Reaching Railed Rapid Fire: Shaving, Cheating, & Dating. Yum!

Let's answer some of your very smart & cool questions <3

Hi my lovely Railed Readers. You wrote in so many fantastic questions this week, I couldn’t bear to pick just one. So, let’s do some rapid fire (which really means me just answering them slightly faster than normal but still definitely dragging on).

K bye,

Mia

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I’m a virgin, but I’ve recently been offered opportunities to have sex! But I’ve been scared to go through with it because I am someone with a lot of body hair. Though I’m familiar with shaving and Nair, I’m completely lost on how to groom my more sensitive regions. What should I look like down there so my short term partners aren’t grossed out?

Hi there! What a valid question! First of all, you could have a giant bush or be a hairless cat and no one should be “grossed out.” Internalized misogyny loves to make us feel like vaginas are weird or even gross, so it’s crucial that we remind ourselves that our vaginas are beautiful, regardless of if it’s bare or full of hair. Have you ever noticed that there is not the same inherent pressure on men to be groomed a certain way? So let’s take some of the pressure off of ourselves!

Truly, there is no right way for you to look going into a sexual encounter. Personally, when a guy is fully shaved, I find that I can do my best work and really go for it during blowjob hour, and not be distracted by getting hair in my mouth. So, I typically choose to be hairless as well to offer the same experience when my partner is going down on me. For me, it’s less about aesthetics and more about logistics!

I’ve tried it all: bikini wax, Nair, and shaving. Personally, I find shaving to be the most comfortable and effective. Just be careful to not shave too often to avoid razor burn! When it comes to shaving, you want to go with the grain — for the vagina, that means going from the top down (from your belly button to your labia, basically). I hope this is helpful! Again, please feel empowered to show up in a way that feels sexy and good to you.

Had amazing sex with someone that I afterwards found out has a significant other. The sex was so good I want to go back but I know I shouldn’t, but part of me feels like it’s not my problem, it’s their decision at the end of the day. Would you ever knowingly hook up with someone in a relationship, particularly for incredible casual sex and zero emotional connection?

Oooo, that’s tricky. I totally understand what you’re saying: That person is the one in a committed relationship, not you. For me personally, I wouldn’t hook-up with them again because it’s what my therapist would call a “values clash.” I’m not comfortable with cheating, and I wouldn’t want to play any role in that. Of course, you didn’t know originally that the person was taken, but now that you do know, I would step away (unless they happen to be in an open relationship…? But it doesn’t sound like that’s the case). Incredible sex is so tempting, but I do really believe that you can find that again with someone else. And then, you’ll be able to fully enjoy it because it won’t be clouded by ethical questions.

I’m a newly single guy living in a big city. I don’t have the biggest social circle, either. Any advice for upping my dating game?

Hi reader! Congrats on a fresh start! I find that the best way to up your dating game is to genuinely have fun with it. If the apps are stressful or you’re not enjoying yourself, then what’s the point? If you have a positive, excited energy when re-entering the dating world, then the folks you date will sense that.

Having fun with dating will look different for everyone. For me, it means not being afraid to initiate sex on the first date, since that’s a really enjoyable part of dating for me. I’m also a huge fan of spontaneity, especially when dating or swiping can start to feel like a chore. To break out of the routine, I love sending chaotic or bold messages just to remind myself I have free will lol (i.e. “please tell me you’re a democrat”). Ask yourself what parts of dating you enjoy the most and find a way to maximize those moments!

Another huge way I’d recommend upping your dating game is to be really brave. Dating can be scary AF, and just going out with someone takes a lot of courage. But if you want to level up as a dater, you need to push yourself outside your comfort zone! Approach someone cute in public, offer to buy someone a drink at a bar, give a stranger a compliment — even if you feel scared, do it scared! I promise, the worst case scenario is NBD, and it will get easier every time.