The giggling began to pull Keith out of his head. Sitting in English class, halfway through the fall of his senior year of high school at St. Michael’s Catholic, Keith couldn’t find the energy or heart to care about Hester Prynne or her scarlet letter. So, he’d let himself drift off into fantasy. This fantasy, like many of his since the beginning of the year, was about his teacher, Ms. Blanchar.

Keith had first noticed Ms. Blanchar as a young eighth-grader, catching glimpses of her in all-school assemblies and in the halls between classes. When he’d gotten to the high school, he saw her more often, but it wasn’t until this year, when he saw her every day, that she’d taken on the principal role in most of his fantasies. She was in her mid-40’s, petite at what Keith guessed was about 5’2”, and was blessed by good genes and seemed to put hard work into her body. She had a tiny waist that didn’t flare out too much to her narrow hips and a tight, heart-shaped ass.

But her biggest assets sat high on her chest, two enormous double-D’s that even the most prudish of teacher’s clothes couldn’t have hidden. It was a double benefit then that Ms. Blanchar wasn’t the type to wear the prudish clothes of many teachers. She leaned into light skirts that rode the very edge of acceptable length and button-down shirts that were often undone just enough to show a fair bit of cleavage and just a hint of the lace of her bra. She’d wear tall heels and stockings, her short skirts sometimes giving a brief glimpse of garters.

Rather than trying to evade the attentions of the teenage boys she was surrounded by, she seemed to bask in it. She chatted up the hottest, most popular boys in each senior class and seemed to befriend the best-looking girls. She never crossed the line, at least not publicly. But there had been rumors since Keith had been in high school, and some, he’d heard, from even before that, that Ms. Blanchar had gotten extra-close with a student or two. He wasn’t sure if he really believed all the rumors, but they absolutely played a part in the fantasies he’d been having about her all year, and the one he was in the midst of even now.

As someone in the classroom droned on about their opinions on Hawthorne’s politics, Keith had let his mid-drift to just last week when Ms. Blanchar had called him up for his oral presentation. From there, things played out in his head very differently from reality and leaned heavily into tropes from the porn he watched online at home. Keith hadn’t actually had a lot of experience with girls, at 18, he was still a virgin and had to hope he was going to be a late bloomer in college.

So, it was out of this state that he was shaken by the giggle of the class. Shaking himself back to reality, he found his vision filled with a bulging red sweater directly ahead. Ms. Blanchar had come and stood directly in front of his desk and was staring down at him. He dragged his eyes away from her chest, and the red sweater that seemed stretched to its limit and met her eyes. She looked pissed.

“Well, Mr. Robins? Any thoughts on the themes we’ve been discussing?”

The irritation dripping from her words felt almost like a physical slap to Keith and he stammered out, “Th-They were obsessed with sex.”

Unfortunately, his nerves got to him and he practically shouted the last word of his answer. The class around him exploded in laughter and Ms. Blanchar’s glare turned into a death stare.

“Detention for failing to pay attention in class, Mr. Robins,” she bit off the last few words as she turned back to teaching the class.

Keith let out an internal groan, he’d had an extra off period at the end of today and had planned to leave early. Now, he’d not only have to stay until the end of the school day but serve detention after in Ms. Blanchar’s room. Ah well, he thought, at least I can look at her tits some more.

*****

The end of the school day came along faster than he had expected, especially as he spent the last bit of it, his free period, jerking off in the school bathroom. Well, trying to jerk off anyway. He’d thought it being during class would mean he’d have some privacy but he kept being interrupted by others, some actually using the bathroom, a few making phone calls, and one guy actually smoking some weed. The interruptions were so frequent that when the final bell rang, and he realized he had to hurry back to Ms. Blanchar’s room, all he’d succeeded in doing was making himself much hornier.

Detention started off normal enough, Ms. Blanchar gave him some grief and then told him to sit quietly and get some work done. She moved between the room and her office (one of two small closet-sized rooms off the classroom, the other being a storage closet) organizing and putting things away, and Keith mostly busied himself trying to watch her tits slightly bounce and her ass sway without her noticing. But then, she got a call and, after giving him a furtive look, stepped into her office and pulled the door mostly shut to take it. Keith couldn’t really hear the conversation, just bits and pieces, but it sounded like someone was trying to convince her to meet them. She argued a bit but finally gave in, she tried to sound irritated by her defeat but actually mostly sounded excited.

As she grabbed things from her office and walked back into the classroom, she looked at Keith and said, “I’ve got to run take care of a couple of things, you stay here and keep working until I get back.”

“But, detentions over in another twenty minutes, will you be back by then?” Keith tried to protest.

“I’ll be back when I’m back, and since you keep failing to pay attention a little extra time to do some reading won’t hurt you at all. If you’re not here when I return then you’ll be in detention the next three weeks, understand?”

