A Fateful Roommate Ch. 01

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College Trans girl finds roommate with matching interests.
2.3k words
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Part 1 of the 3 part series

Updated 06/11/2023
Created 10/15/2021
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Chapter one: A meeting of the minds.

Orientation day at the College had been extremely boring. Non-stop moving between great lecture halls and auditoriums to navigating the tunnels that connected the four main parts that made up the college. Cautions and warnings about getting lost in the tunnels, as they dated back to the war, were probably falling on deaf ears as Simone looked around and noticed that it seemed hardly anyone was paying attention to the middle-aged woman who was leading the orientation squad Simone was part of.

Eventually the lady announced the end of the tour and began reading out from a list of names so they could step up and receive their dorm-room number. Simone cautiously maneuvered around the students still waiting when her own name was called, careful not to rub shoulders with anyone and got herself a few pieces of paper that detailed how her life would be at the college. Room 209 of the East academy and if her memory wasn't off, a room ending in a 9 meant a corner room at the end of a hall.

"Lovely" she thought. "Privacy and hopefully far away from loud staircases."

Starting tomorrow students could begin moving their stuff in and the official start of the school-year was still 10 days off. Wanting to be far away from the mass of new students, Simone headed for her room, hoping that her roommate would do the same.

"And remember dearest. Make a good first impression with your roommate. You only get one chance at a first impression." Her mother's words from this morning before she had left.

Entering through the large intricately designed wooden doors of the East Academy, Simone quickly dashed up the stairs to the second floor without a wasted breath. She might be short and petite, only possessing B-cups and not much of an ass, but she had made sure to stay in great shape during her high school years. Following the signage, she turned to the left and just as she had remembered, room 209 was indeed at the end of the hall with a cleaning/storage closet opposite instead of room 210.

"Lucky me. Only one neighboring room" she thought, giggling to herself a tiny bit.

Opening the door, she was half surprised and half saddened at finding the room empty but decided to simply wait and hope her roommate would show up. The room itself was fairly small, though it possessed two windows, one on each corner side of the building. Simple beds, one to either side and a small worktable at the foot of each.

"First come, first serve." She thought as she picked herself the bed on the left. Finding her basic set of bed sheets from her oversized backpack, she quickly had the bed sheets neatly on the bed and pillow and decided to take a breather, lounging on the bed waiting for her roommate, still unsure whether she would even arrive. Looking at her phone, the display showing it was a quarter past one, still meant she has nearly 3 hours to kill before her parents would arrive, for a quick inspection then drive Simone home with them.

Time passed slowly and when the clock struck two, there was still no sign of a roommate.

"Maybe I lucked out completely and I won't even get a roommate." She said to herself, smiling without realizing it. Boredom had crept in and she got up to take a peek outside her door and down the hall and was surprised to see almost no traffic. An idea popped into her head, fueled by boredom and teenage horniness.

"Perhaps I can squeeze in a quick orgasm now before my roommate or parents show up."

She took a final peek down the hall and decided to take the chance. She hadn't been able to get her daily morning-orgasm as her parents had been nagging her all morning long.

Locking the door and pulling the curtains on both windows shut, she lay down in her bed and pulled off her skirt. Fumbling in her backpack, she managed to find a small bottle of lube that was almost empty. Applying a moderate amount to her right hand, she began gripping her already rigid cock and stroking it at a slow pace at first, making sure the lube was well-distributed.

Simone lost herself in the rhythmic pleasure of going up and down her shaft. While it wasn't exactly impressive, she could manage 5 inches on a good day. With her left hand, she cupped and lightly slapped her balls around while increasing the speed of her right hand.

Like a balloon being slowly filled with air until it suddenly bursts, she too was slowly being overcome with pleasure until she too finally burst and shot an extra-large load all over herself, managing to avoid her clothes by pulling it up, so it instead coated her bare belly.

Coming down off her bliss, she quickly and methodically cleaned herself up and headed for the bathroom to dispose the paper she had used, leaving her bag on the bed for the brief minute she would be gone.

When Simone returned, she was surprised to see another girl inside her room, in a cute lightblue top and brown curly hair down to her shoulders. Her roommate.

"Hi. I am Jessica, but everyone just calls me Jess." The girl said with a big smile on her face as she extended out her hand. "It looks like we are going to be roomies!"

"Hey. My name is Simone. So very nice to meet you Jessica. I hope it is okay, but I already claimed this bed."

"Of course that is fine, you were here first anyways. But please, call me Jess."

Jess was roughly the same height as Simone, it seemed. 5 feet, 2-3 inches she would guess. Jess had the look of a geek, with large freckles across her face and a pair of glasses that seemed almost too big for her small, petite stature.

"So what are you going to be studying, Jess" Simone asked, remembering her mother's words and trying to make that great first impression. "I myself will be taking on the enormous task of studying economics." She said in tones of dry irony, hoping to spot a sense of humor in Jess.

"Economics!" Jess exclaimed. "That sounds dull as hell. I am here to study microbiology" came the reply after she had given her bed and the worktable a closer lookover.

"So tell me more about yourself Simone. What is your story."

"Well..." Simone began before drifting off. "What is there to say really. I come from a boring small town, am an only child and..." she stopped again, looking past Jess's shoulder out through the open door as if she could see someone, though there was nobody.

"And what" Jess pushed. "Surely that can't be all there is to you."

Unsure whether to announce that she possessed a dick or if that would be way too soon and gross, Simone stepped past Jess and went to look down the hall. Still she saw nobody. Looking at her phone, it was not even half past two yet.

