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Chapter 28
by Wolf Keeper
A short time skip
Skipping to the weekend after next
After your nice girls night together, Thursday and Friday follow a similar pattern to Wednesday. Though with the novelty of you wearing your new everyday lingerie under your clothes wearing off. You went to work, got on with the day, then came out to spend time with your wife. No crazy exposure at work, no one giving you funny looks. The weekend is relaxing with you going out to spend some time walking through the park enjoying each others company. Your wife does take you to the local shopping complex over the first weekend since you started wearing lingerie every day. Even though you've got plenty for both of you, she wanted to pick up some sets for both of you together. You also had to accompany her while she picked out some female clothing for both of you to wear together as girlfriends.
She's made it clear that at some point she does want you both to go out while you're fully dressed, and that it will be at a pace you're both feeling comfortable with. You did spend that Sunday once you got home fully dressed as a woman, from hair, make up, nails painted included. Further practicing your female mannerisms and walking in a higher pair of heels. She did make you wear the second plug on both Saturday, and Sunday though. As she did try the smaller plug on you both, but both of you struggled to stop it from slipping out. It looks like you've both gotten used to having the larger of the two in now.
The next week is with out fanfare. Again there were no comments or odd looks. You even wore the plug on the Wednesday at Babe's request. You made love to your wife during that week as well. As Jane relaxed her rules on making love to her with your dick when in lingerie to say you don't have to be wearing the plug or breasts. Though it still only when she allows it.
All in all, you've not worn male underwear since your 10 year anniversary, and it doesn't look like you will be any time soon. Though she did keep one of the small draws dedicated to them, just incase you have a doctors appointment, or something similar. With all the new things going on the past couple of weeks, you both have neglected working out on your normal schedule. Though you've both been keeping active enough to feel like you have compensated for that.
On the Friday night of the second week. Jane reminds you of the skipped workouts, and that tomorrow and Sunday, your both are going to spend sometime together in the gym. She also mentions that as you've gotten so used to wearing lingerie. She's gotten you some more appropriate work out clothing. Though she doesn't give anything more to you that that.
Weekend plans
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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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