titjobmaster
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NOTE: This is a fictional tale and all characters depicted are 18+. This is my first attempt at writing a story so any feedback would be appreciated.
~~~~~~~~~~~
Sarah sighed heavily as she relucantly got out of bed. She had put today off for a long time, but she knew that it just couldn't wait any longer. When she had decided to home-school her son James 11 years ago, she hadn't appreciated that some topics would be rather uncomfortable to cover. Back then it was all basic Mathematics, English, Geography, History...the fun and easy stuff! But now, not so much.
Sarah was a single mother in her mid-40s. Her divorce left her very financially secure, so when her only son James was being horrendously bullied at the boarding school he was being sent to, it felt like the right decision to home-school him. Sarah was, after all, a very intelligent woman in her own right and living on her own wasn't what she wanted. She could spend a lot more quality time with James this way and parent him without the interference of her ex-husband or the influence of others.
The beauty of her youth was still very evident in motherhood. Standing 5ft 9, she had an enviable hourglass figure with surprisingly large 34G natural breasts, a slender tummy, delightfully wide hips and peachy bottom. Her long brunette hair was waist length, she had piercing blue eyes and slightly mousy facial features. She was not lacking attention since her divorce but had never sought another man's company.
James, on the other hand, had not yet bloomed and puberty was still a bit of a work-in-progress for him. Still only 5ft 4, James was slender and slight with curly, light brown hair, a larger than average nose and freckles. His one redeeming feature was his bright blue eyes, which he inherited from his mother. He was a timid boy who preferred being on his computer to being outside, but he was polite, helpful and loving. The relationship between Sarah and James was a close one, with Sarah providing the structure, love and guidance that James needed but also acting as a figure of authority when required.
~~~~~~~~~~~
Sarah knew that - as a parent - she should have had "the chat" with James years ago, but as his teacher there really was no good excuse for not having covered Sex Education with him before now. It just made her feel really uncomfortable so she had convinced herself that it simply didn't need to happen, especially as James wasn't necessarily acting like a typical teenager. But that excuse had long since run its course. She could no longer ignore the involuntary glances he would give her chest when she wore a tank top without a bra, or the curious looks he gave on the occasions he would see Sarah in her underwear whilst getting dressed, nor the little tent in his pjs he would sometimes get in the morning. What was most concerning of all were the Google searches she found on their shared iPad. In and amongst all of the gaming and other harmless content were searches like...
"Average penis size"
"Big boobs"
"What do boobs feel like?"
"What size should my penis be?"
All of these were a clear sign of a boy who was developing certain feelings, interests and concerns but wasn't being given the right information and assurances to be able to manage those feelings appropriately. And it was all her fault. She should have been the one to answer those questions. As uncomfortable as it made her feel, she was responsible for her son feeling lost.
No, the time was now. Today. It had to be. It was the right thing to do. Sarah had sought help on places like Mumsnet but everyone had a different opinion on the subject. Also, not being a qualified teacher herself, she had no access to official Sex Education material. She had decided to do her best, put on a brave face and hope that everything would work out. She had planned it out in her head, up until a point, then was just going to wing it! The key was to try to hide her feelings of embarrassment, be informative and try to get James to open up to her so she could guide the conversation in the right direction.
~~~~~~~~~~~
It was a gloriously, sunny Friday morning and Sarah dressed appropriately in a light floral V-necked yellow Summer dress which rested just above her knees and did its best to contain her heavy, full chest. Underneath she wore her favourite, well-supported white plunge bra and a matching white thong. As she put on her sandals, she steadied herself ready to face the day then headed downstairs to make breakfast.
As she walked downstairs she could already hear the TV on in the lounge meaning James was up and about - a good start. Sarah headed into the kitchen and began busying herself with making toast and putting out a selection of spreads on the table.
"James! Breakfast's ready!" She called, as she poured them some orange juice. James walked into the room still wearing his loose fitting Batman pajamas and sat down at the table. Whilst Sarah found it adorable that her little boy still liked to wear superhero pajamas, she knew that she really should buy him something a little more mature soon.
"Morning Mum!" James said, as she grabbed himself some toast. "Did you sleep well?".
"Yes, thanks sweetie." Sarah replied, not entirely truthfully. "It looks like you did too! It's nearly half past eight. We've got a lot to get done today and you're not even washed or dressed yet."
James frowned slightly and looked over to the Weekly School Schedule attached to the fridge to see what the timetable was for today.
9am-10am: Mathematics
10am-10.30am: Geography Revision
10.30am-11am: Break
11am onwards: Miscellaneous
"Miscellaneous? What's that, Mum?" James asked curiously as he looked back at Sarah.
"Never you mind, young man. We'll talk about that later. But you've got half an hour to get up those stairs, shower, get dressed and be back down at this kitchen table with all your books." Sarah said this in a slightly more authoritative tone than she intended, probably to mask how nervous she felt, so she gave James a reassuring smile before adding, "Go on, love. Off you go!".
As James disappeared upstairs still chewing his last mouthful of toast, Sarah leant back against the kitchen side and steadied her breathing. She could feel her elevated heart rate, slightly faster breathing and a nervous knot in her stomach. "Pull yourself together!", she thought to herself. "Today is about James, not about you. You've got a plan. It's going to be fine." She closed her eyes for a brief moment, gathered herself together, and began clearing the table ready for the start of lessons.
