A Sissy Super Senior Pt. 03

(All characters are 18 or above!)

Chapter 5:

After making his way downstairs, Sebastian meekly stood in front of his mother, feeling shame over her seeing him dressed so feminine.

"My my!" She said in a tone that Sebastian was pretty sure was a mocking one. "Now I see why you've been so fascinated with dressing like a woman. Now that I see you dressed as one, you're quite the beautiful young lady!"

"Mom... Can I please change?" Sebastian asked. The intense arousal he felt when upstairs was completely depleted, now that he had eyes on him.

"Into another dress? You really love this don't you? Because I know after all the warnings I gave you, you're not stupid enough to still be


"Nevermind..." Sebastian said glumly. "Why is she so hellbent on this??" He thought to himself.

"Good! Well now that, that's settled. Sit down, I'm going to apply your make up! And you better be paying attention, because I expect you to eventually be confident enough to apply it yourself every day."

Sebastian knew better at this point to put up a fit. He just silently sat down, and let his mother paint his face with red lipstick, some blush, and a little mascara. After some time, she was done, and handed her son a mirror.

Sebastian was shocked. He... he looked beautiful! With his mouth open wide in disbelief, he looked in amazement as he saw a pretty 18 year old, dressed classy looking back at him. Sure his hair was short, but he nonetheless looked like a girl who just happened to have a pixie cut.

"Well.. how do you like it?" Mrs. Berns pondered.


"I-I look really nice?!" He admitted. "I can't believe I look like a girl!"

"Well, I'm sure this is a dream come true, missy but don't forget. This whole situation isn't just a free year of playing dress up to your heart's content. My hope, is that this setup isolates you from any social, personal, or other distractions in school. Not only do I expect you to give it 100% in your looks, I expect you to GET 100's in your homework and tests too. You heard Mrs. Kyle yesterday right? From Monday, to next year when you graduate, she expects you to be putting maximum effort."

"Yes mom... I'll work hard, I swear!" Sebastian responded. He was actually being truthful. The warning Mrs. Kyle gave him about how she expects full effort from him this year, even though he has to repeat senior year anyways scared him. What's worse than being a super senior? A super, super senior?

"Good, now finish up your homework, show me you actually did it, and then go straight to your room. No more laptop privileges either.

With that Sebastian finished the rest of the homework he started this morning. It was a pretty demoralizing to be doing it, knowing he'd have to retake all these classes next year anyways, but he stuck through and finished it- being the first time in a long time that he actually put an honest effort in his school work. As he worked, he remained completely conscious of the feeling of his tights wrapped around his legs and the frills of his sleeves however. As well as the softness of his panties. He had never been so horny while studying- but to be fair he hardly really studied anyways.

When he was done a few hours later, he showed his mother and after looking through each assignment she gave him her approval. "Good. See how easy it is to actually TRY? Now go back to your room. Hang up your new clothes,

Making his way upstairs, Sebastian couldn't help but enjoy the sway of his skirt as he walked. Walking into his room, he took notice of all his new clothes. So many skirts. So many dresses. So many bras and panties. "This must've cost a fortune!" He thought to himself. Little did he know much of today's outfits were paid for from a small portion of his college fund!

While Sebastian didn't like the idea of being forced by his own mom to play dress up, he did start realizing more and more to himself that he liked dressing up. The horniness from earlier was starting to swell up, now that he had privacy in his own room. Making his way to his mirror, he took a close look at himself, taking pride in the fact he passed. This made him hornier. So much so he jumped into his bed and began to jerk off- rubbing the panty's fabric against his dick. Cumming rather quickly, Sebastian began to pant heavily. But as he wiped, a wave of sadness came over him. The remembrance of having to repeat senior year. His secret crossdressing fetish being exposed to his mom, mrs. Kyle, and mrs. Lopez. Having to cut contact with his friends. And the embarrassment of being forced to live as a girl by his own mom... It all hit him like a brick, after being distracted by his horniness. Sitting in his room by himself, Sebastian truly felt lonely.

