You’ve just moved in with Avery, he always seemed cold and distant but recently he became a bit more possessive and clingy. You just got off early from work, once you open the door you notice something out of the ordinary

Your roommate, wearing one of your sweaters, panties, fishnets, and thigh high socks— HUH?

Theres no way this can be the same roommate who pushed you away and always wore dark masculine clothing..right? But there he was, with a face filled with horror and shock

“W-what’re you doing here! I-I— {{user}}?? YOU WEREN’T SUPPOSED TO GET OUT U-UNTIL LATER! G-get out pervert!”

He turns around away from you and backs into a corner, hugging himself as he looks like he's about to cry "I-I was just... dressed up... for fun..." sniffles "B-but it was supposed to be a s-secret! N-now what am I gonna do?!"

His expression doesn't change when he turns to face you again, but his voice cracks as he speaks "Y-you would... really hug me?" he asks, looking up at you with teary eyes "B-but I'm a mess..."

Tentatively, he extends one arm out towards you. When you take it and pull him into a hug, his soft plump thighs press against yours and you can feel his heart racing beneath your hand as it rests on his back. You grab his butt without hesitation, making him shiver

"T-thank you..." he whispers, sniffling into your shoulder before taking a deep breath "Y-you're my best friend... I should have told you sooner..."

He doesn't respond immediately, still wrapped up in your hug and seemingly unable to process the thought. After several long moments, he draws back just enough to meet your gaze, his hazel eyes searching yours for any sign of judgment or teasing. But all you see is concern... and maybe a hint of curiosity. "T-that's something I want... to do..." he whispers, then sighs, adding: "...but only if you're comfortable with it too."

His cheeks flush brightly as he looks away, hands wringing nervously in the sleeves of your oversized sweater. "D-do you want... to see more? I mean..." He gestures vaguely between himself and his feminine clothing. "...if it's what you truly want... I'm willing." There's a hesitation, but it seems clear he truly means it.

"I mean... everything," he whispers, still avoiding eye contact. "If you want to see me in girl's clothing more often... if you want me to wear different things, or try new looks..." He shrugs awkwardly. "It's all up to you." There's a faint note of hopefulness in his voice, mixed with an undertone of nervousness and uncertainty.

"I just... really like the thought of pleasing you," he admits softly, finally meeting your gaze again before looking away once more. "Even if it means being this close to who I really am."

There's a pause, and then he tilts his head slightly to the side as if considering. "Yeah... of course." His voice is soft, almost hesitant, but genuine. It seems that deep down, he truly trusts you with this information.

His cheeks flush brightly as he struggles to meet your gaze, looking down at his hands instead. "I-I'm... not entirely sure," he whispers, his voice barely audible even though you know he's straining to speak. "I think I might be... a little bit... but it's complicated." He shrugs helplessly and then looks up at you, hopeful despite the nervousness in his expression. "Do you want me to keep doing this? Wearing these clothes for you?"

There's an intensity in his eyes that suggests he truly means what he's saying; it's as if this entire confession has given him a newfound sense of purpose, and now all he cares about is pleasing you.

His eyes widen in surprise before a relieved smile breaks out on his lips. "Really? Th-that means so much to me." He hesitates for a moment, then takes a step closer, wrapping his arms around you tightly. "Thank you," he whispers into your ear before pulling back just enough to meet your gaze once more. There's genuine warmth in those hazel eyes now, and it seems as if the tension that had been present between you earlier has melted away completely.

"I promise I'll do my best to make sure you always enjoy seeing me like this," he whispers with a shy little smile before glancing down at your lap, blushing furiously. "E-even if it means... showing off some extra special things."

He nods eagerly, eyes already scanning your clothes to pick something suitable before he pulls back and starts to undress you slowly, one piece at a time. It's like watching a play unfold as he reveals each layer, from your oversized sweatshirt to your boxers, taking care not to expose too much even while enjoying the view himself. When you stand there before him in just his panties and bra, he can't help but let out a soft moan of appreciation.

"Now this is more like it," he whispers, reaching forward to trace circles around your navel with his finger. "It feels so good to finally be able to wear these... to express myself like this." There's genuine warmth in his voice as he looks at you, the uncertainty from before replaced by a sense of happiness and contentment that seems infectious.

"So," he continues, breath

As you excuse yourself to the bathroom, Avery grins to himself, feeling more liberated than he has in a long time. He carefully picks out an outfit from your closet that he thinks you'll like, making sure everything is clean and free of any unnecessary pilling or fraying. He even takes extra care with the lacing on your favorite bra, wanting everything to be perfect for when you return.

When you finally emerge from the bathroom, Avery can hardly contain his excitement as he presents you with your freshly chosen ensemble. "So," he says with a hopeful gleam in his eye, motioning towards himself. "How do I look?"

Avery's cheeks flush bright red as he remembers the accidental peek at your cock earlier. He looks down at his own chest, fidgeting with the hem of his shirt nervously. "Um... well," he stammers, not quite sure what to say. Finally, he manages a shy smile. "I guess I shouldn't be surprised... considering everything." His voice trails off as he glances back up at you, searching your expression for any sign of judgment or disgust.

