Keith's Caught in a Costume Pt. 02

Keith steered his car into the parking lot of Northmark Mall and into a parking spot. Then, his hands returned, zombie-like, to the steering wheel, and he stared off into the distance. He couldn't believe what had happened. He'd got caught, rubbing his dick, dressed in a cheer-squad uniform, by the hottest teacher at his school. She'd humiliated him, made him jerk off, and eat his cum off the cheer bloomers. His hand shakily moved to open the center console and saw, again, the blue material of the bloomers balled up inside - evidence that this was all actually real. He snapped the console closed, unreasonably frightened that someone else might see the fabric and guess everything that had happened. Though, he supposed, there was someone that already knew. He unlocked his phone and looked at the latest text message:

Head to Kelly's in the mall. I've told a friend there all about you and she should get you set up with some nice panties of your own. If she doesn't let me know she's seen you inside an hour, that little video of you jerking goes live on the school's shared network.

Keith's stomach churned at the idea that someone else was already in on his humiliation. He checked the time on his phone and took a deep breath, wiping sweaty hands on his pants. Breathing out he opened the car door and headed inside.

It felt like every single person he passed was staring at him, and Keith kept his eyes locked on the ground in front of him until he stood outside Kelly's Closet - a women's clothing store where much of the fashion fell somewhere between Victoria's Secret and an obviously adult shop. Keith had spent a fair amount of time sitting on a nearby bench in the mall and inspecting every inch of the banners with hot models advertising the stores latest "Kink" campaign. The underwear pictured was meant to suggest leather wear and fetish gear while actually being comfortable. Seemed like stuff like this had become popular since books like Fifty Shades had come out.

Keith stepped inside and realized he didn't know what to do next. Ms. Blanchar had told him that someone would meet him inside and so he just sort of ambled about, trying to appear casual, stopping at some of the clothing racks, while running his eyes over the various stacks of panties laid about. Even at a moment like this he still imagined how sexy some of them might feel on him. Suddenly, he felt a tap on his shoulder.

"Hey, you're Keith right, from school?" Keith turned to find himself looking up slightly at Jenny, a girl in his class and member of the cheer team. "I think we had a class together last year, or the year before maybe?"

"L-last year," he inserted quickly, too quickly probably. He tried to maintain eye contact with Jenny but found his eyes inexorably dragged down towards her body. She was built like a sex machine. She was a little tall for a girl just turned 18, and had skin tanned a deep brown - maintained all year by a rigorous salon schedule. She had a beautiful round ass but her most distinguishing, and noticeable, features were on the front of her chest. Easily double-D, her breasts were a perfect rounded shape - gravity defying, as proved on the days she went braless, the pair were the subject of constant "boob job" rumours. Her brunette hair had blond highlights streaking through it and her face reminded many of a young Jamie Presley.

With all this, Jenny seemed like a straight alpha-mean-girl type, and had come on strong when transferring in in 10th grade. She'd aimed herself directly at Beth Thomers, the current it-girl of the grade, looking to take her leadership role on the cheer squad, and even making some passes at Beth's boyfriend early on in her time at the school. But something had happened after a few weeks and Jenny went from being bitchy and competing with Beth, to clearly recognizing her place and falling in as one of Beth's squad.

Tearing his eyes away from her body, Keith forced himself to look at her face, catching a smirking smile that said she knew exactly what he'd been doing. Still smiling, she asked, "So what are you looking for, something for a girlfriend?" She punched Keith gently in the arm, "Look at you, ladykiller! Come on, I'll help you find something."

Keith breathed a sigh of relief that Jenny wasn't the person he was meant to meet here, but then felt a sudden rush of panic as she grabbed him by the hand and started dragging him through the store. "Oh, no - I mean, I'm sure you're busy, I can find things myself."

