Summer Fling: Ch. 4

 Characters:

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

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

Genres: Lesbian, Transgender, Angst 

Summer Fling: Chapter 4

Act IV: Thought and Motion

Katie was as if frozen, her mind was nothing but a complex matrix of desires, ranked in order of how quickly they could lead to her receiving the girl’s cock. 

“Katie? Are you alright?” the girl eventually asked, awkwardly sitting on the unmoving woman’s lap. “D-did I say something wrong?” she timidly added.

Katie didn’t react, her mind was playing a movie. Tonight’s playing: the director’s cut of girl Jessica awkwardly trying to move around inside of her and moaning like a little princess, shot from the point of view of Katie. Unbeknownst to her, a massive grin formed on her face.

“Katie, you’re making me concerned, are you alright?” the girl repeated.

Katie’s hands returned to the girl’s genital, that was now completely flaccid again. She snapped back into reality and softly pushed the girl off her lap before hopping off the chair herself and rushing over to her drawers. She scrambled through them, then quickly closing them to open another drawer which was then being searched in the same way.

“Katie? What is up? What are you looking for? Pleeease! Talk to me.” the girl begged.

The red haired woman whirled around and leaped back to the girl. “You… when you said you were thinking about putting your dick in me, were you serious? Would you do that?” she asked, her expression desperate.

The girl just blinked, her expression more confused than anything else. “Uhhh…” she paused “I suppose so? Would that be okay with you?” she innocently inquired.

“Okay with me? That would be positively smashing! You can’t imagine the last time I had a dick inside me!” she almost snapped.

With the girl not replying anything she moved on “Yeah yeah I know, don’t look at me like that. I don’t look it, do I? But I happen to actually really enjoy being filled up like that. And men… well…” she chuckled dryly “Men are okay. Problem is two-fold though, a) men often don’t view their dicks as one tool out of many but instead as their primary attraction, which I find disagreeable. And b) speaking of primary attractions, while men can be sweet…” she paused her speech, but came closer to Jessica, making her slowly retreat backwards only to have Katie keep up the distance between the two “...I vastly vastly prefer sweet little girls. Little cutie pies, all innocent to the outside, but filled with desires and depraved fantasies on the inside, just waiting to spill out. And I want them to spill out, I want you to lay them all bare for me.” Jessica ended up with her back to the wall, resulting in Katie now being directly in front of her, within reach of her face. “Tell me Jessica, tell me about depravities while I feast on your flesh...”

Up until this point, Jessica really wasn’t sure whether to be highly aroused or scared for her life, and this just didn’t help with that decision at all.

“I’m just fucking with ya, sweetie…” Katie gave her a quick kiss on the cheek “You just happen to be extremely sweet AND be in possession of a penis. And if I may be a bit blunt here, most of you girls aren’t exactly eager to use your junk for penetration. Piss poor luck for me though, since I enjoy it quite a bit.” she turned away from Jessica and returned to the drawers “I could have sworn I had some Viagra here somewhere, my dealer gave them to me a few months back, for exactly these kinds of issues. But fuck me if I knew where they were.”

“I- uh, I’m not sure I would be particularly good though. I mean I’ve never done it, besides, I don’t really get hard enough for that I don’t think. I was only a thought, you know, I don’t think I’m actually able to pen- penetrate you like that.” she did not enjoy saying that word.

Katie turned back to her and shook her head “Don’t worry hun, with these little pills you’ll be rock hard. I tried them on an ex once, and- now he was a dude, but I’m sure they’ll work on you too. They’ll need to bring construction workers to get your cock back into a flaccid state. Good thing your cock is so small.” she snickered

This actually resulted in Jessica blushing and avoiding Katie’s gaze “I- I- uhh I suppose I would not be good either way then, I AM pretty small down there, aren’t I?” she coyly admitted.

But again Katie shook her head “Hogwash, your dick is small yes. But that is how I like it.” she closed the drawer and walked over to Jessica, sitting down on the bed next to her. “Your small little tingly dick, I love it. It’s so damn sweet and feminine, and you shaking, almost like you’re afraid of me, kind of makes it even better. And yes, I suspect you’d be quite awkward at getting it in. And exactly that would be the cream on top of the ice cream.” to Katie’s surprise Jessica was averting her gaze even further. 

Katie made it comfortable for herself on the bed, she slightly leaned backwards, using her hands behind her back to hold her upright. She slung one of her legs over the other and tilted her head cheekily. “Look at me Jessica. Look into my eyes, right now.”