Keith dropped his eyes to the floor and nodded, watching her feet stand there for a moment and then hearing a quick huff of irritation and seeing the feet stride off towards the door. He looked up to see the door closing behind her and leaving himself alone in the classroom. Without her to look at, he really wasn’t sure what to do. No matter what Ms. Blanchar thought he actually was a pretty diligent student, having read the material and currently caught up on his homework, he didn’t have much to do in detention.

He sat in the desk for a few minutes, took out his phone and fiddled on it for a bit. Then, tired of sitting, he got up and started roaming around the classroom. He looked in all of the public places first, checking out the books on the shelves and art hanging on the walls. Then, as Ms. Blanchar still hadn’t returned, he got a little snoopy. He looked in the drawers of her desk in the classroom and poked his head into her office and looked around a bit. However, he didn’t find anything beyond school supplies. Then he opened the storage closet and his breath caught in his throat.

The closet was almost entirely empty. These closets only really made sense in the art or science rooms as those teachers had actual stuff to store, but the whole school had been built on one model. Most teachers filled their closets with crap or with stuff related to any activities they sponsored. Here it seemed Ms. Blanchar was no different. She was the sponsor (or coach as she insisted on being called) of the cheerleading squad and so Keith found himself starting at a single cheerleader uniform hanging on a rack. It must have gone unclaimed, he thought to himself as he reached out to touch it.

Keith had a secret that almost no one else knew, sometimes he liked to dress up in girly clothes. The reason it was only ‘almost’ no one else was that he had gotten caught this past summer. His sister had been out of town on a trip and his mom was out for the night on a date. His father had left them years ago, Keith found himself alone in the house and decided to lean into one of his favorite activities, raiding his sister’s old costumes.

His sister, Lily, had been a dancer and gymnast since she was a kid only giving it up after graduating high school a couple of years earlier. However, she hadn’t yet gotten rid of her costumes, keeping them in a large chest in her bedroom. Keith has been sneaking in for years to try them on. Even as a senior he remained petite, his frame not filling out like most other boys had by this time. His ass always looked a little feminine, even more so in a dance costume for a teenage girl, and his penis, well, it wasn’t big enough to be an issue.

He’d pulled on one of his favorites, a pink leotard with a sort of sheer black skirt hanging down over it and also flowing down one arm, the black not really hiding anything beneath but instead emphasizing it. He had twirled around and was trying to get a good look at his butt when he heard a gasp at the door. He whipped his head around and saw his mother there. In moments she had him over her lap, still in the leotard and with the skirt now flipped up, and was spanking his ass hard. More than once, her hand, through some combination of her being blinded by anger, general inaccuracy or his wiggling on her lap, found his dick as she slapped down and the pain was doubled. It wasn’t until she had worn herself out that he was finally allowed to change out of the costume, under her watchful eye, and sent to his room. He’d spent the next few weeks grounded, but his mom hadn’t spoken of it again, nor, it seemed, had she told his sister.

So, it had been a while since he’d had the chance to dress up. And, he was still really horny from not being able to cum during his free period. Predictably, his desire won out over his good sense, with one last glance out the classroom door to make sure no one was coming, he stepped into the storage room and let the door shut behind him. He quickly stripped down and picked up the cheer uniform, it had the classic features in a blue and white pattern with Saints (the St. Michael’s mascot) across the chest and across the rear of the blue bloomers. Keith quickly slipped on the little blue garments (wishing he had some panties to wear underneath) and then followed it up with the skirt and top.

He pantomimed some cheers, even setting his phone up on a shelf to record him so he could watch later. He looked at himself in the mirror hanging on the wall, flipping up the skirt to see how his little bubble butt filled out the bloomers. As he preened, he began to rub the front of the tight blue shorts and drifted with thoughts of hot pseudo-lesbian action he might get if he were a cheerleader.

“What the fuck are you doing?”

The sudden screech startled Keith so much he fell to the ground.

*****

In another closet, fifteen minutes before…

“Oh, yes, fuck me, Jake, plow your teacher’s slutty pussy,” Allison Blanchar cried out in ecstasy as Jake Fuller, high school quarterback, prom king and alpha dog, thrust his cock into her pussy once again. Bent over the small bed in the closet, she looked back over her shoulder at him as he mounted her from behind.

“You like that, don’t you, you little slut?” Jake grinned at her as she rocked back into his groin over and over.

Allison moaned in response thinking that this closet was the gift that just kept on giving. She’d only worked at St. Michael’s for about 6 months when she discovered it, through a couple of lockable doors and remote enough that sounds didn’t escape. A few whispered words in one of her cheerleader’s ears and then she had ‘coincidentally’ discovered Bill, St. Michael’s janitor, and a young lady in the same closet, discovered them, as she explained to Bill, amid certainly unethical and possibly illegal activity. It took little time, possibly because Bill wasn’t very bright or because he was a weak little pervert, for Allison to have the only keys to the closet and the doors that led there, as well as one more key to a little cage around Bill’s junk.