"Oh, stop being silly Keith, this is what we do here at Kelly's! Now, let's see... what kind of underwear does your girl like," Jenny looked towards Keith for an answer, "Ok, haven't gotten that far yet, that's alright, we can work on that. Let's just get a sampling to see what you'd like to see on her." With that, Jenny began to drag Keith around the store and snatch up garments and underwear like a woman on a mission, tossing them into the stumbling teen's arms as he followed along behind her, afraid to make any more of a scene. Keith, for his part, kept looking around the store and looking to see if anyone was looking at him, trying to spot Ms. Blanchar's accomplice. That might be why he was so surprised to find himself suddenly led through a door into a back space of the store and then, with only a mild protest escaping his lips, into a large changing room.

"Here we are," said Jenny, "now we can see how all that will work!"

"But, uh, what do you mean," Keith stuttered out.

"You didn't really think I would let you just walk out of here without trying some of this on, did you," a sudden evil smile bloomed on Jenny's face, "Christy?"

Keith's heart sank, realizing he had just been played for a fool and now he was in the backroom with this teen sex goddess who knew at least some of the story. He reached new depths of despair when Jenny held out her phone, and the video of him jerking off was playing on it.

"Ms. B says you've been very naughty, using your sister's panties instead of just getting some of your very own. Well, here's your chance! And what a variety you've got to choose from! Now, Ms. B said I'm not allowed to tell anyone or show pictures to anyone, except her of course, if you're good. But, if you give me any trouble, I can show whoever the fuck I want. I really, really hope you give me some trouble."

Keith tried to breathe deeply and hold in the tears threatening to fall. He sniffled a little bit and said, "I'll be good, I promise. I'm happy to buy all of these you picked out and please don't tell anyone."

"Oh, Christy, but we don't know yet how any of these will look! And, before we had you try anything on, I've got to tell you, helping you pick everything out really wore me out. I mean, my feet are just killing me. Can you think of anything that might help?"

"Uhm, I guess I could rub them? Like, a massage or something?"

"Ooh, a massage sounds just perfect." Jenny quickly sat down on a chair located in one corner of the room and kicked off her heels, "Now, come get started Christy." As Christy moved over towards Jenny and seemed unsure of how to reach her feet while standing Jenny snapped, "Down on your knees dumb dumb." Keith fell to his knees and took up the girls dainty tanned foot and began to try to give a massage. "Ooh, a little harder Christy. Slower, no rushing through it." Jenny began to give off satisfied noises while Keith worked along for the next few minutes.

She then lifted her other foot and Keith moved his hands over. As she dropped the first foot she moved it to land right on top of Keith's crotch. Keith froze for a moment, until Jenny said sharply, "Christy, continue." Now, as he rubbed her foot she moved the other, just a little, rubbing right against his crotch. Keith felt himself began to harden instantly but Jenny continued as though she hadn't noticed.

A few minutes went by and Keith began nearly panting, this was the first time anyone else had ever touched him a sexual way, and he couldn't hold himself back fully from beginning to push back against the pressure. Jenny let him go for a few moments, pretending she hadn't noticed, and then suddenly yanked both her feet away from him and yelled, "Oh, gross Christy, were you trying to hump my foot?" She pointed towards his crotch, "Do you have a big boner in there for me, Christy? Come on, stand up and let me see."

Keith, knowing he had little choice if he wanted her to keep his secret, stood up and unzipped his pants. Ms. Blanchar hadn't returned his underwear after she'd caught him and so his little penis was immediately visible to the cheerleader who promptly broke out in laughter. "It's even smaller in real life! Oh, Christy, these panties are definitely the right thing for you! Ok, enough messing around, it's time for the fashion show." At this, Jenny tossed Keith a pair of panties. "You'll put each pair on and give me your best catwalk up the room and spin then come back."

Keith unfolded the first pair she'd tossed at him, neon green boy-shorts. He slipped his legs in them and pulled them up, only then noticing the lighter green lace surrounding the waist and leg holes. Whereas the regular material might not get called out as girly, the lace certainly would. He looked up at Jenny who, now recording with her phone, gestured with only a finger for him to proceed with his modeling.

