"That´s a good boy now step into the bath sweetie," She said as she gave him a gentle slap on his butt.
Jane went over to the bathroom table to open the bag she had brought along and picked up some hair-removal cream. She quickly looked inside the bag and made sure she had remembered everything.
She walked back over to the blushing boy in the bathtub. His hands still grasping his genitals tightly and bending slightly forward. His innocent face looking up at her, he looked very embarrassed, and so very cute.
Jane's mind was split in two. One part of her wanted to take him in her arms and comfort him, gently stroking his hair and whispering soothing things in his ear. The other part of her wanted to bind his wrist behind his back and force him into a humiliating position with his little bottom on display, to own every inch of him completely. This combination of feelings aroused Jane beyond belief, she licked her lips and spoke gently to the boy.
"Hands away now sweetie, I need to remove all that nasty hair; healthy little boys should be completely bare at all times."
Billy blushed furiously at her words, but didn't dare to disobey her. Slowly he removed his hands, revealing much to his dismay, that his penis had become slightly engorged. A smile spread across Jane's face as she slowly spread the hair-removal cream over his crotch, making sure to cover the entire area. After a couple of minutes she proceeded to wash of the cream, exposing his now smooth bare genitals and pubis to her gaze.
"Hmm, that’s better sweetie, Mistress likes you this way, and you want to make Mistress happy don't you?" As she finished her sentence she squeezed his testicles firmly, causing Billy to jump in slight pain.
"Yes Mistress," Billy whimpered, utterly embarrassed that his penis had now become fully erect, a fact that Jane noted with a satisfied glance.
"Now let's get you cleaned shall we?" Jane said as she began to lather up her hands with soap.
She went down on one knee and started gently washing up his legs, stroking the insides of his thigh. As she came up further she skipped his bottom and began washing his back instead; she would be saving the best part for last. Billy seemed very relieved that she did, not having any idea what was in store for him. Jane proceeded to wash his upper body, running her fingers down his stomach stopping just above his now throbbing erection.
"I need to wash your hair darling, just sit down in the tub with your back facing me.”
Billy awkwardly sat down in the bathtub, happy to hide his erection from her gaze. Jane gently washed his hair, running her fingers down his neck.
"Such a good boy," she whispered as she massaged his scalp. She could feel Billy start to relax in her gentle hands.
"See sweetie? As long as you behave I’ll be nice to you," she whispered right into his ear before kissing him on the cheek. "Now get on your hands and knees so I can rinse your hair, with your bottom facing me."
Billy leant forward onto his hands well aware that his bum was now nicely on display.
"Get your head down in the water sweetie,” Jane said as she gently pushed down on the back of his neck, while she admired his little tushy. She leant over his back, as she rinsed his hair, her pelvis pressing against the soft globes of his buttocks.
“Close your eyes sweetie I don’t want my poor baby to get soap in his eyes.”
When she was done rinsing his hair she pulled out the plug on the bath, and went over to the sink to fill a minor bucket with warm water and soap. The reason she emptied the tub, was so that his face could go all the way down to the floor of the bathtub, raising his bum up nice and high for her pleasure. She walked back over to Billy and pressed down on his shoulders.
"All the way down, and arch your back, that's a good boy."
Billy had never felt so humiliated as he gave her a perfect view of his bare behind and his stiff member dangling between his legs.
Just as he thought it could not get any worse he heard Jane’s voice again,
"Now reach behind yourself and spread those cheeks nice and wide for me sweetie, I need to clean you thoroughly, no nonsense now."
Billy's face was red with embarrassment. He could hardly believe what he had just heard. With trembling hands he reached behind himself and spread his buttocks wide for her. Jane took a deep breath as the treasure between the two round globes was exposed to her gaze. A deep smooth cleft, and a tiny light pink anus, contracting from the cool air in the room, making it wink at her. She could hardly believe her luck, such a cute little virgin rosebud, and she could do with it whatever she wanted. The very thought of it made her wet as she just stared at his opening for several seconds.
"What a pretty little anus you have baby," She said as she lathered up her hands and ran them down the smooth cleft of his bottom, down between his legs and cupping his firm balls, before lathering up his throbbing member, making him squirm as she ran her nails gently across the glans.
