Summer Fling: Ch. 1

 Characters:

Katie (Queer Woman. Upbeat, Dominant, Seducing – A Side)

Jessica (Younger queer woman, Shy, Angsty, Insecure – B Side)

Genres: Lesbian, Transgender, Angst

Summer Fling

One-Shot

A-Side

It was a beautiful summer day as Katie strutted through the brightly lit street along the river. She stretched out her arms widely as if to stretch, a small bag hanging from her shoulder, swinging back and forth with Katie’s quick steps, projecting a play of shadows on the river behind her. She was completely covered by sunlight, the rays of light reflecting away from the small silver necklace around her neck. And it wasn’t just the sun shining onto her, she herself positively radiated with light. And wouldn’t she? It was a stunningly beautiful day, summer finally falling in, and after a pretty dower and boring spring she finally had a date again. With a real person. And they would meet in person instead of typing in messengers. It would be an understatement to say that she was excited for the day to come, not just because she really couldn’t share her “Spring Feelings” with another woman. Though she had met this girl online, they haven’t really talked too much. Apparently she also played video games, that much she knew, but not much else. It wasn’t that she didn’t listen, but the potential chance at a fling would admittedly cloud her mind a bit. If this girl was even half as cute in reality as she was on her one and only picture online, then she’d potentially be looking towards one hell of a good time. Her face formed a smug grin as she considered the possibility of an end to her recent “dry spell”.

As she took a left turn into a nice little alley way, covered by pretty blue-red awnings, inviting visitors to a nice little café called “The Dancing Mouse”. Katie looked around for her guest of honour. And at the furthest corner table she saw a young woman with dark blonde hair cowered over her phone while seemingly chewing on her lower lip. She moved next to her and proudly exclaimed “JessiCat69 is that you?”

The young woman whirled around to the person speaking to her, dropping down her phone in the process. “Ye- yes?” she shuttered.

“Heya sweetie kittens! It’s me Katie! Come on, get up and give me a big ol’ bear hug sweetcheeks!” Katie proudly shouted out while opening her arms wide for a hug.

The younger woman slowly and carefully as if trying not to trip got up from her chair and carefully tried hugging the woman shouting at her. Careful as if she expected her to break like a clay jar.

Katie quickly closed her arms around the girl, pushing her tightly against her like it was nothing, managing to slightly squish the younger woman. Then she sat down on the chair next to her, beaming at the girl. She was exactly like in the picture, perhaps even prettier. Admittedly her make up seemed to have been applied somewhat awkwardly, but Katie didn’t mind, she was too stunned by the cute little face, her shy little eyes hiding behind those thick glasses of hers, being held in place by a teensy little snub nose. Her sweet dark blonde hair falling over her right eye in bangs that would make a grade schooler blush. Katie tried her hardest not to immediately stare at the girl’s pink lips, but no doubt here, she was a little cutie pie, further underlined by her still nervously chewing on her lower lip and looking shy as all hell. “Damn, you’re even prettier in person than in your pictures.” she said while smiling.

“I’m not.” the girl answered quickly. “But you are very pretty.” she added.

Katie giggled at the girl’s very apparent awkwardness, but she didn’t lie, the girl was extremely cute to her, and her awkward shyness really was the icing on top.

“I like what you are doing with your hair, it makes you look so young and sweet, really befitting you. Especially coupled with this soft pink dress and the black skirt. Makes you look like an angel!” she smiled brightly.

The girl visibly blushed, until she nervously mumbled “It’s really nothing, just what I had. But...” she quickly glanced at Katie’s bordeaux colored bloused, then quickly looked away again “your blouse is also very pretty.” then she became silent again. After a few minutes of this silence and Katie just looking at her the girl spoke up again “I- I apologize, this is my first date you se- I mean, the first time I am meeting a new friend in person and-” she blurred out like a rock tumbler.

Katie smile brightly at her, putting her hand on the girl’s, cupping it. “Don’t worry hun, I get it! It’s all fine, after all we talked on messenger before. I’m the same me, just in person now!” she tried to calm her down, while sneaking her hand onto the younger woman’s. Her hand was so small and soft, counter what she expected given that the girl herself was fairly tall. The girl seemingly tried to pull her hand away, but she didn’t quite let her.

“Ye- yeah I know. But somehow it is still different. I- I am just so awkward with these things.” the girl answered. Avoiding Katie’s gaze.

“Oh that is just fine honey. Say have you ordered already?” Katie interjected.

The girl shook her head “No I- I wanted to wait for you.”

“Oh well then, in that case, why don’t we order? What will it be for you?” Katie inquired.

The girl shook her head “A coke, but it’s fine I can do-” but Katie interrupted her as she waved over one of the waiters.

