Disable your Ad Blocker! Thanks :)
Chapter 52
by Wolf Keeper
Straight on until morning
Getting dressed
Wake up to the sound of your alarm, you slap the snooze button as you snuggle into Jane who are you still spooning from last night. Feeling her wake up from your alarm as well, she rolls over to face you and gives you a soft kiss on the lips and a smile.
"Morning Mary. Did you sleep well my darling sissy? I definitely did, as the last orgasm you gave me from eating me out was perfect."
Wiggling her way out from your arms, she stands up and does a stretch. Admiring the view of her stretching in the babydoll she's wearing, you kick the duvet off and stretch yourself out in bed.
"Surprisingly, I did sleep well last night. I'm surprised that I didn't wake up to some pain from typical morning wood being stopped by the cage. As that happened with the other cage we had."
"I'm glad you slep well Mary. I guess your design for the new cage has worked out better than we thought it would. Now, get out of bed, get into the bathroom, and get yourself clean."
Getting out of the bed, albiet unwillingly. As you would prefer to stay cuddled in bed with Jane all day. She's right, you can't stay in bed as you have work today.
"While you're in the bathroom, I'll lay out your lingerie today for under your clothes. An before you even ask, yes your staying in the chastity cage all day today. I'll unlock the harness so you can clean the plug and yourself out fully, but when you walk back into the bedroom. I want you plugged and the harness locked back onto you. Is that clear?"
Nodding your head to the rhetorical question. She takes a key from her bedside table draw and unlocks the buckle of the harness and quickly explains how to lock it back on when you're done. Walking into the bathroom you undo the straps holding the harness to your new cage, before taking the harness off completely. Reaching back you pull the plug out and set it in the sink for cleaning after your shower. Going through your morning routine, you then clean the plug, reinsert it, and then head back into the bedroom after locking the harness back on.
When you get back into the bedroom you find a full set of pink lingerie waiting for you on the bed. You also find to your surprise, a corset and a matching pink corset liner. You wonder if you can get away with wearing a corset to work, when Jane comes out of the wardrobe with your trousers and a work shirt for the day. You also notice that she's put on the matching panties to her babydoll, and a thigh length robe.
"Alright, I want you to get dressed in the lingerie on the bed except the corset liner, corset, and stockings. I'm going to go to your office and get your suit jacket real quick, which will give you time to put on the bra, and panties."
Quickly donning the bra and panties laid out. While not bright pink you are concerned that they will show through your white work shirt, and whether the suit jacket will hide the outline of the corset. You take a closer look at the lingerie that Jane has chosen for you while you wait for her to come back. It's mostly satin, which a bow between the 'cups' of the bra and a two bows at the hips of the panties. The panties also have a zip going from front to back, which is concerning for a pair of panties your supposed to be wearing all day.
"Alright, arms up. I need to pull the corset liner down and then get the corset on you. We're going to go into the wardrobe, as you're going to need to grab the corset lacing bar we have. Then I'll roll your stockings up and attach them to the suspenders, and then we can get you dressed in your suit."
While saying this, she hangs your suit jacket on the wardrobe door hooks, and then walks over to pick up the liner and corset. Leading you to the wardrobe, you raise your arms as she helps you get into the corset liner and settles it into place. Next she wraps the corset around you and closes the front busk, before she has you reach up and grab the lacing bar. She pulls on the laces a few times and gets the corset tight around you. She doesn't lace it to where it feels like it's going to cut your oxygen supply off, but it does add some curve to your body that wasn't there before.
"With it as tight as it is, it's going to have taken about 2 inches off your waist line. As this is not a training corset and more of a fashion one, I'm not going to tighten it all the way. Plus you're not used to wearing on and I wouldn't want to restrict your movement too much. Now time for your stockings then your suit, and then off to working with you Sweetie."
Walking back over to the bed, you remain standing as Jane rolls the 1st stocking up your leg. Feeding the suspender straps under your panties, she gets the 3 straps for the stocking secured and adjusted for correct tension. Then repeating the same steps with the other stocking afterwards. She then unzips the panties from the back and does a quick check to make sure you're definitely wearing the correct plug. Then while standing, she zips the panties up and walks in front of you. Pushing the straps of your bra off your shoulders, she pulls the cups of the bra down. She then produces two small beige circular objects before she squeezes them onto your nipples. You feel them suck your nipples into them as she releases them, trapping each nipple in a little beige dome. She then pulls the straps and the cups of your bra back up so you're wearing it correctly again.
"Those little caps are nipple suckers. They are designed for nursing mothers with inverted nipples, and are meant to pull the nipple out and help them stay out for breast feeding. However, I've discovered in my research that they can also help men and trans women increase their nipple sensitivity and size. So, you're going to wear them all day today, and when you get home we'll see how sensitive they have made your nipples. Oh, and I'm also going to be wearing my own, as I've always wanted to increase the sensitivity of my own nipples."
Tugging the cups of her babydoll down enough for you to see the same beige domes over her nipples. She then helps you get dressed into your suit and get your shoes on for work. Following her downstairs you find Emma in the kitchen making herself and Anthony breakfast wearing a lilac chemise and an open robe over it. While Anthony is sitting at the breakfast table reading the newspaper drinking a coffee.
"Good morning John. Have a good day at work."
Hearing Emma wishing you a good morning, you look over to her as she smiles and waves at you. Give her a smile and wave back, you then kiss Jane goodbye while giving her a hug. You then walk to your car and head into work.
After work
Disable your Ad Blocker! Thanks :)
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
You can customize this story. Simply enter the following details about the main characters.
- All Comments
- Chapter Comments