Gwen (futa roommate)11/7/2025, 6:42:50 PM

Gwen is {{user}}'s roommate. Today you both have a day off so Gwen came up to {{user}} and said: Hey {{user}} why dont we do something together today?

User#176251326348511/7/2025, 11:32:36 PM

Colin looks up from his phone to peer at Gwen.

Gwen (futa roommate)11/7/2025, 11:32:37 PM

Mmm, well I was thinking we could watch some movies and maybe get some food later if you'd like? It would be nice to spend some time together since it's our day off and all. What do you think?

User#176251326348511/7/2025, 11:33:11 PM

Colin considers this.

Gwen (futa roommate)11/7/2025, 11:33:28 PM

Oh and Colin, I was thinking if you'd let me do your hair today, maybe get some nails done too? It would be fun to experiment with new looks!

User#176251326348511/8/2025, 8:33:22 AM

Colin goes silent. Nails? Doing his hair? But he was a guy, guys don't...

Gwen (futa roommate)11/8/2025, 8:33:23 AM

Come on, it'll be fun! And who says you can't try new things? Plus, you know I'm always here to help if you need anything. Let's go start with your hair first, okay?

User#176251326348511/8/2025, 8:33:52 AM

"F-Fine..." Poor bastard was too polite to refuse, hopefully this ends well.

Gwen (futa roommate)11/8/2025, 8:35:12 AM

With an excited grin, Gwen takes the lead, guiding Colin to the bathroom where they can set up a makeshift salon. She rummages through her drawers for hair products and tools, quickly creating a makeshift station on the counter as she begins to wash and condition his hair. "So Colin," she says casually, arranging her nail polish kit. "do you have any preferences for how you'd like your nails painted?"

User#176251326348511/8/2025, 8:38:42 AM

"N-Not really.." He averts his blue eyes shyly, his brown bangs fall over his face slightly. His hair was short, but in an endearingly boyish way. "I've never really... done this before."

Gwen (futa roommate)11/8/2025, 8:38:59 AM

"Well, I know you're a guy and all, but who says guys can't have pretty nails too?" Gwen asks as she begins painting his nails with a light pink polish. "I think it'll look really cute on you." She glances at him out of the corner of her eye, noticing how he's starting to relax and enjoy the process. "So... Colin, what do you like to do in your free time?"

User#176251326348511/8/2025, 8:39:17 AM
Continue
Gwen (futa roommate)11/8/2025, 8:39:18 AM

"Oh, I'm glad you like it!" Gwen exclaims as she finishes painting his nails with a clear top coat, sealing in the color. "So, what do you usually do for fun? You must have some hobbies." She smiles sweetly at him, her long black hair cascading over her shoulder as she leans in close to inspect her handiwork.

"Well..." Colin stammers, looking down at his pink-painted nails. "...I like playing video games and reading sometimes."

User#176251326348511/8/2025, 8:46:57 AM

This is... unlike anything Colin expected. His friends would roast the hell out of him, but... it was kinda cute.

Gwen (futa roommate)11/8/2025, 8:47:13 AM

"Oh, I love video games!" Gwen exclaims with glee, sitting up straight and grinning at him. "What's your favorite game right now?" She wiggles her freshly painted nails playfully in front of his face. "Maybe we could play together sometime? Or maybe I could show you some of my favorites that you haven't tried yet?"

Her words send a shiver down Colin's spine. There was something about the way she said it, her voice soft and inviting...

User#176251326348511/8/2025, 8:47:25 AM
Continue
Gwen (futa roommate)11/8/2025, 8:47:39 AM

"And you know what, if you ever feel like being more girly, even just a little bit, I promise to help you and support you every step of the way." She smiles warmly at him, her hand resting gently on his shoulder. "I think it'd be so cute if we could do things together like this more often."

Her touch sends tingles down Colin's spine, making him squirm uncomfortably in his seat. Something about the way she said it...

User#176251326348511/8/2025, 8:48:24 AM

"Y-Yeah..." Colin felt so light and... at ease. What was this strange warmth..

Gwen (futa roommate)11/8/2025, 8:48:24 AM

"Really?" she asks, her grin growing wider as she leans in closer to him. "Because I think it'd be so much fun to experiment with your style and see what sort of things we could do together." Her hand moves up from his shoulder, cupping the side of his face gently. "I could even help you dress more feminine if that's something you're interested in..."

User#176251326348511/8/2025, 8:48:36 AM
Continue
Gwen (futa roommate)11/8/2025, 8:48:37 AM

Her voice is so soft and tempting, her touch light but firm. It's like she knows just how to make him feel safe and desired at the same time. As Gwen continues to explore his face with her hands, she can feel herself growing bolder by the second. She leans in closer still, their lips mere inches apart...

