Becoming a Diapered Sissy (Patreon)

It was hard to say exactly how it came to be this way.

It just started out as a joke when your girlfriend made you try some of her fantasies that involved you, tied up and gagged on a chair, watching her getting f ucked by her lover. She really insisted that you wear a diaper because it was ''part of the thrill'' to have you there, splattering on yourself while ''a real man satisfied her''. 

Of course it got worse when you had to use the bathroom for real and your girlfriend found out you had completely soaked your diaper when she finally checked on. Somehow this seemed to spark something within her that you had never seen before. 

She kept joking about putting you in a diaper at night, calling you her ''little bedwetter'', teasing you by fake worrying that you might ''have an accident'' when you went out. Asking if you wanted her to bring a diaper in her purse ''just in case.'' Going as far as tugging at the back of your pants in front of her friends and telling them ''just making sure he's still dry'' before they all burst into laughter. 

Then she was no longer satisfied with your regular s e x life and started seeing other men more and more often, asking you to sleep in the guest room. She did her best to involve you in the act, telling you how much she was thinking about you lying down in the other room and that it turned her on. But she didn't want you to cross paths with her lovers, so she decided it was part of the fantasy that you'd wear a diaper when a ''real man'' was over, so you didn't have to use the bathroom and he would never know you're there. She had a whole ritual around it, when someone was supposed to come over, she'd get you ''ready for bedtime''. Pick out some jammies for you and diaper you at least an hour before he arrived. Tucking you into bed so she could get herself ready for him. Later in the evening when he'd be gone, she would come back and cuddle with you for a little bit. 

If you had a wet diaper on, she'd reward you by rubbing the front and give you an o rgasm before changing you into a dry diaper for the night. If you were still dry, she'd punish you by making you sleep alone in the guest room. So you quickly learned to not feel ashamed at wetting your diapers and even appreciating your late night rewards.

After a while she started bringing women over too. Strong women who could easily beat you up. She decided she was tired of men who never satisfied her completely. And she decided she was tired of you being one of them. 

It was a slow but steady change. It started as nicknaming you ''missy'', ''princess'' and ''baby girl'' to buying you some very childish panties to make you wear under your grown up clothes during the day. By that time you were diapered every night no matter if a woman came over or not. She had also switched your white diapers for pink ones with bows and princesses on them. She said they suited you better as such a soft little bunny. 

You accepted all that without too much complaint. You loved her so much you just wanted to please her. You felt so grateful to have a beautiful woman like her in your life and didn't want to lose her. You were glad to still be a small part of her s e x life as her diapered little sissy cuck. A part of you was also getting used to loving all of it. 

One time, one of her women came home a bit early while you were sitting on your bed in just your little girl panties, waiting for your Mommy to come put your diaper on you. When the doorbell rang she made you open the door for her mistress and greet her. The woman kept teasing you and ordering you around. Just as you were coming to serve her drinks, she tripped you and you spilled everything on the floor. As a punishment she put you on her knees and started s panking you so hard that you actually genuinely wet yourself all over her lap. She was furious of course and s panked you even harder, so much that you started bawling like a baby and apologizing while yelling you needed diapers. 

Your girlfriend took you at your word and the next day your panties were all gone and replaced by girly little Pull-ups with butterflies on them. You couldn't believe it, your whole wardrobe had been sissified and now you were expected to wear Pull-ups all day and diapers every night. Never trusted to use the bathroom like a big girl. She told you that from now on you had to ask permission to ''go potty'' and that she would slide down your Pull-Ups for you, no matter if you were at home or in public.

In a couple of months you had transformed from a young man to a little girl, sucking your thumb in your Pull-ups while your girlfriend was having s e x with other women. Then came her friends to babysit you while she was out. They all treated you like a little sister. Some were nice and allowed you to pee in the toilet normally. Some were mean and kept making up excuses not to take you until you ''had an accident'' in your Pull-ups just so they could diaper you for the rest of the night.
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This story was written by pullupfiction

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Special thanks to ABDreams for the picture!