****These characters are not mine. They belong to lovely miss Cassandra Clare. Only this crazy, twisted plot is my demon spawn. Mwahahahahaha. Thanks for reading!******

~Remember…this shit is rated M for a reason~

Sorry for the delay in posting. Life happens. I'm kinda excited to see the reactions to this chapter. I'm sure some people won't be happy but just hang with me. The story is progressing. Either way, don't forget to review! Also the playlist on Spotify for this series has been updated. Just search for reppinda5o3 Send My Love/Hello/Water Under The Bridge Fanfics or here is the version of the link the FFN will actually let me post! h-t-t-p-s : / / open dot spotify dot com/user/1235861650/playlist/11pzLPQKBJ6BiTw8zkcWXM?si=Luh-d3jpQymFNhWygsx5xA

Don't forget to remove the dashes in the h-t-t-p-s part, take out the extra spaces and change the dots to periods!

Story Song:

*Adele - Hello*

Chapter Songs:

*Chris Brown - Should've Kissed You*

*Craig David - 7 Days*

*Boys Like Girls - Be Your Everything*

4 Months Later

Clary woke up on Saturday morning and looked around, momentarily freaked out, not recognizing where she was. She then felt a heavy arm laying across her stomach and remembered that she was in a hotel room with Simon. Maryse was in the middle of having her home redecorated and Simon's loft just so happened to have had a pipe burst a couple days before that flooded his whole place so it was in the process of being fixed and cleaned up.

The arm tightened around her and pulled her back into a hard chest. The voice behind her mumbled something that sounded a lot like "come back to bed, it's early" so she snuggled back in and almost instantly fell back to sleep.

The second time she woke up, she was alone in bed. She touched the sheets next to her and they were cold as if no one had been lying there for quite some time. Clary got out of bed and went to the bathroom, hoping to find Simon but the door was open. She relieved herself and put her robe on, heading to the living room of their suite where she found a tray and a note. She lifted up the lid and was surprised and suddenly famished when she saw a plate of strawberry cheesecake pancakes. She picked up the note and read:

Clary,

Please sit and enjoy your favorite breakfast, have a luxurious bath with your favorite bath bomb that I set in the bathroom and put on the outfit you'll find waiting for you in the wardrobe. I will be back for you at 11:30.

Yours,

Simon

Clary was extremely curious about what was going on. It was a special day for them but Simon had never done anything like this before. Sure, he got her takeout from her favorite diner or even planned dates for them but in the year they'd been together, he'd never been so secretive. He tried to hold back on the surprises because he knew Clary liked to know what was going on around her. Maybe he was just trying to do something nice. She already knew they were set to go to the museum. She wasn't sure what was going on but when he got back, he'd better be prepared for some badgering because she was determined to get the information out of him one way or another.

The start to Simon and Clary's relationship was an interesting one and honestly she was surprised that after being with him for this long, she still wasn't feeling trapped.

Flashback

Simon and Clary had known each other for almost 4 years. They'd met when she was still in medical school and was part of a group that was consulting on a case, back when he was still an assistant ME. He'd immediately been drawn to her and taken her under his wing, showing her procedures and techniques that she wouldn't learn until the following year and letting her perform them herself. Simon was 5 years older than Clary and at first she'd seen him kind of like a big brother. They became good friends and spent a lot of time hanging out when she wasn't in class or working at the hospital. He would quiz her and help her study for exams. They would go out on weekends to the movies or stay in and spend the night playing old video games. Mags had Alec and even though she loved them both, she sometimes ended up feeling like a third wheel, especially right after they got married. KK was in Chicago, working at C.A.E. as a Junior Engineer and even though they talked and she visited, they weren't as close as they used to be due to the distance.

When Clary graduated and started consulting all over different areas, Simon made sure to recommend her whenever he could. He knew how amazing she was even before she graduated and got her board certification. By that time, she was spending a lot of time at the NYC OCME which was great for Simon because he'd stopped seeing quite as much of her since Alec and Mags' adoption ultimately went through for their daughter, Gracie.

Finally, a year ago, the Chief Medical Examiner retired. It was unexpected but was inevitable due to a severe health condition and even though he didn't have the most seniority, Simon was offered the job. He graciously accepted and became the youngest CME in the history of New York.