To distract himself, Sebastian washed his hands in his room's bathroom sink, and began hanging up his new clothes. As he picked up each item, he began to imagine how he'd look in each piece... and once again his dick starting stiffening.

To be continued...

Chapter 6:

Sebastian stayed in his room until it was time for supper, when his mom called him down. The two of them ate a light salad, which Mrs. Berns explained was to "help him keep a slim figure" to make it even easier to pass. Sebastian already thought of himself as a skinny guy, and all the crying he did the past few days made him hungry, so a simple Caesar salad was a rather disappointing. Still though, Sebastian knew better at this point to complain. If his mom was angry enough to force him to dress like a girl, she probably would kick him out.. She was always a relaxed mom, but I guess finding out your son failed senior year is enough to push a mom off the deep end.


After supper, Sebastian was sent back to his room, where he stayed the rest of the night- alternating between horny and devastated. A knock came on the door and his mother opened up, telling her son that she expected him to wear the proper sleepwear for a "girl his age." She also told him to take off his makeup for today.

Sebastian complied and opened up the drawer his folded the pajamas into. He pulled out a red 2 piece silk pajama set and went to the bathroom to put it on. After taking his makeup off with the wipes his mom provided, and changing, Sebastian became enamored with the silk pressed against his body. It felt so good, Sebastian almost moaned. Once again, the horniness was beating out the sadness.

When he walked out of the bathroom connected to his room, His mother wished him a goodnight, and told him to pick a new outfit for tomorrow from his new collection. With that, Sebastian went to bed and tossed and turned as he fought the urge to masturbate.

The next day, was more or less the same. Sebastian woke up, freshened up, then changed. This time he had the freedom of picking his own outfit. Wanting to dress less girly to lessen the embarrassment placed on him by his mother, he opted for a pair of jeans and a top. Still though, every jean he had either was embroidered on the back pockets and tight, or high waisted.. and also tight. And the tops were either blouses, or crop tops. He picked a pair of high waisted jeans, and a peach colored top. The sleeves were shorter than the shirts he was used to, but nonetheless he went downstairs and greeted his mother.

"Hmmm, I'm surprised you didn't pick a dress or a skirt, but those jeans do look cute on you." His mother teased.

Sebastian wasn't sure of whether or not to say thank you, because he knew he was mom was once again teasing him. He didn't have to make a decision though as him mom immediately resumed talking.


"Never mind that, if we want to make sure you pass as a girl next school year, we're going to be working very hard every day after school this semester and summer to get you fully immersed into the world of womanhood. Today, before you work on more schoolwork, you're going to be practicing your makeup- in fact you'll be doing makeup practice nearly every day after school." Said Mrs. Berns

"Every day?" He thought to himself. Slowly but surely, Sebastian was realizing his mother wouldn't move on from this plan of hers as he had hoped. So much of him hated this... but at the same time, he couldn't deny as much as he was trying that he's curious if he could learn makeup well.

After a quick breakfast, Sebastian's mother sat him down at the breakfast table and together they went over each makeup item she had given him the day before. His mother pulled up YouTube videos for each makeup item and how to apply it. Some things like the peach colored nail polish he put on his on his fingernails and toes were easy (They matched his top!), as was the cherry lipgloss Mrs. Berns told him to apply. So much so, that his mother starting asking if he practiced before.

"M-om, no!" He cried. He couldn't tell if she was teasing him or actually asking. After some challenge with applying light blush and mascara, Sebastian finally got the hang of it. By the time the afternoon had rolled around, Sebastian was done, and his mother have saved the link of each YouTube video.


"Perfect! Once your hair grows out more, you'll look like a girl. And last but not least, here I want you to start wearing this around the house, it'll be good practice for next year. " Under the table, Mrs. Berns pulled out a shopping bag which she handed to her now feminized son.

Upon opening it, Sebastian found himself staring at a pair of heels. "Should I put them on now?" He asked, nervously.