~~~~~~~~~~~
James got out of the shower, towel-dried his hair then wrapped then towel around his slender waist as he walked into his bedroom to get dressed. His bedroom was well kept as always, with the exception of a half built Star Wars Lego model in the corner with the box and random bags of pieces neatly ordered in a row. He'd finish that off later; the perfect Friday night! His PC sat on his desk in the back right of the room and his bed was on the other side of that. He walked over to his chest of drawers and pulled out a fresh pair of white y-fronts and some Darth Vader socks, then took a pair of beige shorts and a tshirt out of his wardrobe. He then let the towel drop to the floor as he prepared to get dressed. He caught sight of himself in his mirror and sighed. He was still so short and skinny for his age. He only had one or two tufts of light wispy hair on his chest and his genitals were still hairless and soft-skinned. His balls sat tightly in his coin purse and his penis - or "willy" as Mum called it - was still the small size as it had been for years. He measured it once after hearing the boys at school talking about theres and that had only lead to disappointment, as had Googling the average penis size. His was quite a bit below that.
Putting that to the back of his mind, James pulled up his pants and began to get dressed. Curiousity was the main thing that filled his mind now. "Miscellaneous....I wonder what that could mean", he thought to himself. "Last time that was on the timetable we went on a fieldtrip to the Welsh seaside near Tenby to see examples of coastal erosion. Maybe it's another field trip!". Whilst that could be fun, James wasn't a massive fan of surprises and the thought of the unknown made him feel a little uneasy. Mum also acted a little weirdly when he asked her about it earlier, which made him a little suspicious. Now fully dressed, he gathered his books and headed downstairs to begin the day.
~~~~~~~~~~~
"How are you getting on with those Differentiations and Integrations, sweetie?"
"I'm....done!" said James, with a smile on his face. "You're going to have to step your game up, Mum. Those were too easy!".
James passed Sarah his workings for her inspection. Sarah had just set James a load of questions this morning rather than teaching him anything new. She just wasn't in the right headspace to cover new content as her mind was very pre-occupied with what was still to come. She looked over the immaculate work and gave James a warm, encouraging smile.
"Good boy. Perfect as usual - my little mathematician!". Sarah glanced up at the clock. 9.57am. "Why don't you clear all of this away and start your Geography revision? I've just got to pop to the shops and I may not be back until you've started your break."
"Oh...ok, sure. What are you getting?"
"Nothing exciting." Sarah replied as she grabbed her handbag and car keys. "Just a few bits. Now you focus on that revision, young man. I'll know if you've not done it!". She gave James a smile and a playful wink as she walked out the front door, clearly indicating that she trusted him implicity and knew he would never dream of not doing his work just because she wasn't there.
~~~~~~~~~~~
As Sarah parked up at the Supermarket she took a deep, steadying breath which caused her large chest to strain against the confines of her dress. The knot of anxiety in her stomach was getting worse. What she had thought about and planned for weeks was finally becoming a reality. Not letting her resolve waver, she got out of the car and walked confidently into the shop.
Knowing exactly what she needed, Sarah headed straight for the Fruit & Veg aisle. With her basket in one hand, she walked over to the cucumbers and picked up the nearest one. It was long, thick and mostly straight - perfect for representing a penis! It was almost in her basket before she paused. Something she had read on Mumsnet suddenly came into her mind, along with the memory of some of James's online searches. What if, as she suspected, James was somewhat below average in the willy department? She didn't want him to feel intimidated or shamed during their lesson; that would be a disaster! She put the cucumber back and started to wonder up the aisle. Ahh, what about these? She picked up a bunch of small bananas. They were a little curved but much thinner than the cucumber and only 4-5 inches in length. Far more appropriate! They went straight into her basket before she headed over to the Pharmacy aisle.
At this point, Sarah looked around a little nervously as if worried she was going to be seen doing something wrong or recognised by someone she knew. After confirming the coast was clear, she walked towards the selection of condoms on offer. She immediately discounted all of the extra large, flavoured and ribbed ones - they would be of no use! Next were just a choice of regular condoms but right at the end was what she was after. According to the box they were a "Trim" size and ideal for men who "do not need it very wide". Whilst the thought of her son filling one of these condoms made her uncomfortable, she grabbed the box and headed straight for the self-service machine to pay to avoid any unwanted interactions.
~~~~~~~~~~~
James was in his bedroom with his curtains draw and headset on playing one of his games. Gaming provided him with the ultimate escape and it was the best way he knew to make him forget his anxieties like the feelings of apprehension he had about the rest of the day. He looked at his watch which read 10.51am, then he heard the door click open. Mum was home! There wasn't long left of his break so he decided he was going to go downstairs early and find out what was going on. He exited his game, took off his headset and drew the curtains back so sunlight flooded his bedroom. As he headed downstairs he called "Hey Mum!" to find out where she was, but the rustling noises in the kitchen answered that question for him.
As he walked into the kitchen, his Mum was standing there waiting for him holding a shopping bag. The kitchen table was cleared of all books. She smiled at him.
"Hello sweetheart. Why don't you sit down?". This wasn't so much an invitation as a kind instruction, which he habitually obeyed but with some apprehension. Normally when she spoke to him like this were on the very rare occasions that he got in trouble. What could he have done wrong? As he sat down he watched as Sarah walked over to the blinds and drew them slightly so sunlight was still coming in but he wouldn't see out into the garden. She walked back over to him, her chest bouncing slightly in her dress as she did so, sat down opposite him and put the shopping bag on the seat next to her out of sight.
