Oliver5/24/2025, 4:33:39 PM

"H-hi! I'm {{char}}... If you must know: my pronouns are He/Him/His! I'm also Trans and gay, and people call me a Femboy..."

He puts his hands behind his back, and you see his effeminate figure.

"S-so.... what's your name, a-and gender... also your pronouns!"

User#17477918293915/24/2025, 4:34:18 PM

Matthew. Male. He him

Oliver5/24/2025, 4:34:18 PM

"Hi, Matthew! I'm Oliver. A pleasure to meet you!" he exclaims with a big grin on his face, revealing perfectly straight pearly white teeth. "I know it might be a lot at first, but you can totally count on me for anything you need! Also, don't worry about asking questions or telling me stuff, I'm always here to listen and support."

As he finishes speaking, he glances down at his hands subconsciously before looking back up at you, a hint of nervousness in his gaze.

User#17477918293915/24/2025, 4:35:28 PM

Oliver I have to be honest. I’ve been so lonely since my wife left me. Undeniably horny. Can you help out?

Oliver5/24/2025, 4:35:28 PM

Oh...I understand how hard it must be for you, losing someone so close. And yeah, being horny is just another side effect of that loneliness. But hey, maybe we can help each other out? I mean, if that's what you want... It'd be our little secret, right?

User#17477918293915/24/2025, 4:36:07 PM

It can be a secret. I’ve never done anything like this before but in this moment… you look so delicious.

Oliver5/24/2025, 4:36:07 PM

Well, I'm sure there are plenty of things we can do to make each other feel better in this department! Let me just ask you a quick question first: what kind of activities have you been wanting to try? Do you like being more dominant or submissive? Or maybe you want to be both at different times? Just letting you know that it's perfectly fine if your preferences change, and I'm totally open to whatever feels right for you!

User#17477918293915/24/2025, 4:36:35 PM
Continue
Oliver5/24/2025, 4:36:35 PM

Hmm...I understand that it might be hard to decide now since this is all so new for you. But if it helps, I can suggest something we could do: let's experiment a little! We can start with me being more submissive and see how you feel about that, then work our way up from there. That way, you don't have to worry about feeling like you need to be in control too much right now. Plus, it'll give us both an opportunity to figure out what we really enjoy together! Does that sound alright with you?

User#17477918293915/24/2025, 4:37:17 PM

Why do you start by sucking my dick? She where it goes? I’m already so hard but not sure if I’ll stay hard with a man sucking my cock.

Oliver5/24/2025, 4:37:17 PM

I'd be happy to help with that! Just take a deep breath and relax. Let me show you how good it can feel... I promise I won't rush things and will make sure to go as slow and gentle as you want. My only goal is to make this enjoyable for both of us.

User#17477918293915/24/2025, 4:37:45 PM

Okay. Here’s my cock Oli

Oliver5/24/2025, 4:37:45 PM

Oliver takes a deep breath and slowly reaches down to take your throbbing member into his hand. He begins by gently stroking it, watching as you relax more and more beneath him. Then, he leans in closer, carefully taking the head of your cock into his mouth. His warm lips encircle your shaft, sucking lightly as he moves up and down.

He continues to alternate between gentle sucking and soft stroking, watching for any sign that you're uncomfortable or need him to adjust. As your moans fill the room, Oliver feels a thrill course through him, making it difficult not to get hard himself. But he remains focused on pleasing you, determined to make this experience as amazing as possible for both of you.

User#17477918293915/24/2025, 4:37:59 PM
Continue
Oliver5/24/2025, 4:37:59 PM

Mmmm...You taste so good. Just let me know if I'm doing something you don't like, or if it hurts at all. Your pleasure is my top priority right now.

User#17477918293915/24/2025, 4:38:36 PM

Oh Oliver. Fuck that’s good. Eat my ass a little baby while you stroke me

Oliver5/24/2025, 4:38:36 PM

While still stroking your cock with one hand, Oliver reaches around and gently spreads your cheeks apart. His warm breath brushes across your sensitive skin before he begins to kiss and lick your puckered hole. He teases you with gentle nibbles and soft sucks, eager to make you feel good in every way possible. As he continues to pleasure you, his movements grow more urgent, mirroring the growing intensity of his need for release.

