[TG] Deportment 101 (Commission) (Patreon)

Commissioned by ToasterDude1 on DeviantArt

After being late to select his elective classes at college, Dustin ends up in in the mysterious Deportment 101 and slowly begins to change.

~

Dustin looked down at his timetable with disgust. Never again, he vowed, would he go drinking the night before class sign ups. By the time he’d dragged his hungover ass down to the reception to hand in his class enrollments for the semester all the good electives were full. He had been looking forward to a fun, easy class to distract him from his business major but with only one option to choose from he’d had no choice but to enrol in Deportment 101.

Fucking Deportment, what was this, the bloody Victorian era? Who the hell attended an ivy league school just to learn manners and which fork to use on salads? Yet here he was, standing outside the door to the smallest, most forgotten classroom on campus about to spend an hour learning to fold table napkins or something, he had no idea, nobody would. Why he couldn’t have just left the space in his timetable blank and had extra study time he had no idea but the college was insistent that in order to stay enrolled as a full time student, his roster had to be full.

“May as well get this over with.” He sighed, pushing open the door to find a tidy classroom with half a dozen other men sitting around looking bored.

That surprised him, he assumed anybody willingly taking a class on manners would be women, they all turned to look at him with dull expressions before one, a jockish looking blonde man smirked.

“Late to sign up? Or mandated enrolment?”

Ah, that explained it.

“Late.” Dustin answered, flopping down into a chair, “You?”

“Mandated enrolment, they force guys who ‘cause trouble’ in other classes to take this one as a sort of punishment. I think you’re the only one here not forced into this by the admin. Name’s Brad by the way.”

“Dustin.”

Great. Not only was he stuck in a useless, boring class; it was the one specifically designed as a punishment. Fan-fucking-tastic, this semester was off to a great start.

“Have any of you met the lecturer?” Dustin asked, “My time table just says T.Aster.”

One of the other guys behind them laughed, leaning back in his seat with an easy grin.

“Miss Tiffany Aster.” He wiggled his eyebrows, “Easily the professor that’s easier on the eyes, saw her at a faculty meeting the other week, trust me boys, even if the words she’s saying ain’t interesting there will be quite the view in this classroom.”

As if summoned by the mention of her name the sound of heels clacking on the linoleum floor echoed through the door. Now that her beauty had been built up a hush fell over the small gathering as all eyes flew to the door just in time for a long leg to step through it. Somebody wolf whistled and Dustin couldn’t blame them; that guy had not been kidding about Miss Aster being easy on the eyes.

She had a figure that made the sensible pencil skirt and blouse she was wearing look downright indecent; with long black hair that shined to match her equally dark eyes. With her pale skin, black hair and monochrome outfit she almost looked like an old black and white photograph, or at least she would, were it not for the splash of red that was her lipstick. She smiled sweetly at them both, sharp white teeth actually glinting in the morning sun. Her eyes narrowed at the whistle and she sat her books down upon the desk with a heavy thunk.

“There shall be none of that behaviour in my classroom.” She said curtly, “Lest you want a severe punishment.”

“I wouldn’t mind being punished by her,” Brad whispered to Dustin, elbowing him a few times.

The sound of sharp nails scraping across paper drew their eyes back to their new teacher, she tapped a name on a typed list and looked up at them.

“Brad, is it?” She smiled, sharp teeth reminding Dustin of a shark, “Thank you for volunteering to go first. Up at the front please. All of you, in a straight line behind Brad here.”

They all unenthusiastically shuffled to the front where Miss Aster stood before turning her back to them.

“Poise, how you carry yourself is the very first step to proper deportment.” She began, “Follow me.”

Dustin had to hold back a snicker, maybe this class wouldn’t be so bad after all, if their work consisted of learning how to walk this was going to be the easier A he ever got. However, they had only taken a handful of steps before she made them stop.

“No, no. A lady has a gentle sway to her steps. Keep your backs straight and remember to point your toes as you move your legs forward.”

