Imitation Is the Sincerest Form of Flattery

Note: Hi everyone. First time writer here. Hopefully some of you enjoy the start of this story. I've written about 8 chapters atm and have another 20 planned out. If it seems like it's worth continuing I will definitely start posting the rest! I aim to improve as a writer and I would really appreciate any feedback and constructive criticism

Chapter 1

Jake was a 17-year-old in his final year of secondary school. He was a talented football player and one of the star players for his school’s team. Studying wasn’t his strong suit but he was popular and had the confidence to chat up any girl he laid eyes on. He was currently cycling home after a Sunday match with a rival school team.

As he arrived back into the house he was greeted by his mother and her best friend Trish. Jake was not a huge fan of Trish. He got a strong sense that she didn’t like him and on more than one occasion he had caught her giving him an icy stare.

Trish and Jakes mother had been friends since they were young girls. Although to Jake they seemed like very different people. Jakes mother was pretty but conservative in how she dressed. By contrast Trish dressed a lot more provocatively for a woman in her mid 40s. Wearing plenty of makeup, flashy jewellery and never being caught without her hair done. In fact, in all the time Jake had known her he had never seen her dressed down. Today she was wearing a pair of skin tight Capri leggings with a pair of open toed wedge sandals showing off her freshly pedicured red toenails. She also wore a yellow shell top and a pearl necklace. Jake had to acknowledge that she was a very attractive woman for her age.

Much to Jake’s dismay she was sitting smoking a cigarette in the kitchen. Jake hated smoking and even though his mother smoked she was usually polite enough to do so outside. Trish of course didn’t give him the same consideration.

‘Hello Jake’ his mother greeted him with a warm smile and a hug. ‘me and Trish are going out for the evening. I’ve left dinner in the microwave for you’

‘Thanks mum’ Jake responded ‘I’m going to run upstairs and have a shower before dinner. Have a fun evening’

Exiting the shower with a towel wrapped around his waist, Jake headed for his room. The shower was well earned and well needed. His legs were sore and he has been caked in mud from the football match earlier in the day. He was still buzzing over his performance. Garwood Secondary school were one of the tougher sides in the league and he had run roughshod on their defence. If he kept playing in the form he had been recently he would attract a few scouts from the professional teams. Even coach seemed happy. Not that the man ever showed any affection but Jake could tell he was proud.

Jake quickly dried himself off and threw on a pair of boxers. Standing in the full length mirror he gave his muscles a flex. He had a good physique for a 17-year-old. There wasn’t a pick of fat on his stomach and his abs were clearly visible. Although Jake wanted to get to work adding a bit of mass to his frame. If he was aspiring to go professional, he would need to be a lot stronger and less boyish.

He grinned combing the wet hair out of his eyes. Jake wouldn’t consider himself too vain but he certainly felt he was a good catch for any girl. Football prowess aside he had a handsome face with piercing blue eyes. Grabbing his electric razor, he set to work trimming up his beard. It was a bit straggly, being his first attempt at growing a beard but Jake felt it made him appear a bit older and more masculine. It helped with getting alcohol without being asked for id.

Heading downstairs Jake saw that his mother had left dinner out for him as promised. She and Trish seemed to be out for the evening. Grabbing the plate, he lay sat in the sitting room and put on Netflix while he wolfed down his dinner. Before long Jake was a bit bored, and a bit horny. Realizing his mother would be out for the night he grabbed his laptop and opened it up. Turning the volume to mute he loaded up pornhub and found a video to jack off to. A busty young blonde girl lying on a bed and rubbing her pussy. Within moments his cock was fully erect and he was furiously stroking. The element of danger involved in doing this in the front room was also a bit of a turn on for Jake. Having a glance at a few of the side tabs available to him he noticed a thumbnail with an attractive older milf. Caught in the peak of his lust and curiosity he clicked the video and fast forwarded to where the milf had her clothes off.

She was certainly an older woman with voluptuous curves and a slight sagginess to her body. She wasn’t what Jake would have ordinarily found attractive but at this point he was ready to burst. The milf was lying with her legs spread and fingering her pussy at full speed. Jake was obsessed as he pumped his cock. He didn’t even hear the door open. As Trish entered the room.

‘OH MY GOD JAKE!’ she shrieked.

Nearly falling off the couch with shock, Jake spun around. Trish was standing in the doorway of the sitting room and she had a clear view of everything that was happening. Quickly he shut the laptop and looked at her not knowing what to do.

‘TRISH, WHAT ARE YOU DOING HERE’ Jake cried
Trish remained in the doorway for a few moments with a look of shock before her facial expression changed to anger.

‘I came back from the party to get my handbag. But more importantly, you little pervert. What are you doing in your mothers sitting room? Stand up right now’

Still not sure what to do or say Jake stood up to face Trish. He was painfully aware that he was still in his boxers and his cock was still fully erect.

For a moments Trish looked him up and down staring at his cock.

‘Well let’s see what has you so excited then’ she said as she walked to the table and opened the laptop. To Jakes horror, the milf porn was still playing. A young man had now bent the milf over a bed and was having his way with her. Even worse, Jake noticed the title of the video which he hadn’t seen before. ‘Mommie gets naked’.

Again, this seemed to catch Trish off guard as she stood shocked.

