First time

[sky]

Hey!! So I met a guy and it’s been awhile and I like him a lot, this isn’t a mania thing please believe that, this isn’t happening like right now do to there being a pandemic. Anyways, the first time theres vaginal insertion will it hurt? He said he’s big and does that actually matter? Another question I had is, is there a big risk in going in without a condom for a bit and then putting one on and finishing in one?

[Sam W]

Hi Sky,

While vaginal sex can hurt the first (or fifth, or forty-fifth) time, there are lots of ways to make sure it's comfortable and pleasurable, even if a partner is on the larger end. This article gives a really good run down of those: From OW! to WOW! Demystifying Painful Intercourse.

And yes, only using a condom for part of the time increases the risk of pregnancy and STIs significantly. So, if you and this person end up having sex, you'll want to use a condom for all of it.

[sky]

They don’t have anything though so it’s okay right?

[Sam W]

Well, unless you're on a secondary method of birth control, it doesn't remove the pregnancy risk from the situation. Too, you'll want to confirm with this person how they know they're STI-negative. Did they get tested? For what STIs? How recently? And even with that information, we advise people to use barriers for the first six months of a sexual relationship. If, after those six months, everyone intends on staying monogamous and has negative STI results, then going without a barrier is less risky.

[sky]

That’s a lot of work lol. He said he’s good at pulling out but I don’t know if I want to do that but he’s the one who said going a bit without and then putting one on, I said condom but then he mentioned that and I said ok

[Heather]

You have to know that anyone telling you they are "good at pulling out" from the start like this, a) is telling you they don't practice safer sex, and are therefore also telling you they're a big STI risk for you, and b) is also showing you from the start they are not willing to do the most basic kinds of things sexual partners who care about each other do to protect one another's health and c) when they do so in response to you asking about condoms, is showing you they do not want to respect your boundaries. A guy talking to anyone like this is showing you his true colors and that they are not good.

This is the kinda fish one throws back, in a word.

[sky]

Well he said something along the lines and then I asked and I said I wanted to use one but I don’t know. I really really like him and so I probably won’t use one and if anything I’ll take a plan b

[sky]

I just don’t understand how you are all saying sti, if the person is just with me there is none right? I’m very confused on this stuff and then I know that if I have a cut or something I can’t get one but it’s so confusing I have no idea. I don’t even know what cum feels like so he could in me and I wouldn’t know

[Mo]

I think if you're feeling this confused about it, that's a pretty clear indication that it's time to slow way down and make sure you're feeling well-informed and more sure of the situation before proceeding.
It's clear that this person has had previous sexual partners, because he's talking up being "good at pulling out," so he would have been at risk for STI transmission through previous partners. Testing is absolutely necessary for him to know if he has STIs or not; if he says he doesn't, then you'd want to ask the questions Sam posed above: Did he get tested? How long ago was that test? What STIs was he tested for? Plus, has he been having unprotected sex since that test? If he isn't willing to answer those questions, that's a clear sign that he's not respecting you or your saety.
You mention not wanting to use a condom because you really like this guy, but turn it around: if someone likes and wants the best for you, then I would hope they would want to only have sex in a way that offers you the most safety and protection. Going without a condom and claiming he can pull out is, as Heather said above, a huge sign that he's not taking your needs or safety into account.

[sky]

I just really like him and I’m trying so hard to be good enough for him. It’s been like 3 days and he hasn’t abused me and I just can’t believe it. He’s so nice to me and I don’t know if it’ll last but i actually believe there’s nice people out here now and I’m just sad and struggling to be okay with myself

[Sam W]

While I'm glad he's being nice thus far, it may help to remember that not abusing a partner is literally a baseline requirement for being a decent partner (although, if you've only known him three days, it's hard to get a full read on someone's personality in that time). And, unfortunately, even if he isn't abusive, as Heather and Mo have both said he's showing a big red flag in terms of not taking your needs or safety seriously.

