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Chapter 6
by Wolf Keeper
End of the week
The weekend
With the rest of the week being kinda dull, it goes by fairly quickly. Waking up on Saturday, you wake up to note from your wife saying that she's gone out for a few things and will be back later. You go for a shower and then head to the wardrobe to get dressed. Opening the draw with your underwear you realise that Jane had asked if you'd be up to wearing panties for the weekend. Thinking you'd surprise her, and knowing she won't mind you wearing her panties without permission. You close your draw and then open her plain panty draw and pull out a pair of plain white cotton panties and put them on. Then you put a pair of jogging bottoms and a plain t-shit on and head downstairs.
Having some breakfast, you head into your office and catch up on some comics, and other daily catch ups before spending a hour or so gaming before you hear Jane return home. Opening the front door for her as she's walking from her car, you can see she's carrying several bags from 2 stores. It looks like she went to pick up so food for the weekend and picked up some new art supplies for herself. Helping her carry the food bags in and putting it all away, she puts her art supply bags in her office/studio space and then gives you a hug and a kiss for helping her.
"Hey Sweetie. I'm sorry I didn't wake you up before I left, but I wanted to pick up food early before the shop got busy. I also needed to get myself some new brushes and paint cleaner. You been awake long?"
"Not been awake for too long, maybe an hour or so. I didn't really do much though, just played a few games before I heard you get back home. Oh, and while I know you didn't specifically mention playing this weekend, but I remembered what you said during the week. About me wearing your panties this weekend as I didn't wear them on Monday like you asked, so I'm wearing a pair now. Just a plain white cotton pair, nothing fancy."
"oh Sweetie, of course it's okay. I actually was planning to ask if you'd wear a pair when I got home, but I guess you were ahead of me. I did have something else in mind though, as it's the weekend and we've got most of the day together still. Would you be interested in fully dressing up as a woman for me? We'd stay home, and it would just be for today. I've been wanting to see how you'd look fully dress for awhile, and as it was the 10 year anniversary of our first date on Monday. I figured we could make it special this weekend instead."
"Wow, 10 years since our first date together. I felt like you were setting me up on Monday with wearing your panties for a particular reason. I didn't realise it was that, I'm sorry I didn't go along with it. As you want to make it special, and I remember you've mentioned having me fully dressed as a woman in the past. Then why not, we can give it a try for today."
Eliciting a big squeak of glee, and a small jump from Jane she gives you a big kiss and then grabs your hand leading you up stairs.
Dressing up time
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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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