"What's in the b-"
"Honey." She cut across him before he could finish his question. "I want to talk to you about something a little different this morning, but I'm going to need you to be the good, mature boy I know you can be. I want you to listen carefully and engage with me. I also want you to not be afraid to ask me questions. No question is a silly question and I promise I won't be angry at anything you say. You can tell me anything, sweetheart. Do you understand me?"
"Umm...yes, Mum. I understand." James nodded politely, feeling nervous.
"Good boy." She pauses for a moment and takes a deep breath, her heavy bosom rising and falling. "Today I want to talk to you about sex."
A silence fell over the kitchen as James just stared at his mother whilst his stomach did sommersaults.
"I know we've discussed the...uhh...mechanics of reproduction in our Biology classes before," Sarah continued, "but today I want to talk you about relationships, why people want to have sex, our bodies, and how you can protect yourself when you...umm...have sex."
When James remained silent, Sarah bravely soldiered on and began to talk about healthy relationships, love, consent and trust. Skirting around the edges of sex, not talking about it directly, helped to relax James and he began to open up by asking questions. For the first time, he was voicing curiosity about women and an interest in them - not just to his mother, but to anyone at all. Whilst he was still very reserved, it was a start. After about 15 minutes, Sarah knew she had to start moving the conversation forwards.
"So, sweetie, we've talked about relationships and how to create a safe environment with someone. But...why do you think people have sex, James?"
James paused and thought. There was an obvious answer - to make babies. He'd known that for years now. Was this a trick question?
"Umm...to...have children?" James replied timidly.
Sarah smiled at him indulgently, feeling warmth towards her son for his innocence.
"Well, yes sweetie." She giggled kindly. "Yes, that is true. But why else? People don't just have sex so they can get pregnant."
James felt like he should know the answer to this question and it was very obvious, but he just didn't know what to say. When it came down to it, he really didn't know anything about sex and why people did it. He shook his head.
"I...don't know."
"Well..." Sarah paused and thought carefully about what to say next. "People have sex to express their feelings for someone - like love and care - but also attraction. Attraction is very important in relationships and sex. If you're not attracted to someone then it becomes difficult to have sex with them. Do you know why that is sweetie?".
Once again, James shook his head. Sarah kept going, not giving herself a chance to feel awkward.
"Well, honey, for a boy to have sex he needs...to have an erection. Boys get erections when they see or think about something, or someone, that they are sexually attracted to. That's known as being aroused but most people call it being 'turned on'. Now, everyone is different. What arouses some people doesn't arouse others. We all have our own preferences and part of growing up is learning what you like."
James nodded to show he understood. In the brief moment of silence, Sarah thought about some of the things James had been searching on his PC and decided to guide the conversation in that direction.
"So, umm...what is it that you like, sweetie?"
James looked at her in confusion. "What do you mean, Mum?"
Sarah gave him a warm smile and tried her best to ignore her increasing heart rate. "I mean...what arouses you, sweetie? Is there anything that gives you an erection when you think about it?".
James stared at her with wide eyes and stammered. "I...uhh..."
"It's alright, honey." Sarah said with a warm, reassuring tone, doing her best to encourage her son. "You can tell Mummy. Remember I said that you can tell me anything. I won't judge you."
James sat uncomfortably across from his mother. The truth was that the first time he had an erection was years ago when he saw his Mum getting dressed. She only had black lacy underwear on and her breasts swayed and jiggled as she walked around the room. Ever since that moment he had been fascinated with big boobs. How they looked, how they moved, what they felt like. He'd never touched boobs before and, never having had a girlfriend, had only ever seen his mother's breasts before in real life, but the thought of them always gave him a stiffy and he sometimes couldn't help but looking at his Mum's cleavage.
"James?" Sarah said, gently prompting him.
"Well...I..." James's heart was beating very fast but he couldn't ignore his Mother's intense gaze. There was no escaping this conversation. "Umm...I like...boobs", he mumbled. "...big boobs...".
These words weren't unexpected but Sarah still felt a little uneasy in her choice of clothing now, realising how much of her cleavage was suddenly on show. Nevertheless, she gave a motherly smile and nodded encouragingly to James.
"That's OK, sweetie. It's very normal for boys to like big breasts. What is it that you like about them?"
James's eyes darted to his mother's cleavage, then back to her blue eyes. It was only for a brief moment, and it wasn't on purpose, but Sarah certainly noticed.
"Umm...I just like how they look and...how they wobble..." Sarah did her best to stifle at giggle at this comment.
"How they wobble?" Sarah gave her son playful look. "Do you mean...you like the shape of natural breasts and how they move?"
James nodded, his face red in embarrassment. "Whenever I think about it I get...you know...". James tailed off, not making eye contact.
"Does it make your willy stiff?" Sarah asked, kindly.
James blushed a deeper red and nodded again, still not making eye contact.
"That's OK, honey. Thank you for sharing that. It's perfectly natural and normal for your body to react in that way. In fact, it's really important that it does. If you don't get an erection then, as you know, you can't have sex."
Sarah smiled warmly at her son again, trying her best to make him feel comfortable and safe. It was at this point that she leaned over and pulled out one of the bananas and a box of condoms from the shopping back then placed them on the table.
"Now, sweetie, it's important that you keep yourself safe when you have sexual intercourse. You don't want to risk pregnancy every time you have sex and you need to be careful that you don't catch any infections either. So, before you have sex you need to put on a condom. Do you know what a condom is, honey?" Sarah asked encouragingly.
James made eye contact with his mother again and shook his head, still a little red in the face. This was becoming a bit much for him.
