A Pansy Among the Thorns

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

What the hell did she want from him, Patrick thought, this was starting to feel completely ridiculous. He attempted to fulfil the request, as Mia waited, hands on hips.

"Thank you so much Mia, these panties are really... pretty. I really appreciate you being so generous."

Mia's expression instantly softened. "Aw, that's OK. I never really felt comfortable in that little lacy pair anyway, but they are pretty aren't they! I bet you'll look cute as a button in them."

"That was a bit better Pat but, we'll have to think about your manners a bit if you really want to suit your lovely new underwear," Cheryl said, thoughtfully. "Now I'm afraid you did still do something very wrong today, and while your sister is a bit of a softie, I think you need some discipline. So I want you to take your little present up to your room, and stay there for the rest of the evening. You can go without dinner tonight. And no computer, no TV, no texting or anything on your phone either. You need some time to reflect, I don't want you getting distracted and forgetting all about our discussion tonight."

Patrick was dumbfounded - who the hell got grounded like this at his age? Who the hell got grounded at all anymore? He looked at Mia for support, but she just looked back and shrugged.

At this point he had realised arguing was a lost cause and, honestly, it would be a relief to get away from this crazy bitch for the rest of the evening, so with a discontented sigh, he turned to the stairs and headed up to his room.

---

Patrick's resentment grew deep and fierce as he lay on his bed that night. What the fuck did these women think they were doing, coming into his home and telling him what to do? He'd considered turning on his computer and playing videogames the moment he got in his room, or calling one of his friends to tell them about the harpies who'd invaded the house, but begrudgingly the boy thought better of it. There was no point in inviting further conflict tonight. He could begin his counter-campaign in the morning.

Patrick had no clue what that bizarre psychobabble Cheryl and Mia had been spewing about gender roles was, but one thing he knew for a fact was there was no way he'd be wearing any panties any time soon, or doing any other girly rubbish. Just the thought of it made him shiver. Imagine if his friends saw, if Samantha saw! He'd literally never live it down: the boy in panties? No, she was probably only trying to scare him, but if Cheryl ever started giving him that feminazi crap again, he'd tell her exactly where to shove it.

He resolved to do everything in his power to split up this engagement for good. Patrick loved and respected his dad, but the man clearly couldn't see what a controlling, nasty woman he'd fallen for. Ultimately, the boy reasoned, Patrick would be doing his dad a favour by breaking them up. Even though he obviously couldn't talk about what had happened this evening - that would mean revealing the shame he'd gone to such painful lengths to avoid his dad ever learning - he was still confident that with a few father-son heart-to-hearts, he could convince his dad Cheryl was bad news.

Despite the fact it was only 10pm on a Friday, Patrick was exhausted. The whole affair with Cheryl and Mia had torpedoed his evening, but the boy was still determined to have a good weekend. It was the start of summer after all! Tomorrow night he'd kick back with a few of his boys, crack open a beer or two and maybe watch a movie (he'd definitely show them Mia's panties, although that would be the only part of this evening the boy would care to talk about). The first thing he'd do when he woke up though was call his dad for a 'chat'. Hank was a wilful guy and Patrick knew he'd need to get the ball rolling quickly if he wanted to break up this engagement by the time his father returned in a couple of months.

He didn't have to worry about that 'til tomorrow though, for now it was finally time to get some rest. As he dozed off, Patrick smiled, looking forward to a long lie in the next morning.

Pt. 4: Patty

Patrick awoke to the sound of his curtains being pulled apart sharply, followed by two quick claps. The boy felt groggy and confused; what was going on? He hadn't been woken up by anything other than his own alarm in more than 10 years at this point.

"OK Sleeping Beauty, up we get now. You've got a busy day ahead of you!" A cheery voice rang out. Slowly, Patrick's eyes cracked open and the first thing he saw was Cheryl, standing by the window. What was her problem?!

"Cheryl..." Patrick began sleepily. "Why are you in my room? It's Saturday morning... get out of here."

Cheryl strode over to the boy's bed and pinched him on the cheek, hard. "Alright dear, clearly you didn't listen to anything I said last night, so let me make something very clear. Deceitful little boys who like to slip into their sister's panties simply must experience all the delights that usually only us women 'enjoy'. It's going to be a long and challenging process to help you become the swishy, girlish little darling you're desperate to be - but I promise: I won't stop until I've ensured you reach your dreams."