"Your little hole looks very tight sweetie, so just relax as I pop my finger up that little tushy of yours."
Billy felt utterly defeated as he tried to relax, awaiting the impalement of her finger. Jane ran her finger around the edge of his sensitive anus, teasing the puckered rose as it contracted violently at her touch.
"Just relaaaaaaaax, let me have your little bottom," she whispered softly as she pressed the tip of her finger into him making Billy whimper.
"Ohh, please don't miss," his soft pleas only turning her on even more.
"Baby, you are very tight back here, actually too tight in my opinion," she said as she slowly pressed her finger into him past her knuckle. "In my experience as a nurse, healthy little boys should be able to take a finger up their bottoms without any problem, this could get very serious later in life."
"It can?" Billy whimpered as he tried to look up at her past his shoulder, a nervous expression on his face.
"Yes it most certainly can, I think we have to dilate it a little while I’m looking after you," Jane said with a smirk on her face, hardly able to believe how naive this poor boy was.
"Aww, uhh ooh" Billy whimpered softly against the floor of the tub as her finger was pressed all the way inside him, his anus gripping tightly around her finger, as she slowly roamed inside him, feeling his prostate gland. Billy felt humiliated beyond believe to have this beautiful woman casually play with the most intimate part of his body. Yet his penis was painfully erect, his body betraying him.
Suddenly he heard a ‘pop’ as Jane pulled her finger from his behind. It even sounds cute, Jane thought to herself with a smile as she walked towards her bag once again.
"I’m going to give you an enema dear, a healthy little bottom should be sparkling clean at all times," she said as she started to fill the enema bag with warm water and soap, making sure the temperature was just right.
"An...an enema?" Billy stammered, still pressing his face against the cool bathtub and spreading his cheeks wide, not daring to get up from the degrading position.
"You will learn what that is soon enough, the only thing you have to concentrate on is to relax that little bum like a good boy, and accept whatever I do to it, understood?" Jane said sternly as she chose a medium size enema-nozzle and lubed it with her slender fingers.
"Yes Miss Marwood," Billy said in a low voice, knowing she had complete control over him.
"That's a good boy, as long as you remember that, I will give you all the care and affection you need." Jane was amazed at how submissive this boy was, still laying face down with his rosy anus on display, looking back at her with those big brown eyes.
She walked up behind him and pressed the tip of the nozzle against his tight opening, making him whimper again.
"Sssssshhhhhhhhh, relaaaax, you can let go of your bum-cheeks now sweetie," she said as she forced the tube up inside him. Billy felt completely overwhelmed by the invading nozzle, yet he could do nothing but accept the penetration of his virgin anus.
"I’m going to fill your bottom with warm soapy water sweetie, it might feel a bit uncomfortable, but I made the temperature nice and warm for you." As the nozzle was in place, she started emptying the bag, warm soapy water running into Billy bowels.
"Uhhhh ohh, no... Miss," Billy was beside himself from the strange unknown feeling of being filled this way, and from the acute embarrassment.
Jane hung up the enema bag and leaned forward placing her soft hand on his neck, softly and lovingly caressing him as she placed a tender kiss on his cheek.
"Halfway through baby, then you little bottom is going to be sparkling clean, just like your nanny likes it," she whispered into his ear.
She got up and sat on the side of the tub gently rubbing his stomach, tracing her fingers down to his still hard penis, gently stroking it, making Billy moan from pleasure and humiliation.
"Oh there we are sweetie, now you just have to hold it for five minutes. So be a good boy and clench tight," Jane said after the bag was emptied. She pulled the nozzle from his butt, once again sounding a loud ‘pop’, making Jane giggle softly and Billy blush a deep red.
After five minutes of Billy pleading to empty himself, Jane placed her hand upon Billy's left cheek making him quiver.
"Let's get you on the toilet and empty you out sweetie."
Billy got up clumsily as Jane took his wrist, guiding him over to the toilet and made him sit down with his legs wide apart.
Billy blushed deep red as he realised his penis was sticking straight up towards the ceiling.
"Come on now, just let it go sweetie."