"That's ok, sweetheart." Sarah reassured him. "A condom is like a little cover, or jacket, that goes over your willy to protect it. It all catches your cummies so you can't get your partner pregnant." After James stared at her like a deer in headlights for a few moments, Sarah added "Here, look...I'll show you!".
Sarah picked up the box of condoms, opened it and pulled one out. Taking care to show James how it should be properly opened, she tore the outer packaging and took the small condom out of the wrapper.
"So this is a condom." Sarah said, ensuring James could properly see. With her other hand she picked up the banana from the table. "Now, what you've got to do is place the condom on the tip of your willy when it's erect, pinch the top then gently roll it down like this, making sure it doesn't tear."
As she spoke, Sarah expertly used her soft fingers to roll the condom down the banana until it was right at the bottom. As she held it in her hand, she felt a little strange as she suddenly realised it represented James' penis.
"See, it's easy! Nothing to worry about honey." Sarah said with a smile as she took the condom off. "Now...it's your turn. Don't be shy sweetie!". She passed James the banana and a new condom, her dress straining to contain her chest and she leaned over towards him.
James breathed deeply as he took the banana and condom from his mother with shaking hands. His lips were dry and his heart was beating fast, but his mother's reassuring smile and encouragement made him feel braver. He tore open the package and the condom slipped out into his hands. Picking it up with his fingers, he examined it with curiosity.
"It's all...slippery!", he said.
Sarah giggled, causing her breasts to jiggle up and down. "Yes, it's meant to be! That makes it more comfortably for the lady."
Focusing intensely, James placed the condom onto the tip of the banana then, rather cackhandedly with fumbling fingers, he slowly rolled the condom all the way down the length of the banana.
"I did it!" James cried in triumph, beaming at his mother.
"Well done, honey!" Sarah walked around the table and pulled James into a cuddle whilst he was still sat down. The side of his face was pressed against her warm, soft cleavage.
"I'm so proud of you for getting that right on your first attempt." Sarah looked down at her son with pride, kissed him on the forehead, then pulled him again into a hug completely unaware that his ear with virtually sandwich in her cleavage. All James could think about now was how warm and soft, yet firm, his mother's chest felt against the side of his head. It sent tingles throughout his body.
After a few moments she released him from the hug but kept a motherly hand on her shoulder. "Sweetheart, it's one thing to be able to put a condom onto a banana, but you need to know how to put one on yourself otherwise this is all a little pointless."
James looked up at his mother as she towered over him. The hand that wasn't on his shoulder was on her hip which was well accentuated by her dress. Her chest loomed over him in an almost intimidating fashion, but her facial expression was kind and her eyes twinkled with love. She spoke to him in an instructive tone, the same one she used when she was discussing something serious with him.
"What I want you to do is to take the condoms up into your room and to try to put one on yourself. Now, you may find it a little tricky and don't panic if you get it wrong. Just do your best and use another if the first one doesn't work." Sarah took a deep breath and felt herself flushing a little red with embarassment at this point. "Of course, in order to do this you'll need to...you know...have an erection. So just try to relax and take your time. If you need to...uhhh...use some visual aides then I give you permission to use the iPad for that just this once. You can come back down when you're done, sweetie." She smiled at him again and squeezed his shoulder. "Well...off you go!".
~~~~~~~~~~~
It had been nearly 30 minutes since James had disappeared upstairs into his bedroom and Sarah was impatiently pacing up and down in the kitchen. What could be taking so long? She thought it might take him a few attempts to get it right but this just seemed way too long now. Should she go up? She got butterflies in her stomach at the thought of what she might see. On the other hand, she had promised herself that today would be about James and everything she was going to do would be for his benefit. He could be sitting in his room on his own having a meltdown right now. She had to do something!
Without further thought, Sarah walked out of the kitchen and rushed up the stairs so fast that her breasts bounced aggressively as she ascended. Arriving onto the landing she could see the door to James' room closed.
"James?" She softly called out, but there was no reply so she walked up towards his door. "Sweetie, are you ok?". Again, there was no reply so she put her ear to the door and enquired again, "Honey, do you need some help?". She heard movement from inside and what sounded like the elastic waistband of underwear being pulled up.
"Umm...Mum...I can't do it."
Upon hearing these words, Sarah immediately opened the door and walked into her son's bedroom. Her heart ached with pity and loving affection at the sight she was greeted with. James was sitting at the edge of his bed with his shorts around his ankles so he was just sitting in his white y-front pants and tshirt. There were 4 unravelled condoms laying next to him along with the iPad and he had an upset expression on his face.
"Oh sweetheart!" She softly exclaimed in a very comforting and motherly tone. She walked over his him, sat next to him on the edge of the bed, put her arm around him and pulled him into a cuddle to his head rested on her collarbone. "It's OK, honey. What happened?"
"I couldn't get it on." James let his little body melt into his mothers. "I just...I couldn't work it out. Then I got frustrated and my...it just went soft and I couldn't make it go hard again..." James confessed with a slight tremble in his voice.
"Shhh, it's alright, my love." She put both arms around him with one hand stroking his hair gently. "It's OK, sweetheart. I know this can be stressful but you're safe here." As Sarah craddled her son closely to her chest and calmed him down, she looked over at the iPad laying next to her. On the screen was a picture of a very volumptuous woman exposing her breasts. She looked about Sarah's age and was worryingly similar in figure to her own. Sarah's mind was working fast. She knew what she must do, and she was just going to get on with it.
She released him from the hug enough that she could now look down at him and give him a comforting smile. "We'll figure this out together. Mummy will help you, it'll be OK!".
