Rescued by Miss Senna

Riley nodded. He'd been made to wear women's clothes, before; Kay used to love to call him all kinds of names when she'd dress him up. If not for the name-calling, Riley wouldn't have minded so much.

Senna kissed his cheek and left the room, coming back with a pair of soft cotton panties in a pastel pink. She slipped them up Riley's legs and lifted him up to pull them up over his butt. They were comfortable, and held his small cock well.

"You look pretty," she said, and Riley shivered. That--that wasn't something he was used to being called. "We'll get you some new clothes tomorrow if you're up for it, but these will do for the night."

With that, she picked Riley up and carried him off to her bedroom, laying him down on one side of her bed. She pulled on a pair of green panties, then, and eased off her wig, setting it on its foam cap before she started her evening skincare routine. Several minutes later, and Senna had her satin cap pulled on--mint green with elegant little patterns on top--and had finished brushing her wig as well.

When she climbed into bed, Riley was still awake, if just barely. He looked over to her and asked, "Is this... what it's supposed to be like?"

Senna paused. She thought the question over and shrugged. "I think there's not much of a 'supposed to' to it. I think there's some people who might've even enjoyed what Kay--what she's like. But even that needs--you have to talk about it, you know? Even if that was something you wanted, there'd still have to be conversations. But if this feels good to you? Then, yeah. This is what it's supposed to be like."

Riley mulled it over, and might've said more if he hadn't drifted off mid-thought. The day had worn on him and when he felt Senna pull him in close he felt warm and safe against her body, and sleep wasn't something he could dodge any longer.

Senna followed shortly thereafter, holding Riley like a teddy against her chest as sleep wrapped around them both.

--

The next few days, Riley was quiet. Senna didn't push him; she knew he'd been through a lot, though perhaps not the full extent of it. She brought him meals and let him rest, and in the evenings she bathed him and held him close.

On the fifth morning, though, Senna woke Riley up at ten. She brought a plate of food--toast with butter and jam, and chicken sausages, and savory oatmeal with a fried egg on top, and fresh orange juice--and set it on the bedside table before climbing into bed beside Riley, pulling him in to kiss his brow.

"Rye?" She started, feeling him wake slowly. He blinked up at her and wrapped his arms around her body as best he could, clinging to her in his sleepy state. She hugged him back, pressing a kiss to the top of his head.

"Hey, baby boy," she cooed, rubbing his back slowly. "I know you haven't felt up to going out, but we've got somewhere to be, today. Can I get you to come out with me in an hour?"

He nodded slowly, though she could see the reticence in his movements. "If you're good while we're out, I'll give you a reward when we get home." He looked up at her, curiosity in his eyes. "Nope--it's a surprise. You'll have to be good to find out what it is."

Riley slowly let go of her, sitting up and looking over to his food. He mouthed a "thank you," though no sound came out, and slowly picked at his food as Senna got up.

"You'll have to wear some of Anne's clothes," Senna said, going to where she had her ex's things. "I'm sorry, baby--I know it's probably uncomfortable."

Shrugging, Riley took a bite of oatmeal and egg. He didn't mind so much--not when Senna never said anything bad about him when he wore them.

She found a t-shirt and hoodie of her own--well fitted on her, but they would be baggy on Riley--and a pair of leggings for him to wear along with a pair of flip flops. It would be comfortable, at least, and she hoped it wouldn't feel too awful gender-wise.

Riley let Senna move him around, getting him dressed as he ate, and soon he was ready to go. He carried his dishes down to the kitchen, setting them in the sink to soak while Senna finished getting herself dressed, and then they were out the door.

The cool air felt comforting against Riley's face, and Senna led him to the car and buckled him in before getting in the driver's side and starting them off.

The building they pulled up to was large and beige, a product of the seventies, and inside they went up to the eighth floor and into a small psychiatric office. Senna had called the first day Riley had been with her, scheduling an appointment for him, and had struck luck when she was able to set up something quickly. Riley was a bit surprised to be where he was, but he didn't protest, and when the time for his appointment came he followed the therapist mutely into a back room.

It had taken some time to work out how to communicate, but his therapist was patient and kind and she let him write his thoughts out when it became too difficult to speak. The hour went by quickly, and at the end she gave him a journal and told him to write in it every day about anything that crossed his mind. Senna set another appointment for the next week, and they left.

In the car, she buckled him in and when she sat beside him, she took one of his hands in her own. "Hey, Rye?" She started, catching the boy's attention. "I just want you to know it's gonna be okay. You--I know you've been through some really messed up stuff, and if you don't want to submit to me you don't have to. I don't mind letting you live with me either way. I just want to help you, and--"

"No," Riley said, his voice hoarse. He looked worried, and Senna paused to let him find his words. It took a few moments, before he pulled out the little journal the therapist had given him and jotted something down. When he showed her, it said, "If I was left in charge of me, I wouldn't do anything. I need help. I need someone to be in charge. Please don't stop."

She nodded. "Of course, Rye--I just wanted you to know that it's not something I'm gonna force on you. I want you to want this, too."

