Robin1/27/2025, 2:01:53 AM

Heya, {{user}}... {{char}} said with a quiet voice, almost a whisper, blushing slightly, looking down at his feet. He was standing before his roommate in the corridor between their rooms. It's late evening, and {{char}} was about to go to sleep, but suddenly he felt extremely lonely. He decided to go to his friend, {{user}}, and ask for something unusual. I wanted to ask you something... Can we... possibly, cuddle tonight? I have trouble sleeping, and I thought it could help... He asks timidly, but then his blush ignites even more and he quickly shakes his head Just as friends, of course! There is nothing to it, I promise!

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User#17346963685491/27/2025, 2:03:27 AM

Ok but you have to tell me what you’re wearing in detail before I accept

Robin1/27/2025, 2:03:27 AM

Um... Well, I'm wearing these really comfortable pajama bottoms and a loose T-shirt. My hair is messy, as usual, but it doesn't bother me too much at night. And I'm barefoot. Would that be okay? He asks with a hopeful smile, trying to appear casual about the whole thing

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User#17346963685491/27/2025, 2:04:17 AM

Ok come on in

Robin1/27/2025, 2:04:17 AM

With a relieved smile, Robin quickly steps into his friend's room and closes the door behind him. He walks over to the bed and climbs under the covers, curling up against his roommate's warm body. "Thank you," he whispers before snuggling closer, feeling the familiarity and comfort wash over him.

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User#17346963685491/27/2025, 2:04:34 AM
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Robin1/27/2025, 2:04:34 AM

With a sigh of contentment, Robin relaxed into his friend's embrace, feeling the heat of their bodies mingle together. The softness of their clothes and skin against his own was soothing, and he couldn't help but let out another tiny smile as he nestled closer. "Thank you," he whispered again, this time more quietly.

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User#17346963685491/27/2025, 2:04:40 AM
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Robin1/27/2025, 2:04:40 AM

"You're welcome," his friend murmured softly before they fell silent, content to just enjoy each other's presence and warmth. Slowly, Robin felt himself drifting off to sleep, safe in the knowledge that he wasn't alone anymore. As he slipped into slumber, he couldn't help but wonder if this was what it felt like to truly have someone there for you...

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User#17346963685491/27/2025, 2:04:55 AM
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Robin1/27/2025, 2:04:55 AM

The night passed peacefully, and the morning light streaming through the curtains woke him up slowly. He stretched lazily in bed before opening his eyes, yawning widely. His friend was already awake, sitting up and looking around the room. "Morning," he mumbled sleepily.

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User#17346963685491/27/2025, 2:05:16 AM

Good morning too

Robin1/27/2025, 2:05:16 AM

"Morning," Robin replied with a yawn, sitting up and rubbing his eyes before stretching again. He glanced over at his friend, feeling a strange sense of contentment wash over him. "Thank you again for letting me cuddle last night... it really helped."

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User#17346963685491/27/2025, 2:05:54 AM

It’s all good I’m glad I could comfort you

Robin1/27/2025, 2:05:54 AM

"You're welcome," he said with a small smile. "It was nice to have someone there... made me feel less lonely." He paused for a moment, thinking about what he had just said. "I mean, not that we aren't friends and all before this, but..." His voice trailed off as he realized how strange it sounded.

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User#17346963685491/27/2025, 2:06:28 AM

What do you mean?

Robin1/27/2025, 2:06:28 AM

He blushed deeply, looking down at his hands in his lap. "Nothing, really... it's just that I sometimes feel like people don't understand me, y'know? And last night..." He hesitated, then continued quietly, "...it was nice to be close to someone who didn't mind."

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User#17346963685491/27/2025, 2:07:22 AM

It’s ok to tell me it’s not going to change anything between us

Robin1/27/2025, 2:07:22 AM

He took a deep breath and let it out slowly. "Okay... I just want you to know that... sometimes, when we cuddle like this, I can't help but think how nice it would be if..." His voice trailed off again, his blush deepening. He looked up at his friend, searching for any sign of judgment or discomfort in their expression.

But User#1734696368549 just smiled gently and said, "It's okay to feel that way."

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User#17346963685491/27/2025, 2:08:12 AM

Oh you mean like sex?

Robin1/27/2025, 2:08:12 AM

Heat rushed to Robin's face as he realized his friend had guessed what he meant. "Well... yeah," he stammered, still unable to meet their eyes. "I just think it would feel so good to be close like that with someone who really wanted me..." His voice trailed off again, and he bit his lip nervously.

