Imitation Is the Sincerest Form of Flattery (part 3)

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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

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Comments

Poor Jake!

Oh Lily! What are you doing to poor Jake? I feel so bad for him.Jake isn't just a boy. He is a real boy- not a sissy. For Heaven's sake, he even had mossy stubble on his chin. You've already ruined his life. At this rate, it will become impossible for him to salvage his macho life. Where will this leave him, Lily?

I understand why Jake succumbed to Trish's demands. He couldn't allow her to tattle to his mother about the MILF videos he was watching. His mother might think he had a 'thing' for her, and there is nothing more disgusting than incest. Anything would be better. It might even be better if he allowed his mother to think he was dressing and smoking like a woman because he wanted to be just like her. I know I would do this if I were Jake.

Regardless of the damage this causes, Jake will need to pick himself up and make the best of his life, even if he winds up becoming a middle-aged chain-smoking woman. Who knows? Perhaps he might find a nice middle-age man with children to become his husband. What better way to prove to his mother that he really wants to be like her rather than bed her.

Thanks for the story, Lily. I'm enjoying it tremendously.

Hugs,
Sharon

Wow, I'm honestly flattered

Wow, I'm honestly flattered you like my story.

I'm a massive fan of your 'like mother like son' series and it was a pretty big inspiration for this story

Again I'm glad you're enjoying it so far and rest assured Trish has a lot more in store for Jake!

Another inspiration?

I also see some Karin Roberts in your work, when it comes to Trish. I like Karin.

Hugs,
Sharon

Wow

This is great - I can't wait for the next chapter

this is one of my favourites

this is one of my favourites stories ever
that's why i would like to ask if you have in mind to continue?