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In Sheep's Clothing

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Adrian looked up nervously. The long blonde locks of the wig tickled his cheeks, and his lips stood out like a red light during rush hour. He blinked and the girl in the mirror did the same, with unnaturally long eyelashes fluttering lightly as she did so.

"There, look at how pretty you are", a soft, high-pitched voice chirped next to his ear, and another girl smiled at him from the mirror. "Come on, give me a smile! Aren't you excited to meet my friends?".

Adrian fidgeted with the hem of the skirt he was wearing, trying to pull it down and cover more of his thighs. His legs were fully shaved and they just felt so bare and exposed, his heart racing and his throat clamping up from the anxiety. He would probably feel the same even if he'd been fully clad in a Catholic nun's tunic, but the ridiculously short miniskirt certainly didn't help.

The girl next to him - Annie - pouted, one of her hands sliding inside his open shirt and underneath his bra to pinch and pull on one of his nipples until he cried out in pain.

"I said -" she hissed into his ear, before biting down on his earlobe. "- smile".

"Ah!", he yelped, forcing his lips to curve upwards and biting his tongue to keep himself from whimpering, shaking in place as her fingernails dug into the sensitive skin of his nipple, her fingers slowly twisting.

"Aww, see how much cuter you look like that?", she cooed, rubbing her soft cheek against his and chuckling before mercifully sliding her hand out of his shirt to wipe a small tear from the corner of his eyes. "Don't ruin your makeup! Good thing it's waterproof... we don't have time to fix you up, we're already late!".

Annie grabbed his hand and pulled, and for a second Adrian felt as if he was glued to his chair, but her blue eyes narrowed into a silent threat and he swallowed hard, forcing himself to stand up even as his legs trembled like those of a newborn fawn.

"Come on, we have to hurry!", she insisted, and he did his best to keep up with her pace while praying to any god that might be listening that his ankles would not twist or he would not slip on anything on his way.

The high-heeled shoes he was wearing felt too tight and too unstable, but they were the shortest ones he was allowed to pick. He had no doubt that she knew he would choose them, because it seemed like she went out of her way to choose the sluttiest-looking ones she could find. He'd been tempted to pick one of the more modest-looking pairs but there was no way he could walk in them without tripping after the first few steps, and as humiliating as those shiny red pumps were he knew that she would make it so that his ass turned an even brighter red if he dared to trip and make her fall as well.

Her hand felt warm and soft but her grasp was iron-tight; he knew from experience that she was a lot stronger than she looked, but even if she hadn't been he wouldn't have been able to go against her. Not when she had that video of him...

His stomach clenched, he didn't want to think about what would happen if she were to spread it around but it was the only reason why he didn't resist as she opened the door and dragged him outside where everyone else could see him.

As they walked down the street he could feel everyone's eyes on him, as if they could see right through his disguise, and they were surely judging and thinking to themselves that he had to be some sort of pervert.

And the worst thing was, the more shame he felt the more he could feel his cock straining against its metal cage, as if he needed further proof of how much his body had been defiled and trained to meet her depraved tastes.

"You should be grateful", she had said before, as she'd turned the small key in the lock, pulling and tugging on the straps to check that everything was holding up as it should. "Wouldn't it be embarrassing if everyone could see how much of an exhibitionistic little slut you are?".

As much as he had hated her then, now he did feel a little bit grateful, because he knew there would have been no way to hide it. He wasn't even sure that the short, flimsy fabric of the shirt would be enough to cover it up if it did get hard.

His high heels were clicking against the pavement, a light breeze blowing through his skirt and his free hand grasped on its hem again, terrified at the thought that someone might find him out. As paranoid and anxious as he was, once they'd walked past enough people he had managed to calm down a bit and realize that they really couldn't tell he wasn't actually a girl.

He didn't know how, as he was sure that it was obvious, that there were a million things that would give him away. Still, the only ones who openly looked at him were men who did so with a lecherous expression that indicated they had no suspicion about what was hiding inside his silk and lace panties, underneath the chastity cage he'd been forced to wear.

