Taking Your Virginity - Headcanon
Okay, so I got two requests for the same thing literally seconds apart from one another. And since you guys seemed to like my Headcanon of having sex on your period, which you can read here if you haven't already, this is another requested headcanon - the boys taking your virginity. Also got kind of carried away with this but who's gonna complain? Sorry if they all seem similar, but these are my opinions and how I see something like this going down.
Note: If this seems similar to other headcanons, I apologize. I'm not trying to steal anyone else's work. Also, this is my opinion blah blah, and not a reflection of their real experiences. Also, I was too lazy to write in condoms, but please do use protection in real life. Also worthy of noting - I posted two stories within four days of each other, something I don't think I have ever done XD
Warnings: boys being soft, sex for the first time, sort of descriptive smut
Anon 1: Are you taking requests if so can you do a headcanon about the boys having sex with a virgin for her first time
Anon 2: Can you do a headcanon about each of the boys taking your virginity?
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✫ So we can all agree that Chris knows his way around the block. You, however, were the total opposite. So when you had met him at a party, you were shocked when you both hit it off.
✫ The thought of sex never really appealed to you. You didn't want to wait until marriage but it also wasn't at the forefront of your mind. That changed when you met Chris. He was funny, his laugh was contagious, and you somehow knew that if you were going to lose your virginity to someone, it would be him.
✫ After months and months of talking to one another, you guys became official, out of the public eye, of course.
✫ I see you losing your virginity with him after a night out. Like you would tell him that you were ready and then the next day, he would be a total gentleman - taking you out to your favorite places, eating dinner, then coming home and just making sure that you were comfortable with him. Or just after a day out in general.
✫ You guys relax against the bed and you know that you're ready. So you let him know.
✫ "Hey Chris," you mumble against his skin. He replies with a hm. "I'm ready." It doesn't long for your words to sink in and he turns and faces you.
✫ "Are you sure?" He says as he cups your chin. You nod and he grins, leaning in to kiss your lips. He takes things slow, letting the fire build slowly between you two. He gently lays you on your back and lets his hips grind into you. The makeout session is comfortable since it's the farthest you've ever been with him.
✫ "Chris, I want more." He nods and lets his hands wander under your shirt and your underwear. Soon, your hands also wonder and before you know it, both of you are naked in front of each other. Your heart jumps at the size of him and he notices how you tense slightly. He assures you that he'll make it as comfortable as possible for you.
✫ You trust him and he begins to prep you, sliding a long finger through your folds and pushing in when there's enough wetness to help ease his pass. When he's stretched you out enough, he lines himself up and asks again if you're sure. You nod and as he pushes in, he makes you focus on him.
✫ You stare into his doe-like eyes seriously, I have never seen someone with eyes like that. Going from innocent to "I can fuck you till you can't handle it anymore" in .2 seconds like wtf Christopher
✫ Anyways. You get lost in his eyes and he bottoms out, hips flush against yours. You feel pressure down below and you're obviously not used to it, so he continues to distract you, placing little kisses against your skin and whispering things like, "You're doing so well amor," and "You're going to feel so good". Maybe tries to make you laugh since he's always so damn happy.
✫ You've never felt so full, in this sense. Well, it's your first time, duh. When you finally grow accustomed to his size and feel, you tell him to move. He pulls away, not all the way out, and pushes back in. Soon, he feels you relax and begins to pull almost all the way out.
✫ He was right - he was making you feel really good. Since it's your first time, he takes his time, makes sure that you're enjoying yourself. When you cum, it's amazing and with Chris mouthing marks onto your neck and whispering things in your ear in between, it just amplifies the sensations he's giving you.
✫ He helps you clean up and relax, cuddling with you afterward and getting all lovey-dovey with you, asking you if you're okay and how he did for your first time.
✬ Same as Chris as far as making the night as comfortable for you as possible. I see them all trying to make it comfortable for you. Maybe he would stay in a cuddle, watch movies, really show a softer side to you.
✬ I say that you and Richard will have been together for a while before you open up to him and admit that you're a virgin, or maybe you'd tell him off the bat(depending on what type of person you are). Maybe you'd be a little self-conscious because Richard is experienced and you aren't? I seem him being a little surprised and excited that he'd get to be your first time.
✬ You'd be getting comfortable with him when his dick brushes your leg and you're a little shocked. I see him letting you explore his body at your own pace, let you get used to him in such an intimate position at your own pace. Though he takes control in some places.
✬ When he's prepping you, he's whispering sweet things and helping you take your mind off of what's to come. When he's done prepping you and begins to push in, stopping to let you adjust every few inches, and tries to take your mind off of what's happening by leaving little kisses. Once he's fully inside you, he lets you take all the time you need to adjust.
✬ "Okay Richard, you can move," your voice falters. He nods and starts slow, and even at this slow, gentle pace, he still hits places deep inside you. Same as Chris, in the sense that you're filled up.
✬ "Does that feel good, baby?" He grunts against your neck. You can't reply verbally but you manage a nod and he smirks, his ego would boost to the fact that you're speechless because of him. As you both get closer, he picks up his pace slightly and your seeing stars, putting passion into his thrusts.