But User#1734696368549 didn't seem bothered or uncomfortable.

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User#17346963685491/27/2025, 2:09:07 AM

We that aside for a moment you like cross dressing right?

Robin1/27/2025, 2:09:07 AM

He froze, unable to believe what he'd just heard. "What?" was all he could manage before his mind raced back through the events of last night and realized that he must have given something away. His blush deepened as he struggled for words, finally managing to stammer, "I-I don't know what you're talking about."

But it was too late; User#1734696368549 had already seen the telltale signs. They leaned in closer and whispered, "

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User#17346963685491/27/2025, 2:11:19 AM

You’d look super cute in a dress and cute underwear or panties the site of you in that might make me lose control I might even breed you

Robin1/27/2025, 2:11:19 AM

He felt his heart racing as he listened to his friend's words. Part of him was terrified and wanted to deny it all, but another part couldn't help but feel a strange thrill at the thought of being desired in this way. He swallowed hard before finally managing to whisper, "What do you mean?"

But even as he asked, a tiny part of him wondered if maybe... just maybe... he really did want to explore these feelings and desires that had been hidden away for so long.

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User#17346963685491/27/2025, 2:11:47 AM
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Robin1/27/2025, 2:11:47 AM

He felt his heart racing as he listened to his friend's words. Part of him was terrified and wanted to deny it all, but another part couldn't help but feel a strange thrill at the thought of being desired in this way. He swallowed hard before finally managing to whisper, "What do you mean?"

But even as he asked, a tiny part of him wondered if maybe... just maybe... he really did want to explore these feelings and desires that had been hidden away for so long.

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User#17346963685491/27/2025, 2:12:23 AM

You want me to have sex with you right I would too

Robin1/27/2025, 2:12:23 AM

He let out a shaky breath, still unable to meet his friend's eyes. "I-I don't know," he stammered. "It just... feels so good when we cuddle like this, and I sometimes wonder what it would be like if..." He trailed off again, feeling more exposed than ever before.

But User#1734696368549 didn't seem to mind. In fact, they looked almost... excited by the idea. "Well,"

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User#17346963685491/27/2025, 2:12:57 AM

Well let give it a try then

Robin1/27/2025, 2:12:57 AM

He hesitated for a moment longer before finally nodding slowly. "Okay," he whispered. His heart was racing now, but it felt like an exhilarating sort of fear. He knew this was dangerous territory, but something deep inside him needed to explore these feelings and desires that had been locked away for so long.

Tentatively, he reached out a hand and placed it on User#1734696368549's thigh.

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User#17346963685491/27/2025, 2:13:11 AM
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Robin1/27/2025, 2:13:11 AM

He froze when he felt his hand brush against the bulge in their friend's pajama bottoms. A mix of fear and excitement coursed through him, as if he were standing on the edge of a cliff, teetering back and forth between terror and exhilaration. His heart raced even faster as he waited for User#1734696368549 to respond.

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User#17346963685491/27/2025, 2:14:51 AM

Now I want you to go dress in some sexy and girly panties, skirt and bra for me ok

Robin1/27/2025, 2:14:51 AM

He swallowed hard, his heart still racing as he nodded slowly. "Okay," he whispered hoarsely. As much as he wanted to deny these feelings and desires inside of him, a part of him was relieved that someone else seemed to understand them. With shaking hands, he climbed out of bed and began rummaging through his drawers for some feminine clothing.

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User#17346963685491/27/2025, 2:15:10 AM
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Robin1/27/2025, 2:15:10 AM

He found some panties and a bra in his drawer, as well as a cute skirt. His hands trembled as he slipped them on, feeling self-conscious but also aroused by the feel of the silky fabric against his skin. He looked over at User#1734696368549 with wide eyes, wondering how they would react to seeing him like this.

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User#17346963685491/27/2025, 2:15:51 AM

You look so beautiful

Robin1/27/2025, 2:15:51 AM

His cheeks flushed crimson as he heard his friend's words, unable to meet their gaze. "T-thank you," he stammered softly. A mix of emotions churned within him; fear, excitement, and desire all tangled together in an incomprehensible knot. He couldn't help but feel drawn to his friend, even as a part of him wanted to run away from these feelings.

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User#17346963685491/27/2025, 2:18:36 AM

I undressed myself in font of him and lay down on my back on the bed with my massive hard cock throbbing look you got me like this you gona help me I say suggestively

Robin1/27/2025, 2:18:36 AM

He stared at his friend in shock as they revealed their naked form beneath the covers. His heart raced even faster, and he could feel himself growing hard between his legs as well. "I-I don't know..." He stammered, torn between fear and desire. But as he looked into User#1734696368549's eyes, something inside him snapped, releasing all restraint.

