AI image by ZenCreator — Craig as Cassandra with A Dildo Up His Ass — by Z

Craig — Crossdressed As Cassandra — Tucked & Tortured By His Step-Sister Cassie And Her BF Riley

“How Are You So Sure He Didn’t Want A Dildo Up His Ass?”

Cassie and Riley have yet to re-enter Craig’s special private bondage cellar, but their conversation about his cross-dressed bondage predicament is clearly finding its way to his ears…

“The garters and fishnets were a very good choice, Riley. They almost make Craig, I mean, Cassadra’s legs look sexy.”

“Enough, Cassie! I’m talking about the dildo up his ass. How are you so sure he’s not liking it?”

“He seemed pretty upset when I suggested it, and fought it for a while.”

“Just like he fought the tighter dress, the silver-fox-wig, us threatening to rope him so tight that he ends up with tiny titties,” pointing in through the doorway, “And yet, LOOK!”

Cassie replies, “Yes, eventually, we forced him to do every one of those things, but he complained at every step of the way.”

“You’re not getting it. He wants this! He’s craving this! And we just served it up to him, so he can sit there, squirm, and enjoy every second, while we do all the work!”

“Riley, I love and respect your thoughts and ideas, but he’s embarrassed as hell, and now that we have pics of him doing this to himself, he has to do whatever we want.”

“You think he’s helpless, and that we’re in charge? He’s the one in charge here, unless we step it up… a lot!”

“Wait, let’s just ask him. He’s our prisoner… he needs to answer.”

AI image by ZenCreator — Craig as Cassandra Interragation Time! — by Z

Everything Riley is saying is fucking spot on. Yes, he’s embarrassed as all hell for getting caught, and knowing they have pictures of him as Cassandra… well… he’d actually like copies. But Cassie is vindictive, so if she knows how much he’s loving this, they will stop, or do something way worse!

With the single light over his head, and Good Cunt / Bad Cunt, at his sides, Craig’s cross-dressed, tucked, and dildo’d interrogation starts in full force.

Riley, aka Bad Cunt, starts out with, “Tell her! Tell your stepsister you’re loving this, Sissy!”

Craig stares off between the two, trying to ignore the touch of their hands on his naked and cold flesh.

Cassie, obviously, Good Cunt, calmly asks, “Is this embarrassing you, Craig? Having us find you cross-dressed, as we keep you captive?”

“Of course he’s not embarrassed! He wants this!”

“Is what we’re doing to you, a punishment, Craig?”

Again, he looks off into the distance, counting the spider webs he’s yet to knock down, because he never expected company in his private cellar.

AI image by ZenCreator — Craig as Cassandra Interragation Time! — by Z

Raising her voice, Riley snaps, “Do you like it? Sissy? Big hard dildo up your ass, as you squirm and wiggle? Do ya? DO YA? DO YA?!?!? SISSY!!!!”

“Tell Riley you don’t like having that up your ass, Craig. Just shake your head no, so we can tell.”

“ARE YOU TUCKED AGAIN, SISSY? TINY LITTLE COCK, ALL TUCKED AWAY AND USELESS, WITH ZERO CHANCE OF GETTING INTO OUR MOUTHS, OR OUR PUSSIES? POOR SISSY BABY!”

Now Cassie raises her voice, but not at Craig. She raises it at Riley, “He’s my brother! His cock isn’t going into any of my holes!”

“Step-brother, and as big a slut as you are, Cassie, you’d let him fuck you, if he wasn’t such a tucked sissy.”

“Are you sorry for taking my panties, Craig?”

“How many pairs you got holding your tiny beast back this time, Sissy? More than five?”

Craig, in an effort to become the smoothest crotched version of Cassandra, is wearing six pairs of extra-tight panties.

AI image by ZenCreator — Craig as Cassandra Interragation Time! — by Z

With the ropes on his chest pulled as tightly as they are, Craig has a tiny pair of titties, so they decide to check them out.

“Why are your nipples so fucking hard, Sissy? Are you excited, Sissy?”

“Tell me you’re not liking this, Craig, that you want us to stop.”

He does nothing. No nods, no head shakes, and still no eye contact with either of them.

Riley pinches his nipple as hard as she can, which finally gets a grunt, and several jerks out of their new sissy toy. As much as he loves being tucked, he’s craving the ability to cum, or try to get the dildo at least a tiny bit out of his ass.

They catch him squirming and randomly lifting and adjusting his legs.

“Oh no, you don’t, Sissy!” Turning to Cassie, Riley asks, “Do you see any more rope?”

“Right over here. He has a box full of it,” replies Cassie, returning with a bundle for Craig’s ankles, which she starts to bind without thought or further direction.

AI image by ZenCreator — More Bondage — by Z

Riley asks, “Did you say there was a box full of rope?”

“Yes,” knowing where this is about to go, Cassie happily adds, “Yes, I did.”

“Well, since this Sissy won’t talk, I say we tie the fuck out of him, and leave him to think about how badly he’s behaving, until he decides to be polite.”

AI image by ZenCreator — More Bondage — by Z

Cassie asks, as she’s already adding more ropes, “How long do you think that’ll take, Riley?”

Riley, also adding rope, “As stubborn as this sissy is, at least all night long.”

Craig starts to struggle and grunt, but it’s not going over too well.

AI image by ZenCreator — Even More Bondage — by Z

“Knock it the fuck off, Sissy! This is on you!”

Cassie adds, “You should have just answered us earlier, Craig.”

He tries to answer now, but it’s too late!

They continue their relentless roping of Craig’s already helplessly bound, cross-dressed body! The ropes across his lap cause the dildo to push further inside of him in the most painful of ways.

AI image by ZenCreator — Yet Even More Bondage — by Z

Riley can see how the ropes on his lap are causing him pain, so she adds a few more, while laughing at his pain.

Patting him on the shoulder, Riley says, “I’d tell you to have a nice night’s sleep, but know there’s no way you’re gonna be able to sleep. So instead, I’ll just say, you know you’re loving this sissy, especially that dildo up your ass.”

Craig is now struggling like crazy, but there’s not a chance in hell of his getting loose. Riley runs her fingers around on the top of his lap, commenting, “Too bad it’s tucked away… I would have happily made you cum.”

Cassie, concerned, asks, “Should we turn the lights off, or leave them on?”

Turning to Craig, Riley says, “All he has to do is admit he’s loving this, and we can leave the lights on, so he can watch himself struggle in the mirror… all… night… long.”

Cassie asks, “Craig? Are you loving this?”

He hesitates, then finally shakes his head yes. Followed by turning his head to view Cassandra’s bound body in the mirror, just as Cassie and Riley head towards the door. Riley, just before passing through the doorway, flips off the lights switch and then loudly slamming the door closed…