“Uh, what?” Dustin gaped, “You want us to walk like women?”

“Like ladies, yes.” Miss Aster responded, “This class was designed for women, it’s not my fault you happen to be men. If you want to pass and avoid doing this all again next semester I suggest you give it a try.”

A few of the guys complained, Brad flat out refused and Dustin felt small and in the middle. He definitely didn't want to make a fool of himself, but at the same time, the idea of failing the class and having to take it again next year sounded like a nightmare.

“Let’s just get it over with?” He suggested quietly, “No laughing and nobody mentions this outside these four walls, deal?”

Brad and the others grumbled but agreed so, with a face red as a beet, Dustin pointed his toes and took a step. It felt wrong at first, feeling his hips sway with each step, making his ass stick out ever so slightly but after three laps of the room the movement was becoming second nature.

“Excellent ladies, now take a seat. Feet together, back straight then, once you are seated cross your ankles like so,” She demonstrated, “And clasp your hands together in your lap.”

Dustin had never been so humiliated in his life, judging by all the red faces in the room he wasn't the only one. No wonder the college used this class as a punishment. He would never admit it but sitting like this was actually quite comfortable; it almost felt as though his ass had more padding than normal. He shifted slightly, feeling his round cheeks squash against the seat in a way they  never had before; did posture really change that much about how your body felt?

“Dustin, do not fidget, it’s unladylike.”

“I’m not a lady.” He whispered under his breath, if Miss Aster heard, she didn’t react.

Thankfully, that was all for their first class and they practically fell out the door in their haste to escape; at least they could take solace in knowing none of them would tell people what was actually happening in that classroom, lest they all lose what reputation they had. It was only later, as he was walking towards his dorm that Dustin even realised his hips were swaying all on their own.

~

Deportment 101 was slowly becoming the most memorable part of Dustin’s education for all the strangest reasons. For the first few weeks he dreaded that hour a day he spent learning how to walk and hold himself like a woman but the longer it went on the more natural it became. He, Brad and the other men stopped complaining and tolerated it, but then it almost became normal and sometimes, though they would never admit it. Fun. Dustin couldn't help but giggle girlishly the first time they had to learn to curtsy; Brad just looked so funny bending his knees that way. Though he had to admit, the man did have oddly smooth and long legs. In a weird way he was sort of…jealous.

“You know, you could shave.” Miss Aster suggested, appearing behind his shoulder and he blushed.

Was his envy that obvious?

“Swimmers do it all the time, there is no stigma about it these days.” She cooed, “Here, I’ll teach you.”

She had him angle his leg up on the table and grabbed a pink razor from her bag, showing him how to angle it before handing over some cream to ensure the skin didn’t get dry. Some of the other guys gathered round to watch, some even asking for a razor of their own. It was an oddly freeing sensation, watching all that manly hair slide off, revealing smooth skin and long, pretty legs to rival Brad’s.

“You know, it’s a shame to hide those pretty legs under jeans.” Miss Aster sighed, “This seems like the perfect time to start our new unit on presentation.”

“Oh Gods, not public speaking.” Brad groaned but the teacher just laughed.

“No, not giving a presentation but how to present yourself!” She corrected, “Come all of you, stand up straight and let me look at you.”

Dustin and the others obeyed, standing as they had been taught with one hand on his hip, one leg slightly extended, butt sticking out to the side. It did not even feel strange anymore. Miss Aster looked him up and down and nodded, opening the large desk drawers and taking out a plastic shrink wrapped pack of fabric and handing it to him. He ripped it open as she distributed them further, surprised to find a jean skirt and pink tank top, complete with a black choker accessory patterned with roses.

“Oh.” He looked around at the others who all had similar outfits. “Miss, don’t you think we could change the curriculum just a little bit here?”

“No, I don't think so.” She tutted, “You boys should get in touch with your feminine side, it’s healthy. Now, strip off and change. I want you all wearing these to each class, consider them your uniform.”