The girl awkwardly attempted to comply, but it was noticeable, both by her facial expression and her body language that she was still quite embarrassed and uncomfortable. There was a moment of silence between the two, it kept up for quite a bit. With the girl just trying her best to look into the woman’s eyes, who in turn switched between returning her gaze and studying her body language. “Say…” she eventually spoke up “how do you see yourself with me? What do you think, do I see in you? What is your role in this relationship?” the girl’s expression dowered even further, “I don’t know.” she eventually mumbled, hoping the answer would suffice.

“See, I’m only asking because you seem to lay under this constant stress of devaluing yourself. And I’m sure that partly has to do with your terrible self image. But it also seems like,” she paused for a chuckle “ironically enough you seem to be under this illusion that you have to be this crazy dominant fucker here. That even with a request like this one, I expect you to throw me on the bed to ram your hot thick meat into me. And your awkward inexperience is somehow keeping you from achieving that. I want you to know, it’s not me who has this image. You are projecting that image onto yourself right now.” she gestured for the girl to come towards her “Look, if you were someone else, maybe I’d read that as your underlying wish to dominate me like that, but your body doesn’t speak brat, your body speaks scared. You don’t have to dominate me, or possess some kind of rock hard meat. You’re my sweet little princess. All you’d need to do is put it in, and then we enjoy ourselves together. It doesn’t even have to be inside the whole time. We’re both adults, aren’t we? We can just play together.” she pulled the girl into her arms and gently caressed her, stroking through her hair.

“You would try to stick it in, and then just, enjoy yourself a little bit. Try it out. And then, when you’re comfortable, you can continue. Or if you prefer, I could ride you a little bit, sit on your lap if you’d be into that. And while I’d really like it up my ass too, that is something we can work up to, don’t you think? We have all summer after all.” her hands wandered down to the girl’s exposed butt. “Saaaay- when you masturbate, do you sometimes put something into your ass?”

Jessica recoiled in shock about the question. “What did you say?” she asked awkwardly.

“Oh come on, don’t play coy. I asked you if you pleasure yourself with anal stuff sometimes.” Katie rolled her eyes.

“So-sometimes.” Jessica answered. 

“Cause I’ve been wondering, given that we were just about to talk about this. Well, I’ve been wondering if maybe that way I could get you hard again. And… no. NO! I have a great idea!” she jumped up from the bed and left the room, disappearing somewhere in the hallway.

Jessica rolled into a ball on the bed. “I don’t know why I’m feeling so scared now. It’s not like she’ll hate me, right? She isn’t going to hate me, or think I’m disgusting. I can tell her what I like, right? It’s so embarrassing to be asked about these things so openly, but she did say that she liked depravity. Maybe anal isn’t even that depraved, what am I thinking? She probably knows some really depraved shit. And what I like is just really boring to her.” She rolled around on the bed, still almost completely naked, only her black skirt on her body “She’s probably getting some kind of crazy dildo now to torture me or something.” she blew raspberries into the air.

Then Katie returned to the room, her hands behind her back. “Turn around and get on your knees please.” she softly commanded. 

“Oh no what is it? Please no big dildo, okay?” Jessica gently pleaded. 

Katie however was in no mood to argue, quickly repeating her command in a more directing tone “Get on your knees, in front of the bed.” 

Jessica complied, she left out a sigh and knelt down on the floor. Katie quickly leapt behind her and furthermore pulled the girl’s hands behind her back. Suddenly Jessica felt a coarse and rough feeling on her wrists. “What is that?” she asked, panicking slightly.

“It’s just rope, don’t panic. Just keep still, will ya?” And as Jessica stopped struggling, Katie continued to bind her hands together and her wrists behind her back. Then she pulled her up from her knees and leaned her upper body over the bed, essentially bending over it with the rest of her body still hanging down from the edge, her knees barely making it to the ground. Then Katie sat down behind her. “Tell me if it hurts, in that case I can bend you over on the ground too.” then she cracked her knuckles, she moved slightly closer to the girl’s behind and slowly lifted up the backside of her skirt. “Nice ass.” she pointed out, as she took her hands and spread the girl’s buttcheeks. 

“This is so embarrassing, please don’t judge me! When I got up today, I didn’t know the day would end like this.” the girl pleaded.