‘Well, Jake this really is a surprise.’ She said calmly

‘Trish it’s not what it looks like.’ you cried

‘Really Jake? Because to me it looks like I just discovered you have weird little fetish for your mommy’ she actually giggled ‘Oh my gosh! I wonder how she’ll react when I tell her’

Jake was on the verge of tears at this point. How could this have happened?

‘Trish, please don’t!’ he pleaded as he stood in front of her with only his boxers on. He felt exposed and helpless. His erection was gone at this point.

Trish grinned as she looked at Jake.

‘Ok Jake, we can keep this as our little secret for now. But I want to see you at my house tomorrow at 7am’

Jake nodded in agreement. He was bewildered at why she would want this but if she kept this whole incident a secret then he was happy to obey.

‘Good boy. Now I’m going to leave you to masturbate over mommy fantasies while I get back to the party’ she sneered as she grabbed her handbag from the sitting room

As Jake heard the door shut he immediately grabbed his laptop and stormed upstairs. He was no longer horny. Just angry at himself for being so stupid. He put his laptop on his desk and jumped into bed hoping Trish would keep quiet about the whole thing.

Chapter 2

The next morning Jake awoke early and made his way to Trish’s house as promised. He didn’t go around her place often but he knew the way. Checking his phone, he saw it was 6.55am. Nervously he approached the door and rang the bell.

Within a couple of minutes the door opened and Trish was standing there. Surprisingly, considering the time, she was dressed up to the nines. Wearing her trade-mark red lipstick her hair was styled and she was sporting a floral dress with heels. The woman never seemed to have a casual day.

She smiled sweetly.

‘Jake so nice of you to come by! Come in and have a cup of coffee.’

Jake followed as she led the way into her kitchen. Her house was as meticulously kept as her and her kitchen was a shining example of that. With sparkling clean counters and not one dish in the sink. Jake sat down nervously as she poured him a cup of coffee.

‘Um, Trish, not too be rude but I don’t actually drink coffee’ Jake offered nervously. He wished the woman would just get down to business and tell him what she wanted.

‘Nonsense Jake, I absolutely insist’ she answered as she placed the cup in front of him.

Not seeing any point in arguing Jake took a sip. Just as he expected the taste was foul. Jake often wondered how this awful drink was so popular.

Trish poured herself a cup and sat down beside him at the table. Reaching into her handbag she produced a packet of cigarettes and removed one. She lit the cigarette and inhaled deeply. Enjoying the moment.

Jake hated smoking. He hated the smell and he hated being around it. He had asked his own mother to quit a few times but she hadn’t been able to. At least she was kind enough to not smoke in the house or in front of him.

Trish slowly exhaled her intake of smoke and flicked some ash in the ashtray on the kitchen table. Jake grimaced as he inhaled her second-hand smoke. She turned to Jake and smiled, holding her cigarette towards him.

‘Your turn honey’

‘Trish, I don’t smoke’ Jake said shocked at what was happening.

Trish smiled again.

‘Oh of course. Mister goody-two-shoes doesn’t smoke’ She responded in a sing-song voice ‘but then you probably shouldn’t have been masturbating to that filth in the sitting room either. So maybe you should just do as you’re told or else I will have to tell your mother everything I saw.’

Jake stared at her dumbfounded at what he had just heard. His mind raced trying to work out why Trish would want him to smoke a cigarette. Unable to reach any sensible conclusions he sighed and took the cigarette from her.

As she watched he slowly raised the cigarette to his mouth and sucked on the filter. He felt the smoke fill his lungs and within seconds he was coughing.

Trish smiled and laughed as he coughed.

‘Oh Jake, don’t worry honey. You’ll get used to it’

Getting up from the table she gave Jake a stern look.

‘Now pet, I want you to stay here and finish your coffee and cigarette while I pop upstairs for a minute to get something’

With that she turned and left the kitchen. Jake could hear the clacking of her heels as she ascended the stairs. Sitting alone with his coffee and lit cigarette, Jake was no less confused. He couldn’t believe he had taken his first ever drag of a cigarette and he didn’t want another. He considered throwing the thing away but he didn’t want to disobey Trish.

While he sat alone he continued to take much lighter drags of the cigarette and a few sips of coffee.

Trish was gone for a while and by the time she returned to the kitchen both the coffee and cigarette were finished. Jake was feeling slightly queasy.

‘Good boy Jake. You finished the whole thing’ she grinned

Jake was annoyed at this point.

‘Yeah Trish, I smoked the cigarette. Hope you’re happy. You know I play football, and I don’t want to ruin my fitness with smoking. So, can I please go now’

Trish rolled her eyes. Jake could see she was standing with one hand behind her back.

‘Don’t be such a big baby about it. One little ciggy isn’t going to affect you honey. Anyway, you just have one more little thing to do for me and then you can go.’

Happy that he was finally going to get to go free Jake nodded.

‘Ok, what do you want then?’

Trish placed her hand in front of her and showed Jake a purple pair of panties.
She grinned ear-to-ear.

‘I’d like you to put these on’

For the second time this morning Chris was dumbfounded. Trish was holding up what looked like a pair of her purple panties. Apparently, she wanted ‘him’ to wear them.

‘What! I’m not going to wear a pair of panties!’ Jake shouted indignantly.

Trish gave a look of mock innocence.

‘Really Jake? I would have thought you would relish the chance to get into an older woman’s panties. Maybe it’s only your mother’s that you’re interested in. I suppose I should just tell her’

Jake gave Trish the nastiest look he could muster. He couldn’t believe the way she was twisting things. She was crazy.

