Imagine Simon taking your virginity (smut)
(Here is the SImon imagine as promised :D So I hope I got this request right and you all like it :D I tried my best making it realist so I hope it’s okay and it makes sense :3 Yay for Simon! Gif not mine/found it on google/credit to the original owner.)
From the start of the outbreak, you found yourself lucky enough to be part of group of people.
They called themselves the Saviors and although they weren’t the kindest
they had saved you while you were in a dire situation and you were eternally grateful for them.
As you joined them, their leader Negan, had wanted to marry you and offer you countless of gifts.
He made you uncomfortable and you tried rejecting him but he kept insisting until one of his men had stepped up and explained to him that you probably needed some more time among them to understand what being his wife would include.
Negan had chuckled and eyeing you up and down, he said “Well, aren’t you lucky…Simon here wants you to try the free trial before you take the fucking deal! And you know what…I’ll let you try it…”
He then looked back to Simon and continued, “Simon! You stood up for her. Then deal with her and make her understand that she’s hot to me and that i’ll give her whatever she needs if she marries me!”
Simon nodded and with that Negan left the room along with the others, leaving you and him alone.
You eyed him from head to toe and he turned back to look at you. He smirked and said, “What are you looking at?”
You jumped hearing his voice and got nervous from his comments, making you stutter when you answered him.
“I-I was only checking you out! I mean looking at what you look like…Whatever…”
He noticed your nervousness and started to laugh at the way you spoke to him.
“Checking me out? What? You like what you see? What’s your name again?”
He slowly got closer to you and it made you back away. Apart from telling him your name, You didn’t know what else to say and simply ended up being backed against the wall.
He towered over you and eyed you just as you did. Shaking his head, he then said, “Well Y/N…if you do like what you see…You’re in luck…because of you, i’m stuck babysitting you…”
As soon as you heard the word “babysitting” you got pissed and pushed him away from you and said, “I’m not a baby! So you’re not babysitting me!”
He laughed even harder and just couldn’t seem to stop soon enough.
You told him to stop but he just couldn’t and suddenly looking at you in disbelief, said “You?! Not a baby?! How old are you?!”
Pouting at him and crossing your arms, you told him, “I’m 23…”
He laughed even more and approaching you, he put his arms around your shoulder and said, “Alright, whatever Y/N…Whether you’re a baby or not…I still need to show you around!”
He ended up doing just as he said and strangely you felt more comfortable with him than any of the others.
Soon enough, the more days you spent there the more you grew to like his company. He was the only one making you laugh with his comments and you felt safer around him.
You counted yourself lucky to have made a good friend out of one of them and so did he.
He liked talking to you and felt entertained whenever you were around. Slowly, it was obvious to everyone he had a thing for you.
From the way he looked at you to the way he would spend his day teasing and making fun of you, it was clear he didn’t just see you as a friend.
Even Negan saw it, in him and you as well, and although he wanted you for himself, he felt generous and thought of setting you two together.
One night, he approached Simon and told him he was allowed to pick a girl as long as they accepted him.
He grinned thinking of you and was certain that you would say yes.
He got to your room and knocked on the door. You opened it and saw him smiling.
“Hey, Simon. Is there something wrong?”
He leaned in the door frame and shrugged.
“No…There’s nothing wrong…Can I come in?”
You were startled by his request and you looked both ways outside your door, looking to see if anyone was around.
He chuckled and walked in your room anyways.
“Stop! What if someone sees us? It’s late at night…we shouldn’t be together!”
He chuckled and just went on to jump on your bed and lay there. You quickly closed the door and went to grab his arm to get him off the bed.
“Simon, you can’t stay here! If Negan finds out he’ll kill us!”
He laughed and ended up pulling you towards him instead. You fell on top of him and he suddenly flipped you to land on the bed.
He held you tightly and you tried to get out of his, out of fear Negan would find out. He then cup your face and said, “Calm down…Negan knows i’m here…”
He looked at your features with a slight smirk and continued, “He told me I could pick a girl tonight…and as long as she says yes…I can stay…”
You felt your heart beating faster and yourself starting to get warmer and sweating. You knew exactly what he meant.
“And…you’re choosing me?”
He nodded and smirking, inched closer to you. You panicked and dodged him and managed to get out from his arms.
He got startled and sat up on the bed looking at you in disbelief. Before he could say or do anything, you put a hand to his chest and explained to him.
“I-I like you Simon…I really do…but i’m not sure if i’m ready…”
He was relieved to hear you say that you were fine with him but then got curious about the other part.
“Not ready? What do you mean not ready?”
You got even more embarrassed and couldn’t look him in the eyes to tell him what he needed to know.
“I mean…I’m a…I’m a virgin alright!”
You felt like you just died telling him that and turned away from him to cover your face in your pillow.
His eyes widen in shock and slowly started to grin and laugh.
“You’re joking right?”
When you didn’t answer him, he realized you were telling him the truth and somehow wanted to be with you even more.
He got closer and turned you over to look at him and said, “Alright…You’re a virgin…so what? I still like you and want you…besides you won’t be one after tonight…”
He got closer and instantly you felt like you wanted him as well. You nodded and kissed him back to reassure yourself and him of what was going to happen.
