Disable your Ad Blocker! Thanks :)
Chapter 17
by Wolf Keeper
The lesson for today
A new uniform
"Seeing as you don't have work today Mary. I feel it is only appropriate I give you an experience that you didn't get a chance to have when you were a child. I was saving it for the weekend, but now is the perfect time."
Entering the bedroom, you see on the bed two neatly laid out sets of clothes. On top of the clothes are two sets of plain lingerie. Both are white, and look to have a bra, panties, and a camisole. Then you can see 2 blouses, 2 pleated skirts, 2 ties, 2 pairs of what you assume are over the knee socks, two blazers, and finally two pairs of moderately heeled Mary-Jane shoes.
"I have decided that we're both going to get dressed up as schoolgirls today. An as you know I kept the uniforms I had from when we were in secondary school together. We're going to be wearing actual school uniforms, and not novelty kind that you get at adult costume shops."
Realising you're going to be living out two fantasies today. The first being you having wanted to wear the girls uniform from secondary school, and the second it Jane's fantasy of having a lesbian experimentation experience with one of her girlfriends in school.
Sitting you down on the bed like yesterday. Jane picks a pair of panties and kneels in front of you. Raising your feet so she can slip them up your legs. Once the reach your thighs you stand up for her to slip them up the rest of the way. However, before she does. She picks up a panty liner from the bed, inserts it into the panties and pulls them up while tucking you into them.
"There we go, your little clitty can now leak all it wants. Safely tucked and not at risk of staining your panties like a bad girl."
As she smooths out the panties, she reaches behind you and grabs the plug and pumps it in and out a few times. This causes you to moan, as the increased size presses harder against your prostate with each press. You can also feel a pleasant sensation, like she was stroking your clitty from inside your body. The sensation only lasts while she's pumping it in and out, though she makes sure it doesn't actually get pulled all the way out.
"Oh, you enjoyed that far more than yesterday. Are you becoming a fan of anal my sweet sissy?.. Wanting to get fucked by me using one of my dildos perhaps?.. We'll get to that later on today, seeing as you're enjoying it so much now."
With each pause she makes, she pushes on the plug hard before pulling it back slightly. You're not sure what she means by getting to it later, as you're too caught up in the sensations to put 2 + 2 together.
"Now, stand up and grab my panties from the bed. You're going to put mine on me. We're going to dress each other today, alternating one peice of clothing at a time."
Giving you a grin as you stand up, she sits down where you were waiting for you to get her dressed in her panties. Picking them up, you kneel in front of your wife, and she raises her legs like you did. As you lift the panties up her legs, you can smell how turned on she is, it's intoxicating. As you reach her thighs she stands up and stops you. Then taking another panty liner she puts it in her own panties before you pull them up the rest of the way. You do the same as she did, by making sure to smooth the edges and ensure they are sitting correctly. However, she stops you when you go to grab her plug, tapping you on the nose and then pointing to her pussy.
Seeing the momentary look of confusion on your face. Jane grabs the back of your head and pulls your face into her crotch. She spreads her legs just enough to get your nose right against her clit, which she then uses to grind on for a few minutes. When she releases you, the overwhelming smell of her sex is making you feel punch drunk.
Standing you up, she reaches over to your bra and puts it on you. Even though you can't feel it, you do see her tweaking and playing with the nipples beneath the fabric with one hand. The other has made it's way down to the front of your panties, where she's rubbing against your clitty, as if it were a real clit.
"Don't you wish that these could be real at some point? That we could both enjoy the sensation of playing with your breasts. You feeling everything I'm doing to the fake ones right now?"
Just as the sensations of her playing with your clitty are starting to overwhelm you. She stops. You swear, for a brief moment. You could feel her playing with your nipples as she speaks. It's like the combination of her words, actions, and the feeling from her rubbing your clitty all combined. Tricked your brain into making it feel real.
Regaining your senses you reach over to pick up the other bra. You slide it up her arms, reach behind her to clasp it. Then before she can move to pick up the next item of clothing. You pull down one of the cups and start sucking on her nipple. As you do that, you rub her clit as well. Deciding to take charge briefly and make her feel overwhelmed with sensations. Hearing the moans and feeling her hands running through your hair as she holds your head.
You do this for a few minutes before stopping. As you stand back up straight, you see her eyes are closed and her mouth open as she slowly comes down from the pleasure.
"Oh you naughty sissy... I'm definitely going to have to spank you for that!"
That same impish grin from yesterday appears on her face after her statement. She then picks up your camisole and helps you with it before you do the same with her. Then she picks up a blouse and and goes behind you. As she's sliding it up your arms from behind, she starts to kiss your neck and shoulders. Once the blouse in on she reaches around you to do up the buttons, while still kissing your neck. Repeating the same for her, with the same neck kissing and slow button of her blouse. The sensual dressing makes the sexually charged atmosphere of the room almost reach boiling point. From the light spanks you both gave each other putting on your skirts. The rubbing up and down your legs when putting on your over the knee socks. You tickling her feet while helping her put her Mary-Janes on. Something that she promised to spank you for on top of the earlier promise. You do up each others ties, and help each other with the blazers. Then checking each other over to make sure your uniforms aren't messy.
With you both dressed. Jane directs you to sit down at her vanity next to her. She then teaches you how to do your own make up. While you make some mistakes, you get there with her help. Resembling the same younger version of your mother you saw yesterday. You both put your hair into high ponytaills, and she ties a white ribbon in your hair around the base of them with a big bow.
Looking at the time now that you've both finished dressing. You've taken an hour since getting out of the shower to dress each other. Leaving you both in a very horny state, and you still have most of the day left.
A day as a schoolgirl
Disable your Ad Blocker! Thanks :)
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
You can customize this story. Simply enter the following details about the main characters.
- All Comments
- Chapter Comments