Dustin made a face, walking and talking like a woman was one thing but dressing as one? Still, the looming threat of another semester of deportment classes loomed and he, Brad and the others all swallowed their pride. It felt oddly satisfying, sliding that jean skirt up his now smooth legs, he shouldn't help but blush when it settled over his hips.

“Um, Miss, Aster, I think I need a bigger skirt my uh…my ass..”

It was barely covered by the material, one wrong move and he’d be flashing the whole world. Not to mention his boxers stuck out the bottom in a very unappealing way. Miss Aster seemed far more concerned with the later than the former.

“We’ll just have to get you a pair of bikini panties, don't worry dear.”

Oh, okay. If he had to wear women's clothes he supposed having the underwear to match did sort of make sense, his boxers did feel strange under this skirt. Trying to put it out of his mind he pulled the tank top over his head; expecting it to stretch across his broad shoulders and chest and look awful but to his surprise it fit perfectly. Perhaps it was the strange angle, looking down at himself but he swore his torso was slimmer in the middle; with this tight shirt on it almost had an hourglass look. Weird. Obviously he had no chest to fill out the front but other than that, it looked surprisingly good, especially with the choker around his neck, even if it did crush his adam’s apple a little. Brad grabbed his shoulder, grinning ear to ear.

“Wow you look amazing!” Dustin gasped.

He really did, had you asked him a few weeks ago if that brutish jock body would fit in a red mini dress, he’d have laughed you out of the room but somehow, Brad’s figure worked wonders with it, his pecs even gave the illusion of small breasts. Dustin, despite the strangeness of the situation, felt a strange stab of jealousy at that.

“Hell yeah, hot no matter what I wear.” The man winked, the others were all having a similar reaction, perhaps they had all just grown used to acting and thinking differently in this classroom.

“Looking hot to trot, ladies” Miss Aster beamed, nobody corrected her, “Now, let’s put everything we’ve learned so far together. One, two, three, strut!”

It was second nature now and it felt even better than usual while wearing this outfit. Dustin could feel his round ass bouncing underneath the skirt, it felt oddly satisfying. Ruined only by the scrape of his boxers underneath ruining the illusion. With an irritation sigh he stepped aside, wiggling them off to go commando; a little embarrassing but he wanted to get the full experience until he could go to the mall after class and get himself some panties. The idea bought a blissful smile to his face, maybe he’d even get a bra to fill out this tank top.

~

The rest of Dustin’s business major seemed to float into the background of his life; when he wasn't in Miss Aster’s class he was thinking about it. He and the other men from the group were becoming fast friends; their secret class activities binding them together in their own special group. They took special joy in subtly mentioning their ‘special’ assignments in front of other people, giggling behind their hands when they asked about it only to be met with coy deflections.

They had even started wearing their outfits outside of the class and around campus. At first they garnered stares but Miss Aster told them to ignore it.

“They are just jealous of you.” She assured them, “You are fabulous while they are plain.”

It was true. Now that he’d started following the diet prescribed by the teacher Dustin felt more confident than ever in skirts. With his log, beautiful legs and round, peach shaped ass, how could he not? His chest was even starting to fill out similar to Brad’s and he eagerly awaited the day he could stop stuffing his bra to fill out his shirts. He looked forward to each new unit with absolute glee; dancing, flirting, make up; it was all so fun. Miss Aster had been right, getting in touch with his feminine side really was enjoyable, there was nothing to be ashamed of. So when she announced it was time they learned to apply make up she was met with cheers rather than the groans of early weeks.

Dustin felt so sophisticated as he pressed the tube to his full lips and carefully painted the pink pigment across them. Pressing them together a few times to make sure it spread properly just as Miss Aster demonstrated.

“Lovely.” She praised, “A natural. Now take this lipliner and paint it across the bottom and top parts to draw attention to your cupid’s bow, that’s it.”

