Rupert had been introduced to the idea of clowning from his friend Groo after he designed what would eventually became known as the 'Pastel costume'.
The Meerkat-Rat had been hesitant about the idea but slowly warmed up to the idea over the next 16 months, he had even learned to juggle in that period (which he became rather proud about).

It was a couple weeks later when he obtained an invitation from Spectre for 'Pastel' to join as an act at his 'Starburst Circus'. He had noticed that the flyer seemed to only depict Pokemon, but he was so fluttered by the offer, he decided to head down and meet up with the ringleader.

A few days later he finally got around to visiting Starburst Circus, smiling nervously as he greeted with the pink fairy-typhlosion ringleader. After some introductions and interesting conversing (including the mild surprise from Rupert that he was offered a position despite not being a Pokemon), it came to the signing of the contract.
Rupert was very pleased after the discussion with Spectre, so was all to happy but to fill out the paperwork pledging himself to the carnival life. With that all in order, the next step was Pastel's initiation.

The initiation given to Rupert, now officially running under his performance alias Pastel, was a rather strange one.
To start with Spectre rolled out a purple rattata plush suit and instructed Pastel to put it on. The reasoning was something about fitting in and feeling more at home amongst all the Pokemon employed by the circus. As he was a rat hybrid, the rattata seemed the best fit for Pastel.
The next part was a celebratory tea party, which included a dress up. Pastel was a bit timid to the idea of wearing a dress, but after some reaffirming words from the ringleader, he decided it was all in good fun and would be best to join into the spirit of the initiation process. In his mind Rupert knew cross-dressing was a small guilty pleasure- a guilty pleasure that had developed after a few unexpected sissy situations in the past. With this the case, he figured he might as will indulge. Spectre helped slip a cute pink and white dress over the rattata suit, the faephlosion having already jumped into a dress ready for the tea party.

After some relaxed snacking and tea drinking (the ringleader having to help Pastel due to the limited dexterity of the plush suit), it came time for the tour of Pastel's trailer. Pastel was stunned at the paint job on the side, decorated beautifully in the colours of his clown outfit. He headed inside excited, but got stuck getting into the door. After some help getting out of the plush suit, he hope back into the trailer, but was rather bewildered and bashful as he saw a very frilly sissy design within the trailer which was to be his living quarters here at the circus.
Pastel was blushing heavily as he explained to the ringleader about the set-up. Spectre assured him that it wasn't permanent, some workers were meant to set-up the trailer in the same pastel theme as the outside of the trailer and had run out of time before he had arrived.
During all this discussion of the trailer, Pastel didn't realise some interesting changes to his form after taking the plush suit off. Despite being a normal rattata suit, Pastel seem to have started taking on some features of an alolan rattata. Overtime, the change seemed to continue towards more and more of his appearance becoming that of an alolan rattata.
After some thinking and come peculiar yet compelling conversation from his ringleader, the newly formed rattata decided to accept the sissy look inside his trailer. Embracing the guilty pleasure, he had not expected would be a factor in this new circus life he has freshly signed up for.

Spectre seemed to be very convincing through the whole initiation process, the ringleader managing to encourage his newest act to embrace a guilty pleasure and help Pastel cope with the shock of the unexpected change of becoming a pokémon. It was for the best, Starburst Circus was home to pokémon, it would have been awkward being the only non-pokémon. It was almost like the ringleader had planned and manipulated it to be like this along.

Here we see Pastel a few days later, trying on his new clown outfit that the ringleader faephlosion had freshly ordered for him ahead of his premier in the circus ring. The new outfit was similar to the outfit Groo has originally designed, but repurposed into a dress format. On the outside Pastel was so thrilled and honoured, but inside he hold a swirl of giddy bashful butterflies in his gut. Although despite the bashful feelings, he was glad to be the newest pokéclown on the block at Starburst Circus.

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Spectre and Starburst Circus concept belongs to  SpectrePaw

Art drawn by  tattasratnest
Original artist submissions:
FA - http://www.furaffinity.net/view/30309028/
DA - https://www.deviantart.com/tatta-do.....ress-783734038