Billy felt utterly humiliated that she was watching him, but the pressure had become too much. Despite his embarrassment he soon evacuated his water-filled bowels into the toilet.
Billy looked down in embarrassment not able to meet her gaze. All the while Jane was stroking his hair telling him what a good little boy he was. When she was sure that he had emptied himself completely of water she flushed the toilet and told him to turn around and sit backwards on the toilet so she could wipe his bottom.
Blushing a deep shade a red, Billy slowly got into position, barely able to believe how utterly humiliating this was. Jane pressed down on his back making him lean forward, resting his head on the toilet and arching his back.
Jane smiled wickedly at her invention as she picked up some sheets of soft toilet paper and folded it in her hands. All the soap and water had left everything clean but she loved how it embarrassed the poor boy to have his bottom wiped like a child.
She brought her hand down between his cheeks and slowly pressed the soft material against his cleft, splitting his buttocks as she wiped it over his sensitive anus, leaving only water on the tissue. Jane lovingly stroked his back as she repeated the procedure several times, each time making Billy whimper as the tissue touched his opening.
"Such a good boy, from now on I’ll be wiping your little behind," she whispered into his ear.
Jane was no longer holding toilet tissue in her hand but was simply running her fingers up and down between his cheeks, enjoying his utter humiliation. She made him get up and pulled him over to the shower, quickly soaped him up and sprayed him of with cold water, making him whimper as the cold spray touched his flesh. Jane turned off the shower and walked out of the bathroom.
Going into her assigned bedroom, she picked up a pink fluffy towel that she had brought along and returned to the bathroom. Billy was still standing in the shower when she walked in, his erection had subsided, and shivering with cold he hugged himself, looking at her with pleading eyes, like a frightened puppy.
Jane felt a rush of sympathy for him.
“Come out of the shower so we can get you dried you poor thing,” she said in a soft voice.
With clasping teeth, Billy walked over to Jane with his head hung low in shame. Jane wrapped him in the fluffy towel and hugged him tight, his face pressed against her warm bosom as she stroked his back through the towel.
"Oh you're freezing, you poor thing," Jane said as she lovingly kissed his forehead.
"You were such a good boy for your nanny, I’m very proud of you."
Billy felt absolutely ashamed and embarrassed, yet he felt so loved. He closed his eyes and felt her warm body against his.
When he was starting to become warm again, Jane pulled the towel from his body, making him blush. She proceeded to dry him thoroughly paying special attention to his smooth genitals and making him bend over and touch his toes so she could dry between the soft globes of his behind, ignoring his pleas of embarrassment.
Reaching into her bag she picked up a pair of short white underpants and nightshirt. She helped him step into the undies and pulled them up tight around his bottom, giggling at the little red heart on the back of them, which he didn't notice. She made him lift up his arms as she helped him into the nightshirt.
"Now you go read some of your homework, I will call when dinner is ready," she said as she gave his soft bottom a hard squeeze, making him jump.
For dinner, Jane had brought some Freeze Dried Space Food. The point of which was that the consumption is high and leaves almost no waste, telling Billy she was putting him on a new diet to help keep his little bottom nice and clean. When Billy had finished eating she told him to brush his teeth and get ready for bed, then lay flat down on his stomach in his bed, and wait for her to come up.
As Jane entered his bedroom 10 minutes later he was on his stomach resting his head on the back of his hands, which were laid out in front of him. Billy looked back at her nervously as the sound of her high-heels came closer. Jane smiled softly down at him as she stood by the side of the bed. In her hand she carried a jar of moisturising cream.
She bent down and kissed his cheek "I’m just going to rub some soothing cream on that little bottom of yours sweetie," she said, making Billy blush.
"Yes nanny,” was all Billy could reply.
Jane took a large pillow and sat beside him on the bed.
"Raise your cute bum for me," Jane said as she brought it underneath him, elevating his bottom nice and high.
She made him spread his legs as she got up behind him, stroking his back down to his undies, hooking her fingers into them shortly before stroking up his back again, making Billy shake each time from the humiliating thought of having his bottom bared once again. It didn't pass by Jane unnoticed, she found it ever so cute that Billy was so concerned about her seeing his behind, it made her want it even more.
