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SissyPrincessBrianna — Lolita Trainer Ashley

#crossdress #crossdresser #crossdressing #femboy #sissy #tf #tg #tftg #tgtf #pokemontf #pokemontg #tgtfpokemon #feminization #sissification #forcedfeminization #sissyprincess
Published: 2020-09-05 14:11:41 +0000 UTC; Views: 25549; Favourites: 119; Downloads: 0
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The Lolita School of Pokemon Training! Come join us and learn the new and exciting ways of battling our Trainer Classes will bring you!

Ash stopped reading the flyer after this part. ‘’Training my pokemon in a new way sounds awesome! I don’t know what a ‘Lolita’ is but I’m stoked to get some training done!’’

Ash noted down the address listed on the flyer and made his way to this new ‘’Lolita’’ trainer school.

Ash stood before the school’s gate and when he entered he was met by the receptionist lady.

‘’Welcome Trainer, I assume you are here to sign up for some of our classes?’’

‘’You betcha!’’ Ash replied excited.

‘’Very well. All I need is your name here, here and there and a signature at the bottom please. Then I will gladly escort you to one of our beginner courses.’’

Ash just grabbed a pen and signed at the spots the receptionist had pointed at. It probably wasn’t important anyway.

‘’Very good. I believe Miss Eva should start her class in a few minutes. I imagine she will have a spot for you as well, if we are quick.’’

‘’Then let’s go!’’ Ash said he was ready to sprint like a Zebstrika using flame charge.

Ash now stood before a classroom door as the receptionist lady knocked.

‘’Miss Eva I have a new student here, could he perhaps join your class?’’

‘’Oh but of course, I will always have a spot for a new face.’’

Ash quickly entered the classroom and was surprised to only see girls filling the classroom. But he was even more surprised by the outfit Miss Eva wore. A luxurious frilly dress with a big bonnet and ribbons and her hair was styled in pretty curls. She kinda looked like one of those old porcelain dolls.

‘’Hello there sweetie, we were just introducing ourselves to the rest of the class. I think this would be a perfect opportunity to tell us who you are.’’ Miss Eva said with a kind smile.’’

‘’My name is Ash Ketchum! And I’m gonna become the pokemon champion. I hope being a student here will make me and my pokemon even stronger.’’

‘’Very nice to meet you Ash. I will assure you that you will learn many things here. So you will become a strong and elegant champion.’’ Miss Eva said.

‘’Now then let’s get everyone into their uniforms.’’

Miss Eva revealed racks of dresses similar to hers.

‘’Wait I’m gonna have to wear THAT?’’

‘’But of course darling, this is the ‘’Lolita’’ Trainer school after all. It was clearly stated in the waver you had to sign before joining being able to join this school.’’

Miss Eva pulled a copy of the waver from her desk and gave it to Ash.

‘’By signing this I -blank- agree to following one whole semester at ’ The Lolita School of Pokemon Training’ or else will pay the school 50,000 Pokedollars for the time I had spend making use of the school’s resources. I -blank- also agree to wearing the uniform assigned to me by my teacher to fully learn the way of the Lolita Trainer.’’

Ash got a bit red when looking at the dresses. He really had to go through with this. He can’t cough up 50,000 Pokedollars like that.

‘’Guess I don’t got much of a choice, do I?’’

‘’Oh honey, I bet you will enjoy being a pretty Lolita girl and following the classes like ‘’how to be a proper lady’’ and ‘’Lolita Fashion 101’’ just as much as the more pokemon oriented classes.’’

Ash just got redder and while the rest of his classmates dolled themselves up. Ash got help from Miss Eva. She went all out to make sure Ash would enjoy her new look. Miss Eva picked a pretty pink dress which was one of her favorites and helped Ash into it. She grabbed a blonde wig and fashioned it into a pair of pigtails after she helped Ash with his make-up.

When Ash was all dressed up he minced towards a mirror to look at himself. To his surprise he liked what he saw. He loved the long hair tickling his shoulders, the lipstick covering his lips and the smooth silk that hugged his body.

Maybe he was actually gonna enjoy his time here. Maybe ‘’Ashley’’ would even stay longer than the obligated one semester. Maybe Ashley was gonna finish a whole year.



Rymaestro and I collabed and after some brainstorming we came up with making Ash into a Lolita girl. So after that I drew up the drawing and wrote the writing

Thank you to Rymaestro for wanting to collab with me ^^

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Comments: 14

gigaxwolf [2020-09-07 19:42:53 +0000 UTC]

👍: 1 ⏩: 1

SissyPrincessBrianna In reply to gigaxwolf [2020-09-07 19:45:07 +0000 UTC]

👍: 0 ⏩: 0

charreddragonchii [2020-09-07 18:40:00 +0000 UTC]

👍: 1 ⏩: 1

SissyPrincessBrianna In reply to charreddragonchii [2020-09-07 19:26:22 +0000 UTC]

👍: 0 ⏩: 1

charreddragonchii In reply to SissyPrincessBrianna [2020-09-08 17:42:18 +0000 UTC]

👍: 1 ⏩: 0

TerraZero20 [2020-09-06 10:26:07 +0000 UTC]

👍: 1 ⏩: 0

GoldenFweddy [2020-09-06 00:29:44 +0000 UTC]

👍: 1 ⏩: 1

SissyPrincessBrianna In reply to GoldenFweddy [2020-09-06 08:22:23 +0000 UTC]

👍: 0 ⏩: 0

PrincessAshley91 [2020-09-05 21:39:19 +0000 UTC]

👍: 1 ⏩: 1

SissyPrincessBrianna In reply to PrincessAshley91 [2020-09-06 08:22:50 +0000 UTC]

👍: 1 ⏩: 1

PrincessAshley91 In reply to SissyPrincessBrianna [2020-09-06 11:49:34 +0000 UTC]

👍: 1 ⏩: 0

BabyPhoebe1991 [2020-09-05 14:47:13 +0000 UTC]

I bet Ashley will stay for a lot longer than a year ^^ What does Pikachu think of this, though?

👍: 2 ⏩: 1

SissyPrincessBrianna In reply to BabyPhoebe1991 [2020-09-06 08:18:12 +0000 UTC]

👍: 0 ⏩: 1

BabyPhoebe1991 In reply to SissyPrincessBrianna [2020-09-06 15:30:04 +0000 UTC]

👍: 1 ⏩: 0