That key didn’t get much use, Bill was too frightened to ask often and too dumb and ugly to be very interesting to Allison. The closet, on the other hand, had become the site of Allison’s own unethical activities. The school served as a well of freshly eighteen young bucks for her to break in. Jake was merely the latest senior to “assist” her in times of need, but he was certainly up to the task.

For Jake’s part, he was delighted at the opportunity to fuck the busty teacher, the object of most of the student body’s affections. It was the cherry on top that she seemed to melt in front of him, her frosty attitude fading as she became a slut for his large tool. Dating the head cheerleader, leading the football team to another state championship, inevitable homecoming and prom king, the truth was that living his own personal porn every day at school seemed to fit neatly into the perfection of his life. As he got close to cumming, he slapped Allison on the ass and simply said, “Knees.”

The teacher pulled herself off his nine-inch cock and knelt in front of him, the timing nearly perfect as he exploded all over her face and chest. She took a moment to revel in the slutty act, running her finger through some of the cum and looking Jake in the eye as she deposited it in her mouth.

“Delicious,” she purred. “You want to go again?”

“Nah,” Jake said, already grabbing his pants, “I got shit to do, and Beth wants to take in a movie later.”

He’d soon left, leaving Allison to clean up at the small sink in the room’s corner. She grinned as she cleaned the last of the stud’s juice from her face, repairing her makeup in the mirror hung on the wall. Her mouth slid from a smile to scowl as she remembered Keith Robins sitting in her classroom, still serving his detention. The little creep always stared at her during class, and his eyes had followed her the entire time in detention until she’d come to meet Jake. Sighing and giving herself one last check in the mirror, she made her way back to the classroom. Opening the door, she noticed that Keith wasn’t at his desk and the closet door was open. Moving quickly to the closet, she pulled the door open to find the little pervert leaned against the wall, rubbing himself, and wearing one of her cheerleader’s uniforms.

*****

“What the fuck are you doing?” she screamed.

Falling to the floor, Keith closed his eyes and prayed that this might all be a dream, that he hadn’t really just been caught in a cheerleader uniform by his wet dream teacher. His emotions moved from despair, to fear, to terror as he thought through the consequences. Allison, for her part, had a very different series of emotions running through her head, disgust at Keith’s actions, then amusement at the consequences he was sure to face. Sudden arousal as different possibilities entered her mind. She was used to being the submissive one in relationships, doing whatever it took to please an alpha male. But, there had always been something about locking up Bill the janitor that had turned her on, he was just too gross to delve further into that pleasure with. This feminine little boy might, however, be a different story.

Allison looked down at Keith, still seemingly frozen on the ground. He’d landed on his stomach and the skirt had flipped up onto his back exposing the bloomers and the peach-shaped butt she’d never noticed before just now. She briefly smiled before pasting a frown on her face and kicking at his ankle.

“Get up, right now, Mr. Robins.”

Keith climber to his feet and, slowly, turned to face his teacher. He kept his eyes fixed on the ground and could feel the burning in his cheeks.

“You’re supposed to be in detention, and here I find you playing with yourself in my closet, wearing one of my girl’s uniforms no less. Can you give me one good reason not to march you directly to the principal’s office?”

Keith stuttered out, “I’m so sorry.” He paused, hoping Ms. Blanchar might jump in and offer forgiveness. Hearing nothing, he continued, “I don’t know what to say, I’m so sorry. I shouldn’t have done it and I’m really sorry. Please, don’t tell the principal. I’ll wash the uniform, it won’t ever happen again, I’m just so sorry.”

“Quit saying you’re sorry,” snapped Allison, “You’re only sorry you got caught. If I hadn’t come in when I did, I bet I’d be finding a soiled uniform hanging on the rack whenever I got around to checking it.” Keith froze, not saying anything because that had been exactly his plan. Allison, recognizing his reaction, let her voice grow even colder, “Oh my God, I’m right. You were going to rub your little dick until you came in those bloomers and then just leave them for me or some other unsuspecting girl to deal with.”

Allison took a beat, trying to determine if Keith was ready to be pushed where she wanted him to go. “Have you done this before, jerked off in women’s clothes. Did you steal your mom’s underwear, or maybe something of your sisters?” Again, sensing confirmation in Keith’s flinching, “Aw, so you jerked it into your sister’s panties? Did you leave that for her too? Answer me, Keith. Or we are off to the principal and to call your mother.”

Keith, on the brink of tears, “Yes, I’ve used my sister’s panties and I just put them in the hamper after.”