‘Fine...’ he conceded as he snatched the panties from Trish’s hands. ‘where in the bathroom so I can put these stupid things on’

‘I knew you were a smart boy Jake’ Trish commented ‘Just head down the hallway to the left. You can leave your underwear in the bathroom. Since you’re wearing mine today’

Walking down the hallway, still feeling angry Jake entered the bathroom and locked the door behind him.

He quickly threw his jeans and boxers off. For a moment, he stopped and considered the absurdity of the situation. It was half 7 in the morning and he was half naked in Trish’s house about to put on a pair of her panties. The woman for the same age as his mother. What possible reason could she have for forcing him to do this? The panties were soft and felt cold. They were certainly a lot nicer feeling than his usual boxers. The had a lace pattern either side and a little bow on the front. They weren’t the kind girls his age would wear. A large part of him wanted to turn tail and run, but he couldn’t let Trish tell his mother what he was doing.

Jake slipped the panties on and pulled the up his waist. They felt comfortable but it was humiliating to be wearing ladies’ underwear. He quickly grabbed his jeans and pulled them on as well ensuring the panties weren’t in danger of peaking over the top of his jean. Jake realised that he would need to be extremely careful to not expose himself at school. The very idea of being caught wearing panties was enough to make him shudder. His reputation would be ruined.

As he re-entered the kitchen she couldn’t resist taunting him again.

‘Well sweety, how are they? I hope they’re comfy enough for you’

Not in the mood Jake responded. ‘They’re fine, can I go now…’

Trish seeming satisfied by the reaction she got walked over and grabbed the waistband of Jakes jeans. Having a peak, she saw that he was in fact wearing her purple panties.

Trish started to giggle.

‘Oh my gosh! I must admit Jake I never thought I’d see you standing in my kitchen wearing a pair of my panties. What would your mother say?’ she feigned a look of surprise before continuing.

‘Of course this is our little secret’ she winked.

Grabbing a piece of paper, she held it out to Jake who took it. The paper said:

SexyTrishaxoxo

Before Jake could ask she explained.

‘That’s my snapchat name honey. To ensure that you’re wearing your panties like I expect you to I’d like you to send me a snapchat of yourself in them at 10 o’clock, 1 o’clock and 4 o’clock. Make sure your face is in the pictures. That way I can be sure that you’re wearing panties all day and not changing into nasty boy underwear’

Again, Jake was shocked at his predicament. He could barely speak, as Trish escorted him to the door.

‘Have a fun day at school Jake’ she laughed as she blew him a mocking kiss

Jake realised he was fucked.

Chapter 3

Jake cycled into school at a snail’s pace, dreading the day to come. He just wanted to get the day over and done with. School was boring and uneventful, outside of his strange predicament. Jake spent the day ensuring his jumper was pulled over his jeans waistband. The last thing he wanted was for someone to see the frills of the purple panties he wore. As 10 o’clock neared, Jake found himself sitting in maths. Asking to be excused, he made his way to the toilets, found himself a cubicle, and dropped his jeans. Angling his phones camera to include his face, he took a picture of his panties and sent it to Trish. It was strange seeing his hairy legs and large package inside of such clearly feminine underwear. Jake didn’t have to wait long for a response.

‘Well done honey! just two pictures left xxx’ came the reply.

In the clear, Jake returned to class. The rest of the day followed a similar pattern, with Jake taking extra care to ensure his secret wasn’t exposed. As Jake walked through school corridor, he had the paranoid sense that everyone was watching him. That was true in the case of one person. Jake locked eyes with Ashley, his ex-girlfriend, who gave him a disgusted look and turned away.

There was no denying Ashley was strikingly beautiful. When Jake had first started going out with her last summer, he was completely enamoured. However, over time he began to realise how little they had in common. Even worse, Ashley was extremely high maintenance. Jake had broken up with her last summer and she hadn’t taken it well. Jake suspected it was the first time anyone had broken up with her. The girl had a serious grudge against him. Jake shuddered at the thought of Ashley finding out about his predicament. She would ruin him. He took another moment to ensure his jeans were hiked up high enough to hide his panties.

He sent another picture to Trish at 1 o’clock as instructed and made it to the last period, science class, Jake’s favourite. Not because he enjoyed science or anything silly like that, but rather because it was the only class he shared with Carly. Jake had a crush on Carly for a long time now and any opportunity to ogle her was welcomed. Jake took his preferred seat at the back right of the class and glanced over at Carly. She was effortlessly pretty with a trim, athletic physique and a tomboyish style. Her brunette hair was tied back in a simple ponytail.

Mrs. Hudson, the science teacher, broke Jake from his daydream.

‘Ok everyone, we’re going to have a bit of a change-up today. I have assigned you all a new lab partner for this semester.’

The class grumbled as Mrs. Hudson started reeling off the new pairs. Jake looked around the room and wondered who he’d be paired with. In all honesty, he got on well with most people but ideally it would be someone smart who could do the work for him.

‘Jake and Carly,’ Mrs Hudson called. Jakes heart nearly skipped a beat as he realised he would be sitting next to Carly for the foreseeable future.

‘Hey Jake,’ Carly said as she smiled and sat down next to him at his desk. ‘I heard the match went well.’