TO BE CONTINUED....
~~~~~~~~~~~
Sarah sighed heavily as she relucantly got out of bed. She had put today off for a long time, but she knew that it just couldn't wait any longer. When she had decided to home-school her son James 11 years ago, she hadn't appreciated that some topics would be rather uncomfortable to cover. Back then it was all basic Mathematics, English, Geography, History...the fun and easy stuff! But now, not so much.
Sarah was a single mother in her mid-40s. Her divorce left her very financially secure, so when her only son James was being horrendously bullied at the boarding school he was being sent to, it felt like the right decision to home-school him. Sarah was, after all, a very intelligent woman in her own right and living on her own wasn't what she wanted. She could spend a lot more quality time with James this way and parent him without the interference of her ex-husband or the influence of others.
The beauty of her youth was still very evident in motherhood. Standing 5ft 9, she had an enviable hourglass figure with surprisingly large 34G natural breasts, a slender tummy, delightfully wide hips and peachy bottom. Her long brunette hair was waist length, she had piercing blue eyes and slightly mousy facial features. She was not lacking attention since her divorce but had never sought another man's company.
James, on the other hand, had not yet bloomed and puberty was still a bit of a work-in-progress for him. Still only 5ft 4, James was slender and slight with curly, light brown hair, a larger than average nose and freckles. His one redeeming feature was his bright blue eyes, which he inherited from his mother. He was a timid boy who preferred being on his computer to being outside, but he was polite, helpful and loving. The relationship between Sarah and James was a close one, with Sarah providing the structure, love and guidance that James needed but also acting as a figure of authority when required.
~~~~~~~~~~~
Sarah knew that - as a parent - she should have had "the chat" with James years ago, but as his teacher there really was no good excuse for not having covered Sex Education with him before now. It just made her feel really uncomfortable so she had convinced herself that it simply didn't need to happen, especially as James wasn't necessarily acting like a typical teenager. But that excuse had long since run its course. She could no longer ignore the involuntary glances he would give her chest when she wore a tank top without a bra, or the curious looks he gave on the occasions he would see Sarah in her underwear whilst getting dressed, nor the little tent in his pjs he would sometimes get in the morning. What was most concerning of all were the Google searches she found on their shared iPad. In and amongst all of the gaming and other harmless content were searches like...
"Average penis size"
"Big boobs"
"What do boobs feel like?"
"What size should my penis be?"
All of these were a clear sign of a boy who was developing certain feelings, interests and concerns but wasn't being given the right information and assurances to be able to manage those feelings appropriately. And it was all her fault. She should have been the one to answer those questions. As uncomfortable as it made her feel, she was responsible for her son feeling lost.
No, the time was now. Today. It had to be. It was the right thing to do. Sarah had sought help on places like Mumsnet but everyone had a different opinion on the subject. Also, not being a qualified teacher herself, she had no access to official Sex Education material. She had decided to do her best, put on a brave face and hope that everything would work out. She had planned it out in her head, up until a point, then was just going to wing it! The key was to try to hide her feelings of embarrassment, be informative and try to get James to open up to her so she could guide the conversation in the right direction.
~~~~~~~~~~~
It was a gloriously, sunny Friday morning and Sarah dressed appropriately in a light floral V-necked yellow Summer dress which rested just above her knees and did its best to contain her heavy, full chest. Underneath she wore her favourite, well-supported white plunge bra and a matching white thong. As she put on her sandals, she steadied herself ready to face the day then headed downstairs to make breakfast.
As she walked downstairs she could already hear the TV on in the lounge meaning James was up and about - a good start. Sarah headed into the kitchen and began busying herself with making toast and putting out a selection of spreads on the table.
"James! Breakfast's ready!" She called, as she poured them some orange juice. James walked into the room still wearing his loose fitting Batman pajamas and sat down at the table. Whilst Sarah found it adorable that her little boy still liked to wear superhero pajamas, she knew that she really should buy him something a little more mature soon.
"Morning Mum!" James said, as she grabbed himself some toast. "Did you sleep well?".
"Yes, thanks sweetie." Sarah replied, not entirely truthfully. "It looks like you did too! It's nearly half past eight. We've got a lot to get done today and you're not even washed or dressed yet."
James frowned slightly and looked over to the Weekly School Schedule attached to the fridge to see what the timetable was for today.
9am-10am: Mathematics
10am-10.30am: Geography Revision
10.30am-11am: Break
11am onwards: Miscellaneous
"Miscellaneous? What's that, Mum?" James asked curiously as he looked back at Sarah.
"Never you mind, young man. We'll talk about that later. But you've got half an hour to get up those stairs, shower, get dressed and be back down at this kitchen table with all your books." Sarah said this in a slightly more authoritative tone than she intended, probably to mask how nervous she felt, so she gave James a reassuring smile before adding, "Go on, love. Off you go!".
As James disappeared upstairs still chewing his last mouthful of toast, Sarah leant back against the kitchen side and steadied her breathing. She could feel her elevated heart rate, slightly faster breathing and a nervous knot in her stomach. "Pull yourself together!", she thought to herself. "Today is about James, not about you. You've got a plan. It's going to be fine." She closed her eyes for a brief moment, gathered herself together, and began clearing the table ready for the start of lessons.
