I'm woefully unprepared for sex and it hurts

[warring]

I'm 18. Let me clear see things out of the way and I hope I don't sound like a bitch for saying them.

I'm not unattractive. I have a good bodyweight, I exercise pretty regularly, and I should have no body-confidence issues due to where I stand. I like to look at myself in the mirror. I have great hair, and I use natural or semi-natural products on it and usually let it down; it's wavy, and it naturally goes almost to my waist. I'm really proud of it. I also have great shoulderbones, like really good definition along my clavicle. I have a good chest, and I like that I have smaller-to-regular sized breasts, as opposed to really large ones. I have a fit physique, more than anything else.

But I have zero confidence when it comes to attracting other people, responding to gestures of attraction, and exploring my sexuality. It's all because I've never done it before, and I can't change that now. But I've put myself into a situation where literally everyone else around me is experienced with sex, but I'm not. I dont know what to do. I would give anything to change it, but I always do something stupid, or I'm unprepared when an opportunity presents itself that I didn't recognize at first glance...I literally don't know how to respond to guys flirting with me, or propositioning me, and so when it does happen, I'm literally left screaming at myself because I recognized too late or walked away. I'm so incompetent at this. All that time everybody spent in highschool drinking and fucking? I spent it reading dusty old books because I wanted my brain to be better than everybody else's. But I'm not better than everybody else--I'm way worse off. Everybody got the awkwardness out of the way. I lived in a religiously conservative household, like one of the ones they show on reality TV. I actually DID have nine brothers and sisters. I actually DID have a curfew of eight o clock. And I was never allowed to sleep over, or have friends over, though my brothers were. I was the oldest kid, too, so nobody told me anything. Nobody showed me how to 'do' highschool. I had to learn and I did a shitty job of it. I have so many regrets and I don't know what to do about changing myself, about getting myself up to speed.

I'm on a time limit, too, I feel like. A coworker is showing a lot of interest in me. He's older, much more experienced, and has a lot of attributes that I've realized I'm attracted to. But he's old enough to drink, I'm not. He's old enough to go to bars, I'm not. He's old enough to meet other girls at those bars, and probably will. I wouldn't be making such a deal out of this if he didn't also show interest in me, but he has--a lot of it. To the end that it's fairly clear, even to me, that he wants me. I want him, too. But I actually so dumb sometimes that I'm sure he must think I'm either uninterested or intentionally playing hard-to-get. I'm not! I just don't know how to flirt back the way that he does, even though I'm trying...but even I can tell it isn't as smooth, and sometimes I feel like I just sound dumb. I have no guidebook, no authority to help me out here. My friends all went off to colleges in different states, and I never had that many in school to begin with, just a bunch of people surrounding me who were generally friendly to me. No real friends. Meaning I never got invited to parties so I never got any kind of experience with drinking or other things. I dont know how to start the conversations that lead to the drinking, or the parties, or the sex. I don't know how to steer them that way, or lead them.

I know why I'm attracted to this guy. I know it's a fierce need, and I want to have sex with him but I also am aware he operates by different rules than passing love notes and {Do you like me?} / {YES} or {NO}. He's so indomitably sarcastic that I'm not actually sure whether he's coming onto me at certain times, or just joking around. I'm confident that few human beings would put forth the magnitude of effort he does to talk to me, to touch me in passing, even, if he didn't want me. I've just built up a network of second-guessed second-guesses in my brain that they're getting impossible to work around and I feel like I'm stunting the relationship we could have, preventing it, even. I shouldn't lack this much confidence in myself, but I just want to lose my "virginity" so that I can get past this wall of weird anxiety, and yet I've let myself focus so heavily on this guy that I feel almost paralyzed. I forget things when I'm around him, I drop things in much greater frequency (usually the conversation, lel) and I look forward to every day he's on shift that I am, and I have to grind through all the ones he's not on with me. He's my only real friend at work, and I have two jobs! He's funny on another level, he's snarky as fuck, and I love to be snarky with him and that's what makes doing this job okay. Because the pay sure isn't enough on its own. But in the last couple of days, given chance meetings outside of work and work meetings all the same, I'm feeling like a tension is building, at least inside of me, but I have no ability to gauge if it's the same way for him, or how to act on that tension to diffuse it completely. I dont care what the sex will be like, because it'll be with him. I'm not scared of the sex itself. I'd trust him. If I'm anxious about the physicality of it, I'm self-conscious about my thighs, and about my vagina, because I'm 1) not sure I'm shaving right, and 2) very self-aware of my legs, even though I know, objectively, that they should be fine, and they look fine in leggings, which I often wear, and they have some of those nice accents and grooves you get from regular cardiovascular workouts. But I'm still aware they're not perfect, and I'm afraid they look like chicken legs and the inside of my knee sticks inward too far because my mother's did and we had a really poor, I mean, awful relationship throughout highschool, most of which made me feel the kind of solitude I do today because I'd go to school tired from studying the night before, stressed from having fought with her on the way to school, angry because she'd make weird and restrictive demands of me that would prevent me from going to my friend's birthday party that wekeend, and terrified I'd end up like her. She never worked out, not for her appearance. She wasn't that kind of person. But even though I do, and my body has some tightness to it, resilience, unlike someone who doesn't work out, I'm still afraid. Somewhere, in my brain, I'm worried she's given me the genetic cheat code to eternally chicken-bowed legs as her last act of malice. I dont know, man.