That night, Clary and a few of his fellow assistants took him out for drinks to a local bar, not too far from work. They kept feeding Simon shots and since he wasn't much of a drinker, he'd actually lost count after the 4th. But all the alcohol in his system made Simon brave. He'd loved Clary almost since the moment he met her and decided in his state, that he was going to tell her how he felt. He asked her to come outside with him and when they were both alone, he looked at her face and all of his words disappeared. Rather than standing there like a drunk idiot, he sweetly pressed him lips to hers, pouring all of his pent up emotions into the kiss. Clary stood there, stiffly…not kissing him back but not moving. He abruptly pulled away and looked into her gorgeous emerald green eyes where he saw confusion and maybe reluctance? Before he could do or say anything, she was hailing a cab and was gone.

Clary avoided him like the plague for the next few months. She would take cases away from the NYC OCME or if she did take a case in his building, she'd come in and work it while Simon was in a meeting or when he wasn't in the building. She ignored his phone calls and text messages. He was worried he ruined their friendship and no matter how bad he wanted her, if it meant losing what they had, it wasn't worth it.

Simon was confused but he supposed he should've expected the reaction. In all the years they'd been friends, he'd seen her go through men like water. She seemed to be really into them at first and then something would go wrong and it would be over before she even had a chance to introduce them to her friends. Simon was hoping that he would be the one to break that pattern but it was seeming more and more like wishful thinking.

One day, Clary came into work, thinking Simon wouldn't be around but as she was setting her things down in the office she used when she was at the OCME, he walked in behind her and shut the door, locking it behind him so they wouldn't be disturbed. The look of surprise on her face upon seeing who'd trapped her had Simon rushing the words out before she could look for a way to get around him and escape.

"Clary, if I ruined our friendship by kissing you, I'm sorry. I've been wanting to do that for a long time and never had the courage but I was drunk and you looked so beautiful and I just couldn't stop myself. But if this is how it's going to be…with you ignoring and avoiding me…I just want things to go back to normal," he rambled, quickly.

"Simon," she sighed. "…I don't exactly do long romances. I'm sure you've figured that out by now. I have…intimacy issues from past relationships and there are some lasting scars that I don't know if I can ever recover from. I tend to run when things start to get serious and the last thing I want to do is hurt you. I just can't trust anyone like that anymore because whenever someone holds my heart in their hands, they seem to always find a way to crush it. I don't want to hurt you but I just can't set myself up for that kind of pain again."

He walked up to Clary and wrapped his arms around her, resting his chin on top of her head. She tensed, momentarily before burying her face in his neck and holding him close.

"You aren't going to hurt me, Clary. We're friends first, before anything else. While I'd love to give a relationship with you a shot, I understand your reservations. But know that if in 2 months or 3 months or 5 months or 10 months, you decide you can't do this…no, it won't be a pleasant experience, I'm only human…but, what I'm trying to say is it won't ruin our friendship. I would never hold it against you. I know what I'm doing and if you feel even a fraction of what I feel then I think we should go for it. Maybe I can even prove to you that not all men are out to break your heart."

Clary loosened her grip and pulled back slightly, looking up into his soft brown eyes. She wasn't sure if she should risk it. They had a great friendship and she wished that was enough for him; she really didn't want it to come down to her fight or flight response kicking in per usual and at that moment, it felt like too much to hope for that it wouldn't but he was a great guy. She had known him a long time. They were a good match. He treated her well. He was someone she could be herself around and she was attracted to him, with his curly and slightly too long, brown locks, his 5'11", toned frame and his boyish smile.

When she gazed at him, she saw someone...maybe not necessarily that she trusted with her heart but definitely someone who probably deserved it. She wanted to believe him when he said they could retain their friendship, even if it didn't work out. Simon was that kind of guy. She wasn't sure it was the right one but she'd made her choice. Clary got up on her toes, pulled Simon's face down to hers and covered his lips with hers.

At first, Simon didn't respond and she thought maybe he had changed his mind but then he kissed her back with so much force, she had to double check to make sure it was actually still Simon kissing her. She hesitated for a moment and he must've sensed it because he quelled his hungry kiss and began placing short, sweet ones on her lips. When he finally pulled away, still holding her in his arms, he said, "I have a good feeling about this...about us," and then he nuzzled his face into her hair. Clary felt content. Maybe this could work after all.

That day was the start of everything between them and yet it wasn't. Nothing had really changed at first. Simon tried not to be too affectionate because he was afraid he would suffocate her. When Clary figured out what was going on, she picked a day they were out exploring New York City and made every effort to set his mind at ease, teasing him about treating her like glass. He then jokingly responded by trying to smother her as they were walking, causing them both to have a laughing fit on the sidewalk as strangers stared at them like they were crazy.

After that, it got a little easier. There was a lot of hand holding and cuddling and kissing but they had been together almost a month and hadn't had sex yet. Clary was going out of her mind. She never went any serious length of time without physical contact from the opposite sex.