"Come on, we're almost there!".

She sped up suddenly, making him almost trip for a second, but he somehow managed to regain his balance and keep up with her pace.

It seemed they were headed towards a café, which looked quite fancy and absolutely non-threatening, but his stomach was tied in knots as if she was dragging him to the gallows.

He didn't know what she was planning but whatever it was, it couldn't be good. Besides, she herself was living proof that you can't judge from appearances, as Annie's angelic face and petite exterior were in fact nothing more but the carefully-crafted mask of a deranged sadist. He couldn't trust the fact that she was bringing him to a public and innocent-enough-looking place to mean that something horrible wouldn't be expecting him inside.

She pushed the door open and a bell twinkled, announcing their presence to the current patrons.

Two of them - two girls sitting at the same table - perked up and smiled at Annie, and one of them waved her hand at here.

"Over here!", she cheerfully announced, her black curls bouncing a bit as she pushed herself up on the chair.

"Oh yay! You've picked my favourite spot!", Annie said in a delighted tone, dragging Adrian along with her and pushing him towards the seat that was in the middle between her friends' as soon as the girl that had spoken had moved her bag away from it.

Adrian obediently sat down and winced as the sitting position and the shift in weight caused the dildo that was currently lodged in his ass to press against his prostate, making his trapped cock twitch again.

He could feel those girls' eyes on him as they leaned in closer towards him, prompting him to slouch and uselessly try to pull his skirt down again, the frilly fabric rising up dangerously in that sitting position. He was incredibly aware of the sweat that trickled down his neck, the air felt much hotter than it actually was and his head was roasting underneath that wig.

His legs were crossed, both to make sure his crotch would be hidden even if someone managed to glance under the skirt and to try and hide how much he was trembling.

The girl with black curls chuckled and grasped on his chin, forcing him to look at her. Her face was cute, with dark brown eyes and a slightly upturned nose, and her skin was a vibrant mahogany shade. Still as she smiled he could feel nothing but dread, even if he did not dare to move or turn away.

"He looks so cute!", she said, lowering a voice a bit so that the people around them could not hear.

"He's just like a doll!", the other girl said, taking his arm and stroking it with a delighted expression on her freckled face. "His skin feels so smooth... and did you do his nails yourself? They look great!".

She raked her long acrylic nails against his forearm, making him shiver, and chuckled softly as she saw goosebumps appearing on his skin.

"Thank you, Claire! That color really suits him, doesn't it?", Annie said, looking at his bright red nails - almost the same exact shade as the shoes and lipstick he was wearing.

"He has such nice legs too, I'm almost jealous!", the dark-skinned girl said, letting go of his chin to place her hand on his knee, sliding it towards the inside of his thigh.

He glanced up at Annie in panic, but she glared at him and he gulped loudly, forcing himself to uncross his legs and spread them a little.

"You can touch him as much as you want, I've got him all caged up", she reassured her friend, who didn't hesitate to slip her hand further and further up along the inside of his thigh, making a cold shiver run down his spine.

He knew that he should have felt thrilled to be touched by such a cute girl, that it should have been some kind of silver lining in his nightmarish situation, but in truth those unwanted avances did nothing but make his skin crawl.

"Amanda, you're so shameless!", Claire whispered and chuckled, but her friend did not seem to care, her fingers digging into the soft skin of Adrian's thighs until he had to bite his lip to hold back a small whimper.

"Have you already played with him?", Amanda asked Annie, who grinned as she pulled out her phone.

"Do you want to see?".

Adrian's stomach clenched and his anxiety skyrocketed, his hands clenching up into fists as Annie opened up her hidden folders and scrolled through a large number of pictures of him in all sorts of degrading situations and in much skimpier clothing. She tapped her fingers on one of them and there he was, tied up and helpless as his ass was displayed on the screen, barely covered by a thin see-through thong which was pulled aside so that the large vibrator inside him was fully visible.

