One Step Too Far

"That's it baby," growled Jeremy. "You're a natural cock whore wanting to throat fuck me! Damn!"

Len started squirming on the bed, the bondage and lingerie ramping up his arousal even further.

"I can't let this go to waste," said Beth, pulling her panties off from under her skirt and climbing on the bed to straddle Len's waist. He almost lost his mind when he felt her pussy slide down his cock. His squirming let him thrust a little as he sucked Jeremy's cock with abandon.

Len had never sucked more than a dildo in real life. On the sissy forums he'd sucked cock hundreds of times and he did his best to bring all his imagined talents into play.

"Oh fuck he's a sweet little cock sucker!" growled Jeremy. "Does he swallow?"

Rach had sat down again. "She'd better," was her only response.

Beth was grinding down, taking his whole cock and moaning softly. Len could see her out of the corner of his eye, another fantasy come to life. More flashes, more pictures.

"Moan if you're thrilled to be a sissy little cocksucker," asked Lisa as she shot video of him sucking cock. Len moaned loudly and then felt splashes of cum erupt from Jeremy's cock. Len was so eager that he sucked and swallowed like a pro. When Jeremy finally pulled back, his cock left Len's mouth with a pop.

His attention focused on Beth, the super curvy cocoa-skinned goddess riding his cock. She was stroking her clit as she rode him up and down. He soon started thrusting eagerly and she let him, holding herself up a half foot from his waist.

"Oh Jesus!" blurted Beth and then Len felt her cumming. He thrust and held there, suddenly overtaken by a wave of orgasm and pumping her with cum. Her thighs and pussy were already smashed into his cum from before.

Beth also eventually dismounted but not before leaning down so he could feel her heavy breasts on him and giving him a passionate kiss.

"Oh yeah, he's a keeper," she said, trying to straighten her outfit and stand steady.

"Yea, I want to try some of that soon," purred Jeremy, zipping up his jeans.

"OH that's just great for you horn-dogs!" whined Rachel. "What about me?" Len could tell that she was aroused and squirming on her seat.

"One last talent to test," suggested Lisa. "Here..." Lisa blindfolded Rachel with a pair of satin panties and then led her to the bed.

"He's my brother, or my sister or whatever," protested Rachel, softly.

"Pretend he's me," whispered Lisa, getting intimately close to Len's sister. "Remember last weekend? You liked that a lot..." She kissed Rachel's cheek a few times and then their mouths met and Len watched his sister make out with another girl. Lisa cut it short and helped Rachel take her jeans and panties off. Then she helped her get on the bed and straddle Len's head.

"She's just a sissy girl. I bet she loves to lick pussy..." encouraged Lisa as she gently sat Rachel down on Len's face.

A day from explosive pleasure to abject terror to fantasies coming true made Len's mind swirl. But the thought of licking his sister's pussy had him rock hard in the panties. He eagerly leaned up to tongue her. Her pussy was very hot and wet, a testament to how much his sister was aroused by the whole situation. He couldn't see but felt like Lisa was kissing Rachel and stroking her breasts through her shirt.

It took a minute but Rach finally started using Len, putting her pussy exactly where she wanted him to lick, to probe, to flick and suck. He went into it eagerly, never imagining he'd be allowed to taste his sister's pussy, never like this. His cock was rock hard again.

"You told me last weekend," began Lisa softly, very close to Rachel's ear as they grabbed a kiss here and there. "All about wishing Len was your sister instead of your brother. How sisters could explore things and talk to each other about desires. How you confessed that you'd masturbated to the thought of feeling your brother's cock inside you..." With that, Lisa gently helped Rachel lift up from Len's mouth and move down, finally aiming his cock directly for her pussy.

"You've wanted this forever... feel your brother's cock..." Lisa instructed and Rachel reached under her to grasp and fondle Len's cock. He moaned and strained in the chains and his elaborate sissy outfit. "Feel how good it feels in you..." pushed Lisa further and Rachel bit her lip before sinking down onto Len's cock.

He closed his eyes, anxiously absorbing every sensation, every tight, wet, hot feeling of finally having his cock in Rachel's pussy. Then he looked up and watched as his sister started to ride his cock. She was staring at him, her face glazed with desire.

"That's right... fuck your brother," growled Lisa and Len saw her touching her own pussy. "It's so wrong, so taboo. Unforgiveable but you want it, you need his cock, you need him to cum deep in you!" Rachel's face was shocked for a moment at the mention of cum but she didn't miss a beat as she moved up and down his cock, slowly increasing speed. "That's right.. the whole fantasy... riding his cock and feeling his cum fill you inside... taking that risk with your own brother..."

Rachel was riding faster now, Lisa's words obviously getting her more and more excited. "You can get his cock any time you want now... he's your sissy sister and would do anything for you... you can suck him while he's wearing the sissy maid outfit you're going to make him wear to do house chores, risking if your parents come home and discover him... You can bring him into your bed at night like you told me you wanted... fucking your brother all night long... you can lock him in his sissy girl clothes any time, anywhere... but his cock is yours... yours to fuck... yours to suck... his cum is yours... when you feel fertile..."

"Oh god yes," whined Rachel, slapping up and down on his cock as fast as she could. When Lisa reached in to rub her clit, Rachel screamed and came. Len held his cock up inside her and felt his balls clench.

"I'm cumming!" he moaned in a girlish voice and he felt spurts of cum erupt deep in his sister's pussy as it grabbed and clamped down on his flesh over and over again. Rachel held on to Lisa as she rode her orgasm and Len saw his cum ooze out around his cock, knowing he'd really filled her up. She laid down on his chest, his cock still deep inside her and stayed there until her body settled and his cock softened and slid out of her.

"Sweet Jesus," laughed Jeremy. "We are one fucked up little family, aren't we." The tension was broken as everyone succumbed to laughter for a moment.

"So, Rach, what are you going to do with him... I mean her now?" asked Beth. Len laid there, the room hot and full of the smell of sex, his cock worn out and his balls aching. He pulled enough on the chains to make them clink.

"May I be released?" he asked his sister. She lifted her head and looked at him with a questioning look. He finally added, "... Mistress?"

"Yes, I think that is appropriate, sissy. You won't forget that you are completely in my control that way. You may only call me Rachel when we're with Mom and Dad." She propped herself up on his chest, her pussy sliding against his flaccid cock. "Things aren't ever going to be the same, are they sissy?"

"No, Mistress," he said quickly struggling to hide his grin.