Crystal and Her Sissy Brother (Worm)

Felt like writing a thing or two for Locktober.

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Discovery for a sissy still in the closet almost always is a horrifying experience. There is first the shock of someone walking in during their private time. Usually as they are masturbating, so there is a sudden rush as fight or flight takes over. Then there is the horror, a deeper kind than just someone accidentally walking in while they are jerking it, though often there is that too. Doubly so if it’s while having some anal fun. Then there is the embarrassment of being caught, of a family or friend seeing how much of a degenerate the sissy is. All of these culminated into one as the door was bashed open and Eric Pelham, also known as the teenage hero Shielder, froze as suddenly his sister there. She could see everything, there was nothing that he could hide from her. She could see his pink chastity cage, the cheap pink lingerie he was wearing, the ballgag in his mouth, the collar that said sissy bitch, and the dildo he’d been bouncing on in his lust. 

I’m fucked, was all he could think as the sissy porn played in front of him, as a metronome beat into his ear, with his sister there, standing in the door way. 

Then he noticed something on his sister. Something long, thick, and hanging from her hips. The hero looked to his sister, and he felt a shock go through his core, his ass clenching around his dildo as he saw the strap on, hanging from her waist. Slowly he looked up, and saw Crystal was almost completely naked except for the strap on, and a smug smile adorning her face. Seeing his expression, Crystal giggled as she sauntered in, her hips swaying too and fro, a hand pushing the door shut as she walked up to her brother. Once more, Eric had no idea how to respond other than whimper as she got closer to him. Crystal meanwhile put a hand on her brother’s head, and petted it like was her pet.

“Poor Erica, all locked up,” she said, her grin turning into an almost sympathetic smile. She looked to Eric’s tv and saw the kind of porn he was watching, and she was close enough to hear the metronome, and could see the indicator of a dildo on the screen to show when to bounce on the dildo he had. As she saw this, her smile turned to a grin.

“Oh what a good sissy slut you are Erica, training your ass,” as Crystal said this, her hands cupped Eric’s balls, giving them a light squeeze as she felt his cage. “But I think I got a better idea, pause it and then get on all fours.”

Holy shit this can’t be happening, Eric thought as he followed his sister’s instructions, got on all fours and reached for the remote almost too quickly as he nearly smacked the remote away. It was only his forcefield that stopped the remote from being pushed out of reach. As he did so, Eric couldn’t keep his breath calm. This… this was like something out of a lewd fantasy, something that one read about and jerked off to online. Already his heart was beating faster, his caged cock twitching as he paused the video. Crystal meanwhile had stood up straight, only to move behind him. He heard her kick his dildo away, leaving only her behind him, her and her strap on. Then she fell upon him, her body pressing into his, her breasts pressing into his back. Eric’s cock twitched again in its cage, his ass clenched a bit, almost trying to suck something in as his hips kept shaking with each small twitch. One hand though reached up, and pulled off Eric’s ball gag, letting it fall to the floor.

“Not ready for the ball gag yet, maybe when we can trust each other more,” she said, and Eric nodded. As he did so, Crystal grabbed the remote before pulling back, while her other hand started to slid around Eric’s ass. Eric tensed up as she did so, not sure how to react to her touch. Where ever she touched from her breasts against his back for a brief moment to her hand, it was like a fire was blooming across his skin. Her fingers especially as she slid them between his legs, stroking his thighs, making him twitch as she teased him. It was pushing his heart into his throat and, making him short of breath. At the same time, he felt his sister’s strap on smacking the top of his ass as he waited on all fours. He could feel her dildo was already lubed up, and so was his ass. 

“Are you ready?” she asked, and Eric had to swallow before he could answer. 

“Yes…”

“Yes what?”

“Yes Mistress,” as he said it, for some reason he only got harder in the cage he was using, his ass clenched a bit, and he had to take a shuddering breath. He could feel himself nearly start to drool as his blood continued to try to rush to his loins. Even though he’d said it so many times in front of a hypno, for some reason, this time there was a reaction, this time, as he was bent over ready to have his sister of all people take him, it aroused him more than anything else ever had.

“Mmmmh, good Erica, now lets get ready you ready, was there a pause before this?” she asked, and Eric nodded.

“Uh, a minute back… Mistress,” he said, dropping his head, and yet his blush must be nuclear as Crystal giggled before rubbing his butt again.

“Such a good girl,” Crystal said, and Eric smiled, a swell of happiness entering him that he almost worried that Vicky had entered the room. 

Is this what having a mistress is like? He wondered as Crystal scrolled back a bit, before finding the area where there was a pause.

“Now I hope you’re ready, because we’re about to have some fun,” she said then started the video.

The beat started off slow. Just another warm up. The previous section had been slow too, but now it was going to speed up, by quite a lot. Eric’s breath was already haggard and breathy with anticipation, his caged cock hard as could be, and his ass practically begged for cock. 

