Nanny POV

I started with a bang in the morning. I sneaked into Alex’s room without waking him up; he was exhausted and slept super deep. By the time he opened his eyes, I had finished cuffing his legs and arms to his bed.

“Oh my god, please no!” He cried up.

“What’s the matter? You don’t even know what is coming.” I laughed and pulled a suppository from my pocket. “This is a vitamin suppository I made with your mom’s help. It is extra-large, so it will be difficult to push in, but the size guarantees it will stay in.”

“Why? I don’t need vitamins!” Alex resisted.

“Of course you do! What else would I put inside you? The butt plug stretched you out nicely yesterday, so you are ready for this.” I inserted and pushed the medicine inside him. He shrieked and begged me to stop.

“I need one more minute!” I told him. “The suppository turned out to be too big, so I need to wait until your ass accepts it.”

Thankfully, I worked the pill inside 3 minutes later.

“Now lay here until I found something for you to wear today.” I rummaged around the house and encountered a pretty skirt, a frilly blouse, and a large enough pantyhose for Alex. By the time I returned, Alex had pissed on the bed.

After a bit of spanking and cleaning up, I turned Alex into a decent human being – a female specifically. He looked – weird, but I concluded he would pass as a female; unless you look too closely.

“Let’s go to the park now. I must show you to everyone, my dear Alex or Alexandra!” I teased him as we walked out of the apartment.

“Anita, can I do something for you so that I don’t have to do this?” He groveled while tearing up.

“Yes, you can! You can give me the best girl impression imaginable. Your penis is small enough to make you a girl, so now you just have to act like one.”

Alex POV

The walk to the park was super embarrassing. Thankfully, there was no one there, and Anita got bored quickly.

“We are not going home yet,” Anita told me. “Let’s visit an old friend first!”

We arrived at Alice’s place. Alice was an old friend of both of ours from school. I don’t think I saw her for years. Based on how she looked at me, I did not want to see her ever again.

“Ah, you are so cute! I love your skirt!” Alice clapped as we entered her apartment. We sat around the kitchen table and started eating and drinking.

Anita had sunk into some deep gossip with Alice while I tried avoiding eye contact with both of them. Instead, I chugged several cups of tea. I figured I should use the bathroom soon.

“Don’t be silly. A well-behaved lady like you can’t use the bathroom at someone else’s place,” Anita smiled. “Alice, I think we have to leave now. Alex will go all over himself in a few minutes. I don’t want to dirty your floor.”

“Of course, I wouldn’t want to stop you guys – I mean girls – from doing your thing.” Alice chuckled and said goodbye.

“What do you mean going all over myself in a few minutes? I don’t have to pee that much; I can hold it until we arrive home!” I argued as we descended the staircase.

“I said nothing about peeing. But the laxative Alice and I put into your tea makes sure that you wouldn’t last on the number two front.” Anita informed me. We barely stepped out of Alice’s apartment complex when I released my bowels. The mushy, brown liquid covered my pantyhose, even reaching my shoes. The shoes – covered in disgusting mud – made a ‘plop-plop’ sound for the rest of the trip.

“I hope you realize you ruined a perfect panty. I will reduce your allowance to cover the cost of replacing it.” Anita warned me as she removed and threw out the female clothing. I remained silent, but my eyes betrayed me: all I had, was hatred for her.