Question 1: “How do you get back into the game? (The game being sex). I was cheated on 4 years ago and haven’t had any partners/encounters since. I’m no longer actively avoiding potential partners, but I feel like I’ve lost the hang of things. I don’t feel sexy, and I worry that I’ve forgotten all that I once knew. Help!”

Question 2: “How do you get past your thoughts? I feel my brain is always so hyperactive during sex even when I’m with someone I really love and all I want is to have sex with them. It’s so stressful.”

Question 3: “I’m getting to know a guy, we’ve been going on dates for like 3 months now. The sex is amazing and he makes sure that I’m enjoying it every time and he’s pretty communicative in general. However, it is super difficult for him to cum, he’s only cum once when we’ve had sex. I asked him and he said that it is often like that, so he almost never finishes. Even though we talked about it, it pains me seeing him not fully enjoying it. I know that I’m not the reason, but seeing him stressing about it makes me feel bad. Since we already talked about it and he said that it was ok and told me not to worry, I don’t know what else to do/say, but doing nothing seeing that he’s not totally fine with it makes me uncomfortable. I want him to enjoy it as much as I am. What do you think should be my approach?”

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Question 2: “Can you masturbate too much? I didn’t have an orgasm for my first 28 years of life and now that I’ve figured it out…well…let’s just say I’m making up for lost time.”

Question 3: “I started dating this guy about a month ago and we’re getting closer and closer to having sex. We got naked with each other yesterday and was shocked to see that his dick is really small. I’m talking max like 3-4 inches. My ex (the only person I’ve had sex with so far) was 6.5! I’m not sure what to do with it or if it will even feel good for me. Help!”

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Question 2: “Hi! I turn 27(M) in July and have never been in a ‘proper’ relationship. What I mean by that is I’ve never had a girlfriend, only really some brief flings that last a couple of months before dying out. Admittedly, I feel like a bit of failure, especially because I’m at that stage of people I know living with their partners or getting married. I’ve not been on a date in almost 3 years mainly because I got so fed up with disappointment. Because of that reason I feel like I’ve lost so much confidence. I worry that I don’t know how to date anymore. Using the apps makes me want to spew but so does thinking about meeting someone irl. Sorry if this is a bit long-winded but I would love to hear some tips you could give me or ways I can measure my progress to even dip my toe back into the dating scene.”

Question 3: “Have you been caught having sex? What was the situation and your reaction? How to make it not awkward afterwards (or just live with it...)?”

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“Hey! I am in a relationship and it sucks to say that…the sex is okay. My bf only wants to do either doggy or cowgirl. Also when I try to do oral on him, I get very awkward. I am normally good at it but since being with him, I became abnormally awkward! *side note we are in a long distance relationship so we barely do it until we see each other*”

Hi my love! This is so frustrating, I’m so sorry you’re having this experience. From where I’m sitting, it sounds like you guys aren’t really meshing in the bedroom, which always sucks. I’ve had that experience before in a relationship, where we really cared for each other but were lacking bedroom chemistry. I remember feeling like I was a really bad kisser while we were dating, even though that was something I usually felt like I could do well. That was a telltale sign that our sexual compatibility just wasn’t there. Similar to how you’re feeling about your oral sex skills! It’s not you—it’s just the lack of mesh!

Once you’ve realized that you aren’t loving the sex (you deserve better than “okay”!!!), the question becomes: what do you want to do about it? I have a lot of follow-up questions that could possibly change the advice I’d want to give you (how is the relationship outside of the sex? How old are you? How long have you been together? etc.), so if you want to get more into the nitty gritty together, def write back in with more details! But here’s my gut instinct based on what you’ve shared:

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“I just got dumped, or, actually, he made me dump myself? I could tell something was up (very “I Fell Victim To The Three Month Situationship”) and kept leaving openings for him to cut it off. He didn’t, so I pushed the conversation, he broke up with me and said it was because he didn’t ‘feel a spark.’ We’d been seeing each other 2-3 times a week for 3 months, plus calls. Am I crazy or is the ‘spark’ something you figure out much earlier on than that? How do I avoid spending this much time with someone who is unsure of me in the future? Also...is there someone who will make it official by 3 months in their 20s and alive today in America? Help.”

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“Do you believe in right person wrong time? In other words, can two people really be great together but someone (in my experience the male partner’s) own personal issues just get in the way of them being together? Or if it was meant to be and he liked you enough, it would just work?”

Hello my love! Thank you so much for writing in <3

“Right person, wrong time” is a phrase we hear a lot in cases when we want to make sense of heartbreak that feels out of our control. It insinuates that you two were right for each other, but circumstances or logistics or life events are keeping you apart in a super romantic and tragic way. It also implies that there could be a right time in the future, which is reassuring.

But is this real? Or delusion? Let’s discuss.

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“I recently went out with my older brother and a few of his friends. I hit it off with one friend in particular… I followed him on instagram after and he followed me back instantly. He’s living in my area, far from my brother, and I want to see him. But the brother’s friend thing is always weird. Since he’s the friend, do I have to be the one to reach out? DM feels cheesy and it’d be so awkward if he wasn’t interested and told my brother. We all have the older-brothers-friend fantasy, but how do I go about this without being weird??”

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“I am trying to find my life partner and have been actively dating for several years with no successes. I recently took a break to freeze my eggs, and in doing so, I gained some weight and feel like I lost some of my confidence, particularly around my body. I have a long history of complicated feelings about my body and an equally long history of weight fluctuation, and I had finally gotten to a place of neutrality where I could be confident about myself in dating. I now feel like I took 1 step forward, 3 steps back. How do I go back to feeling sexy and desirable when I start dating again?”

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“I just started seeing someone and I want to have sex with him, but I feel really insecure about my lack of experience. I’m not very confident about my kissing, and I tend to laugh when I kiss someone because I feel embarrassed and self-conscious. On top of that, I know he’s slept with multiple people before me, which makes me compare myself even more. How much does experience actually matter in sex, and how can I stop getting in my own head and feel more present and confident during intimacy?”

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A little issue I’ve been encountering with your incredibly thoughtful, insightful questions is that I don’t always have the life experience to answer them. Especially when it comes to your questions about long-term relationships. Yes, I’ve been in a few 1-2 year relationships, and I’ve done enough therapy to guess what a healthy answer would sometimes be, but when it comes to things like “getting the spark back” and marriage generally, I’m simply not the gal for the job!