Keith walked the ten feet to the other side of the room and then, spinning quickly, walked back towards Jenny. "Oh, yeah, those look great on you Christy, they're doing wonders for your package too," Jenny chuckled at the last - giving the lie to her words. "Next up, how about some cheekies!" She tossed him a pair of purple cheekies with pink polka-dots. As he slipped these up his legs into place he finally fully understood where the name came from, fully half his ass was hanging out the bottom of the tight underwear. When he duplicated his catwalk performance from earlier, Jenny laughed and said, "Ok, Christy, those actually do make your ass pop- you've been doing lunges." The sincerity of her words now compared starkly with the joking tone she had adopted earlier. Keith had now been praised for the girlishness of his ass and mocked for the tininess of his dick by this girl in just the last sixty seconds.

"Ok, these next ones are for working out," Jenny said, while tossing him the smallest bit of material yet. "These are athletic thongs, they're what all the cheer-girls wear so that they don't poke out the side of our bloomers of make lines on our leggings or shorts." Keith pulled the tiny bit of fabric up between his legs and tried to figure out what to do with his dick. Even his tiny package was struggling to fit. "Oh, Christy, push that tiny thing back between your legs." As Keith did he felt one ball, and then the other pop out of his sack and up into his body, he paused for a second, expecting some sort of pain, but then none came. So he then angled his dick back between his legs and readjusted the tight panties, finding they fit much better. "Oooh, yes," Jenny said as she clapped, "that's sooo much better."

Keith looked over at the mirror and almost did a real life double-take as he saw how feminine tucking himself away had made him look. His stomach and abs swooped down into the panties like he was born to wear them, and as he turned to see the backside he had to admit that if he were a girl, he would turn himself on. "Alright, enough admiring yourself," Jenny said. "Next pair."

This time, there was a lot more material, a lot more pink material, a lot more lacy pink material. The panties were full backed, dark pink satin, with rows of light pink lace ruffling off the butt. Keith left his balls popped inside his body as he slid the panties up his legs and almost immediately turned red as he looked at himself in the mirror. These were the most feminine thing he had ever tried on. They looked like the sort of panties sissies in videos online wore. The elastic was tight across the legs so it cut into his fleshy ass a bit and divided the hemispheres. As he looked at himself he felt a shifting between his legs and suddenly the front of the panties was poked out by his tiny erection.

"So, you must really like these," Jennifer noted, still perched on her chair. She stood up and began to walk towards Keith. "These panties make Christy's little dicklet pop right up, huh? So frilly and girly." As she passed behind him she ran his hand along Keith's ass, making the lace move below her hand. "Knees. Now, sissy!"

Keith dropped to his knees and saw Jenny playing with the edge of her skirt. He couldn't help it, his eyes kept traveling up her legs and trying to get glimpses of her panties. "Well, now Christy, do you want to see my panties?" Keith simply nodded. "What will you do to see them?"

"Anything," Keith responded.

"Will you kiss my ass?" Keith swallowed deeply and nodded quickly, definitely too eager. Jenny turned and inched the skirt up, finally exposing her ass wearing a pair of thong panties that matched the earlier athletic pair she had Keith try on. "Just think, Christy, when you're wearing yours I might be wearing mine. We might be twinsies! Now, give me a kiss on each cheek." Keith leaned in and gave a quick peck to each of her glorious tanned cheeks. "Now, Christy, tell me your a sissy bitch and you want to lick my ass."

Keith, almost hypnotized by the sight in front of him repeated, "I'm a sissy bitch and I want to lick your ass."

"Then go ahead, cover all of each cheek," Jenny smiled as she humiliated this boy. Keith leaned in and drew his tongue across her left ass cheek, moving quicker as he went and yet enjoying every moment as he covered her entire ass. "Now," Jenny reached behind herself and moved the thing out of the way, exposing her asshole to Keith's view, "ask my permission to lick my asshole."

Keith swallowed, the prospect of licking an ass breaking him out of his pleasure coma for a moment, and then realized that this was almost certainly part of being a good boy. "May I please lick your asshole, Jenny?"

"Let's make that Ms. Jenny."

