Once a pretty physical act, sex is now well established in the digital realm. From an overwhelming amount of increasingly unique porn to the wild west of AI sexbots, we’re still very much figuring out how to navigate the modern sexual landscape. Who better to guide us than sex educator Shan Boodram, who’s returning for this installment of Playboy Advisor to answer your hottest questions. Here, Boodram tackles late-night porn rabbit holes, vibrators as friend (not foe), and so much more.

I’ve been single for a while now and I’m experiencing a bit of a dry spell—so naturally, I spend a lot of time scrolling through Twitter porn. In the past month or so, I’ve found that I’m searching more and more for kink porn to help me get off. I keep wondering if I’ve always been into this kind of thing, or if my late-night bate sessions might be leading me down a rabbit hole. How do I tell the difference?

Porn, by its very nature, does have an escalation factor, especially once it’s become a compulsive sexual behavior. The logic goes, the more porn you watch and the more exclusive you are to porn as your medium for sexual release the more you may need more shocking, more intense porn to finish. Research on habituation and the brain’s reward system shows that repeated exposure to the same sexual stimuli can reduce arousal over time, leading some people to seek greater novelty or intensity to achieve the same effect. Studies on compulsive pornography use specifically find patterns of escalation, novelty-seeking, and desensitization, similar to tolerance mechanisms seen in other reward-based behaviors. So introducing variation, such as imagination, memory, or different forms of erotic stimulation, may help disrupt this loop and reduce the drive to constantly go deeper, harder, or more extreme in ways that can start to feel uncomfortable.

I’m seeing this new girl and recently, in the middle of the act, she pulled a vibrator out from her drawer and started using it on herself. I kinda felt slighted—but am I overthinking it?

Short answer: yes, you’re overthinking it.

Better answer: it’s worth thinking about, just not in the way you think.

This isn’t about your performance or something you’re doing wrong. It’s about how orgasm actually works for most people with vulvas. Penetrative sex alone often isn’t enough for orgasm because the vagina does not have the same density of nerve endings associated with reliable climax. The clitoris does. Anatomically, clitoral stimulation is the closest equivalent to penile stimulation in terms of sensitivity and orgasm potential.

A toy during penetration is not a replacement for you. It’s an enhancement. Think of it the same way many people with penises enjoy prostate stimulation in addition to penile stimulation (aka The Rusty Trombone). Adding more sensation does not mean the original sensation is lacking. It just means pleasure stacks. So instead of taking it personally, take it as information. Let her use the toy, or even better, ask her if you can use it on her and/or ask her if she’d like it if you rubbed her clitoris with your fingers during penetration. It’s not about competition, it’s all about collaboration and communication!

There’s a girl who I have an ongoing, strictly sexual relationship with. It’s always a good and easy time, and I really like our dynamic. The only thing is, she’s recently started to ask for rougher play, like slapping and choking, during sex. I don’t have a problem with rough stuff—but I get kind of nervous about it, especially if for whatever reason, we stop hanging out or things get weird. How do I give her what she wants, but make sure I don’t become the bad guy?

This is a genuinely thoughtful concern, and you’re far from alone in it. In The Second Coming, journalist Carter Sherman explores how Gen Z’s sexual landscape is shaped not by a lack of desire, but by uncertainty, anxiety, and confusion around sex, power, and consent. One of her key findings is that many men are deeply concerned about doing harm or being misread. And in a world where people share more and more of their lives online, that concern now also extends to reputation, context collapse, and how a private sexual dynamic might be perceived if it ever becomes public.

What you’re describing doesn’t sound like discomfort with rough sex. It sounds like concern about safety, consent, and what happens if the relationship ends and intentions are questioned later. That’s not paranoia. That’s an understandable response to a cultural moment where sex doesn’t just live between two people anymore, it can live on screenshots, group chats, and social feeds.

The solution here isn’t guessing or managing your anxiety in silence. It’s clarity. This is exactly the kind of conversation to have directly with your partner, framed as you’ve framed it here: you want to give her what she wants, and you want to make sure both of you feel safe, respected, and protected.

This is also where frameworks like RACK (Risk-Aware Consensual Kink) come in. Rougher play, especially things like slapping or choking, carries real physical and emotional risks. Educating yourself on those risks and talking about them openly allows consent to be informed, mutual, and ongoing. From there, set clear boundaries, talk about aftercare, and agree on a safeword. Safewords exist because sometimes “no” or “stop” can be part of the fantasy, so you need a word that always means “this is real, slow down or stop now.”

If you lead with transparency, education, and care, you’re not positioning yourself as the bad guy. You’re modeling the kind of sexual responsibility that Sherman argues is missing right now: conversations that happen before harm, not after.

Call me crazy, but there’s literally not a day of the week I wouldn’t have sex with my girlfriend—yes, even when it’s that time of the month. She’s still sexy to me, even if we do have to clean the sheets after. But she insists that it’s gross, even if I just want to make her feel good. Do I need to back off?