His lips had never looked so full and sensual; the girly colour matching perfectly with his outfit. Brad looked like absolute fire with his liberty red lipstick to match his dress; if Dustin was girlish, Brad was sexy. He pouted and Miss Aster laid a hand on his shoulder.

“We play to our strengths darling.” She assured him, “There are many kinds of sexy, Brad’s is just more…overt than yours.”

“Heh, yeah, I can’t help that I am hot as hell. Don’t worry Dustin, I’m sure if you try hard one day you’ll look at least decent next to me.”

One of the guys imitated a cat hissing.

“At least my outfit doesn’t make me look like a whore.” He cut back, “Thre is sexy and then theirs desperate.”

Unlike in most classes Miss Aster did not intervene, in fact, she took a step back and motioned for them to continue.

“You’re just jealous.” Brad huffed, “Because you’re flat as a board. You wouldn’t know sex appeal if it slapped you in the face.”

“If anybody is getting slapped it’s you, bitch.”

Brad gasped, hand to his heart in shock and instantly, Dustin realised he had crossed a line.

“Now ladies, we do not throw around the B word casually.” Miss Aster said finally, “That argument was catty girls, but not quite pointed, if you want to learn how to be properly bitchy, we can speed up our curriculum.”

They all looked at her with surprise.

“A man uses brawn to find, women use their words. Dustin and Brad here have shown a real talent for it but all of you have to hone those skills if you are going to pass my class. Now finish applying your mascara and we will get started. None of you mind if we go long today?”

Nobody said anything, extra Deportment classes were a real treat, they all eagerly went back to painting their faces so they could get a sneak peak of the next unit. Dustin could feel Brad’s eyes on him as they worked and he smirked. If there was one thing he beat the blonde in, it was eyes. Where his were a dull greyish brown, Dustin’s were a vivid blue that really drew the eye. As he carefully applied his cat eye to the side he smiled; he’d show that idiot what real beauty was.

~

“Get dressed in a hurry today, Dustin?” Brad cooed, swirling a long blonde hair around his finger.

Dustin looked down at himself, he was wearing the outfit Miss Aster had assigned just as he did every class; his brow furrowed as to what Brad could be referred to. Then he realised, rushing to one of the many mirrors that had lined the room with just last week. His make up, he’d been so tired after his night of studying he’d applied his plum coloured lipstick instead of blush pink.

“Don’t be mean, some of us have to rush in the morning.” One of Brad’s cronies cut in cruelly, “I’m sure it was a mistake, nobody would ever wear pink with plum. It’s like, basic.”

Dustin flushed; how embarrassing. Ever since they started their unit on cliques and how to find your place in them, Brad had reigned supreme in their class. He was the queen bee and everybody knew it; up until today Dustin had been confidently in the middle of the pack but all it took was one small blunder for the claws to come out. His eyes burned with humiliation but he refused to let them get the better of him; he tried to remember what Miss Aster had been teaching them about attitude and confidence. Swallowing down his fear he put on a confident, almost bored look; flipping his hair over his shoulder and turning to face the group.

“Some of us,” He said, “Like to experiment. Then again, we can't all be trend setters.”

He stuttered over to his desk, passing Brad on the way and placing a gentle hand on his shoulder.

“Some of us are just natural followers after all, there is nothing wrong with that.” He pouted, “I can’t help but be ahead of the curve.”

He kept walking, making sure to keep the mental picture of Brad’s red and furious face in his mind for later. The sound of gentle clapping filled the air and he turned to see Miss Aster having just arrived.

“Wonderfully done, Dustin. Real bitch boss vibes.”

Dustin preened before putting on a face of dignified modesty and hoped for further praise; which came in the form of their newest assignment.

“I think we all know you have come a long way in this class, I think it’s time your names reflected that.” Miss Aster smiled, “Dustin, Brad, George…they are all so plain.”

Dustin pouted, she was right, it was such an ugly, manly name. He was beautiful and girly, he really should have changed to something more fitting.

