The Secrets He Kept -CH 14

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, Meg, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: Dean falls into old habits, alcohol as a coping mechanism, passed out drunk, scared reader, panic attack, some angst, fluff, and implied smut

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

Word Count: 2,539

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

Sam and Eileen announced they were having a baby three weeks after Dean and Y/N announced their engagement. News of Lisa putting an appeal came out and sent Dean into a dark spiral – Y/N had found him passed out on the floor by the bed.

She’d gone into panic mode and called Meg for help because she lived five blocks away and could get there faster than anyone. Dean had been fine thankfully but he’d finally admitted that he’d thought he was fine and stopped going to therapy – he’d panicked about the Lisa thing and gotten blackout drunk while Y/N had been at work.

She hadn’t seen Dean behave that way in three years but decided that she had to have a serious discussion with him.

The Secrets He Kept -CH 13

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, Meg, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: A wedding, and engagement, and baby news (it might not be who you think!), 

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

Word Count: 1,697

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

“So, Y/N you and Dean have been dating for almost six months now,” Meg was grinning, an evil glint in her eye.

“I’m aware of how long we’ve been dating,” she eyed her friends around the table wondering if they were all in on whatever Meg was about to say or if they would all be just as shocked to hear whatever came from her mouth.

The Secrets He Kept -CH 11

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, Meg, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: Y/N is put in charge of helping Dean sell his house. trials take place, 

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

A/N 2: This chapter fills my jacklesverse bingo square House of Broken Love by Great White

Word Count: 2,417 Masterlist | TSHK Masterlist

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

Y/N walked through the front door to find Dean packing a box, a wave of panic went through her.

Was he moving? Had she done something to upset him?

“Dean, what’s happening?”

“I kinda took over your place,” he murmured as he placed a couple of albums in the box. “I thought I’d be a better roommate.”

“Are you leaving?”

The Secrets He Kept -CH 10

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, Meg, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: Y/N is put in charge of helping Dean sell his house. trials take place, 

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

@deans-baby-momma thanks for your help with this one!

Masterlist | TSHK Masterlist | Word Count: 1,976

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

Dean headed to Austin to do some recording with a friend of his at a local studio there; leaving Sam and Y/N to get the situation with the house figured out.

“Dean wants nothing to do with any of her art,” Y/N explained to the crew of packers, “I worked directly with him to mark the frame or the wall to the left of the frame with a sticky note. If it’s pink, pack it and place it in the Cube, if it’s green it needs to be wrapped and placed in the U-Haul. The same identification system is in place for all home décor.”

The Secrets He Kept -CH 9

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, Meg, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: Y/N gets arrested, Sammy doing lawyer shit (ok maybe made-up lawyer shit)

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

@deans-baby-momma thanks for your help with this one!

Masterlist | TSHK Masterlist | Word Count: 2,417

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

Jody was silent just studying her, so she went on, “I know you and him have had run-ins but he’s a good man. I adore him. I’d never do anything to hurt Sam or Mary. She kinda was like a mom to me, the closest thing I was ever gonna get to having a mom.”

“I believe you but you still assaulted Lisa.”

“It’s a black eye, people get worse on a Friday night at the bar.”

“You and Lisa weren’t at the bar; you were in a hospital.”

The Secrets He Kept -CH 8

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, Meg, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: character in hospital, mentions of past abuse (emotional and physical), attempted murder, arrest, (legal mumbo-jumbo made up by me, sorry I'm not an attorney nor have i had much dealings with one in a court setting ... thankfully)

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

A/N2: this chapter fills my jacklesversebingo square for “When were you going to tell me? (prompt used 2x)

@deans-baby-momma thanks for your help with this one!

