RachelMILFTV
12-20-2024, 03:56 PM
Please let me know what you think of my story with a comment. Thanks!
Sam was an average 16-year-old, a good looking but fairly plain looking and shy youngster, navigating the labyrinth of adolescence in a standard detached house in the suburbs. He was close to his father, Mark and mum Marissa, both hardworking parents who balanced their demanding jobs with raising him. They enjoyed a comfortable but not affluent family lifestyle, Mark and Marissa always ensured they shared moments of joy and laughter. One evening, after a particularly taxing day at school, Sam wandered into his parent's room bored and feeling a bit curious. Both his parent's were at work and wouldn't be home for a good few hours, leaving Sam alone with his thoughts and curiosity.
As he sat on his parent's neatly made bed, Sam's eyes were drawn to the dressing table. It was a wooden piece, vintage yet elegant, with an array of grooming products and perfumes and aftershaves meticulously arranged on its surface. But it was the drawer beneath that caught his curiosity. Tentatively, he opened it and found his mother's makeup collection. She wasn't really someone who wore much makeup except for a little blusher and lip gloss most of the time but with an occasional but of glamour for a rare romantic date night with Mark. Inside the drawer, Sam found an assortment of lipsticks, eyeshadows, and blushes, each telling a silent story of his mother's vibrant personality that rarely was displayed.
He picked up a bright red lipstick, feeling its weight in his hand. Tentatively, he twisted it open, revealing the bold, crimson colour and the unmistakable smell of lipstick. He glanced at the mirror, his reflection looking back at him with an expression he couldn't quite place. Intrigued and impulsive, he applied the lipstick, feeling an unexpected thrill as the colour stained his lips. The transformation was subtle yet profound, a small act that sparked something deep within him. Sam was only wearing a little bit of lipstick but instinctively he knew he loved it. A warm feeling washed over him as he looked at himself in the mirror. Being naturally cautious, Sam enjoyed the feeling, smell and look of the glossy lips for a few minutes before meticulously removing it and ever so carefully putting mum's lippy back in the dresser.
In the days that followed, Sam found himself thinking more and more of that brief moment sat in front of the mirror. He'd flick through his mum's magazines (it was the mid-90's before the internet was widely available!) looking at the makeup adverts thinking about all the colours, shades and looks that might suit him. Each time his heart raced and butterflies fluttered in his tummy: It was becoming a bit of an obsession! One day, a week or so later, Sam got up for school but told him mum that he had been sick in the night and wasn't well enough to go to school. Now, Sam's attendance at school was exceptional so Marissa had no reason to not believe him so she told Sam to go back to bed and rest, gave him a kiss and told him to call her work if he needed anything. Sam watched through his bedroom window as his parents gave each other a loving peck on the cheek before getting in their respective car's and driving to work.
Sam, as you might have guessed, wasn't in any way ill. He had this urge inside him which he couldn't ignore and desperately needed to indulge. He nervously waited 5 minutes to make sure the coast was clear. Sam the returned to the dressing table in his parents room. His heart was pounding and he felt another wave of excitement and anticipation. His hand's were literally shaking. Gathering himself, Sam took a few deep breaths, puffed out his cheeks and said "OK then!".
Carefully, Sam took different makeup, tubes, tubs, sticks, pencils, brushes and pads from the drawer and carefully ordered them. He had pinched one of his mum's beauty and fashion magazines and had already decided from the selection of looks which one he wanted to try. He flicked the magazine open to a picture of a young woman in her early 20s, beautifully made up with gorgeous glossy pink lipstick, subtle eye makeup and very natural foundation and a hint of pink blusher across the cheekbones to highlight. It was a look very popular with girls his own age at the time and one he felt would suit him best. His mum might not have all the colours and shades as an exact match, but there was enough in her palette to get as close as could be.
Sam studied the text of the magazine makeup guide, step-by-step. Applying a layer of foundation, then eyeliner, eye shadow, mascara before stopping to see himself in the mirror. He looked at himself and his heart raced even more... Sam could see the beginnings of something. He smiled at himself in the mirror. Just the lipstick to go...