I dont have any close friends nearby. I do online gaming, and those guys are the closest friends I have. I would probably even trust some of them with my relationship problems, because a friend is a friend and I'll take them where I can get them. But I don't want a friend in this guy. I want sex. I want to dispel this shit because surely I'm no worse or weirder as far as bodies go than literally every other teenager I went to highschool with. I can't be. I want him but I don't know how to respond to him. I dont know how to say 'yes, I want you, too' in flirtspeak, or even to interpret when he's saying that to me. We haven't asked for each other's numbers, but I don't feel like the burden should be entirely on him. This is 2015, guys and girls (/others) should have equal parts in relationships. It's no longer the guy's fault for not initiating, and I'll take full responsibility in my case (my many cases, regarding him). But I know nothing about this.

What I do know is that guys my age don't do it for me. Young guys with no lines don't do it for me. Inexperienced guys don't do it for me. Not timid, or shy, or humble, or nice guys. Unfortunately, I'm attracted to this weird type that's snarky and a little bit pushy and oversteps the boundary just enough to challenge normalcy and make me want to push back. He's not nice, he curses as much as I do, but he's rarely actually unhappy. He does it because he doesn't give a shit about shitty people and he's willing to call others out when it needs to be done and he's not okay with taking the blame when it isn't his to shoulder and he's good at what he does and he knows it just enough to be confident, but not so that he has to brag, to be a jackass about it.

And here I'm doing the same thing I did the last time I fell for a guy, I go writing this character in my brain that acts how he does and looks like him so that I get to accept his flaws for gold instead of treating him like a normal person, like anyone else. I put him up on a pedestal no one deserves to have. And this breaks the objectivity that I learned to approach shit with back in school--it scored me wonderful grades then, but isn't holding up at this stage in my life, tbh...

I feel like I've gone wrong in so many places. I just need to loosen this tension. I'm still not even sure I can please myself sexually, and I've tried. I've tried thinking of him, and of not. It hasn't seemed to work, but I acknowledge I've only just dabbled in it (forgive the pseudo-pun). I'm utterly at a loss for what to do. I'm unable to tell him what I want. I dont know myself. I should be able to express my desire to him, it should be a primal thing, but I'm constantly fucking up the entendres or not being able to return them, I feel like. I'm so confused. My parents never taught me how to deal with this shit, and if they had tried, it wouldn't have helped. Our philosophies are worlds apart, if simply due to the fact that there's no way in hell I'm "saving myself for marriage". I lived my highschool years sexually repressed and I'm done with it. It hurts being this way, so disconnected from everybody else. I need someone now, but I don't know how to tell this to the guy without scaring him off, or being too forward, or looking dumb and childish, which are apparently fears in the dating world.

Help me, please. Or don't.

[Sam W]

Hi Warring, welcome to Scarleteen

A few things that jump out me are the ones where you say like you feel way behind everyone else your age in terms of sexual experience. I know it can really feel that way, especially when you got very little sexual or romantic experience, but believe me when I say that plenty of people your age have not had sex or are not having sex right now. Plenty of them are walking around feeling as awkward about it as your are. So, don't be down on yourself for not having met some deadline for having sex. There is no deadline, no timeline, that happens for everyone. The when and how of people having sex has so much to do with chance and circumstances that timeline simply doesn't work.

The same goes for knowing how to flirt. Flirting is hard for a lot of people, and is a skill that most of us have to learn. I recommend a site called Dr Nerdlove. It's aimed at men, but a lot of his advice about how to flirt and interact with people transcends gender lines.

I also want to caution you against dating your coworker, for a few reasons. One is that dating coworkers can make you work situation difficult, or create weird power dynamics in the work space. The other reason is that older guys pursuing younger girls set off a major red flag for me. Often, they're pursuing someone younger because that person has less experience and can therefore be molded or pressured into being their "perfect" woman. They also tend to assume that younger women will be less willing to call them on their BS (often due to a lack of experience). Whenever I see an older guy going after a younger woman, it makes me wonder what traits he has that make women his own age not want to put up with him (not that this guy at your office is necessarily awful, just that this is a pattern we see).

I want to ask, how do you feel about yourself in general. Like, on any given day, when you look in a mirror, do you like the person who looks back at you (not just physically, but your whole self)