But I could never leave you all without answers. So this hump day, you have a very special guest advice-giver: my smart, stunning, superwoman married friend Hailey Andresen! Hailey and I met a few years back when we both worked at Departures—a luxury travel magazine that has since folded (rip). She was my boss but quickly became my bestie, and she has always been someone I look up to as a writer and general human being.

Hailey is married with two kids, so she is more than qualified to answer your relationship questions. If you want more from Hailey (which you definitely do), go subscribe to her Substack called FULL and check her out on Instagram! Fun fact about Hailey is that her and her husband have been married to each other twice…her lore goes so hard. If you ask nicely, maybe she will spill the tea on FULL. Okay, enough chat, let’s dive in!

As always, if you want to write in your own question, fill out the form here!

Okay so... Me and my boyfriend have been together for 4 years already and it has always been so good. However, we started dating when we were younger and that made us our first when it came to handjobs, blowjobs and sex. But he has never been able to make me finish. And now that I’m older I feel like I appreciate my own needs a lot more, so the fact that he never makes me O just bugs me and I’m starting to resent the sex a bit. Do you have any tips to get the spark back a bit?

First and foremost, I want to normalize how common this is. I have a vivid memory from my early twenties as a group of girlfriends shared how they had either never orgasmed, had only orgasmed while masturbating, or weren’t able to orgasm during penetrative sex. As someone who has never struggled with penetrative sex, I was shocked to learn this, but I was simply young and naive. Each of our bodies responds differently and there’s not one set way to get there. Transcending your early days of fooling around and firsts with your partner is a massive transition. Since it sounds like you two lost your virginity to each other, I would imagine there is a lot of learning and vulnerability tied up in sex for you two. Talking about intimacy can feel really nerve wracking in these dynamics, but it doesn’t have to be.

Considering you’ve been with your boyfriend for a long time, it sounds like you’re in a safe position to get really honest with your needs and what feels good to you. If you have finished on your own, you might need to enlighten him on what got you there. If you haven’t, then I think it’s something that could be really special for you to explore either on your own, with your boyfriend, or both. Come as You Are: The Surprising New Science That Will Transform Your Sex Life by Emily Negoski might help you tap into your personal pleasure too. It’s going to take some patience and practice to find your flow, but you deserve to finish!

My friends and I have been having an ongoing conversation recently on whether or not you should marry your best friend. Does your partner need to be your best friend? Is there a distinguished difference between a best friend and a lifetime romantic partner (aside from the sex, but maybe not...)?

While I love this question, I think there’s something more important to investigate here, “Do you want to be your partner’s best friend?” Our culture tends to put an immense amount of pressure on long-term romantic relationships. Expecting someone to be your companion, roommate, financial collaborator, monogamous or nonmonogamous lover, potential co-parent, and best friend feels like a tall order for most. In plenty of relationships, couples consider themselves best friends and that’s lovely. But, is it necessary? My answer’s no. So if that list feels like too much, it’s okay to hang on your bestie, and let your romantic relationship progress organically.

I will caveat this by saying, of course friendship plays a role in any romance — you want to actually enjoy your person’s company and appreciate who they are, same as you would a friend. As your relationship evolves you might naturally shift into the role of “best friends” with one another. But in the beginning, I believe it’s healthier to welcome a partner into your life that is already filled with sturdy friendships. Having this foundation only benefits your relationship, and allows what makes a romantic relationship special (intimacy and love) space to grow without the pressure.

Hi! Male reader here. I have been in a relationship with my girlfriend for 5+ years now. We have a great relationship and that translates into an awesome (and communicative!) sex life. Over the years, there have been things I’ve come across that I’m curious to try and it feels as though I have this block to even bring it up in conversation, even though we communicate well and often with each other. I would say it’s more of a personal anxiety about her reaction, but it isn’t like I’ve ever been met with a harsh response before. Acceptance or rejection of these sexual explorations is in no way a deal breaker, but I would be lying if I said I wasn’t curious to try. How can I approach the convo in a way that I’m being true to myself but also being respectful to her?

This is such a relatable question. Approaching the topic of fantasy, desire, or exploration can absolutely stir up anxiety, especially if you’re waiting until you’re in the midst of sex to do so. I’ve found that bringing up these topics when things aren’t as sexually charged creates a safer space to get honest. When everyone is fully clothed any potential rejection feels slightly less personal. Occasionally, leaning into that sexy new idea can work in the heat of it, but there can be something about the introduction of a new desire that could really throw anyone off if they weren’t expecting it. Of course, it might still feel awkward to bring up what that might be over coffee, but this is what it means to be in a relationship baby! And thankfully, it sounds like you and your girlfriend are already master communicators.

Confronting the topic from a place of not only wanting to share, but wanting to hear what your girlfriend might be into seems like a good first step. You might also find that sometimes talking about fantasy is enough to turn things up a bit, or at least a gateway to more hands-on exploration in the future. As you get deeper into this conversation with her, you both might enjoy the book Want: Sexual Fantasies by Anonymous. Let us know how it goes!

Okay so I may have done a bad thing (i.e. going through my bfs phone...) BUT not to read his messages or anything, I trust him. It’s just that I saw a notification on his lock screen that weirded me out big time. Basically it was from Depop and it said something along the lines of “check out these new listings that have been added to your search for ‘see-through lace dress’.” Like ummm I am intrigued. So I opened up his Depop and lo and behold all the recently viewed items are basically soft core porn! I need advice on whether or not to bring this up with him. I have no problems with him watching porn, as I do sometimes too. But is it normal to be looking at nakey girls on a RESELLING app?

OMG girl, you came with the TEA today! This is beyond fascinating—and I completely understand why that notification intrigued you. I have a few thoughts: First of all, the optimist in me wants to ask, is it possible that he was shopping for you on Depop? Like, maybe he wanted to buy you a sexy lace dress for Christmas? Let me know if you receive that present in the next few weeks because that would definitely answer some questions. But based on your reaction and his specific search history, it sounds like that’s not the most likely explanation.

I just did my own search on Depop for “see-through lace dress” (yes, this is investigative journalism) and very few nakey girls came up, so it seems like he had to be pretty intentional to find “soft-core porn” on there. But TBH, my instinct is that it’s not a huge deal…especially since you’ve already established in your relationship that you’re both comfortable looking at porn. When it comes to the porn itself—whether that’s a MILF video on PornHub or finding nudes on Depop—there’s really no such thing as “normal.” Everyone has their own weird turn ons, and so long as it doesn’t feel like it’s crossing a line or boundary for you (i.e. communicating with these girls, following them, etc) then I think it’s okay to let him get freaky on Depop.