It started with lipstick and this was the major part of Sam's interest in makeup. It totally completed and sometimes transformed a look. This was where he deviated from the picture in the magazine. The model had a Pink tinted lip gloss, where as Sam wanted something a bit bolder and more eye catching and dare I say tarty! He picked a full glossy Pink vinyl shade from mum's collection and ever so carefully started applying it to his lips. The buzz and feel of getting the greasy lippy applied was such a thrill!
He sat up and back in the chair next to the dressing table mirror and looked at himself. "Oh wow!" Sam thought. He tilted his head from side-to-side, up-and-down slowly to see his handy work and first attempt at full face makeup. His eyes started to fill a little which was totally unexpected! Sam was not an emotional person, but there was just something that got to him as he looked at himself in the mirror. But wait! Something was missing! He had missed a streak of blusher across his cheekbones. With a flick of the big brush across each cheek, Sam was properly done. Nearly in tears two minutes ago, Same was now beaming with smiles in the mirror, he sat for what seemed like ages looking at his made-up face. Looking close-up he was noticing it was far from perfect as you'd expect but for a first attempt you'd say he was a natural at it! He pouted and blew himself a kiss in the mirror then winked. "Where did that come from!?" Sam thought. Even his mannerisms were feminising.
Safe in the knowledge he was alone for the rest of the day, Sam looked for some underwear. Nothing overly sexy, just basic bra, knickers, a skirt and blouse maybe, which he found and put on. Sam was a fair bit taller than his mum so whilst he fitted in to the clothes they weren't exactly a perfect fit! This didn't bother him but he did wish there was more choice suitable for someone his age! Despite this he felt so good. Watching himself in the full-length mirror as he walked up and down.
The remainder of the day, he experimented with different shades of eyeshadow, learned to blend foundation better, and discovered the art of contouring. Each session in front of the mirror was a step towards self-discovery, a journey he hadn't anticipated but found himself eagerly embracing. It felt natural and it was. Before the end of the afternoon, Sam meticulously tidied up after himself, putting everything carefully back where it came from, removing any evidence and leaving himself plenty time to take the makeup off and wash his face before showering. It was then that Sam learned how many wipes it takes to remove waterproof mascara and eyeliner!
Sam kept his secret well-guarded, but with exams (GCSEs) and six weeks of summer holiday less than two months away he had next to no time to practice his newfound passion. He was counting down to the school holidays where his parent's would be at work. Usually during school holidays, Sam would be out with friends, bike riding or playing football. This summer holiday was different. He started to purchase his own makeup, hiding it in the back of his wardrobe. His confidence grew with each experiment, and he began to appreciate the art of makeup not just as a means of transformation, but as a way to express his true self.
The final missing touch was a wig. Sam loved how he looked in female clothes and makeup but the transformation was lacking something and having short boyish hair didn't help! These were the days before online shopping so Sam needed to come up with a plan. Being the bright, resourceful youngster he was, Sam had an idea. There was a joke shop in the city centre where he and his mates would go a spend pocket money on silly joke things. However, they also sold dressing up things including wigs. Sam's plan was to go in to the joke shop and say that his mum was going to a fancy dress party as the blonde lady from ABBA. This is exactly what he did and the lady in the shop couldn't have been more helpful, offering him accessories to compliment the look!
Sam would spend 3 days a week dressing and experimenting with make-up during the school holidays, making sure he saw his friends outside of those times so his parent's didn't suspect he was up to something. It was bliss, absolutely bliss and he had his routine to make sure everything was put back as it should be before anyone came home.
Ever on the hunt for other outfits, shoes and jewellery he could wear, Sam was often rummaging through his parent's walk-in wardrobe. So far he obviously only been looking through his mum's side of the wardrobe. After three days a week for three weeks of trying on pretty much everything, Sam had exhausted his mum's collection. Frustrated he looked over to his dad's side of the wardrobe and saw a big box he'd never looked inside of. "Maybe it's where mum keeps all her sexy, slinky lingerie." He thought amused. There would be only one way to find out!