Amanda and Claire oooh-ed and gasped, a slight flush appearing on both of their faces. As for him, he was sure his face was beet red and he had to fight back the urge to cover it with his hands, or to snatch the damn phone away and slam it against the table until it broke.

His anger and shame were bubbling up inside him as the three girls looked through more and more of those pictures, each one seemingly more humiliating and perverse than the previous one. He was biting his lip so hard that he was sure he must have broken skin, fingernails digging into his palms until he felt a couple of them break.

The pain was only a small distraction, but he welcomed it nonetheless, especially as Amanda and Claire's hands slipped underneath his clothes to rake their nails against his back and to pinch and tweak his nipples, making his body react in contrasting and confusing ways.

In the meanwhile, Annie was telling the two about some of the instances in which those pictures were taken, making him wish the ground would just open up and swallow him whole so he would not have to bear any more of that torment.

"This one time was really fun, he was making a lot of noise so I had to gag him because my neighbours were home, I wish I had recorded some of it sounded really funny!", she related as she stopped on a pic in which he was looking up at the camera with a desperate expression, face flushed and drool oozing out from under the large ball-gag he'd been forced to wear.

"Ooh, this one! This is when we first tried out the nipple clamps. They were so sore and sensitive in the end that they'd get hard even just from his shirt brushing them, the next day in class he looked like he was really struggling... I always make him wear bras now so that they don't show through, and this one time I put the clamps on him before we went to the lecture and had him keep them on underneath the bra for the whole morning. Oh he looked so pitiful, I had him begging me to take them off and then when I did he squealed so loud! It turns out they hurt even more when you take them off than when you put them on!"

(Amanda and Claire played with his nipples even more after hearing that, pulling and twisting and pinching them until he had to bite on his fingers to hold back his cries, his cock once again twitching and straining inside its cage).

"This one is cute, right? I didn't allow him to go to the toilet for the whole day and then I came over to his place and he was pretty much crying 'cause of how bad he had to go, and like his little sister was there you know, so I chatted with her and meanwhile he stood there with the funniest, most desperate face! And I just kept talking and talking and blocked his way, and he couldn't just ask me while his baby sister was right there and I pretended not to understand when he whispered or tried to talk his way around it... and then, oh, oh man I just can't - I'm laughing again just thinking about it! He just- he fucking pissed his pants there and there was no way his sister wouldn't notice, and I pretended to be shocked and all worried while she had the most disgusted face... fuck that was priceless! After she ran away he had such an adorably miserable expression that I had to take a pic of it. He just looks like a poor kicked puppy, doesn't he? So cute! I kinda wanted to make it my phone background but then it would be kind of awkward, you know, with my boyfriend and all".

Adrian forced himself to endure, his only relief coming from the form of a waiter that would occasionally walk up to the group and cause them to turn the phone around and quickly move their hands back to more neutral territory, albeit by that time even just feeling their pressure on his knee or his shoulder was enough to make him nervous.

"Maybe you should send him a pic of him now, looking all cute and flustered", Claire suggested with a mischievous grin.

"He makes such a cute girl, though, you should be careful... he might steal him from you!", Amanda warned, making the other two giggle loudly.

"Maybe I could get him to fuck him, if he was drunk enough", Annie said, as if thinking out loud. "He's not exactly the smartest guy even when he's sober. That'd be kind of funny too, I'd definitely want to take pics!".

All three of them laughed at that, while Adrian looked at her in horror. He wished he could say she couldn't possibly mean it, but he was terrified to be proven wrong.

"Wow, it's getting late!", Annie noted after a few more minutes. Adrian couldn't help but hide his relief, eager to get away from them all and take a shower to clean that stuff off of himself and to try and get rid of the lingering feeling of unease that their touches brought him.

Unfortunately, his relief was short-lived, as right after that she clasped her hands together and smiled, her blue eyes lighting up as she looked back at her friends.

"Well so, did you two want to play with him?".