Simon came over one night to watch a movie, like he'd done many other nights and they cuddled up together on the couch. He began rubbing his hand up and down her arm and placing kisses behind her ear. Clary took it as a sign that he was ready to move to the next stage of their relationship and thought he would finally make a move but by the time the movie was over, he was getting up to put on his jacket so he could head back home.

Clary was having none of that and frankly, she was tired of waiting. If she wanted things to move faster than a snail's pace, she supposed she would have to initiate first contact. So when Simon turned to kiss her goodnight, she saw her opportunity and took it. She attacked his lips with such ferocity and hugged her knees on his hips, pinning him up against the door before he knew what was going on. It definitely took him by surprise but his hands were kneading her ass over her tight yoga pants in seconds and she could feel his hardness exactly where she wanted him.

Simon reversed their position and she brought her legs up to wrap around him. He held Clary up against the door, ravaging her mouth with equal fervor and grinding into her, forcing loud moans to escape each of them into the other's mouth. She slid his leather jacket from his shoulders and then proceeded to rip open his shirt, not bothering to unbutton it, causing small pieces of plastic to fly everywhere. Their lips finally separated long enough for Clary to direct him to her bedroom and he carried her in there, laying her down on her bed. The rest of their clothes were removed in no time and Simon went to work, worshiping every inch of her body like he'd been wanting to do for years. The first orgasm she had, she came so hard, she squirted, which was something that hadn't happened to her in a very long time. Not since...she shook those thoughts out of her head. Simon pulled a condom out of his wallet and put it on him before Clary pulled him down on top of her.

When Simon was finally seated deep inside her, it felt right. She still knew she wouldn't be able to completely trust again but she knew how she felt about the man currently taking her to the peaks of ecstasy and it was a feeling she'd almost forgotten existed. Clary soon climaxed, a long orgasm that seemed to never end and he came right after.

Simon rolled off of her and they gazed into each other's eyes for a long time before moving. Clary was completely sated and happy while Simon was both of those things but also a little shocked she'd launched herself at him, proven by him bursting out in laughter as he laid in bed next to her. When he explained to her what was so funny, she joined in and defended herself, citing her impatience to get him into bed. That only made him laugh harder and caused Clary to pout, adorably. Simon kissed her forehead, where a crease had formed and then her plump lips. Really, he'd just been unsure of how to broach the topic. He made to get up and dressed so he could leave, not wanting to crowd her, but Clary asked him to stay. She hadn't had a man in her bed for actual sleep in a very long time and wasn't positive she would still enjoy it but figured it was worth a try. They both crawled under the blankets, naked, Simon pulling Clary close and they fell asleep almost instantly.

End Flashback

Clary, being so curious, practically inhaled her pancakes and rushed to the bathroom to enjoy her bath. She tried to relax as she assumed Simon expected her to do but it was hard when she was so anxious. She did manage to spend a half hour pampering herself. She also spent the time shaving and washing her hair.

When she finally got out of the tub, she wrapped herself in a fluffy white towel and walked to the wardrobe where she found a beautiful sleeveless, green wrap dress hanging and her favorite pair of black suede Manolo Blahniks with the 4 inch heels. She decided she had better do her hair and makeup before she put on the dress so she took her time blowdrying and straightening since she still had an hour before she needed to be ready. Clary applied some light makeup; just some blush, eyeliner and mascara. She slipped on a black lace bra with matching thong, garter belt and a pair of sheer silk stockings, knowing that the set was Simon's favorite. The dress fit her like a glove and the heels went perfectly. Clary figured he must've had Mags' help because this had her best friend written all over it.

She was just finishing up as she heard the lock click and Simon came waltzing back into their room. He was wearing a gray button up shirt and black pants with a black leather jacket. He looked absolutely sexy and Clary wondered why they were leaving the room when she could be undressing her boyfriend and they could be spending the day in bed while ordering room service. Apparently, he was having the same thoughts because the next words that came out of his mouth were, "fuck, Clary. I knew that dress was made for you. If I didn't have plans for you today, I'd unwrap you right now." He pulled her in for a deep kiss. "Come on, we have somewhere to be," he said, grabbing her purse from the chair and hurrying her out the door.

Their first stop was The Met. Clary's second calling was art and if she hadn't fallen in love with science and forensics, that's exactly the direction her career path would have taken her. Whenever she got the chance, she visited every art museum she could get to, whether it be in New York or any other city she traveled to. Clary was particularly fond of The Metropolitan Museum of Art and visited every time they got a new exhibition. Simon was more than happy to take her. He loved to see the light in her eyes whenever she came across a piece that she loved.