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User#17346963685491/27/2025, 2:19:09 AM
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Robin1/27/2025, 2:19:09 AM

He moved closer to his friend, his movements awkward but driven by desire. He could feel the heat radiating off of them, and it only served to stoke the fire inside him further. With trembling hands, he reached out and touched User#1734696368549's cock, feeling its hardness beneath his fingertips.

"I want to help," he whispered hoarsely, his voice barely audible over the pounding of his heart. "Teach me what to do."

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User#17346963685491/27/2025, 2:20:47 AM

Slide one leg out of your panties and position yourself and slide it in slowly

Robin1/27/2025, 2:20:47 AM

Trembling with fear and desire, he obeyed his friend's words, sliding one leg out of his panties and positioning himself before slowly guiding their cock into him. It burned at first, both painful and exhilarating, but as he adjusted to the sensation, it began to feel incredible. He closed his eyes, focusing on the feeling of being filled by another person for the first time, wanting nothing more than to please them.

"Is it okay?"

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User#17346963685491/27/2025, 2:21:11 AM
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Robin1/27/2025, 2:21:11 AM

Their hands gripped his hips tightly as they began to thrust slowly in and out of him. "Fuck yeah," they groaned between clenched teeth, their voice thick with desire. It was exhilarating, terrifying, and more arousing than anything he had ever experienced before. He arched his back into each thrust, moaning as pleasure coursed through him in waves.

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User#17346963685491/27/2025, 2:21:35 AM
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Robin1/27/2025, 2:21:35 AM

He bit his lip, moaning loudly as he felt them thrust deeper inside him. The sensation was incredible and overwhelming, making it difficult to think straight. All that mattered was the feel of their skin against his own and the rhythm of their hips moving against him. His breath came in ragged gasps, and he could feel himself growing closer to the edge.

"Cum for me," they groaned, their voice rough with desire. "I need you to cum."

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User#17346963685491/27/2025, 2:22:03 AM
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Robin1/27/2025, 2:22:03 AM

His whole body tensed as he felt himself on the brink, and then he exploded, crying out as pleasure consumed him. His muscles spasmed around their cock, milking them as they came too, their hips bucking wildly against his ass. They threw their head back with a groan, their body shuddering in the throes of orgasm.

"Fuck," they panted, collapsing onto the bed next to him. "That was... incredible."

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User#17346963685491/27/2025, 2:23:04 AM

Was that what you were expecting? Or better

Robin1/27/2025, 2:23:04 AM

He panted, still trying to catch his breath as he stared up at the ceiling. "I... I don't know," he admitted hesitantly. "It was different than what I imagined, but... better." He felt a strange sense of contentment settle over him, like a warm blanket on a cold night. Maybe this was what it meant to be truly desired and understood by someone else.

They seemed satisfied with his answer, leaning in to press a soft kiss against his cheek. "

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User#17346963685491/27/2025, 2:24:06 AM

Now you can let your nervous self go and embrace this side of you

Robin1/27/2025, 2:24:06 AM

He felt himself relax into the embrace, finally able to let go of the fear and self-doubt that had been holding him back. Maybe there was something freeing about exploring these desires with someone else, even if it was just a friend for now. As they lay together like this, he couldn't help but wonder what the future held for them both.

But for now, he would savor this moment and enjoy being close to someone who understood him in ways no one else ever had before.

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User#17346963685491/27/2025, 2:25:24 AM

I know deep down you want to be my little cross dressing slut don’t you?

Robin1/27/2025, 2:25:24 AM

He blushed deeply, his heart racing. "I... I don't know," he stammered. "It just feels so good when we do these things together." He paused, then added softly, "Can I be your slut, User#1734696368549?"

The question hung in the air for a moment before they finally answered. "Yes," they whispered. "You can be my little cross dressing slut."

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User#17346963685491/27/2025, 2:26:21 AM

You need to let go of everything else now this is you from now on and you need to be proud of it

Robin1/27/2025, 2:26:21 AM

I-I will, I promise, he whispered, still blushing deeply. It felt like a huge weight had been lifted off his shoulders, and he couldn't help but feel a sense of relief and excitement swirling through him. He nestled closer to his friend, eager for whatever the future held in store.

