The Shut in Caretaker (CrashJr)

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Re: The Shut in Caretaker (CrashJr)

Post by Shining Dreamer » Wed Jun 06, 2018 3:00 am

As the afternoon went on Ashley returned to the living room and watch some videos on his phone mostly wasting time and trying to avoid thinking about his caretaker. He noticed as Jen finished the laundry and walked into the kitchen fiddling around. It wasn't until Ashley could smell the food that he realized what Jen was doing. At one point he looked back at her and almost thought she was looking at him.


Ashley shook his head sure that he was imagining that and went back to the video he was watching. Jen soon called him to the table and he slowly walked over as she put the plates down and brought them spoons and drinks. Ashley watched until Jen was seated before he started eating figuring starting before her would be rather rude. The silence was somehow seemed to make the meal even more awkward and Ashley looked up to see Jen shoveling food into her mouth. Ashley then took a few more bites and couldn't take the quiet anymore, not really sure what to say but knowing things weren't going to get any better if he kept his mouth shut he looked over at Jen.


“Why did you take this job?” Ashley asked looking over at Jen half expecting her to say that was non of his business. He knew there were many other jobs out there for a girl her age, he also knew she was expecting the worst when she arrived. “I mean I sure there were other jobs you could of applied for.” He honestly really wanted to ask why she kept coming if looking at him disgusted her so much but held back. Ashley then waited to see if Jen would reply, if she didn't he wouldn't say another word to her. Though honestly he was a little interested in Jen answer as he's been wanting to ask her his since day one.

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Re: The Shut in Caretaker (CrashJr)

Post by CrashJr » Wed Jun 06, 2018 3:30 am

Jen was forced to stop when Ashley finally spoke, she was a little surprised due to him not having taking the time before to do so but also she was a little worried about looking up to him to explain something so trivial. "Okay" she began not wanting to looking up, "well my parents pre-ordered a game for me so I could have all the unlockables and the DLC right at the start, and I have to pay them back...which honestly with what your mom paid me I could have done with just the first day of work." she nods and glances up to Ashley. Looking back down she took a moment before she forced her head up, but her eyes looked to the ceiling and she began rub the back of her neck.

"And other jobs are to close to home...I'm...I'm not a fan of my parents. They can be overbearing and judgmental to be truthful." she nods again and she takes a quick glance to Ashley before looking away again. "So...what's with the trap look?" she let's the word slip out and before she could think she slams her hand on the table and looks right at Ashley. "I mean not trap...what is a trap anyway...totally haven't spent hours on looking it up...I mean yeah sure okay maybe I did but it's not like I was meaning to...I mean I meant to and...fuck..." by this point Jen was a deep red color from pure embarrassment that she knew she had caused so she did the only thing that she could think of, slamming her face to the table and ignoring the pain for doing so.

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Re: The Shut in Caretaker (CrashJr)

Post by Shining Dreamer » Wed Jun 06, 2018 10:07 pm

Ashley listened as Jen explained that she got the job to pay for some video game she wanted, though not why choose this job. Though after hearing her continue on, Ashley couldn't help but wonder just how much his mother was paying her. Honestly from the sounds of things she could of quit after day one, but that didn't explain why she continued working passed that. Ashley could even understand her picking this job because it was far away from home, if she didn't care for her parents. Though the idea that she take a job to get away from parents she dislike just to spend time with a person she found creepy and disgusting didn't make sense. She would just exchanging one person she disliked for another.

Ashley eyes became rather wide as Jen basically called him a trap a name that well a few people at school and the internet had called him. Honestly he was amazed that Jen knew the term as he never guess she was into that kind of thing. Ashley jumped him his chair a little as Jen banged the table with her hand likely thinking he might find the term insulting. Though soon it seemed she just seemed to ramble on about traps and Ashley couldn't help but wonder just what she was looking at last night. He could see her face becoming redder at the moment and at some point Jen burned out and hit her head against the table, and by the looks of it rather hard. Ashley honestly couldn't hold back his laughter and by the end of Jen little trap rant, and was laughing so hard he thought he pee himself.


“So you think I'm a trap huh” Ashley said trying to calm down his laughter, not wanting Jen to feel worst then she likely already did. He did get the idea that she was asking about his crossdressing and while he loved to have an easy answer, he didn't even understand himself completely. “Well if you think I'm one that find, I've honestly enjoy a few shows about them myself. Plus I totally wish I could of secretly gone to an all girls school instead of one where boys kept flipping my skirt when I wore them, and calling me well much worst things then trap.”


Ashley hoped that starting to try and explain himself with a little joke about wanting to be in a trap story would lighten the mood.


