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Chapter 11
by Wolf Keeper
Do they feel natural on you?
They feel natural
As much as you would like to say having the weight of the breasts on you feels wrong, and that feeling them while attached to you is equally wrong. They don't feel unnatural on you, they feel comfortable and almost normal. You cup them in your hands, and even with the bra you can tell they almost share the same weight as Jane's breasts. It's not something you had expected to ever feel, nor experience.
"Well I can see that you're enjoying them, as you can't seem to stop feeling yourself up."
You give you wife a quick look, and even through the make up, your blush is evident.
"Now, as you're having so much fun playing with them, I'm going to take that to mean they they in some way feel natural to have. Which is wonderful, as this ties into what I want to ask you later."
She reaches out to you, and gentle guides you back to the bed to sit down. Running her hands up and down your stockings as she kneels in front of you.
"I promised a blowjob to you for wearing the plug all day, my well behaved sissy. I plan to keep that promise now, and give you the best blowjob I've ever given you."
Slowly running her fingers back up your legs, she gently grasps the panties at the hips, and starts to pull them down. Raising your hips slightly to make it easier for her, your very erect dick springs out with a small bead of precum forming at the tip.
"Always the way with you, put the plug in and your dripping like a schoolgirl who has just had her first orgasm... Now, seeing as you're dressed as Mary, and normally we don't play with your little clitty as if it were a penis... We're going to make an exception from here on... You'll be allowed to use your little clitty on me when dressed as Mary... But only when I allow it... And you MUST have a butt plug in and have your breasts... No exceptions, no plug, no breasts, no using your clitty like a boy when dressed..."
Saying all this while alternatively between licking around the head of your clitty, and sucking on it gently. You're brain is getting foggy in lust, and while you hear everything she is saying, you know you're not going to disagree with her right now.
Moaning like mad, and struggling to stay sitting up right from the sensations of having your clitty sucked and licked. You manage to lean forward and look down at her, before nodding your heading in agreement with everything she just said.
With that she gives you that same impish smile she gave you this morning, before she going down as deep as she can on you. Which as she doesn't give you blowjobs often, is only down 4 inches. Running her tongue around you clitty as she tries to deep throat you. She backs off, and starts to gently kiss your clitty from head to root, before going back up and again sucking on your head like a lollipop. All the while she is looking squarely at you, while you're moaning.
While the blowjob has lasted 15 minutes so far, you feel as if this has been an eternity of teasing. Everytime she senses you're close to cumming, she backs off and slows down. Then starts back up to maximum teasing again once you've called off. You're not quite sure how much you can stand before you cum without warning.
"Enjoying yourself Mary? I told you this would be the best blowjob I've given you."
For another 10 minutes she keeps the same pattern going. Bringing you right to the edge before letting you cool off. Then she does something completely unexpected, and entirely new to you. Something that you didn't think she would ever do while you are wearing it, because you've never been in this position with her before while it's been in. As you're sitting on the very edge of the bed, your ass is hanging partially off. An because of this, the shock sensations you feel when she starts to slowly work the plug back and forth in you, as if she were fucking you with it. It sets you off, and you see stars. It's the hardest orgasm of your life so far, and you can't help but fall back onto the bed. Just because you pass out, you feel her release your clitty from her mouth, after she has cleaned up all your cum from it. Climb up onto the bed next to you, and pull you in for a cuddle. With you passing out in her arms, as she gently strokes your hair.
The post orgasm aftercare
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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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