Sissy for Sister Ch. 08

Author's Note: This is a fictional story about a brother and sister relationship featuring gentle female domination over a crossdressing brother with gay sex and chastity. Since each chapter may contain content that falls under different categories, please refer to the 'Story Tags' tab under 'Story Info' for a list of categories this chapter includes.

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Again, Myles got so close to watching his sister get fucked only to be denied. She allowed him to hold her by the waist while James drilled into her wet, slobbering pussy long and hard. Myles held her, but with strict instructions not to move his hands from her hips. Naughty images flashed through his head of what this might have looked like, Sienna's perfect and perky breasts, small to fit her frame, but not so small that a real man like James wouldn't have found himself stunned by their perfection. He imagined she kept her pussy perfectly waxed and eagerly swallowing James' thick shaft with every mighty thrust. He leaked while they went at it. His sister's soft moans drove him crazy.

James had perhaps been a bit reckless, grabbing at Sienna and forcing her down on the stairs. So she got Myles to sit on the step and hold her. He didn't need to keep his eyes shut, she'd put her panties over his head as a blindfold. And pulled off her T-shirt. He could feel her breath strain out with each thrust. Little droplets assaulted him with each wet and hot breath forced out of his sister. Myles hadn't been offered to kiss her, but he began to hump the air, possessed by a tremendous sexual energy he could hardly contain.

So he leaned in and began to kiss at Sienna's chest. His chin ran against her soft skin slick with sweat. And by chance, he traced the rim of the left cup of her bra.

"Feeling naughty?" Sienna teased. She watched her brother hump the air and kiss her chest with a huge grin on her face. She placed her hands over his on her hips and ran up his arms to his shoulders. And rested her hands there. Likewise, she could feel James' straining breath against her back. Each thrust, he slammed his balls off of her and vanished his cock into her welcoming hole.

Each thrust, Sienna could only keep the same thought in her head: That they were made for each other. Not just the two of them, but the three.

She was close to orgasm. An incredible pressure built up from her core and spread out through her body to every extremity, made her feel hot all over and at one with James. His orgasm was looming as well, she could feel it. One hand around her stomach pulled her in closer, and the other around her neck made every inch of his rod that slid in and out feel like ten. Twice every second, she was taking all seven inches of his cock. All seventy as she imagined it.

Her breathing hitched, her back arched, and her fingers dug into Myles' shoulders. She cried out in pleasure, while James simultaneously fired his load inside her. She collapsed onto her brother, and giggled weakly while she regained her breath.

"That was incredible as always, James."

"I couldn't resist you." He too collapsed onto the stairs and took a seat. Sienna glanced down, and slyly smiled at James' cum dribbling out of her and onto her brother's lap.

"Eyes closed." She ordered Myles. She pulled the panties off of his head, wiped up James' cum, and then put them back onto Myles' head. The incredible smell made him ooze more pre-cum. Sienna watched him writhe helplessly and smiled sweetly. He was so desperate and would have done anything she told him, or said anything, for even a faint chance to cum.

Her hand went to her pussy and began to stroke. James got onto his knees, took another step closer, and pushed a finger up against her arsehole and worked it in. He leaned in and past her, so he could see her flush face loving every bit of attention she got. Those wet eyes glanced his way, and he wanted her again already.

And then she glanced down, and her head hung. Her nipples were just about poking through her bra. And Myles' hands trembled against her. With James' other hand, he reached under her bra and cupped her breast, squeezed and played with it. It was firm, yet soft, and so very warm. Each squeeze and tug he gave it shook her to the core. But he didn't relent, he grabbed at it rougly, tugged and teased her nipple. Sienna's moans came randomly, between strained breaths and moments where she wrestled to maintain her composure. But it was no use, a finger on her clitoris, a finger in her arse and a hand around her breast harmonised into the perfect tease, and she couldn't last long. Already, she felt another edge upon her.

"Oh, fuck." She moaned. A devious idea crossed her mind then, though she had no idea how well it would play out in reality. "He's going to make me cum again, sissy toy. This is so unfair."

"Unfair?" James barked. He let out a chuckle at the absurdity. Especially with the irony of Sienna saying that to her chaste slave.

"Yes, unfair. It makes me feel so submissive to you. It makes me want to beg to be your cute little girlfriend now and your sweet waifu one day. When you make me cum, it just makes me want to toss aside this small dick loser and pledge my eternal love to you and you alone."

Myles breathing hitched. And Sienna smirked.

"Are you actually about to cum to this? To me telling another man I love him more than you? I know that you're a low-testosterone submissive without a Daddy, but whatever happened to the boy who cried after I made him have an orgasm in public?"

"I... Miss Sienna, I'm so close. P-Please may I cum?"

"No. You can't. You're still on cooldown after kissing me. I'll tell you when you can cum. And that's. Not. Yet." She lilted. And giggled. James plunged his finger deeper into her arse and she quivered. Whatever dominant illusion she could concoct could so easily be shattered by James' domineering confidence. And she knew he wouldn't be the only one who could reveal her true nature.