~~~~~~~~~~~
James got out of the shower, towel-dried his hair then wrapped then towel around his slender waist as he walked into his bedroom to get dressed. His bedroom was well kept as always, with the exception of a half built Star Wars Lego model in the corner with the box and random bags of pieces neatly ordered in a row. He'd finish that off later; the perfect Friday night! His PC sat on his desk in the back right of the room and his bed was on the other side of that. He walked over to his chest of drawers and pulled out a fresh pair of white y-fronts and some Darth Vader socks, then took a pair of beige shorts and a tshirt out of his wardrobe. He then let the towel drop to the floor as he prepared to get dressed. He caught sight of himself in his mirror and sighed. He was still so short and skinny for his age. He only had one or two tufts of light wispy hair on his chest and his genitals were still hairless and soft-skinned. His balls sat tightly in his coin purse and his penis - or "willy" as Mum called it - was still the small size as it had been for years. He measured it once after hearing the boys at school talking about theres and that had only lead to disappointment, as had Googling the average penis size. His was quite a bit below that.
Putting that to the back of his mind, James pulled up his pants and began to get dressed. Curiousity was the main thing that filled his mind now. "Miscellaneous....I wonder what that could mean", he thought to himself. "Last time that was on the timetable we went on a fieldtrip to the Welsh seaside near Tenby to see examples of coastal erosion. Maybe it's another field trip!". Whilst that could be fun, James wasn't a massive fan of surprises and the thought of the unknown made him feel a little uneasy. Mum also acted a little weirdly when he asked her about it earlier, which made him a little suspicious. Now fully dressed, he gathered his books and headed downstairs to begin the day.
~~~~~~~~~~~
"How are you getting on with those Differentiations and Integrations, sweetie?"
"I'm....done!" said James, with a smile on his face. "You're going to have to step your game up, Mum. Those were too easy!".
James passed Sarah his workings for her inspection. Sarah had just set James a load of questions this morning rather than teaching him anything new. She just wasn't in the right headspace to cover new content as her mind was very pre-occupied with what was still to come. She looked over the immaculate work and gave James a warm, encouraging smile.
"Good boy. Perfect as usual - my little mathematician!". Sarah glanced up at the clock. 9.57am. "Why don't you clear all of this away and start your Geography revision? I've just got to pop to the shops and I may not be back until you've started your break."
"Oh...ok, sure. What are you getting?"
"Nothing exciting." Sarah replied as she grabbed her handbag and car keys. "Just a few bits. Now you focus on that revision, young man. I'll know if you've not done it!". She gave James a smile and a playful wink as she walked out the front door, clearly indicating that she trusted him implicity and knew he would never dream of not doing his work just because she wasn't there.
~~~~~~~~~~~
As Sarah parked up at the Supermarket she took a deep, steadying breath which caused her large chest to strain against the confines of her dress. The knot of anxiety in her stomach was getting worse. What she had thought about and planned for weeks was finally becoming a reality. Not letting her resolve waver, she got out of the car and walked confidently into the shop.
Knowing exactly what she needed, Sarah headed straight for the Fruit & Veg aisle. With her basket in one hand, she walked over to the cucumbers and picked up the nearest one. It was long, thick and mostly straight - perfect for representing a penis! It was almost in her basket before she paused. Something she had read on Mumsnet suddenly came into her mind, along with the memory of some of James's online searches. What if, as she suspected, James was somewhat below average in the willy department? She didn't want him to feel intimidated or shamed during their lesson; that would be a disaster! She put the cucumber back and started to wonder up the aisle. Ahh, what about these? She picked up a bunch of small bananas. They were a little curved but much thinner than the cucumber and only 4-5 inches in length. Far more appropriate! They went straight into her basket before she headed over to the Pharmacy aisle.
At this point, Sarah looked around a little nervously as if worried she was going to be seen doing something wrong or recognised by someone she knew. After confirming the coast was clear, she walked towards the selection of condoms on offer. She immediately discounted all of the extra large, flavoured and ribbed ones - they would be of no use! Next were just a choice of regular condoms but right at the end was what she was after. According to the box they were a "Trim" size and ideal for men who "do not need it very wide". Whilst the thought of her son filling one of these condoms made her uncomfortable, she grabbed the box and headed straight for the self-service machine to pay to avoid any unwanted interactions.
~~~~~~~~~~~
James was in his bedroom with his curtains draw and headset on playing one of his games. Gaming provided him with the ultimate escape and it was the best way he knew to make him forget his anxieties like the feelings of apprehension he had about the rest of the day. He looked at his watch which read 10.51am, then he heard the door click open. Mum was home! There wasn't long left of his break so he decided he was going to go downstairs early and find out what was going on. He exited his game, took off his headset and drew the curtains back so sunlight flooded his bedroom. As he headed downstairs he called "Hey Mum!" to find out where she was, but the rustling noises in the kitchen answered that question for him.
As he walked into the kitchen, his Mum was standing there waiting for him holding a shopping bag. The kitchen table was cleared of all books. She smiled at him.
"Hello sweetheart. Why don't you sit down?". This wasn't so much an invitation as a kind instruction, which he habitually obeyed but with some apprehension. Normally when she spoke to him like this were on the very rare occasions that he got in trouble. What could he have done wrong? As he sat down he watched as Sarah walked over to the blinds and drew them slightly so sunlight was still coming in but he wouldn't see out into the garden. She walked back over to him, her chest bouncing slightly in her dress as she did so, sat down opposite him and put the shopping bag on the seat next to her out of sight.
"What's in the b-"
"Honey." She cut across him before he could finish his question. "I want to talk to you about something a little different this morning, but I'm going to need you to be the good, mature boy I know you can be. I want you to listen carefully and engage with me. I also want you to not be afraid to ask me questions. No question is a silly question and I promise I won't be angry at anything you say. You can tell me anything, sweetheart. Do you understand me?"