“A coffee for me, and a coke for the lady over here.” she quickly ordered before turning back to the girl who had started blushing again. “Jessica right? That is such a sweet name, nice choice, suits you very well.”

The girl, Jessica, formed a slight grimass before answering “Thank you that is eh… very nice of you.”

Katie, noticing her awkward phrasing quickly apologized “Sorry, I didn’t mean it like that. It’s just… a pretty name.” she winked at her. “Soooo, you play Smash too, right? We talked about that I remember, which character did you main?” she changed the topic to something a little bit less intimate.

Jessica corrected the position of her glasses, then visibly relaxed. “Oh actually I’m a Zero Suit Samus main. Yeah that might be bit cliché, but she IS a very varied and quick character, and you cannot argue with quick characters. Also highly technical, given the frame data we have, she just turns out to….”

Katie smiled as the girl was finally not just calming down, but also losing herself in her passions. The way she used her hands to gesture impacting hit boxes, how open her eyes suddenly were, so completely devoid of her earlier fears. Katie just had to lean back and watch her for a bit. Occasionally she would ask further questions, but for the most part she just leaned there, sipping her coffee that had arrived as well, while listening to the feminine girl completely lose herself in the exploration of frame data, different matchups and how happy she was to meet another cool and pretty Smasher in her area. Admittedly she paid less attention to the girl’s words, than to her hands whirling around, and her dress moving around every time a soft gust of wind would move past them, allowing Katie to notice the girl’s fairly small chest. She felt great, and from how it looked like, so did the girl currently discussing stage layouts.

And as they sat there, discussing characters, stages and match ups while drinking together, it seemed they really did warm up to each other. Eventually Katie spoke up.

“Sooo, seeing as it is getting colder outside, what say you, we go to my place and you actually show me what you can do? Your doctor’s thesis on frame data in all honours, but what is it worth when later on I’ll body you anyway?” she asked smugly.

“Huh! You say that, but I will totally teach you a lesson Katie! And when I’m done with you, you will beg me for advice!” she boasted.

They both giggled, paid for their drinks and left the cafe.

-

Back at her place, Katie dropped her small bag in the corner and lead Jessica into her living room. “Make yourself comfortable honey, can I get you something to drink? Maybe a tea?” Jessica asked for something Green, so Katie disappeared into the kitchen to heat up some water. Then she went to her bedroom and peeled herself out of her blouse, instead electing to don a pair of short sweatpants and leave it at a muscle shirt with a fairly revealing cleavage.

Returning with their teas she put both of them down on the table in front of them, making sure to put them down while allowing Jessica to look down her shirt. She couldn’t see whether or not the girl reacted, but noticed her recoiling slightly. Then she walked over to the TV, got on her knees and bend over, turning it on and cramming her favourite controller out of the drawer. “Oh, I forgot!” she exclaimed, standing back up and returning to a visibly blushing Jessica. “Would you hand me that controller in your lap?” she asked, reaching out her hand towards the nervous girl who quickly gave her the controller before recoiling back. Katie giggled audibly, taking the controller from her and connecting it to the console. As she returned she sat down next to Jessica, directly next to her.

Jessica’s feet were shifty, they would nervously move around “Man you’re close!” the girl exclaimed nervously.

“Are you uncomfortable? Would you prefer a little more distance?” Katie suggestively asked.

The girl however quickly shook her head. “No I-, I actually like it. I MEAN I’M COMFORTABLE!” she answered. Resulting in Katie giggling suggestively again.

And so they played a round, resulting in Jessica winning.

“Told you Katie, this is what happens when you challenge a desperado.” she boasted playfully while laughing.

“Oh yeah? How about you try again hu?” Katie quickly replied, inching even closer to her. Them now sitting body on body together, their arms touching.

“By the way...” Katie started, turning towards Jessica, half her leg on the couch “When we messaged via messenger you told me how self conscious you were about your looks and your body and all that. But that makes no sense to me. You are sooooo incredibly cute and pretty. Even your skin is really soft. I felt it earlier on your hands, and I’m feeling it now on your arm. You are super soft!”

This position actually allowed Katie to track Jessica’s eye movement, and it was obvious to her what the younger woman would be looking at. She noticed her gaze moving to her cleavage, then quickly away from her entirely, then to her legs, then to her face and back to her chest. Really her gaze flipped around all over the place like it was the bloody Tour de France. It really made her wonder what she must be thinking right now. Was it enough? Was she turned on yet? She wasn’t answering her question immediately, no, she was calm, what was she thinking? Was she thinking about pushing Katie on her back and just kissing her? Well, knowing the young woman and her disgust with herself, she was likely stuck in a loop of desiring to stare at her, then noticing herself staring, looking away and hating herself for her desires, but also unable to look away. And it made Katie feel both sorry and horny. Sorry that the girl was tormenting herself like that, but horny for the girl’s lust, seemingly just slumbering in there, waiting to come out.