This was not happening. Patrick had had enough, there was no way he was going to listen to another word of this woman's nonsense. "Listen, Cheryl!" He shot out of bed, standing tall and squaring right up to her... chin?

In a moment, he surveyed the woman in front of him. He felt as though he'd never taken the time to really look at Cheryl before - she was in her 50s, who cared what she looked like - but now, standing right in front of the boy, she cut an imposing figure. Like her daughter, she stood a fair few inches taller than him, and her frame was broader than he had thought. Her dark hair was tied in an austere bun, and she wore a pair of straight black trousers and a crisp linen shirt that looked both more formal and more masculine than made sense right now. The boy was suddenly acutely aware of the fact he had nothing more on him than the boxers he slept in, and involuntarily, shrunk back from his challenge for just a moment.

Cheryl slapped him. In genuine shock, Patrick turned his head back towards her in slow motion. No one had ever smacked him before, not even his dad. Tears began to form.

"Like I said Patty, we've got a long day ahead of ourselves and I don't need you wasting any more time. Usually I'll want you up a little bit earlier than this, but I've let you lie in until 8 this morning since you had a tough night. Now get these on," she pointed to the pair of panties on the chair. "And come to Mummy's room, I've got some things you can wear for now."

"I... Patty? Wait, Mummy?"

"Oh yes. Patty was Mia's idea. We agreed Patrick was much too serious and harsh a name for a boy of your... sensibilities. Patty is so cute and fun, Don't you agree?" She didn't wait for him to respond. "And, of course, little girly boys must always address their Mummy properly. Remember what I told you last night. Being feminine is a lot more than just wearing panties - it defines how you talk, how you behave, everything really!" She shot him a cheerful smile and started walking out of the room. "See you in a second, don't dawdle now. And try not to make too much of a racket, your sister is still sound asleep!"

Patrick wanted more than anything to shout after her exactly where she could shove those panties, but he was beginning to realise just how dire his situation was. Ruefully, he looked at the underwear once again. How could one, tiny mistake have got him into all of this? It wasn't fair. He could only pray Cheryl was exaggerating and would grow tired with this game quickly. Maybe a bit of contrition would help the process along...

Taking care not to step too heavily, Patrick crept across the landing towards his dad's room (he could hardly believe Cheryl had already settled in so confidently as to call it hers) and pushed the door open. "Mummy," he cringed, "I'm sorry about last night, can we talk about -"

"What are you wearing? Did I not just tell you to put on the panties before coming in here?"

Patrick bristled. He had put on the panties, wincing as he pulled the soft, tight fabric up his legs until it rested snugly around his waist, and the thong nestled in his bottom. Surely she hadn't expected him to walk across the landing in just a pair of panties though? Of course he'd put on a pair of jeans and a t-shirt over the top.

"Ummmm, sorry - Mummy, I just, I'm wearing them underneath!"

"O....k then, why don't you take off those silly clothes and show me?" Cheryl gestured towards his top dismissively.

Patrick couldn't believe what was happening. With as much reluctant defiance as he could muster, he pulled the shirt and jeans off his body, and in a moment, was standing in front of Cheryl wearing nothing but the red thong panties he'd taken off the hamper yesterday.

Cheryl placed her hand over her mouth and turned away for a second, stifling a giggle. "Sorry dear... you look very pretty. Mia was right, they do suit you better. Now, I've got your clothes for today all nicely laid out for you here, but I'm afraid you're not quite ready yet."

Patrick hadn't clocked it when he first entered, but looking atop his father's bed now, he saw a pair of powder blue pants with no buttons, as well as a silky white shirt with a matching blue flower pattern on it. At the foot of the bed there was a pair of white leather shoes with a strap across the front.

"I know, I know sweetie. I'm sure it's not quite as feminine as you'd like, but we have to start somewhere, OK? Before you can put any of that on though, we're going to need to sort out that body hair."

Before Patrick could even protest the idea of putting on the stupid-looking outfit, Cheryl was pushing him into the en suite bathroom. She grabbed a light pink razor out of the cabinet, using it to point the boy towards the shower. "Now luckily, you're practically hairless already - unlike your father - but I want you coming out of this bathroom smooth as silk, do you understand?"

