An easy warm-up!

You enter the Pewter City Gym with a swagger, letting everyone know that you are going to conquer everybody who challenges you, first up is the only other trainer in the gym, a Junior Trainer (18) who you dispatch with ease, his Diglett and Sandshrew proving no challenge for your Bulbasaur.

"S-So w-what now?"

"Now you strip off and bend over..."

The Junior Trainer complies, telling you his name is Paul, you are grateful for the fact that the gym design with all the rocks blocks noise as you drop to your knees and apply some lube to Paul's virgin hole, making sure to give him a good amount inside and outside.

You then strip off, revealing your 8" Sissy Tamer which was fully erect in anticipation of claiming another cherry.

"When we are done, I want you to change the way you dress as well as your name..."

Before you give him a chance to respond, you ease your thick cockhead into his virgin ass, making him groan as he feels his hole being penetrated for the first time, once you'd fully sheathed your cock and had his bubble butt cheeks against your abs did you let him answer.

"A-Anything f-for-you D-Daddy..."

"Your new name is Paula and you will start wearing girls clothes, grow out your hair and start wearing make-up... You will also give me your phone number so we can hook up outside of the gym..."

He looked back at you and nodded, so you started fucking him, slowly at first before ramping it up, making him cum five times in a row hands free. He looked back at you with hooded eyes and begged you to breed his Sissy ass. You smirked as you reached into your backpack and pulled out a neon pink buttplug, telling him to suck on it for lubrication, which he did eagerly, coating it with a large amount of drool before handing it back to you.

Leaning forwards, you whisper in his ear.

"Before Daddy breeds you, Daddy's gonna mark you as one of his..."

Not giving him a chance to react, you lean over the left side of his neck and give him a deep hickey, making him moan and tighten his ass, triggering your orgasm as you moan into his ear, flooding his asshole with your hot, sticky cum. Once you'd finished cumming, you quickly replaced your cock with the buttplug, sealing your cum inside of your newest Sissy slut. Going in front of Paula, you offer him your cock to clean off, which he eagerly does, getting you back to semi-hard.

"Now go and get Brock Daddy!"