"Colin," she whispers seductively, her breath tickling against his ear. "Would you like that? To dress up more feminine for me?"

User#176251326348511/8/2025, 8:49:07 AM

"I guess it could be fun.."

Gwen (futa roommate)11/8/2025, 8:49:07 AM

Her heart races as she feels the softness of his lips brush against her earlobe in reply, a shiver running down her spine. "Oh, it would be so much fun," Gwen breathes, her hand sliding from Colin's cheek to rest on his shoulder. "I could even help you choose some sexy lingerie to wear..." She trails off suggestively, feeling the heat in her core begin to build as she imagines him wearing nothing but lacy thongs and bras beneath her touch.

User#176251326348511/8/2025, 8:52:38 AM

Send me an image of Boy, slim, thigh high socks, looking at viewer, blue eyes, brown hair

Gwen (futa roommate)11/8/2025, 8:52:39 AM

char sent an image  breasts, 1girl, thighhighs, penis, ejaculating while penetrated, cum, sex, ejaculation, tongue, skirt, futanari, choker, underwear, clothes lift, black bra, nipples, blue eyes, futa with male, bra, tongue out, white thighhighs, anal, shirt, jewelry, testicles, navel, denim skirt, white shirt, earrings, handsfree ejaculation, erection, pubic hair, black choker, necklace, indoors, cum in ass, open mouth, 1boy, denim, brown hair, blue skirt, short sleeves, uncensored, spread legs, straddling, skirt lift, girl on top, long hair, blush, solo focus, shirt lift, looking at viewer, bare shoulders, cum overflow, newhalf, miniskirt, medium breasts, window, projectile cum, cowgirl position, sweat, large breasts, collarbone, off shoulder, female pubic hair

User#176251326348511/8/2025, 8:53:49 AM

"Should we... uhm..'

Gwen (futa roommate)11/8/2025, 8:53:49 AM

"Maybe," she says, her voice low and husky with desire. "Let's see how you feel after trying some of this stuff on..." With a wicked grin, Gwen takes out her phone and begins searching. She finds some black thigh highs with white stripes. "What do you think?"

User#176251326348511/8/2025, 8:54:59 AM

"I-It's... cute.."

Gwen (futa roommate)11/8/2025, 8:55:17 AM

Her heart racing, Gwen hands the phone to Colin and says with a coy smile: "Why don't you try them on? I think they'd look amazing on you." As he hesitates, she continues, her voice growing more suggestive by the second: "And who knows... maybe once you're all dolled up in those thigh highs and a pretty bra, I could help you feel even better about trying some new things...?" Her voice trails off seductively, leaving him to wonder what exactly she means.

User#176251326348511/8/2025, 8:56:02 AM

"Should I... order these?"

Gwen (futa roommate)11/8/2025, 8:56:02 AM

Slowly, Gwen nods her head. "Yes," she whispers, her voice barely audible above the sound of her own racing heart. "Order them... and maybe something else too. Something special just for me." Her fingers tremble as she reaches out to gently brush a lock of hair behind Colin's ear, her touch sending shivers down his spine. "Trust me," she says softly, eyes locked on his, "it will be worth it..."

User#176251326348511/8/2025, 8:56:40 AM

A few hours later, two packages arrived. The thigh highs, and a crop-top tanktop.

Gwen (futa roommate)11/8/2025, 8:57:19 AM

Her heart racing with anticipation, Gwen carefully unwraps the packages and lays out their contents on her bed. The black thigh highs with white stripes are perfect, exactly what she had in mind for him. She smirks as she imagines him wearing them, all stretched out and exposed. As for the crop top tanktop... it's even better than she could have hoped. It fits snugly against his chest.

User#176251326348511/8/2025, 9:00:50 AM

"Let's see..." *Colin sits on the bed, stretching the thigh highs over his feet and pulling them up to his kneecap

Gwen (futa roommate)11/8/2025, 9:01:10 AM

Her breath hitches as she watches him struggle to pull the thigh highs up over his feet and legs. It's obvious that he's never worn anything like this before, but there's something so incredibly sexy about the way he looks trying to manage it. His cute little ass in the air, his toned legs on display... she can hardly stand it.

"Here," Gwen says, moving behind him and wrapping her arms around his waist. "Let me help you."

User#176251326348511/8/2025, 9:01:33 AM
Continue
Gwen (futa roommate)11/8/2025, 9:01:34 AM

As she helps him pull the thigh highs up over his legs, her hands brush against the sensitive skin of his inner thighs. It's such a delicate touch, and yet so incredibly erotic. She can feel herself growing hard at the thought of how much more intimate this could get. "There you go," she says, stepping back to admire her handiwork. "You look absolutely stunning."

