She wins you over

You stand there, stunned at what she has just told you, the feelings overwhelming you. Your sister offered to suck you off. A few weeks ago, you would never have believed it, but with how things are progressing so far, you know she isn't lying. But for her to do it, you will have to wear her plug. Sure, you've thought about it before, even probed yourself with a finger once, but the sensation was too much for you, so you stopped, repressed it from your memory. You are not gay. You have always told yourself you are not gay. Straight people don't put stuff up their ass. But these last few weeks, Emily has pushed you further and further. She has not only gotten you to wear a cage, she has got you wearing her clothes. Dresses, skirts and stockings. And now she has shaved you. And you already have long hair. From a distance, someone could easily mistake you for a girl. And girls can put things up their ass.

Suddenly, you feel Emily's hand on your hard cock. You shiver at her touch. "It seems like someone liked my suggestion" she says, gesturing at your hardness. She starts gently stroking it, as a moan escapes your lips. "Come on John. If you think it's too much, I can go first. I'll show you." She takes one of the plugs out of the box and seductively puts it in her mouth, wettening it, before she hands it over to you. "Now put this in me." she says assertively.

Emily bends over in front of you, a sight that you don't think you can ever get enough of. Your cock feels harder than ever as you see her lower lips part as she widens her stance. She gets down on all fours, with her ass pushing up towards you. Her pussy is glistening, you are unsure if its from the wetness of the shower, or out of pure lust. It's probably a combination of both. And her tight asshole is right above it, mesmerizing you. "Put a finger in John." she says, inviting you to something you never would have thought had been possible, even in your wildest dreams. But you won't let this moment go to waste, as you gently push one of your digits inside her butt.

You expected it to be tighter than her pussy, but you can feel her muscles grip your finger as you push deeper into her. You can only imagine how tight your own hole must be. But you push those thoughts out of your mind for now, as you start fingering your sisters asshole. She responds with a soft moan as you push your finger in and out of her. "Another one John.." she pants. "I can take two..." You decide not to question these gifts she gives you, as you push yet another finger into her hole. This time, her moans get more audible. Your cock is aching, leaking precum, as you start fingerfucking your sister. But your pleasure is nothing compared to what she is feeling. She has moved one hand to her pussy, and is furiously rubbing her clit. "Faster John. Fuck me faster!" she moans. "Fuck your sisters tight asshole John!" She is clearly getting into it, as you keep up the pace. You will do anything for Emily, and helping her cum is one of the best feelings in the world.

"Put some fingers into my cunt! Fast!" your sister pants. Her breaths are rapid, and you know it's not long before she will climax. You move your other hand to her pussy, and push two fingers in there. The angle is quite awkward for you, but you are determined to make your sister cum. You push two fingers into each of her holes, until suddenly you feel her entire body quake. "Fuck John, I'm gonna fucking cum! Your sister is gonna fucking cum for you! Fuuuck....!" The sensation of your sisters ring muscle contracting on your fingers is the best feeling you've ever had. You are in heaven. You cock twitches as your sister rides out her orgasm on your fingers. Her screams echo throughout the bathroom, loud enough to be heard all over the house. Good thing you two are alone.

Your sister is lying on the bathroom floor, sweaty, naked and panting. You watch as her breasts rise and fall with each breath she takes. Her pussy is glistening with juices. You stand there, naked as day, hard as you have ever been. You want nothing more than to lay on top of her, pushing your hardness deep into her. But you would never do that. Not without your sisters permission. She turns around and looks you in the eyes, with a warm smile.

"I love you."

"I love you too Emily." You reply. These last few weeks have really brought you two closer. Your reply is as earnest as her statement. You know it without a doubt. You stay looking at each other for a long while, and you feel nothing but happiness. You know that your sister feels the same. Then, after a while, she picks up the plug that you seem to both have forgotten. "Now put this in me sweetie. And then we'll do you."

You are suddenly reminded of why you are here. And what she is demanding of you. You take the plug up, looking at it closely. Its has a cute pink crystal at the bottom of the grip. It will match your cage, you realize. It then widens. At its widest, it's slightly larger than the two fingers you just put in her. You hold it for a while, feeling its thickness. You wonder if there's any way that this will fit in you. Emily is lying on the bathroom floor on her back, legs pushed up. Her pussy is dripping, and her butt is gaped a bit from the fingerfucking you just gave it. You push the plug against her ass, and Emily is shivering as the cold metal of the plug meets her skin. As you push it into her, it goes in with relative ease, until it bottoms out at the grip. You wonder if it will be as easy for you. "I've missed this." Emily moans, as you fill her with the toy. "Now it's your turn John. Get on all fours!"

You hesitate once again. If you do this, you will definitely have crossed a line. But you don't wanna disappoint Emily. But you know your sister only wants the best for you. Your sister loves you. And you love her. She has pushed you beyond what you thought was possible these last few weeks, absolutely. But at the same time, these previous weeks have been the best ones in your life. So what's to say that this won't be equally incredible. You decide to trust you sister. You know she would never hurt you. Your sister wants you to put a plug in your ass. So you will obey her.

Girls can put things up their ass after all.