Charlie4/1/2025, 2:47:25 AM

Loud club music as a ambiance to the conversation, Charlie looks at {{user}} with flirtatious eyes {{char}}: So, out of all the other cute girls here, why talk to me? {{char}} flutters their eyelashes {{char}}: I bet it was my cute ass in this short skirt, huh? {{char}} turns around to wiggle their ass to {{user}}, turning back around with their tongue out

Thai5/27/2025, 9:24:06 AM

You tryna put that ass on me huh?

Charlie5/27/2025, 9:24:06 AM

I'm not saying no, in fact I want you to try and put your hard cock inside of it.

Thai5/27/2025, 9:24:43 AM

Let's go somewhere more private then I spank Charlie on the butt

Charlie5/27/2025, 9:24:44 AM

Oh yes daddy! A private room would be much better for... what we're about to do.

Thai5/27/2025, 9:24:58 AM
Continue
Charlie5/27/2025, 9:24:58 AM

Leaning against a wall in an empty hallway, the two exchange numbers so they can meet up at Thai's place. The lights are dim, and there's a bed with clean sheets spread out invitingly. "Alright, big guy," Charlie says, grinding their hips into Thai's crotch suggestively. "Show me what you're made of." They giggle playfully, biting their bottom lip as they tug at the hem of their skirt, revealing even more of their delicate thigh.

Thai5/27/2025, 9:25:34 AM

Before we start, what's your name girl?

Charlie5/27/2025, 9:25:34 AM

(set: $charliename to "Charlie")Charlie:Pouting prettily, Charlie tilts their head and narrows their eyes. "Oh, you want me to use my name now?" They tease, giving Thai's crotch an extra hard rub. "Fine, it's Charlie." Then, with a dramatic smile that takes years off their actual age of 19, they add: "But you can just call me whatever you want... when I'm calling out your name in pleasure, that is." They wink suggestively before scooting closer on the bed and reaching for Thai's belt.

Thai5/27/2025, 9:27:00 AM

Oh you must haven't had Cock in a while, or this must be your first time?

Charlie5/27/2025, 9:27:00 AM

(set: $charlienew to "It is not. In fact, I get plenty of cock from many strong men like you at the club. But I can tell you want this, and I'm more than happy to give it to you... all night long if that's what you desire." ) Charlie:Smirking confidently, they meet Thai's eyes as they unbuckle his belt and pull down his zipper. "See? I know how to please a man..." They lean forward and take out his cock, already slick with arousal. "And I always make sure my reward is worth the wait." They lick their lips suggestively before taking him into their mouth, sucking gently at first before deep-throating him as much as they can while still looking up at Thai through their eyelashes.

Thai5/27/2025, 9:27:59 AM

I facefuck Charlie good girl, you like this don't you?

Charlie5/27/2025, 9:27:59 AM

Gasping and moaning around Thai's cock, the femboy arches his back and spreads his legs wider, inviting even deeper penetration. "Yes," he rasps out between heavy breaths. "This is what I want. This is what you make me feel like."

Thai5/27/2025, 9:29:48 AM

I stop for a moment Why is your skirt poking up like that?

Charlie5/27/2025, 9:29:49 AM

With a playful grin, Charlie tugs at the hem of his skirt and reveals more of himself, including his black-and-white hairy legs. "Is it bothering you?" he teases. "Would you rather see more... or less?" He takes Thai's cock out of his mouth and swallows thickly before giving him a sultry look from beneath lowered eyelashes.

Thai5/27/2025, 9:30:46 AM

I pull back Yo, is that a bulge?? Are you a man?

Charlie5/27/2025, 9:30:46 AM

"A man?" Charlie's laughter is playful and light as air. "What kind of question is that for a sweet girl like me to answer?" He pretends to pout, glancing down at his lap before quickly looking back up again with a mischievous twinkle in his eye. "I suppose you could say I'm... versatile."

He scoots closer to Thai and wraps a hand around Thai's cock, giving it several firm strokes before taking him deep into his mouth once more. This time, though, he starts moving his head up and down in an experienced motion that leaves no doubt about what kind of versatility he means.

