Chapter 49
by Wolf Keeper
Who is there partner?
Male Black Domi (Sub/Cuckold Chastity route)
Walking into the house on the Monday of the fourth week, you hear the TV from the living room and take a look. Sitting on one sofa you see Jane laying down with a blanket over her watching the movie currently playing, and on the other you see Emma and an unknown black male sitting next to her that you don't know. You assume it's her partner, but you can't get a good look as they're both facing away from you. As you get closer to the living room you see Jane raise her head to look in the direction of the door and sit up when she sees you.
Getting off the sofa, she walks over to you wearing a mid thigh length purple chemise, and an open long robe over it. Wrapping her arms around your neck as she kisses you, she then helps you take off your suit jacket and walks into your office with it and your bag. While she does that you hear the movie get paused and see your sister in law and who you assume to be her partner stand up and walk towards you.
"Hi John, this is Anthony my boyfriend. Anthony, this is John my brother in law."
Offering your hand for a hand shake, Anthony takes your hand and strongly grips you in a hand shake.
"Hi John, it's a pleasure to meet you. Thanks for agreeing to let me stay over every now and then. It was getting difficult for me and Emma going back and forth. Hopefully it won't have to be much longer though, as I'm looking for a place here to move in with her."
Letting go of your hand as he's talking, he wraps his arm around Emma as he mentions finding a place and moving in together. As this happens Jane has come out of your office and cuddles herself onto your from behind, resting her head on your shoulder.
"Oh it's no worry, is it John? It's not like it's changed much with you being here, I certainly haven't noticed and I'm sure he hasn't either."
What Jane is either choosing not to mention, or purposely forgetting is that you have noticed the nights that Anthony has stayed over. You and Jane can both clearly hear when Emma and Anthony are having sex, as she screams out for Anthony to fuck her harder and deeper with his big cock. It's also on these days that you and Jane don't have sex yourselves, as you want to not be heard by them with your play sessions together.
"Now, why don't you go upstairs and get changed into your PJs. Then you can join us watching our movie, as we had only just started it when you walked in. Don't take too long though, as I want to get comfy next you before we restart the film."
Walking into you bedroom, you take off the rest of your suit and head into the bathroom to quickly clean up, and see a surprise waiting on the bathroom counter top. The large jewel plug is sitting on a towel with a note from Jane beside it.
'Wear the plug and what I have left for you in the wardrobe tonight, and come cuddle up with me downstairs.'
Inserting the plug as requested, you go into wardrobe and find a pink babydoll with matching panties next to a plain black t-shirt and shorts. Putting on the clothing left out and heading to the living room, you lay down on the sofa next to Jane and get cuddled up together. As you're getting cuddled in together you feel your wife's hand make its way into your panties to confirm you're wearing the plug as requested, giving it a little tug.
The film gets restarted and you find that the one chosen for tonight is Hitch. You settle in to watch the film, and relax in with Jane. Once the film is over, you eat dinner with Emma & Anthony before retiring to your respective rooms. Not long after getting into the bedroom, Jane tells you to sit on the bed and goes into the wardrobe. She wheels out the toy chest and takes out the strap on with the large black cock already attached from the last time it was used several weeks ago. She also pulls out your chastity cage, and the stretch plug.
A horny dominant wife
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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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