They spent more than a few hours scoping out the museum before hopping in a cab and heading to the Brooklyn Academy of Music to see Love and Intrigue on Broadway. Clary had never been in the time she had lived in New York and Simon wanted to share the experience with her. She enjoyed the show more than she could've imagined and was beginning to appreciate surprises like she never had before. Simon then took her to The River Cafe, an upscale restaurant with a beautiful view of the water where they enjoyed a luscious dinner of strip steak and potatoes paired with a sweet red wine. They took their dessert of peanut butter soufflé to go.

In the cab ride back to the hotel, Simon held Clary close as she rested her head on his shoulder. She really had been blessed with a perfect day. She nuzzled into Simon's neck, biting it affectionately. He turned to capture her lips with his, wishing with everything that he had that the cab driver and New York traffic would move faster.

When they got back to the hotel, they barely made it back into the room before Clary was taking Simon's clothes off. Clary grabbed Simon's cock and pumped it a few times before pushing him back on the bed. She peeled off her dress hearing Simon's intake of breath as he took in her body.

"You're so beautiful."

"I picked this one just for you."

She kicked off her shoes and unclipped her stockings before turning around and bending over while slowly stripping off her thong. Her bra was next and ended up on the floor somewhere behind her. She climbed on top of him, straddling his waist. Simon sheathed himself and she sunk down onto his thick member, causing both of them to groan.

"God damn, Clary. I've been waiting for this since this morning. You're always so fucking tight." Clary bit her lip and started moving up and down while bracing herself on Simon's shoulders. He took a nipple in his mouth, sucking on it and nipping it with his teeth before switching to the other one. Clary sped up her movements and it didn't take long for her to clench down around him, milking the orgasm out of Simon as well.

Clary lay across Simon's chest as they were both recovering in the afterglow; Simon softly stroking her hair and Clary playing with his light smattering of chest hair. Simon pulled Clary's lips to him and placed a sweet kiss on them with her returning it just as sweetly. Simon watched her and took in how peaceful she looked with nothing but the glow of the city as their background. All of the sudden, he reached over and opened the drawer to the nightstand next to their bed. He urged Clary to sit up and she did but stared at him in confusion. She pulled the sheet up so it was covering her chest and rested her back against the headboard. He looked at her seriously but with nothing but devotion in his eyes.

"I was going to do this earlier but I lost my nerve and now looking at you like this, I can't let this day pass without getting this off my chest. Clary, I know a year may not seem like a long time but we've known each other for what feels like a lifetime. I was originally gun shy about rushing you into this relationship because I didn't want to scare you off but you surprised me by being the one to take charge and initiate almost every step we've taken. Now it's time for me to initiate the next step. Clary, I love you. I think I've loved you since I first met you. You're beautiful, kind, intelligent, generous, hard working and warm. When you want something, you go for it and I admire you so much. Every day I spend with you is not only like being with my lover but also being with my best friend. I know when we first got together, you were worried about handing your heart over to anyone because you were worried that the person you gave it to would break it but I hope I've proven to you that I'm not that guy. I don't want to rent your heart, I want it to be mine. Not just today, but for all the days. Will you please do me the honor of marrying me?"

Clary was speechless. Her mouth opened and closed multiple times before any words came out. She couldn't help but think back to another proposal she had received years earlier from a certain man who also claimed to love her and that had been the beginning of the end. She wanted to believe it. Simon was a good guy but she thought he was a good guy too and look how that turned out. She didn't know if she could rely on her own judgement despite being sure Simon was the most honorable man she had ever met. She wasn't sure what to do. She could feel tears coming to her eyes and she tried desperately to hold them back.

"Simon, I don't know what to say. That is one of the sweetest things that anyone has ever said to me. You mean the world to me. I love what we have and you're right, I don't think you're a guy who would break my heart but I'm still not sure I'm the girl who can trust herself to hand it over even if I trust you." Simon's face fell and Clary hated that she was the cause. She had to make sure he understood. "I'm not saying no, Simon. I just can't say yes yet. I'm sorry." As much as he wanted to call Clary his wife, Simon had prepared for the possibility that she wouldn't be ready. He was hopeful that after a year together that he would've proven himself but she said that having faith in him wasn't the problem. She had been seeing a counselor for the last 5 months or so and they were both proud of the progress she'd made with her trust and self esteem issues. Simon looked down at the hands she was wringing in her lap and pulled her to him, kissing her head as he held her.

"Okay, Clare. I'll wait. As long as you need, I'll wait."