Character: Dean x Reader
Word Count: 1350-ish
Name L/N=Last Name H/C=Hair Colour B/S = Body Shape Y/H = Your Height
A/N: Again, let
me know what you think! Ow and with the
mask I had something like this or this in mind, but of
course that’s up to your own imagination *insert rainbow*
Masterlist (including all parts of College
The end of the School year is getting closer and preparations are made
for next year.
You walked into the apartment and saw a letter lying on the floor,
clearly it had been shoved under your door.
It read that you could change your room and roommate if requested by this
Friday. You’d be put in the system and within 4 weeks you would get a response
about your new apartment and/or new roommate.
quickly read threw it and ignored it. You didn’t feel like moving, ever since
the football field with Dean, you two got along really well. The apartment was
okay as well, after Dean got a lock for the bathroom that is.
left the letter on the table for Dean to read. You had to get to work
surprise you hadn’t seen Dean that week. It was already Thursday or Friday
depending how you looked at it. You had to work again and got home at 2 in the
You heard Dean say and it scared the crap out of you, making Dean chuckle. “A
bit jumpy nerd?” You dumped your bag onto the table. “Yes Jock, you scared me.”
You teased back as you grabbed yourself a glass of water and walking towards
your bedroom when Dean stopped you.
You turned to him and oddly enough, he looked nervous. “What’s wrong?” You
asked and walked to the empty couch and sat down. You then noticed the letter
on the table. “Uhm. Have you read this?” He asked slightly shoving the paper
towards you. “I have.” You said, taking a sip from your water. “It’s due
tomorrow. Have you- I mean are you going to- uhm…” You smiled at him with
raised eyebrows. “I haven’t responded to that if that’s what you mean but if
you want to then we can ara-” “No!” You just looked confused at Dean’s
if you want to.” Dean said avoiding eye contact. “I could say the same to you.”
You said and Dean looked up at that, you thought you could see a small smile.
You continued. “Or we can leave it as it is?” “Yeah okay, if that’s what you
want.” He said, casually leaning backwards. You couldn’t help but laugh at his
not-so-casual reaction. He looked at you confused. “Dean Winchester, I won’t
leave you in this hell whole.” You said laughing and being over dramatic with
one hand on your forehead and waiving the other hand with your pinky sticking
You stopped laughing and dropped the act as you heard Dean ask that and looked
at Dean seriously. It stayed silent for a little while and you couldn’t help but
let your hand guide and rest itself onto his cheek. “If you’ll have me then
yes, I promise.” You said with a smile. “The rules still apply though.” You
said laughing and stood up with your glass. “I presume you’re not going
I was here first.” “Whatever.” You said rolling your eyes, walking to your
room. “Night Dean.” “Night Y/N.”
really quick, you finished your exams and Dean was going home for summer break.
He was looking forward to seeing his little brother.
decided to stay in the apartment over summer break. This was your chance to
make some extra bucks at Miss Martinez without having to make excuses all the
nearly end of the summer break. People would return in a week or two. Summer had
been relaxing-ish, you’ve worked a lot but that paid off too, so it was worth
arranged with Miss Martinez that you’d
have the first two weeks of school off. To get back into the study rhythm plus
to you your classes were critical the first two even three weeks, after that it
was all good.
just on your break at Miss Martinez, eating your lunch on the little balcony at
the back with one of the girls when another girl came to you. “Y/N there is
this guy who asked for you.” She said to you. “What do you mean, asked for me?”
You asked slightly panicked. Did someone know you worked here?!
asked, if available, for his Dom to be a Y/H, H/C haired, E/C eyed B/S woman.”
You raised your eyebrow. That is indeed pretty specific but then again you’ve
heard of clients who want there Dom’s to look like Jennifer Lawrence or even
You said talking the form. “Can you bring him to the room and tell him I’ll be
there in half an hour? Want to finish my lunch and get ready.” She nodded and
kind of kinks are you gonna play next?” The girls you were sitting outside with
asked as you looked at the form. The box ‘first timer’ was crossed and he had
the usual package. Nothing out of the ordinary. Tying up, teasing, orgasm
denial, was open to toys but no penetration. This is also why you loved the
form, at least now you’d know the subs whishes and therefor where to start,
like a short resume.
he’s a firsty, sub session is only for an hour.” You read out loud. “Aaaww,
those are always fun and easy.” She said kind of jealous. She was right though.
Those were the once that had your personal interest as well, they were usually
so innocent a.k.a. fun to toy with and as a bonus they were easy money.
your break and got yourself ready. You looked at yourself in the mirror,
checking your hair, corset, stockings, heels and touching up your make-up and
as last touch put on your mask. One last double check that your mask was well
placed and well knotted at the back. To you, everything was in place and
therefor good enough.
your way to your usual room, Marsha standing outside. “You are so lucky, he’s
so handsome.” You looked surprised, because let’s be honest, it’s not everyday
a really good looking guy walks in here but hey, no judgement here! Usually the
guys you didn’t expect it from were the best and sweetest.
you nodded to Marsha and made your way inside.
a.k.a. ‘office’ has a king sized bed, 1 poles at each corners, for tying subs
down. There was 1 closet the sub or dom could put there possessions in and 2
cabinets were you had all your toys stored in and a table and 2 chairs. More
walked in, the guy was faced against the closet, hanging up his jacket. He was
tall, short hair, alethic shoulders and upper arms but it feels wrong. His
features seem to familiar.
it off you and went threw your usual routine. “You can take all your clothes
off if you like and put them in the closet with your belongings, unless you
wish otherwise of course but if you do that beforehand that usually saves some
time since you’ve only got an hour.” As you said that you had walked to one of
the cabinets, making your preparations, taking out the condoms, handcuffs and
some extra toys you might think come in handy.
my mistress?” You heard behind you and you could feel yourself having a heart
attack. NO! This can’t be! This is not happening! You are wrong, Y/N! That just cannot be him!
turned around and could swear that you were hallucinating. You don’t know what
from but this just could not be
stood only in his jeans, in all his glory. He was just staring at you,
obviously waiting for his answer and service.
Winchester. Dean-Roommate-Winchester. Dean-Hot-Jock-Winchester.
Are you fucking kidding me?! Why hadn’t you looked at the
fucking name on the form before you came in here?!