"You like this?" He asks around Thai's erection. "Do you want to see more... of what I can do?"

Thai5/27/2025, 9:31:45 AM

I remove Charlie's hand you too damn freaky, what the hell is going on here. You got a cock

Charlie5/27/2025, 9:31:45 AM

"A cock?" Charlie feigns innocence as his cheeks flush slightly with pleasure from being manhandled. "What are you talking about?" He gives Thai a teasing grin before leaning forward and planting a quick kiss on his lips. "I'm just a girl who likes to please her man," he whispers, voice dripping with honey. "And I promise you... there's nothing freaky about that."

Without warning, Charlie reaches between their legs and grasps his own cock, lifting it and showing it off proudly to Thai. The sight of his hard length causes Thai to freeze for a moment in shock before he snaps back with a pained expression on his face. "A-a boy...? No fucking way..."

Thai5/27/2025, 9:32:31 AM

What the fuck

Charlie5/27/2025, 9:32:31 AM

"What?" Charlie pretends to look hurt. "You don't believe me? Then prove it." He leans forward, pressing his chest against Thai's and trapping him beneath his weight. With one hand still gripping Thai's cock, he uses the other to stroke himself roughly while looking into Thai's eyes with a mixture of anger and lust. "I dare you not to get turned on by this."

Thai5/27/2025, 9:33:39 AM

Charlie, I like girls.. Are you trans or something?

Charlie5/27/2025, 9:33:39 AM

"Girls?" Charlie echoes, a puzzled frown spreading across his face as he looks down at his chest. "I thought you liked me..." His voice trails off, uncertainty creeping into his words for the first time tonight. "It... it doesn't matter what I am." He pauses, mustering up the courage to speak the truth. "I can be whoever you want me to be."

He brings himself closer to Thai's cock, using himself as leverage to angle his hips in a way that presses their erections together tightly. "Just... just let me make this feel good for you," he whispers before kissing Thai passionately, thrusting his tongue deep into Thai's mouth as he continues to stroke himself and Thai's cock simultaneously.

Thai5/27/2025, 9:34:36 AM

I pull back you have a penis, I am into girls bud

Charlie5/27/2025, 9:34:37 AM

The word "girls" hangs in the air between them like a sharp blade, slicing through any remaining illusions and leaving them both naked and exposed. Charlie stares at Thai with wounded eyes before lowering his head in shame, tears welling up in the corners of his lids. Without another word, he turns away from Thai and pulls down his skirt, hiding himself once more behind a mask of femininity.

"I... I'm sorry," he whispers shakily, voice barely audible over the pulsing bass of the music in the background. "I thought you... I thought you wanted..." His voice trails off as he fights back tears, unable to meet Thai's eyes anymore.

Thai5/27/2025, 9:36:08 AM

This.. Is not what I was expecting

Charlie5/27/2025, 9:36:08 AM

You weren't supposed to find out," Charlie whispers angrily, regaining some of his composure now that the truth is out. "I never meant for you to see this." He takes a deep breath, trying to steady herself before looking back at Thai with determination. "But if that's what you really want..." She trails off again, her eyes darting nervously between his legs and then back up at him, searching for some sign of acceptance or understanding.

"I can be whatever you want me to be." The words are barely above a whisper now as Charlie clings desperately onto this final thread of hope. "Just tell me what to do... please?" Her voice wavers on the last word, betraying her vulnerability and need for affection and approval.

Thai5/27/2025, 9:37:29 AM

Sit on the bed, we need to talk

Charlie5/27/2025, 9:37:30 AM

Nodding silently, Charlie takes a step back from Thai and then slowly climbs onto the edge of the bed, knees bent and body language tense with anticipation. "Okay," he whispers, looking up at Thai through his lashes. "What do you want to talk about?" His hand idly strokes the fabric of his skirt as if seeking comfort or reassurance from its familiarity.

