Jessie Ch 8.3 – Two Steps Forward, One Step Back


Jessie walked down the path slowly, almost waddling from the strange sensation of his tight padded undergarments. A sensation that made him worry about the days to come. ‘How often should I change these things?‘ he thought. ‘Ash only gave me a few… Maybe I could coax her into buying a box for me so I don’t have to go through that embarrassment, too.

Despite being lost in his own mind with worry, Jessie had almost made it to his destination, the administrative building, before a familiar voice rang out from behind.

“Yoo-hoo~! Jessie! Can I talk to you really quick~?” it called sweetly, beckoning him away from his goal and his thoughts. He turned around to find the origin of the voice and was met with a smiling raven-haired girl, rocking on her heels with her hands folded behind her back.

“R-Rachel!” he squeaked, and then awkwardly coughed his voice down trying to sound more masculine. “What, uh, what up homie?”

“Y’know, I saw you at gym today…” she started. “None of the other girls recognized you, but I saw straight away. I’m…” she paused, looking about to make sure nobody could overhear her as she whispered, “I’m glad you stopped cross-dressing. It suited you, in a way, but I think I like you much better as a man.” Jessie blushed at the way she batted her eyes at him.

“I uh… the teachers made me do that, honest…” he fumbled with his words.

“It’s ok, I know you couldn’t have been a pervert or anything, not after what you did for me the other night. I admit, I was worried when I first had my suspicions, but I realized you’d never once looked at any of the girls changing. You only even changed with us because I made you. And for that, I apologize. I didn’t mean to make you uncomfortable.”

Jessie was surprised by her admission but didn’t really know how to respond aside from a simple nod.

“Well,” she continued, “I just wanted to ask you if, um… If you’d…” Rachel stuttered and her face turned red, unsure of how to continue, leaving Jessie curious.

“Go on,” he encouraged.

“I wanted to know if you would…” she gulped and took a deep breath. “Would you go out with me?” Her blush intensified and she turned away, unable to face him after such an embarrassing question.

Jessie was stunned but after being utterly defeated by mother nature earlier, he needed the confidence boost. Here was a cute girl who saw him for who he was and actually wanted to go out with him. Jessie was not about to waste this opportunity.

“Yes! I’d love to!!” he responded with tinged cheeks of his own.

“Really? Oh that’s great!!,” she shouted, spinning back around to face him. “I can’t wait! What would you like to do?”

Jessie’s mind ran over date ideas and all of the possibilities before deciding on the one thing he knew guys were supposed to take girls out to do, if media had taught him anything.

“Um… how about dinner and a movie? We can meet at the fountain on Friday,” Jessie said as smoothly as he could. ‘Oh, you player, you…‘ he thought.

“Is six alright?” she asked.

“Sounds good to me,” he replied with a suave grin.

“Then it’s a date~!” she cooed before stepping in and giving him a light peck on the lips. “I, uh, I gotta go. See you then!!” And with that, she was off, running back towards her dorms with a wide smile and cheeks as red as tomatoes. ‘I can’t believe I’m so bold! That’s twice now!!‘ she congratulated herself.

Jessie touched his fingers gingerly to his lips, still fresh with the soft sensation of hers. “I man it up a little bit and already I got a girlfriend. I really am all that is man,” he muttered, only to be distracted by another sudden pang.

Jessie kept walking towards the office with his head held high and seemingly nothing could bring him down. Despite the brief detour from gym, this day was shaping up to be pretty great so far. He’d proven himself to the class, put an end to the gym uniform nonsense that the teacher started, and now he’d gotten himself a date. Nothing could bring him down.

That is, until a certain familiar voice began shouting his direction.

“Hey you, just what do you think you’re doing to my sister?!” it called, sending an instant chill down Jessie’s spine.

As soon as he recognized it, he froze in place, unable to face him. ‘Oh no, not him, not now…

“I’m talking to you, punk! Who said you could kiss my sis– huh?” Daniel grabbed the short kid by the shoulder and spun him to see his face, but he locked up when he did.

The face scowling before him was familiar and yet somehow he just couldn’t believe it. Those big, bright green eyes and those flushed cheeks seemed to remind him of someone who’d really never left his mind; not for the last month and a half, and certainly not after Saturday night.

“S-she kissed me, man! Go ask her!” Jessie nearly faltered under Daniel’s gaze but the older boy seemed to ignore him, totally lost in thought. Lucky for Jessie, he didn’t quite seem to recognize him as the girl he’d kissed a few nights ago.