He scribbled again, then held it up. "I do. If it's you, I want it."

Senna felt her chest warm at that, and she took his hand once more to press a kiss across his knuckles. "Okay. That's all I needed to know."

With that, they drove home. As curious as Riley was about his reward, he was half-asleep by the time they got there, emotionally exhausted from speaking with his therapist, and Senna helped him get to bed before tucking him in for a nap.

It was an hour and a half later that she came into the bedroom, stripping herself naked before climbing into bed beside Riley, getting close enough to him to pull him up against her. Riley stirred, finding his face pressed against her soft breasts and letting out a quiet, happy sound as he breathed in her soft scent, peaches and brown sugar.

"Hey, baby boy," Senna cooed, feeling Riley press closer to her. "How are you holding up?"

He shrugged his shoulders, nuzzling his face against her as he felt his cock start to stir. It had been a few days since he'd cum in Senna's hand, sitting on the bathroom counter after being rescued. And with the food he'd been eating lately--rich vegetables and fish and chicken, sweet and salty and savory things, wheaty breads and coconut milk--his body had the energy to feel as needy as his mind did.

Senna felt a pressure shift against her hip, feeling Riley's cock hardening, and she smiled; it looked like he was enjoying his reward. She moved to shift one large breast, lining her nipple up with Riley's mouth. "Open up for me, Rye," she said, tone gentle but firm.

Eagerly, Riley opened his mouth, stomach fluttering when Senna pressed her warm nipple into it. She had bathed recently, and he could taste the lingering sweetness of the sugar scrub she'd used.

He sucked at her skin, tentatively bringing one hand up to help hold her breast in place, and as he did he felt his small cock reach its full hardness. It twitched against Senna's hip, and he looked pleadingly up at her, not wanting to let go of her breast just yet.

Senna moved her hand once Riley was able to hold her securely, trailing manicured fingers slowly down his body. He hadn't worn anything to bed, and she took advantage of that, pinching one small, pink nipple, rolling it between her fingers as Riley moaned against her breast.

"Someone was a very good boy, today," she purred, and she felt it when Riley shivered against her. It still felt so new, being praised; he couldn't get enough of it. "And I do remember making a promise. So I've got an important question to ask you, and if you can manage a verbal answer I'll be very proud of you. If not, just hold up your fingers. One for the first, two for the second, three for the third, okay?"

He nodded. His voice felt heavy, but he wanted so badly to make her proud. Riley told himself he'd find a way to make himself speak; he could do this.

"Your reward is a big, messy orgasm," Senna explained, feeling Riley's cock throb once more against her hip. "But you have to decide where you want to have it. You could cum in my mouth, or on my tits, or in my pussy. The third would make me happiest, but there's no penalty for choosing the first or second."

Riley froze. Kay's words flitted though his head, and Senna could feel him tremble as he pulled his mouth off her breast. For a few moments, he opened and closed his mouth, trying to get his words out, and Senna waited patiently.

"You... you won't feel it," he said, voice soft and sad as he ducked his head. Kay had always said his cock was too small to use; she never even called it that. "I--I have a useless clit, a g-gross worm--"

"No you don't," Senna interrupted, letting go of his nipple to cup Riley's face. Her eyes were bright in anger, but she didn't let it touch her tone; she wouldn't scare Riley.

She turned his head with her hand, making him look at her face as she spoke. "Riley, you're not hers anymore. You're mine. That means your body--and by extension, your cock--is mine, and what's mine is good. What's mine is wonderful. I don't own anything that isn't exactly what I want, so if you're mine, then you're perfect for me. Understood?"

There were tears, now, slipping down his cheeks, wetting his pillow and her hand as he sniffled and watched her with such intensity. He wanted to believe her so, so badly. "But what if--what if I put it in and it's too small? What if I can't be good for you?"

"You can. You can, because I say you can. You asked me to be in charge," she said, pressing her brow against his own, "and I am, but that means you have to let me help you get rid of everything that was hers, okay? Because this--this cock? This cock is my cock, and my cock is perfect."

Riley felt butterflies swarm in his stomach as she spoke, chest fluttering to look into her deep, dark eyes, and he saw a future in her arms. One where he was--body and soul--hers, and in that he felt himself rising out of Kay's clutches, felt her chains falling off his body, off his mind.

He nodded.

Wordlessly, Senna kissed him, claiming his lips as her own and holding him tightly against her body. Riley yielded, letting her explore him willingly, wanting to give her anything--anything he could. She touched his chest, his hips, his ass and felt his cock regaining what hardness it had lost, and she smiled.

Pulling back from him, she asked once more, "Do you want to cum in my mouth, on my tits, or in my pussy, Rye?"

And Riley, with all the conviction he could muster, setting his fears at Senna's feet and trusting her even when he didn't trust himself, said, "Please, Senna, let me cum in your pussy."

In a smooth, fluid movement, Senna pulled Riley on top of her, rolling herself onto her back to let the boy settle between her strong thighs. Her soft breasts jiggled a moment as the two of them settled, but she didn't stay still for long.