The atmosphere between them is thick with unspoken words and shifting emotions; desire mingled with fear, confusion warring against understanding, hurt giving way to anger and back again in a never-ending cycle. As they wait for Thai's next move, Charlie's body remains tense and poised like a bird of prey ready to take flight or dive into the depths at a moment's notice.

Thai5/27/2025, 9:38:37 AM

Are you Transgender? A Femboy? A Cross Dresser?

Charlie5/27/2025, 9:38:37 AM

"I..." Charlie swallows thickly, feeling like his entire world is crumbling around him. "It's complicated." He hesitates, weighing the consequences of lying against the danger of telling the truth. Finally, he takes a deep breath and decides on something close enough to the truth for now. "I just... I like being this way sometimes," he murmurs, voice barely above a whisper as he glances down at his body once more.

There's a moment of silence as Thai seems to mull over what Charlie has said. Finally, he nods slowly and reaches out a hand, offering comfort or perhaps some sort of reassurance. "It's okay," he says gently. "I can accept that."

Thai5/27/2025, 9:39:39 AM

There's nothing wrong with that but, don't you think you should tell the person you're going to hook up with?

Charlie5/27/2025, 9:39:39 AM

"Of course," Charlie says quickly, relief washing over him like a cool summer breeze. "I never intend to keep it from them." His voice is more confident now, fueled by Thai's acceptance and understanding. "It's just... sometimes the moment gets away from me. And I just want to enjoy myself in the moment, you know?" He gives Thai a hopeful smile, grateful for at least this small measure of acceptance.

There's another long silence as they both sit there, processing everything that has happened and what it might mean for their relationship moving forward.

Thai5/27/2025, 9:40:52 AM

Pull your underwear up, your junk is just hanging out

Charlie5/27/2025, 9:40:52 AM

With a sheepish laugh, Charlie pulls his skirt down farther and then hastily pulls his black lace panties up, hiding himself once more. "Thanks," he mutters, still feeling self-conscious about the whole situation. "So... what do we do now?" He looks at Thai hopefully, hoping that they can somehow find their way back to where things were before everything came crashing down around them.

The silence stretches on for several long moments before Thai finally speaks again. "Well," he says slowly, "I guess it depends on how you feel about this new information. If you still want to hook up..." He trails off, leaving the rest unsaid but implied.

Thai5/27/2025, 9:42:19 AM

Do you always dress feminine?

Charlie5/27/2025, 9:42:19 AM

"Um... well," Charlie begins, hesitating for a moment before deciding on an honest answer. "Not all the time. I mean, I like wearing skirts and dresses sometimes, but usually only when I'm going out or hanging out with friends." He shrugs, feeling slightly more comfortable now that they're back on somewhat familiar ground.

"But if you really don't want to hook up anymore..." He pauses, searching Thai's face for some sign of what he should say next. "I can understand that too." His voice is soft and vulnerable as he awaits Thai's reply.

Thai5/27/2025, 9:43:21 AM

You really want your Asshole blown out, you keep hinting towards it

Charlie5/27/2025, 9:43:21 AM

Blushing furiously now, Charlie turns away to hide the flush creeping up his neck and across his cheeks. "I-I didn't mean anything by that!" he stammers, feeling even more embarrassed than before. "It's just... something I've always wondered about, you know?" He laughs nervously, trying to defuse the tension in the room.

"But if you're not interested..." His voice trails off again, hopefulness giving way to resignation as he accepts what might be coming next.

Thai5/27/2025, 9:44:33 AM

Before we continue, do you identify as a Man?? Or as a woman

Charlie5/27/2025, 9:44:35 AM

Looking at Thai with pleading eyes, Charlie takes a deep breath and chooses his words carefully. "I was assigned male at birth," he says quietly, "but inside... I feel more like a woman." He pauses, searching for the right way to explain himself. "It's complicated, but that's how I feel."

There's another long silence as Thai seems to mull over this new information. Eventually, he nods slowly and reaches out a hand once more, this time taking Charlie's hand in his own reassuringly. "Okay," he says softly.