His tongue danced with yours inside your mouth and you felt his hand reached downwards your body.
He groped you tightly and just the way he liked, making you gasp and get a little more nervous.
As he heard you, he slowly he moved away to mark you elsewhere and and whispered, “I’m not gonna hurt you…I’ll make you feel real good…alright…”
From his tone, you could tell he was genuine and nodded to let him know you were fine.
He held you tightly to him while his other hand slowly reached down to your pants.
He unzipped your pants and still kissing you started to rub you. You felt your body getting warmer and the sensation of yourself getting wetter as you felt him touching you.
He made you whimper and as he heard you he backed away to completely remove your pants and parted your legs to open them more.
You got shy and tried to closed them but he set himself in between and kept making you feel light waves of pleasure for the while.
He chuckled looking at you biting your lips to keep quiet and just had to tease you even more.
“Y/N, let me hear that sweet voice of yours…Cause if you keep quiet that means i’m not doing a good job…and that means i’ll have to work a little harder…”
You slowly felt his finger entering in and out of you while his thumb kept circling around your clit.
He grinned looking at you struggle and just motivate him to keep doing what he was doing. He noticed your hips slowly rising and knew you wouldn’t be able to keep it in for long.
He put a hand to your thigh to pin you down and went on faster. He bent over to you to kiss you feverishly and in rough tone asked “Are you ready?…Are you ready to come? For me…tell me…”
You felt him going faster and clung onto his shirt tightly and just nodded eagerly.
He went faster with his fingers and finally made you tremble and shiver in pleasure and let you ride it out.
As he felt you relax, he chuckled and removed his fingers and went on to remove his clothes quickly.
He then got to you and help you out of your shirt. As he soon as he removed it, you just wanted to kiss and hold him tightly.
He did just as he wanted and fell back on the bed with you. You wanted to touch him and make him feel as good as you but as you reached for him, he stopped you and shook his head.
He looked into your eyes and whispered, “No…Don’t…as much as i’d really like it…This is about you…and making you feel good…not me…alright…”
As you nodded, he parted your legs again and settling himself between them, he started to stroke himself to get even harder.
You felt your stomach slightly turn and anticipated to feel him. However, at the same time you got worried an wondered if you were going to be able to feel some pleasure after the pain.
He made you feel good until now and you didn’t want that feeling to go away and be replaced with pain.
As he looked at you, he could tell you were worried and in that instant, he just wanted to reassure you.
He stopped stroking himself and approached closer to you and kissed you again before parting.
“I’ll go in slow…I promise…I don’t want to hurt you…So if I do just tell me…Remember i’m here for your pleasure not mine…”
You wrapped your arms around your neck and kissing him back nodded.
He stayed close to you feeling your body pressed against his and grabbing himself slowly aligned to your opening.
He entered slowly just as he promised and you felt yourself stretching like never before.
There was a pain and you seemed to forget the pleasure from before. You could only close your eyes shut tight and hope to keep in your voice.
He noticed your expression changing and stopped pushing himself in.
Out of breath, he swallowed hard and kept his composure to keep himself from just shoving his cock inside.
“A-are you okay? I’m hurting you aren’t I? I’ll pull out if you want me to…”
Although it hurt, you knew it was only like this for the first time and later it would dissolve into pleasure.
You wanted to be with him and just couldn’t deny you were glad to losing it to him rather than anyone else. So you shook your head, and kissing his cheek whispered, “It’s fine…You’re doing just as you promised…It hurts but only for a moment…Keep going…”
He felt bad and kissed you back and was about to back away until you held him tightly to you.
You then felt him a little deeper and yourself stretching even more. You let out a faint shriek and he kept apologizing as he pushed inside of you.
He wrapped his arms around you tightly and stopped for a while, resting his head in the crook of your neck and letting you breath and adjust to him.
The pain did bother you but as you noticed him stopping for a while, you couldn’t help but feel grateful for him being understanding.
As he heard his name coming from you, he raised to look at you and saw the eagerness in your eyes.
You took in a few deep breaths and finally told him.
“I-I’m ready…I think i’ll be okay…”
He nodded and couldn’t help but smirk.
He started to thrust in an in and out motion and went as slow as he could.
You felt the pain again but this time it was mixed with some pleasure as well. You grew to be accustomed to it and to enjoy it.
It made you moan and whimper and he understood that you started to enjoy it.
He was ready to show you what he was about but still maintained his calmness.
He got up and started to go a little faster than before. He was cursing and started to talk to you in the dirtiest way you ever heard and you couldn’t help but be in the heat of the moment along with him.
You were able to enjoy the feeling of his cock pushing in and out and him holding you tightly. You felt each of his thrusts getting faster and you in that instant, you couldn’t keep your voice down.
It made him chuckle and before you knew it he felt you tightening around him and he needed to release. He pulled out and came all over your stomach. You were both out of breath and he couldn’t help but smiling and laughing.
You noticed the blood on him and felt embarrassed about it but as he noticed you, he smirked and said “Y/N, congrats…you’re not a virgin anymore…”
He went to kiss your forehead and wrapped his arms around you tightly and slowly drifted to sleep as you hugged him back.