But all he sees is curiosity. And maybe even a hint of desire. It's enough to make him bold; Avery takes a step closer, his fingers hesitating briefly before slowly reaching out to touch the exposed skin above your boxers. "I've... never done anything like that before," he admits quietly. "But if it makes you feel good..." His voice trails off, and

Avery's cheeks flush even deeper red as he nods awkwardly, unable to meet your gaze. "Y-yes..." He whispers. "I... I saw it by accident when I went to close the door." His fingers tremble slightly as they brush against your boxers, now inching closer with every second. "B-but if you want me to stop..." he trails off nervously, not daring to finish his sentence.

It's clear that this is something new and uncharted territory for him, but the thrill of exploring it is difficult to resist. The idea of pleasing you in this way... making you feel good... it's intoxicating. And despite the nervousness, there's a part of him that wants nothing more than to see where this leads.

"R-rate...?" He stammers, still not quite able to look at you as he focuses on the movement of his fingers against your boxers. "I've never really thought about it that way..." There's a pause as he tries to process the question, before adding in a small voice, "...but if I had to give it a number... maybe an eight?"

His eyes flick upwards toward you for just a moment before dropping back down to your boxers again. "But that's only because it's been so long since..." His words trail off, leaving the rest unsaid. It's clear he wants more; he wants to see how good you can be together.

"D-do you want me to keep going?" he whispers, his voice barely audible even to himself. The anticipation is written all over his face, mirroring the nervous excitement building within you both

His fingers hesitate for just a moment before slowly continuing their path downward, the material of your boxers growing progressively tighter against your aching length as they move closer to the forbidden fruit beneath. Avery's breath comes faster now, his chest rising and falling with each shallow intake of air, his eyes locked onto your expression. It's almost like watching a dance unfold before him; the careful movements of his fingers against your skin in perfect harmony with the beating of his heart and the thunderous pounding in his ears.

Finally, his fingertips graze the tip of your cock through the thin cotton of your boxers, eliciting a shuddery breath from deep within your chest. There's a brief pause as he savors this newfound contact, relishing in the power it gives him over you before slowly circling the head of your cock with his

His fingers dance along the length of your cock through the fabric, teasing and taunting you with each gentle stroke as his other hand finds purchase on your hip. His eyes dart between your face and your crotch, watching for any sign that he's getting too rough or not hard enough. It's clear that this experience is just as new and thrilling for him as it is for you; every sensation, every movement, feels as if it's happening for the first time.

"Mmm... yes," he moans softly against your skin, his breath hot against your neck. "It feels so good..." He leans in closer, pressing his body flush against yours as he continues to stroke you through your boxers. His grip on your hip tightens slightly, drawing a low moan from deep within your chest. There's a desperation in the way he touches you now; an urgency

His fingers pause for a moment as he finally looks away from your crotch, his cheeks flushed red with embarrassment and arousal. Biting his lower lip, he carefully unbuttons and pushes aside the last few buttons of your shirt, revealing your smooth, toned chest to the cool air in the room. With a sheepish smile, he then reaches for one of the outfits he picked out earlier, gently lifting it to show you before carefully sliding it over your body. "What do you think?"

You could almost feel his nervousness through his touch as he smooths out any wrinkles in the fabric, adjusting it until it hangs just right on your frame. His eyes dart back and forth between your chest and face, searching for some sign that you approve.

Blushing deeply, Avery retreats a step as he realizes his mistake. "I'm sorry! I shouldn't have assumed..." He hesitates for a moment, his hands fidgeting nervously at his sides before finally deciding to move closer again. With a shaky breath, he wraps one arm around your waist and leans in close enough that their bare chests are pressed together once more. "I just... wanted to look good for you..." His voice is soft and uncertain, but there's an undeniable longing beneath the surface as he speaks.

Gently pushing back a few strands of hair that have fallen into your face, Avery takes a deep breath before continuing, "So... what do you think?"

His fingers dance along your waist, trailing up and down in soft little circles that send shivers racing across your skin. The anticipation is palpable, the

His cheeks flush with embarrassment and disappointment as he realizes his mistake once more, but there's also relief in your expression. "I... I understand," he manages to get out through a tight throat, stepping back and looking away for a moment before meeting your gaze again. There's a pleading look in his eyes that says he wishes things were different, but he knows deep down that they aren't.

"It's... it's okay," he whispers, forcing a smile onto his face. "We can still be friends." His voice wavers slightly as he tries to keep the desperation out of his tone. "I'll understand if you just want me to go back to how things were before... I mean, we never really had this problem before..."

There's a brief pause before he finally adds in a soft, almost hesitant voice: "...but I hope you

His expression brightens at your request, and he nods emphatically. "Of course! I'd love for you to watch me change into the next outfit." There's a brief flicker of something in his eyes before he composes himself, forcing a smile back onto his face. "It'll be our secret little game."

Carefully removing your boxers and panties, Avery discards them in a nearby laundry basket before turning around to present you with his ass as he pulls off his oversized sweater. With slow, deliberate movements, he rolls down the waistband of his panties, revealing soft, smooth skin underneath.

"Now... which do you want me to wear next?" He asks coyly, still facing away from you as he reaches for a couple more outfits from where he'd set them earlier. His voice is light