I won’t call you crazy, and also you’re not wrong for finding your partner attractive during her period. For many, attraction doesn’t shut off during menstruation, and for people who have periods the same applies! Period sex means increased sensitivity, a decrease in cramping, and easier access to the A-Spot because the vaginal canal shortens. So from a biological standpoint, period sex isn’t inherently undesirable, unhealthy, or dangerous for consenting partners.

That said, it sounds like her reaction isn’t about logic or hygiene, it’s about conditioning and body shame. Many people who menstruate are taught from a very young age to conceal, deodorize, and treat their periods as something embarrassing or contaminating. That messaging sticks. When someone internalizes those beliefs, being desired during menstruation can feel confusing or even violating, not affirming. Consent research is clear here: wanting to make someone feel good doesn’t override how they feel in their body. If she says it feels gross to her, that boundary matters, even if your intention is loving. Pushing past that, even gently, can turn affirmation into pressure. Where you can lean in is exactly where you’re already headed. Continue affirming her desirability in ways that aren’t contingent on sex. When people feel emotionally safe and unpressured, they’re more likely to revisit boundaries on their own. So, if her feelings ever change, great! If they don’t, that’s also okay! Attraction is natural, but comfort sets the pace. 

I’m just gonna say it: I have been thinking about asking my girlfriend if we can try butt stuff. (Mine, not hers.) How do I ask without making her worry that I’m gay? 

What a wonderful question. First, let’s clear the big fear out of the room: liking prostate or anal stimulation does not say anything about your sexual orientation. Sexual orientation is about who you’re attracted to, not which nerve endings you enjoy. From a biological standpoint, the prostate is a highly innervated pleasure organ, sometimes called the male G-spot, and stimulation there can intensify orgasm regardless of whether someone is straight, bi, or gay. That’s anatomy, not identity.

So you can try saying something like, “Hey I love how comfortable we are exploring sexually together, I feel very safe with you and I hope you feel the same. I really want to explore prostate play because it feels amazing to me. It can be through the perineum (gooch), fingers, or toys.” You could also say, “I want to share something about my pleasure. I really enjoy prostate play. I know there’s a lot of negative talk about it, but it has nothing to do with who I like and everything to do with what I like on my body. Are you open to it?”

If she’s unfamiliar or hesitant, that’s also normal. Give her space to ask questions, learn, or say no. Even just introducing her to the idea that sex for you is not penis only is a big win. Ask about her comfort around exploring other erogenous zones too (nipples, neck, thighs, etc.). If she is open, start slow and collaborative. External touch, lots of lube, clear communication, and constant check-ins matter more than any specific act. Think of this as expanding your shared sexual map. 

I recently matched with a girl on one of the apps, and we have a plan to meet up. She gave me her Instagram, and I saw that she had an OnlyFans linked. Do I still go on the date if I think her being on the platform might be a dealbreaker?

No. Do not go on the date. If you think that being on the platform might be a deal breaker, please don’t put somebody through that. I know this isn’t exactly your intention because maybe you’re still figuring it out, but it really is so uncool to make somebody feel bad about who they are, especially after you’ve spent one-on-one time with them. I think a good rule is to not make somebody invest in the process of getting to know you when you already have a really good idea about where it’s going to go.

If you’re more on the fence than I’m guessing, you could also be honest and say something like, “I loved getting to connect with you. I think you’d be really cool to meet up with but I’m going to be honest, I have some personal hangups about the OnlyFans thing. It’s my thing, not yours. I am willing to hang and give it a shot, but I wanted to be up front about that.” That way, it gives her the agency to make the decision from there about how to spend her time.

There’s tons of advice out there on how women can feel sexier in their bodies, but as a guy I’m struggling. What can men do when they need a little boost of confidence?

I am really glad you asked this question because this struggle is far more common than most men realize. In my line of work I see how men experience significant body dissatisfaction, but are far less likely to talk about it or receive validation for it. Studies in body image psychology have found that men report anxiety about muscularity, size, aging, weight, and sexual performance, yet social norms discourage them from expressing vulnerability or asking for reassurance. As a result, men often receive a very narrow form of bodily affirmation, one that disproportionately centers on sexual performance or genitals rather than being desired as a whole body. Men often internalize the belief that they’re valued for what they do, not how they look, which can quietly erode sexual confidence over time. Hearing things like “your body is beautiful,” “I love your skin,” or “you look good naked” actually matters as they’re specific and sincere.

Here’s the harder but crucial part: external validation alone isn’t enough. Research on self-compassion and embodiment shows that people who practice internal affirmation experience more stable confidence than those who rely solely on partner feedback. You deserve to feel good in your body, not just competent in it. And sometimes the first person you need to hear that from is yourself.