Sam opened the box. There weren't any clothes in there but it was a huge hidden collection of pornography! 100s of magazines and VHS videos. Shocked and very curious, Sam examined the magazines and videos, most of the content was mainstream, the sort of things you'd find on the top shelf of most newsagents back in the 1990's. "Still", Sam thought, "there are more makeup looks I can try and recreate". He flicked through each of the magazines and made a mental note of those looks he could try and add to his repertoire. More pornstar than high-street fashion! The VHS weren't labelled and clearly copies of something, but they could wait.
There was a second box obscured by a few old coats over the top of it. "Oh" mused Sam, "More material!". Expecting more of the same adult glamour magazines and VHS tapes, Sam was shocked but intrigued to find that this box had more very hardcore European titles. His eye's widened and interest piqued. Sam had never seen anything like it before! He kept delving in to this new, more exotic box of treasures and pulled out a handful of around 20 glossy magazines. Sam looked at the title and the explicit image on the front. "TRANSSEXUAL CLIMAX" was the name of the publication, he looked at the second, then the third, then fanned out the rest of the magazines. All of them Transsexual Climax. Sam sat there looking at the images of gorgeous trans girls, some posing solo and others with men.
Up til this point, female makeup and clothes hadn't been an overtly sexual thing for Sam. He'd be lying if he said he wasn't aroused but had never masturbated whilst dressed. Until now that is. Sam was rock hard... so turned on like he had never been before! Sam gorged on these magazines, wishing he was the girls in them. A brand new feeling and another huge step in the transformation and evolution if his emerging feminine side.
For the next week, Sam's routine was the same in terms of makeup and clothes but with the finale being the watching of a VHS. He was delighted to find half of all his dad's collection were trans girls!
This routine had worked perfectly for four weeks now, but something was about to change.
One early afternoon, as Sam was perfecting a smokey eye look borrowed from one of the trans girls in the magazines, he heard the front door creak open. Panic surged through him as he scrambled to hide the makeup and rush in to a bathroom to lock the door. No-one was supposed to be home, but it was too late. His dad, Mark, stood at the doorway, his eyes wide with surprise, scanning the evidence before him: clothes, makeup and trans porn mags, not to mention his son dolled up in full face makeup, bra and knickers and long blonde wig. Silence filled the room, heavy and uncomfortable.
"Sam, what are you doing?" Mark finally asked, his voice a mix of confusion and concern.
Sam's heart pounded in his chest and he instantly felt nauseous. He had always feared this moment, unsure of how his dad would react. "Dad, I... I like wearing makeup," he admitted, his voice trembling. "It makes me feel like myself."
Mark's expression was unreadable, and he took a step forward. "Why didn't you tell me or your mum?" he asked gently.
"I was scared," Sam confessed. "I didn't know how you'd react."
Mark took a deep breath and sat beside him. "I love you no matter what. If makeup and doing this makes you happy, then I support you."
"Please don't tell mum!" Sam begged
"I won't! I won't" his dad insisted. Marissa could be more volitile that Mark, so he fully understand the need to keep the secret.
Tears welled up in Sam's eyes as he nodded towards his dad, feeling some of the weight and guilt lift off his shoulders.
Sam was taken aback, but a sense of understanding quickly washed over him.
"By the way" Mark said, turning around before leaving the room. "You look beautiful, Rachel."
Rachel! She finally had her name.
Rachel smiled her biggest smile, her eyes shimmering with emotion. "Thank you, Dad."
A few day's later, Sam started to find little gifts of girls clothes, underwear, makeup, shoes, costume jewellery tucked away in his wardrobe which enable him to become more authentically Rachel. He knew exactly who they were from and some outfits were replicas of outfits from some of those special magazines and videos that had been discovered! It goes without saying that these were worn at the earliest possible opportunity.
Sam, now Rachel when dressed could embrace her true self. This transformation wasn't just about makeup; it was about embracing identity and living her truth.
