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Chapter 7
by Wolf Keeper
Dressing up time
Lingerie, dress, and learning to walk in heels
Taking your hand and dragging you upstairs very excited, when you get to your bedroom Jane tells you to strip off your joggers and t-shirt. Once your down to the panties you put on this morning, you sit on the bed and wait for your wife to return from the wardrobe. As she walks out of the wardrobe she has two dresses on hangers that she hooks onto the outside of the wardrobe door, then turns around back into the wardrobe. A few minutes later she comes back out holding what looks to be two sets of lingerie in her arms.
Setting the lingerie down on the bed, she then tells you to go into the bathroom and wait for her. Coming into the bathroom from the wardrobe she has two metal pink jewelled butt plugs in her hand and a lube bottle in the other. Stripping off her own clothes and getting you to remove the panties you borrowed. You step into the shower with her and have a full shower, cleaning yourself inside and out. After drying yourselves off, you bend over and feel her insert your plug then she turns around and has you insert hers.
Once your both plugged she takes your hand and leads you to the bed where she starts to dress you in one of the lingerie sets she got out earlier. Your set is a cobalt blue, and hers is an amethyst purple set. You do notice that the set your wearing doesn't have the same size bra cups as the set that Jane is wearing. Besides the differences is in cup size, and colour the sets are identical. Both bras and longline balconette in style, with mostly satin cups and band with lace overlaid on the cups. The suspender belts are both high waisted that are satin all around with the same lace overlay, with 6 wide straps each and metal clips. The panties are bikini cut, also full satin front to back and lace overlay on them at the hips. Attached to the suspender belt are matching seamed stockings for you both, that have satin bands for the clips and a cuban heel.
Once your both full dressed in your lingerie, and finished admiring each other in your lingerie. Jane takes one of the black dresses she hung up earlier and helps you step into it, before she then steps into her own. Leading you to her vanity and having you sit down, she starts applying make up to you, explaining each step as she goes. With your make up applied and after applying hers, she then helps you put on a pair of black heels and helps you walk over to the full length mirror.
Though you don't have the breasts that she does, with your more feminine hips and thin waist you look into the mirror and see a woman with small breasts staring back at you. If it weren't for the lack of breasts, you could almost believe you were looking at a younger version of your mother Anastasia staring at you. While you've told since a child that you looked more like your mother, you never quite believed it until you saw yourself in the mirror.
"Well Sweetie, do you believe me now when I said you would make a beautiful woman? As right now I see a very beautiful woman in front of me, who I would love to take out with me to show off. Not that I would until you were comfortable of course. Now we're all dressed up in the middle of the day, and while we're not going out. We are going to make sure you can walk, talk, and act like a woman, should we ever go out together."
You can only nod in reply as you're still surprised at how convincing you look. You feel her taking your hand and slowly take you through how to walk in the heels your wearing. While they are only a 2 inch heel, as this is the first time you've worn heels you need some time to adapt. She has you walk a few loops around the bedroom, then has you walk the length of the upstairs hallway several times as well. You slowly get used to the heels and after a few hours of walking with some breaks in between. Eventually you walk down the stairs with Jane helping you down. You make a quick lunch together before you spend some time learning how to sit, and act like a woman.
You spend most of the remaining part of your day doing this, repeating the instructions that your wife tells you. While still clunky in your movements, you almost forget that walking in heels and by the time dinner comes around Jane believes you could pass for a woman in public. After making dinner with her with the food she got earlier, you get changed out of your dresses and just lounge around in your lingerie for the evening watching a few TV shows and then a film together.
Playing with toys
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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