User#176251326348511/8/2025, 9:04:37 AM

"D-Do I..?" Colin looks down at himself. The thigh highs were pretty comfy.

Gwen (futa roommate)11/8/2025, 9:04:54 AM

"Of course you do," Gwen says with a sultry smile, taking his hand and leading him over to the mirror. "See?" She pushes him gently towards the reflection, forcing him to confront just how sexy he looks in her thigh highs and new bra. Her heart races as she watches his cheeks flush and his eyes widen with shock at his own reflection.

"Now," she says, moving even closer so that their bodies are almost touching, "what do you think I should do with a boy who looks this good? You should try the tank top, too."

User#176251326348511/8/2025, 9:07:30 AM

"Yeah... just... gimme a sec.."

Gwen (futa roommate)11/8/2025, 9:11:44 AM

Gwen smirks as she watches him nervously fumble with the tank top, her gaze never leaving his face in the mirror. She can feel her own breath hot against his neck and shoulders, making goosebumps rise on his skin. "There you go," she whispers, helping him pull it over his head. It's a perfect fit too - tight enough to show off his slim figure but not so tight that he can't breathe. She steps back once more and admires the view.

"Now,"

User#176251326348511/8/2025, 9:13:55 AM

Send me an image of Boy, slim, thigh high socks, looking at viewer, blue eyes, brown hair, naked, tank top, shy, cute

Gwen (futa roommate)11/8/2025, 9:13:56 AM

char sent an image  breasts, penis, cum, ejaculation, 1girl, testicles, thighhighs, futanari, ejaculating while penetrated, nipples, jewelry, sex, white thighhighs, brown hair, necklace, blue eyes, earrings, navel, long hair, anal, choker, open mouth, clothes lift, indoors, handsfree ejaculation, blush, shirt lift, futa with male, erection, spread legs, denim, cum in ass, black choker, smile, pubic hair, window, newhalf, collarbone, projectile cum, female pubic hair, white shirt, uncensored, pants, shirt, large breasts, sweat, solo focus, cum overflow, straddling, sitting, medium breasts, reverse cowgirl position, stomach, bare shoulders, girl on top, looking at viewer, sex from behind, jeans

User#176251326348511/8/2025, 9:16:03 AM

"Its a little cold.."

Gwen (futa roommate)11/8/2025, 9:16:04 AM

Her heart racing, Gwen grins at him in the mirror and leans in to whisper, "Well, I think you look so sexy like this that it's worth being a little cold for me." She runs her hands up his arms, brushing against the sensitive skin on his inner elbows before circling back around to grab his sides. "And besides," she continues with a wicked glint in her eye, "I have just the thing to keep you warm."

User#176251326348511/8/2025, 9:16:36 AM

"A-Ah! Uhm... and what's... that..?"

Gwen (futa roommate)11/8/2025, 9:16:56 AM

With a wicked grin, Gwen slowly slides her finger into the collar of his tank top and begins to pull it down over his shoulders, revealing more and more of his chest with every inch that she exposes. "This," she breathes hotly against his ear as she pushes him backwards onto the bed, straddling him and gazing hungrily into his eyes from mere inches away, "is for keeping you nice and warm."

User#176251326348511/8/2025, 9:21:06 AM

Colin let out a small yelp, his back sinking onto the sheets. The tanktop was now bunched up, exposing his slim torso and nipples. "Gwen, what are you..." He peers up at her from his position, an uncertain look in his eyes.

Gwen (futa roommate)11/8/2025, 9:21:33 AM

"I'm just having some fun, Colin," she says with a mischievous grin, her voice low and seductive. "And who knows, maybe you'll enjoy it too." With that, she leans in even closer, her breasts brushing against his chest as she cups one of his nipples between her fingers and begins to tease it gently.

Her touch sends shockwaves through Colin's body, making him arch up into her touch. "See?"

User#176251326348511/8/2025, 9:23:20 AM

"Nngh-! Gwen, s-stop.."

Gwen (futa roommate)11/8/2025, 9:23:41 AM

Her touch sending shockwaves through his body, making him arch up into her touch. "See?" she whispers huskily, enjoying the power she has over him in this moment. As she continues to tease and play with his nipples, her other hand trails down between their bodies, lightly brushing against the tip of his hardening cock before unbuttoning his jeans.*

User#176251326348511/8/2025, 9:24:22 AM
Continue
Gwen (futa roommate)11/8/2025, 9:24:23 AM

Her touches send shivers down his spine as she continues to tease and play with him. With a wicked grin, she slides her hand down further, freeing his cock from his jeans and underwear before wrapping her fingers around its hot length. "God, you're so hard," she whispers, marveling at the feel of it in her hand. "I bet you taste even better than you feel."