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Chapter 20
by
Tunathetitan
Now for the rest of the night
A glimpse at fate
You take your clothes off and grab the lube from her palm. Applying it to your ass she then holds the plug up so you can lube it. Once it's prepped she has you turn around before having it go right up. More things that wouldn't have been suspected before today. You didn't realize but your sister had also changed clothes. Wearing now a lovely purple lace bra with thigh high stockings and crotch-less panties she gets off her bed. Her cock dangling idlely. It seems as though the site of you putting in the plug didn't even phase her.
"Great, now that is temporary," she says with a grin. "now go stand over there Let's do some measurements." She points to a more open part of her room where she will be able to maneuver around you. She walks over to you with her fabric tape measure and begins measuring your chest, neck, arms, eventually moving down. As she is doing the measures she is just occasionally moving intimately close, breathing against your neck. Biting your ear, pinching your nipple, teasing you so slightly. Moving down she measures your thighs, calves, inseam. Being that she is kneeling around you again, she breaths against your cock, a lick occasionally. Slowly you become erect. "Well now that that is up, time for some fun." Moving to your other side to ensure your measurements are equal she starts breathing against your rear, prodding the plug. Letting out a slight moan she gets up and walks away. Leaving you to your devices.
"Are you gonna just stand there or are you gonna come over here and look at this shit." She says now laying down in bed. She pulls up her laptop and pats a spot next to her. Sitting next to her you see the familiar website layout where you found the ring. However instead of rings it's their home page, with TONS of ads for dildos, lingerie. "So I pulled up a few items that I saw that I liked but if anything speaks to you just say so." Looking up you see she already has a few items in her cart. You really wanna know what she has in there but don't want to outright ask. She pulls up the clothing section and just starts clicking through. You see stockings, collars, all sorts of things you would see in victoria's secret ads except even more racy. While clicking through she uses her other hand to rub over your skin. She shifts so that her waist is rubbing up against yours. You can feel her cock resting against your hip. You begin to get distracted, as one of your hands goes down to her waist. She guides your wrist over to her pussy. She leans over "play with my clit, then we'll get started." Without hesitation you move your middle finger over to her hood, slowly rotating clockwise her clit. you already can feel her cock getting hard.
Before long it is straining against you. "Alright. Time to get to work." She pulls herself up to where she is sitting up. Legs crisscrossed. Her cock in perfect view. "Well I didn't think I'd have to prompt you." Just as quickly as she said it you sprawl as you attempt to begin devouring her member. At the first lick you are reminded about why you are putting up with the shopping, the plan during dinner, all of it. She isn't even wearing the ring. It's still on her neck. While tounging her head you look up and see she is looking over to the side. Her laptop still open. She is using her hand to complete a transaction. Looking over you try to glimpse as to what she is buying. "Nice try slut, get back to work. Here I'll give you what you want for putting up with looking at clothes with me. Soon you may actually say something and want some of those clothes." You despise how confident she is in saying that. Never the less she wraps up her transaction. Closes her laptop. And undoes her necklace. Grabbing a ring she uses her other hand to pull you off of her so she can slide it down. Nothing changes. Her cock doesn't stiffen harder. Grow longer. It's the same. But now you know what will happen when she comes. And it turns you on even more. Your cock bursting like a fire hydrant waiting to unleash the torrent. "Be lucky tomorrow is sheet and bedding day."
Before long you can tell she is getting close. But before she can finish she rips your skull off of her. "Now as much as your skill has improved. And as hot as it was to watch you struggle with keeping me lodged in your throat. It's time for the main attraction." She grabs your skull and pushes it into the bed. You feel her move a hand down to your ass, fresh with lube she starts to twist and turn the plug out. You don't even feel it slide out due to the well lubrication. You feel her put her weight on your back. She whispers into your ear "Are you ready? From here. You. Are. Mine". You haven't even had her cum. You have only tasted her raw cock. No intoxication. No nectar. You still have a degree of levelheadedness. A part of you is eager to descend. To fall into a pit of pleasure, with no end in sight. Another begs for you to run. To get away. To go back to your room lock your door. Avoid any temptation that comes your way. The withdrawals can't be that bad. You can get over this addiction.
But before you can make a decision. It's too late. Her weight shifts back. Her warmth penetrates. Before long a sensation unlike anything you have ever felt envelops you. A warmth that grows and grows filling you to completion. A wave of heat comes over you she sits full length buried in you. "Wow, no wonder guys always want anal from girls. Well I suppose the shoe is on the other foot now. Or rather, the ring is on he other cock. Now come on, let's see this baby in action." She begins sliding in and out. In and out. Before long the she is thrusting non stop. Before long she is on the edge again. As are you. "Mmmmm, I could get used to this. Oh wait, because I have the ring on. I can." Bemused you can feel her pulsing. "Here it comes. And this won't be the only one tonight." And you thought her first penetration was electric. Any and all thought you had. Any concept of true bliss. Gone, her cum shooting into you is like being branded. A broken man you have become. A scar ripping through you. But with sheer pleasure. Not an ounce of pain. Meanwhile you can feel your cum as an after thought. The only thing that told you it was happening was you felt some spread against your wrist. After waves come down. And the two of you have been removed from one another. Laying face down. Your stomach sitting in your cum. Hers leaking from your ass.
"Roll over." She commands. Rolling over your cock sits flaccid. "I want more. I'm gonna fuck your brains out. Once I grow tired I'll move you back to your bed. Then tomorrow we will discuss the future. You can only hear a few of the words. Your mind still in the cloud of your recent encounter. You feel her grab your waist and position herself for more. You really are a sleeve for her now.
After a night of non stop usage
Magic Cock Ring
A Magic Portal for your Genitals
A Magic Cock Ring story inspired by Swallows 999
Updated on Dec 24, 2025
by Avalon_Imperative
Created on Feb 5, 2017
by AnonySD
You can customize this story. Simply enter the following details about the main characters.
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