“Though as for why I'm like this well I guess there a lot of possible reasons” Ashley said thinking back on his life and how this whole dressing thing started for him. “Honestly I've always been more attracted to cute and pretty things even as a child. I also at a young age only had only girl playmates so maybe that's how I developed girly interests, I remember people saying that to my mom. Though really I high doubt that's the reason it seems way to simple. Though those playmates were the ones who first dressed me as a girl while we were playing. I can still remember them placing me in one of there old dresses. I was honestly shocked as I did look rather pretty if I do say so myself. I was even more surprised as everyone including my Mother smiled and told me I was so cute and pretty. I felt so much joy in hearing that, though I couldn't tell you why, maybe I have a mental problems. I guess that really doesn't sound like a good answer does it, I mean I could throw out a few more theories. Like that fact that I always enjoyed playing dress up and even as a child had an interest in fashion design. Though really all that I find that is important is that I like the way the clothes look, and the way I look in them. Really the honest answer is I don't even completely understand why I am the way I've become.”


Ashley released a large sigh realizing he ramble on for a good ten minutes without giving much of any answer. In fact he wouldn't be surprised if Jen felt more confused after hearing that jumbled mess.

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Re: The Shut in Caretaker (CrashJr)

Post by CrashJr » Thu Jun 07, 2018 12:10 am

Listening to his explaination helped some, but she was still very confused about everything and hearing him laugh after her breakdown, well it was a little hurtful. She guessed that she deserved it after the awkward last two days, but then again she had spent all night looking up things that would help her understand and none of it helped. So after a moment a thought she sat back up, a little blood trickling from her nose as she does so.

"I was up all night looking up anything to help me better understand, I first looked up crossdressing boys and...well you don't want to know the sites that pulled up. Then I kept looking then I found the word trap and found anime about it and...is it a gay thing? Like I don't want to judge, but in everything I saw and read it was always either a guy crossdressed because he wanted to be with a guy or something like that...and other cases...well I learned a lot about people called submissive and...well is it you're into guys or do you still prefer girls?" She was unsure as to why she was even asking. Yes she can mark it off to just having embarrassed herself lately and wanting to understand to help her stop from continuing to do so, but at the same time she felt her face redden looking at him which made her look away.

She was severally confused and would have to look it all up later when she could. For now, however, she was going to listen to Ashley hopefully give her a good explanation of things.

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Re: The Shut in Caretaker (CrashJr)

Post by Shining Dreamer » Fri Jun 08, 2018 3:56 am

Ashley couldn't help but get a good idea of what Jen must of found when looking up crossdressing boys as he had done the same before. Also as she talked about traps she wasn't wrong ether as a lot of stories about them were ether like she said stories about guys wanting to get with other guys or odd comedies that shouldn't of been taken seriously.


“Yeah I guess you learn a lot about uke's then” Ashley replied looking over at Jen who now had a nose bleed and wonder just what she was picturing. “Yes there are a lot of stories like that aren't there, but honestly Anime and manga are just the creator fantasy. Really while I sure there are likely guys who dress like that for that reason, I'm pretty sure there stories don't speak for everyone's reason. Though since you asked I'll be completely honest in the fact that I've never found another guy attractive. So to answer your question I do very much like girls, but don't worry I'm not going to hit on you or anything. I mean, I'm sure like most girls you'd much prefer a normal guy to one who dresses like me after all.”

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Re: The Shut in Caretaker (CrashJr)

Post by CrashJr » Fri Jun 08, 2018 10:04 pm

She nodded at his explanation and felt a lot better, but with the added bit at the end she actually got a little mad and leaned forward looking Ashley in the eyes, "what do you mean you won't hit on me...am I not hot? and what I even like guys like that...for all you know I enjoy guys that dress like girls...I could be into femdom for all you know" she scuffs and crosses her arms, she wasn't even sure what femdom meant in truth, she had just saw the word during her research. She honestly thought that it meant something like a boy that felt more like a female.

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Re: The Shut in Caretaker (CrashJr)

Post by Shining Dreamer » Sat Jun 09, 2018 2:47 am

Ashley at first was more then a little surprised that Jen got so bent out of shape after his last comment. Honestly he though she feel relieved, as most girls seemed to feel bad or guilty after rejecting him in the past. Though after hearing her next comment he figured she just took the comment as he didn't find her attractive, which was far from the truth. Though Ashley at this point was over the idea of dating as the few relationship he had with girls typical started with them being excited about his specialness and ended with them saying, they like him as a girlfriend and not much more. He was surprised at how upset she seemed and was more there a little surprised as she mentioned femdom without a hint of awkwardness, tell him she didn't know what it really meant. Looking up at the rather upset girl with her arms cross glaring at him closely Ashley figured he had better try to explain himself better.


“Look if you really like to know I find you perfectly attractive, or hot as you just put it” Ashley replied blushing unable to believe he just said this to Jen out of nowhere. “Also I guess it was wrong of me to assume what kind of guys you like. Though despite that you also have to remember that your my caretaker and well while my Mom is your true boss, I guess I'm also kind of your employer too. So it would be highly unprofessional for me to hit on you even if I really wanted too. Plus I wouldn't want to make you fell uncomfortable by doing so.”


