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Chapter 8
by Wolf Keeper
Playing with toys
The strap-on
When the movie finishes, Jane gets up and takes your hand to have you join her. Picking up your dress as she picks up hers, you head to your bedroom while admiring the beautiful woman that you married and is currently in front of you. Walking into your room, she has you sit on the edge of the bed while heading into the wardrobe. You hear the toy chest being opened and then closed, then after about 5-10 minutes you she walks back into the bedroom wearing a strap-on.
While you don't recognise the strap-on, as you didn't realise she purchased one recently. You do recognise the dildo on the front of the harness, as it's the purple dildo that you've played with in the past by using it on her. It's one that is the same size as you when your erect, as you only play with it when you've been playing her lesbian lover. As her rules for when you're her lesbian lover mean you don't use your dick, and use toys like a lesbian would. Realising that the only reason she is wearing a strap on is that she intends to fuck you with it.
"I can see you've figured out that I intend to use this on you, and while I would imagine you're a bit nervous. We have discussed it in the past, and I thought our anniversary would be a good time to try."
Giving you a slight smile and slowly walking up to you, she's purposely exaggerating the swing of her hips which is causing the dildo to swing wildly in front of her. When she is finally standing right in front of you, she reaches for your hand and places it on the dildo. Opening the bottle of lube she's holding she has you open the hand on the dildo and puts some lube on it, then has you close your hand and start stroking the dildo as if it was a real cock.
"Give the dildo a nice handjob Mary as you want it to be fully lubed before it goes inside you. I want this to be a wonderful experience for both of us."
Gently stroking your hair as your stroking the dildo. After a few minutes of this, she has you move to the middle of the bed and lay down with your legs spread. Having you lift your hips she takes a pillow and places it under your hips. As your hips are raised she also pulls your panties from your hips and then takes them off you completely as you settle down onto the pillow. You then feel her pulling on the plug and she gently removes it from you. She then applies more lube to the dildo before she has you spread your legs further. Pulling the plug out of you and placing it on a towel on your bedside table. She positions the dildo at the entrance to your ass and slowly pushes it in, letting you get used to the size and feeling.
Placing her hands underneath your thighs, she slowly pulls on you as she gives a gentle thrust into you. Slowing working up the speed and depth of the thrusts as she builds up to a slow soft fuck. It is a strange senstion, but the feeling isn't unwelcome. With her slowly working up the pace, you start to feel a pleasant sensations from the dildo rubbing against your prostate. Letting out a quiet moan, Jane takes this as a sign to start fucking you harder and faster. With her increased speed and strength of thrusts you start to try and thrust back as you feel an orgasm building.
"I knew you'd love being fucked my precious Mary. That's it, fuck me back little sissy. Your clitty hasn't even gone hard, and you're moaning like you're having the best sex of your life. You love my cock don't you sissy?"
"Fuck me Babe. I feel so close to orgasm right now, please stroke my clitty as well. Fuck me and stroke me at the same time, please..."
Fucking you as hard as she can, she completely ignores your clitty, even with you begging her to stroke it. When you try to reach down and stroke it yourself she just grabs your wrists and stops you.
"No! You're going to cum from being fucked like a good sissy girl does. No stroking that clitty thinking it's the source of your pleasure. It's not, the pussy of yours that I'm fucking is the source of your pleasure right now!"
Continuing to moan and fucking yourself back against her, the sensations from your prostate are taking you so close to the edge of an orgasm. Just the tiniest touch on your clit would set you off, but you feel to weak to try and break your wife's grip. Leaning forward to give you a kiss, she briefly legs go of your hands to pinch and pull on your nipples. The sensation of this is enough to send you over the edge and your orgasm hard beneath her. With a long guttural moan you feel the orgasm spread through out your body, causing you to almost vibrate in the convulsions of the release. Looking down you see that you're just dribbling out the cum, your not even hard and it's just a flow from your clitty.
"Yes my love, cum for me. Let your sissygasm envelope you, and feel the sensations throughout your entire body."
Slowing down her thrusts and just gently fucking you. You look up at her smiling, her eyes filled with love for you as you come down from your orgasm. Looking down you see streaks of cum on your crotch & belly from you cumming. Your wife eventually stops her slow gentle fucking and pulls out of you completely. Drawing a moan at the sudden emptyness left behind, you feel a plug replace the empty feeling inside. You look over to the bedside table after the plug gets inserted and see the it still there. Looking at your wife she gives you a cheeky grin.
"The plug you were wearing needs to be cleaned, and I brought a new set of plugs to help with your anal training. Congrats Mary, you are wearing the next size up of plug."
Standing up, and picking up the plug on the side. Jane heads into the bathroom and returns after a few minutes without wearing the strap-on. She crawls into bed beside you, and then pulls you in to cuddle her. Not having enough mental or physical strength to resist, and wanting to cuddle up to her. You gladly welcome the cuddling, as shortly after you fall asleep feeling content and loved by her.
The next day
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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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