Patrick had been shaving his face for years and had even shaved his pits once, just to see how it felt, so he knew he could do what she'd asked, but the idea of denuding his entire body of hair was just, ludicrous. "I... what if I want to wear shorts?" This faintly ridiculous protest was the only thing that came to mind.

"Well Patty, then I suppose you'll get to show off your lovely smooth legs," Cheryl responded, smiling cruelly. "Now get on with it." She slammed the bathroom door behind her.

--

Half an hour later, Patrick emerged from the bathroom, smooth as the day he was born, aside from the hair on his head. While he shaved, he'd wracked his brain for some kind of reasonable explanation he could give to Samantha, should she ever ask him to take his clothes off. Nothing believable had come to mind, he just had to hope she wouldn't ask until it grew back. A young man praying his girlfriend didn't ask him to take his clothes off, he thought sourly. Patrick swore to himself once again, there would be consequences for what this cow had done to him.

"Oh now that's much, much better! Remember, even if you don't have a lot, any hair below your eyebrows is unacceptably masculine Patty, so I expect you to be beautifully shaven every day." She passed him a pack of razors like the one he'd just used to remove his body hair. On the front of the plastic package was an image of a laughing woman in a bikini on the beach.

Patrick could assure her he would not be shaving his legs ever again, let alone every day, but he kept his mouth shut for the time being and tried to look apologetic.

"Now it's time to get you dressed!" Cheryl clapped her hands together and pulled the pantied boy over towards the bed. He had been dreading this, and attempted to offer up some light resistance, but the woman was stronger than she looked, and had no trouble shoving the boy halfway across the room. In fact, it didn't even seem like she'd noticed him trying to resist. "Step forward Patty," she said, holding the pair of trousers in front of him. Even if it was a bit of a childish colour, the trousers didn't seem too bad, so Patrick stepped into the garment. In a moment, Cheryl pulled them up, and the boy instantly realised the pants reached up to his belly button, while the ankle cutoffs felt higher than he was used to.

"Aren't they lovely? The high waist really elongates your legs while giving you nicely defined hips. Pay attention dear, these are exactly the kind of things you're going to be thinking about a lot!"

But Patrick was distracted from Cheryl's bizarre reasoning as she'd already started pulling the shirt down over his chest as well. He felt a twinge of embarrassment at the feel of the silky material making contact with his skin, and at the embroidered flower pattern which adorned the shirt. He tried to think about those big guys at the beach who wore the Hawaiian shirts - this was basically the same thing right?

"Now we just tuck it in here and... there!" With that, Cheryl sharply pulled up the zip at the back of the trousers and fastened the clip at the top. Finally, she had him step into the white shoes which she called 'Mary Janes' (Patrick cringed at the name), before ushering the boy over to the full length mirror on the wall.

This was bad. He looked nothing like the guys at the beach... he looked like a fairy! The trousers had made his already skinny legs look even longer, while the top's shallow V-neck and draped shoulders somehow minimised the small muscles he'd managed to build in his upper body. His cheeks flushed bright red with embarrassment as he tried to turn his face away. Cheryl quickly leaned in over his shoulder and grabbed the boy's chin, pulling his face back towards the mirror. "Well, well, this is such an improvement on that scrappy little man from last night, isn't it? Your first taste of real femininity and I can see you're already blushing with excitement. That's wonderful, because today we're going to the outlet to really fill out your wardrobe with some lovely summer pieces!"

She couldn't be serious - there was no way Patrick was leaving the house in this get-up. He already felt like some kind of fag, but if anyone saw him in these clothes, his life would be over for sure.

"Mummy I'm not so sure... I'd feel awfully embarrassed if anyone saw me like this..."

"Oh, Patty, you're right, I'm sorry! One second..." Cheryl walked over to her drawer for a second and came back holding a white Alice band with a small decorative blue flower on one side. She quickly placed it on Patrick's head, arranging his hair neatly around it. "Much better. You were right, the ensemble was incomplete - now you're ready to show the world the new you!"

If he felt awkward about the outfit before, the boy was apoplectic now. The hairband looked like something a little girl might wear! He decided, one last time, to swallow his pride and allow Cheryl to lead him out to the car. There was no outlet in town, which meant wherever they were going, it was very unlikely anyone he knew would see him. Hopefully, if he showed himself willing to accept his punishment for today, Cheryl would see she'd been completely wrong about him and finally chill out. Then he could get on with the business of splitting this awful relationship up.

