Anna was a shy high school senior soon to graduate. She didn’t have many friends, and was very socially awkward and definitely never kissed a boy before. In fact, the only boy who ever gave her attention was Arnold who kept trying to talk to her about superhero movies. She didn’t care much for them but was too shy to tell him to stop and so would just passively listen and nod as he went on and on.
She often got mistaken for being a middle school boy if she had a hat on because of the way she dresses. She never had siblings, her parents were often busy with work and she always prefered introverted hobbies and so was never around other girls to learn how to dress like one. But after her secret crush Brian asked out a different girl and they started dating she had enough. She went to the mall alone and bought some skirts, dresses, and makeup with her allowance. She looked up makeup videos online to figure out how to do it.
This was her first day dressed up. She wore a short jean skirt, a pink blouse, and put eyeshadow and mascara on her eyes. Her parents gave her a look of “something seems different but can’t tell what”, before running off to work in the morning.
During her walk to her first period class and during the class she noticed people finally looking at her sometimes. It felt amazing, like she was finally wanted. She was sure someone would talk to her in school that wasn’t Arnold. But after a few classes it was clear that wasn’t going to happen. They would look, the boys often a little longer, but would move on and forget about her after. She looked around and realized of course they did, there were plenty of other girls wearing as good if not hotter outfits around her. She felt like a baby finally learning to walk while her peers have been running for most of their lives. She was anxious because she still felt uncomfortable in her new style but, the lack of real change made her just zone out in melancholy. Why did she bother looking up those youtube videos and spending all her allowance on this stuff if nothing changed. Until one of her classes a boy smirked at her.
He was one of the best guys in school. Best in almost every way you can think of. His parents were doctors, he got one of if not the highest grade in all his classes, he was on the varsity basketball team, and was the vice president of their class. So why would Eric of all people smile at her she wondered as she felt her heart pounding through her chest. She tried to follow every nanometer movement of his eyes. Before he looked away she noticed he looked a bit down. That’s when she realized it, her legs were spread wide because she is used to wearing pants. She blushed and closed them slowly. But found herself trying to hide the widest smile she ever had in school.
She tried it again during lunch at the library. She would seemingly absentmindedly leave her legs open but very few minutes would look up from her book to find herself being looked at by boys. Some of them weren’t very cute but she often wouldn’t even notice them enthralled by the cute boys noticing her instead. Near the end of the day in her second to last class when Arnold tried to talk to her she pretended to be focused on a book until he left her alone.
At the end of the day she closed her locker satisfied in her transformation into what she thought of as a real girl. “Hey” someone said behind her. It was Eric. He asked her what she thought of the current homework assignment for their mutual class. She said she’s already almost done. He then asked about other random things, like what colleges was she applying to, what major she was thinking of majoring in and more. Every sentence she felt like she was on the edge of a cliff and if she messed up could lead to her being miserable for her whole life. A part of her almost wanted him to leave so she could calm down. But then he suddenly stopped when she began to turn towards the hallway that led to the busses back home. “Hey so, want to help me with that homework I have so much practice this week I could use any time saver, I could drive you home after”. Before she could even think she found the words “ya sure let’s go!” come out of her mouth. They walked to his car and he drove them to his house.
“My parents aren’t hear don’t worry” said Eric. Somehow this made her more anxious but she couldn’t figure out why. When they got to his bedroom, the smell made her feel high almost. She immediately started unpacking her books and took out the homework as he sat next to her on his bed. “Problem 1 is easy if you just look up-” she started to say before Eric interrupted with “I know, I know, I did it already” he said laughing. “What?” she looked in confusion. He started to laugh more. “Cmon, didn’t you hear me in class answer questions about it, I figured you would be smart enough to realize I already did it and it was just an excuse…” “Excuse…?” she didn’t understand what it was an excuse for. Until he leaned in closer and kissed her. She completely froze but he kept going. Slowly she calmed down enough to figure out how to kiss back. She started to feel light headed.