"Maybe I ought to take a page from your book, Sienna. If you're in charge of Myles' orgasms, perhaps I should put myself in charge of yours."

"You're delusional!" She jabbed. But she melted to James' touch. He wasn't letting up, she knew she'd cum in a matter of moments.

"Cum for me, little girl." His low voice, barely a whisper, sounded so sinister. But the look he gave her finished Sienna. She screamed out again, and collapsed against her brother. Her head rested on his shoulder. For her, the day seemed at an end. James gave her a soft slap against the cheek.

"Stay awake. Come on."

James forced her from the loving but timid embrace of her brother and down a few steps. He placed her in front of his cock, getting hard again. And she began to lick at it, still dazed. James watched her and smiled. There was nothing quite like a sexy girl working her magic. Sure, perhaps Sienna's magic wasn't quite as potent as her brother's; Sienna wasn't as good at sucking cock as Myles was, but even Rose couldn't match the beauty of Sienna fresh from her climax.

He pressed his hand against Sienna's head, urged her to get the entire length into her mouth and take it nice and easy. But he felt she was onto something teasing her brother so cruelly, and looked up to his best friend still sat with those panties over his face, locked in lust, fidgeting despondently.

"Your girlfriend really is just a submissive little thing, Myles. But not to you. She dominates you. She submits to a real man. You could have her lips around your cock right now, but instead you're just taking in a lungful of another man's cum. She finds it exhausting to dominate you, she confided in me. She didn't think she could tell you because you lack that masculine energy. Women don't look at you and think: 'There's someone I can settle down with and start a family with'."

Coming out of her stupor, Sienna looked up at James with wide eyes. Pleading eyes. She didn't know what he was playing at, but so casually admitting what she had told him in secret was a painful blow.

"Honestly, cuck, you don't deserve her. She needs to be with someone who takes command and lets her live the way she's truly happy. I was kidding when I told you I might just steal her away from you, but now I'm thinking I'll actually do it. What do you think? Hell, I might even ask her to come back to uni with me to let you feel the pain of being abandoned by your sibling."

"James..." Myles whined. He felt his tears swelling up. A little more of this and he'd sob. He could only hope that his best friend would stop it soon. This was all going so much further than he was comfortable with.

"Yeah, this babe needs a real man. I think I will take her."

Sienna pulled her mouth off his cock, and glanced up to Myles. She could tell how close he was to breaking from his body language. A fun game arousing him had vanished, that arousal lost to the pain in his chest. It had slipped and fallen away into that endless pit in his stomach dragging his whole mind down into endless despair. Even his small penis, so swollen in his cage moments prior from coping with a forbidden erection, now looked so snug and comfy.

Sienna hated to hear this drivel too. Her heart just about cracked. And she looked back to James, ready to defend her boyfriend, but the plain the expression on his face confounded her. How could he not feel anything saying something so horrible to his best friend? She wondered for a minute, and their eyes lingering on each other conveyed their feelings as well as words could have. And a smirk crept back into her.

"Go on, sissy toy. Beg him to steal me away from you?"

"M-Miss Sienna?"

"Don't you think I'll be happier with a real man? He's right, you know--it's exhausting having to be the man in our relationship. It doesn't leave me with any time or energy to be a girl. I wish you were the kind of man I could confide in, the kind of boyfriend I could trust to take some of the weight off of my shoulders when I need to relax. But you're not."

"And you're never going to be." James interjected.

"So let's just cut this whole charade. Beg James to steal me away from you."

"James... W-Would you..." Myles voice trembled like crazy. He had no clue how he could possibly ask this. He didn't know whether it was James that had dissolved the love Sienna had for him, or whether it was fake to begin with. As his tears escaped into Sienna's soft panties, he hoped perhaps she'd let him keep them as a memento of their time together. That small possibility was the only he felt strong enough to ask:

"James. Would you please steal Sienna from me and make her happy in all the ways I would never have been able to?"

James and Sienna kept their eyes on each other.

"Yeah, you wanna try that again, bud?"

Myles braced himself to try again with an even more pathetic request.

"Mister James. My cock is too small to ever..."

And Sienna cleared her throat loudly.

"Maybe instead of willingly giving me up, you could try telling me that I can confide in you in the future?"

"Miss Sienna, if that's what you want, I will. I'll change in whatever ways I need to, to make you happy. I love you, if you ever need to get something off your chest, I'm here for you."

"Everything I said about you is true. I'm not asking to change our relationship, because I do love dominating you. But it does exhaust me, and sometimes I need you to just take control and take me for dinner or a movie or out on a walk. Even if you need to dress as Rose to do it."

"Yeah, I can do that. I'll take you both out for dinner tonight."

"Good boy." Sienna had this huge and perfect smile, James reached for the panties on Myles' head.

"Close your eyes." He demanded. He gave Sienna her panties back, so she could put them on and her boyfriend could see the elation she wore openly. James' eyes met Sienna's again, and once again they conveyed their feelings without words. He was quite the remarkable man to help her so thoroughly. A good friend, and the perfect bull. Sienna continued sucking his meaty cock, and enticed Myles over to help her out.