Chapter 4
by Wolf Keeper
Do you wear just the panties, or both panties and butt plug?
Wear both
Deciding that as you've already managed to upset your wife once, potentially upsetting her again by only wearing the panties wouldn't be the best idea. You agree to wear both. You just hope that the meeting today won't take very long, and your not going to get distracted by the plug too much. You bend over at the end of the bed while Jane gets the lube and the plug. Returning to the bedroom to see you already bent over, she walks behind you and squirts some into you using the nozzle. You then feel the lubed plug being pushed against you. A few minutes after it popped into place and she gives you a quick spank on your arse and telling you to stand up.
"Good girl, now that you've got your plug in. Lets get this pretty thong on you, and then you can finish getting dressed for work."
You life your legs to step into the thong she's holding for you, and pulls it into place making sure it's holding you comfotably. Once she's finished, you had forgotten that the strap is going to keep pressure on the plug. You then feel Jane pull the front of the panties forward and tuck your dick in with a panty liner.
"There we go, now you won't be leaking precum directly into your panties, considering that the plug tends to get you excited when you wear it. I'll even give you a spare if you need one up too much. Now, I'm going to add this cami top to the deal, as it matches the thong, and I want you to be wearing matching lingerie."
She picks up a cami top from a different draw of her vanity, and then slips it on you. Rather than argue that this wasn't part of the original agreement, you just accept that this is going to be something you're now wearing. You hold your arms up as she slips it onto you, before helping you get dressed into your work shirt and trousers. You then put your socks, shoes, tie, and then suit jacket on before giving her a kiss on the cheek and walking down stairs. You have breakfast with Jane and then picking up your work bag head out the door to work.
Off to work I go.
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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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