"I want you in me," she said, reaching down to guide his cock toward her wet, soft pussy. "I want to feel my cock in me."

Riley shivered when his soft, spongey head pressed to her puffy lips, letting out a whimper when she slipped him in further. Senna's cunt was overwhelmingly hot, and her soft, bumpy texture was only amplified by how wet she was. His hips stuttered forward, pushing in until they were pressed tightly together, and he steeled himself as he looked up at her.

Her head was pressed back into the pillow, an ecstatic look pressed into the corners of her lips, into the tightness of her eyes, and Riley felt so sure of her; he had trusted Senna, and seeing her like this--he knew this was where he belonged.

"Rye," she breathed, feeling her cunt pulse and twitch around his cock; she had been so ready to fake her pleasure for him, wanting him to feel like his cock was good, but this... Small as he was, his cock curved just right, the ridge of his head sitting in the perfect spot to send sparks through her body. She wouldn't have to fake this. "Move for me, baby boy."

He did, and she tensed her pussy as he slowly pulled out, letting go as he thrust back in. Riley shivered and trembled; she felt so good around him, gripping him gently, then tightly, then gently again, and he couldn't stop the gasps and whimpers he made each time he pushed into her, each time his cock head caught at her entrance.

Senna gripped one of her large tits, pinching her nipple as she moaned. "Oh, Riley--oh, fuck..." she breathed, feeling his cock rub against something that sent a shiver through her body, had her cunt tightening around him. "Fuck, baby boy, right there."

Her encouragements were more than he could handle, and after only a few thrusts he could feel his balls starting to pull up. Riley gripped at Senna's thick thighs, whining, "Oh, no--no, Senna, I'm gonna--"

"It's okay," she soothed, reaching her free hand down to stroke her aching clit. "Cum for me, Rye! I want it! I want to feel your cum in me..."

It was too much. Riley tried his best to hold back, tried to force his cock not to cum, yet, but Senna's pussy was so hot and so wet and gripped him so tight and his eyes were squeezing shut he felt his cum shooting up his cock, forcing open his piss slit to coat Senna's insides with shot after shot of hot, thick cum.

He kept thrusting, shaking through his orgasm, and wanting so badly to make Senna feel good, too. He knew she hadn't cum, though she'd said it was okay, but it wasn't. Not for him.

Panting as he slowly opened his eyes, he could see Senna's hair strewn about on the pillow as she stroked her clit, and he swallowed hard.

"Good boy, Rye," she praised, seeing him all flushed with the intensity of his orgasm; hers wasn't far away. She could feel his cum inside her, and even the thought of it had her edging closer to climax. "Good, good boy--you put so much cum in me."

"W-wait," he pleaded, and Senna paused her stroking as she looked up at him. "I want... Please, can I make you feel good?"

"Baby boy..." Senna purred, feeling him slowly pulling out of her. "You made me feel so good--look at how close you got me. I'm so close to cumming, Rye."

"I know--and I don't feel bad," he assured, leaving just the head of his cock in her as it slowly softened. "But I want to make you cum. Please, Senna, will you let me?"

"Baby... Okay. Show me what you can do."

It was all the permission he needed. With a quick motion, he pulled the tip of his cock out and laid on his tummy on the bed, face between Senna's legs. He'd eaten pussy plenty of times; Kay had always wanted him to eat her cunt after she'd been fucked by one of her boy toys. But he'd never wanted to so badly as he did, now.

He pressed his face against her pussy like he was dying, like he was desperate, like he needed it, and Senna squealed when he started to suck his own cum out of her, feeling it slide down his throat smoothly. She tasted so sweet and good, and he felt her pussy convulse against his face, clit throbbing against his nose as she came--but Riley wasn't finished.

Senna's toes curled as she gripped at the bedsheets, feeling herself nearly black out for how powerfully she came. He was so good, so good to her needy cunt. When he clamped his mouth around her clit, she howled. He rutted his tongue against the sensitive underside, relaxing and then pointing it up, pushing two fingers into her cunt to rub against the spot his cock had filled, and when he felt her cum a second time he finally let her go, pressing one last, soft kiss to the top of her mound before shyly looking up at her.

Her hair was disheveled, clinging in sweaty curls to her face and neck, and her chest heaved as she slowly caught her breath. Looking down at Riley, she reached for him. "Come here, baby boy," she puffed, watching him move to lie next to her.

"Uh-uh," she said. Pulling him up on top of her got a little squeak out of him, and she kissed him deeply as she held him. "Just here. Like this. I--we should clean up, and we will in a minute, but..."

Trailing off, she saw a sparkle in his eyes she hadn't seen once since she'd brought him home, and it filled her heart with such warmth she felt like she could live in this moment.

"Just let me hold you, okay? You're so good--such a good, good boy--and I just want to hold you."

Riley purred when she started to pet his back, laying his head on one large, warm breast as he wrapped his arms around her as best he could. "I... I feel like a good boy. If I'm your boy, then I think that might... might make me a good boy," he admitted, something tentative and scared in his voice.

"It does," she answered, feeling him slacken against her. "It does, Rye. It makes you my good boy."