“Well, you’re out of luck there. I AM judging you, and I like what I am seeing. What a cute little butthole. So… how often are fingering yourself? Think fast, your answer might direct what will happen next.” she snickered loudly.

“I uh… not often. I do it sometimes, but not much, it feels good but it’s so hard to reach down theeeeeeargh arrgh.” she couldn’t get very far, as Katie had already started pushing her index finger into the girl’s butthole. With the latter making her discomfort heard. “Stop! Stop please! It hurts!” she pleaded. Resulting in Katie actually pulling her finger back out.

“I’m sorry, I thought you were shitting me, and that you actually did it quite a lot. I did not mean to hurt you.” Katie quickly apologized.

“I don’t do it that often. Please don’t do that again!” Jessica repeated.

“Okay I won’t, promise. But… do you like anal? Generally speaking.” Katie asked.

“I- I’m okay with it. It can feel good, it’s just a clunky mechanic if you get my drift.” she answered in a slightly stressed out voice.

“Ca… can I-, I mean do you think I could train your butt? Don’t worry, I won’t rush you or anything. But we have all summer together, can I prepare your butt for anal sex?” Katie continued asking, so much motivation in her voice.

“I uh... what do you mean by ‘preparing’ my ass?” Jessica tried to turn her head and look at Katie, but found herself unable to.

“You know, stretch it. Help you loosen up a bit, play with your butt on a more frequent basis, finger you a bit, and then slowly increase the amount of fingers I am using. Essentially training your butt to be able to take more and more, make you my little anal slut, so I can fuck you in the ass. I have a few different sizes for strap ons, but even the smallest one will require some loosening up.”

“You… you would like to use a strap-on on me?” Jessica asked like a little puppy.

“Absolutely, from the very get go I was fantasizing about bending you over something and nailing you from behind, I want to hear what sweet slutty sounds will make when I do. See when I suck you off, or rub you, you will make nice little sounds and eventually cum. But if I can get you to enjoy anal, then I’ll fuck you until you will almost start roaring. I could make you get louder and louder, cry out and put some bass into that voice. I want you to moan like the degenerate fuckslut you are. Please can I?” Katie begged again.

Jessica couldn’t believe what she was hearing. This woman wasn’t just okay with her existence, she seemed in fact more than happy to make her her little project. Loosen her up and make her moan. And Jessica would be lying to herself if she didn’t admit that she was really into that idea. Moaning loudly, she had never felt that horny. Sleeping with Katie was good, but feeling that good? Was that even possible? The thought excited her, despite her knowing that it was likely impossible. “Eh sure, good luck with that.”

“So I CAN make you into my cock hungry anal slut?” Katie asked again.

Cock hungry anal slut, there is was again, a completely over the top title that nonetheless managed to turn Jessica on. As cringy as it sounded, this wasn’t some dumb chud on the internet. Jessica desired this woman a lot, and to hear her talk about her like that, it couldn’t do anything other than turn her on like crazy. “Yeah, turn me into your slut.”

“Turn you into what kind of slut?” Katie coyly asked coy.

“Uggghh okay. Turn me in your cock hungry anal slut. I guess. I just don’t like the cock addendum is all.” she repeated, with annoyance in her voice.

“AWESOME! And right now, can I please you, and by extension myself, by enjoying your sexy butt a little bit?” Katie continued asking.

“Eeeeeh, sure?” Jessica answered, slightly confused. But the true meaning of that would swiftly follow, as she suddenly felt something warm and wet push against her butthole. It moved around up and down and felt so warm, almost like it was hot. It also seemed to spawn hungry moans. No doubt it was Katie rimming her. 

This entire time questioning the girl, Katie had been hungrily staring at Jessica’s butt, and this was it, this was the sentence that allowed her to go; to greedily push her face between the girl’s buttcheeks and hungrily eat her out, only to have her wiggle around and struggle. But it was too late, Katie hungered.