Posting a few hours early... remember I love you all

Masterlist | TSHK Masterlist | Word Count: 2,073

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

The next afternoon Y/N arrived at the door Sam had instructed her to enter, Cas escorted her to the end of the hallway that Dean’s room was in, “wait here until Sam waves you in. I’m going to ask her to step out and explain what she remembers from the last two days. Don’t worry I’m planning to take notes, but uh she has cooked up the idea that I’m assisting in the investigation and a PI of sorts so nothing I get from her today can really be used in court. However, if she says something to me that might tip something off, I’ll let the lead investigator know which line of questioning to lead with.”

“Castiel, thank you.”

The Secrets He Kept -CH 7

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, Meg, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: character in hospital, 

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

@deans-baby-momma thanks for your help with this one!

Masterlist | TSHK Masterlist | Word Count: 1,873

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

“I’m just guessing, but it’s the natural path, the bedroom was a mess; broken bedside lamp, the chair next to the closet was on its side, and several small items on the floor like they’d been thrown. The mirror at the end of the hall was off kilter like someone had bumped into it, the glass figurines Lisa keeps on the table in the hallway next to Dean’s office were smashed on the floor and then his office looked like a warzone. Sorry to be dramatic but picture frames were all broken or had the glass broken out of them, so was his tablet, his golf clubs were knocked over and I’m wondering if one was used on him. The cut on his face lined up with the shape of one of his awards that was laying on the floor in the office,” Y/N rubbed her temples, “Lisa was nowhere to be found and he was left for dead. Speaking of which where is she?”

Cas frowned, “she was reached but said she needed to finish filming her clip for tomorrow.”

The Secrets He Kept -CH 6

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: injured character, medical and police investigation (might be complete bs just go with it, lol)

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

@deans-baby-momma thanks for your help with this one!

Masterlist | TSHK Masterlist | Word Count: 1, 880

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

“Hey, do you know how to make a half-calf hazelnut latte?”

“Not yet,” she admitted. “I can take orders though,” she offered. 

Carol, Mary’s best friend and the shop’s assistant manager replied, “I’m totally ok with that,” she grinned and stepped back so Y/N could test her new login credentials.

“It worked,” Y/N smiled at the older woman, “hello what can I get started for you Mr. Burns?” she turned and asked a sweet man she now recognized as one of the “usuals.”

The Secrets He Kept -CH 5

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). 

Chapter Warnings: legal b/s made up by me, Lisa being horrible, Ketch being horrible, fluff and feels. 

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

@deans-baby-momma thanks for your help with this one!

| Masterlist | TSHK Masterlist

Word Count: 1,967  (look at that word count!) 

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

On his break between classes Sam called Y/N the next morning, and found that she was feeling better and had gone home and painted two canvases the night before.

“I forgot you painted.”

“Well, Sam that’s because I kind of did too,” she chuckled, “I never really sold many and then I dated Trevor – who told me that I was just slopping paint on a canvas and that wasn’t really art and didn’t make me talented so I stopped,” she huffed, “Sam – Dean needs our help to get away from Lisa. I don’t know how but she beat him up. He has giant bruises on his side.”

The Secrets He Kept - CH 4

Summary: You've known the Winchester family since you were very small. You love him, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff. Language! (you should just assume this with me. LOL).

Chapter Warning: Dean realizes his friend is struggling financially so he offers some help, Lisa finds out and isn't pleased, reader accidentally catches a glimpse of the marks left on Dean (he has a flashback of the event which is italicized between the two dividers if you want to skip over that part). 

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

A/N2: this chapter fills my jacklesversebingo square for "Adulting" will be in bold.

@deans-baby-momma thanks for your help with this one!

Word Count: 1,904 | Masterlist | TSHK Masterlist

The images on the cover are from IG and Supernatural Wiki and edited by me. Dividers were also created by me.

The following week Y/N found herself at home sorting through furniture and clothing she could list on the local marketplace to sell; she managed to sell a desk and a chair and an ottoman that same day.

With help from her neighbor, she was able to load them into the back of her SUV and within an hour she was back home checking her accounts.