Or so he thought.

“D…do you have a sister named Jessica?” Daniel cautiously asked. They were the same height and looked so much alike but something about the boy before him was so different.

The hair was different, that’s for sure. It was a lot shorter but at the same time, it could easily work for a girl. But if this was Jessica afterall, why was she wearing the guys’ uniform? Wouldn’t she get in trouble? And why would Rachel be kissing her?

This boy and Jessica seemed so much alike and yet so different in subtle ways. His attitude was probably the biggest difference; a far cry from Jessica’s polite shyness. The only conclusion Daniel could come to was that perhaps they were…

“…Twins! Yeah, I, uh, I have a sister. We’re twins. What of it?” Jessie played along, taking the easy out.

“That explains it then. I, um…” Daniel paused, unsure of how to continue.

He’d been ready to pounce on this guy for kissing his sister but was he any better? With the way Jessica ran off the other night, with the hurt that was on her face, her brother would be furious at him, and rightly so.

Daniel spent the rest of the weekend worried about Jessica and beating himself up for what he’d done. It was foolish and he tried to justify it as having read the moment wrong and gotten caught up in it, but when he saw that look on her face, he knew he’d messed up big time. He wanted to make things right any way he could, but his mind was drawing a blank.

“Is there any way I can meet her?” he finally asked. “I want to apologize for something that happened a few days ago and I don’t know how to get ahold of her.”

Jessie paused at the bold request. ‘You want to apologize now?!

“Piss off, she wants nothing to do with you,” he seethed.

Daniel looked hurt, but determined. “So she’s told you about it, then. If I were in your position, I’d be upset too. I get it, man. I really do. I feel really guilty about pushing myself on her and I want to do the right thing and apologize. She can slap me and walk away for all I care, I just… I need to set things right. For her honour and for mine.”

Jessie carefully studied the older boy’s face and he really did seem to mean it. Hell, it looked like he was about to cry. Was this really such a good idea? To give him a chance to say sorry? ‘He stole my first kiss, I can’t just let that go so easily,’ Jessie thought. ‘But if he’s feeling this guilty about it, he can’t be that bad of a person…

Would it be ok just to let him say his piece and then never seem him again? Jessie’d already decided that, if he had it his way, ‘Jessica’ would never show up before him again. But, on the other hand, maybe one last time would be alright. Slapping him with all of his strength sure would feel good right about now.

Jessie sighed at his own conflicted feelings and after a moment, simply replied, “…I’ll think about it.”

Daniel’s expression softened a bit and with a simple thank you, he patted Jessie on the shoulder and took off, leaving Jessie back to his business.

“I guess that just leaves one more jerk to deal with,” he spat aloud, turning back towards the administrative building.

Duncan Moore, the dean would like to see you in her office. Duncan Moore, to the dean’s office.” The announcement rang out through the school building, on the campus, and through speakers lining the hallway ceiling in the dormitories, alerting everyone on campus that the bully was in trouble once again.

“Oh-ho! Trouble with the dean again, Moore?” the senior boy who always seemed to be wearing headphones called as Duncan walked past the reception desk.

“Oh, stuff it. I haven’t beaten anybody up in weeks,” he replied without so much as a glance.

Duncan made his way to the dean’s office, his mind racing all the while with the possibilities of what he might be in trouble over, but his worries were replaced with simultaneous relief and confusion when he opened the office door to find the dean at her desk and Jessie looking over at him with a scowl.

“You called for me?” he said, closing the door behind him.

“Have a seat, Mr. Moore.” Dean Winters motioned to the chair beside the grumpy-looking Jessie.

Duncan carefully sat down. Dean Winters was intimidating, for sure, but Duncan was even more intimidated by the cold aura radiating from Jessie. He hadn’t seen her in three days and now he meets her again in the dean’s office of all places. This could not bode well.

“Mr. Oliver here has brought it to my attention that you are aware of his… situation. Or shall I say, her situation.” Jessie winced at the pronoun but didn’t say anything of it. “I have given Miss Oliver special permission to stay in the boy’s dormitory under the condition that nobody find out that she is a girl, but according to her, you recently found out.”

Duncan lowered his head in shame, realizing that his screw-up on Saturday really was to blame for Jessie’s absence. “Yeah, it was an accident though. We had an argument and sh-, er, he hasn’t been back since.”

