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Chapter 30
by Wolf Keeper
New Workout clothes
Getting dressed
Her having now sprayed the makeup sealant around the forms. You're effectively trapped with the breast forms on now. Having already explained to you during the last two weeks that the adhesive for the forms can last up to 2 weeks before it starts to ****, causing the forms to start to peal away naturally. You hope that the remover for the sealant arrives on Monday as expected, or going to work on Tuesday will require an explanation.
You sit up on the bed, and as you do you feel the familiar weight from two weeks ago of your breasts tugging on your chest. Taking the offered baby pink sports bra, you slide your arms into the straps and clasp it close in front of you. Feeling the sqeeze from the bra. Your wife has pulled on her own bra before she bends you over to insert the plug.
"In keeping with our experiments, and with trying new things this weekend. We've got larger plugs to wear. I got a pack of three plugs during my planning, with the intention of us both sizing up over time. The one you've been wearing recently is the smallest of the pack, this is the next size up. It's going to have plenty of lube, and I'm going to work it slowly inside you. Let me know if there is any pain though, as I don't want it to hurt you. I've got the normal one here as well, just incase."
Feeling a a small tube and then a cold squirt of lube go inside you, you brace yourself for the plug. {Wife_name} places the tip of the plug at your entrance with what you can feel is even more lube on it. She then begins to give it a firm steady push to get it inside you. Feeling yourself giving to the plug, you try to relax as much as possible to get it in, but it's harder than the previous. After another 3-4 minutes you feel like Jane is about to give up before you finally stretch just enough and it pops into place.
This plug feels much larger inside you than the previous, and puts alot more pressure on your prostate. You can feel the pleasurable sensations of it being inside as you stand up. Looking down at your wife who has a pair of baby pink thong panties ready for you to step into, you notice something odd. Your clitty is fully erect, and there is a small bead of precum on the tip, which itself is not odd. What is odd is that you can't feel your clitty, or that bead of precum on the tip. You feel completely number at the moment.
"Jane while I know you're set on me wearing the plug all day. We might want to take it out, as I can't feel myself right now. I can feel the plug, and the pleasant sensations it's giving me through my prostate. I just can't feel my clitty though, and it's concerning me."
{Wife_name} reaches up to your clitty, and starts rubbing the underside of the head gently. Something that would normally have you weak at the knees by her doing that, is giving you utterly 0 reaction right now.
"Wow, this is crazy. Alright bend over, I agree that it's best we not leave it in you if it's going to do this to you."
You bend over again and feel her grab the base of the plug. When she starts to pull the plug out you get a massive jolt of pleasure as it pushes against your prostate. You also notice looking down, that your clit has now deflated completely. While she's trying to pull the plug out, everytime it rubs against your prostate it's sending a wave of pleasure through you. It's like you're getting fucked again, but this time you're not. However, your clitty is still remaining soft.
You reach up to rub it and see if you still get any sensation. When you hold the head in your fingers, you feel more pleasure from it than you ever have. It's like the sensations are being amplified 3 fold over what they normally are. This combined with your wife still pulling and occasionally twisting the plug sends you into a full body orgasm. Causing you to collapse forward as you orgasm, your wife still holding onto the plug ends up falling forward with you as it still won't come out. Your bum has a tight grip on the plug and it's not letting go.
Seeing you touch your clitty, but not expecting the full body orgasm. When Jane recovers from being pulled forward, she immediately moves to be able to see your face and make sure you're okay.
"Sweetie are you okay, did I hurt you pulling on the plug to hard?"
While you're not quite sure why you orgasmed so hard, you manage to recover enough to reply.
"I'm fine. The sensations from you pulling and twisting the plug, combined with me just holding the head of my clitty to check for sensations, sent me into a massive orgasm."
Looking relieved that your not hurt, she strokes your cheek giving you a smile. Moving out of your line of sight, you feel her getting behind you.
"Well, you can definitely tell you orgasm hard. You apparently managed to squirt quite a sizeable amount onto the end of the bed when you fell forward. You also look to still be leaking cum from your clitty."
Hearing her get up and go into the bathroom. She returns with a towel, and a soft flannel to clean your clitty with. After placing the towel under you while you were lifting your hips for her to do so. When she touches your clitty with the damp flannel you can't help but moan loudly. Your clitty is still hyper sensitive, and every touch is bringing you closer to the edge, but never taking you over it. Once Jane has finished cleaning you up, she helps you stand up again, before kneeling it front of you grabbing the panties she had previously.
"Well as your little clitty is obviously still functioning, and you can feel it now. I see no reason to take the plug out as it's obviously not caused you any harm. Now, step into these panties so I can pull them up, get you tucked into them with a panty liner to help with the precum. Then we're going to finish getting you dressed in the rest of your work out clothes. I see no reason to change our plans today after your orgasm."
Realising you have **** in the matter. You step in the panties as directed, and she does as stated. You get tucked back in with a thick panty liner. She then hands you a white with baby pink trim small jacket/top that just about reaches your waist, and has you zip it up to where you've got some cleavage on show, but not too much. Then has you step into again matching baby pink leggings that she pulls up for you, making sure that the front seam almost gives you a camel toe, and the rear seam definitely goes up your bum. She then has you sit on the bed so she can put a pair of trainer socks, and a pair of white with baby pink trim trainers on you.
With you now fully dressed, she hands over her plug, which you can tell is a match in size to the one you're currently wearing, and bends over. Following the same procedure for her plug as yours, you find the lube bottle and squirt some inside her, then place a generous amount on the plug itself, before you insert it into her. While it doesn't take as long to get it into Jane you do eventually get it in. You then pick up the baby pink thong she had prepared for herself and do a once over of her outfit. Looking at hers to yours, she's got you matching jogging outfits, from underwear to overwear.
Getting her dressed as quickly as she did you after your orgasm. Going over to her vanity, she applies your make up first, then does hers. Finally you both tie your hair into high pony tails and look in the mirror. You definitely look like a lesbian couple wearing matching workout clothing. You both tidy up the bedroom before heading down stairs to grab your water bottles for your run.
"Well Mary, it's now or never, and I'm going to make sure that it is now. You're way too cute when dressed for me to let you stay in doors all the time, and as your body currently looks like that of a smoking 22 year old. We're going for a jog along our regular route. Should anyone question why I'm not with you, then you let me do the talking. While your body is looking all woman right now, your voice will need some work before we can have you speaking."
She takes your hand and leads you over to the door. Picking up your keys as she picks up hers, she opens the door for you both and nudges you outside. Locking it up, she then starts stretching out ready for the job while you do the same. You know you're not going to avoid this, as her mind is dead set on this happening. You're thankful that you live in an area that doesn't have you interacting with your neighbours much. You hope that with your garage being tucked into the side of the house, and the drive way having enough of a turn to when you get out of the house your not visible from the street. That your neighbours don't know what you look like well enough to sus that it is you running with Jane.
The morning jog
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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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