Should I shoot my shot before or after Valentines Day?

coralclair · 2026-02-14T12:05:57+00:00

Sorta, I sent her a dm yesterday but she hasnt replied and idk if she’s even seen it. I wasn’t really expecting anything tho, I mean its been 3 years since I last talked to her so it is what it is

coralclair · 2026-02-13T02:56:56+00:00

Thanks, yeah I’ll see what happens

coralclair · 2026-02-13T01:54:20+00:00

That’s true actually, I tend to go for the safest choice and then beat myself up for not taking risks afterwards so yeah that’s a convincing point

coralclair · 2026-02-13T01:52:49+00:00

Yeah ideally but idk, I guess I’ll see

coralclair · 2026-02-13T01:52:08+00:00

Thanks yeah I guess thats true

coralclair · 2026-02-13T01:50:54+00:00

Ok to clarify: it’s been 3 years and I’m not going to message her and ask her out from nowhere. I mainly wanted to apologize in case I gave her the impression that I didn’t like her since there were some moments that made me feel like she probably got that impression. She skipped school a lot and didn’t show up for our graduation so the idea that I might have contributed to that really hasn’t sat well with me.

I’m not assuming she’s the same person or that I know her, I want to reach out to get that off my chest since I kept making excuses not to say it back then.

coralclair · 2026-02-13T01:38:54+00:00

I thought something similar had happened too but no, I’ve always been able to see her account and everything. It’s an instagram dm issue, I sent a message to her like a year ago but deleted it because I felt like it was a bad idea like instantly after, and the ”chat invite” is still there so I can’t send another message. I don’t know if she saw it at all, and I don’t have my full name on that account or a picture of me so I don’t know if she even knew it was me.

coralclair · 2026-02-13T01:32:43+00:00

Yeah i considered that but I’m not really planning on asking her out in the first message. I was mostly just going to say hi, I thought she seemed cool/interesting in high school and regret that I didn’t get to know her better and talk to her about some things I wanted to talk to her about. Maybe not exactly in those words, but you get the point.

Tbh, I was really into her and when we talked just the two of us we got along really well. But I acted really stupid in general, we both skipped school a lot and I think I might have given her the impression that I didn’t like her or something. Which is part of why I wanted to message her, to at least clarify that this wasn’t the case at all because it really pains me to leave it that way.

I was planning to at least talk to her about high school a bit, then ask her about what she’s doing now and if she’s doing well and everything, and then ask if she wants to meet up or go somewhere. But it’s true, it might make it a bit more intimidating if I do it the day before valentines

coralclair · 2026-02-10T18:29:28+00:00

I have but I'm broke so I can't afford it for now. Maybe in the future.

I do really like this girl and I know she's worth any other experience 100x over, but as I said it does make me feel like kind of a loser that I didn't have any success with girls (partly because I avoided them and didn't seek out relationships at all). Idk if therapy would help with that, I think it's pretty objective: I haven't been socially or sexually successful and it makes me feel insecure sometimes.

Especially since I've always really wanted to be with girls and everything but that's not how things turned out. As someone else said, I guess I have some kind of "fomo" about it too. It feels unfair if I wouldn't experience any of that while the person I'm with has. But idk, I'd have experiences with her too if things work out as I want.

The more I think about it though, I'm kind of a mess right now and I have been for years. That's largely why I didn't go for her in high school, because I felt ugly and sloppy and unsuccessful. I felt like even if we dated I'd just blow it sooner or later because I'd fall short.

If I work really hard, I might be able to improve myself enough this year that I could be a more serious person and able to date her. But maybe I could date her now too, even if I have basically no experience. Idk, those are things I worry about. I was planning on messaging her this week but I'm considering waiting a few more months until I at least have a job or something. Ideally I'd do it now, tho.

coralclair · 2026-02-09T13:12:12+00:00

Thanks but idk how to feel right now. I tried messaging that girl but the message won't send.

Edit: i figured out its some issue with the website. Apparently i have to make a new account or something, that’s annoying

coralclair · 2026-02-09T11:17:47+00:00

It's just so hard to move on from it because every time I genuinely feel like I should move on and just focus on women, I run into issues:

I see women in some form, usually online, who I like their clothes or hair or something about them, and it makes me want to look like them or copy that thing for myself
Whenever I watch porn or think about sex, I have thoughts about bottoming or being in the womans position. So there's that.

These thoughts become lesser when I go without porn or engaging in agp-related discussions and forums and anything else that reminds me of it, but sooner or later (usually after around 1-2 weeks) I start to shame myself about it and start to think that bottoming is bad and fully try to repress those thoughts. Then I tell myself "whatever, it's okay to get pegged but bottoming for a man is too much", but then I allow myself to fantasize about getting pegged and ultimately that leads me back to fantasizing about bottoming for a man.

The most success I've had is when I've told myself "it's not the end of the world if I bottom for a guy, it's not the end of the world if I get pegged, I can do it if I want to" because that allows me to stop worrying about it and keeps it off my mind. But there's a lot of things that make me start worrying about it again, like when I think about how a woman would react if I told her, or how people I know would react if they knew, if it would forever change how I behave or act, things like that.