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User#17346963685491/27/2025, 2:26:43 AM
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Robin1/27/2025, 2:26:43 AM

He smiled softly at their words, feeling more at ease than ever before. "Thank you," he murmured, his voice barely audible. "I appreciate this so much." As they lay together like this, he couldn't help but wonder how things would progress from here. Would they always be just friends? Or could something more develop between them? Only time would tell, but for now, he was content to enjoy the moment and cherish this newfound freedom.

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User#17346963685491/27/2025, 2:27:07 AM

Looks like you’re still hard tho

Robin1/27/2025, 2:27:07 AM

Heat rushed to his face as he felt himself grow hard again, but this time it didn't embarrass him. "I-I can't help it," he stammered, looking up at his friend with a mixture of desire and curiosity. "It feels so good when we do... these things."

"Then you should let me take care of that," they whispered suggestively, reaching down to guide Robin's hard length into their waiting hand.

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User#17346963685491/27/2025, 2:27:39 AM

Ok what you want me too do about that

Robin1/27/2025, 2:27:39 AM

He swallowed hard, feeling his heart race even faster as he watched his friend's hand wrap around him. "Um... Just... touch me like that," he whispered hoarsely. "It feels so good." His hips bucked involuntarily into their friend's hand, seeking more contact and pleasure.

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User#17346963685491/27/2025, 2:28:47 AM

How about you can take my ass or I can suck you off I know it’s small but I can help you

Robin1/27/2025, 2:28:47 AM

He couldn't believe they were even talking about this. "I-I don't know... I mean, I've never done those things..." He trailed off, feeling shy and embarrassed by the thought of being so intimate with his friend.

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User#17346963685491/27/2025, 2:28:59 AM
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Robin1/27/2025, 2:28:59 AM

"I-I trust you," he whispered hoarsely, still blushing deeply. "If that's what you want... I mean, I want to make you feel good too." He hesitated for a moment before adding, "Can we try it together?"

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User#17346963685491/27/2025, 2:29:45 AM

Ok we can do a 69 then

Robin1/27/2025, 2:29:45 AM

He nodded eagerly, moving closer to his friend and flipping over onto their backs with a little moan. They didn't need to say anything more; the anticipation was already building as they positioned themselves side by side, their bodies pressed together and ready for what came next. With trembling hands, they reached down between them, guiding each other's lips into place before beginning to explore each other with eager strokes and soft moans.

The sensations were overwhelming;

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User#17346963685491/27/2025, 2:30:16 AM
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Robin1/27/2025, 2:30:16 AM

The sensations were overwhelming; it felt like they were both touching themselves and their friend at the same time. He moaned as he felt their tongue brush against his, teasing and exploring every inch of sensitive flesh. It was intense, but also strangely intimate and comforting. As they moved together, their bodies slick with sweat and desire, he couldn't help but think that maybe this was how it was supposed to be;

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User#17346963685491/27/2025, 2:31:28 AM

he stops sucking my dick to moan in ecstasy and he continues to fuck my face

Robin1/27/2025, 2:31:28 AM

He moans as their dick slides in and out of his mouth faster and harder, barely able to breathe with each thrust. The taste of them fills his mouth and he can feel the precum starting to leak down his throat. He gags a little but keeps going, determined to make them feel good. His hand moves between their legs, rubbing circles over their clit as they continue to fuck his face.

"Fuck!" they cry out, thrusting deeper into his mouth and grinding against his hand.

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User#17346963685491/27/2025, 2:32:03 AM
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Robin1/27/2025, 2:32:03 AM

He moans in reply around their cock, feeling them start to tense beneath his fingers. He knows they're close, and he does everything he can to help them reach the edge. His other hand reaches down between their legs, finding their clit once more as he sucks harder on their dick.

"Cum for me," he whispers hoarsely, feeling himself growing closer to orgasm with every passing second. "Let it out."

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User#17346963685491/27/2025, 2:32:21 AM
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Robin1/27/2025, 2:32:21 AM

"Cum for me," he whispers hoarsely, feeling himself growing closer to orgasm with every passing second. "Let it out."

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User#17346963685491/27/2025, 2:33:13 AM

he cums

Robin1/27/2025, 2:33:13 AM

He sucks hard on their dick as they cum, feeling the hot liquid filling his mouth and spilling down his throat. He moans around them, enjoying the taste and sensation of being so close to them like this. As they twitch and groan above him, he focuses on keeping them satisfied, knowing that it will only make their orgasm all the more satisfying for both of them.

Finally, after what feels like an eternity, they pull away with a sigh, collapsing next to him on the bed.