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Chapter 46
by Wolf Keeper
Midday Sunday
A wake up fuck, then prep for the day
With sleep taking you both, the hard fucking you both received had you both sleeping until midday. You wake up to your wife playing with your locked up clitty, and slowly working her hips back and forth working her big black cock between your legs. Seeing you waking up, she starts to kiss your shoulders and you feel her reach down and pull your panties down as she pulls her cock from between your thighs. You then feel the sheets get thrown off you, as the plug gets removed and placed onto her night stand. Then the feeling of the big black cock being thrust inside you.
"Good morning Mary. I hope you slept well my sweet sissy girl. I know I did, and I woke up horny. As we've established that your a slut for big black cocks yesterday, I figured it was only right that you get fucked like the slut you are this morning. Especially as I while I know we were supposed to take that cage off your clitty. I find it cute that it's still locked up, and that you can't get hard right now. That you can't reclaim your wife's pussy from the big black cock that has been inside her all night with that useless clitty of yours."
She starts thrusting at the end of this, getting faster and thrusting harder. A moan escapes your lips, as while you're still feeling stretched out thanks to the plug. You're still able to feel the veins of the cock inside you against your prostate. Her instance at fucking you first thing in the morning after the fucking you received last night make you feel overwhelmed with submissive feelings, causing you to cry out with another moan. The first time you truly feel submissive to your wife, as she fucks you with her big black cock. Rolling you over to get you onto your hands and knees, she starts to thrust even harder into you.
"Fuck me Babe, fuck me hard. You're right, I'm your little sissy, and my little locked up clitty is useless. Just keep fucking me until we both cum. Please..."
As your saying this, you start thrusting back in time with her thrusts. You're now actively fucking yourself back onto her cock, begging her to fuck you. Encouraged by your words, she starts fucking you harder, trying to match the pounding of the machine last night.
"Oh my sweet Mary. I knew that after being fucked by the huge cock last night you'd crave being fucked more."
After several more minutes, you both reach the point of orgasm. Jane collapses forward onto your back, as you fall forward prone with her cock still buried inside of you. Both of you breathing heavy as you recovery from your orgasms. Eventually you both get recovered enough to start moving, with her pulling the cock from your arse you moan at feeling empty. She picks up the plug you had in you all night, then holds you hand and leads you into the bathroom, where she places the plug into the sink. Stripping off your baby dolls, Jane removes the strap on, and then pulls her panties down to remove the cock inside her. She sets the cock next to the strap on and the plug.
You both use the toilet and take a shower and cleaning yourself fully, and then dry yourselves off. After the shower you walk over to the sink and start cleaning the toys and plugs from your play sessions. When the big black cock that has been inside her is clean and dry, she then rubs the head against her pussy to lube it up, before slowly pushing it back inside herself. Keeping her legs together to have her thighs stop it from coming back out, she removes the other black cock from the strap on and cleans that as well. While she was cleaning the two cocks, you were cleaning the plugs, and once the plug you were wearing over night was clean and dry. Jane took it from you, spread lube over it and hand you bend over so she can reinsert it into you.
With yourselves and the toys cleaned, she holds the strap on and what is now her cock in one hand. While placing the other between her legs to stop the other cock from falling out as she's walking. When she reaches the bed she sits down, and reaches over to place her cock in the draw of her bedside table. Then tells you to get a pair of your white cotton panties, and cotton t-shirt bras from your plain lingerie draw, and the same from hers. Once you've done that she then has you go and get her jewel plug from the toy chest, and to bring the small box next to it to her.
When you return with the plug, she's already bent over and lubed ready for you to put some lube on the plug and insert it. While you do that, she takes the box from you and opens it, revealing 2 harnesses. One that is designed to hold dildos and plugs in place for a women, and the other designed to keep plugs in place for a sissy. Both are light pink with a few buckles and plenty of straps. The main difference is that the one for a woman has a padded cotton crotch panel that covers the pussy, while the one for a sissy does not. It instead has three straps designed to be looped into a chastity cage ring, similar to the current straps your wearing. Both are made from soft satin ribbons, and the broad crotch panel for your wifes harness has soft satin on the outside of it.
She has you strap the harness onto her, and tighten it, and then proceeds to do the same to you with yours. You both put on your bras and panties over the top of the harness. Jane then unhooks the school uniform from the wardrobe door and lays it on the bed, telling you to put it on. She then quickly grabs a pair of short heeled Mary Jane shoes for you, and a pair of white heels for her that you notice have a higher heel. Getting dressed in the uniform as instructed, with her slipping on her summer dress and heels, she does some light make up before turning around to face you.
"I know I said you were going to be fucked like a schoolgirl last night, and that didn't happen. It's mostly because I got too excited at the thought of you getting fucked and I couldn't wait. So today, we're going to go swimming. I'm sure with it being later in the day it will probably be busier, but we can't slack on our exercising like we did a few weeks ago. Now, while you're getting dressed, I'm going to pack our swimsuits for today, and then make us a quick brunch. Make sure you do your make up as I showed you Mary."
With her disappearing into the wardrobe, and then out the bedroom door. You finish getting dressed in the uniform and then do your make up. While not 100% confident, you do manage to do a good job, and are confident that you'll be fine in public. You then walk down stairs and join Jane in the eggs on toast she made.
Interruptions
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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.
- 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
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