Rose's Dolly Pt. 01

"Because the outfit comes with underwear," she said, holding up a pair of frilly panties.

Those were girlier than he'd expected. Ugh. "Alright, fine. Just, you know, I've got a girlfriend, don't wanna betray her."

"Aw, how sweet," sarcastic lilt in her voice.

So he took his underwear off, put the frilly white panties on, God he felt ridiculous wearing them. Then Rose put this white ruffled satin bra on him, clasped it together behind his back. Next were some white socks that went all the way up to his thighs. When all this was on, she clapped her hands together. "Hmmm, looks great," she said. "Let's take some pictures just like this."

He sighed. So it begins.

He posed in front of a camera that she had set up on a tripod in the center of the room, her standing behind it, taking pictures, giving instructions. "Now just stand there looking bashful, yeah, like you're already doing, perfect. Now, pose with one hand covering your chest, the other hand covering your crotch, like you're embarrassed to be seen in your underwear. Open your mouth wide, like you're in shock. No, wider. There we go. Now, give me a kissy face. Come on. Come on, Dyl, kissy face. Haha, perfect. Now turn sideways and stick your ass out. Put a hand on your ass. Finger on your lips. There we go. Alright, I think it's time to put you in your dress."

The dress was this antiquated frilly thing, pastel pink with white lace trimming, wide skirt at the bottom, big bow around the waist, smaller bows decorating it throughout. As soon as Rose put it on him, he felt ridiculous wearing it, like some frivolous daughter of privilege a hundred years ago, fluffy and useless.

Rose then sat him down in a wooden chair and crouched down to start doing his makeup. He found it hard to sit still through this, everything seemed to tickle, and he made her screw up his eye makeup a few times with his inability to hold his eyelids steady. He couldn't ignore the feeling that this was wrong, he was a boy, shouldn't have any of this stuff on. Every instinct in his body told him to get out of here, get away from this situation. But he knew he couldn't, knew she'd release the video if he did. God, he felt so helpless, like, well, a little girl made to dress up all cutesy at the whims of the grownups.

At last Rose seemed to be done. She took a step back, admiring her handiwork. "God, you look so pretty, you know that?"

"Stop it," he sulked.

"Ohhhhh poor baby. You do look pretty, be happy about it." She handed him a hand mirror. "Take a look."

He did look strikingly like a girl, he thought miserably, albeit with short hair. Mascara on his eyelashes, rouge on his cheeks, bright pink lips... God.

Rose giggled. "So cute. Really like playing dress up with you. You're like my little doll." A spark seemed to light in her brain. "Hey, maybe that can be your name: Dolly."

He groaned, "Nooooo."

"Yes, that's perfect. Come on Dolly, get in front of the camera again."

He sighed and trudged over.

"Hey, back up straight. Now, give us a smile. A real smile, Dolly. Good girl. Now a twirl. Nice, nice. Now give me some sassy. Hip cocked, finger on your chin. There we go, nice." She pressed some buttons on the camera and stepped away from it. "You're really a natural at this, you know that?"

"If you say so," Dylan said, sulkily.

"C'mon, you can enjoy it a little," Rose said. She dragged the wooden chair directly in front of the camera and sat on it. "Now, I've got it recording video. We're going to get some footage where you're sitting on my lap."

He blinked. "You're joking."

"Why would I be joking?" She seemed a little impatient now, which made Dylan nervous. "Come on, make me happy sweetie."

Reluctantly, he sat down on her lap. Immediately, she wrapped her arms around his waist, holding him in place. "There's my Dolly," she said, her head on his shoulder.

"Stop calling me that," he grumbled.

"Hmmm, I can call you what I want to, Dolly," she said.

"What is this for, anyway?" he asked.

"Don't think that's any of your business. Smile for the camera. Show them how happy you are to be on Mama's lap."

He attempted to smile, but mostly just gave a grimace. Rose didn't seem to notice. She gave him a kiss on the cheek. And another. And another.

And it was nuts, he hated Rose, but the feeling of her lips on his cheek was getting his cock harder underneath all the frills.

"Alright," Dylan said, "this is getting too sexual."

"What are you talking about," Rose said, and planted another kiss on his cheek, "kisses on the cheek, very chaste."

"This whole thing is... I don't know, some fetish degenerate freak shit," Dylan said.

Her grip on his body tightened. In a low growl, she said, "You'd do well not to insult me."

He sighed. "Just don't want to be unfaithful to my girlfriend, is all. It's starting to feel like that's the direction it's going."

"Alright, if that's what's most important to you, I guess I'll let you go," she said, and removed her arms from his waist. But just as he moved to get up, she added, "Of course, if you leave it does mean you've reneged on our little deal, so I'll be forced to release the clip of us. But if what you care about most is your girlfriend, I'm sure you wouldn't mind."

He sighed. God, he didn't want the other brothers to see, but... if Kim saw him cumming from a cock up his ass, probably she'd see him as a fag, or at least a submissive, and she wouldn't be able to respect him, and he'd probably lose her anyway. He slumped against Rose's body.