"Umm...yes, Mum. I understand." James nodded politely, feeling nervous.
"Good boy." She pauses for a moment and takes a deep breath, her heavy bosom rising and falling. "Today I want to talk to you about sex."
A silence fell over the kitchen as James just stared at his mother whilst his stomach did sommersaults.
"I know we've discussed the...uhh...mechanics of reproduction in our Biology classes before," Sarah continued, "but today I want to talk you about relationships, why people want to have sex, our bodies, and how you can protect yourself when you...umm...have sex."
When James remained silent, Sarah bravely soldiered on and began to talk about healthy relationships, love, consent and trust. Skirting around the edges of sex, not talking about it directly, helped to relax James and he began to open up by asking questions. For the first time, he was voicing curiosity about women and an interest in them - not just to his mother, but to anyone at all. Whilst he was still very reserved, it was a start. After about 15 minutes, Sarah knew she had to start moving the conversation forwards.
"So, sweetie, we've talked about relationships and how to create a safe environment with someone. But...why do you think people have sex, James?"
James paused and thought. There was an obvious answer - to make babies. He'd known that for years now. Was this a trick question?
"Umm...to...have children?" James replied timidly.
Sarah smiled at him indulgently, feeling warmth towards her son for his innocence.
"Well, yes sweetie." She giggled kindly. "Yes, that is true. But why else? People don't just have sex so they can get pregnant."
James felt like he should know the answer to this question and it was very obvious, but he just didn't know what to say. When it came down to it, he really didn't know anything about sex and why people did it. He shook his head.
"I...don't know."
"Well..." Sarah paused and thought carefully about what to say next. "People have sex to express their feelings for someone - like love and care - but also attraction. Attraction is very important in relationships and sex. If you're not attracted to someone then it becomes difficult to have sex with them. Do you know why that is sweetie?".
Once again, James shook his head. Sarah kept going, not giving herself a chance to feel awkward.
"Well, honey, for a boy to have sex he needs...to have an erection. Boys get erections when they see or think about something, or someone, that they are sexually attracted to. That's known as being aroused but most people call it being 'turned on'. Now, everyone is different. What arouses some people doesn't arouse others. We all have our own preferences and part of growing up is learning what you like."
James nodded to show he understood. In the brief moment of silence, Sarah thought about some of the things James had been searching on his PC and decided to guide the conversation in that direction.
"So, umm...what is it that you like, sweetie?"
James looked at her in confusion. "What do you mean, Mum?"
Sarah gave him a warm smile and tried her best to ignore her increasing heart rate. "I mean...what arouses you, sweetie? Is there anything that gives you an erection when you think about it?".
James stared at her with wide eyes and stammered. "I...uhh..."
"It's alright, honey." Sarah said with a warm, reassuring tone, doing her best to encourage her son. "You can tell Mummy. Remember I said that you can tell me anything. I won't judge you."
James sat uncomfortably across from his mother. The truth was that the first time he had an erection was years ago when he saw his Mum getting dressed. She only had black lacy underwear on and her breasts swayed and jiggled as she walked around the room. Ever since that moment he had been fascinated with big boobs. How they looked, how they moved, what they felt like. He'd never touched boobs before and, never having had a girlfriend, had only ever seen his mother's breasts before in real life, but the thought of them always gave him a stiffy and he sometimes couldn't help but looking at his Mum's cleavage.
"James?" Sarah said, gently prompting him.
"Well...I..." James's heart was beating very fast but he couldn't ignore his Mother's intense gaze. There was no escaping this conversation. "Umm...I like...boobs", he mumbled. "...big boobs...".
These words weren't unexpected but Sarah still felt a little uneasy in her choice of clothing now, realising how much of her cleavage was suddenly on show. Nevertheless, she gave a motherly smile and nodded encouragingly to James.
"That's OK, sweetie. It's very normal for boys to like big breasts. What is it that you like about them?"
James's eyes darted to his mother's cleavage, then back to her blue eyes. It was only for a brief moment, and it wasn't on purpose, but Sarah certainly noticed.
"Umm...I just like how they look and...how they wobble..." Sarah did her best to stifle at giggle at this comment.
"How they wobble?" Sarah gave her son playful look. "Do you mean...you like the shape of natural breasts and how they move?"
James nodded, his face red in embarrassment. "Whenever I think about it I get...you know...". James tailed off, not making eye contact.
"Does it make your willy stiff?" Sarah asked, kindly.
James blushed a deeper red and nodded again, still not making eye contact.
"That's OK, honey. Thank you for sharing that. It's perfectly natural and normal for your body to react in that way. In fact, it's really important that it does. If you don't get an erection then, as you know, you can't have sex."
Sarah smiled warmly at her son again, trying her best to make him feel comfortable and safe. It was at this point that she leaned over and pulled out one of the bananas and a box of condoms from the shopping back then placed them on the table.
"Now, sweetie, it's important that you keep yourself safe when you have sexual intercourse. You don't want to risk pregnancy every time you have sex and you need to be careful that you don't catch any infections either. So, before you have sex you need to put on a condom. Do you know what a condom is, honey?" Sarah asked encouragingly.
James made eye contact with his mother again and shook his head, still a little red in the face. This was becoming a bit much for him.