For now though, he sat in the front seat of the family Range Rover and let 'Mummy' fasten his seatbelt. "I'm sure Mia would have liked to come but, no sense in waking her up early on a Saturday is there? We can show her your haul when we get back."

Patrick noted bitterly that it had clearly been fine to wake him up early on a Saturday, but kept his mouth shut, now concerned with what exactly Cheryl meant by showing off his "haul". They weren't seriously gonna buy anything for him, were they?

Pt. 4b

The drive took a while (although not as long as the boy had hoped - he wouldn't feel safe until he'd crossed a border dressed as he was) but eventually Cheryl came to a stop outside a large, modern looking shopping mall. Patrick's heart pounded in his chest - he'd never even crossdressed for a party or Halloween before, Hank had always strongly discouraged any genderbending even as a joke - and now he was about to step into a busy shopping centre, on a Saturday, dressed like a total fruit. He took a deep breath and braced as Cheryl opened the passenger side door and beckoned the boy out.

Once inside, Patrick tried to keep his head down and walk as quickly as possible, but Cheryl grabbed his hand and pulled him to her side, saying loudly enough for passersby to hear: "Hey! I put a lot of thought into that ensemble young man, you should have some pride in your appearance!" Giggles erupted from their fellow shoppers. From then on, Cheryl kept a tight grip on the boy's hand, regularly fussing over his hairband as they walked. He felt completely ashamed; a dainty little flower out for a day at the mall with mummy. Seemingly everywhere he looked there was someone staring, pointing or snickering - he was just relieved he didn't see anyone from school.

Patrick breathed a deep sigh of relief as he realised she was pulling him away from the crowded mall thoroughfare towards a shop. This relief lasted until the exact moment they stepped inside and he saw the merchandise. Wall to wall, clothing racks and displays showcased all the latest in female fashion. Blouses, pants and jeans, even a few dresses and skirts hung around the place. Patrick's face dropped.

A pretty woman, maybe a few years older than him, approached. "Hi gir- guys!" She faltered briefly as she clocked Patrick's gender, but kept a chirpy tone of voice. "How can I help you today?"

Cheryl smiled sweetly. "My son here has told me he'd like to explore his 'feminine side'. He practically insisted we come out today and have a look at your beautiful range. Would you maybe be able to help us pick out a few pieces for his wardrobe refresh?"

"Of course!" The girl smiled encouragingly at Patrick. "I'm sure we have a lot of items you'll just love, sir."

Patrick wished he could disappear as the girl took his other hand and led him through the shop towards a dressing room. "Now, you just wait here and I'll be back with some stuff I think might suit you. In fact, why doesn't mum come with me, she can help me really get your taste."

Over the next hour, Cheryl and her new friend brought Patrick outfit after outfit after embarrassing outfit to try on. Velvet shorts with pretty ankle socks, silk wrap tops with puffed sleeves; at one point they had him strut out into the centre of the store wearing a cropped mohair sweater and skirt set, (where he was pretty sure a girl took a picture of him on her phone). The experience was utterly mortifying, and the boy was shocked anew when Cheryl placed an enormous pile of the garments on a counter and told the girl, "He'll take them!" Where was she even gonna put all of this stuff?

"Aww, wonderful!" The girl gave Patrick a cute smile while ringing up the order, before handing him the huge bag and waving to the pair as they walked out.

"Now, hold the bag in the crook of your elbow - like this, see? And put your forearm up, there, don't you look sweet with your lovely new things," Cheryl smirked at the boy as she took his other hand in hers again.

"Look, whatever Cheryl, can we please just get this over with." Patrick was feeling incredibly sorry for himself after the humiliations he'd just endured and wanted nothing more than to get home and finally change out of this stupid outfit. He was still planning to hang out with his friends tonight - there was no way he could be dressed like this when they arrived.

"Don't fret Patty, we're nearly there now. There's just one more thing we need to sort." Cheryl came to a standstill. Patrick looked around for a moment in confusion, and then he saw it. In front of them was an upmarket Italian lingerie boutique: Intima. He remembered coming to this outlet as a younger kid with some friends and being dared to walk into the shop as a joke.