"Yes, dummy! I didn't get them for you to stare it." His mother teased. Sebastian complied, and put them on his feet. They were only 3 inches, so while a little uneasy to walk in compared to his sneakers, they weren't too bad.

For the rest of the day Sebastian was instructed by his mother to read ahead of the next unit in his math textbook, and after every hour of reading to do 5 laps around the house. By the time 10pm rolled around he had fully read the whole unit in his text book (mainly because his mother was keeping an eye on him) and walked more laps than he could remember. His feet were aching but at least he was used to walking in heels.

"Well you certainly worked hard today, missy. If only you worked this hard throughout your high school career we wouldn't be in this mess! Now go upstairs, wipe your makeup off, and don't leave your room for the rest of the night." Mrs. Berns warned.

"Yes mom.." Sebastian said tiredly. Walking upstairs was a little harder in heels than his laps were. When Sebastian got upstairs, he was about to kick his heels off, but when he saw himself in the mirror, with his makeup and heels on, he started feeling all tingly over how much of a girl he actually looked like. The tightness of the bra and how it poked out of his blouse made his figure look feminine, as did the snugness of his jeans. After a weekend of stress, anxiety, and humiliation, the alone time he got where he actually got to appreciate this situation in private was a small bonus. Looking closely in the mirror, Sebastian started to get horny. And without thinking, he rushed to bed, jumped under the sheets, and began to masturbate. 

A few minutes passed, and eventually Sebastian came into his nail-painted hands, and fell asleep.

To be continued....

Chapter 7:

Sebastian's alarm rang at 6:30 am the following morning. Given it was a school day, Sebastian's heart ached. It felt pointless to get ready for school, knowing he'd have to repeat it all again next year. But after the meeting with Mrs. Kyle and Mrs. Lopez, and of course the sternness of his mother this weekend, he knew he'd have to put in maximum effort every day in school from now on.

Looking in his closet, Sebastian changed out of his girl clothes he fell asleep in, and headed into the shower. After washing up, he got out, and changed into his regular, boy clothes, and waited for the bus. Because of how early school starts, his mom was still asleep. When the bus finally came, Sebastian started to feel sadness, knowing he'd have to cut ties with his friends. In part because of his mother's orders as punishment, and also because he was too humiliated to tell them he was being held back a year.

When the school bus came, Sebastian braced himself to adjust to having no social life, but as he grabbed the rail of the buss's stairs, he realized... He never took off the peach colored nail polish!

"CRAP! CRAP! CRAP!" He thought to himself as he got onto the bus. "Play it cool, just play. It. Cool. Lots of guys wear nail polish these days. He thought to himself. But nonetheless, when he sat on the bus, he got a few puzzled looks which he knew were because of his nails.

"Hey Seb! Nice nails!!" Sarah said, who was already picked up.

"Uh.. thanks Sarah! I uh... I was just trying a new style." Said Sebastian, trying to 'play it cool.'

"Well it looks great! I think it's totally cool when guys paint their nails. Griffin [Sarah's boyfriend] is too scared to do that type of thing, but I like when guys are comfortable in their masculinity to do things like paint their nails!"

Ironic. Still though, it hurt Sebastian a little inside to be complimented so much by Sarah, knowing all too well their time together was limited and eventually he'd have to cut her off. Eventually, more and more of his friends got picked up as they got closer to the school. As most of them were guys he got some minor teasing for his painted nails, but it was all in jest. Sebastian tried his best to pretend nothing was wrong, while still being less talkative than usual.

Once in school, Sebastian went to each class, and out of fear of his mom's wrath, he tried his absolute best to pay attention in each, and actually take notes. Outside of his friends, nobody commented on his nails, but he could tell some people were sneaking quick looks at them.


Eventually math class rolled around, and Sebastian began to panic, as he was afraid to see Mrs. Lopez after the humiliation of last Friday. When he walked in, he went straight to his desk, and he could feel Mrs. Lopez glaring at him.

He tried his best to avoid eye contact, but once everyone walked in, Mrs. Lopez announced she'd be passing out worksheets she wants to start the lesson off with. "And I expect ALL of you to do them with diligence. No using your school laptops either!" she warned. Sebastian knew this was aimed at him, and he started to get red in the face.