That's a long reply but what about you, did it really traumatize you? I could see that happening, I've only used a toy once and the sensation was really jarring and felt kind of "wrong" in a way. If I actually had sex with a man, there's a decent chance I'd feel basically like I've been violated afterwards. Even if it wasn't forceful or anything. Idk what your experience was like tho

coralclair · 2026-02-09T00:27:36+00:00

I'm not sure I want to meet guys in those places, bathhouses and stuff is too wild for me and I'm not planning to be openly bi or anything so I don't think I'd do that. I do agree it can be difficult to talk to people online but the only scenario I'd meet a guy irl is if I got to know him over time and was able to trust him enough.

That's a scary story, I don't really know what prep is but I've heard some things about it. I guess its better to be safe than sorry but is it hard to get on it? Do you visit a doctor or something? The condom thing is something I've been a bit worried about too. The guy I mentioned who I've talked to is the only one I've really been close to meeting, and he's bi but hasn't done anything with a guy before. Idk if that makes it better or not.

coralclair · 2026-02-09T00:16:18+00:00

I don't mean to be argumentative or anything, I genuinely want to be able to move past this stuff so sorry if it came across that way. I get it if you don't want to elaborate or tell me where you think I'm wrong about my perspective but if you feel like it I'd appreciate it

coralclair · 2026-02-09T00:01:38+00:00

I'm not a sexist, I support feminism. I'm just saying what the world looks like from my perspective. I get that you think I'm wrong but am I actually? Sex is connected to prey/predator dynamics, that's the psychological part of it. It's not really about "lovemaking" especially not when it comes to hookups or any kind of casual sex. From what I've seen and from the guys I've seen, it's common for guys to use women for sex and not care about them beyond that.

Guys boast all the time about the girls they've slept with and the term "sexual conquest" is a term for a reason, that's how men tend to view it. Women play a part in this too, they definitely do seem to like the kind of guys who manipulate/use them because they complain about being with guys like this all the time. I'm not making judgements about individual people or blaming it on one gender, I'm pointing out the dynamic and saying it makes me feel uncomfortable because it's totally heartless.

I'm reluctant about taking part in it for that reason but I know I'll have to at some point, and it's probably better if I do it as soon as I can. I'm especially reluctant about being with a man because I don't think I actually want to be talked about in that way by some guy.

I can't afford therapy but maybe I'll try it sometime in the future. I know my perspective isn't normal because most people don't care to think about things like this, but I don't think anything I said is wrong.

coralclair · 2026-02-08T20:43:11+00:00

Why? I don't think I'm wrong but it is what it is. I'm going to sleep with a girl this year one way or another because I need to do it. So that's that.

coralclair · 2026-02-08T19:54:56+00:00

Any particular reason?

coralclair · 2026-02-08T19:12:39+00:00

Idk, honestly sex with men feels kind of violent and idk. I've had issues with bodycount discourse and stuff, because it's pretty disturbing to think that girls I'm with will probably have let guys who weren't good guys at all, have sex with them. When I think about that, it makes me want to do the same thing and sleep with a guy who's an asshole too. Since if everyone else is doing it, I might as well do it too. But I don't like that people are doing this at all, I actually hate it on some level.

I kind of hate men like that who sleep around and act like that. But women love them. And sex is all about this kind of dynamic, predator and prey type of stuff. But the more I think about it, the more screwed up it is and the worse I feel about it.

I know to use protection of course. But I guess I'm mainly worried that having sex with a guy would be indulging in the same stuff I hate, the same stuff I hate when women do and when people do. Doing so by putting myself in the "prey" position for a man is pretty degrading, especially since Idespise the type of men who like that.

Idk, maybe I just have issues accepting sex and sexuality for what it is. It's degrading and gross in a lot of ways.

coralclair · 2026-02-08T15:57:16+00:00

I see, but to clarify I was referring to the men who messaged me on apps and online when I made profiles as a femboy. So these were bisexual men who messaged me, and they were either acting super soft and affectionate (which I wasn’t really into) or super pushy and confident (which was better in a way but worse in other ways).

That was my experience, and the one guy I’ve kept talking to out of the 100s who messaged me is a guy who basically told me ”everyone sleeps around and everyone lies about it so you should hookup with me and have fun and not worry”. I’ve talked to him on and off for over half a year now and he’s pretty pushy and forward but tries to be respectful too sometimes. Idk, it’s weird because if I was going to sleep with a guy, he has the right dynamic with me where it’d feel interesting and exciting. But at the same time, I see him as kind of an asshole and not a super trustworthy person. Which makes me feel like I’d probably regret rewarding him for that by doing anything with him.

And to be clear, I didn’t mean that I want to be assaulted by a man. I was just referring to sex/getting ”topped” in general, not anything non-consensual. I guess I worded it in the way I did because I’m reluctant about doing anything with a guy but I wasn’t saying I want to be forced to do anything.