Adrian felt his heart sink into his gut, his whole body freezing as if he'd been dumped into an ice-cold lake.

"Hell yeah!", Amanda eagerly replied, while Claire responded with a more lukewarm "Yeah sure, why not".

No, no, no, no... it could not be happening, it couldn't!

He stared at her and pleaded silently, his words stuck in his throat as their eyes met and her kind-looking smile turned into a much more sinister one.

"Let's go then!", she said, getting up and waiting for the rest of the group to follow.

"We've got to pay first", Claire pointed out, and Annie's grin widened.

"Oh he'll pay... won't you, my pet?".

Adrian swallowed hard, fingernails digging into his palms again as he smiled meekly, his vision slightly blurry as the tears pooled up in the corners of his eyes.

"O-of course".

He felt his heart pound as he looked for his wallet in the shoulder bag, his hand shaking so much that he could barely take out his money.

"Oh, he's so obedient", Claire whispered in an admired tone, and Annie giggled in response.

"Just wait and you'll see!".

Adrian was shaking like a leaf in the wind as the two girls undressed him, untying the front knot of his shirt and unzipping his skirt so that they could pull them off of him, leaving him with his silver-and-black panties and matching bra, and a black garterbelt holding up his semi-transparent black stockings.

"Get on your hand and knees", Annie ordered him, giving him a cold threatening glare when he whimpered and hesitated to obey, until he finally forced himself to kneel down on the bed and expose himself to their hungry eyes.

"Wow, that's pretty big", Claire commented, pulling his panties aside and spreading his buttocks to have a better look at the dildo that was lodged inside of him, the flared base preventing it from being swallowed up completely and disappearing inside his body.

"Oh yeah, I've been stretching him out a lot, I couldn't even get one finger in at first", Annie said, taking out her phone and snapping a picture before slowly pulling out the large toy, leaving his hole twitching from the sudden emptiness.

"What a nice ass", Amanda said with an eager tone as she was adjusting the straps of her harness, waiting for Annie to pass her a small vial of lube before smearing a generous quantity of it on the ridged strap-on that she proudly wielded between her legs.

Adrian could do nothing but wait, silently praying for a mercy he knew wouldn't come as her small fingers slid inside his already-prepared entrance, using the leftover lube to ease her task. She prodded and poked and stretched and he clenched his teeth to hold back his protests as well as his cries, his cock responding to those attentions against his will every time her fingertips brushed his prostate.

Adrian tried to hide his face, especially as he heard Annie take more pictures, but Claire grasped on his firmly-attached wig and forced him to look up again, rolling up her skirt and pulling down her panties to expose her pussy. Below her ginger-blond pubic hair, her folds were a bright, almost strawberry pink colour, standing out against her pale skin.

"I'm sure Annie taught you well, so, get to work!", she urged him, tilting his face up and pushing herself against it, gasping loudly once he reluctantly pulled out his tongue to start licking. The sharp, tangy taste was much stronger than Annie's, almost metallic in nature, but aside from scrunching up his face he did not dare to show his discomfort as he worked to pleasure her as skilfully as he could, knowing that he would be punished if he didn't.

By the time Amanda pulled out her fingers and lined up the tip of her strap-on with his hole, he could do nothing but let out a muffled cry as she slid it in with one swift motion, barely encountering resistance.

"Ooh, it really slides in!", she said, grasping on his hips and shaking her own at a slow pace at first, as if testing the waters. "What an eager, cock-hungry hole!".

"It's getting a bit loose, yeah, but I'm trying to make it so that he can take a whole fist soon", Annie explained, her words causing Adrian to tense up in fear. "I've found this website with like, rich old guys looking for crossdressers and there's this one dude who really liked his pictures but he's only into fisting. I guess he can't get it up anymore or something? Whatever. Anyway he's willing to pay like three hundred bucks for his ass so I really want to get him ready for it. There's this dress on sale now that I've been wanting to buy, and I also want some new shoes, but the little shit doesn't have the money for any of that cause I've used up on his lingerie. So he's gonna have to earn me what I need, and if I find some more perverts who are into this sort of shit then we could even go on a whole shopping spree! I'll get him some new panties and stuff too, so you can help me pick the ones you think would look the cutest on him!"