✬ He also helps clean you up and makes sure you're okay. You just nod, feeling drained of energy and basking in the afterglow. He pulls you into his chest and you both relax and eventually fall asleep.
✬ And when you've fucked a few more times, he'll start bringing out a more dominant side, just to see what your limit is and what you can and can't handle.
✵ That hair tho. 🥴👌 Blonde-haired Zabdiel is supreme
✵ Like Richard, maybe he would let you explore at your own pace? I also see you and him having a relaxing day and you feel comfortable enough with him that you want to do it with him. You and him have been together for quite some time now.
✵ I say it would start with you two cuddling on the couch or bed and maybe you guys are in the feels and a makeout session ensues. You never went passed make outs and the occasional roam of his hands, and he never pushed you to do anything.
✵ This time was different. You wanted to go all the way with him. You grind on him and he'd let you explore him, making your way down his body to his hard cock, confined within his sweats.
✵ You mess with him a little before pulling down his sweats. I see him letting you stroke him a few times before he makes it all about, bringing you back up and putting you beneath him. I see him taking his time going down you, finding sweet spots on your neck, giving your chest attention before finally reaching where you need him most.
✵ Running his fingers through your folds, slicking you out, even more, he presses a digit in and begins to slowly move it in and out. When you get used to one finger, he'll add a second, scissoring you out to help open you before grabbing more lube, just to be safe.
✵ Taking his time entering you, he presses in slowly. You tighten around him and he would do things to help relax you, peck your lips, rub his large hands against your sides, etc. When he does finally bottom out, he continues to comfort you, letting you take your time adjusting.
✵ When you tell him it's okay to move, he creates sensation you didn't know could exist. I see him also whispering sweet things in your ear. He has you moaning in no time, even at a slow pace. "Feel good, amol?" He grunts and you nod, moaning his name.
✵ He brings you over the edge with a few more thrusts. Maybe he would pull out and cum on your chest instead of cumming inside you, to not go too far with you for your first time. Once you get more comfortable, you'll start finding out what he likes and stuff. Definitely would take a nap with you right after.
✺ I don't think he's a virgin... Though I half want him to be if he isn't but if he hangs around Chris... His beard throws me for a loop. For the sake of this, we're gonna say that he is a virgin as well and he's saving himself for the right person
✺ You two would have defiantly talked about it in advance, planned a day to do your favorite things to help calm both your nerves. Also, you two would have been together for a while before this topic came up. When the time comes and you both feel you're ready, you take things to the bedroom.
✺ Would be awkward, since you both have never done this before. I can see this as a "find out what we like before we actually get down to it" kind of thing, but Joel makes sure to make it about you. I see him making you cum on his fingers first, and you stroke him before you finally can't take it and you want him inside you.
✺ He also uses extra lube, just to be safe, and he makes it very clear to you that if you need him to stop, tell him to stop. Also asking if what he's doing feels good. If it's his first time, he might have trouble holding back his orgasm from the feeling of your walls against him. And that's fine, you don't hold it against him, and reassure him that it's okay.
✺ When he bottoms out and you've adjusted, and he begins to thrust, you both would get lost in the feeling. Maybe you both hear a weird noise and laugh about it, cause let me tell you, sex in real life is very different from sex in fanfics and isn't always so picture-perfect.
✺ You both probably wouldn't last long, so you try to make the most out of what time you have. He helps clean up the mess and you guys would practice some more, but maybe not as much as say, Chris or Richard, seeing as you would have other things to do than just fuck.
❂ Though he's young, he's not a virgin. He doesn't have as much experience as Chris or Richard or Zabdiel, but its experience nonetheless. You on the other hand... Not so much. Sure, you've dated in the past, but none of them felt right.
❂ That changed when you met Erick. He made you comfortable and never pushed you to do anything you didn't feel comfortable with. And that's why you wanted him to be your first time.
❂ When you tell him that you're ready and want to take your relationship to the level, he is excited to be your first. I say you and him plan a night in, just relaxing, watching movies, him playing guitar for you...
❂ You feel that tonight is the night and you're ready. He will ask if you're sure about this and when you say yes, he leads you to the bedroom. He takes his time with you, giving your body all the attention - to your chest, to your neck, whispering little things in your ear...
❂ When he reaches your entrance, he plays with you a little, just to see if you like anything he does. When you're slicked enough, he pushes a finger in and continues to move, adding a second one to the mix.
❂ When he feels you're stretched out enough, he pulls down his boxers and asks one more time if you're ready. You tell him yes and takes his time pushing in, pulling back and thrusting in if he meets resistance. Once he's bottomed out, you moan his name.
❂ I see him making it a fun deal, kind of like Chris, which helps ease your nerves. You tell him he can move and he has you moaning. His body is flush against yours and you can hear his grunts. If you get tired of the slow pace, you ask him to speed up a little, and he does, dragging out his thrusts.
❂ He helps clean you up and asks if you're okay and how it was for your first time. Maybe you take a nap afterward.
Tgalist: @cracraforfandoms @kmsmedine @kikixfandoms @xmaudjexo @richardscurls