Years later, as Rachel looked back on her journey, she realised that discovering his mother's makeup was the catalyst for many more adventures to come.
Sam was an average 16-year-old, a good looking but fairly plain looking and shy youngster, navigating the labyrinth of adolescence in a standard detached house in the suburbs. He was close to his father, Mark and mum Marissa, both hardworking parents who balanced their demanding jobs with raising him. They enjoyed a comfortable but not affluent family lifestyle, Mark and Marissa always ensured they shared moments of joy and laughter. One evening, after a particularly taxing day at school, Sam wandered into his parent's room bored and feeling a bit curious. Both his parent's were at work and wouldn't be home for a good few hours, leaving Sam alone with his thoughts and curiosity.
As he sat on his parent's neatly made bed, Sam's eyes were drawn to the dressing table. It was a wooden piece, vintage yet elegant, with an array of grooming products and perfumes and aftershaves meticulously arranged on its surface. But it was the drawer beneath that caught his curiosity. Tentatively, he opened it and found his mother's makeup collection. She wasn't really someone who wore much makeup except for a little blusher and lip gloss most of the time but with an occasional but of glamour for a rare romantic date night with Mark. Inside the drawer, Sam found an assortment of lipsticks, eyeshadows, and blushes, each telling a silent story of his mother's vibrant personality that rarely was displayed.
He picked up a bright red lipstick, feeling its weight in his hand. Tentatively, he twisted it open, revealing the bold, crimson colour and the unmistakable smell of lipstick. He glanced at the mirror, his reflection looking back at him with an expression he couldn't quite place. Intrigued and impulsive, he applied the lipstick, feeling an unexpected thrill as the colour stained his lips. The transformation was subtle yet profound, a small act that sparked something deep within him. Sam was only wearing a little bit of lipstick but instinctively he knew he loved it. A warm feeling washed over him as he looked at himself in the mirror. Being naturally cautious, Sam enjoyed the feeling, smell and look of the glossy lips for a few minutes before meticulously removing it and ever so carefully putting mum's lippy back in the dresser.
In the days that followed, Sam found himself thinking more and more of that brief moment sat in front of the mirror. He'd flick through his mum's magazines (it was the mid-90's before the internet was widely available!) looking at the makeup adverts thinking about all the colours, shades and looks that might suit him. Each time his heart raced and butterflies fluttered in his tummy: It was becoming a bit of an obsession! One day, a week or so later, Sam got up for school but told him mum that he had been sick in the night and wasn't well enough to go to school. Now, Sam's attendance at school was exceptional so Marissa had no reason to not believe him so she told Sam to go back to bed and rest, gave him a kiss and told him to call her work if he needed anything. Sam watched through his bedroom window as his parents gave each other a loving peck on the cheek before getting in their respective car's and driving to work.
Sam, as you might have guessed, wasn't in any way ill. He had this urge inside him which he couldn't ignore and desperately needed to indulge. He nervously waited 5 minutes to make sure the coast was clear. Sam the returned to the dressing table in his parents room. His heart was pounding and he felt another wave of excitement and anticipation. His hand's were literally shaking. Gathering himself, Sam took a few deep breaths, puffed out his cheeks and said "OK then!".
Carefully, Sam took different makeup, tubes, tubs, sticks, pencils, brushes and pads from the drawer and carefully ordered them. He had pinched one of his mum's beauty and fashion magazines and had already decided from the selection of looks which one he wanted to try. He flicked the magazine open to a picture of a young woman in her early 20s, beautifully made up with gorgeous glossy pink lipstick, subtle eye makeup and very natural foundation and a hint of pink blusher across the cheekbones to highlight. It was a look very popular with girls his own age at the time and one he felt would suit him best. His mum might not have all the colours and shades as an exact match, but there was enough in her palette to get as close as could be.
Sam studied the text of the magazine makeup guide, step-by-step. Applying a layer of foundation, then eyeliner, eye shadow, mascara before stopping to see himself in the mirror. He looked at himself and his heart raced even more... Sam could see the beginnings of something. He smiled at himself in the mirror. Just the lipstick to go...
