His & Her-Mione (Halloween)

 I think this is my first Lindsay Lohan caption, when I was a kid I wanted to be her so much! So now I kinda wanna do more. 

Being asked by my Mom to babysit for

Mrs. Booker, a younger Mom who led her

pilates class at the gym, was

embarrassing. I mean, who wants a

21-year-old guy to babysit for them? But

Mom said it was in exchange for free

personal lessons and if I wanted to have a

roof over my head while I continued to be

unemployed, I'd pull my weight here and

there. So I agreed, little did I know just

what an effect that would have on the

trajectory of my life.

Mrs. Booker looked like an OnlyFans

model. Always looking her best, she was

even flirty and floaty with pale dorks like

me. She was an inch or two taller than

me. Then I met her husband, a towering,

chiseled, dark mountain of a man. I felt

like a child standing next to him, it was

intimidating. Especially when his wife so

openly flirting with me in front of him.

Their kid was a sweetheart, he was

agreeable and well-behaved, even made

me consider being a Dad some day.

Moreso when I imagined Mrs. Booker as

their Mother. One day she turned up

shortly after her Husband left, and put the

kid to bed before pouring me a drink and

one thing led to another... We ended up

having sex in her marital bed, I thought I

performed quickly and awkwardly, but she

said I was just perfect and gave me an

extra 100 bucks and sent me on my way.

She continued to text me afterward, which

was... Really cool. But again, scary,

knowing her husband could probably kick

down my front door with little effort. She

continued to suggest things like shaving

my body and giving me little workouts to

do, I didn't know anything about that stuff

but if the hottest woman on the planet.

thought I should do it, it was probably a

good idea.

We fooled around a few more times, but

her Husband came home early, wel

managed to get dressed, but it was a

close one. She asked if I trusted her

afterward, and I let her put a cage over my

dick, to keep us from doing anything

naughty again since she had so much

trouble resisting me. It was unbelievably

frustrating to spend the day thinking

about her, her giving me a long, sensual

hug goodbye and then having to just go

home and not do anything about it.

Then one day, she told me that her kid

was really into Harry Potter, and was

going to be Harry for Halloween and

wanted me to be Hermione. I thought it

was odd that a kid so young would be into

Harry Potter, but whatever. It took some

convincing, teasing, and promises of

certain acts, but I agreed to get dolled up

as Hermione for Halloween. Mrs. Booker

excitedly said I had to practice a few

things beforehand. So she stayed home a

few days to have me do laps around her

house in 6-inch heels with a giant, heavy

pair of realistic breast forms glued to my

chest. She continued to tease me, saying

what a cute little slut I made for, seeing

myself with big boobs, a locked up dick,

completely hairless under the eyebrows,

my new slim form from the workouts, and

a pair of high heels was pretty troubling...

The day of, she showed me my costume,

explaining that the only adult size was

slutty Hermione, with a tight sweater

showcasing very prominent cleavage, a

super short skirt, and some knee-highs.

The heels I'm still not sure about. She did

my make-up and applied the wig to my

head. We took some fun and sexy photos

together, interrupted by her husband

entering the room in his costume. He was

shirtless, oiled up, in tight leather pants.

Wearing a domino mask. Mrs. Booker

insisted I take a few photos with him, it

was pretty emasculating taking photos

while eyelevel with a bodybuilder's pecks,

only that tall because I was teetering in

this pair of heels.

We went downstairs and I saw what was

supposed to be the Harry Potter to my

Hermione... Dressed as one of the dogs

from Paw Patrol and being taken by Mrs.

Booker's younger Sister for the evening. I

tried to figure out what was going on as

Mr. Booker's arm wrapped around me and

caressed my shoulder. Holding me too

tight to slip away as Mrs. Booker

explained that the Hermione thing was a

lie, they wanted a costume I could

believably be Tricked into wearing. The

real occasion was a Halloween party with

some of their special friends.

These "special friends" have apparently

been following my "progress" un

becoming the sissy pet they wanted to

turn me into. I tried to ask what but Mr.

Booker used his free hand to turn my chin

up and into a kiss, then moved the other

hand from his shoulder to my ass, only

guarded by the thin skirt and the striped

panties under them. I squirmed. Mrs.

Booker had moved in and began rubbing

my cage through the panties before

kissing me herself, then moving my hand

to Mr. Booker's crotch, feeling his growing

bulge, I instinctively ran my hand along it

to feel the length of it then pulled it away.

They told me that I was to put on a little

show for their friends, and if I did well I'd

be invited to more gatherings, if I didn't

want to, I was free to go, but the key to my

cage stayed with them.