Adrian was bawling his eyes out, but the sound was thankfully muffled by Claire's pussy as she smashed it against his face, bucking her hips and covering him in her juices, almost suffocating him as her pubes fully covered his nose. As for Amanda, she also was fucking him wildly, cursing and grunting and gasping in pleasure.

They both came almost at the same time, with Claire clenching her thighs around his head and squeezing so hard he no longer could even hear her moans, his ears fully covered by her soft flesh. Amanda, instead, fucked him in a frenzy until she arched up and came, her fingertips digging into his hips.

He could not breathe, could not focus on anything but the clammy hot skin enveloping him and the smell and taste that filled his head, making him feel vaguely nauseous.

Finally, after what felt like forever, Claire's legs relaxed and she let go of him, allowing him to breathe. His face was a sticky mess, his tears mixing in with her fluids as he looked away, face flushed red while his eyes were red and puffy from crying. The wig felt a lot looser, and as soon as he let his head droop it fell forward, covering his gaze.

Amanda pulled out of him too, her hand slipping down between his legs and pressing against the lump in his panties. His caged cock reacted eagerly to the warm and surprisingly gentle contact despite his shame, or maybe because of it, and even without her words he could tell that the fabric had become damp with his precum.

"He's gotten so wet", she said, stroking her hand up and down, and Adrian was almost grateful for the metal cage that prevented him from growing hard, even if his body still shivered and got even warmer.

"I think he was pretty close", Annie said, her own hand moving down to his chest and pulling up his bra, rubbing her thumb against one of his already-hard nipples before rolling it slowly inbetween that and her forefinger. "If you play with his tits too he usually manages to cum from his ass. Though I've only started with his cage training today so I'm not sure if it takes more with it".

"Let's see...". Amanda moved her other hand to his entrance again, easily slipping two fingers inside him. This time she purposefully curled them and pressed them against his inner walls in search of his prostate, while sliding them in and out.

Adrian clenched his teeth and tried hard not to make noise, but just when she found it Annie lightly pulled on his nipple at the same time, and he couldn't hold back a small cry.

"Aha, he felt it!". Amanda sounded very smug about it, moving her fingers more quickly and insisting on that spot, while the other hand kept massaging him from above the front of his panties.

Claire joined in too, taking off his bra together with Annie and playing with his other nipple, using the sharp tips of her acrylic fingers to scrape and pinch it harshly.

"P-please don't!", he whimpered, his body shaking with his sobs, but Annie pulled on his ear as a reminder to stay put before ripping off his wig, ripping out a few of his actual hair strands in the process. His own dark hair was damp with sweat which now easily rolled down his face and neck, and the rest of his body was drenched in it as well.

"You should be glad you're being played with by three beautiful girls", Claire said, before leaning down to lick and suck on his earlobe while pulling and twisting on his already-sore nipple.

"Maybe he doesn't like cock? You should test it out with your boyfriend and see", Amanda suggested, and Annie snickered.

"I could blindfold him again... that idiot still thinks I've let it put it in, but I just had a fleshlight between my legs and fake-moaned until he came. And now he feels guilty cause he thinks he came inside and I pretend to still be mad about it", she said, grasping on Adrian's hair when he tried to hide his face against the mattress. "Hey DON'T! You'll get lipstick all over my sheets! I'll really bust your ass if you try that again!".

Adrian clenched his fists and held on for as long as he could, hoping they would eventually get bored and leave, but the more he resisted the harder they tried until he had to stop his ass from shaking and moving back against Amanda's fingers.

"There, a bit harder... try pinching on the tip too, there! Ah, his legs are twitching! Keep going, you're almost there." Annie encouraged her friend, and as soon as those small fingers found his glans from above the panties and started squeezing and rubbing on it, Adrian knew he was done for.