“So, it’s your mother who has to deal with your disgusting messes, and now you thought I would take care of it. Well, no way that is happening. Take those bloomers off this instant.”

Keith reaches for the skirts side zip, “I didn’t say take off the skirt you dumb little sissy, just the bloomers,” Allison snapped. Keith jerked his hands away from the zipper, all too aware that she had just called him a sissy, a constant theme of the porn he watched at home.

He reached his hands up under the skirt and pulled down the bloomers, trying, as best he could, to keep his dick from showing. Even with the fear and humiliation, it was still hard, perhaps harder than ever, and Allison noticed.

“I see you are still getting off on some part of this you little pervert, pull that skirt up and let me see what you had stuffed in those cheer panties.” Keith hesitated for a moment and Allison quickly said, “Principal and then your mother. And now, I’ll have to let her know about you confessing to using your sister’s undergarments.”

Keith’s hands shakily grasped the front of his pleated skirt and pulled it up, revealing his full erection. Allison immediately laughed, she had planned to humiliate Keith anyway but this was beyond even her expectations.

“I guess you’re not a little pervert at all, you’re a tiny, minuscule pervert. How big is it, Keith? Don’t lie, little ones like you have always measured it.”

“Three inches,” seeing his teachers stare. Keith quickly said, “two and three quarters.”

“Well, I see why you’re so interested in panties. With a little clitty like that, they’re what you should be wearing anyway. We’ll deal with that later.” Allison picked the bloomers up off the floor, pinching them in between her fingers, and held them out to Keith. “Now, put these up to your nose and get a big whiff of your own juices and start jerking off.”

Keith blanched in response to these instructions and then jumped, startled, as Ms. Blanchard loudly clapped at him. “Do it now, sissy. Rub that little clitty in your hand and imagine these belong to one of my cheer girls as you sniff them. Maybe they’re Taylor’s, can you imagine her big round ass encased in them. Or maybe they’re Jenny’s, she’s got that dirty, hot thing that so many guys like. Or what about Beth, the girl next door, cheerleading captain, dating the football star.” Allison saw Keith had closed his eyes and was now pumping furiously. “Lick the bloomers, see if you can taste Beth on there. Maybe those were hers last year and she had to trade up a size. Who knows?”

Keith’s mind began supplying a stream of images, some memories, times he’d caught a glimpse up a cheerleader’s skirt, or the girls had worn particularly sexy outfits, but most from his lurid imagination. His head between Beth’s legs, or plowing Taylor from behind.

“Now, don’t stop jerking, I’m going to take the bloomers back,” Allison reached up and took them out of Keith’s hand while he took one last desperate lick and sniff, “And I’m going to put them right here,” as she held them under his dick so that with each stroke he lightly grazed the material. “Now, cum Keith, cum as hard as you can.”

Keith picked the pace up further, speeding towards the finish and opened his eyes to see his hot-as-fuck teacher holding the crotch of the panties right under the head of his penis. That sight alone put him over the edge, and he came right on those panties. It mas more than usual, a big load he thought to himself.

Allison chuckled. “Makes sense, that a tiny little dicklet would produce a tiny little load. But, I suppose that makes this next part easier for you.” Lifting the blue nylon cheer panties up to Keith’s face, she said, “Clean up your mess…NOW.”

Keith froze for a moment, looked up at his teacher, hoping for mercy. Seeing none, he squeezed his eyes shut and began to lick away at the panties. He reached for the fabric to have better control and get this over with and Allison handed them right over. He quickly realized that it wasn’t as bad as he’d expected and tried to hurry his efforts. As he began to lap at the runny liquid covering the gusset, he opened his eyes to see Allison holding out her phone and smiling, clearly taking pictures. He quickly licked up the last salty splashes of his orgasm and, once again looking down at the floor, and then held the bloomers out to Allison as though to return them.

“Oh, no, little Keithy,” Allison laughed. “You need to take those home and wash them. You clean up after yourself now Keith, and I guess you better hope you don’t get caught cleaning those up! Ugh, Keithy doesn’t work for you in this sort of get up, since you’ve dressed up before I’m sure you’ve thought of a name for yourself?”

Keith let his hands holding the bloomers drop back in front of him. The familiar shame that occurred after jerking off in his sister’s outfits was with him now, magnified by ten! He stammered, “Chris…Christy, ma’am.”

“Christy?” Allison laughed out loud again. “Perfect, for a little sissy boi like you! Well, Christy, you’re going to get a lot more time to show yourself than you’ve been getting. From now on, I want you to wear panties every day at school. And no more of this stealing your sister’s panties. Instead, I think it’s high time you bought your own, and I know just the place to send you!”

Keith blanched, sure now that his humiliation was only just beginning.

The End.

 

*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot has remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.