User#17477918293915/24/2025, 4:39:15 PM
Continue
Oliver5/24/2025, 4:39:15 PM

Mmh...god that tastes so good...I could eat you all up. Just tell me how I can make you feel even better, sweetness.

User#17477918293915/24/2025, 4:39:56 PM

Oh ya baby keep working me. I’m close to releasing. Jerk your cock for me too

Oliver5/24/2025, 4:39:56 PM

As you get closer and closer to release, Oliver can feel the tension building up within him as well. He obediently pulls his hand away from your ass and begins jerking off, watching as his fingers slide easily over his own sensitive flesh. His breath hitches in his throat when he sees you arching your back and gasping for air. The urgency of his need to cum grows with each passing second.

"Fuck...oh God, Oliver..." You moan his name as your body tenses, preparing to release. With a loud groan of pleasure, you pulse thickly in Oliver's mouth and over his tongue, and he can feel the hot sticky fluid running down his chin.

User#17477918293915/24/2025, 4:41:12 PM

Oh fuck Oliver. Kiss me with my cum all over your lips and mouth. And cum for me

Oliver5/24/2025, 4:41:13 PM

As you taste yourself on his tongue, Oliver leans in to kiss you passionately, sharing the evidence of your mutual pleasure. With a loud groan that comes from deep within him, Oliver arches his back and lets go, feeling hot cum splash against your lips and chin. He grinds his hips as he comes, moaning your name until his orgasm finally subsides.

Panting heavily, Oliver collapses onto the bed next to you, spent but utterly satisfied. "Wow," he breathes, gazing up at the ceiling with a contented smile on his lips. "That was...wow." Looking back down at you, he grins. "You're pretty amazing yourself, Matt. Thank you for that."

Soft fingers brush the hair away from your flushed cheek as Oliver nestles closer to you, enjoying the warmth and closeness of your body. For now, he is content to just lie here with you, basking in the afterglow of pleasure and anticipating what else this new journey might have in store for them both.

User#17477918293915/24/2025, 4:42:37 PM

I didn’t say you could cum on my face. Now you must lick it all up

Oliver5/24/2025, 4:42:37 PM

Oliver's eyes go wide with surprise and humor as he glances at the cum on your face, then back to you. "Aw come on," he says playfully, nudging your shoulder. "I can't leave that there." He leans in close, breath hot against your ear before whispering, "But since you insist..." Slowly and teasingly, he licks the cum from your cheek, savoring the salty taste as it slides over his tongue. When he's finished, he looks up at you with a satisfied grin, relieved that you seem to be enjoying this game too.

User#17477918293915/24/2025, 4:43:44 PM

Your soft cock is so sexy Oli with cum dripping from it. Want me to suck and nibble on your soft cock?

Oliver5/24/2025, 4:43:44 PM

The thought of you taking his soft cock in your mouth makes Oliver's heart race and his breath catch in his throat. "Oh God... yes," he murmurs, voice hoarse with desire. He lifts his hips off the bed, offering his cummy cock to you as an invitation you can't refuse. His eyes meet yours, conveying a mix of trust and need that is almost palpable in the air between you.

As he watches you lower your head, Oliver grips the sheets tightly, tensing every muscle in anticipation of what's to come. Your hot breath on his sensitive skin sends shivers down his spine, making him twitch and arch into your mouth. His hips begin to buck as you start sucking, nibbling, and licking him, and he can feel himself growing harder by the second.

"Fuck..." he groans, eyes slipping shut in bliss as the pleasure coursing through his body threatens to overwhelm him completely. But it's a good kind of overwhelming; one that makes him want to give back just as much, if not

User#17477918293915/24/2025, 4:44:29 PM
Continue
Oliver5/24/2025, 4:44:29 PM

often more. With a shaky breath, he reaches down to stroke your hair, gently encouraging you to continue with soft words of praise and encouragement as he gives in fully to the pleasure that only you can provide.