She could feel her face turning red, but thinking about it only made her more nervous and turn even redder. Unable to do anything coherent she just tried to imitate whatever he did and go with his motions. His hands were on her legs and they felt so warm and nice. But then they started to move up under her skirt. He started to rub it and she let out a mumbled whimpering “no”. He didn’t hear, and she tried to say it louder but was nervous and using all her brain power to keep up the kissing rhythm. It’s just a hand it’s not a big deal she convinced herself after being unable to say anything. She thought of all the times she tried to masterbate herself but it always felt stupid to look at just picture. But, now she had to worry about her underwear being ruined. A few moments later it’s like he read her mind as he started to take her underwear off. She wanted to say no again but it was already off, and she thought maybe it’s better this way so that it doesn’t get ruined. She drifted as her eyes were closed and started to wonder how long this was going to last. Just then she heard some clothing hit the floor. She opened her eyes to find his pants were on the ground, but she didn’t have time to react as she found her legs being raised up. Her eyes went wide and she prepared what she was going to say “maybe I should say I’m on my period, or maybe I should just tell him I’m a virgin, but isn’t that embarrassing?” before she could decide what to say she already felt a piercing pain. At this point her body filled with adrenaline more than anything she could handle. Giving presentations was bad enough for her, she usually had to cut them short and walk out in embarrassment, and this was on an entirely new level. It felt like she was leaving her body. She tried to think of anything else. She couldn’t tell how much time elapsed but suddenly she heard him breadth a heavy sigh and roll next to her. He handed her a tissue. She could feel something wet coming out and rolling down her leg. She cleaned up what was on her leg.
“Wanna watch an episode then I’ll drop you off” Eric said as he pointed to a show on the monitor. Anna nodded her head even though she didn’t know the show and had no interest in it. Eventually the show was over and he dropped her off at home. The rest of the day was a hazy blur where she couldn’t focus on anything.
The next day she wore her normal outfits and everything was the same as ever. No one talked to her. Eric was talking to his friends in class and didn’t seem to notice her. She wanted to say something to him but felt awkward and had no idea what to do. She hoped he would be the one to approach her. Instead the only attention she got the whole day was Arnold. She didn’t have the energy to pretend to read and ended up letting him ramble on.
Life seemed to go back to normal until a few days later. She got a text from Eric saying he would come by at 8pm to pick her up. She panicked, quickly jumped into the shower and got ready. She didn’t have time for makeup or anything interesting. When she got into the car Eric looked at her normal outfit and sighed. But, Anna noticed they weren’t driving the Eric’s house. “Where are we going?” she managed to ask. He said “Eh, you’ll see”. Eventually he parked in an abandoned parking lot. It was dark and no one seemed to be around. He got out of the car and Anna mimicked him. He opened the back seat and sat inside, she followed. He immediately started to kiss her. Anna’s mind went blank and it things transpired the same way they did last time. This time there weren’t any tissues so Anna cleaned off what was dripping down her legs with her sweat shirt. After Eric dropped her off at home and this time she at least had the fortitude to do some homework.
Life continued this way for a few weeks until Anna noticed something about her body. She decided the next time she saw Eric she would talk to him about it. But in school she just didn’t have the courage. He was always surrounded by intimidating guys and the type of girls who used to make fun of her. But then he texted again. This time when she entered the car she planned on telling him immediately. Instead when she entered Eric said “jesus, you’re wearing that kind of garbage again…” and she wasn’t able to say anything. Eventually after they were done and Eric was pulling up his pants she said “I… I didn’t get my period”. Eric laughed and said “Maybe you should start dating Arnold then… tell him it’s his, we’re both asian after all”. This made Anna mad, really mad, she didn’t have the courage to show it but she decided not to talk or do anything with Eric again.
Instead she started to hang out with Arnold. She told herself it was to make Eric jealous. Eric though, didn’t seem to notice. So after hanging out with Arnold a few times she told him “Let’s have sex” in the middle of a movie, her parents always told her not to talk during movies but that’s all they ever did and she never cared for any of them. Arnold froze up but eventually said “uh… really?”. She nodded annoyed about how awkward he was being. She told him to get hard himself so they could get started.
He was having a very hard time getting it up and he kept blaming it on being nervous. This pissed Anna off enough that she sighed and turned on the movie again and played with her phone. Finally though Arnold said “I.. I did it!”. Anna sighed and took off her pants and underwear and put her legs up telling him to put it in already. After who knows how long he finally figured out how to do it. “Wait, shouldn’t I get a condom” he said. “No it’s fine I took a pill” she said. He managed to finish quickly and they went back to watching the movie.
Before the movie finished Anna got a text from Eric. She told Arnold to drop her off to her place right now. “My parents are mad about something just do it” she said when he complained. She managed to make it back with just enough time to switch into one of her new outfits. When Eric came it was the same as usual but this time she afterward she said “But, what about college?”. Eric laughed and said “I don’t think the world will miss much if you don’t go to college heh…” Anna got a little mad “What do you mean!” “What do you think…?” he said dismissively. Anna knew exactly what he meant, she wanted to bring up an achievement, something, anything that wasn’t just mediocre but she couldn’t. The best achievement she ever had was barely managing to get into the same classes as Eric and having the courage to wear a short skirt for one day.
Source: reddit.com/r/eroticliterature/comments/bttxs7/annas_first_skirt_mf_lite_noncon