Katie struggled to determine what she enjoyed the most, the view in front of her eyes, or the girl’s reaction to being eaten out like that. The sight was quite a thing to behold, the girl’s ass right in front of her face, with the ability to easily pull away her buttcheeks and enjoy an even better view. Below that hung the girl’s testicles, small and soft. For a moment Katie wondered whether it was the hormones that turned the girl’s balls so small, but then it really didn’t matter. They fit the image after all. Small and soft, more pink than brown and so smooth. Katie’s hands wandered down towards the small package, cupping it, pulling it up, weighing it in her hands. Then she pulled her hands away, watching the balls slowly wiggle back down. She poked them with her index finger, making them jiggle slightly. Katie wished for this moment to never end. To have this girl on the bed in front of her, her hands tied up and her weight and position pretty much keeping her from getting away, unless she were to roll off the bed. All she could do instead was quietly moan and tremble in embarrassment. What an exhilarating sight to behold, her tiny balls wiggling every time she trembled, her dick on the other hand was almost invisible in this position. Were she to get another hardon, the bed would likely be too close to her junk, making it painful for her to be in this position. Meaning time was at the essence when it came to enjoying this position. 

“W- w- what are you doing there Katie? Is something wrong? It feels weird.” Jessica stuttered, shaking even harder.

“I’m playing with your balls, silly! Your smooth tiny balls. They’re so small, they look so cute from behind!” Katie replied with the cheekiest glee in her voice.

“Please don’t say that, okay?” Jessica pleaded, seemingly stressed out.

“Don’t say what?” the woman asked “Don’t want me to call them your balls?”

“Please don’t call them tiny, that is so embarrassing.” the girl complained.

“But they are. They are so small. And so smooth. Big balls are gross Jessica, really gross. What you have here is so cute and feminine, I wanna… I wanna just nibble on them a little bit!” Katie’s voice being filled with an even stronger degree of glee and wonder, she had just lost herself in the sight. She lowered her head, pushed the girl slightly upwards with her hands while her face slowly slid into the opposite direction. With her tongue out she worked herself down the girl’s taint like she was following a trail of treats. As she reached the end she pushed her entire mouth over the girl’s testicles, attempting to get as much of them into her mouth as she could. Resulting in the girl moaning loudly. Which Katie swiftly replied to by pulling the balls out of her mouth and slapping her hand across the girl’s buttcheeks, resulting in a loud slapping noise. 

“No! Don’t, it’s so embarrassing down there! Please don’t!” the girl pleaded.

Katie poked the girl’s now wet testicles, again cupping them in one of her hands, weighted them, one of her fingers pulled to the side to feel the girl’s relatively flaccid penis. “If you don’t like it down there, why the fuck are you shaven so cleanly down here? How often DO you touch yourself down there? Be honest to yourself you dumb slut, admit how much you’re enjoying this!” she yelled, spanking the girl’s butt again, slapping those cheeks twice, the latter one harder than the previous one. 

The girl moaned loudly, her bound hands wiggling around, but to no avail. 

Katie grabbed the girl’s buttcheeks, squeezing them between her hands, almost clawing into them. Then slapping them again, violently pushing them apart and tightly gripping them again. “Answer you dumb whore! Tell me how much you’re REALLY loving this.” Katie roared at her.

“Katie.” she moaned “Katie…” she couldn’t say it.

“Tell me, slut!” she roared again, spreading her cheeks apart, pushing back together, and then pulling them apart again. Slapping her ass for good measure. Her fingers moved over to the girl’s butthole, rubbing it from the outside. “Tell me, or do you want me to finger you again? Will being inside you tell me all your secrets?” Katie taunted the girl. Putting her index finger on the girl’s butthole and pushing against it as if to enter, but pushing downwards - mostly to further emphasize her intentions.

“Katie, I’m so horny. I’m baaaad.” she mumbled

“You’re bad?” Katie asked, genuinely surprised about the girl’s reaction.

“I’m bad, I’m real bad. Please Katie! Make me feel good. Pleeeease.” she begged 

“Oh yeah?” Katie snickered. She started slowly pushing her finger into the girl’s butthole, making her gurgle out in what still seemed to be an expression of pain, but she didn’t ask Katie to stop. “Tell me how baaaaaad you are, sweetheart.” Katie added seductively. 

The girl didn’t answer, she elected to merely moan in a mixture of pain and delight. “Mah… my dick… it...hurts.” she eventually admitted.

Katie had her finger on the pulse, she knew what was up, the girl had become hard again, the position she was in was no longer feasible. “If I’ll release the shackles on your wrists, will you promise to be a good girl? Will you promise to do what I tell you?” she didn’t have to wait for a longform answer, the girl mostly wiggled in agreement. So she opened the girl’s shackles, pulled her away from the bed and instead pushed her forward where she fell to the ground, managing to catch herself with her hands in front of her. “GET ON YOUR KNEES!” Katie commanded “GET ON YOUR KNEES AND BEND OVER.”