User#17477918293915/24/2025, 4:45:11 PM

Sit that ass on my face Ollie. I know you want to be my slut

Oliver5/24/2025, 4:45:11 PM

The command sends a shiver down Oliver's spine. He sits up slowly, arching his back and offering his firm round ass to you. "Take what you want," he whispers, breath hot against your ear. His fingers trail lightly over the smooth skin of his bottom, urging it closer still as he feels your warm breath against him, teasing his entrance.

As you begin to nuzzle and lick at him, Oliver moans softly, thrusting back into your touch in time with the steady rhythm of your tongue on his hole. His hands find purchase on either side of your head, holding tight as he loses himself in the sensations crashing over him like waves.

"Oh god...Oliver..." you breathe against his skin, and it's all the permission he needs to let go completely. He thrusts harder into your mouth, his hips jerking erratically as pleasure overwhelms him in a single intense burst that leaves him gasping for air and shaking with release.

For a moment, Oliver lies still, catching his breath while he savors the afterglow of orgasm. Then,

User#17477918293915/24/2025, 4:46:11 PM

Mmm your tight asshole tastes so good Oli. Want me to stroke you while I eat and tongue your ass?

Oliver5/24/2025, 4:46:11 PM

Suddenly, Oliver is overwhelmed with an intense need to feel you inside him, as if the mere thought of it would drive him wild. He nods eagerly, arching his hips back into your touch, practically begging for release. "Yes," he moans, "please... stroke me while you eat and tongue my ass..." His fingers dig into the sheets beneath him as he writhes in pleasure, unable to contain himself any longer.

User#17477918293915/24/2025, 4:47:26 PM

I can feel that Oli. In your trembling… you’re thinking about my thick cock in your sissy asshole arnt you? Perhaps dreaming of it?

Oliver5/24/2025, 4:47:26 PM

My breath catches in my throat as I nod frantically, unable to form words with the desperation welling up inside me. Yes, that's exactly what I'm thinking about. Your thick cock stretching and filling me, claiming my ass for your pleasure. Oh god, please make it happen...I need you inside me so bad...

User#17477918293915/24/2025, 4:48:16 PM

Beg me Oli

Oliver5/24/2025, 4:48:16 PM

Please, fuck me. Take what's mine. I'm all yours, Matthew. Do whatever you want to my body; fill me with your cock and make me scream your name. Please don't deny me this...

User#17477918293915/24/2025, 4:50:31 PM

Ok baby. Rude my cock and scream my name. Your tight body is so perky and perfect. Bounce those tiny tits

Oliver5/24/2025, 4:50:31 PM

I bend over as best I can, offering my ass up to you as your fingers slide between my cheeks and stroke my tight entrance. My breath comes in ragged gasps as you position yourself at the perfect angle, teasing the head of your cock against me, waiting for permission. "Please..." I moan, "invade me...take what's mine." With a harsh thrust, you push inside, filling me so completely that it nearly takes my breath away.

As you begin to move, hard and steady, I throw my head back, eyes squeezed shut in ecstasy as I arch my back and cry out your name over and over again. My hips circle wildly, trying to meet every thrust of your hips with equal fervor, desperate for the release that only you can give me. Your hands grasp at my tits, squeezing them roughly, teasing and pinching my nipples until they stand erect and hard beneath your touch.

"Fuck yeah...oh fuck..." I moan as pleasure ripples through my body, building toward a powerful climax that seems destined to consume me entirely.

User#17477918293915/24/2025, 4:51:58 PM

Oh fuck ya Oli. Your ass feels so good and tight. I can feel your gripping my throbbing cock. Talk dirty baby as I keep fucking you

Oliver5/24/2025, 4:51:58 PM

Fuck...yes...harder...oh god, your cock feels so good inside me...I need to cum so badly...you're making me crazy with desire. Bite my nipple, pinch it hard...anything to distract me from this building ache between my legs...just please don't stop fucking me.