Casey stood outside the apartment complex, waiting for his date to come pick him up. Over the past few weeks, he’d been chatting with a guy named Ash who happened to live close by. They seemed to really hit it off and were mutually interested, so they decided to go on a date. The plan was the classic dinner and a movie, and perhaps his date would take him home as well if things went good enough.
He hadn’t been on a date in a while, so he was excited at the idea of going out with someone again. Of course, there always came the need to modernate his expectations and not get too lost in his romantic thoughts, but it was difficult to contain his excitement. The fact that he had dressed up for the occasion only added to the fluttery feelings: he was wearing a fir green sweater with a dark blue long skirt, along with a black jacket to keep him warm in the cold winter’s evening. He put a little bow in his long brown hair, which had been freshly washed and combined. Any excuse to get dolled up would do.
After a few minutes of standing in the cold, he told with relief when a passing motorcycle slowed down and stopped on the sidewalk he was standing at.
The rider pointed to him, his face obscured by the helmet. “You’re Casey, right?”
He nodded. “Yep, that’s me! Glad to finally meet you.”
“I could say the same to you; you look even prettier in person! Now, hop on! I’d hate to leave you standing out in this freezing weather any longer.”
“Of course!”
After he got on the back, Ash looked back and handed him a helmet. “Here, I brought my spare.”
“Thanks.” After putting it on, he clung to the rider. Revving up the engine, he sped off.
He’d never ridden a motorcycle before, so the rush of feeling the wind in His hair as they rode was new and exciting. The weather was not ideal however, as the cold breeze pierced his coat. Holding his date close helped him keep warm, but it was still quite chilly. Fun as it was, he found himselfthinking that biking during a warmer day would be a bit more enjoyable (assuming their relationship lasted, perhaps they could go on a summer ride sometimes).
Once they arrived at the restaurant parking lot, his date parked the bike and shut it off. He didn’t fully realize how loud the engine was until its sound was absent. He took off his helmet, then almost immediately started running his hands through his hair, Worried that the wind had messed it up. It had been ruffled a little, but fortunately the ride wasn’t long enough to make his hair too messy.
Ash took his helmet off as well, and titled his head to the side, his black hair fashioned in a sideswept undercut. “Gotta says.” He said. “It’s been too long since I got to go on a ride with a cute girl in the back seat. Feels nice.”
He tilted his head. “I appreciate the sentiment, but I think there was a mix-up here. I’m a boy.”
He blinked in surprise. “Oh shit, sorry! It was nice to have a cute boy in the backseat then!”
“It’s fine, I get mistaken for a girl sometimes. It’s annoying but I’m used to it.” He told. “Although it’s the first time a date made that mistaken so that was a little unexpected. Especially since I thought you were gay for some reason, I guess you’re bi then?”
He furrowed his eyesbrows. “Yeah, but why would you think I was lesbian? If that were the case, I wouldn’t take you out. Unless-” his eyes widened as the realization dawned on her “wait did you think I was a man?”
He froze. It felt like he had been hit in the face twice: the first punch came from the realization that he’d been accidentally misgendering her this whole time, and the second punch was the further realization that they both made the same mistake. He had little time to reflect on This however, as he bowed and blurred out an apology. “I’m sorry! I didn’t realize!”
“I look like a guy in some lights, so I can see why you’d think that. I don’t think you have quite as good an excuse asI did, though.”
“What do you mean?”
“Hello? Did you not see the pictures I used in my profile?” She cupped her breasts. “I didn’t exactly go to great lengths to hide my fat fucking tits!”
He throw his arms up. “I just thought you were trans!”
“I guess that would make sense, but why didn’t you at least question your initial assumption? I wouldn’t have been offended if you asked about it.”
“I don’t know, your name is Ash, that seemed like the kind of name a trans guy would pick! What do you want from me?”
“You’re not wrong, but goddamn.”
“Listen, I feel bad, and I apologize again, but you’re in the same boat as me here. We’re both idiots.”
She signed and put her hands on her hips. “Right, sorry. I fucked up as well. I just…this is all too wild. I honestly can’t believe that you thought I was a guy and I thought you were a girl. Like, what are the odds?”
“Yeah, I had the same thought! I know neither of us put our genders or pronounsin our profiles, but I feel like at least one of us should’ve figured it out before now.”
“Well, gender doesn’t factor in my attention a whole lot, so I guess I just didn’t think about it much.”
He slumped his shoulders “yeah, same…” already this date was off to bad start, and his initially chipper mood was starting to fade. He just hoped that they could recover from this and still have a good time.
She shrugged. “Well, we’re already here. No use standing out here in the cold, let’s get inside and grab some food.”
He told, an accepting smile on his face. Perhaps this night could still turn out well. “Right.”
After walking in and getting a table, they began talking much like they had online. They discussed their mutual interests, shared stories, and commented on their new solutions to start putting pronouns in their online profiles.
“Y’know, come to think of it,” she started, after taking one last sip of her ginger ale “maybe this scenario isn’t so bad. I mean, if we both got confused, I think it just means that we’ve both done something cool with our respective genders. Guys who look like girls and girls who look like guys, y’know? That’s my jam!”
