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Chapter 44
by Wolf Keeper
Becoming a truly fucked sissy
Dominated by a machine
After your drink, you manage to rest for only a few minutes before Jane directs your mouth back to her cock. Just as you're taking it into your mouth, the machine gives several hard deep thrusts into you. The huge black cock grinding hard against your prostate withe each thrust and pull out. The speed and depth of each thrust is pushing you onto the cock in your mouth, making you gag each time. Jane is holding onto your head while you're being **** into this blowjob the fucking you're receiving.
"Oh my sweet Mary this is turning me on so much, and judging from how much precum your currently leaking. You're just as turned on as I am."
The more the machine is fucking you, the more you're moaning around the cock in your mouth. You're close to deep throating it, thanks to your wifes own thrusting of her hips in time with the machine. It then starts picking up it's pace, thrusting even harder and deeper, you barely remember that the machine done this to your wife. As the huge black cock gets pounded into you, it's pile driving motion triggers a massive orgasm. It's hard pounding and then slow pull back, thrust, and then hard pounding again.
As the long held edge of orgasm is finally allowed to crest, it feels like nothing you've experienced for. The rush of pleasure envelopes all of you in the orgasm. You shake all over, and if you weren't being held by the cock in your mouth, you would have collapsed forward. As it is, with the orgasms causing you to moan and cry out around the cock, your throat relaxs enough for your nose to end up pressed against your wifes groin. While you can't get hard due to the chastity cage around your clitty. You feel each pulse of cum being **** out of you with every thrust of the huge black cock that is still pile driving you through this orgasm.
"Oh my god my sweet Mary. Cum like the sissy girl that you are! Feel that huge black cock making you into the sissy girl I've known you to be since you told me you wanted to be my lesbian girlfriend."
Hearing your wifes words, as you're still being pushed and pulled between the two cocks in your. Your head is swimming in endorphins and you look up to see her looking down at you with love, excitement, and pleasure as her head tilts back. The blow job you're giving her cock is rubbing her clit thanks to a silicone set of nubs designed for this purpose. Her orgasming in front of you triggers your next, as the cock fucking you starts going deeper as well. Picking up it's pace, and now starting to pull fully out of you before driving back into you.
This orgasm them rolls straight into another one, as you experience your first multiple orgasm. The constant state of pleasure is making you suck on your wifes black cock with more enthusiam than before. Determined to make sure that she orgasms a long with you. The fire in her eyes as she sees you sucking harder, and actively making sure you press your noise up against her with every thrust forward of the machine. It turns into her orgasming again, as the **** of the thrusts of the machine and being translated through you sucking her cock into motions on the nubs that push her over the edge again. The machine slows briefly, then stops deep inside you, trapping you with two cocks in you.
"You love having two black cocks in right now don't you?.. The huge black cock in your arse making you realise just how useless that clitty between your legs really is. You feel why I orgasmed so hard from my own fucking can't you sissy?"
Barely able to comprehend her words, you can't help but nod your head as she stroking your cheek. She eventually pulls you off her cock and offers you a drink of water, which you happily accept as you realise the multiple orgasms have left you dehydrated. As you drink, the machine slowly pulls the huge black cock from you, causing you to cry out in a long moan.
"Oh my once innocent Mary. You're a slut for big black cock now, you realise that right? No sissy can get fucked like that and not be. Hell, no woman can get fucked like that and not be. I'm proof of that here, as you know I have a big black cock inside me keeping me stretched out. Look between your legs sissy, look at how much precum and cum you've released while being fucked. It's even further proof that you're a slut for black cocks."
You look between your legs as instructed, finally seeing the beaker she placed under you to collect your fluids. Barely able to make out the markings from being almost pleasure blind, you can see that you've almost filled the beaker half way with precum and cum. An there is still more slowly dripping from the tube.
"Almost time for the fucking to resume my sweet Mary. Looking at the gape you have right now, I can only imagine my pussy having that much gape. How cavernous I must have looked, and how inadequate you must have felt seeing it. I guess I'm just going to have to make sure my sweet Mary keeps getting her dose of big black cock now. Maybe we can get a second fucking machine and we both get fucked, does that sound good?"
While saying this, she's come back around the front of you, and gotten back to where you can suck her cock again. When you try to reply she shoves her cock back into your mouth, as the machine does a hard thrust forward in time with her. You realise it's time for the last 30 minutes of fucking, and you're already wondering whether you and her really are sluts for big black cock now.
The hard fuck
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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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