Did you ever watch that episode of Friends where Monica thinks that Chandler is getting off to “Jaws” AKA shark shit? And she’s like this is super weird but I guess I’ll just roll with it? This is giving that same energy to me. Like, it’s definitely sort of strange, but if it’s not harmful or problematic, maybe it’s okay to just accept that your BF is doing something weird? But that’s just one gal’s opinion! If you felt more strongly I would completely understand!

If you find that it’s still really bothering you, I don’t think it would be crazy to bring it up, so long as you try to do so in a non-judgemental way. You could say, “Hey, I saw this notification pop up on your phone, and I clicked into it. I’m sorry for invading your privacy, I really do trust you. But now that I’ve seen it, it’s been on my mind, and I have a few questions.”

PLEASE update me queen! Thank you for writing in!

How do you approach convos with your parents and family members about sex and dating? I never tell them about dates I’m going on or girls I’m seeing casually. I feel like it’s awkward talking about girls because I’m gay (even though they’re chill with it), but I feel like everyone has this awkwardness too? It’s just so weird wanting to be a hoe but your family keeps asking about relationships but the dating scene is too weird to get one so there’s nothing to show for it ya know?

I FEEL YOU SO HARD! It’s honestly so awkward talking to your parents about dating, especially because it’s so different now then when they were on the scene—so it’s not easy to explain your situationship or random hookup or dating app debacles. You might think that it feels less uncomfortable for me since I put my sex and dating life on the internet, but in fact, it can be just as weird.

While my parents both subscribe to Railed to show their support, they refrain from reading the spicier pieces and we don’t usually chat about the content I share—that’s how we both like it. So it’s up to me to share any dating updates that I want them to know (I’m really never sharing “sex” updates with them. That feels too weird for me). My typical practice has been to update them when there is a person of significance, i.e. a boyfriend or almost boyfriend situation. As an avid dater and hook-up-er, I’m not keen on sharing every random guy I go out with because I don’t think my parents need to know about every man who crosses my path, especially if he will be irrelevant tomorrow. But if there’s a guy I’m seeing a lot who is a part of my life—someone who is in my stories, who I have consistent plans with, who would generally come up in conversation if I wasn’t trying to hide it—that is a person I would elect to tell them about. Often, it comes up naturally. My mom might ask what I’m up to on a given day, and I would reply, “I’m seeing Chad. He’s a guy I’ve been going out with! It’s going really well.”

A key component of my strategy relies on the fact that neither of my parents are nosy, nor do they ask me about my dating life unprompted. They typically leave it up to me to share something, and aren’t constantly asking me, “Who are you dating? When are you going to be in a relationship?” I’m not quite sure what I would do or say in that situation. I think it would be completely fair to let them know that it’s not something you’re comfortable chatting about, but confirm that you’ll tell them if there’s anyone they should know about. But on the flip side, if you like the idea of talking about dating with your parents but just feel awkward, I would encourage you to try and break the ice. Once you get past that initial weirdness, it gets a lot easier. And who knows, maybe they’ll have some wisdom to offer!

I hope this was helpful! Please let me know how it goes!

As a girl, how do I initiate sex with my boyfriend? Is it weird to literally be like “I want to have sex”?

GIRL, not at all! That couldn’t be less weird! Genuinely, if you just approached your boyfriend and said, “I’m horny, do you want to have sex?” I have no doubt that he would think that is the hottest thing ever.

You’re absolutely not alone in this struggle. I have so many women who write in asking me questions along the same vein: How do I tell my boyfriend I want to have more sex? How do I tell him I want to do anal? Or that I want to use toys? As women, we aren’t taught how to speak up and share our sexual desires—especially when it comes to something like initiating sex (or dates! or relationship steps! or really anything at all!), society tells us that that is the man’s job, and we just have to sit back and let it happen to us. The guy’s the one who’s hornier, who has the higher sex drive, who we are batting away because he wants to bang so much. But that’s just a story we’re told—it’s not at all true.

Us girls are horny too. We want sex. We have sexual desires and needs that deserve to be heard. So, while I completely understand why it would feel awkward to initiate sex, I would love to empower you to do so without shame. It could be as simple as telling him straight-up, “Hey babe, I really want to bang right now. You up for it?” or it could more subtle if that would make you feel more comfortable, like offering him a sexy compliment, or maybe you lean into physical touch (consensually, of course), and let your body language do the talking.

Go on and get that dick girl! Have fun!

Any advice on how to start masturbating? I’m a 21 y/o woman and I’ve never masturbated before, and I think that’s why I’ve never finished during sex. It might be dumb but I’m a bit intimidated with self pleasure.

Girl, that’s not dumb AT ALL. Masturbating is literally never taught to women—and not only that, there’s an entire culture of shame around female desire, making it that much more difficult for a woman to discover masturbation on her own. It’s just not made into a casual activity like it is for men—it’s much closer to an act of defiance, which is way more intimidating. So your feelings are completely valid!

I’m so excited for you to start this journey. There’s really no right or wrong way to masturbate, so I would recommend going into it with no rules, expectations, and especially no judgement. There’s nothing shameful about your desire, so have fun playing around and seeing what works for you! If there’s one thing I’ve learned, it’s that every woman masturbates differently, and there are a multitude of ways we all like to get turned on. When I first started masturbating, I was loyal to pillow grinding and watching horny music videos (i.e Lady Gaga’s “Poker Face” and Usher’s “OMG”). As I got older, I got my first vibrator and discovered PornHub, and I loved exploring the site and seeing what categories turned me on. Recently, I’ve been in my ~sex playlist era~, and I get off imagining past sexual experiences in my head as sultry songs play.

For getting started, I’d try to find some content that turns you on. Is there a sex scene from a movie or TV show that gives you fanny flutters? A smutty book chapter that got you excited? Or a category of porn that you want to try? Whatever interests come up, welcome them with enthusiasm—no turn-on is weird or wrong. I do think you’ll find that having some stimulating material—porn, music, movie sex scenes—will help to get the ball rolling and get your brain in the right headspace. To me, 99% of masturbation is mental—getting past that shame bit and letting your desires run free.

