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Chapter 43
by Wolf Keeper
Fuck prep
The warm up
When you enter the bedroom your nerves start to get to you. Being fucked by the huge black cock is not something you want, but Jane wants you both to share the same experience. Walking past the machine and into the bathroom, your wife helps you strip off to fully clean you out. She has you bend over so she can take out the plug, and while pulling it out you can't help but moan thanks to the pressure and feeling on your prostate.
"Did someone enjoy me taking this big plug out? Then you're going to love how the huge black cock is going to make you feel like a woman being dominated. Now, lets get this done quickly. I can't wait to see you getting fucked."
After you've been cleaned out, she puts the large plug back in to make sure you stay stretched out. Walking you back into the bed room, she has you help pull the machine back a few meters. There is no need to have your shoulders pressed against the vanity stool, as you're going to be fully cuffed in. Kneeling down in front of the machine, she gets your ankles straped in, then has you lean forward until your shoulders are touching the floor like hers were. She then takes your hands and holds them one at a time getting you locked into the wrist cuffs.
While not an uncomfortable position at the moment, as the soft rug on the floor is giving you some padding. You wonder how much being fucked with change how comfortable you are. Jane stays out of your line of sight as you hear her doing a few things behind you. You hear the sound of a bag being opened, followed shortly by a box. Then you hear the sound of running water after she went into the bathroom. Unsure of what she is doing, you hear the sound of the machine starting up and a clunk as the ankle and wrist cuffs lock.
Walking back in front of you, you look up to see your wife sporting a big black cock the same size as the first one you have. Though this one is certainly not the same one. The first one was more dark brown in colour, where this one is completely black like the huge black cock attached to the machine. Giving you a wink and a smile, she then moves behind you before you feel the large plug being removed again. Then the machine makes more noise as you feel the head of the huge black cock get positioned at your arsehole. You then feel and hear Jane make an adjustment to the machine before the you no longer feel the cock at your arsehole.
"Now, a few things I want to tell you. First as you saw, I am wearing a different big black cock than the normal one. That is because I brought a second one for tonight with the idea of having you suck it while you were getting fucked. Which is going to happen, as you've already sucked a cock of this size. I've also still got our first big black cock in my pussy, incase your wondering. Now, I'm starting the profile now, and you're going to go through the same warm up, then fuck, and after fuck phases of the program I did. Here goes."
The machine springs to life again as you feel the huge black cock press against your arsehole. It's not as painful as you thought it would be, but there is alot of pressure as the head is insistent on getting in. You get pushed forwarded by the machine until the restraints stop it. Then the head pops in and the machine stops, and like with how it went with Jane it pushed further forward again and stopped. The pressure and sensations on your prostate are sending shockwaves through you. You couldn't stop the moan when the head popped into you, and you couldn't stop the bigger moan when it went deeper still.
"Embrace this my sweet Mary. You're going to receive the fucking of your life so far, and I'm getting so turned on by the thought of watching it. Hell, I wish we had a second machine and another huge black cock so we can be fucked at the same time. I love you my beautiful Mary, and I want you to enjoy being my darling sissy wife right now."
Stroking your cheeks as she says this, leaned down to look at you in the eyes. Her eyes filled with love, as the machine goes further again with another loud moan from you as you feel the ridges of the cock rub and press against you prostate. Then it pulls out completely, and you can feel the build up of an orgasm coming on, just from the slow movement of it's pull out. When it thrusts back in and reenters you, you feel like you're seeing stars as the **** of entry is stronger than before, and the deeper penetration.
Eliciting a strong, guttural moan from you as it reenters. You hear the machine stop while the cock is still logged inside you. Then you hear the sound of a wrapper being torn open, something being taken out and then a pair of scissors, and several other sounds from behind you. It's not until you feel Jane unrolling something on you that you realise it's a condom, with an unsual weight too it.
"I've paused the machine during the warm up, as I wanted to make sure we capture all the precum and cum you're going to be leaking while being fucked. So I'm wrapping a small condom over your clitty that has a tube attached to it. It leads into a narrow necked flask like you'd see a scientist use. This way it'll all leak through the tube into the beaker and we can see just how much precum and cum you make from being fucked. Now I'm going to release the cuff bar from the machine so I can raise you head up for you to take a nice long drink. I need you to stay hydrated."
You feel the bar get released, and you kneel up as much as you can. Jane then offers you a bottle of water with a straw to drink from. You drink about a quarter of your 2 litre gym water bottle before she takes it away. Then she sits herself in front of you, the big black cock attached to her strap on pointing you in the face, and her legs wide open. You then see her pick up her phone and resume the profile. The machine starts to pull out immediate upon resuming it's program. Then as the next thrust pushes back into you, with your mouth open from moaning she guides your mouth over her new cock.
The slow spit roasting continues for several minutes, each time the machine pulls out and pushes back in. The feeling of every fake vein on this huge black cock that rubs against your prostate has you trying to thrust back and forth on it in time with the penetrations. The machine finishes it's warm up cycle before pausing again. Pulling you off her cock, she then offers you a further drink from your water bottle as you realise that after the warm up, you're on the edge of an orgasm and it's not even started fucking you properly.
Becoming a truly fucked sissy
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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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