Jane smiled at Billy's reaction as she pressed her finger down on the heart on the back of his undies, touching his anus through the material and making him squirm.
"Let's have these of so I can get proper access to this little rump," she suddenly said as she hooked both hands into the waistband and slowly pulled them down, admiring the soft yet firm flesh that came into view.
"Please no Misstress," Billy stammered beside himself with embarrassment as he pressed his face into the pillows in front of him. She pulled them all the way of his legs, and folded them neatly besides his face.
She poured a generous amount of cream into her hand and then proceeded to rub it all over his bottom, spreading his cheeks to get in deep in his cleft. Billy groaned into the pillow from the embarrassment, of having her handle him so intimately. To Billy’s further embarrassment his penis had become hard, and was pressing against the soft pillow beneath him.
Jane was now running her finger around the rim of his sensitive little sphincter, while telling him what a good little boy he was being. She was mesmerised by the small pink rosebud as it kept winking at her seductively. She pressed her finger slowly into it, making Billy groan with the humiliation.
"Now relax your tiny anal rose, I just need to feel around a bit sweetie pie," she whispered softly, pressing her finger firmly inside of him.
She traced her other hand down his cleft feeling his perineum and tight ball sack. She noticed his hard member and quickly removed the pillow from underneath him causing Billy to try and lower himself onto the mattress.
"No you don't! Keep that bottom up high!" Jane said sternly as she brought her hand down hard upon his right buttock making Billy flinch in pain. SMACK SMACK SMACK!
"Owwww please Mistress, I’ll be a good boy!" Billy cried out in pain.
He lifted his bottom as high as he could, aching his back violently and pressing his face deep into the mattress, hoping it would stop her beating, and it did. Jane slowly lowered her hand softly smoothing her hand across his now rosy red buttocks.
"Please don't be mad Mistress," Billy sobbed softly into the bed.
"Shhhhhhh I’m not mad baby, don't cry," Jane said as she once again rubbed her hands with cream on ran them across his flesh. "Now what do we have here?" She said as she ran her fingers down between his legs, grabbing his rigid member.
"Uhhh," Billy whimpered as she slowly jerked his sensitive member.
"Little boys never seem to be able to control themselves, now just relax as I milk your little friend," Jane said while she expertly manipulating his penis, making him moan in pleasure and embarrassment.
She brought up her other hand to his anus and quickly pressed a lubed finger up inside him, as he jumped from the shock and the intense feeling.
"Ohhh, please noooo Miss," Billy whimpered, but to no use, Jane was enjoying herself too much as she milked the poor boy.
Jane then suddenly grabbed his hips and turned him around onto his back and lifted up his legs, bringing his knees up to his chest. She then grabbed both ankles in one hand and pressed them backwards, lifting his bottom up from the bed, as if he was a baby about to be changed.
She looked deep into his frightened eyes while milking him slowly with her other hand. She let go of his throbbing member and traced her finger down to his exposed anus, running her finger around the rim.
"That's a good little boy, all open for your nanny," she whispered as she gently but firmly pressed her finger up his tight opening, twisting and turning her finger deep within him.
Billy turned his head to the side, wanting to escape his acute humiliation. As she located his prostate she pulled out only to add another finger, stretching his poor bottom.
"Please.. no.. Miss Marwood," He whimpered as she roamed freely inside him, skillfully manipulating the virgin boy. His penis was throbbing violently, begging for release.
When Jane decided to end his torment, she slowly pulled out her fingers, watching his pink anus close up tightly behind them.
"Hold your knees tightly against your chest!" She ordered him as she sat down beside him.
Billy hugged his knees tightly and closed his eyes, not knowing what to do with himself. Jane leaned over his face, wanting to see every expression of his humiliation.
"Look at me," Jane said as she leaned closer kissing him deeply.
Billy moaned into her mouth as she invaded him with her tongue, her hand once again finding his throbbing penis. Slowly she pulled back the skin, her fingernails softly tracing over the tip of his penis. She gently cupped his testicles squeezing them tightly bringing him over the edge.