"So..." Simone began. "There is this one thing. But you will have to promise me that you will not tell this to anyone. It is very important that nobody else knows about this, but seeing as you are my roommate to be, I think you at least deserve to know. She finished, waiting for a reaction from Jess.

After a long pause, almost too long Jess timidly spoke. "Okay Simone. I promise that I will not tell anyone about this. Whatever this is."

Satisfied with that Simone cleared her throat. "I have a dick." Simone finally managed to say, hoping she wasn't blushing too much though her face felt crimson. "I know it isn't obvious when you look at me, which is why I need this to stay a secret."

The reaction from Jess was not at all what Simone had thought it would be. The first impression Simone had made of Jess, had been that of a shy, timid geek. Someone who under no circumstances would want to know any more about this entire ordeal. Yet instead of disgust or revulsion, something else painted Jess's face.

"Curiosity perhaps." Simone thought to herself, unwilling to look for too long into her face, instead planting her gaze firmly at the floorboards, hoping to hide her scarlet face.

"Really now." Jess finally said. "I would never have guessed. You really do look quite fantastic, especially your skin."

The compliment made Simone blush even more, as if that was possible. "I just thought you deserve to know, Jess. And I want you to know that there won't be any weirdness from me." Simone managed to say without making her horniness too apparent in her voice. She had just jerked off and yet telling Jess this had always been her plan, as part of the first impressions. But it still made her horny.

"However." Jess said in a low, demanding tone, that made Simone look up despite the feelings of hotness both in her cheeks and in her groin. "You are not done with telling me your story, though now I know what we need to narrow our focus to." A dangerous smile painted Jess's face that made Simone simultaneously shiver and feel the blood rush into her cock.

"What.. What do you mean, narrow our focus. I wasn't planning on saying anything more about it, I just told you that. No weirdness from my side." Simone replied, hoping she sounded more firm and confident than she felt.

"What I mean, dear Roomie is that I want to know more. A lot more in fact. Starting with whether you are a top or a bottom?" Jess said in such demanding tones that Simone almost started speaking without thinking. "And then I will of course need to see IT. That is non-negotiable."

Simone suddenly felt light-headed, the room spinning slightly. Had Jess just asked, no demanded to see her cock? And that was after she had told whether she enjoyed dominating or being dominated. What was happening today.

"I am waiting..." Jess said impatience coating every word as her foot tapped the wooden floorboards. "I believe I asked you a question and I expect an answer."

"Why do you want to know?" Simone asked nervously, not daring to hope for the reply she had dreamt of for close to two years now.

"I don't believe answering a question with another question is considered polite, Simone. Now answer me before I lose my patience."

Her words both aroused Simone and frightened her. Unsure of how to get out of this -- if there even was a way -- Simone settled on the simplest way. The truth.

"I am a submissive by nature." Simone said, this time her cheeks felt on fire, but she managed to not look away from Jess's gaze. She wanted to see the reaction to her words, more than she wanted to hide her shame.

"Excellent. Very nice of you to share such an important part of yourself with me Simone. Allow me to return the favor. See, I am a domme by heart and I suspect we are going to have a wonderful time here at the college. Now I believe you aren't done with your tasks for me, Simone." The way Jess spoke her name, she could almost imagine that it had been the word Slave instead of her name. Simone was brought back to reality by the throbbing of her hard cock and she just realized something. Not only was she going to show Jess what she was packing. But she was going to do it while she was as hard as she had ever been.

Not wasting any time she pulled her skirt down and her entire stiff cock and balls were hanging out on full display for her new roommate to see.

"You seem rather excited, Simone. Rock-hard some might even say. Tell me, when was the last time you came?" Jess cooed in a cool, almost serene voice.

"I came less than an hour ago, right here in this room. In fact I had gone to the bathroom to dispose of the toilet paper and when I returned, you were here." Simone blurted out quickly.

"Ohhh how interesting. And how often would you say you cum?"

"At least once a day Jess, and on the weekends at least twice."

"Naughty naughty girl. You do still want to be referred to as a girl, right?"

"Yes otherwise that would tip off anyone who isn't aware of my little secret." Simone said

"Little secret.." Jess said, amusement entering her voice. "Very apt choice of words. I must say, you are not very impressive to look at, but that is something we will have to take up another day. It is almost time for me to leave, as I have an appointment that I can't miss. However I do have one final question for you and it is very important you are honest with me here, Simone." Jess said and Simone felt a jolt in her cock that was still fully erect and exposed.

"Have you any experience with chastity?" Jess asked and a lightning bolt struck Simone's brain. Her mouth seemed to dry up and when she opened her mouth to speak after what felt like an hour, she could feel how dry her lips had been. "Had her dream just become a reality?"

"No first-hand experience, Jess" Simone said and she noticed a small drop in the smile that had been painted on that cute face for a while now. "However it has always been a fantasy of mine."

The small drop in Jess's smile instantly was replaced with a huge devilish grin and Simone felt a shiver down her spine once more.

"Well then Simone. Prepare yourself. It seems we are a wonderful match and as I said earlier, we are going to have a great time together, mark my words. Tomorrow your college life begins!" Jess exclaimed, bursting with energy and excitement as she left the room, leaving behind a stunned Simone who still had a raging boner and no clue what to do with it.

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AnonymousAnonymousover 2 years ago

More! Now!

AlproAlproover 2 years ago

Great start, please continue

AnonymousAnonymousover 2 years ago

Ground work laid; roommate, not yet.

AnonymousAnonymousover 2 years ago

Definitely can't wait to read more!

LtShiharamLtShiharamover 2 years ago

nice start, seems like it has a lot of potential. keep it up

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