Chapter 23
by Wolf Keeper
Playtime continues
Are you ready to be fucked?
After a short period of time relaxing together, and the come down from the spanking sessions. Jane slowly gets up and takes your hand leading you to standing up with her. Turning the TV off, you both make your way to the bedroom, with Jane going up the stairs first. Using this opportunity to hang back walking up the stairs, you get a lovely upskirt view of your wifes white cotton panties. Looking over her shoulder down at you, after noticing that you weren't walking up the stairs behind her. Jane notices you're looking up her skirt, and gives a little wiggle while flipping the back of her skirt up. You make your way upstairs behind her after the nice view, and as you reach her you give her bum a small squeeze. Giggling at how silly you were, she takes your hand and leads you to the bedroom.
Entering the bedroom, she takes you into the walk in wardrobe sits you down on the stool in there. Kneeling in front of you she takes off your Mary-Janes and then stands up to place them on a new shoe rack on your side of the wardrobe. She then bends over at the waist, making sure to flash you her panties, and takes off her Mary-Janes. With you both now shoeless she walks over to your toy chest and wheels it into the bedroom and leaves it in front of the bed. When she starts to wheel the toy chest, you stand up and follow her out of the wardrobe, closing the doors behind you.
She tells you to lay down on the bed while she opens the toy chest with her back to you. Give you further peaks up her skirt while she's getting what she wants out of the chest. She stands up and you can see her holding two dildos. The first is the largest dildo you own, it's 7" long and half an inch larger around than you are. It's a dildo that you end up using on Jane everytime you're both in lingerie together. In her other hand though, is a new dildo you don't recognise. It looks to be the same length and the same thickness as the first one, but you know it's not one you've seen before tonight. Walking over to her side of the bed, she places the first dildo on her bedside table. Then using the suction cup you didn't notice before, and sticks the second dildo onto the headboard.
Laying down on the bed next to you, she takes both of your hands into hers and looks you straight in the eyes.
"Now, I know when we've played with the dildos in the past it's always been with either me using them on myself. Or it's been you using them to fuck me while using your hands to hold the dildo. Tonight though, I want to try using them on you for once."
Once she says this, you go wide-eyed with uncertainty.
"Don't give me that look. You're ready to feel what it's like to have a cock inside you. It's not like it'll be a real one."
Going even more wide-eyed at her suggestion. The thought of trying one of her dildos never crossed your mind until she hinted at something this morning. Before that you do recall her mentioning the last few times you've been Mary that she would like to you them on you, but you've always been too apprehensive about it. Looking into her eyes though, you see her big hopeful eyes that you'll agree to it.
"I know it's a step you've not wanted to take, but with you wearing the plug all day yesterday. Something you would have never considered before then, and with you wearing the larger one you have in now today. Can you honestly tell me that the experience of them inside you has been bad. Or that you feel like a dildo would be any different?"
While you're conflicted over whether you should. The part of you that is hyper turned on is starting to win over the nerves and uncertainty. You know she wouldn't suggest this if she didn't think it would be pleasurable for you. An she is right that having worn the plugs for so long, that they've increased the pleasure in everything you've been doing today and yesterday. Looking at her, and then at the two dildos in front of you. You wonder if you can even take a toy this size inside you.
"The fact that you're looking at the dildos, and haven't immediately started saying no yet, is good. I have a feeling you're wondering if you could take a cock of this size, right? Well let me answer that for you. You technically already are. The plugs that are inside both you and me are just slightly larger around than both of these dildos. While not as long, the depth isn't as important to start. As long as the width of them isn't going to tear you, you'll be fine."
While saying this, she shows you the torn packaging for the plug you're wearing and the untorn packaging for the new dildo. Pointing at the diameter size indicated on the two.
"If you're still not sure even with this. Then I can use a smaller dildo on your first before we use these two. I'll leave that up to you to decide though."
Large or small?
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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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