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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James disconnected the laptop from the TV and rolled his reward. Looking over to him, Myles trembled with fear. He looked to Sienna, and spotted the lust in her eyes. The excitement. She grabbed his hand.
"Is this how you feel every single day, sissy toy? Fuck, I could get addicted to submission."
The result of the roll wasn't anything special, but James opted not to tell Sienna anyway.
"Myles, put some music on to make your sister more comfortable."
"Why?" Sienna asked. Myles began to do as he was told, changing the channel on the TV to a music channel blasting out the Christmas classics. James approached Sienna, and the worry set in. "James, why?"
Still, he did not answer. Sienna backed up against the kitchen counter and had nowhere else to go. There she stood, in just her bra and panties, so small in the shadow of James' silhouette and his big dick reaching out towards her.
Myles quickly returned to his side, hoping that today would finally be the day that Sienna would let him watch her get fucked. The fog had left his mind, his orgasm, forced out of him with only a tiny amount of stimulation, actually felt satisfying unlike those that came with none. His balls were still full and sensitive, but he felt a little bit more in control of himself. And he wanted that gone, he wanted his sister and his best friend to tease him until he was a shaking mess longing for more torture.
James forced Sienna around and bent her over the counter for a mirror image of how she first saw him fucking her sissy brother. James slapped her arse hard and slid a thumb underneath her panties and pressed it against her arsehole.
"Wait! Stop!" She cried out. She squirmed to try and get away but James held her there.
"That's so cute. You're just an anal virgin. Want me to make your first time special? Want me to be gentle, little girl?" James asked in a mocking tone.
"Don't tease me!" She groaned.
"Unfortunately, Sienna, you lost the game so I get my reward. You can't back out now."
"Ugh. Fine. But I want a lot of lube." She grabbed a bottle Myles had left on there from earlier when he prepared himself to take James' cock, and passed it to James.
"Ugh. Fine." He jested back at her. "Myles, hop up on the counter and lay down. Sienna, get on top of him, he'll show you how to take a dick up your butt."
Sienna didn't really like giving her brother this much stimulation, having to press her entire body up against him as she laid atop him. They could taste each other's breath and Sienna smiled. If she was to get anything out of this, it would be how horny it would make Myles. From here, she didn't have to tell him not to look, he would be able to see her little pink arsehole demolished by James' meaty spear.
James lubed up his cock and then squeezed out a blob onto his fingers. Myles watched Sienna's face sour as James pressed his fingers up against her arsehole. Myles used his legs to pin hers in the correct position and spread her hole as much as possible.
Sienna bit down into her lip as James pressed the thick head of his cock against her arsehole and began to push. With great hesitation, the hole began to accept him. But a pained scream formed in Sienna's mouth. She threw her head back in a cry for help. Myles grabbed at her waist to try and comfort her, but it didn't work. More drastic measures were called for, James knew, so he reached out and pushed her by the head, forcing her head back down and her lips against her brother's.
She kissed her brother on the lips for the first time, and kept kissing as James forced the whole length of his cock into her arse. When his balls pressed against her cleft of Venus, she pried her soft lips off of her sissy.
"That all you got? I thought you were supposed to be a real man?" She giggled, and James tensed his cock causing her to squirm. She promptly shut her mouth.
"Keep kissing Myles. Let him make you feel good."
Sienna put her hand against Myles cheek as they continued kissing. At the same time, James pulled his cock back, and thrust only a little way. A few more thrusts showed Sienna how fun this could be, and the three got into a rhythm.
Each wet squelch into Sienna's tight arse made Myles' cock shudder. His heart beat to the same pace, and he felt his sister's tongue paw at his lips, asking him to open wide and meet it with his own.
First base. It occurred to Myles then that Sienna was the first girl he had ever kissed romantically. And for her to find him worthy of her tongue, he felt blessed indeed to have earned so much of her affection.
James needed extra force to stand a chance at cumming. After two orgasms that day, he needed more force. He got rough with Sienna, spanked her arse, reached around and massaged her clitoris, his hand also brushing up against Myles' cage and earning pleasant hums from the slave.
Sienna's voice also hitched as she shuddered through a powerful climax delivered through jolts in her clit. The dick in her arse, the fingers on her clit, and the tormented sissy slave underneath her was all so perfect. It was an orgasm like no other, one that she never thought she'd have.
Slapping sounds excited each of them when James made good pace, stretching out Sienna's hungry arse with each thrust. It kept her on the edge and unable to come down from her last orgasm. All three of them loved this situation. Sienna loved getting to kiss the boy she treasured while being filled by the man she lusted. James loved fucking this sexy babe and getting to be the bull for his best friend locked in a tiny, humiliating cage. And Myles loved being locked in chastity forever and watching the girl most precious to him be manhandled by another.
Sienna screamed through a second orgasm, and her trembling body was stimulation enough for James to fire whatever cum he had left into her sticky, creamy arse. The brother and sister were left on the table, while Sienna tried to catch her breath. Through high-pitched, heavy breathing, she occasionally managed a couple of giggles.
"Miss Sienna? Did you enjoy that?"
"Fuck yeah, I did..." That was all she could manage to get out of her mouth. James pulled her panties back over her arsehole, and lifted her off of her brother.
"Come on, let's get you onto the settee."
"I don't want this to end." She muttered.
"Wh-What if we wear our matching vibrators, Miss Sienna?"
"That's my sissy toy. That's a great idea. Good boy. Go get them."
The three spent hours that day watching Christmas movies, with Sienna idly buzzing the vibrator inside her, blissfully ignorant of just how much it made Myles struggle. She had her focus on the big-dicked man she lay against, her other hand fondling him and stroking him as she wished.
That night, she scurried off to bed with James, leaving Myles to sleep in his own bed, with his ear pressed up against the wall dying to hear them go at it.
Sienna lay atop James under the covers. They kissed and kissed, and he explored her curves with his hands.
"I hope I made you feel welcome today." Sienna pulled her lips off of his long enough to say it. And then pressed her forehead down against his to rest herself. Their lips lingered only millimetres apart. And they gazed lovingly into each other's eyes.
