You agree to her request.

Pondering it over, you can't see anything wrong with the idea. You've done it once, you don't take your suit jacket off enough for people to even get a chance to see through your shirt. An even when you have taken it off in your office, you rarely get interrupted outside of planned meetings. You've basically talked yourself into it at this point.

"Okay, I'll try wearing them on Wednesday for you..."

Jane looks at you in surprise, but you can tell she's very excited by this news and starts to say something.

"...However, this will only be a test on Wednesday. As it'll be a regular work day, there is a greater chance it'll get noticed compared to today where everyone was super focused..."

As quickly as she got excited, you see her visible deflate a little bit at you putting a condition on it.

"...If it goes well on Wednesday, then I'll do so again on Thursday. As I want to take it one day at a time for now. Are you okay with this?"

You see her think it over briefly, before she nods her head.

"Okay, I agree that we won't rush you wearing your lingerie to work. The last thing we need is this causing problems for you there... Next I want to ask you about the butt plug. With you wearing it all day today, and by your own words, forgetting about it for most of the day. Would you be open to wearing it every now and then, maybe okay weekends to begin with. I'm not asking for you to wear a plug to work, at least not right now. But, would weekends be okay with you?

Thinking it over, you can't see why not. So long as it's weekends only, you can't see the harm in it. You nod your head.

"Okay, then we'll see how Wednesday goes for you wearing your plain lingerie under you work clothes. For tomorrow though, are you willing to wear the plug again?"

Considering you've already worn it all day today, you feel like you could wear it tomorrow.

"Sure, but if it gets uncomfortable for me then we take it out, okay?"

Nodding her head, she gives you a kiss and cuddles you tightly.

"Today has been so much fun, and I can't wait to see how tomorrow goes. For now though, we need to take off our make up, and have some dinner before we go to sleep. As I don't know about you, but I wanna curl up with you after dinner, and fall asleep watching a movie cuddled up together."

Both of you get out of the bed and go into the bathroom, Jane then teaches you the best way to remove make up using the make up removal supplies that she has. Once all the make up is removed, you still look more feminine than masculine at this moment. Your hair is keeping you from see your regular appearance. Taking your hand, your wife leads you downstairs to the kitchen, where you both work on making a quick dinner to enjoy.

Heading back up to your room, you relax with Jane while eating your dinner and watching the romantic comedy that she had on earlier. Once you've finished your meal, you take both of your plates and set them on top of your chest of draws, before returning to bed to cuddle with your wife. You're not sure when you fell asleep, but you're pretty sure you both fell asleep at the same time.