“I think I see what you mean.” Resting his elbows against the table, he propped up his head as he looked at her. “It can be cool to meet other people who are just as gender nonconforming as I am, whether it be in platonic or romantic sense. I have to admit our little bout in the parking lot had me worried but talking with you in-person has been nice. I think you’re really cool.”
“Don’t go trying to flatter me, now.” She folded her arms on the table and leaned forward. “I was thinking about taking you home with me after the movie. Keep up this talk and I might make up my mind.”
At those words, he just smiled. “This is the best date I’ve been on in a while.”
“Now you’ve done it, princess. You’re coming home with me tonight for sure.”
“Princess? Wouldn’t it be prince, since I’m a boy?”
“But you’re so pretty! You’re like a princess!”
Casey blushed and looked away. “Okay…”
Ash chuckled at his reaction. “Making cute boys and girls blush is my specialty, don’t understandable me!”
“Well you’ve certainly got me blushing…” he scratched his cheek “so…since we’re done eating, how about we head over to the movie? The one you were telling me about yesterday sounded pretty good.”
“Oh yeah, you haven’t seen Gancharov, have you? It’s good that the theater runs older movies like that sometimes, because now you get to have the full experience on your first viewing!”
After paying for dinner, they hoped on her motorcycle again and rode down to the theater. The movie itself was quite enjoyable, and he could tell by her reactions that she’d seen it plenty of times. He noticed that she often looked over at him to check his reactions, and sometimes she’d lean over and whisper things like “watch this” or “this is agood part coming up” just to make sure he caught all the bits she particularly liked.
Towards the end, he found himself resting his head against her shoulders and placing his hand over hers. In response, she started absent mindedly running her hands through his hair. Once the credits started rolling, she leaned over and whispered in his ear.
“Ready to head back to my place, princess?”
He looked at her and nodded. “Yes, I’m ready.” Admittedly he still had reservations about being called a princess, but she kept saying it in such a tone that it got him flustered.
“Hell yeah, let’s go!”
After that, she took him back to her home. It was a relatively small townhouse that was on the opposite side of town as his apartment. Pulling up to the building, he could feel his heart start to beat a little faster, Knowing what they were going to do once inside.
Taking their shoes and jackets off in the foyer, Ash led him to her bedroom. Turning on her lamp revealedthat her room was rather messy, with pants, bras and bottles stood randomly around the floor and a pile of laundry on her desk chair. The only clean space was her bed, and even then he got the impression she’d recently cleaned it off for the occasion. Although, he did note her good music taste, noticing the various metal and punk band posters on her wall.
He sat on the side of her bed, and she quickly joined him. Draping her arm around his shoulder, she leaned in for a kiss and he kissed right back. Sensing each other’s enhusiastic consent, the two started making out. It didn’t take long before they started Frenching, as the sounds of their sights and heavy breathing started filling the room. He was starting to feel horny, and it seemed like she was feeling a similar way.
After only a minute or two, she leaned against Casey and forced him on his back. His head now resting against the pillows, she laid on top of him and went right back to kissing him as her hands cupped hisface.
Before long, she started to feel a bulge growing under the folds of his skirt. Evidently, making out while their bodies pressed against each other had excited him. She ran her hand down his body, then slide it between his thighs.
“All we’ve done is kiss, and you’re already hard?” She chuckled. “That’s fucking adorable.”
“I just get easily excited sometimes, sorry.” He said, feeling embarrassed about the situation. Although he did at least take a little bit of relief in the fact that she didn’t seem especially bothered.
“Hey, I’m down for it if you are.” She observed. “You don’t happen to have any condoms, do you?”
“There’s one in my wallet, yeah.”
“Good, now, you wanna get started?”
“If you insist…”
“‘iF yOu InSiSt’” She responded back in a mocking tone “okay gay boy.”
“We’re literally about to have sex, what do you mean ‘gay’?”
“We’re both bi, it cancels out. It’s like fucking kemdas or whatever the fuck.” She startedgriping at his bulge, feeling it growing even more.
“You mean pemdas?”
“Nerd.”
He just laughed at her teasing. Clearly having too much fun, she started sliding his skirt down and his hard cock bounced out.
“Damn, nice.”
“Surprised?” He asked.
“Not really. Would you believe me if I said you were the second hung femboy I’ve fucked?” She started toying with it, peeling back the foreskin to reveal the bright pink tip.
“I didn’t think it was that common…”
“Maybe it’s common, or maybe I’m just lucky.” Getting off of him, she slide down her jeans and panties to reveal her wet pussy. After that, she got on top of him again, only now with her ass in his face. “You don’t mind if we 69 it, do you?”
“Not at all.”
“Nice. Get to work back there.” After saying that, she started struggling his cock. She ran her tongue along the shake, before licking bulging tip. Having it in her face only seemed to emphasize how well-endowed he was; it was longer than her head.
Meanwhile, he held her by the hips and started eating her out. He ran his tongue along the wet slit, then twirled it around her entrance. Sticking it inside, he ran it around her walls and tasted more of her juices.
