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.