Suddenly, Jake was very aware of the panties he was wearing as he sat beside his crush. What would she think if she knew? They were probably similar to the panties Carly was wearing herself. Jake blushed at the thought as he once again ensured his jumper was pulled down over his jeans waistband. No, he thought, the female underwear he was currently sporting weren’t the kind a young girl like Carly would wear. They were unmistakably an older woman’s. Jake flushed with embarrassment again.

‘Thanks, Carly. We all played pretty well,’ he responded, feigning modesty.

Thankfully, the class stayed busy, which made Jake focus more on his notes than Carly. Once the bell rang at 3 o’clock, he said goodbye to Carly and got out of school.

Cycling home quickly, he made it in before his mother. After grabbing some food and lounging around for a while, Jake snuck up to the bathroom for one last picture in his panties. He snapped the pic and returned to his room, throwing them on the floor in anger. Today was one of the most humiliating days of his life and the fact Trish had caused it made his blood boil.

He hid the panties in his room and threw on a pair of his old boxers. Jake spent the rest of the evening playing Call of Duty and trash-talking his opponents on the mic. It was great to be out of Trish’s underwear and Jake shook his head at how stupid today's affair was. He hoped that Trish had her fun and would leave him alone.

Around 10 o’clock, he got a message on his phone.

‘Well done today honey. See you round mine at 7am tomorrow xxx’

Chapter 4

It seemed a bit like Groundhog Day as Jake returned to Trish’s house at 7 o’clock the next day. He rang the bell and she answered almost immediately.

‘Morning Jake,’ she cooed as she gave him a kiss on each cheek. Today she was wearing a low-cut leopard skin camisole and a black miniskirt with a pair of leopard skin kitten heels that matched her top. Jake noticed her well-tanned skin, clearly the product of a meticulous tanning routine considering she was an auburn-haired woman living in England. Her perfume was strong and gave her an undeniably mature, feminine aura.

Following her into the kitchen, she once again provided Jake with a coffee and lit a cigarette. Jake drank the coffee without argument and took the cigarette when it was offered. Grimacing, he took another drag. Surprisingly, he didn’t find himself coughing up a storm this time, although he doubted that he wanted to get any ‘better’ at smoking. Trish lit up her own cigarette and the two of them sat in her kitchen smoking for a while.

‘So, how did you enjoy your panties yesterday, Jake?’ Trish asked nonchalantly.

‘I didn’t enjoy them at all. I’m not some kind of sissy, Trish,’ Jake responded, feeling a little bit of rebellion well up inside as he realised he had nearly smoked a full cigarette for the second morning in a row.

‘You’re always so defensive, Jake. Ever since I found out you were a little pervert, you can’t take a joke,’ she grinned. ‘Anyway, finish your ciggy, love. We have a busy morning ahead of us’

Jake followed Trish upstairs to her bedroom and she stood before him with a razor and shaving cream.

‘First things first,’ she began, ‘I want you to shave that silly looking thing off your face. I want that face clean and hairless.’

Annoyed but not wanting to argue, Jake took the razor and got to work shaving his prized stubble. It had taken him ages to grow it and he was gutted to see it go. He looked much younger without it and would probably struggle to get served alcohol now. Finishing up quickly, Jake returned to Trish, who gave his face a quick inspection, nodding in approval.

‘Ok Jake, you can take all your clothes off now, honey.’

‘What? No!’ Jake said instinctively.

Trish sighed. ‘You really are a slow learner, Jake. We’ve already been through the fact that I can tell your mother everything I saw you masturbating over.’

‘You know what, fuck it Trish! I’m not going to get naked for you. Tell my mum if you want. It’ll be your word against mine!’ Jake exploded.

For a second, Jake saw a flash of annoyance on Trish’s face. He had called her bluff; she wasn’t going to tell his mother anything.

‘Fair enough, Jake. But it’d be a shame if these pictures I have of you wearing panties were to get out on Facebook. I’m sure that would be extremely embarrassing for a macho boy like you. Why, everyone would think you’re a sissy…’

Jake stood in shock for a few moments. How had he been so stupid? Of course she would save the photos. He absolutely couldn’t let those photos get out. He would become a laughing stock.

She paused for a while to let the weight of her threat fully sink in.

‘Or you could be a good boy and do what your Aunty Trish is telling you to do. And no-one would ever find out anything. Why are you so shy anyway, honey? I’m sure you have nothing I haven’t seen before.’

Realising he had no other feasible option, Jake nodded quietly and began to nervously take his clothes off. Before long, he was standing in front of Trish completely naked. He tried to cover his cock with his hands but Trish shook her head.

‘Keep your hands by your sides, honey,’ she smiled.

Trish gave Jake a full look over from head to toe. She wasn’t shy about staring at Jake's cock and that excited him a little. He found his flaccid penis hardening.

Trish grinned. ‘Look at the little pervert. Getting excited at being naked in front of Aunty Trish. Do you like me looking at your little cock, Jake?’ she asked.

‘No,’ Jake responded, not wanting to meet her gaze. With a smirk, she turned around.

‘Stay here, sweety,’ she ordered as she went into her en-suite bathroom.

She returned with a large pink bottle that had no labels. Handing Jake the bottle, she told him to start applying the cream to his body.

‘Don’t be shy now, Jake. Be a good boy and cover your whole body with this lotion.’

Nervously, Jake did as he was told, lathering up his legs, arms, and stomach with generous helpings of the white cream.