The Secrets He Kept - CH 3

Summary: You've known the Winchester family since you were very small. You love him, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff. Language! (you should just assume this with me. LOL).

Chapter Warning: Y/N finally gets her interview with Kansas (yes that's a warning), Lisa shows up to work with a bandage, there's tension at work, Y/N's hours being cut mean money is getting tight

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

@deans-baby-momma thanks for your help with this one!

Word Count: 1,843 | Masterlist | TSHK Masterlist

The images on the cover are from IG and Supernatural Wiki and edited by me. 

The next morning Y/N finally got her interview with Kansas but couldn’t enjoy it because she just kept playing the previous night in her mind.

“I want to extend my gratitude to you boys for coming out here and chatting with me,” she grinned.

“No, we appreciate you,” grinned Ronnie Platt, “especially since you called all us old guys ‘boys’,” the band laughed.”

“Are you going to play us a song?”

“Sure, do you have a preference?”

The Secrets He Kept -CH 2

Summary: You've known the Winchester family since you were very small. You love him, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff. Language! (you should just assume this with me. LOL).

Chapter Warning: Reader witnesses an incident between Dean and Lisa, I can't think of anything else that needs added at this time so if I missed anything I apologize

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

A/N 2: Chapter 3 will post on Monday morning and will post weekly on Mondays to the end of May when you'll get a Monday and Friday post for this fic. Enjoy!

@deans-baby-momma thanks for your help with this one!

Word Count: 1,436 | Masterlist | TSHK Masterlist

The images on the cover are from IG and Supernatural Wiki and edited by me. 

By the time Y/N was finished speaking both of the younger women were standing and ready for a fight but Dean dragged Lisa out of the house with one last apology to his mom.

Sam glared at their friend for a moment before following his brother outside.

“I’m sorry Mary,” she sighed, sinking down into her chair and hiding her face in her palms.

Mary patted her shoulder, “not as sorry as I am. I love my son but he should have married you and not her,” she stood up and removed Dean and Lisa’s plates from the table.

The Secrets He Kept -CH 1

Summary: You've known the Winchester family since you were very small. You love Dean, you always have and you'll do anything to help your friend no matter the cost. You've helped Dean get his singing career off the ground but now that he and his wife, Lisa have moved back to Kansas and settled into a massive property you have started to notice some changes. Can you help him without ruining your relationship? 

Characters: Dean Winchester, Sam Winchester, Mary Winchester, Lisa Braden-Winchester, you/ Y/N, Jody Mills, Castiel Novak, Ketch, 

Warnings: Heavy angst, domestic violence (male receiving), friends to lovers, slow burn, some fluff, and lots of language (but it's me so you probably knew that already). This is a multi part fic so as usual if any other warnings need to be added they will be added to each chapter.

A/N: some of the things described in this fic come from what I saw with the experience a friend of our family had with his ex. Violence at the hand of a significant other is very hard to spot sometimes, but if you (no matter gender) are experiencing abuse please reach out. Many towns/ cities have a local group that can help you but if you don't know who to reach out locally or are concerned about privacy you can go to this website they have an option for backing out and deleting your browser history if you need the extra security. Please don't suffer alone. 

@deans-baby-momma thanks for your help with this one!

Word Count: 1,971 | Masterlist | TSHK Masterlist

The images for the cover and dividers are from IG and Supernatural Wiki and edited by me.

The pressure of nearly losing her job that morning was too much; at least that was the latest threat from her boss, Ketch.

“I mean it this time Y/L/N if Winchester doesn’t show up again your ass is on the chopping block,” he’d told her.

‘That’s what I get for telling him I had connections to someone that famous,’ she thought as she’d gotten ready to do the opening greetings for Wake-up Wichita. She’d only been on air for the past year and wasn’t the most popular with any of the staff, she only kept the position because she’d helped them get some interviews with a couple of celebs because of her connection to Dean.