"Let's just finish the shoot, fuck it," he said.

"Hmmm, that was the smart choice," she said, and wrapped her arms back around his waist. "I'll let you in on a secret," she said, then dropped to a whisper, "I wasn't about to let you leave." Kiss, this time on the neck. "I was about to release the clip though. You're a smart girl after all, made the smart decision."

"Stop calling me a girl."

Kiss. "No." Another kiss. Then a nibble. Then a harder bite that made him go "Ah!"

Alright, this was sexual. Despite himself, he was rock hard by now. Wasn't really visible given how big the skirt was, but if she moved her hands even slightly from where they were, he knew she'd be able to feel it.

Now she clamped her lips on the skin of his neck and sucked, hard, so hard it felt like a bite. He felt as the blood vessels tore under his skin. She released the bit of skin she was sucking and ran her tongue over it. "Just wanted to leave you something to remember me by."

Goddammit, he thought, people are going to see that hickey. He'd have to avoid Kim until he could get it to clear up.

"Now, Dolly, sweetheart," she said, moving a hand up to stroke the back of his hair, "give us a kiss for the camera."

He hesitated for a moment. Well, he was in it this deep, just go with it until this is over. He turned his head over and moved his lips in toward her mouth...

"On the cheek, Dolly," she said with a grin. She turned her cheek toward him. "You little slut, so eager aren't you."

He rolled his eyes and planted a kiss on her cheek. He pulled his lips away and noticed that he had left a perfect pink lipstick mark on her cheek where he'd kissed it.

Huh. He sat there staring at it. His lips had done that. Huh. It made him feel... huh.

"Another," Rose said, low commanding voice.

He planted a second kiss on her cheek.

"Keep going..."

A third. A fourth. He was about to kiss her cheek a fifth time when she turned her head around to catch his lips against hers.

God, despite everything, he couldn't resist his biology, and the second Rose's lips touched his he felt a lightning bolt hit his brain. She kept kissing him, and he kept kissing her back. Her tongue teased at his lips, and without him even really choosing to, his lips opened to receive her tongue. His tongue met hers, feeling each other, tasting each other. She pulled her lips away but kept her tongue against his, their tongues still playing with each other outside of their mouths. When her tongue finally separated from his, a strand of saliva ran between them.

All of this on video, he remembered, goddammit.

She looked at him, eyes burning with lust, feral hunger. "You want me, don't you?" she breathed.

He looked away, "I... I don't know what I want."

"Oh, poor confused Dolly," she said in a soft mocking tone. Her hand went down to his crotch and, through the dress, grabbed at his cock. He inhaled sharply when her hand made contact with it. "Seems like your body knows what it wants."

"S-stop it!" he said. "I don't want that."

Her hand descended his cock, just a fraction of an inch, and involuntarily he thrusted upward into her motion. She raised her eyebrows at him, gave him a smug, knowing look.

"You horny little thing," she said, "you've put in quite the dilemma. God, it would be so wrong to enable you in betraying your little girlfriend, but..." she gave his cock a twist, milking a little "Ah!" noise from his lips, "it wouldn't be right to get you so hard and just leave you hanging." She sighed dramatically. "Oh well. Guess I've gotta finish you off."

"I, ahhh, I can't consent to this," he gasped.

She smirked, and gave his nose a little nibble. "You won't have to. Just one thing though."

A quick flurry of movement and Dylan was thrown over the bed, stomach down, legs hanging over the side. Rose turned the camera to capture him in his new position.

"If I'm gonna make you cum, I'm going to have to insist you let me cum... inside you," she said, grinning cruelly at him.

"No!" He moved to get up, but soon enough she was right behind him, holding his body down against the bed.

"Come on, baby, I'll make it good for you. Well, sort of. I'll make you cum for sure." She reached down underneath the dress and put both hands on the frilly panties until they ripped apart. He felt a lubed finger running along his exposed ass crack. He shuddered.

The lubed finger was soon replaced with a lubed cock, massive and throbbing, running along his crack, teasing him with the inevitability of intrusion. "Mmmm, now feel how hard you've made me Dolly. It's only right that we take care of each other, don't you think?"

In a small voice, Dylan just said, "Please..."

Rose looked up to grin into the camera. "Listen to her, she's begging for it!"

And with that she started plunging her cock into him.

Dylan grunted. With actual lube, her cock was sliding in much more easily than it had the first time, but still going in too fast, stretching him too much. He tried to move away from it, but Rose just grabbed his shoulders and held him in place.

In a deep growl she said, "Don't try to get away from it, you're going to have to take it all baby. Bite the bedsheets if it helps."

He felt bad taking her instructions, but he still bit down on the sheet.

She slid her cock out a little and dealt him a hard, punishing thrust back in. He let out a broken, "Ah! Ah! Ah!" through his gritted teeth.

"Mmmm, yeah baby, make those noises for Mama," she growled. Another rough thrust, another, "Ah!" Then another, then another...