When Mrs. Lopez came to Sebastian's desk to give him the worksheet, she paused for a second, taking notice of Sebastian's nail.

"Oh!" She said, as if she was pleasantly surprised. "I like your nails Sebastian! Did you paint them yourself?"

"yes." He said quietly.

"Well good for you! I think it looks very pretty!"

Sebastian was beet red. "Mrs. Lopez DEFINITELY thinks I'm a total sissy." He thought.

As he worked on the worksheet, Sebastian actually knew most of the answers because of how much he studied over the weekend. It made him a little happy at first, but it also stung knowing that if he studied sooner, he wouldn't have to be held back. Nonetheless, the rest of math class, and the rest of the school day went without a hitch- even in gym class, nobody paid too much attention to his painted nails outside of a few confused glares which Sebastian had grown numb to; Sebastian was always seen as a kind young man, so nobody ever thought to give him a hard time throughout his school career.

Chapter 8:

After a bus ride back home, where he had to continue faking being happy around his friends, Sebastian opened up the front door of his house. For a second, he completely forgot about the 'girls clothes only' rule his mother had enforced for as soon as he came home. He wasn't reminded of it until he saw a note attached to the other side of the front door:

"Don't forget to change!

Makeup too.

Heels too.

Homework after.

-Mom."

Once again, this was another reminder to Sebastian about how unwavering his mom would be in enforcing him living as a girl until graduation. Still, the embarrassment of it all was still present.


In his room, Sebastian looked at the girl's clothes to determine what to wear. Saturday he wore a skirt, whereas Sunday he figured it was less embarrassing if he were jeans. Still though, he enjoyed the sway of how the skirt felt on Saturday... "She's going to make me wear all these outfits eventually" He rationalized to himself, as he picked out a black t shirt, with a white frilly skirt, which was an inch higher than his knees. In truth though, Sebastian just wanted to see how pretty he could look in the skirt.

After putting on a pair of fresh panties and bra, he put the shirt and skirt on. The shirt was admittedly a little plain, but Sebastian didn't want to look like he was overdoing it and give his mom the 'wrong' idea, and make her think he's enjoying this. But as he admired the way the clothes fit on him, and he began to grow horny once more, and once again beat himself off. 

After washing his hands, he played a YouTube video from a beauty YouTuber he was now subscribed to, and followed her makeup tutorial. A little blush, and some lip gloss. While a simple look, it did wonders on making him look feminine, and it made him happy with the way he looked- something that he was embarrassed to feel.

Sebastian then found his heels, put them on, and went downstairs to do his homework. He was tempted to use ChatGPT or something to have It all done for him, but he knew better now than to act on those urges. Still though, it was a drag to do it. 

Eventually Mrs. Berns came home, and she was happy to see her son actually be working, and to have seen he had followed the instructions on her note.


"Keeping him dolled up like this, even if he secretly likes it, is really working so far." She thought to herself. "Either this gives my child some clarity on their gender identity, or it embarrasses them to the point of obedience, or... a bit of both. Either way, this is the way it's going to be."

The rest of the night went relatively normal. Sebastian sat at the kitchen table, did school work, then read through the units in his textbooks, as his mother alternated between watching him, scrolling through her phone, and watching tv. Sebastian's mom simply assumed her son redid his nails, not realizing he accidentally left them painted. She also took note of the fact he put a skirt on, on his own.


After dinner, Sebastian was free to go upstairs for the rest of the night, but was reminded to not text any of his friends. While upstairs, Sebastian was glad to finally be out of the watchful eye of his mother. He did a few girly poses in front of the mirror, which made him horny again. He knew he should find posing to be too cringy, but he couldn't help it. Once again, he jacked off, but after finishing, he made sure to wipe the makeup off, remove the paint from his nails, and change into his 2 piece, silk pajamas.

Little did he know though, his mother was downstairs, forming many, many more plans for her girly son...

To be continued...