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Chapter 40 by Wolf Keeper
Watching her get fucked
First fuck experimentation
With you sitting on the bed unable to use your hands, you have **** but to watch as Jane picks up the two black dildos and places them next to you. She then attaches the 6 inch one that comes with it, that is the same size as you, onto the machine. Plugging in her phone to a charger, she opens the app and gets it paired. You see her set the depth to it's shallowest thrust, and the speed to slowest. Angling the machine so that it'll fuck her while she's on all fours in front of it. She backs up until the tip of the dildo is pressed against her pussy.
"Okay, time to test this out. Best to start with the minimal settings and then ramp up. After all, if I break it in for us, then we can make sure it gives us both a proper fuck. An with you having a pussy between your legs. It's the only way I'm going to get a proper fuck, tonight at least."
You hear the machine click to life, and slowly thrust forward. Slowly spreading your wifes pussy lips, it goes in smoothly about 5 inches before backing up. Jane stops it when it's full extended again, and backs up to fully insert the dildo. You notice that now she's backed up, she's aligned with the ankle cuffs attached to the machine. Though you do remember they can be moved further away from it. Starting the thrusting back up, it's going just a bit fast than before. It's at this point you feel that panty vibe come to life against your clit. The vibrations are enough to give you some pleasure from it, and your clitty is trying to get hard. However, with it trapped, it's fighting a losing battle.
"Well this is certainly a new experience for sure. While it doesn't have the same sensual feeling of making love to you my lovely Mary. The relentless fucking it is giving could make a woman give up men."
Laughing to herself as she says this, she speeds up the machine to start fucking her as hard and as fast as you can. With her thrusting herself back you can tell she's getting into the continuous fucking the machine is giving her. Letting out a slight moan from the fucking she's getting, you hear the motor kick up in noise as it starts to go faster with it's thrusts. No longer is it a casual gentle fuck, it's now at a decent hard fuck pace. You also can see that the 7 inch dildo is going fully inside wifes pussy, before it gets pulled out until the head is just barely inside her. This goes on for about 20 minutes, as she increases the speed to where it's certainly faster than your hips can thrust. After at least 2 orgasms and another 20 minutes of the machine fucking your wife hard, she stops it. During all of this she found a pattern for the panty vibe that was edging you like crazy. Even when the vibrator kicked up to full for several minutes. You couldn't get off, even with you attempting to rock back and forth on the plug for some anal stimulation, it just wasn't enough. You've certainly made your panties wet though. As the panties are drenched in precum from watching her get fucked.
"Oohh my sweet Mary. That was a lovely fucking I just got. Even though that was just me testing the waters, it was certainly enough for me to know we brought something we're going to use more than a few times."
Giving you a contented smile before she slides herself off the dildo. Laying down on the soft rug for a few minutes to recover, she drinks some water and then shuts the panty vibe off. Standing up, she walks over and sits on your lap giving you a big kiss. After the kiss she uncuffs your wrists and pulls you in for a cuddle, you wrap your arms around her to cuddle her back.
"Now that my little test with it is over. I'm going to switch out the dildo to one of the black dildos we have, and while I do that I want you to decide.. Do you wanna be the first to get fucked by the machine using one of them, or do you want me to be?"
You first, or her?
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Are you willing to try this?
When your wife gets more into your feminisation.
You and your wife have always been adventurous, and willing to have fun together in and out of the bedroom. While you're not exactly the peak of masculinity, you're not complete enfeminate. You won't get called buff, but you won't get mistaken for a women when dressed as a guy. You've always been willing to accept the kinks your wife introduces, as they've always led to fun for both of you. Are you going to make decisions that will push you quickly through the changes, or will you need a longer time to accept the changes that your wife is introducing. This story will involve minor and , and will involve the main character taking on the role of a sissy. Either in all or some situations depending on the choices you make. For now I'll be keeping this as a private story, but may allow others to submit chapters in the future. I'll try and make sure updates are semi regular, but as this will be done in my free time they will probably be every few months.
Updated on Jun 7, 2025
by Wolf Keeper
Created on Apr 12, 2023
by Wolf Keeper
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