The first thrust was delicious. A sensual sensation was sent through Eric’s ass, the strap on his sister had filled him up as she slid into him for the first beat. Eric let out a breathy squeek as the faux cock slid across his prostate. Her dildo was far larger than his. His was only just bigger than his usual cock, while hers, hers was probably modeled after some porn star, the thing was thick and almost as long as his forearm. 

“You like that sissy?” Crystal asked, and Eric nodded, before responding:

“Yes- yes Mistress~!” he said, barely able to catch his breath, a smile spreading across his face. Already his clitty twitched in its cage, he could feel a bit of pre already starting to drip from it. This couldn’t be real, and yet, it was. The second beat came, and once more Crystal slid into his ass, the cock once more pressing into his prostate, fireworks of pleasure being sent off into his mind as Eric swallowed again to keep from drooling. 

As the video went on however, Crystal sped up with it. The speed increases were rapid, going from a single slow thrust in to a sudden burst of rapid fucking. Crystal thrust into her brother as fast as the video asked. Pleasure sparked as they continued with each round, his sister thrusting into his core, filling his ass with her cock as Eric at first tried to hide his moaning before giving up. Soon enough his moans filled the room as he let out little high pitched squeaks with each thrust. He felt a bit of pressure behind his cock at the same time as she thrust, her toy filling him and making him feel better than the first time he’d actually hit his p-spot. 

By accident, Eric fell, his hands slipping on the carpet as his sister kept pounding away at him. His chest hit the floor, but as he tried to get up, he felt the tell tale force field of his sister pressing into his back, keeping him there.

“I think I like this better, stay like this my slutty sissy sister,” she said, and then as she did, she shifted back there. Eric didn’t look away, but when the next wave of thrusts came, she started thrusting down straight into his prostate, the thrusts long and powerful. Despite himself he moaned louder than any of the other times, and with a twitch of his clit, he felt a small spurt of pre spill out from his dick as she finished the wave. 

“Holy…” Eric said, and then he started to recognise the coming part. It was the final wave of this section, a long, drawn out series of rapid fire fucking that went on for at least two minutes. Eric’s breath came out faster, he swallowed again as more drool came. This was it. As the last wave of this section came, Eric tried to prepare himself, but as Crystal slammed down into his ass, he cried out again, pleasure erupting from his p-spot as Crystal pounded his poor pecker with her faux phallus. She slammed into him easily, and must have been throwing her weight in with it as each slam of her cock nearly drove Eric into the ground. Eric’s eyes rolled up and his mouth hung open. Drool finally slipped form his mouth as he continued to moan while his sister continued to thrust. The pressure behind his cock started to increase more and more, a little bit extra with each thrust. Meanwhile Eric’s cock twitched and bounced, pre dripping and flying all over as Crystal fucked his ass. 

Then Eric’s eyes widened as his pleasure peaked, and then went even farther, pushing him into nirvana. Somehow, the climax of pleasure and wondrous sensation bloomed from his ass, making his hips and torso shake. His head vibrated as his face contorted into an expression of agonising pleasure. His whole body started to shift and shudder from the feeling. Eric’s dick felt more incredible than anything he’d ever done while his ass was the centerpiece of sensation as Crystal’s thrusts grew more powerful with each thrust. With each pound it was like a climax was firing off from his ass and enveloping his whole body in pleasure. Eric’s focus drifted away from everything else, the pleasure he was feeling the only thing he could focus on as Crystal fucked him more and more while he felt something dribbling from his cock the whole time. At some point Crystal’s fingers holding his hips slid down and one warm hand wrapped around his cage, fondling his balls and giving them a squeeze, before she pulled her hand up and brought them to his mouth. Without hesitation as they were brought to his face, Eric started to lick and suckle at her fingers, and a salty sensation spread through his mouth as Eric greedily slurped up his own cum, moaning as he did so.

Then with a final thrust Crystal drove her whole dildo into Eric one last time, before leaving it there, and falling heavily to her knees. Meanwhile Eric was a wreck. He literally slid off his sister’s dildo, his caged dick landing in something wet as Eric lay there, unable to move, a happy grin on his face as he lay there. He heard Crystal giggle at him but he paid her no mind, his head still clouded with a lustful fog. However, he started to come to when Crystal slid up onto him, her naked breasts pressing into the pink body sock he’d slipped on. 

“Bet you liked that didn’t you?” she asked, and eventually Eric answer.

“Yeah… wow… I… I sissygasmed,” and Crystal giggled to his response. 

“Well I’m glad I could give it to you, so… staying locked up all October right?” she asked, and Eric nodded as best he could on the ground.

“Good, but just to make sure, I’ll need to see those keys of yours, just to make sure you stay locked like a good sissy,” she said and Eric couldn’t be happier. 

While discovery was usually terrifying, it looks like he’d managed to luck out.
 
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