“I am well aware of your history of messing with other students and any sort of blackmailing or physical abuse you give her will result in immediate expulsion, do I make myself clear?”

Duncan nodded with fear in his eyes.

“Good. Despite Mr. Moore knowing about your situation, you still wish to stay in the boys’ dorms, is that right, Miss Oliver?” she said, turning to Jessie who winced again at the feminine title.

“Yeah, now more than ever. I can’t be put in the girls’ dorms, not now,” he pleaded.

“Well we do have one more opening, a single room near the stairs. You’d be alone, which I imagine you might prefer given the circumstances. This will be your last chance though, understand? I can’t keep covering for you every time someone finds out. You have to be even more diligent from now on.”

“Yes ma’am.”

“And you, Mr. Moore. Can I trust that you will keep this little secret of ours? Jessie’s situation is a tad complex and, for her safety and the sake of her education, I’d prefer it if we didn’t have any further problems. Perhaps you can even keep an eye out for her and make sure she stays out of trouble.”

“I can do that. That’s basically what I’ve been doing for these last couple of weeks.”

“Good. If everything works out alright, maybe you’ll end up better for it. Jessie has told me about how you made amends with your recurring victim and you haven’t had detention for over two weeks. I’m glad to see you turning a new leaf. Let’s keep this up, shall we?”

The smile Dean Winters gave Duncan sent a shiver down his spine.

Duncan was happy to hear that, despite what happened between them, Jessie still vouched for him. ‘She probably said it just to stay in the dorms, though. If I hadn’t have stopped fighting, the dean would think Jessie was in big danger staying with me and take her out of the dorms, for sure,‘ he thought.

They were excused from her office and hiked down the stairs and out the building without so much as a word, let alone a glance between them. Duncan could feel the tension in the air all the way back to the dorm, but was afraid to break it. It didn’t seem like Jessie was in the mood to be prodded.

Nobody spoke until Jessie told the senior at the reception desk that he was switching rooms and threw his key on the counter.

“Ooooh, trouble in paradise, huh?” the boy said with a sneer.

“Keep the snide remarks to yourself and just give me my new key,” Jessie snapped.

“Jeez, take it easy man, I’m only joking,” the boy said, handing Jessie the new key and throwing his headphones back on.

The two walked up the stairs to their formerly shared room and Jessie began packing his things one by one into the bag he’d been carrying around all day. First the clothes from the dresser drawers and then the books from the top. Duncan couldn’t help the guilt washing over him as he watched Jessie mechanically go about his business. This was all his fault and he knew it.

“Do you want some help? I can carry something over if you want,” Duncan tried to offer.

Jessie just grunted back, “I’m fine, I can do it myself.”

“You sure? I don’t mind.” Duncan was desperate for anything he could to to begin getting back on Jessie’s good side but he just wasn’t having it.

Jessie sighed after placing the last of his books in the bag.

“Listen, I haven’t forgiven you for peeping on me or for daring to have a crush on me. I don’t want anything to do with you. Just leave me alone.”

With that, Jessie was out the door without so much as looking Duncan in the eye, leaving him all by himself to plop down on the lower bunk of his bed.

“I really screwed up, didn’t I?” he said to the bars above. The acid in Jessie’s voice was enough to push Duncan away for who knows how long. “What can I do?”

Jessie found his new room at the end of the hall right by the stairs. It was a smaller room, housing a twin-sized mattress, a desk, a small dresser with a TV and a tiny little bathroom to the side. At first glance, the word ‘cozy’ popped into his head, conceding that while it might be crampt, it was a big improvement over having a roommate.

“This will have to do,” he said, tossing his bag on the bed and diving into it.

The book collection found its new home just where it was before next to the TV and his paltry collection of clothes didn’t come close to filling the three wide drawers available. When he finally got to the pads Ashley gave him, he stopped, being reminded once more of his new problem.

“…I guess they’ll go in the sock drawer for now.”

He threw the squares into the drawer and slammed it shut. ‘I need to get some tighty-whities or something. I can’t keep wearing these compression shorts every day,’ he thought, being brought back to the major problem of the day. ‘Maybe I can go shopping soon. Should I invite Ash along? No, she’d probably just make me wear some girly things… but then again, she seemed to be supportive of the ‘new’ me. I’ll have to think on this…

After a shower, and with the long day finally over, Jessie collapsed onto his new bed. To sleep away the rest of the week would be too enticing an idea.

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