Once you’ve selected your entertainment (or lack thereof, if that’s your vibe!) it’s time to stimulate yourself. You can do this with your hands, a sex toy, or an object (just don’t stick anything crazy up there, please). I’m personally a fan of clit stimulation with a vibrator over fingering/using a dildo, so I love the Puff by Unbound. It’s a great starter vibrator that’s easy to use (not sponsored, just my personal pick!). But again, there’s no wrong way to do it. You might enjoy touching your nipples, fingering yourself, grinding on a pillow, using a dildo, whatever it may be. Give yourself the space to try different things, and start off gentle—i.e. don’t shove a large dildo up your vagina on the first go. Also, don’t put too much pressure on yourself to orgasm. It may take time and practice to figure out what gets you there!

I hope this helps, let me know how it goes <3 or don’t if that’s weird <3

Hello. I am a 27 year old straight guy who is a virgin. I technically have had sex before, although because it was not consensual (I was the non consenting party), I have been advised by friends that it does not count. I did not handle that experience very well and it resulted in me not feeling comfortable opening up to anyone for a long time. I am much better now and am trying to start dating, however every person I have shared that experience with has wanted to stop talking and seeing me after. So my question is, how do you effectively bring up being a virgin with someone you are interested in so they are not immediately turned off?

Thank you so much for writing in. I’m so sorry that you had that experience, and I find it beyond ridiculous that women who you dated are turned off by it. A value that we hold near and dear at Railed is that your body count—whether it’s zero or 100—says nothing about your worth or your sexiness or your potential as partner. If anything, these women should be turned on by your vulnerability and honesty.

My answer may not be the one you’re looking for, but I don’t think there’s a secret special strategy to telling someone you’re a virgin. Instead, I think that if a woman is turned off by that information—however you choose to share it with her—then she’s probably not right for you. Which is sucky, I know.

There are a lot of sexual expectations placed on men and women. Men are shamed if they aren’t having sex enough, and women are shamed if they are having sex too much. You’re facing the former, I’ve faced the latter, both are incredibly unfun and unfair. I’ve had men reject me for being too sexually “out there”, and many times I wondered if maybe I should have held my cards closer to my chest or played things differently, but I’ve learned over time that the right person won’t care. I have no doubt that you will find an awesome girl who couldn’t give two shits whether or not you are a virgin and is honored to help give you a positive experience with sex in the future. Sending you all the love! You got this!

I’m having an issue where my boyfriend isn’t talkative during sex. I’m talkative, and he’s physically dominant which I like, but I need the occasional “good girl” and what not. We’ve only been dating for a month and seeing each other for 2.5. Is it weird to ask??

Omg girl it’s not weird at all to ask! You absolutely should! I bet that man would love to call you his good girl if he knew you were into that. Getting someone to talk during sex is a bit tricky, so I completely understand the position you’re in, especially since you’re already talkative and he’s not naturally matching that energy. I’m so glad you wrote in!

As a first step, I would try asking him sexy questions during sex to make the dirty talk a tad more interactive (if you aren’t already doing this). “Do you like that?” “How does that feel?” “What do you want me to do to you?” You could even go as far to say “Am I a good girl?” to tip him off that you want him to say it. Hopefully by asking him these questions, you’ll make it more obvious that hearing his voice during sex is a turn on, and he might naturally get more comfortable talking. A lot of the time when people are quiet during sex, it’s not that they don’t want to talk, but they feel nervous or don’t know what to say. Some guiding questions might help!

If that doesn’t do the trick, don’t be afraid to tell him straight-up what you want. A good time might be during foreplay as things are heating up, you can tell him, “I love anytime you talk dirty to me, and it would really turn me on to hear it more.” This might even open up a convo for more things you both want to try during sex, which is great!

I hope this helps! Hope you get that good girl affirmation soon!

Hey girl! So I’ve been talking to this guy, and he loves pictures and nudes, but I’m so lost on where to start. I feel like my vagina just looks weird and I don’t even know how to pose, what to take a picture of, or how much to show?

GIRL. I totally feel you. Taking an artful nude is honestly so difficult, and the angles themselves feel impossible to master. I can’t tell you how much time I’ve spent bent over like a pretzel trying to take a non-scary photo of my vagina. I’ve really been there—so let’s discuss.

First of all, the big sister in me wants to remind you to be cautious of who you’re sending nudes to—and why you’re sending them. Not AT ALL to say that you shouldn’t be sending them. Nudes can be super fun and spicy, and honestly it’s just a naked body so it’s not that deep. But I noticed in your question that you said he really likes to receive pictures, so just make sure that it’s something you enjoy to do as well! If you realize that you’re just doing it for him, then maybe it’s not the right activity for you two to share.

Okay, I’m done being a buzzkill. Now, let’s discuss how to take these pics. For me personally in my nude-sending era, I would typically focus on sending photos of my boobs and butt. Especially if this is a new exchange or someone you’re still getting to know, that tends to feel less intimate than a full-on vagina shot. For butt photos, I found that a mirror selfie typically did the trick: Your ass is facing the mirror but you twist your arms/back around so you can take the pic. If you’re twisting your back to the left, try stacking your right leg over your left leg. I’ve found that this can make your butt look a little bigger.

For boobs, there’s less of a science. You could do a mirror photo again, focusing on the top half of your body, or you could do a selfie, only including your chin and below for some anonymity. Also, don’t be afraid to keep some lingerie on in either of these photos! It can add to the suspense and be something that you take off if the exchange gets more heated.

As for photos of your vagina: I completely get feeling like your vagina looks weird. But I promise that the guy won’t think that—it’s just that as women, we have been conditioned to think our vaginas are gross and need to smell like roses. And also, we don’t get a good look at our vaginas all that often, so any close-up photos can be a bit of a jump scare. From my experience, I’ve found it more comfortable to do an action shot or video of said vagina—i.e. touching yourself, using a toy, etc. That way, I have some sort of prop. LOL.

I hope that this was helpful!! I hope you get some good dick pics in return!

How do I ask a girl to come visit me and tell her I’ll pay for her to fly in a way that doesn’t come off cocky/douchey?

“I’ve loved getting to know you virtually, and I would really love to meet in person so we can further this connection. Would you be open to visiting me? If so, I’d like to cover the costs of your flight and visit, since you’d be doing the work of traveling here.”

Nothing douchey about paying for a flight, trust me.