Jane quickly took one of the soft pillows and laid it under his erupting penis, gently pointing his member into the soft material as he burst out streams of thick semen. His head tilted backwards, groaning from the intense sensation in his body. As she extracted the last drop of fluid from his body, she traced a finger down to his sensitive anus making Billy flinch.
With a giggle Jane threw the soiled pillow on the ground and grabbed the undies from beside him. With Billy still hugging his legs, she carefully slipped on his undies pulling them up tight around his bottom, making sure his penis was settled in comfortably. She pulled the bedcovers over him and tugged him in, before arranging his pillows underneath his head.
"You were a very good boy today Billy," she said as she caressed his cheek, looking deep into his tear-strained, blushing face.
As he looked at her with those big eyes she could see his affection for her, that he needed her love and care. Softly she gave him a kiss on his lips before turning out the lights and leaving the room.
As Jane lay down in her bed she started touching herself thinking of the day’s events, and her charge’s young firm body. She came harder that night than she had in a long time.
The next morning as the sun shined in through the windows in Billy's room, Jane carefully opening his door and walked over to him. He was still laying the same way as she left him last night, tucked in tightly. She placed the glass of juice she had prepared on the table and slowly sat down on the edge of the bed. Leaning forward she brushed his hair away from his forehead, looking into his handsome face.
"Morning sweetie did you sleep well?" she whispered softly as Billy slowly opened his eyes, looking up at her innocently.
She brought the glass of juice to his lips, smiling down at him.
"Thank you Miss Marwood," Billy said genuinely as he gave her a little smile. He quickly drank it while Jane rubbed his forehead, running today’s program through in her head.
"You seem a little warm, maybe you have a fever baby," Jane said, sounding concerned.
"I feel fine nanny," Billy said looking back up at her, starting to become concerned as well.
"Well we better check to make sure sweetie, I'll be right back."
Not knowing what she meant, Billy drank the rest of his juice and sat up in the bed. When Jane returned she was carrying a rectal thermometer and a jar of Vaseline. Billy's face became a picture of anxiety as he saw what she carried in her hands. Jane picked up a chair and sat it next to the bed before sitting down on it.
"Don't worry sweetie, it's for your own good. Now come lay across my lap" she said with a soft smile as she noticed the worried expression on Billy's face.
"Please miss, I’m too old for that!"
Billy quickly stopped talking and slowly got up from the bed with a sigh as he saw her gently loving face turn into a stern expression. With his head hung low he walked over to her and awkwardly lay across her lap, his underwear-clad bottom sticking right up at her. With a wicked smile she lifted his nightshirt and pulled it down to his shoulders.
Taking a deep breath, she once against hooked her fingers into the undies, this time pulling them down to his knees, causing Billy to whimper with embarrassment. Licking her lips she slowly dug her fingers into the deep cleft of his bottom, pulling the cheeks apart to reveal his puckered little star.
Without saying a word she gently smeared a glob of Vaseline on his anus, making him squirm before she dipped the thermometer into the jar. With one hand she spread his cheeks while she guided the thermometer down to his opening with the other. After tracing the tip of it around the rim of his anus for a moment, she finally pushed it in.
"Uhhhh," Billy groaned as she pushed the whole length of the thermometer up his bottom leaving only the red bulb outside. She could feel his penis becoming engorged between her thighs, as her soft skin brushed up against his dangling member.
With an amused expression on her face, Jane continued to rotate and move the thermometer in and out of him causing him great embarrassment. She then proceeded to pull the thermometer all the way out of him, only to push it right back in again, completely defeating the purpose.
Billy just kept his head down, whimpering each time she moved the thermometer. My God, he's so naive and innocent, Jane thought to herself, as she rotated it inside him one last time before removing it.
"Everything seems fine dear, you're just very tight back here that’s all. But we'll do something about that soon enough baby," Jane said as she wiped off the thermometer and screwed back on the lid of the Vaseline jar.
She then removed a small camera from her pocket, a smile spreading across her face.
"I want to be able to follow your process sweetie, so reach behind yourself and spread those lovely cheeks so I can get a good picture of you back here."
She said, smiling broadly as she felt his body stiffen from the unreasonable demand. Nothing happened for a few seconds, not before Jane placed the flat of her palm on his right cheek as a warning.
