Reaching Railed: Fingering, tight pussy (TP), and how to go from kissing to fucking

so much vagina talk today! my fave kind of talk!

I have never been fingered before and I’m a bit nervous for the possibility of this happening. I have a low libido (lexapro sisters) so I don’t fully know what I like either. Any suggestions?

Lexapro sisters rise up! This is such a valid question and it makes sense to feel nervous going into any new sexual experience. My advice: Don’t be afraid to communicate these anxieties to whoever is fingering you before it takes place. It’s as simple as, “Hey, just so you know, I’ve never been fingered before, so please be gentle.” I’m guessing this will be more enjoyable for you anyways, as light teasing and a gentle touch during fingering tends to be better than when guys go right in for the jackhammer (IMO!). You also may want to apply some lube first if you’re worried about not being wet enough, and this can help make it feel more comfortable! And if he or she is being too rough or it doesn’t feel good, don’t be afraid to ask them to stop! There’s nothing wrong with that!

As for not knowing what you like—I’d highly suggest experimenting with masturbation beforehand to try and become familiar with your body and what you enjoy. You don’t have to finger yourself if that feels uncomfortable, but try to play around and notice what spots are sources of pleasure for you (check out some of my fave sex toys here)! I totally hear you that Lexapro has lowered your libido, but in my personal and unprofessional experience, the more I masturbate, the more consistently horny I am. And of course, remember that there’s nothing wrong with having a lower sex drive, and if you do want to change it, you can contact your doctor about getting meds to help! Zero shame in that!

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I’ve recently started dating someone. We both enjoy oral and finger play, and generally teasing each other. But I know she wants to do more penetrative sex. I do want to try it more but I have avoided it for years due to lack of experience, and to complicate matters I think she also experiences vaginismus. How can I approach this so that we’re both comfortable, that she’s satisfied, and whilst also being clear on what my preferences are (mostly oral)?

So glad you wrote in this question! Vaginismus is something that so many women experience but isn’t often spoken about in convos around sex—so I’m thrilled that we can talk about it now.

It sounds like your dilemma is twofold: First, your partner wants to do penetrative sex, something you have a lack of experience in and aren’t sure it’s your first choice (but also something you’re wanting to try!). And then the second part is your girl’s vaginismus. Let’s start with the latter. For those of you who don’t know, the clinical term for vaginismus is TP: Tight Pussy. JK but also not because I feel like that explains it pretty well. Women can have this in varying degrees of tightness and discomfort, and some go to physical therapy for it and are directed to use increasingly sized dildos to help stretch out the TP. It’s a very real thing and it’s lowkey really sucky!

So, how do you have sex with a woman with TP while making it enjoyable for her? While I don’t personally have it (sometimes I worry I don’t have enough TP if you catch my drift), I have engaged in convos with many women who do, and the insight is this: Take it slow. Lean into the teasing that you know so well to help her get warmed up. Maybe even give her advanced notice that you want to bang so she can do some of her physical therapy exercises beforehand. And of course, don’t be afraid to take this question to her and ask what you can do to make it more satisfying! She knows her body better than anyone.

Okay, now for the other half of your question—introducing penetration. I totally get being nervous and avoiding it, but IMO, penetration is the part of sex that is hardest to fuck up, so I really don’t think you need to worry. Just don’t do a super fast jackhammer, pause for oral sex in between, check in on her needs, and you’ll be golden. No one should have sex if they don’t want to, but it sounds to me like you do want to but keep putting it off out of fear you’re not experienced enough. So I think it’s great that you’re feeling open to trying it! You may decide it’s not for you, or you may love it. Just communicate openly with your partner about what you want—if that’s strictly oral sex, that’s great! If it’s both, that’s great too.

I hope this was helpful, LMK how it goes <3

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Hi, Mia. I’m a senior (girl) in high school, and I’ve never had sex. I know that’s nothing to be ashamed of, and many people are in the same boat, but I’m going to college next semester, and I want to know what to do! Like if a makeout gets steamy, what’s my next step? Do I take off his shirt? Will I have to touch his penis (I’m kinda scared of that)? In short, how do I get from makeout to fuck.

Hi girl! This question is so real. First off, I’d like to say that if you’re scared to touch his penis (valid) then you definitely don’t have to, and it’s very okay to stay in the makeout zone until you’re fully ready to take it farther—even if you’re hooking up with a college boy! There’s really no rush. In fact, there can be a lot of pressure to put out and lose your virginity right when you get to college, but that can also lead to dicey, drunken situations where not all parties feel comfy. So take your time and make sure you’re feeling horny and excited and safe!

Okay sorry, older sister mode is done. I totally get that you want to be prepared if the moment arises! If you’ve never touched a penis before, I would recommend trying oral sex at least once before full-sending it with sex, so you can get more familiar with said penis and make it feel less scary! If a makeout is getting steamy and you want to take it farther, here are some classic moves: Put your hands under his shirt and graze around his chest and abdomen. This may prompt him to take off his shirt himself, or you can give it a go. If you want his pants to come off, I usually play around at the waistband a bit, maybe start to undo his belt if he’s wearing one, and he will probably get the hint. You can also straddle him while making out and start to subtly grind on his penis—just another way to turn up the heat.

For how to start and execute a blowjob, I wrote an entire how-to in this previous Railed post. Hopefully he will reciprocate if that’s something you’re into! The flow of sex is typically foreplay, oral sex, and then penetration (though this can switch around! Ideally, there’s oral sex throughout). To take it from oral to penetration, you just have to say these five words: “Do you have a condom?” He will probably race to his nightstand drawer after hearing that. I have sooo many things I could say about how to navigate your first time, so we def need to make that another post. But I hope this is helpful in understanding how you go from making out to having sex!