"That's ok, sweetheart." Sarah reassured him. "A condom is like a little cover, or jacket, that goes over your willy to protect it. It all catches your cummies so you can't get your partner pregnant." After James stared at her like a deer in headlights for a few moments, Sarah added "Here, look...I'll show you!".
Sarah picked up the box of condoms, opened it and pulled one out. Taking care to show James how it should be properly opened, she tore the outer packaging and took the small condom out of the wrapper.
"So this is a condom." Sarah said, ensuring James could properly see. With her other hand she picked up the banana from the table. "Now, what you've got to do is place the condom on the tip of your willy when it's erect, pinch the top then gently roll it down like this, making sure it doesn't tear."
As she spoke, Sarah expertly used her soft fingers to roll the condom down the banana until it was right at the bottom. As she held it in her hand, she felt a little strange as she suddenly realised it represented James' penis.
"See, it's easy! Nothing to worry about honey." Sarah said with a smile as she took the condom off. "Now...it's your turn. Don't be shy sweetie!". She passed James the banana and a new condom, her dress straining to contain her chest and she leaned over towards him.
James breathed deeply as he took the banana and condom from his mother with shaking hands. His lips were dry and his heart was beating fast, but his mother's reassuring smile and encouragement made him feel braver. He tore open the package and the condom slipped out into his hands. Picking it up with his fingers, he examined it with curiosity.
"It's all...slippery!", he said.
Sarah giggled, causing her breasts to jiggle up and down. "Yes, it's meant to be! That makes it more comfortably for the lady."
Focusing intensely, James placed the condom onto the tip of the banana then, rather cackhandedly with fumbling fingers, he slowly rolled the condom all the way down the length of the banana.
"I did it!" James cried in triumph, beaming at his mother.
"Well done, honey!" Sarah walked around the table and pulled James into a cuddle whilst he was still sat down. The side of his face was pressed against her warm, soft cleavage.
"I'm so proud of you for getting that right on your first attempt." Sarah looked down at her son with pride, kissed him on the forehead, then pulled him again into a hug completely unaware that his ear with virtually sandwich in her cleavage. All James could think about now was how warm and soft, yet firm, his mother's chest felt against the side of his head. It sent tingles throughout his body.
After a few moments she released him from the hug but kept a motherly hand on her shoulder. "Sweetheart, it's one thing to be able to put a condom onto a banana, but you need to know how to put one on yourself otherwise this is all a little pointless."
James looked up at his mother as she towered over him. The hand that wasn't on his shoulder was on her hip which was well accentuated by her dress. Her chest loomed over him in an almost intimidating fashion, but her facial expression was kind and her eyes twinkled with love. She spoke to him in an instructive tone, the same one she used when she was discussing something serious with him.
"What I want you to do is to take the condoms up into your room and to try to put one on yourself. Now, you may find it a little tricky and don't panic if you get it wrong. Just do your best and use another if the first one doesn't work." Sarah took a deep breath and felt herself flushing a little red with embarassment at this point. "Of course, in order to do this you'll need to...you know...have an erection. So just try to relax and take your time. If you need to...uhhh...use some visual aides then I give you permission to use the iPad for that just this once. You can come back down when you're done, sweetie." She smiled at him again and squeezed his shoulder. "Well...off you go!".
~~~~~~~~~~~
It had been nearly 30 minutes since James had disappeared upstairs into his bedroom and Sarah was impatiently pacing up and down in the kitchen. What could be taking so long? She thought it might take him a few attempts to get it right but this just seemed way too long now. Should she go up? She got butterflies in her stomach at the thought of what she might see. On the other hand, she had promised herself that today would be about James and everything she was going to do would be for his benefit. He could be sitting in his room on his own having a meltdown right now. She had to do something!
Without further thought, Sarah walked out of the kitchen and rushed up the stairs so fast that her breasts bounced aggressively as she ascended. Arriving onto the landing she could see the door to James' room closed.
"James?" She softly called out, but there was no reply so she walked up towards his door. "Sweetie, are you ok?". Again, there was no reply so she put her ear to the door and enquired again, "Honey, do you need some help?". She heard movement from inside and what sounded like the elastic waistband of underwear being pulled up.
"Umm...Mum...I can't do it."
Upon hearing these words, Sarah immediately opened the door and walked into her son's bedroom. Her heart ached with pity and loving affection at the sight she was greeted with. James was sitting at the edge of his bed with his shorts around his ankles so he was just sitting in his white y-front pants and tshirt. There were 4 unravelled condoms laying next to him along with the iPad and he had an upset expression on his face.
"Oh sweetheart!" She softly exclaimed in a very comforting and motherly tone. She walked over his him, sat next to him on the edge of the bed, put her arm around him and pulled him into a cuddle to his head rested on her collarbone. "It's OK, honey. What happened?"
"I couldn't get it on." James let his little body melt into his mothers. "I just...I couldn't work it out. Then I got frustrated and my...it just went soft and I couldn't make it go hard again..." James confessed with a slight tremble in his voice.
"Shhh, it's alright, my love." She put both arms around him with one hand stroking his hair gently. "It's OK, sweetheart. I know this can be stressful but you're safe here." As Sarah craddled her son closely to her chest and calmed him down, she looked over at the iPad laying next to her. On the screen was a picture of a very volumptuous woman exposing her breasts. She looked about Sarah's age and was worryingly similar in figure to her own. Sarah's mind was working fast. She knew what she must do, and she was just going to get on with it.
She released him from the hug enough that she could now look down at him and give him a comforting smile. "We'll figure this out together. Mummy will help you, it'll be OK!".
TO BE CONTINUED....