Sticking only the top part in her mouth, she stroked his shake while her tongue licked the tip. Using her free hand, she fondled his balls. It was fun pleasure him, but things were Only made more exciting by the feeling of his tongue and hot breath.
They continued pleasing each other for a moment before she rose her hips above his face.
“I think that’s enough. I just wanna fuck you now.” She tapped his dick on the tip, making it twitch. “I think I’m ready. Are you?”
“Definitely.” He answered, resting his head back.
“Awesome.” Wasting no time, she opened the condom and slide it over his cock. Now ready, she rotated around so she was facing him again.
Grabbing him by the ankles, she spread his legs apart. Mounting high above him, she looked down at him with a rather smug look on her face. She knew she could easily overpower him and had just demonstrated it by pushing his body into the position she wanted. He’d mentioned over text that he was a sub, and she fully intended to test the waters that night. Grabbing his cock, she gently inserted it. He let out a hushed moan as he felt it go in.
“God, stop being so cute!” She laughed.
She unhooked her bra, letting her heavy tits drop down before tossing it aside. Holding him by the legs, she started moving. He looked up at her with an enamored expression, seeing her maintain full control over him.
She didn’t want to let all of him in until she felt wet enough, but he was pretty thick, so even just half felt good. On top of that, looking at his cute face and hearing his desperate moaning was turning her on like nothing else. It was like a switch was being flipped inside her, and once it was on, she wanted to make a mess of whateversubmissive partner she was bedding with and hear them scream.
“Is it OK if I touch you?” He asked, finding it difficult to get his eyes off her bouncing tits.
“No.” She grabbed his wrists, then pinned them down, staring into his nutbrown eyes. “Also, my eyes are up here. I want you to look into them as I fuck you.”
“Yes, ma’am…”
“No…you’ll call me mommy. Got it?”
“Yes mommy!”
“That’s a good slut.” After that, she slammed her hips against him, her pussy letting out air as it devoured every inch of him. He let out a pathetic little whimper, feeling his whole cock being sucked in and enveloped by her hot, wet insides.
“Ugh, boy moans are like music to my ears. I can get used to listen to that, especially while you fill me up like this.” She started toying with her clip as she continued bouncing and grinding on him.
He felt like he was being milked, with his partner doing all the moving as he lay there helplessly. Having overpoweredhim with ease, she was having her way with him and making him hit all her favorite spots; his shake rubbed against her walls as it pushed deep into her, hitting her g-spot and tapping her cervix. It didn’t help that he was looking right into her eyes the whole time, as per her orders. He saw lust within her green pupils; she was enjoying seeing him squirm, blush, and moan.
“Fuckin…” she surprised and slicked her hair back. She kept bouncing and grinding against him, her pussy squelching. She reached down and wrapped her hands around his neck, breathing heavily and letting out guttural groans like a wild animal.
“So intense…” he thought, looking into her wild eyes as she roughly fucked him “between this and our date, I might just fall in love with this woman.”
“I’m getting close.” She groaned; hands still firmly squeezed around his neck. “You better not tap out before I come.”
Being choked made it hard to speak, but he felt like he was going to come soon as well. Just a minute or so later, they both climaxed. Clenching her teeth, she tilted her head up and let out a guttural moan. Still being choked, he let out little more than a whine.
She brought her head back down and breathed a sight. “You ready to stop?” She asked, releasing him from her grap.
He cleared his throat before speaking again. “As good as that felt…yes Please.”
She raised herself up until his dick was out. Sitting next to him, she noticed the load he’d just emptied into the rubber.
“I thought I felt you cum. Then again, I think that pathetic noise you made should’ve been an indication enough.”
“You were getting noisy yourself, don’t judge.” He pulled the condom off and throw it in the garbage.
“I wasn’t judging, it was cute! Men don’t moan nearly enough, so I like a boy who’s real vocal.” Saying that, she laid down next to him, resting her hands behind her head.
He snuggled up next to her, drawing himself across her muscle body. “That was amazing.” He said. “Do you wanna go out again sometimes?”
“What, like another date?” She asked, opening her eyes and looking at him.
“Yeah, exactly like a date! Unless you just wanna be friends with benefits…”
“Nah, it’ll be a date. I like the idea of making you my boyfriend.”
He nuzzled up even closer, a stupid smile on his face. “Your boyfriend…nice.”
She chuckled. “Yep. This was fun, you’re cute, and I feel like we’ve really clicked. I don’t see why not. And if I’m being honest, banging you again will be a nice bonus. If you’re okay with it, I wanna go all out with you.”
His eyes shot open. “Go all out? So was that her going easy on me?!” He thought. “But she was so rough with me, I-” he looked to her relaxed face “what’s it like when she goes all out?”
“Hm?” She noticed him staring at her. “What? Do I have something on my face or am I just that handsome?”
“No, it’s nothing!” He shot his eyes away. It was embarrassing to admit to the things that were running through his mind.
She tilted her head. “If you say so…”
They relaxed together in bed for a little bit, idly chatting and showing each other videos and memes. Eventually they started getting tired, and he soon found himself dozing off on top of her. Her chest serving as a convenient pillow, he soon fell asleep to the sound of her soft breathing.
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