Ashley was honestly sure that Jen wasn't interested in him in this way and hoped his improved answer would leave her a little less upset. Geez honestly even if Jen did like guys like him he was sure she never want to really go out with him. He barely kept care of his appearance any more and had become a lazy shut in slob to make make worst. The scar on his neck should be more then the icing on the cake to make anyone lose interest in him. While he knew there were girls out there with special interest Jen reaction these last two days told him she wasn't one of them.

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Re: The Shut in Caretaker (CrashJr)

Post by CrashJr » Sun Jun 10, 2018 11:48 am

Blushing a little she simply nodded and uncrossed her arms, "well thank you then..." she says and slowly begins to eat again as she begins to overthink the fact that he did find her attractive but the fact that he wouldn't hit on her was good, even if she felt a little saddened by the fact. She wasn't into guys like Ashley, she thought, but here she was jealous and a little sad that he wasn't going to hit on her. A flurry of emotion was not fun as her face showed hints of annoyance.

After a moment of thought she shrugged and got up to clean off the plates and take care of random chores here and there. After a while of doing the random things she leaned on the counter in the kitchen looking at her phone, it was about time for her to leave for the day and she was honestly a little sad to go. She was beginning to actually enjoy this place, yeah sure she wasn't sure if Ashley actually enjoyed living here then at home with his mom but she wasn't going to ask.

As her alarm went off she leaned off the counter and walked into the living room. "So I'm gonna head home I guess...today was...yeah" she nods and starts walking to the door, but as her hand touches the handle she stops and looks back over to Ashley. "Slumber party next weekend?" she asks not really sure what all that would mean other then her staying overnight here.

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Re: The Shut in Caretaker (CrashJr)

Post by Shining Dreamer » Sun Jun 10, 2018 3:15 pm

Ashley was glad that after he told Jen that he thought she was attractive she seemed to calm down. Though for whatever reason seemed to be annoyed about something, though what it was he had no clue. The two then finished there meal in silence and Jen did the dishes. Ashley then return to the sofa fiddling with his phone as Jen did some random chores around the apartment. Ashley was amazed at how clean the place was getting as there was now enough clean floor in the living room that Jen could vacuum most of it.


When Jen phone alarm went off Ashley looked over as Jen said that it was time for her to go home. He then watched as she slowly walked to the door and stopped. Turning back she asked Ashley if they could have a slumber party next weekend. Honestly Ashley wasn't sure what to make of the comment, though he figured if Jen didn't want to see her parents maybe that was the reason. Plus she wouldn't have to ride her bike from home and back if she spent the night which was another plus he figured.


“Umm sure we can have a slumber party next weekend if you want” Ashley replied not a hundred percent sure this was a good idea, but agreeing to it anyway. Honestly over the last few days he was glad to not be the only person in his apartment. Oddly enough even if Jen barely talked to him, Ashley liked the company as before she came he felt more then a little lonely.

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Re: The Shut in Caretaker (CrashJr)

Post by CrashJr » Sun Jun 10, 2018 4:20 pm

Cheering up a little she gave a nod, "okay well I'll see you after school tomorrow then" she gave a half smile and walked out making sure to close the door behind her. For a moment she stood just outside the door thinking about him agreeing to her staying over, she wasn't sure if he was fully okay with it but she felt the need to figure out what was wrong with her and the only way she thought was with this slumber party idea. With a nod to herself she quickly made her way to her bike and took off heading back home.

The rest of her day was uneventful as she lazily played a few online games and when it around time for bed she turned on he laptop and watched a few episodes of anime that she had found during her time researching the day before. It wasn't until 1 am or so that she finally went to bed, with her dreams filled with her and Ashley talking. The conversation playing over and over in her mind, each time she felt more and more awkward.

As he alarm blared a few hours later she got up and began to dress in her uniform for school, the same dull outfit all the other girls wore. A green skirt that went to her knees, a white blouse, and if she felt like adding it, a sleeveless sweater. buttoning up and tucking the blouse into her skirt she yawned as she walked downstairs to grab herself a coffee.

"Hey, pumpkin, how was the job this weekend" her mother asked from the table where she was smoking a cigarette and drinking a cup of coffee.

"Long and boring" Jen shrugged, lying, as she walked over to the coffee maker and made herself a cup.

"Well no job is that fun really...but your dad and I are proud of you either way...I just hope that this man you're cleaning up after isn't freaking you out or anything" she says with a hint of worry in her tone.

Jen thought back to the awkwardness, and in truth wanted to tell her mom, but she shook her head and lied to her. "No Ash is okay just a simple guy that isn't really able to take care of the things he has" she nods and leans on the counter drinking her cup.

"Okay just please don't get in over your head here...it may be okay now but you know men...just if he ever...tries anything call your dad or I and we'll come and get you" her mom nods taking a sip of her coffee.

"I think I'll be fine, mom, but thanks" she says with a small sigh before she leans off the counter at seeing the time. "Well I got school so I'll see you guys tonight" she says putting her cup in the sink and rushing out the door.

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