He came with a hoarse cry, his ass clenching hard on Amanda's fingers and spasming as if it was trying to milk them, his nipples so hard and sensitive that they felt like they were burning as they sent electric sparks all through his body, spurting his cum inside the already-drenched panties that he was still wearing.

He almost collapsed on the spot, but the girls held him up and then rolled him on his back, giggling loudly at the sight of his current pitiful state.

"I've got to take a pic", he vaguely heard Annie say, and he didn't even have the force to protest or try to cover up as Claire forced him to face towards her friend with one hand and pinched on one of his nipples with the other, while Amanda made him spread his legs and pushed her fingers in again to stretch his hole and show off how loose her fucking had gotten him.

"His lipstick got all smeared up", Claire noted, pushing her thumb against his lips as Annie captured her first picture.

"He came so much that it spurted out of the fabric", Amanda said, then she grasped on the edge of his panties to pull them down by a few inches, making a small snickering sound as the sticky strands of cum connected the wet fabric to the tip of his penis. Annie of course did not waste time before taking another picture.

"I'll send them to our group later", she promised, while both Claire and Amanda moved up from the bed and started to get dressed.

"Can we play with him again?", Amanda asked, and much to Adrian's horror Annie smiled and answered "Of course! Any time!"

"Yay!". Amanda gave Adrian's panties a small tug, making them snap back against his crotch with a wet sound. "Bye Adrian! See you next time!"

"Yeah, bye!". Claire only briefly glanced at him, her lips curved up in a small smirk. "It wasn't half bad. I might try fucking him next".

"Sure! Make sure to bring a big one, I want to go up in size next week".

"Yeah, of course!".

"Bye Annie!"


Annie had left him alone for a few minutes to accompany her friends outside. When she came back, he was curled up in a fetal position and sobbing, covering up his face with his hands.

"What did I say? You better not have gotten lipstick everywhere!", she snapped, grasping on his hair to make sure to turn his face away from the mattress.

"W-why did you... why? I-I thought... I've done all that you said...", he whimpered inbetween sobs, his body shaking violently from the humiliation and fear. It was the first time she had let someone else than her touch him like that, and the thought that those girls would now know of their 'game' and even be let in on it filled him with anxiety.

"You got awfully cocky back then, didn't you?", she said, ignoring his words as her tone grew colder. "What did I say about talking back and being stubborn?".

"I-I'm sorry I... I can't... y-you can't let other people... you said no one would-".

He didn't even get to finish before she grasped her hand around his neck and squeezed, taking out her phone again.

"I said no one would know about how much of a disgusting pervert you are", she hissed, scrolling through her files until she found the one that she needed, pushing the play button and moving her hand to his hair to keep his head still when he tried to look away. "I can always send them this instead?"

"No! No! Please! P-please don't!", he whimpered, his green eyes filled with terror and darting between the scene on the screen and her face, his heart beating so fast it felt as if it would jump right out of his ribs.

"And then I'll send it to everyone else you know, and your life will be over", she continued, turning the phone away from him so that he could not see where she was tapping on the screen.

Adrian's ears were filled with static noise, his pride immediately forgotten as he grasped on the hem of her skirt and kneeled, looking up at her with tear-filled eyes.

"No no no PLEASE! I'M SORRY! Please I'll do better! PLEASE!", he yelled, bawling his eyes out like a kid while she looked down coldly.

"I'll let you off this once. But only because I really want those three hundred bucks, and I've already promised my friends they'd get to play with you more. So you better do your best to become a good little fuck-toy...", she said, putting her phone away while a wide, falsely sweet grin slowly spread across her face. "...and next time you'd better not forget, I've still got that video and the cum-soaked panties I caught you jerking off into".

Her hand went down to stroke his cheek, her tone deceiptfully gentle as she leaned down to whisper into his ear, her words making his blood run cold.

"I bet your parents don't want to know why your little sister's panties went missing, now, do they?"