“N- Noooo, I’m not pretty. You are pretty.” she eventually managed to say, stuck in her loop of self-hatred. “You look really pretty right now...” she slurred. “HEY! Eh, how about we play another round and you actually play your A game? Since it was very noticeable before that you didn’t play your A-Game. Now I know you said you main Palutena, but it really didn’t look like you were completely comfortable with the character….”

She continued blabbering, so her slumbering lust had lost again. “Hmmmm” she sighed suggestively. “Well then...” Katie moved in closer again, skin on skin, her head on the girl’s shoulder. “Okay then, you got me.” she unpicked Palutena and quickly moved over to Ike. “Battlefield, 3 Lives, 4 Minutes Timer, give it your all honey.” with that being said, they entered another match. With Katie easily going 3-0 on Jessica.

“For all that is holy.” the girl exclaimed

Katie pushed herself against the younger woman. “Nice essay about that frame data, but your combo game really needs some help. So how about instead we work on something more comfortable?” Katie moaned suggestively

“Wa… what do you mean? I don’t know….” Jessica tried to answer, but she was cut off by Katie moving in planting a kiss on her cheek. “Ka---Katie! How, I’m not--”

“Shush now, you really need to work on that self-esteem of yours.” she leaned in further to plant her lips on the girl’s mouth, moaning quietly while kissing her. She moved back a moment, before climbing over the girl’s legs to now sit over her, again giving the girl front row access to her cleavage. Her arms resting on both of the girl’s shoulders. She looked suggestively at the girl. “Would you like me to stop?” she asked.

“P-please don’t stop!” the young woman begged. Resulting in Katie immediately planting another kiss on her face.

Katie leaned in closely and slowly moved over to her ear “You are allowed to peak now, sweetie. Allow yourself to peak.” she grinned while softly biting the girl’s ear. Then moving down while kissing her neck and her collarbone.

The younger woman however seemingly still had issues following through, her arms hanging down uselessly. “I- I don’t really wanna do the wrong thing. I don’t want to hurt y-” she was again interrupted by Katie.

“Hey now, how about we make a deal hu?” again kissing her mouth “Would you like to make a deal with deary little me?” she looked down Jessica’s eyes.

“Yeah. No. Wait. What deal?” she inquired carefully.

“For the next half an hour or so from now, you will do me a favour. Every time you are thinking of something, you will then do that, okay? You have to do the first thing you are thinking about every time. Not the second thing, not what that destructive part in you requires you to do. The first thing. Do what you desire baby. Okay?” she looked at her, waiting for an answer.

“Ye- yes. Yes Katie!” she answered, looking into her eyes.

“What do you want to do right now, little princess?” Katie asked.

“I- I really wanna kiss you.” Jessica answered.

“Well then, why don’t you do it?” Katie asked again.

Resulting in Jessica quickly leaning forward, kissing Katie back, who immediately fell forward, into the girl’s lips. So they sat there, kissing for a while, moaning quietly, until Katie grew greedier, her hands moving over to the girl’s sides and lovingly following them down where her fingers turned around and marched up the girl’s belt-line over to her navel, which she played with for a bit.

Noticing the girl’s hands still laying around she quickly moved up again, slightly distancing herself from the girl to quickly take off her shirt and reveal her chest, only covered by a white bra, to the young woman. “First thought sweetie, first thought.”

Like in trance Jessica actually became active. She slowly placed her hands on the Katie’s stomach, the moved over to both of her sides, then just sitting there, enjoying the view, embracing the moment.

Katie was happy, this is what she was waiting for. The girl just forgot her fears and insecurities for a moment and just letting go. From there she would finally be able to release. She quickly moved her hands back to herself to open her own bra and drop it to the floor next to her. Allowing Jessica full frontal view of what she desired.

Jessica took it all in “You are so stunningly beautiful. Can… Can I...” she stopped, looking at Katie just quietly smiling at her. And after a short movement she just leaned forward, her hands climbing up Katie’s body, over to her chest, which she started touching and cupping with her hands, resulting in Katie moaning lovingly while continuing to smile.

“Go on, enjoy yourself lover girl!” she reminded the girl who continued to stroke and softly squeeze her breasts. Making Katie exhale warmly and giggle occasionally.

She enjoyed it for a moment longer, and then her greed resurfaced. The leaned back forward. “They are yours whenever you want, sweetcheeks.” she planted another kiss on her lips, then her hands moved down and crawled under the girl’s shirt. “If you want me to stop, or you are not comfortable with something, please stop me, okay?” she whispered. Electing not to wait for an answer she continued up the girl’s stomach and over to her breasts which she circled for a moment before grabbing her shirt and pulling it over the girl’s head. After soaking in the view of the girl’s tiny breasts on her nervously quivering body she dug in. Leaning forward she started grabbing the girl’s breast-area and groping it wildly, then kissing her chest. “See I love how awkward and shy you are, but you really gotta learn to release. There is a horny little dyke sleeping in you, and she wants to play, wake her up, release her.” she taunted her, returning to kissing and groping the girl’s breasts.