‘Make sure you get the lotion right up in your bum crack as well, Jake. We need it everywhere,’ she commented. Embarrassed beyond belief, he bent forward and slathered some cream around his asshole as well.

‘I’ll get your back for you,’ Trish offered as she grabbed the bottle from Jake, who stood silently as Trish rubbed more cream over his back. It felt good to have her rub his back, but he was still wary of the mystery cream.

‘You’re certainly a handsome young boy, Jake,’ she cooed, ‘Fit and muscular. I’m sure the girls think you’re quite the catch.’

Jake just nodded silently. He wasn’t sure why Trish was complementing him and didn’t honestly care. He wanted to know what the hell this cream was that he was coated in but suspected Trish wouldn’t tell him if he asked.

‘And let’s not forget this,’ Trish said as Jake felt her massage another generous helping of the cream onto his balls. For a moment, Jake was caught off guard but as Trish expertly massaged his testicles, he let out a slight moan of pleasure. His cock was fully erect now. Trish slowly grabbed his shaft with her manicured hand and worked it up and down, covering his cock with the lotion. After a few strokes, she stopped and took a step back, admiring her handiwork. Again, Jake felt extremely stupid as he stood in front of Trish naked, covered from the neck down in the lotion and sporting a full erection.

He thought Trish was going to give him a hand job, but it seemed like it was just another one of her tricks. Jake’s heart was still racing. It wasn’t like he had never had any sexual experiences. His ex-girlfriend Ashley had given him a few hand jobs, but they were never as sensual as the few seconds he had just had with Trish.

‘Oh, sorry to get your hopes up, Jake,’ she smiled evilly. ‘I’m not going to be masturbating you today, you little pervert.’

Jake's face went red as he again looked down at the floor in embarrassment. Trish went to her bathroom and rinsed her hands before returning to the room and lighting a cigarette. She sat down on her bed and crossed her legs, eyeing Jake curiously. After a while, Jake broke first.

‘Well, what now!?’

Unhurried and unfazed, Trish took a long drag from her cigarette. ‘Don’t worry, honey. You’ll find out soon enough.’

After another minute or so of standing around and feeling like an idiot, Jake felt the cream was starting to sting his balls.

‘What the hell? This stuff is stinging, Trish!’

Trish gave a look of delight.

‘Oh good, Jake. That must mean it’s done, then. Go rinse the cream off in the shower.’

Not needing to be told twice, Jake popped in the shower and turned it on. He immediately pointed the showerhead at his genitals.

Much to Jake’s surprise, as the cream was rinsed off it took all his pubic hair with it. The same was true for all his other body hair. By the time he had rinsed off all the cream, he realised that all his body hair was gone, clumped together at the shower drain. His once hairy legs were now silky smooth! In fact, his whole body was, from his chest to his arms to his armpits. Even his pubic hair was completely gone.

Jake was so embarrassed. He couldn’t imagine what everyone would say at football if they saw his hairless legs. As he left the shower, Trish was ready for him with a pink towel. Angrily, Jake snatched the towel and set to work drying himself. Once he was dried, Trish handed him a bottle of pink deodorant and a pair of red panties.

‘That’s women’s deodorant!’ he said incredulously at yet another insult to his masculinity.

Trish smirked. ‘Of course, honey. Today you can wear my deodorant as well as my panties.’

At this point, Jake was ready to break down and cry. He aggressively sprayed himself with Trish’s deodorant and slipped the new pair of panties on. Standing before her, he asked again.

‘Can I go NOW?’

Feigning innocence, Trish responded.

‘Of course, honey. Just remember the rules. I need a snapchat picture of you in your panties at 10 o’clock, 1 o’clock and 4 o’clock.’

Finally, Trish sent Jake on his way to school.

It was another boring day at school for Jake as he once again did his best to hide that he was wearing a middle-aged woman’s red panties. He was also a bit worried that someone would notice that he was covered in woman’s deodorant. Carly questioned his lack of beard when she saw him.

‘I see you’ve given up on the beard, Jake,’ she commented as he sat down beside her. ‘The clean-shaven look suits you, actually!’

‘Thanks!’ Jake responded as he hoped she wouldn’t detect his feminine scent. How would she react if she knew he was wearing a pair of red panties? He shuddered at the thought.

Jake snuck off to the toilets at school when he was required to and sent the pictures to Trish. Mercifully, the final school bell came and Jake took off for home. When 4 o’clock arrived, he jumped into the bathroom and took his last scheduled picture for Trish.

With that completed, he stormed into his room and removed the offending panties, once again hiding them along with yesterday’s purple ones.

Relived to be free, Jake set to work packing his training gear for football. Having to wait around to take the picture for Trish had made him late. Coach would be mad. Showing up late to training was one of the man’s pet peeves, but Jake knew he couldn’t risk showing up to training in panties. Just the thought of his teammates finding out about any of this was horrifying. He left the house, jumped on his bike, and made his way to the training grounds.

As Jake arrived, he saw that everyone was out warming up and stretching. Jake jogged to the changing room and threw on his kit. Once he was changed, he took a quick look at his smooth legs and grimaced. One of his teammates was sure to say something. With a deep breath, he left the changing room and jogged out onto the pitch.

‘You’re late Jake!’ coach barked ‘Run a quick lap then do some quick stretches!’

Not wanting to annoy the coach, Jake did exactly as he was told. Upon returning, he began to stretch his hamstrings with his team.

‘Did you shave your legs, you poof?’