I don't say any of that to make you feel bad or ashamed, just to offer a bit of a reality check, because it sounds like he's trying to put you into a position where your health would be at risk and is pretty clearly demonstrating whose needs he sees as worth considering, and they aren't yours. So, as Mo said, I think it's sound to slow things way, way down with this guy.

[sky]

Why do you all have to make me overthink and be sad. I thought it was going well and yes we are going slow, I am horny and wanna have sex eventually. He’s nice to me and it sucks that you all claim he doesn’t care about me >:(

[sky]

Okay well we’re planning on it, I’ll make sure we use a condom for it all :/

[Heather]

Hey there, Sky.

We're not responsible for your feelings or thoughts, but our intent in posting what we did certainly was not about trying to cultivate sadness or anxiety for you. Rather, our intent was to let you know what we know about the kind of situation and responses you were posting, and to do our best to give you information that can help you keep yourself safe and best avoid any kind of harm.

People can be nice to us and yet still not have our best interests at heart, or still put us in unsafe situations. Right now, during the pandemic, a new sexual partner or any kind of intimate physical contact with someone new is itself highly risky for a health standpoint, so again, we'd strongly advise you reconsider (and recognize that it's also a red flag right now for people to be moving this fast in the midst of a global pandemic). But in the event you don't, by all means, I hope that the least you can both do is use the basic protections we have for new partners with STIs and other health risks.

I am a bit concerned that this post feels a lot like where we started when you were posting way back when. As I've talked about in the past in a similar scenario, I feel uncomfortable with having to make big pushes to try and keep you from taking big risks. You've come and asked us for safety advice, and we've given it to you. I understand that you don't like what we've said, but I don't feel good about arguing with you about it -- after all, your choices are yours to make.

I just don’t understand how you are all saying sti, if the person is just with me there is none right? I’m very confused on this stuff and then I know that if I have a cut or something I can’t get one but it’s so confusing I have no idea. I don’t even know what cum feels like so he could in me and I wouldn’t know

It did sound up there like you were saying you didn't know about safer sex basics and how it all works, so I'm going to leave you a couple links to educate yourself more and then leave you to making what choices for yourself you're going to. Because we care about you, I of course hope that you can make them with your well-being and health your top priority. <3

• All the Barriers! All the Time!
• Can I Get Pregnant, or Get or Pass On an STI From That?
• Safe, Sound & Sexy: A Safer Sex How-To
• Casual...Cool? Making Choices About Casual Sex

[sky]

I don’t think I am in a place where I’m able to date someone or have sex with someone. I don’t know how to explain what I’m thinking

[sky]

I told him I’m not ready for anything like that. He understands. I decided I’m taking a break from dating sites and I’m gonna just go to therapy. No one will love me if I don’t love myself

[sky]

Yesterday I was sad and thought he was losing interest in me so I sent nudes (waist up). I asked for pictures of him and he sent them. I liked them. I’m just so stupid

[Sam W]

Hi Sky,

Can I ask what caused you to switch from feeling like you didn't want to continue pursuing dating to continuing to sext him?

Too, if you want to focus on yourself and therapy rather than dating, it may help to do some things that make those goals and boundaries easier to hold. That can be things like deleting dating apps from your phone, or deleting/blocking people's numbers.

[sky]

I sexted him when we were still on to have sex, I haven’t since I decided to step away

[Mo]

Got it! What do you think about Sam's suggestion to take steps to disconnect from dating sites/apps or delete or block numbers of people you want to step away from?

[sky]

Dating apps are gone But he’s not. I can’t let him go

[Heather]

Is this something you’d like us to help you with? If so, what kind of help do you have in mind?

[sky]

I think I’m okay. I have an intake appointment for therapy today

[sky]

I’m lesbian. This isn’t gonna work with him.

[Sam W]

If you're feeling like this isn't in line with your orientation and your actual desires, then that's a sign to call things off. How did discussing this with your therapist go?