"Be a good boy now Billy," she said, hardly able to disguise the excitement in her voice.
A second later Billy gave a big sigh before reaching back, and spreading his buttocks wide for Jane to see.
"Now relax, I need a good picture of that little cute dimple of yours," Jane said bringing the camera up to her face.
‘Click click click’, Billy heard as Jane snapped away, perpetuating his humiliation.
"Such a pretty little hole you have," she said, squeezing her legs together around his penis, feeling him becoming fully erect.
When Jane was satisfied she put the camera away and pulled his undies back in place, before sitting him up in her lap facing sideways. She saw he had tears in his eyes, and she pulled him close, stroking his back,
"Shhhh, don't worry Billy, no one is going to see those pictures but me," she lied as she cupped his stiff member through his undies.
After comforting him for a bit he started to relax as she held him close, whispering kind words in his ears. 15 minutes later, she took him by the hand and led him into the bathroom, giving him two thorough enemas, both of which were all clear. Then she gave him a long soothing bath, gently stroking his body.
Once again she dried him of in a soft towel and rubbed his body in body-lotion before laying him down on the bathmat and applying talcum powder to his genitals. Then she lifted his legs up high, holding his feet together with one hand and applying a generous amount of powder on his backside.
All the while Billy didn't say a word. Other than a few whimpers of embarrassment, he obeyed her blindly. Looking at her with those big brown eyes, he let her do whatever she wanted, humiliating him beyond belief, yet making him feel loved and cared for.
She put him into a clean pair of undies and a thin sleeveless shirt. Then she took him to the living room and told him to take a nice nap on the couch. She pulled a blanket over him and gave him a kiss on his lips.
"Get some sleep," Jane said as she left the room and went up to her bedroom.
As Billy was drifting into a deep sleep, Jane took a shower and pampered herself, looking absolutely stunning as she went to put on her strap-on harness, trying to make up her mind on which dildo she would use to deflower his virgin bottom.
She ended up choosing a rather large one, knowing she would have to take it slow.
As Billy awoke an hour later, Jane was standing over him stroking his hair. He was mesmerized at her beauty as she smiled down at him. She was only wearing a black top and the strap-on harness with the attached dildo. A terrified look spread across Billy's face as he saw the large dildo between her legs, looking back up at her with pleading eyes.
"Shhhhhh, relax sweetie, I’m going to take good care you, we just need to stretch that cute little bottom of yours. Now you want to be a good little boy for your nanny don't you?"
"Yes Miss Marwood," Billy stammered.
"Good then just do as I say and everything is going to be just fine, trust me."
The fireplace was lit and the temperature in the room was nice and cosy. Taking Billy’s hand she raised him onto his feet, lifting his arms so she could pull of his shirt. She then took his hands and placed them on the back of his head. She looked deep into his eyes as she traced her hands down his back, softly squeezing his bum through the thin material of his undies.
To have such a handsome boy at her mercy excited her beyond belief, and she could do with him whatever she wanted.
His lower lip was quivering as he looked down upon his feet, avoiding her gaze. She got behind him and sat down on the couch, hooking her fingers into his waistband she slowly pulled down his undies, letting them drop onto the floor around his ankles leaving him completely exposed in the large room.
"Such a cute little behind," she said as she held him by his slim waist standing back up again. She softly blew hot air on the back of his neck, sending shivers through his body.
"Now go over to the fireplace and get on your hands and knees, face down, bottom up high."
With his feet restricted from the briefs around his ankles, he waddled pathetically over to the warm fireplace and got into position. He wanted to be a good boy for her. He looked back at her, knowing what she wanted from him. Without being commanded, he slowly reached back and spread his soft cheeks wide, offering her his pink virgin rosebud. Jane saw a single tear run down his cheek, he was scared.
"Ohh you're such a good sweet little boy," she said as she knelt down behind him stroking his back gently.
Jane could see his penis throbbing violently between his legs. She picked up her favourite lube from the table and smeared a handful lube up and down the length of her large shaft. Then she applied lube on two of her fingers, and tenderly proceeded to lube up his tiny anus.
"Please be gentle Mistress," Billy whimpered in a low voice.