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Chapter 13
by Wolf Keeper
The true discussion
How far will this new thing go?
After fucking herself on you to orgasm, one which you managed to share. Albeit with a much weaker orgasm from the blowjob. She gets off you, slips her panties back over her pussy, slips your clitty back into your panties and leans back on the headboard next to you.
"Now that we've both had an orgasm, and we're both no longer going to be blinded by lust, nor sexual excitement. I think it's time we have a proper discussion."
With that she sits more upright, for which you join her in doing so.
"John as this is going to be a more serious discussion, I want to ask you something to start with. You said that you wouldn't be opposed to continuing to wear lingerie to work on occasion. If I said that I had brought some plain regular panties, and not full lingerie. Would you be willing to wear a plain pair of panties to work everyday from now on?"
You're not really surprised that she's asking you to wear panties more often, you are surprised that it would be everyday.
"Umm... I hadn't thought it would be everyday, I figured it would be more often though. Would it just be wearing plain panties under my clothes?.."
"Well... Seeing as you're asking, I do have more than just plain panties for you to be wearing. I actually got some matching plain camisole tops, and had bras made that look like training bras for you to wear as well. I was planning to bring them up at a later time, and not put everything on you all at once..."
Giving you a blush and looking out the corner of her eyes at you, lowering her head to make herself look cute.
"...As it went so well today, and you had so much fun. I would prefer it if you did wear the matching sets of plainer lingerie under you work clothes."
"That's alot to take in Jane. It's only been one day, and you're already asking me to be wearing a full set of lingerie under my clothes. I'll need to think about this."
Continuing the discussion.
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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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