Brutal thrust followed brutal thrust. His asshole was on fire, yet he couldn't help but notice how much smoother, wetter it felt than last time. The way it rubbed pleasurably against some part of his insides was more distinct this time. His cock, treasonously, remained rock hard, grinding against the side of the bed, leaking precum all over the inside of the dress.

As she kept fucking him, he felt her hands grip hard on the back of the collar of the dress. It began to rip apart down the center, exposing the flesh of his back. "Hmmm look at that skinny little body," she moaned, and dug her fingernails into the flesh of his back, running them down his spine, leaving long scratches. "You play like you're such a big clever man, don't you, but the truth is you're this scrawny little thing. You were built to be somebody's bitch. You're lucky I found you. Aren't you?" He said nothing. She yanked on Dylan's hair. "AREN'T YOU?!"

"Ah! Yes!" he gasped, desperately.

"Yes what?"

"Yes Mistress!" God, the words she said made him feel so small and pathetic, agreeing with them made it worse. And yet... he could hear in the moans he was making as she fucked him, he sounded like a whore, sounded like he was enjoying it. And on some level he must have been enjoying it, because even without any stimulation on his cock, he could feel himself getting closer, closer...

"Ah! Ahhhh cumming!" he moaned as cum shot out of him, splashed all over the inside of the dress.

"Hmmm, got you bitch," Rose said with satisfaction. "Now it's my turn."

He remembered from last time how much worse it got after he came; at once, his sphincter felt so tight, so dry, so tender, but she showed his hole no mercy. He struggled against her, to no avail, she was strong enough to hold him in place easily.

"You know, I never got to cum inside you last time," she said, "been really looking forward to it."

Right now, the thought of her cumming inside him felt so degrading, he couldn't bear it. "No, no don't."

Rose, of course, always liked to hear a boy telling her "no" when he was powerless to stop it. She looked down at her conquest, tattered dress, scratched up back, his ass so tight on her cock. She felt drunk on the power she had over him. She'd fucked most of the fight out of him, she could tell, but it would be hot if he were still struggling under her... maybe she could say something to mess with him, find a little more fight in him.

"Aww, why don't you want my cum?" she asked, smirking, "Is it that you heard about what futa cum does to a boy?"

Dylan seemed startled. "N-no. What? What does it do?"

Got him, she thought. "Oh, once a futanari cums in your ass, it slowly turns you into a complete sissy slut. You start to crave girly clothes, makeup, feeling pretty. And of course, you crave more futa cock, can't help wanting it again," hard thrust into him, "and again," thrust, "and again."

"Nooooo, no, please don't," he groaned, and struggled, thrashed and writhed under her, but he couldn't escape, couldn't get away, couldn't stop her.

"Eh heh heh, you're mine you little bitch. Mine! Ohhhhh FUCK!"

She didn't have to say it, he knew she was cumming. It came with a series of deep, hard, convulsive thrusts into his body, he could feel her cock throbbing as she shot cum deep into his intestines.

When she was finished he lay there twitching beneath her. Cock still buried inside him, she leaned down, gave him a kiss on the cheek. "You know that was really good for me baby." She nuzzled her nose against his face. "Really looking forward to next week."

He felt his heart sink. "Next week?"

"Well yeah," she said, "this is gonna be a weekly thing for us now, me dressing you up and taking pictures. Doesn't that sound fun?"

"No..." but he felt his cock starting to rise at the thought, no no, stop it stop it.

"No?" she said. "Do you want me to release one of the clips of you getting fucked? Is that really how you want it baby?"

"N-no..."

"Are you sure?" she stroked his hair, "Hmmm, I'm sure all the boys in your frat will be lining up to fuck you once they see how good you take cock. Is that what you want, baby? I can make sure they all see it."

"No, no," he sighed, defeated. "I'll be here."

"Hmmm, good girl," she said, and kissed his cheek again. A little throb of his cock when her lips touched him. "Now that I've cum in you, you're mine forever, you know that? You can fuck that little girlfriend of yours all you want, but we'll both know you're really mine."

She pulled her cock out and got off him. All at once, he felt a huge amount of cum gush out of him. God, his asshole felt so wide, so busted open.

He glanced behind him. Rose was lounging in the wooden chair on her phone, no pants on. "You're free to go Dolly."

"Stop calling me Dolly," he grumbled.

"No."

Sigh. Why did he even bother? "Can I use your shower?"

She perked up. "Hell yeah, I'd love to shower with you baby!"

"No, no, just... by myself."

She shook her head, "Oh no, I can't allow that. What if you steal my soaps?"

He sighed. Alright, gotta sneak into the frat house somehow without being seen all covered in makeup. Goddamn it.

He lay there on the bed in the remains of the dress. The fabric of the dress was soft, he had to admit, softer than his own clothes. Softness was nice right now. The air was thick with the smell of her, every time he inhaled he got a big whiff. He couldn't deny he liked the smell.

Did he find it so hard to start getting out of here just because he was tired, beaten down? Or did he want to stay here, linger in this moment, just a little longer?

He honestly couldn't tell. But he wasn't in any hurry to get up.

TO BE CONTINUED