Now it was Jessica who was moaning, and moving her hands down Katie’s sides until they stop on her butt, softly gripping it.

Katie smirked, moaning extra loudly to push Jessica further, her hands running down the girl’s chest and over her belt until they landed onto the girl’s pants between her legs.

Jessica quickly recoiled and closed her legs “No!” she quickly yelled.

“Are you not comfortable with me touching you there?” Katie asked.

“I- I- I- I’m not real down there. Please don’t hate me but… like I’m not really a woman down there so...” her stuttering was stopped by Katie.

Holding her hand over the girl’s mouth she slowly moved over to the girl’s right ear before quietly whispering “Buuuuuuuuuuuuuuuuuullllllllllllllshhhhhhhhhhhhhhiiiiiiiiiiiiiiiiiiiiit.” and moving her hand back between her legs. “Can I pleeeeeease touch it?” she said while moaning. “Pleeeeeease.”

“Please don’t hate me! Please don’t hate me! Please don’t hate me...” Jessica repeated liked a mantra while slowly opening her legs.

Katie, not however pleased with merely playing around on top of Jessica’s clothes, instead started moving along the girl’s left leg until she reached the entrance of her skirt, where she moved back up along her leg, under the skirt this time. Until she reached the girl’s panties.

The girl released a quick screech as Katie’s fingers started playing with the outlines of her erection from outside of her panties. She screeched again as Katie slowly pulled down her panties.

“Pink panties eh? Guess I’m not the only pervert here eh?” she giggled, dropping the pants next to her and then getting back up. She hopped off the girl’s lap and stood next to the end of the couch. “Come over here and please sit on the end part of this couch here, will you do that for me?” she asked seductively while gesturing for her to come closer.

Jessica swallowed visibly, then she slowly got up and walked over to the end of the couch, where on the elevated side she sat down.

“Good girl. Now… lift your skirt up for me and show me your dick.” she continued while looking directly into her eyes without blinking.

Jessica was just stunned for a moment, but even had to feel the horniness by now. So eventually she followed Katie’s orders and slowly lifted up her short skirt, revealing a small but erect penis to her.

“Hold it like this.” Katie commanded as she kneeled down and immediately started playing with the girl’s cock, first rubbing the shaft and then moving over to cupping her testicles, but moving in closer to take it in her mouth. The feeling was from out of this world. Nothing could come close to this moment of pushing down her lips on this girl’s little dick while it grew and got slightly stiffer inside of her. It slightly wiggled around in there, and it was so soft she would just pull on it, suck it while smacking hungrily and push it around inside her mouth with her tongue. And during all that this, the little girl in front of her just quivered, and squealed and moaned. Shaking her legs, breathing heavily. Little miss sunshine must be close to cumming.

Katie really wondered if there was any chance she could get her to stick it in later, but wasn’t sure whether or not she would be comfortable with it, or whether or not her estrogen induced dick could even be stiff enough for the process. Maybe she could rub up against it a bit later.

She still had a Strap-On in her drawer, but she doubted the virgin-esque girl would be up for it later. She didn’t desire to stretch the younger woman’s courage too much on their “first date”.

“You can cum if you want to. In fact, if you want to cum, please do so.”

She wasn’t sure whether or not that did it, or whether she had just arrived there anyway, but the under more and more louder moans and accelerated breathing the girl ended up cumming.

Her legs shaking, her body trembling, the girl was moaning like a bitch and red as a tomato as she pushed herself forward more. She didn’t really ejaculate much though, and it wasn’t very thick either - more like a thin translucent liquid. Yet it still tasted agreeably, and it just helped make Katie even hornier, if this date didn’t manage to scare the young woman away, then she would surely use further dates and meetings to enjoy the girl’s body even further. Katie looked up to the girl’s face, but her eyes were closed. A bummer Katie thought, she would have loved to see her orgasm face with open eyes and her tongue hanging out. But maybe that still was in it for her, if she continued this endeavor.

“Ka ha- ha ha Ka- Katie. I’m ha- I’m sorry, I….” she started rambling apologies but Katie stopped her.

Rubbing her feminine dick further she continued “No need to apologize, it’s been a while since I made a girl cum from oral, and it’s always a treat I gotta admit.” Besides the thick layer of self hatred, the desire for punishment, there must be a queer little degenerate. And she would find it, she would make it through all the layers and wake up the degenerate inside of her, making her the horny girl she was supposed to be, one orgasm at a time.

But for now it was time to do some aftercare and maybe make the girl return the favour by eating her next.