Jake looked up to see Gavin smirking at him. His comment elicited a chuckle from a few teammates. The remaining teammates gave Jake a peculiar look and continued with their stretching.

Jake was mortified and inwardly cursing Trish for making him seem like a sissy to his teammates. Gavin continued to grin, seemingly very amused with his own joke. Jake hated Gavin. He seemed to think that he deserved Jake’s spot on the first team. They played the same position, but Jake was simply better. Gavin rarely got to play over Jake despite spending every training session trying to show him up. Jake decided to ignore his rival and just focus on training.

Later in the training session, the team played a friendly match. Naturally, Jake found himself being marked by Gavin and was being tripped and kicked by his rival's clumsy attempts to tackle him. As Jake ran for a ball coming in from the air, a hard shoulder from Gavin sent him flying. As he lay on the ground, coach shouted.

‘Ease up lads, this is a friendly!’

Gavin ran up to Jake and offered him a hand and smirked.

‘How’d you like that, superstar?’

With a scowl Jake resolved to up his game. The next time the ball came to him, he faked left then took a sharp right causing the incoming Gavin to stumble past him. He then made a full speed dash for the goals. Taking a shot, he connected beautifully, sending the ball to the top left corner of the goal. With a smirk, Jake turned around to see a dejected Gavin looking sour. Coach was beaming.

‘Excellent work, Jake!’

The rest of the game followed a similar pattern. Anytime the ball came to him, he would turn Gavin inside out before either passing the ball on or scoring. By the time Jake was cycling home, he had completely forgotten about his issues.

Chapter 5

For the third day in a row Jake found himself around Trish’s house before school. Once again he was sitting with her drinking a coffee and smoking one of her cigarettes. Although he hated to admit that first drag felt good and the taste of coffee was starting to grow on him. After he had taken a few drags Trish tutted.

‘Honey you’re smoking that like a Neanderthal. Here do it like me’

Trish demonstrated as she held the cigarette between her index and middle finger and brought it to her lips in a feminine manner. Not feeling like arguing Jake did as he was told. Changing the way, he held his cigarette to match Trish. It didn’t feel natural at all and Jake was sure he looked like a total sissy but it seemed to satisfy Trish as she nodded in approval.

As Jake finished his cigarette Trish started giving him instructions.

‘Ok sweety, I’ve left you out a razor and some shaving cream in the shower upstairs. From now on when you come over here in the morning I expect you to shave your legs, armpits and face. If I catch you with any stubble where you shouldn’t have it these darling pictures I have on you will end up on Facebook.’ She finished raising her eyebrows waiting for a response from Jake.

Angrily Jake muttered

‘Yeah sure whatever.’

Smiling at his obedience Trish continued.

‘Be sure to put on some of my deodorant and as a little treat, I’ll let you choose which pair of my panties you wear today.’

Marching upstairs Jake grumbled. He didn’t want to wear any of this crazy bitch’s panties. He hoped in the shower and spotted the shaving cream and a pink laddies razor. Shaking his head at yet another layer of embarrassment he grabbed the shaving cream, lathered up his legs, armpits and face. It took a bit of time before long he had shaven all the area’s he had been told to. Running his hands over his legs he was surprised at how smooth they felt. The cream must include some moisturiser or something Jake thought. He had a quick shower once again being forced to use the feminine products in Trish’s shower. Hoping out of the shower he noticed that all of Trish’s towels were pink. He grabbed one and set to work drying himself off. Finally, he went to Trish’s drawers. Taking a guess, he pulled open the top drawer. He was right first time as he saw an assortment of colourful panties. Not wanting to deliberate on it too much Jake grabbed a random lacy black pair and pulled them on. He finished up by spraying himself with Trish’s deodorant and throwing his old clothes back on.

Arriving downstairs Trish was grinning like a Cheshire cat.

‘It’s great to see you have a proper morning routine now honey. This’ll keep you nice and smooth like a proper lady’

‘I don’t want to be a proper lady!’ Jake snapped

Trish rolled her eyes before approaching him and placing two patches on his arm. Before Chris could ask Trish began.

‘These are nicotine patches honey. I’m going to have you start wearing them every day from now on to get your body craving nicotine’
Alarmed Jake responded.

‘What why!?’

Trish grinned evilly.

‘Well honey, if you’re going to be sharing my panties and deodorant I suppose it’s only fair that you share my nicotine cravings as well’

Shocked but realising the futility of arguing with the woman Jake stood silently. With the nicotine patches applied Trish wrapped some tape around the patches and signed over the top of the tape.

‘This way I can trust you won’t be removing your patches during the day when I’m not around’

Glancing unhappily at the taped patches Jake asked

‘Whatever, can I go now’

Trish smiled sweetly

‘Of course honey. Same rules as usual. Make sure you take those pictures for me and I’m going to need you to come around here after school as well. Say 4 o’clock.’

Jake nodded and got out of the house.

Jake spent the day at school worried about why Trish wanted to see him after school. She was already forcing him to come around her place every morning. Wasn’t that enough? The patches on his arm were another huge cause for concern. He was a serious athlete and couldn’t afford to be addicted to cigarettes. What was this bitch’s problem!? Why was she forcing him to do all this weird stuff? He was already hairless and getting pretty used to her panties. In fact, he barely noticed he was wearing them anymore. Outside of the fact that he had to sneak off during the day and take a selfie in her panties.