It started with lipstick and this was the major part of Sam's interest in makeup. It totally completed and sometimes transformed a look. This was where he deviated from the picture in the magazine. The model had a Pink tinted lip gloss, where as Sam wanted something a bit bolder and more eye catching and dare I say tarty! He picked a full glossy Pink vinyl shade from mum's collection and ever so carefully started applying it to his lips. The buzz and feel of getting the greasy lippy applied was such a thrill!
He sat up and back in the chair next to the dressing table mirror and looked at himself. "Oh wow!" Sam thought. He tilted his head from side-to-side, up-and-down slowly to see his handy work and first attempt at full face makeup. His eyes started to fill a little which was totally unexpected! Sam was not an emotional person, but there was just something that got to him as he looked at himself in the mirror. But wait! Something was missing! He had missed a streak of blusher across his cheekbones. With a flick of the big brush across each cheek, Sam was properly done. Nearly in tears two minutes ago, Same was now beaming with smiles in the mirror, he sat for what seemed like ages looking at his made-up face. Looking close-up he was noticing it was far from perfect as you'd expect but for a first attempt you'd say he was a natural at it! He pouted and blew himself a kiss in the mirror then winked. "Where did that come from!?" Sam thought. Even his mannerisms were feminising.
Safe in the knowledge he was alone for the rest of the day, Sam looked for some underwear. Nothing overly sexy, just basic bra, knickers, a skirt and blouse maybe, which he found and put on. Sam was a fair bit taller than his mum so whilst he fitted in to the clothes they weren't exactly a perfect fit! This didn't bother him but he did wish there was more choice suitable for someone his age! Despite this he felt so good. Watching himself in the full-length mirror as he walked up and down.
The remainder of the day, he experimented with different shades of eyeshadow, learned to blend foundation better, and discovered the art of contouring. Each session in front of the mirror was a step towards self-discovery, a journey he hadn't anticipated but found himself eagerly embracing. It felt natural and it was. Before the end of the afternoon, Sam meticulously tidied up after himself, putting everything carefully back where it came from, removing any evidence and leaving himself plenty time to take the makeup off and wash his face before showering. It was then that Sam learned how many wipes it takes to remove waterproof mascara and eyeliner!
Sam kept his secret well-guarded, but with exams (GCSEs) and six weeks of summer holiday less than two months away he had next to no time to practice his newfound passion. He was counting down to the school holidays where his parent's would be at work. Usually during school holidays, Sam would be out with friends, bike riding or playing football. This summer holiday was different. He started to purchase his own makeup, hiding it in the back of his wardrobe. His confidence grew with each experiment, and he began to appreciate the art of makeup not just as a means of transformation, but as a way to express his true self.
The final missing touch was a wig. Sam loved how he looked in female clothes and makeup but the transformation was lacking something and having short boyish hair didn't help! These were the days before online shopping so Sam needed to come up with a plan. Being the bright, resourceful youngster he was, Sam had an idea. There was a joke shop in the city centre where he and his mates would go a spend pocket money on silly joke things. However, they also sold dressing up things including wigs. Sam's plan was to go in to the joke shop and say that his mum was going to a fancy dress party as the blonde lady from ABBA. This is exactly what he did and the lady in the shop couldn't have been more helpful, offering him accessories to compliment the look!
Sam would spend 3 days a week dressing and experimenting with make-up during the school holidays, making sure he saw his friends outside of those times so his parent's didn't suspect he was up to something. It was bliss, absolutely bliss and he had his routine to make sure everything was put back as it should be before anyone came home.
Ever on the hunt for other outfits, shoes and jewellery he could wear, Sam was often rummaging through his parent's walk-in wardrobe. So far he obviously only been looking through his mum's side of the wardrobe. After three days a week for three weeks of trying on pretty much everything, Sam had exhausted his mum's collection. Frustrated he looked over to his dad's side of the wardrobe and saw a big box he'd never looked inside of. "Maybe it's where mum keeps all her sexy, slinky lingerie." He thought amused. There would be only one way to find out!