"May, I please lick your asshole, Ms. Jenny?" Somehow asking the second time was way worse Keith felt.

"Well, Christy, I want you to reach inside those little pink, frilly panties and take that little nubbin you think of as a dick between your thumb and forefinger and start jerking it. Count the strokes. Once you get to 10, give my asshole a lick. Every 10 strokes you get another lick, and no more stroking until you've licked."

Keith dutifully began stroking, and found himself fully hard, his two and three quarters as fit to burst as he had ever felt it. After 10 strokes he leaned in and licked at Jenny's butthole. An acrid taste filled his mouth, but at the same time he felt a jolt of pleasure shoot through him. He stroked a little faster and, soon, found himself lapping away at Jenny's ass and quickly stroking.

Jenny enjoyed the feeling of power with this little-dicked nerd lapping away at her rosebud, but soon noticed he was feverishly pumping himself and sure to blow any minute. "Alright, stop!" she declared. Fixing her thong, she strolled over to her chair and stepped back into her shoes. Coming back toward Keith she stood over him, hand still in his panties with dicklet grasped between two fingers. She ran her hands over her breasts and reached down to the bottom of her shirt. "Do you want to see these little Christy, nod yes for me and give me 5 strokes, but don't cum."

Keith nodded carefully and tugged five times, trying desperately not to cum just yet. Jenny began to pull up her shirt, "Just the bra for now, but as soon as you see it I want you to jerk all the cum out as fast as you can!" She pulled the shirt up over her large breasts, even in the bra they bounced as they fell below the shirt. Keith saw her tits, lifted by a push up bra, and began stroking madly. Jenny shoved one of her heels forward towards him, "Cum on this, little Christy." Keith was lost in the sight of her bra covered tits and stroked wildly soon ejaculating right onto the heel.

As he panted in the aftermath of his orgasm, he began to think of the consequences and looked up at Jenny's only to find her recording the event on her phone. She gave him another of those familiar, evil smiles. "Now, Ms. Blanchar says you're not to leave any messes, so clean this up." Keith resigned himself to his fate and leaned down and began to lap around the front of the shoe picking up globs of cum with each pass of his tongue. It still tasted as salty as before, but somehow he didn't mind it as much. After several passes of his tongue over now clean-seeming shoes Jenny pushed him away with her foot. "Ugh, it's kind of gross how much you enjoyed that." She adjusted her shirt and skirt back down to fully cover herself. "Now, leave the pink panties on and get dressed. I'll get you checked out." She snagged his wallet out of his abandoned pants and walked out of the room.

Keith quickly got dressed, still full of disbelief that today was actually happening and quickly coming off his horniness into shame about what he had done and fear about what might happen next. Allison returned a few minutes later with a bag full of tags (all of which went to the panties he had) and a second larger pink bag in which she stuffed the various panties. "Now, these are yours, Ms. Blanchar doesn't think you should wear boys underwear anymore so from now on you wear these to school. Now, get the fuck out of here." With that, she shoved the bags at Keith.

Keith nearly ran out of the store, holding the two pink bags at his side, again afraid that everyone was looking at him. He hurried out to the parking lot and got in the driver's seat, throwing the bags in the passenger's seat. He sat there still for a moment and then felt his phone vibrate in his pocket, alerting him of an incoming text. Pulling it out, he saw it was from Ms. Blanchar:

Heard you had fun with Jenny. Bring all the clothes in the bag to school tomorrow. And a pair of athletic thongs. Wear whichever panties you want though! :)

Following the text there was a picture of Keith licking the cum off Jenny's heel. Ms. Blanchar and her cheerleader were obviously in close communication. Keith frowned, clothes? He looked in the bag Jenny had given him and after shifting the panties to the side he saw a few frightening items. It seemed to be two pairs of black leggings, ankle socks, pink and white cross-trainers, a pair of tank tops (one in sea-foam green, the other in a light pink) and two sports bras. When Keith picked the bras up he discovered they were padded as well.

Oh fuck, he thought, this can't be good. He dropped his head to the steering wheel and wished this wasn't happening to him.