I’m casually seeing someone. He’s cool and all, but last night he told me that I give good blowjobs but I’m not a good kisser. (Honestly, I know I’m not the best kisser in the world and most of the time I don’t know what to do with my hands or anyone’s tongue. He’s the first one who’s ever told me that, and he kind of offered to “train” me during our few encounters). But as someone I trust, could you give me some tips to get better at kissing?

OMG why am I blushing for being considered someone you trust :,) It makes me so happy that you’re reaching out with this question! Funny enough, in college I actually went through a phase where I completely forgot how to kiss. I literally watched “how to kiss” YouTube videos because I felt like I had no idea what I was doing—despite the fact that before that, I had been a totally sufficient kisser.

This is all to say that you should feel no insecurity around this development. Sometimes, I think it has to do with the other person and how you are meshing together. He might have a different kissing strategy that you aren’t used to! I like that he offered to help train you—that honestly sounds hot to me. But I do hope that he offered you this feedback in a kind way (I feel like saying you’re good at blowjobs but bad at kissing could be kind of harsh?? But maybe he said it nicely?). This man should feel blessed that he gets to be smooching you regardless of your kissing style.

Now, let’s discuss kissing tips.

1. Lean into the energy of the other person and use their movement as a guide—he is your dance partner, and it sounds like he is down to lead.

2. Start slow. Let the kisses feel sensual and purposeful. Don’t rush into heavy making out that moves really fast, or you could end up just slobbering all over each other in an un-hot way.

3. The tongue is an extension of your mouth—not a surprise jackhammer. The use of tongue during making out can be tricky. As a best practice, I would start without it, and let it naturally join. It should go with the movements of your lips, making an appearance when you open your mouth—again, being smooth and sensual. The worst thing you can do with your tongue is poke it out aimlessly. This is something that will absolutely get easier with practice!

4. Explore other places you can kiss! The neck, ears, chest, etc. are all fun places to kiss and can be a fun way to tease and play with your partner.

5. Let your hands explore as well. You can run your hands through his hair, up and down his arms, play with his belt loop, or if things are getting steamy, use your hands to feel up his dick. Have fun with it!

I hope these tips were helpful! Let me know how it goes <3

Any advice for a dude dealing with delayed ejaculation? I keep making girls feel bad for what isn’t their fault and feel horrible about it. (I don’t know why it’s happening).

Hey slaying sir! I’m so sorry you’re dealing with this, I know it must be frustrating, but I really appreciate you writing in! If it helps, I’ve slept with around 20 guys, and I feel like at least half of them dealt with delayed ejaculation at some point—so it’s probably way more common (and less of a big deal!) than you would think. Because I’ve had experience with this, I’m able to understand that it’s not my fault, but I get how some girls may not have that same mindset off the bat. So let’s chat through how to make you, and them, feel better!

First of all, I want to remind you that being a good sexual partner really has nothing to do with whether or not you finish. There’s so much pressure put on guys and their dicks during sex, but I promise that girls actually care way less about your “penis performance” and way more about how you actively pleasure them—through oral sex, fingering, kissing, affirmations, etc. When I’m discussing sex with my girlfriends, you would never catch me saying shit like “yeah, he came inside me really fast, it was so yummy!” I’m waaaay more likely to say “yeah, he went down on me for so long, it was so hot.” As much as you can, try to take the pressure off your penis.

For your course of action, I’d recommend communicating with your sexual partners about this in advance. For me, it’s hard to finish with a guy, especially when it’s one of our first times together. I find I can be much more relaxed if, as things are heating up, I tell him, “Just so you know, I probably won’t orgasm tonight. It’s really hard for me to finish with a new person, but it doesn’t mean I’m not enjoying myself. And I’m so excited for you to fuck me.” That way, they know it’s not about them, and I don’t have to feel like I’m forcing myself to cum—or worse, fake it. If you feel comfortable, try doing the same! Let the girl know beforehand that you sometimes have trouble finishing, so that way she won’t feel bad if it doesn’t happen, and you don’t have to stress.

If you want more advice on this topic, I wrote about it in another Railed post here! I hope this was helpful. Good luck king <3

I’m a girl, and I’ve never been bold with guys before. But I just got out of my first relationship and I now feel confident dating others. There’s this cute guy I met at a party and I’m considering asking him out, cause what’s the worst that could happen, but my friends told me to not make the first move/force the first move. I’m usually good at telling whether someone likes me, but we’ve only seen each other in person once when we met. Do I ask him out or lead him to? Or move on?

OMG GIRL your friends are majorly steering you astray! You should absolutely go for it and make the first move! The narrative that only men should initiate romantic connections is unhelpful to both men and women—it puts the pressure and burden on men while taking all agency away from women. It’s a lose-lose situation. So I am all for the girlies taking control of their lives and making the first move! Personally, making the first move has been integral to my success in the dating pool. If I never messaged first on a dating app, approached someone at a bar, or asked a guy out, I would probably have ended up a nun. Both of my long-term relationships started because I made the first move, and all the hottest guys who have graced my roster were there because I took a risk and initiated things.

I’m telling you, guys love it when they don’t have to make the first move because they are so accustomed to that pressure being on them. And in my experience, they tend to think it’s hot when a girl has the confidence to ask them out—if a guy thinks differently, he’s probably an insecure loser with dated beliefs about gender (AKA, not the guy for you).

TLDR: Go for it and ask that guy out! Make his day! If he’s taken or for some reason it’s not a match, he will still be so flattered! And your act of bravery will be great practice for the next time you want to make moves on a hot guy! YOU GOT THIS QUEEN PLEASE LET ME KNOW HOW IT GOES!

Hi Gal! I have been single for 9 months after a long term relationship and am ready to get back out there in a casual sense. How do you navigate casual hookups? I’ve never done them before and I’m wondering how they work? Thanks chicky!

Hey back! I’ve never called my friends chicky before but I lowkey love that and am going to steal that from you! This is such a good question, and there are honestly so many unspoken rules of casual hookup culture, so I’m thrilled we get the chance to talk through them. There’s a big narrative out there that women always want serious relationships, but I’ve been in so many phases of my life where all I want is casual sex—and there’s really nothing more empowering than knowing that and getting exactly what you want. So welcome to your Samantha Jones era! I’m so excited for you! Let’s dive in.