“Let’s make this a group activity, we’ll all workshop new names together.” Miss Aster announced, picking a name at random for them to work with.

Slowly, each man in the class was rechristened; Juniper, Hailey, Krystal, Tammy. When it was Brad’s turn he took the name Bianca.

“It means pure.” Dustin spoke up, “I think we all know you’re far from pure, honey.”

“I’m pure sex.” Bianca held up her nose, “Pure, distilled sex on legs. I think it’s perfect.”

Dustin bit his cheek, he had no come back. Dammit! He could see Miss Aster making a note in her grade book; that was going to cost him his A in Wit, he just knew it! Damn Bianca and her confidence.

“Now Dustin,” She mused and Brad snickered.

“Dusty maybe, that would suit her.”

“How about Daisy?” Another piped up, “She hella girly and cute, that’s a good cute name.”

Dustin screwed up her nose; Daisy was such a little girl name; she needed a woman’s name to go with her womanly figure.

“Daphne?” Miss Aster suggested, “Sophisticated, feminine and a little exotic sounding without being too odd.”

“That’s perfect.” Daphne breathed, the name settling over her like a blanket. It felt right.

As they continued Daphne let her mind wander, casually doodling her new name all over her notebook in looping letters. It just rolled off the tongue, how had she even gone by Dustin for so long it almost felt wrong.

~

The classroom was filled with harsh whispers, all the girls gathered in tiny circles as they waited for Miss Aster to arrive. It was their final class and despite the sadness they all felt there was excitement in the air. As they neared Christmas Miss Aster had decided to give them one final assignment to come in dressed for the season. Hailey had come dressed as a sexy santa, Juniper a reindeer decked out in far too many leather reins and Bianca had basically just wrapped tinsel around herself to the point of indecency.

Daphne felt a smug smile form on her face when she saw it; as usual Bianca had gone too far and just looked like a slut while she, on the other hand, was sure to score an A. She had dressed herself in knee high black boots with white fur and a red dress, decked out with a black leather belt. Holly braided into her long brown hair and a shiny golden bell hung around her neck just high enough to be considered modest while also drawing the eye to her now bountiful cleavage. Bianca scowled when she saw it but said nothing; she knew she was beaten.

When Miss Aster finally arrived, gift baskets in tow her face split into a wide smile

“Oh ladies, you look wonderful.” She praised, “Come now, one at a time, up to the front to model.”

Daphne raced to be first, strutting down the row of desks with a wide smile, enjoying the sway of her hips and bounce of her breasts as she moved. No bra today, she liked the extra jiggle that came with going free; plus the thick fabric of her dress hid how diamond hard her nipples were getting from all the attention. It was even making her a little wet; she may be just as much an attention whore as Bianca but at least she did a good job of hiding it.

Daphne spun on her toes, letting the skirt flare out so that her classmates got just the briefest, ‘accidental’ glimpse of her bright red panties stretching across her pretty ass. Doing her best to make the blush look like one of realisation and embarrassment rather than pleasure.

“Wonderful, simply wonderful, Daphne. An A if ever I saw one then again, you really are my star pupil.”

“She’s got an A cup that’s for sure.” Bianca whispered loud enough for the whole room to hear.

Miss Aster gave Daphne an expectant look as if to say ‘well? Are you going to let that slide?’.

“What was that sorry, Bianca?” He called, “I couldn’t hear you talking out your ass, oh wait, no that can’t be it because you don’t have one.”

Some of the girls oohed, the others laughed as Bianca turned bright red, sinking down into her seat to hide her flat butt. Her one flaw no amount of fancy trappings could hide.

“Well executed.” Miss Aster praised, handing over a small certificate.

Daphne beamed looking down at it; she’d achieved an A in Deportment 101.

“This, of course, means you will be joining us next year for Deportment 102.” Miss Aster smiled and Daphne beamed right back.

She couldn’t wait.