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Chapter 8
by Wolf Keeper
What's next?
Comfortable
Nodding your head in reply, the realisation hits you. While you were concerned at the start of the day, no one said anything or brought up that you were looking or behaving odd. Whether that was due to how busy the meeting ended up being, or because you genuinely didn't look any different, you're not sure. All you know is that you never once felt uncomfortable after getting to work, and focusing on what you needed to do.
"Good, I'm glad you managed to feel comfortable with our little experiment today. This should make what I have to ask of you later a little bit easier. For now though, the final question I have is. Are you looking forward to making passionate and sensual love to me, while we're both dressed in sexy lingerie, and wearing plugs?"
With this, you nod your head vigorously, like you could almost strain your neck with how much you were nodding your head. You desperately want to make love to your wife right now.
"Good, then my sweet Mary we're going to get you into your bra, suspender belt, and stockings. That way you're all dressed up like my good little sissy girl should be."
With that said, you hear the sound of your bedroom door opening. You feel her gentle push you through the door, and then stop you just inside.
"Now, I'm not going to be taking that blindfold off until you're fully dressed. I want you to just relax, and let me get you fully dressed in your lingerie. Please do not reach up to remove the blindfold, as it would ruin the surprise, and upset me a lot."
Turning you around, you get directed to sit down on the end of the bed. You feel the cami top get pulled up, and your wife asks you to lift your arms as she takes it off you. Next you feel her wrap what feels like a high waisted suspender belt on you, with the 6 straps dangling by your side. You then put your arms out behind you, as directed by Jane. You feel the straps of what you assume is a bra get slide up your shoulders, and once the bra is in place get clasped at the front.
"Good girl, now I want you to lay down on the bed for me. You're going to feel some weight on your chest soon, but no moving your arms to reach up and feel. Keep then at your sides like a good girl that you are."
Laying down, you hear something get sprayed near by you. Then you feel your wife undo the front clasp of the bra she put on you, then a slightly cool sensation as she seems to be running something over your chest.
"It's a good thing we keep you hairless for our games. The hair removal treatments for us both cost a lot, but we both know it was worth it."
After she says this, you feel the weight of something soft being placed on the left side of your chest, then the same on the right. Afterwards you feel her close the clasp on the bra, and gets you to raise slightly so she can adjust the straps of the bra to make sure it fits correctly. Next she runs one of her hands down your stomach, then past your crotch, lightly running her fingers on your dick as she does so, then down your legs.
She lifts one of your feet, and you can feel her gentle pulling a stocking up your leg. Once you feel the stocking top reach your thigh, you then feel your wife attaching the straps and adjusting the tension for each. All the while after each strap, she makes sure to run her fingers up and down your leg. Repeating the same for the other leg, you then feel her slip a shoe on each foot. As you set your feet down, they stay at an angle, making you realise these are heels. After she's done with your stockings, and the heels. You feel her go back to your chest, undo the bra before working on your chest again. Then doing the bra back up again.
"Now, I know this is the first time we've had you wearing heels. I felt though, as this is going to be what I hope will be a special night for us. That you wearing heels would be appropriate for the occasion. Now, I want you to slowly sit back up, as I want to slip your cami top back on before we continue."
Slowly sitting up as directed, you can feel the weights on your chest shift slightly and pull on the bra straps. You're slightly confused by the sensation, but you realise that somehow your wife has found a way to make you have the feeling of breasts.
"Now, I know the weight on your chest is not natural for you. I'm sure you've figured out by now that you've got the weight of breasts on your chest. You're not going to see what it looks like though, until AFTER I'm done."
She raises your arms, and you feel the cool satin of the cami top drift down you arms, then chest. As you go to put your arms down, Jane directs you to put them out in front of you. You then you feel something get pulled over your arms, and then wrapped around you. It's soft, warm, but not heavy, an you figure she's put one of the snuggies you both have on you. As you lower your arms, she gets you to stand up and she moves you over to her vanity, and then sits you down.
"I know you're confused, but as I'm going to need to take the blindfold off to do your make up. I don't want you seeing your complete outfit until I'm done. I've also covered the mirrors in the room, so you won't be able to see your reflection until I'm done. While I'm doing your makeup, you're to keep your eyes closed until I tell you to, and your head & eyes looking only where I tell you. I want this to be a big reveal. Now nod your head if you understand."
You close your eyes as you feel her undoing the strap holding the blindfold on. Next you feel her pulling your hair back into a high ponytail, which must be to keep it out of your face whille she works. Starting to put make up on you, a couple of times she asks you to open your eyes while she's working on your eyes. During the few times you are allowed to open your eyes, and look where she directs. You can confirm that she covered up the three mirrors on her vanity, and that Jane was also wearing her snuggie. When she sees you notice the first time, she just gives you a wink and pokes your nose gently, before telling you to close your eyes again.
You hear her make a small squeak of glee, indicating that she's finished your makeup. She then loosens your hair, and what feels like her playing with it, starts to style it to help give you a more feminine look. The make up, and the hair feel like they take 40 minutes, though you really have no way to tell.
Get out of your own head
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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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