Sam opened the box. There weren't any clothes in there but it was a huge hidden collection of pornography! 100s of magazines and VHS videos. Shocked and very curious, Sam examined the magazines and videos, most of the content was mainstream, the sort of things you'd find on the top shelf of most newsagents back in the 1990's. "Still", Sam thought, "there are more makeup looks I can try and recreate". He flicked through each of the magazines and made a mental note of those looks he could try and add to his repertoire. More pornstar than high-street fashion! The VHS weren't labelled and clearly copies of something, but they could wait.
There was a second box obscured by a few old coats over the top of it. "Oh" mused Sam, "More material!". Expecting more of the same adult glamour magazines and VHS tapes, Sam was shocked but intrigued to find that this box had more very hardcore European titles. His eye's widened and interest piqued. Sam had never seen anything like it before! He kept delving in to this new, more exotic box of treasures and pulled out a handful of around 20 glossy magazines. Sam looked at the title and the explicit image on the front. "TRANSSEXUAL CLIMAX" was the name of the publication, he looked at the second, then the third, then fanned out the rest of the magazines. All of them Transsexual Climax. Sam sat there looking at the images of gorgeous trans girls, some posing solo and others with men.
Up til this point, female makeup and clothes hadn't been an overtly sexual thing for Sam. He'd be lying if he said he wasn't aroused but had never masturbated whilst dressed. Until now that is. Sam was rock hard... so turned on like he had never been before! Sam gorged on these magazines, wishing he was the girls in them. A brand new feeling and another huge step in the transformation and evolution if his emerging feminine side.
For the next week, Sam's routine was the same in terms of makeup and clothes but with the finale being the watching of a VHS. He was delighted to find half of all his dad's collection were trans girls!
This routine had worked perfectly for four weeks now, but something was about to change.
One early afternoon, as Sam was perfecting a smokey eye look borrowed from one of the trans girls in the magazines, he heard the front door creak open. Panic surged through him as he scrambled to hide the makeup and rush in to a bathroom to lock the door. No-one was supposed to be home, but it was too late. His dad, Mark, stood at the doorway, his eyes wide with surprise, scanning the evidence before him: clothes, makeup and trans porn mags, not to mention his son dolled up in full face makeup, bra and knickers and long blonde wig. Silence filled the room, heavy and uncomfortable.
"Sam, what are you doing?" Mark finally asked, his voice a mix of confusion and concern.
Sam's heart pounded in his chest and he instantly felt nauseous. He had always feared this moment, unsure of how his dad would react. "Dad, I... I like wearing makeup," he admitted, his voice trembling. "It makes me feel like myself."
Mark's expression was unreadable, and he took a step forward. "Why didn't you tell me or your mum?" he asked gently.
"I was scared," Sam confessed. "I didn't know how you'd react."
Mark took a deep breath and sat beside him. "I love you no matter what. If makeup and doing this makes you happy, then I support you."
"Please don't tell mum!" Sam begged
"I won't! I won't" his dad insisted. Marissa could be more volitile that Mark, so he fully understand the need to keep the secret.
Tears welled up in Sam's eyes as he nodded towards his dad, feeling some of the weight and guilt lift off his shoulders.
Sam was taken aback, but a sense of understanding quickly washed over him.
"By the way" Mark said, turning around before leaving the room. "You look beautiful, Rachel."
Rachel! She finally had her name.
Rachel smiled her biggest smile, her eyes shimmering with emotion. "Thank you, Dad."
A few day's later, Sam started to find little gifts of girls clothes, underwear, makeup, shoes, costume jewellery tucked away in his wardrobe which enable him to become more authentically Rachel. He knew exactly who they were from and some outfits were replicas of outfits from some of those special magazines and videos that had been discovered! It goes without saying that these were worn at the earliest possible opportunity.
Sam, now Rachel when dressed could embrace her true self. This transformation wasn't just about makeup; it was about embracing identity and living her truth.
Years later, as Rachel looked back on her journey, she realised that discovering his mother's makeup was the catalyst for many more adventures to come.