Imitation Is the Sincerest Form of Flattery (part 1)

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 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:


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.

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