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Chapter 9
by Wolf Keeper
Get out of your own head
A brief moment of despair
When Jane has finished primping and preening you hair, she stands you up and has you walk a short distance. If Jane wasn't supporting you, you're sure you'd have fallen flat from not being used to the heels. You can hear the sound of a sheet being pulled, off what you can only assume is her free standing mirror. You then hear her taking off her own snuggie, before she removes yours. Several more agonising minutes pass as you hear her putting the sheets and snuggies away, lighting candles, putting some mood music on. You can only this is to make everything perfect before you can open your eyes.
As you hear her doing all of this, you start to wonder how long she had been planning this. While she could easily make sure deliveries, and her shopping trips to get all of this would be done while you were at work. The amount of time, it just makes you wonder how you didn't notice it. You start to feel like maybe you weren't paying enough attention to her, or to what was happening around the house as she was planning this. Nothing seemed out of place, or unusual. You hadn't played at being her lesbian lover for the two months she was busy with commissions. She figured she was too busy to initiate the play time, and while you still made love to her over that time. You wonder if you should have been the one to initiate it, and maybe she wouldn't have had to plan all of this.
You then start to notice how you're feeling. The soft satin lingerie your wearing, all the lace edges and trim you can feel without even moving your hands. The shoulder straps from the bra, as this unexpected but not uncomfortable weight on your chest pulls at them. The same with the stocking tops, how the straps feel taught against your skin, and how they tugged at the belt when you were walking. How the heels, while uncomfortable, are making you stand taller and making you adjust the way you stand to stay up right.
Finally you focus on your dick, and the butt plug. You had again forgotten that you were wearing it this entire time Jane was getting you ready. It's pressence unknown besides when she brought it to your attention. While not a large plug, as it was the smallest one the website offered. The slight pressure on your prostate the entire time you've been wearing it, your accutely aware of how on edge you've been since getting home. Which is now amplified thanks to your wifes teasing, and the slow sensual way she dressed you.
You feel like you shouldn't be enjoying any of this. You're a man, not a woman. While your brief forays into the role of the fairer sex for your wife's enjoyment have been fun. This feels like things have been taken to a whole new level. A level that makes you feel like if this were to become the norm, would you be able to accept it?
A comforting hand
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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.
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- Chastity, fucking machine, fuck machine, Sissy, Feminization, Cuckold, Submissive, Pegging, strap-on, dildo
Updated on Jun 7, 2025
by Wolf Keeper
Created on Apr 12, 2023
by Wolf Keeper
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