Authors note: I feel like I am on a streak with Hazbin hotel and Helluva boss stories and I keep it up with Characters I didnt use before, like in this I will use Sir Pentius as Haru and Alastor as the Barron from "The cat returns"

Summary: Shy and awkward teenager Penny thought she was doomed to live a normal boring life until one day she rescues a owl demon who was actually a prince named Prince Stolas. As a thank you King Pidmon asks that Penny Marries his son!

Transforming into a male snake demon Penny must find the courage within to change back and escape the plan with the help of the Windigo Barron Alastor

Prologue Pennys rough day

In a city known as Pentagram tokyo there is a small house, almost like a cozy dinner like area that one thinks as a place to have tea. Watching from the window was a tall and thin windigo like statue that is red as blood, dressed as a gentleman.

Male voice with a slight static accent: If you find yourself troubled by something mysterious, or a problem that's hard to solve there's a place you can go where you always find help, you just need to look for it

It fades to white as a alarm bell chimes as it goes to a cozy little house where a figure presses the snooze on its alarm clock. Revealing to be a young girl of 14 with fair skin, amber eyes and a blush mark on her cheeks and dark yellow hair as she moaned awake dressed in dark black with yellow striped pjs as she moaned covering herself under her quilt hugging a egg like creature plushy she made…

Before she gasped awake "Not again!" She yelled in a slight victorian accent as down stairs a dark skinned figure dressed in a suit with green eyes and messy green hair tied in a ponytail looked up "Are you up yet?" He asked though had a odd accent to him

Girls voice: I'm up I'm up papa Zetsiel

The girls said as back upstairs the girl was now dressed in a black with yellow trip skirt with long red and yellow striped socks and black and red shoes, black long fingerless gloves and a orange and red stripped crop top with a long sleeved cropped top over it as she hastily made her bed as she tied her hair into twin French blades and a purple ribbon in her hair as she grabbed her school bag as she ran down stairs but not before looking one last time at herself…but ran off "What ever" she said as she ran down stairs where she saw her adopted papa sitting down for breakfast before he went to work as a museum curator "Hi Papa" he said "Honestly Pentious why do you bother to set a alarm clock?" Asked Zetsiel as 'Pentious' blushed "papa its penny *grabs a wrapped bento box* but anyway I gotta go" he said "oh to bad you dont have time to eat" he said teasing his son eating a egg on bread as Penny moaned annoyed but ran out but not before peaking "That's just mean papa" she said as Zetsiel chuckled "Have a nice day" he said as Penny ran outside running pass two wild Imp demons lounging as she ran down the road to get to school in pentagram tokyo as she was fast but near the over past where a team of baseball players were running for training over as Penny noticed "Oh my shoe" she said as he tried to get it but the players were running pass her as she tried to get pass "Oh please excuse me?" He said but they kept going as he got annoyed. "Ohh" he said

In his school class was starting as a teacher was giving a lecture as Penny tried to sneak in…but "Pentious we can see you sneaking in so just get to your seat please" said the teacher as Penny flinched and stood straight up "Yes sir" she said as everyone laughed as she sat behind her best freind Angel Dust "Busted" he said as Penny blushed more so his real name was jumped as her crush a beautiful messy haired red head named Cherry laughed as she just looked down. Later many students were playing up on the roof top as Penny just leaned on the side with Angel Dust wishing things would be much better then his boring life or she wasnt just shy as the title of the story appeared.

"The windigo returns"

However Pennys thoughts were interrupted as she was struck by a ball as she looked over her shoulder as Angel dust laughed at her face.

School soon ends as Penny just let her feelings out angery at her day at what has happened "Its just not fair, first I had a bad morning and then everybody laughs at me in class, even Cherry was laughing wasnt he?" Asked Penny as she and Angel dust walked out with Angle dust having finish a lecross practice "Yeah pretty hard" he said as they stopped in a corner as Penny just vented her feelings "Why me? Why all these bad things happening to me?" She asked as Angle hummed "Maybe its some kind of weird omen Pen like your life is gonna get a whole lot worst real soon" said Angel as they continued on as Penny deadpanned "Thanks Ang that helps alot.

Meanwhile at a nearby small grocery store hopping out was what looks like a owl no bigger then half a basketball with grey and black feathers as it hopped out with a box wrapped in a package which was noticed by a old lady named and her pet cat "That's odd never seen him?" She said as her cat meowed as the owl walked down the path the same path as Penny and Angel "Why are you worried about what Cherry thinks?" Asked Angel "I just think she is so cool, so confident so brave especially with her amazing pyro techniques" she said "Tell him" said Angel "What? No what if she has a girlfriend or boyfriend then I look like a jerk" said Penny "Well she does a freshman really cute" said Angel as Penny moaned as Angel giggled as she chased him "Then why are you telling me to flirt with him!?" He said "Because I wanted to have a good laugh when she blows you off" teased Angel as the owl walked up to them "You are terrible!" Said Penny "Anyway Cherry is cool but I think you are not ready for her yet, besides my Husk is much cooler" said Angel as Penny raised the lacross stick to strike Angel for teasing but stoped seeing the owl with the package.

"What the heck was that?" Asked Angel "A bird burgler?" Asked Penny as they watched the owl look both ways "Where does he think he's going?" Asked Angel confused "Hay dumb bird! You'll get killed!" Yelled Angel dust as the Owl just avoided him and crossed as the light turned green as a truck pulled up "Oh well its just a bird" said Angel dust as Penny got worried "This dosent look good" she muttered confusing Angel as the owl continued as the truck seem to come closer as the owl dropped his package as he tried to pick it up but failed a few times "Ahh what's he doing?" Asked Angel panicking as Penny as if on some instinct dropped her bag and with the lacross stick ran across the street as Angel dust yelled at her to stop.

Time seemed to slow as the truck tried to slow down as Penny scooped the owl and his package up in the net as he ran pass the truck as Angel watched in awe as the stick broke on a pole as they managed to get on the other side as Penny fell into a bed of flowers avoiding Angels screaming at the truck driver as he tried to cross the street.

With penny after panting a bit he looked up "Oh little owl I hope you were ok because that was close" she said but gasped as the owl…was no longer a owl, but a humanoid owl demon with four eyes dressed as a prince as he stood up and brushed off the dirt as he looked at Penny with a smile "That was quite the brave act you performed on my account I am extremely grateful" he said with a bow "I hope that you are not injured yourself" he said but poor penny was just stuttering shocked at the owl…no demon that can talk "Well then I dont mean to be rude but I am in a hurry I'll return later to thank you properly" he said as he bowed again and in a poof became the owl chick as he took the package in his mouth "Tha-thats ok" said Penny but gasped watching the owl chick walk off as Angel ran up to her "Penny" she said as the owl demon walked around a corner and was gone as Angle picked up the lacross stick "Well so much for your stick but at least you rescued that stupid bird" he said as Penny gapped in shock "It talked" she said Confusing Angel "That owl turned into a humanoid and spoke to me" she said but Angel didnt believe her believing she struck her head as Penny looked again…and thought it was just her imagination 'it has to be not real…right?' She pondered

Authors note: nice start right?

Next chapter Penny meets the king of demons Pidemon and learns she had saved his son Stolas and was to be rewarded…though in the most oddest of ways as she is slowly turning into a male snake demon!