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Chapter 27
by Wolf Keeper
After work activities
A girly evening
"Well, seeing as you're so used to wearing your lingerie now. Why don't we go upstairs and get you changed out of your suit, and you can show me your self self in the lingerie you chose for tonight. I can also show you how I've organised your chest of draws to hold all your new lingerie for you."
When you enter your bedroom, Jane promts you to remove your outer clothes for her, as she sits on the bed watching intently. Taking off your shoes, then your socks, as to not give her an early view and defy her expectations of unbuttoning your shirt as you normally do. You poke your tongue out at her when she gives you a pout and you removing the boring bits first. Before you continue further, you spy the blindfold she used on you on top of her vanity. Moving quickly you grab the blindfold and have it wrapped around her head before she can react. She tries to remove it as you're putting it on, but you quickly lean her over and spank her exposed bum acouple of times to get her to behave.
"Stop being a brat! I think it's only fair that as you want to see which set I chose of lingerie that you brought me. I get to choose how you see it. After all, you had all this planned for months, and I've had to follow your machinations up until today. You can sit there without being able to see until I'm fully undressed. Or am I going to need to get the waist belt and cuffs to secure your hands at your sides like a good girl?"
She stops struggling with you and sits on the bed with her shoulders dropped and hands held together on her lap. Satisfied shes not going to misbehave, though you can see the very large pout she has right now. You remove your outer clothes while keeping a keen eye on Jane to see if she's going to misbehave. She behaves herself though, and doesn't move at all except to get more comfortable while you undress. Once fully undressed you give her a kiss on the cheek, stand her up and then remove the blindfold.
"Oh Sweetie, you look so cute. I'm surprised you went with lavender for the first full trial day. I would have expected you to choose one of the plain tonal options, not something, well, girly as your first choice"
"I thought about wearing one of the grey sets, but I figured I'd surprise you. Plus the big smile you have right now made it worth it. Even with you acting briefly like a brat when I wanted to surprise you."
"Well you could have just asked me to close my eyes instead of blindfolding me, I would have..."
"...We both know you wouldn't have kept your eyes closed. You would have peaked, because you're a brat when you can't have your way when you want it."
She pokes her tongue at you when you interrupt her, and then gives you a pout when you call her on her behaviour.
"Fine! I would have peaked you're right, but don't think that will make me forget that you said you missed not wearing the plug today. I think as you missed your plug so much, we should put it back in you now. I'll even wear my plug with you."
She walks into the wardrobe, and you hear her open, then close the toy chest. Coming out from the wardrobe with two plugs in hand and a bottle of lube. You follow her into the bathroom to make sure you're both cleaned out before inserting the plugs.
Both of your plugs slip in easily, and while you won't admit it. You give the plug a squeeze inside you and confirm that it doesn't feel larger than the one you wore yesterday. With you both now plugged, dressed only in lingerie, you head down stairs to share dinner with your wife. AFter dinner you sit on the sofa together, and you watch a short comedy together before going back upstairs.
When you're back in your room, Jane suggests that you paint each others toe nails for fun. As no one will see your toe nails during the day you agree to this, though you stipulate she can't give you bright pink toe nails, even if no one will see them.
Doing each others nails feels weird, though Babe teaches you what to do to avoid ruining her nails. You end up doing both hands and toes while a rom com you've watched many times before is playing in the back ground. When you finished following her directs into cutting, and shaping her nails. She hands you one of the jars of nail varnish have you paint her nails all the same colour of light pink. She then repeats what you done to her on your nails, though she paints your fingernails with a clear varnish rather than the light pink she put on your toenails.
Doing each others nails was more relaxing than you thought it would be, and when you're finished you spend another night cuddled up together. No sex, no teasing or playing with each other. Just a night of being with each other, appreciating that you have each other.
A short time skip
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.
- Tags
- 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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