After school, he showed up at Trish’s house as promised. She gave him a quick greeting and told him to get in her car. Nervously Jake did as he was told.

During the journey Jake asked

‘Where are we going?’

Trish was quick to respond

‘It’s a surprise honey’

Before long they arrived on a quiet street. Getting out of the car Jake followed Trish as she entered what appeared to be a ladies’ salon. Seeing this Jake gulped, praying that Trish wasn’t going to embarrass him in front of the ladies in the salon.

Much to Jake’s surprise the salon was empty as they entered. Apart from one blonde lady. Jake’s heart sank when he saw her. It was Ashley’s mother!

‘Hello Trish! Hello Jake’ she called as she approached Jake and Trish giving them both a hug and a kiss on each cheek.

‘Hello Elena!’ Trish began ‘How are things?’

‘Oh I can’t complain’ Elena said ‘Just staying busy running the salon here’

She took a quick look at Jake. Elena was also in her mid 40s. Looking at Elena it was easy to see where Ashley got her looks from. She had well styled blonde hair and dressed in a similar fashion to Trish. Being the owner of her own salon she was immaculately well kept for a woman of her age. She was slightly skinner than Trish, not quite boasting the same bust and curves, As the woman Jake had spent the morning smoking with.

‘I can’t believe Jake’s here Trish. Does his mother know?’

Trish smiled

‘Oh no. Mary doesn’t know anything about this’

Elena giggled

‘Oh my! This is so strange’

Jake stood there awkwardly as both women talked about him. Looking around he saw a room full of nail polish and hairdryers and other feminine beauty products. He was terrified to find out what Trish had planned.

Elena gave him a look.

‘Aren’t you lucky Jake! Trish had me close the salon early just to see you. Take your shoes off and go sit in the chair over there. Beside the footbath’

Jake did as he was told and sat waiting for Elena. She returned with a bag of products and sat down beside his feet. He was instructed to place his feet inside of the warm footbath.

After a while she set to work on Jake’s feet filing the rough parts and clipping his nails. Jake had never had a pedicure before and it felt good. Although he was still panicking over what Trish had planned.

Elena picked up a bottle of bright red nail polish and held it up to Trish.

‘Is this the colour you wanted Trish?’ she asked

A quick nod from Trish confirmed that it was. Elena started adding toe separators to Jake’s feet and got the polish ready.

‘Wait, wait!’ Jake said abruptly ‘I don’t want my nails painted, what if someone sees?’

‘Honey, I don’t care what you want. You either do as I tell you or those pictures of you wearing my panties go on Facebook.’

Elena burst out laughing.

‘Oh my god! He was wearing your panties Trish!?’

Jake went beet red as Elena continued to laugh at him.

‘He was Elena. And he’s still wearing them’

Wide eyed Elena took a quick grab at Jakes waistband and peaked at the lacy black panties. The sight of them caused her to snigger again.

‘Wow Trish! What on earth would Ashley think if she found this out?’ Elena gave Jake an angry look ‘She cried for days after you dumped her Jake. I must say it’s a relieve to know that you’re a little sissy who wears panties now. Maybe I should tell her?’

‘No, please don’t!’ Jake cried.

He knew Ashley would spread that info throughout the whole school if she found out.

Trish interrupted.

‘Elena will keep quiet as long as you do as your told Jake. Now be quiet while she paints your toenails’

At this point Jake wanted the ground to swallow him up. He sat and watched in horror as Elena coated his toenails is a bright red polish. Once she was finished the stood back to admire her work.

Trish squealed with delight. Taking off her heels Jake saw that he was now sporting the exact same colour as Trish.

‘Look honey, just like mine’ she grinned as Elena giggled again.

However, Elena wasn’t finished. She went into her bag and grabbed a pair of tweezers. Leaning in close to Jake she started to pluck at his eyebrows. Jake nearly cried.

‘But people will see this!’ he begged

‘Don’t be silly honey, Elena is only shaping them slightly. No one will notice’ Trish responded
After what seemed like an eternity of plucking Elena stood back and grinned.

‘Would you like to see Jake?’ she asked

Jake nodded meekly. Praying that the changes to his eyebrows wouldn’t be noticeable. Elena spun the chair around and Jake came face to face with himself in the mirror. He was shocked. Gone where his thick masculine eyebrows and in their place, were a pair of thin, feminine eyebrows with a high arch. There was no way he could hide this. In the mirror, he could see a gleeful looking Trish. He couldn’t help but notice his newly groomed eyebrows were remarkably like her own. In that moment Jake hated the woman.

They said their goodbyes and Trish drove Jake back to her house. Jake sat quietly throughout the whole journey seething over what Trish had done to him. She gave him a kiss goodbye and said she would see him tomorrow morning.

When Jake got in his mother was waiting for him.

‘Jake pet, where have you been?’ she asked sounding concerned.

‘Uh, Just hanging out with some friends mum’ Jake responded not wanting to be caught with his new eyebrows. Although it appeared to late for that. His mother was looking shocked.

‘What on earth have your done to your eyebrows!?’ she began

‘Erm, nothing mum, I was just trying to shape them a bit and took a bit too much off’

‘Good lord you certainly did!’ she confirmed ‘They look like a woman’s eyebrows Jake’

Upset at the obviousness of his new eyebrows Jake shouted

‘I know mum! Just leave me alone ok!’

Without even bothering to have dinner he ran stormed upstairs hid in his room. Lying on his bed he began to dread school tomorrow. Before long he fell asleep.