THE RULES OF CASUAL HOOKUPS

1. Always drinks, never dinner. If you’re meeting up with a Hinge match or going on a first date that you want to keep casual, always stick to drinks—it’s waaay less serious and committal than a dinner (or, god forbid, a coffee date). If you end up hanging out again and it’s clear the vibes are casual, you can even skip the first location and suggest meeting up at one of your places ;)

2. Be honest and upfront. Try to generally let the other party know that you’re just looking for a hookup. That way, if they’re looking for something more serious, you can part ways without feelings getting hurt. And don’t let any man make you feel weird or bad for just wanting a fuck.

3. Keep the texting to a minimum. No spontaneous updates about your day. No “this song made me think of you.” If you want to achieve a strictly casual hookup relationship, your communication should pretty much only be about making plans to bang.

4. If they’re not a good fuck, move on. What’s the point in a sex-only relationship if the sex isn’t good? If the physical chemistry isn’t there, or they aren’t listening to your needs, or they won’t go down on you or something crazy like that, it’s probably time to find a new fuck buddy.

5. Condoms! Condoms! Condoms! Enough said.

6. Don’t meet the friends. And don’t introduce them to yours. That’s strictly boyfriend territory. Your friends should really only know this person as the illusive “guy number two from Hinge” or “random you met at Nublu.”

7. Do what you have to do to avoid catching feelings. This step has always been a bit tricky for me. I’m someone who inherently gets attached after sex and can romanticize the evil out of just about any man. But there are times when I know I don’t want a relationship, so I have to make sure my hookups stay in a very specific box in my brain. I don’t text them too much. I don’t spend too much time getting ready to see them. And I try to remind myself of why we aren’t a real match.

GOOD LUCK CHICKY!!

Masturbation ethics? I'm a guy who grew up on the internet, so pictures of the people I know are as prevalent as pictures of celebrities and sex icons. Naturally - I think - I'm often aroused by pictures of people I know on my feeds. Is there anything wrong with using pictures of acquaintances to fantasize and masturbate? What's the line where it is weird?

Wow, what a great question. Here’s my take: You can do whatever the fuck you want when you masturbate. No sexual fantasies or turn ons are weird or off-limits. It’s a totally private time, and no one has to know who or what you jerked off to. There are really only a few scenarios where I think it could become weird, and it doesn’t sound like you’re at risk of doing any of these, but let’s map them out just in case:

1. Jacking off to photos you have of someone that you shouldn’t have, i.e nudes you got without permission, nudes you’re holding on to without permission, etc. 

2. Saying something weird to the person you jacked off to. It seems obvious not to do this, but there are plentyyy of men out there who would slide into a girl’s DMs to let her know she got him off virtually. So don’t do anything icky like that! Just keep it to yourself.

3. IDK I honestly can’t even think of a third, your sitch sounds kosher to me!

The great thing about masturbation is that it’s only between you and yourself, so it’s okay to be turned on by something or someone that you may not want to advertise to the whole world. I’ve masturbated to porn that plays on some rather fucked up themes (incest vibes, for example), but we aren’t going to judge ourselves for what turns us on!

Also, maybe this is just me, but sometimes I find myself masturbating while I’m just scrolling through TikTok in a parallel play kind of way—like, I’m not masturbating TO TikToks, but more so, WHILE watching. And then, there are occasions where I orgasm but something happens to be on my screen like a puppy or Moo Deng or some influencer and I’m like EW I DIDN’T MEAN TO ORGASM TO YOU! But you know what, it happens! Masturbation is weird idk. I hope I answered your question!

Heyy!! How can I get better at flirting with/seducing a man? I always feel awkward showing interest even when a man who’s clearly my type is staring from across the room. What do I do?

First of all, thank you so much for reminding me about the word “seduce.” What a sexy word that I hadn’t thought about in so long and must put back in my vocabulary! Secondly, you are so real for this question. Flirting is lowkey scary, and it’s not as easy as they make it look in all the rom coms. 

My number one tip for learning how to flirt? Practice. Flirting, dating, seducing, all of the above—these things are muscles that you have to flex in order to learn, IMO. The best way to get comfortable approaching someone in a bar? Do it over and over again! The first time might be nerve-racking, but it will get easier every time. The same goes for flirting. If you feel like you don’t know how to talk to guys, download a dating app and start chatting with people. Or if you want to get more comfortable while on dates, go out with a random Hinge match who is probably not your husband but seems nice! Start yourself off in low stakes scenarios where you can just practice for fun. 

So, we’ve established that you gotta get your feet wet to learn how to flirt. But let’s talk about what exactly to do in the scenario you described: There’s a guy across the room who’s totally your type, and you want to show interest but feel awkward. 

Step 1: Try everything in your power to not ~feel~ awkward. The best flirting comes from a place of confidence–which is something you can build from practice (what we talked about above), but it’s also something you can try to fake. Maybe take a shot, get a girlfriend to hype you up, or do whatever ritual you have to do to get a little confidence boost. 

Step 2: Have a little across-the-room-convo. Hold eye contact, smile, and maybe even give a flirty wave. This is a great in-between step if you’re feeling too nervous to approach, so hopefully this will signal him to come over!

Step 3: If he doesn’t come over JUST APPROACH HIM BABE UR YOUNG AND HOT AND WHY NOT?! GO BLESS THAT MAN WITH UR PRESENCE! REMEMBER: IT’S FOR PRACTICE!

Step 4: Compliments break the ice. “I love your shirt! You have such a great haircut!” etc. But a little teasing makes way for some subtle seduction. Lightly roasting a guy can be a great way to turn up the heat—and tension—in a convo.  

It sounds like you have a particular interest in not just flirting but seducing, so let me share a few more quick hits in the ~art of seduction~:

1. A lot of seduction is in the eyes and mouth. Try to hold eye contact throughout your conversation, and smile, laugh, maybe even bite or lick your lips—that’s show biz, baby! 

2. Directness is hot. Don’t be afraid to be straightforward about what you want and what you’re thinking. “You’re so hot,” or “Let’s go outside and make out” are all acceptable options in my book.

3. Consensual touching is key. Touch his arm teasingly, brush knees under the table if you’re seated, that sort of thing. 

4. When you want to talk about seduction after you’ve left the bar, LMK and we can have that convo, too ;)

You got this queen! Get after it!

I want a woman's perspective. I love to climax via...tit fucking. Is there any pleasure in this for the other partner? I have partners enthusiastically consent to this but I wonder if it's actually a good feeling. Just curious!