“Yes miss!” Jessica submissively replied, making hate to get back on her knees and bending forward, placing her head on her hands near ground level.

“Good. Now beg. BEG for me to milk you dry.” the woman commanded.

“Please miss, please milk me! I’m so bad, please! Please do! Please miss!” the girl’s tone becoming more and more submissive and pitiful.

“You know I’ve never told you to call me miss, but I gotta say, I’m liking it.” the red haired woman moved over to the girl until she sat directly behind her. Her hands on the girl’s behind, her dick now visibly wiggling around. “On that note, I actually planned on just getting you hard again, so you could stick your cock in me. But I’m liking this too much. Wouldn’t have worked anyway eh? You’re such a mess!” she slapped the girl’s butt from behind, effectively spanking her again “You’re just too horny, aren’t you? You’ll see, I’ll make you a true degenerate yet!” 

“Yes. I’m so horny miss! Miss!” she was clearly talking to herself more so than to Katie by speaking like this, this perspective was clearly making her mind-blanking levels of horny. “Please miss! I’m so horny, I can’t take your teasing. PLEASE.” 

Just hearing her plead like that was too much, Katie couldn’t but massage herself, she tried to sit above one of the girl’s legs, grinding against it. “Just keep calling me ‘Miss’ you greedy slut!” she commanded a last time before going back in. Pushing the girl’s buttcheeks away and hungrily digging into the girl’s butthole. 

She stuck out her tongue, pushing it against the girl’s butt, spinning it around, flicking it up and down, left to right and back around. From the taint upwards all the way across the girl’s tight hole. Meanwhile, all the girl did, was weep. 

“Miss! Miss please! Miss. Miss. MISS!” she pleaded under her moans. She was getting so aroused by this treatment. 

Katie’s hands moved from the girl’s buttcheeks further inwards to her butthole, attempting to slightly pull it open instead. Anything to allow Katie to move her tongue in deeper. It wasn’t much, but any little bit helped. She pushed her face in as far as she could, trying to push her tongue forward like a dagger, smacking her lips and moaning hungrily. Hearing the girl’s moans become bassier, she released her grip, instead her right hand gripped the girl’s dick, jerking it back and forth.

“MISS please. MISS. Bad. I’m bad Miss. Ah yeah, yea…” the girl moaned louder, her voice cracking. “Hmmmmmmmmrrrr…” 

The last few stretches, she didn’t say anything. She didn’t even moan that loudly. She was just breathing quickly, exhaling through her nose, she had found her flow. 

Eventually she came under a similar type of breathing. No bassy moans, no yelling, no words, just heavy breathing. Pure bliss. 

Katie could feel the girl’s dick wiggling stronger than usually, getting slightly harder and eventually releasing a fairly good amount of the translucent liquid. Far more than Katie expected for the girl to still possess this late in the evening. Half wet from the girl’s juices, half sweaty, her hand moved behind her own legs. And under her own heavy breathing she masturbated.

“Thaaaaaaanks miss…” the girl let out in a mixture of sigh and exhausted happiness, before her knees gave in and she fell over forward. Her buttcheeks still in a reddish pink tone from the spanking she had received earlier. She was clearly a mess, but a sexy mess. 

Spreading the liquid between her legs, Katie continued rubbing and fingering herself, unable to let go of how much she just made the girl cum. The girl’s pleading voice still in her head, crying and begging for her attention. Her girly translucent juices still on her hands, mixing with her own wetness. The way laid there before. The way she was begging. Begging for her. Crying for a filling. Pleading. Like a melody of thought and motion. What a bad girl. What a damn fucking bad girl. “Damn you, you fucking sluuuuut. Just you wait, I’ll make you cum even harder in the future. I’ll make you beg so much!” “B.E.G. For. MEE.” And with that, so did Katie, her body vibrating, her fingers wettening further. A bright smile on her face as the waves of pleasure pulsed through her body. 

In the end they both laid there, laying on the ground next to each other. “Think we better sleep now, eh?” the woman said slowly, tiredly.

“Yes Miss, please sleepy now.” the girl quietly replied, half asleep already.

Katie got up, pulling the girl onto the bed and tugging her in. Then she laid down in bed next to her. The girl seemingly fell asleep immediately, but Katie laid awake for quite a bit longer. Reflecting on this crazy night, smiling at the girl now innocently sleeping next to her.