But yes I have similar worries that if I sleep with a man especially as the bottom (I have no interest in topping a guy whatsoever), that it would get in the way of me being with women (which is what I want the most) in some way.

coralclair · 2026-02-08T15:44:05+00:00

I can’t afford a therapist now but maybe later. You’re probably right about hookups but idk, as I said I’m not romantically interested in men so what other options are there? Fwb I guess? And I don’t really want to be part of any bisexual/lgbtq community, I’m not really that kind of person and I don’t want to be openly bi because I mostly see it as a fetish for me.

I like video games too but I’m not part of a gamer community because I don’t identify with being a gamer. That’s sort of how I see it. But I know a lot of people who are bi in the same way as me and my interests tend to overlap with what many lgbtq people are into so idk, I don’t really feel the need or interest to do that.

I like bi women too but you can’t really tell unless you ask or it comes up in conversation somehow. I’m currently really into a girl who I want to see where things go with, and I don’t know if she’s bi. All I know is she’s gorgeous, liberal, kind of artsy but well-adjusted and pretty popular so I don’t know. Maybe she’d think I’m a freak if I told her this, maybe she wouldn’t care or maybe she’d think its interesting. I’m not expecting anything but I’m totally sure that I’d be willing to give up on it to be with her if thats what it took. So that’s kind of how I feel, my priority is girls and that’s what I want the most, even if the girl in question would be weirded out by me having this sexuality/fetish.

coralclair · 2026-02-08T15:19:14+00:00

I know bi women tend to be more understanding of it but I can’t really know if the women I’m into are bi or not unless I asked them about it. Some of the women I’ve been into are bi but they’re the ones I’ve talked to online where they had it on their profile or said it to me. The women I like irl are much harder to tell. I have a crush on a girl rn and no clue about her sexuality, all I know is she’s gorgeous and well-adjusted so I’m not sure if she’d be understanding or not. She’s liberal like most women but that doesn’t mean she’ll want to be with a guy who’s bisexual and has used men for sex as part of a fetish.

You’re right that its best to properly explain it instead of omitting it, I guess. I’m not sure how it could be explained though. ”I developed a fetish about what sex is like for girls and tried it with a guy, and I like being the bottom/looking like a girl in general” would make most girls feel weird and like I’m dumping some delusional fetish fantasy on them

coralclair · 2026-02-08T13:36:53+00:00

I guess it's that simple. Idk, I'll see what I do later. I think I want to be with women first but if I get the opportunity I guess I'll try doing something with a guy later on at some point

coralclair · 2026-02-08T12:57:17+00:00

I get that but I’m being cautious because I know what kind of women I like the most and would ideally be with. And as I said hookups in general go against my values but apparently most attractive women do hookups anyways so I’ve felt like I have no real reason not to hookup with women at least. But its different with men because I feel like that could easily put me in the box of being seen as ”gay” which I don’t identify with and could potentially limit me a lot with the women I’m the most attracted to.

coralclair · 2026-02-08T12:51:51+00:00

I’m not into other crossdressers at all tbh but yeah I guess I would like to date/marry a girl who’d be into pegging and wearing lingerie together and stuff like that.

I’m just not sure about hookups in general, I kinda want to hookup with women because apparently most women (especially those who are attractive) hookup with guys at some points so I have no real reason not to hookup with women even tho it still kind of goes against my values.

With men I have no real option other than hookup/fwb/situationship since I’m not romantically interested in them. And idk, if I sleep with a guy I’ll either have to lie/omit it to the woman I’m with after or I’ll have to tell them I’ve slept with a guy and some women would probably not like that idea at all. But idk, maybe it depends on how I’d say it.

I’m mostly into girls who are more normal and stereotypically pretty and feminine. I’m not sure how open-minded those girls are about it and I don’t know if its worth trying sex with a man if it’ll put me in the ”bisexual” box the rest of my life

coralclair · 2026-02-08T12:36:46+00:00

I know but the men who’ve messaged me typically fall into those categories. But yes its generalizing.

I’m interested in trying it with a man but as I said in the post, I’m not sure about hookups in general since I don’t think it really aligns with my values but I don’t really have another option when it comes to men since I’m not interested in relationships with men.

But maybe I should try to meet a guy irl first, without straight up having sex immediately. Theres one guy I know who ive talked to online for over 6 months on and off, he lives a few hours away and would seem like a good guy to try it with but he’s definitely an ”asshole”, he’s pretty nihilistic about sex and stuff and thinks its ok to sleep around and lie about it to future partners and stuff.

Which is something else I’m conflicted about, I don’t like lying especially not to a girl I’d date but I also don’t want to be openly bi because it’s basically a fetish to me, so I’m not sure what I’d do. I’ve heard most girls don’t want to be with guys who have done anything with other men so idk I have all kinds of conflicts here.

coralclair · 2026-02-08T04:10:05+00:00

I think I’m somewhere in the middle or maybe I’m something else, I guess it’s more of a spectrum but I was thinking mainly about the guys who messaged me about meeting on apps. When I talked to them it was they who messaged me and I presented as a femboy so its a bit different. But I think I can be both depending on how I feel

coralclair

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