What an interesting question! I honestly haven’t partook in titty fucking myself in quite a long time, but if I remember correctly, there’s no specific pleasure points it’s hitting—but it definitely doesn’t feel bad. It’s possible it feels nice if it’s sorta rubbing against your nipples? But I don’t think I’d personally be like omg yum I’m gonna orgasm from this penis between my breasts if that makes sense. However, if a guy really liked it I’d happily participate as it doesn’t feel unpleasant in any way!

Did this at all answer your question? Who knows! Maybe ask your partner if she enjoys it—she might think it’s super hot!

I legitimately hate blow jobs. My jaw locks open (ouch), I never have enough spit, and I have a sensitive gag reflex. I want to be sexy and turn partners on (and I want them to eat me out!), but I just get so in my head that I end up anxious. Help! 

Hey girl! This makes a lot of sense! Shoving someone's genitals in your mouth isn’t always a cake walk, nor is it without struggles and anxiety. I’ve written about BJ tips and tricks if you’re wanting to learn some hacks, but I think it sounds like you genuinely don’t enjoy sucking D! In fact, you even used the word “hate”! To me, that means you simply shouldn’t do it. During sex—whether it’s foreplay or oral or penetration—we all need to get in the habit of not doing things we don’t like. IK, that’s a Captain Obvious observation, but it’s way easier said than done. 

I get that you may feel weird about not giving head altogether because you want to please your partner. But if you’re really hating it while you’re doing it, I don’t think he’ll be happy either (or at least, if he’s a good, normal person!). I’d recommend becoming a handjob master, or maybe leaning into a very hands-heavy blowjob technique, using your mouth to occasionally lick or spit while your hands do the heavy lifting. Or if that isn’t your cup of tea, take the time to explore what you really do enjoy in bed that pleases both your partner and you. I’m not shy about the fact that I love giving blowjobs, but I also hate getting on top, so I rarely do it. Maybe you love getting on top! Maybe you love giving a foot job! Who knows!

I promise that this won’t make you less awesome in bed—it will just help you enjoy it more, which is super important! Oh, and BTW: Just because you don’t give someone a blowjob doesn’t mean they can’t or shouldn’t eat you out. Who knows, that might be their favorite part!

I have tried and tried to give my girlfriend a great experience going down on her, but she always pulls me up. She says there’s something wrong and that she only enjoys stimulation with my penis. I won’t give up because I know there’s a technique out there that will work for her.

Hi there! I love that you’re so committed to making your girlfriend feel good, and it’s a great sign that you’re writing in this question to try and improve her experience. However, I think the best way to ensure her pleasure is to listen to her requests and needs—and it sounds to me like getting eaten out just isn’t her favorite thing. This isn’t unheard of! I enjoy getting eaten out, but I actually prefer fingering even more—and I know I’m not the only girlie who feels this way.

Here’s how I would recommend proceeding: Don’t push it on her (not that you are!). If you’re hooking up and it’s getting to that point, you can ask if she wants you to go down on her, and if she says no, just skip it! And before your next hookup, I would initiate an honest (and lowkey sexy) convo about what really turns her on. Does she like being fingered? Teased? If penetration is her fave, what positions does she like best? Emphasize that your top priority is making her feel good, and do your best not to make her feel weird or ashamed for not wanting head. And maybe most importantly, don’t let your own ego get in the way (again, it doesn’t sound like you’re doing this, it’s just a preemptive warning!). It’s totally possible that her not wanting you to eat her out makes you feel bad—I know if a guy told me he wasn’t liking my blowjobs, I’d be lowkey offended. But it’s crucial to put that aside in this situation, because you don’t want to make her feel worse or like she’s hurting your feelings!

If, after chatting with her, you get the sense that she actually does want head but just wants you to try a different strategy, then that’s awesome feedback and you should go for it. If you want some tips for eating out, check out this post I wrote!

I’m in a very committed, healthy, happy, straight relationship of 4 years. I want to marry him. However, I’ve always wanted to explore sex with women but don’t know how to approach it and the ethics of it. Is exploring a sexual fantasy worth potentially causing a major rift in my incredible relationship?

What a real question. I want to start out by making it clear that this isn’t my expertise by any means—I’m a straight woman who hasn’t personally felt called to explore sex with women. But if you’ll have me, I’d love to still try and be of help! 

What struck me most about your question is the statement that you want to marry this man. You’re pretty locked in and see a long-term future with him. So my question for you would be, what would you want to get out of exploring with women? Would it be just so you’ll know once and for all if that’s for you? Or is it more of a fantasy fulfillment? I would recommend asking yourself, is this just for fun/because it sounds hot? Or would you feel unfulfilled or even resentful of your boyfriend if you don’t explore this part of yourself? If it feels more like the latter, it may be worth seriously exploring before committing to a lifetime with this person. 

I love that you asked me this question, but I think the next step is to honestly talk to your boyfriend. It doesn’t need to be a conversation of a breakup or a break or anything scary like that! It could be as simple as letting him know that, “Hey, I’ve been questioning my sexuality recently. I see you as my future husband and I don’t want to do anything to jeopardize our relationship, but I want to be my full authentic self with you and felt like this was something you should know. I wonder if we could talk through what this might mean and look like for us.” You may feel some sense of relief and power simply in just bringing this to the table! 

I hope this was helpful! Let me know how it goes if you decide to have a convo!

Let me tell you a bit about this queen. In her 20s, Tal was doing everything “right.” Or so, she thought. She was dating men, grinding at the New York Times, and becoming a corporate girl boss—who was drained AF. But a few years ago, she took a risk: She quit her job. She came out. And she found a new way to live authentically as her true self—pretty fucking cool of her if I do say so myself.

Flash forward to today, Tal is out as queer and poly, and she continues to rewrite her own story with her very own rules. Plus, she has some pretty epic sex and dating stories that always blow my mind—if you ask nicely, maybe she’ll tell you some! Head over to her Substack—Outside the Lines—for her thoughtful, honest reflections on identity, self-love, relationships, and more.

Now, let’s dive in as she answers your fabulous questions! As a straight woman who’s only ever been monogamous, both queerness and polyamory are obviously a blind spot for me, so I’m so honored and grateful to have Tal’s expertise. Everyone say thank you Tal! And subscribe to OTL WITH TAL! 

How do you facilitate non monogamy.... poly? open? What does it mean when my partner wants to see other people but not break up?