Chapter 6

Jake awoke the next day still feeling angry about his eyebrows. Making his way to Trish’s house, as was becoming routine at this point, he wondered how he could attempted to escape her clutches. She seemed hell bent on humiliating him and school today was going to be tough. At least it was Friday, Jake was looking forward to spending Saturday playing videogames and of course his big match on Sunday.

Greeting him at the door Trish was once again dressed in her tight black capris and wearing her wedge sandals showing of her pedicured red toenails. Much to Jakes annoyance he realised that his feet still matched hers. For a moment, he had the horrific image of himself wearing those same wedge sandals. Jake pushed the thought far from his mind.

Sitting down Jake drank his coffee and smoked his cigarette. Again, much to his dismay the coffee tasted good and that first drag of the cigarette was wonderful. Jake closed his eyes and savoured the feeling before exhaling. Realising the nicotine patches were already starting to get him hooked Jake inwardly cursed Trish.

Knowing what was expected Jake went upstairs and lathered his legs armpits and face up with shaving cream. He grabbed his pink ladies razor any ran it over the areas ensuring he remained as smooth as he was yesterday. As he looked down at his smooth legs and painted toes Jake was surprised at how feminine they looked. If he didn’t know any better he would have said they were a pair of woman’s legs. When he left the shower, Trish was waiting for him. She held a pair of black panties in her hands and a pair of matching sheer pantyhose. Jake looked in horror.

‘Now that you have a nice pair of womanly legs it seems a shame to wear those ugly boys socks’ she started ‘So I found you a nice pair of black panties like the ones you chose yesterday and a matching pair of pantyhose to wear today’

Wanting to cry at this point Jake dried himself off and slipped the panties on. He then sat down on Trish’s bed and she showed him how to roll the pantyhose up his legs. The material felt sensual as it rolled up his freshly shaved legs. The pantyhose finished high on his waist and Jake knew immediately that they were going to be tough to hide at school. His red toes shone through the translucent material. Jake took note of this and vowed to ensure his shoes didn’t come off today.

Trish giggled

‘Aww they look lovely on you honey!’

Before she saw him off she removed the old nicotine patches and replaced them with a fresh pair.

Jake’s friend Charlie was the first person to see him. Jake had known Charlie since secondary school. He was tall and skinny with ash blonde hair and he was always sporting goofy smile. Jake wasn’t surprised when Charlie burst out laughing at him.

‘What the fuck did you do to your eyebrows mate!?’
‘Hey! Just shut up about it ok?’ Jake snapped.

Loving nothing better than getting a reaction Charlie continued.

‘Jesus mate, no harm but your eyebrows make you look like a total priss! They look like my mums.’

‘Yeah, I tried to trim them and messed it up ok?’ Jake lied hoping he would buy it

Charlie continue to laugh.

‘Serves you right for getting all metrosexual on us. You need to stop watching Love Island mate‘ Charlie added.

The rest of the day followed a similar pattern with fellow students either point blank asking Jake about his eyebrows or giggling and whispering to the person beside them. Jake was mortified but by the time lunchtime arrived the novelty had worn off and everyone had their fun.

Jakes bigger issue was his pantyhose. He was on constant alert, trying to ensure no-one could see his ankles or the pantyhose protruding above his waistband. The eyebrows he could shrug odd but if anyone knew he was wearing panties and pantyhose he would want to crawl into a hole and die. Even outside of his paranoia the soft, sensual feel of the pantyhose rubbing against his legs was a constant reminder.

Naturally Jake snuck off to the toilets when he was supposed to and sent Trish her pictures. Finally, Jake found himself in the last class of the day. Science. As Carly came over to him, she smiled kindly.

‘You’re talk of the school eyebrows’ she said playfully

Jake rolled his eyes.

‘Yeah, I tried to shape them and kind of messed it up. Live and learn I guess’

Carly smiled again.

‘Yeah you definitely took a lot off them. For what it’s worth I thought your eyebrows were fine’

Jake laughed.

‘Too late now I guess!’

The rest of the class was pleasant as Jake chatted to Carly about his upcoming match. He also found out that she ran a spin class at the local gym and was hoping to go to university to study physiotherapy after school.
Getting home Jake was shocked to see Trish sitting in his kitchen with his mother.

‘Oh heavens Jake! What happened to your eyebrows?’ Trish exclaimed in mock surprise.

Jake gave her a nasty look.

‘I’m glad you agree Trish’ his mother started ‘I honestly don’t understand these new trends but my son having eyebrows like that is a bit strange in my books’

Not wanting to argue Jake told Trish and his mother he would be upstairs if they needed him. Jake played video games in the lead up to 4 o’clock. As Jake went to take his final picture he heard Trish and his mother talking downstairs. Jake couldn’t believe how brazen the women was. She wanted him to send her the picture while she was in the same room as his mother. What if Trish showed her? What would his mother think if she saw him in panties and pantyhose?

Realising he didn’t have a choice Jake went into the bathroom and took his final picture for the day. Soon after sending Trish sent him her reply.

‘Thanks honey! You can take tomorrow morning off. But I’d like you to come see me straight after your football training xxx’

Deflated that he was not going to be able to hang out with his team mates after training. Jake went to his room and throw his pantyhose and panties into the pile with the rest of Trish’s underwear. He threw on a thick pair of socks to hide his toes and spent the night playing video games