Ah yes, welcome to the beautifully chaotic portal of “Wait, so are we breaking up or opening up?," a question that’s cracked open many a queer heart and Google search bar. First things first: non-monogamy is an umbrella with many possible dynamics underneath it: open relationships, polyamory, relationship anarchy, monogamish, and more. Each one requires intentional design. Think of it like building a house together—you could just knock down a wall and see what happens, but it’s safer (and sexier) to start with a blueprint.

If your partner wants to explore connections beyond the relationship but still stay together, what they’re expressing is not necessarily a lack of love, it might actually be an expansion of it. That said, opening up a relationship doesn’t fix what’s broken. It magnifies what’s already there. So before you start comparing calendars or redownloading dating apps, slow it down and check in. Opening up is not something to rush into without first doing the work.

1. Start with your “why.” 

Are you curious? Seeking freedom? Wanting more intimacy, more play, more opportunities to grow? Or are you hoping that opening up will save something that's fading or fill a void you are trying to ignore? Or (a definite flag to pause and reflect!!), are you only doing this because your partner wants it? Be honest with yourself and each other. You can’t build secure attachment if you're unclear on what you're attaching to, and you can't open up ethically together if it doesn't feel safe for both of you.

2. Design your relationship consciously.

 "Open" and "poly" aren’t synonyms, they’re structures. Open typically means sex outside the relationship, while poly implies multiple relationships that may include physical, emotional, and romantic connection (poly = many, amory = love, so it literally means “many loves”). Relationships structures are not one size fits all, and neither is more advanced or better, they’re just different. Many couples create beautiful hybrid models: one partner more poly, one more open, even one more monogamous. The point is intentionality. You are the architect here, so build what fits YOU.

3. Do your research and talk about everything, especially the awkward stuff. 

Jealousy? Normal. Fears? Unavoidable. Bizarre hypotheticals? Encouraged. This is where you want to do your research and talk it all out. I'd recommend resources such as Polysecure, More Than Two, Ethical Slut, and creators like @chillpolyamory, @decolonizing.love, and this must watch podcast on all things poly. Take time to define your boundaries, needs, intentions, desires, and deal-breakers, and let them evolve as you do.

4. Practice secure attachment and honest communication even when it’s uncomfortable or messy. 

Opening up is less about being “chill” and more about being real. Create rituals of reconnection. Discuss aftercare. Reassure each other. Normalize big feelings. Opening up will stretch you, but that’s where intimacy lives. Secure polyamory doesn’t mean you never get triggered. It means you know how to return to love.

Remember, no one knows what they’re doing at first. Life is just one giant experiment, and exploring open relationships is too. You will learn as you go. Just do your best to stay curious, compassionate, communicative, and true to yourself. 

I can’t tell if I like guys or not. This guy was into me and I could see myself dating and cuddling him…but nothing else. Any advice on knowing if it’s a real attraction or if you just like the idea of it/the attention? 

You are SO not alone in this, and the fact that you’re even asking this question already shows a beautiful level of self-awareness. Attraction is nuanced. Sometimes it shows up as a spark, other times a slow burn, or, in some cases, just a soft glow from the idea of being desired. So how do you tell the difference?

Sometimes we crave what looks good on paper (or what feels validating when we are wanted) but when it’s time to actually dig in, the hunger is not really there. There’s nothing wrong with liking attention. In fact, many of us (especially those raised as femme or assigned female at birth, but even those assigned male at birth) were conditioned to seek male approval from childhood. Think: Disney princesses, rom-coms, the ever-present cultural script that says being desired or accepted by a man = being worthy. This social wiring can confuse our internal compass.

So instead of just asking “Do I like him?” try asking:

• What does my body say? 

• Do I feel pulled toward him? Lit up around him? Or just… calm, meh, or closed off?

• What are the signs that helped me know I was into someone in the past? 

• If he stopped giving me attention, would I still be interested?

• Would I want to kiss him if no one was watching and if nothing else came after?

• What pressures might be coming from outside of me to feel a certain way about him?

Attraction lives in the body, not just the mind. And while bodies are wise, they are also shaped by trauma, attachment patterns, and socialization. So if you feel confused, that’s normal. It’s not a sign something’s wrong, it’s a sign you’re paying attention. And that being human is hard!!

I’d also personally recommend loosening the labels. Sexuality is fluid, not a checkbox. Maybe you’re into this man but not all men. Maybe you’re more emotionally drawn than physically. Maybe you’re still figuring it out. All of that is allowed. You don’t have to commit to a category; I firmly believe that you are allowed to evolve. Don't rush to name it. Let yourself explore, let yourself want what you want, and let yourself outgrow what no longer fits as you go. It’s all data. Think of yourself as a sexy scientist running your own experiment. Go test some hypotheses and see what feels true in your body!

When a break of trust happens (emotional or physical cheating) is there a way back to a healthy relationship? And is ethical non-monogamy something that might be on the mind of the person cheating?

The most important part of ethical (or consensual) non-monogamy is… well, the “ethical” and “consensual” part. That means building trust, keeping agreements, and doing our best not to hurt the people we love, especially by not lying or sneaking around.

So let’s be clear: cheating is not the same as being non-monogamous. One breaks trust; the other requires deep trust to function. I’ve had a partner lie and cheat and then claim it wasn’t a big deal “because we used to be open.” No. That’s not how healthy relationships work, open or otherwise.

Can you come back from cheating? Sometimes, yes. But it’s not guaranteed, and from what I’ve seen, it’s never easy. It takes radical honesty, shared accountability, and a deep recommitment to making each other feel safe again. That goes for both people. The one who was cheated on needs to actually feel safe and trust again. And the one who cheated needs to be willing to own what they did, explore why it happened, and make amends in a way that truly lands. Also: it’s okay to decide it’s not worth it. Healing after betrayal takes work. Not everyone wants that job, and not every relationship is meant to survive it.

Now, if someone cheats and then feels like it’s because they’re secretly non-monogamous, that could be true… but it doesn’t make the betrayal okay. The desires might be valid, but they still broke a shared agreement. Queerness, polyamory, desire–they all deserve compassion. But compassion doesn’t cancel out consequences.

So what’s the path forward? Ask the real questions: Can we rebuild trust? Can we both feel safe here again? Are we both willing to do the work, not just to repair, but to evolve into something new? And then, just as importantly, are we both comfortable with each others’ visions for what we are evolving into?

Sometimes betrayal is a rupture. Sometimes it’s a reveal. And sometimes, if both people are truly committed to healing, it can be the beginning of a much deeper and more beautiful reality.

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!

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

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!