Reaching Railed: Riding the D, complicated confessions, and how to know if you should breakup
I can't get on top! I'm the talent!
Welcome to Reaching Railed, my unfiltered, unprofessional advice column! Got your own question that you want answered? Write in here! Everything is anonymous, and nothing is TMI. Let’s dive into this week’s reader Qs!
My bf wants me to ride him but I’ve never done that before! I really want to but need some tips and tricks before I try.
I got you! But before diving into some tips and tricks, I want to be fully transparent: I don’t ~love~ being on top. For me, I think it’s a combination of things. I enjoy being submissive during sex, so *getting* fucked feels a bit more appealing to me than doing the *fucking*. I’m also a recovering people pleaser, and you may be like, WTF does that have to do with this, but let me explain: You know how people pleasers don’t like to be in charge of deciding what restaurant you eat at/what activity you do because they don’t want the responsibility on them if not everyone is having fun? I feel the same way about being on top. It’s hard for me to focus on my own pleasure because I instead find myself hyper-fixating on if the other person is enjoying it. Should I be going slower? Faster? Harder? I’m way more present when I’m not in charge.
Soooo my number one tip? DON’T BE LIKE ME! This is incorrect riding etiquette. Actually, it’s incorrect sex etiquette. As women, we have a duty during sex to ensure that we are enjoying ourselves, rather than focusing solely on pleasing the other person. While I’ve come a long way in my own journey to reclaim my sexual pleasure, I’ve still got a ways to go!
That being said, I have ridden my fair share of Ds, even if it was begrudgingly (not in a nonconsensual way, just in a he’s really tired so I guess I’ll tap in way), so even if it’s not my special talent, I have enough experiences under my belt to talk through the basic how-tos.
#1: It’s all in the grind. Once you have sat on top of said penis, grind away! Imagine his dick is that pillow or stuffed animal you would go to town on as a child, and your clit will probably love the feeling. Maybe you grind back and forth, side to side, or in a circular motion, mixing up the speed and angles based on what’s feeling good for you.
#2: Get on your feet! Try moving off of your knees and plant your feet, shifting into an up-and-down motion that mimics more classic penetration. Proceed with caution: This move honestly feels like mini squat pulses and will be a major upper thigh workout.
#3: Don’t be afraid to ask for help. If you’re wanting a little direction, ask him to grab your hips and guide them while you’re riding—if you want a sexy way to initiate this, just say “show me what you want,” and you can even place his hands on your sides. It’s a team effort!
#4: DO WHAT FEELS GOOD FOR YOU! If you are getting off and having fun, he will be too. And while it’s scary to be in control, we should all get more comfortable pursuing our own pleasure.
P.S. If you feel called, don’t be afraid to touch yourself while you’re riding! A big bonus of that position is easy clit access. Okay bye. Enjoy. Love u.
What is the best way to tell a partner that you’ve kissed or had sex with people who are your current friends?
“Just so you know, Ben and I used to hookup, but it ended three years ago and we decided to just be friends. I wanted to tell you since we may be in social settings with him, and I don’t want you to feel blindsided or like you didn’t have all the information. I see him strictly as a friend and am only interested in you. I’m happy to chat through this or answer any questions you may have!”
Key points to hit:
Offer this disclaimer before your partner meets the person
Share who, what, and how long ago — be completely honest, duh
Reassure your partner that they are your sole focus
Offer the opportunity for an open discussion
Make sure your side of the street is clean: Obviously don’t say all of this if you are not over that friend/don’t have a platonic relationship with them! If that’s the case, sort your shit out!
How do you know when to walk away from a relationship?? When do you know it's the right time?? I feel like it's a common thing my friends and I experience... that moment when you realize your boyfriend has stopped putting in effort. It feels like he always says "I'll do better," but how long is too long to wait around for something to change? How do I know I'm not asking for too much? It often feels like I'm asking for the bare minimum (planned dates for example).
Wow, I feel you. Thank you for writing in this super honest question. Unfortunately, I think the fact is that there’s no “right time” to walk away from a relationship. You could decide to stick it out with this partner or break it off tomorrow, and either could be the right call for you (and your friends in similar boats may have a different game plan that is right for them!). Everyone has a different tolerance for discomfort or conflict in relationships, and similarly, we all must decide for ourselves how much we are willing to sacrifice for the person we love.
So, I can’t tell you a specific moment when you know it’s time to walk away. But I can tell you that, if I had to take a guess, you aren’t asking for too much. If you have given your partner all the information—communicated to them what you want, how they can better support you, asked them to take you on more planned dates—then the ball is in his court to step up. He says “I’ll do better,” but if those words aren’t accompanied by actions, then there’s really no reason to believe he will do better in the future. People can change, but he might not. I think you need to ask yourself how you would feel if he didn’t.
TBH, the unfiltered part of me wants to tell you to break-up with your boyfriend. It’s okay to ask for more! To dream bigger for yourself! To want a partner who, I don’t know, puts in effort! The fact that you are writing in this question makes me think that you might agree with me. Of course, I don’t have all the information, and whatever you decide, I’ll support you! There’s no right or wrong answer here, so long as you’re happy.
3 good questions, 3 killer answers.
That last one, if she has to ask, it’s time to go, or it’s time for a serious talk.
Would add for the riding question to watch some porn, more of which involves riding than not because it’s better to film. That will illustrate the grinding/sliding you were talking about as well as the getting on her feet. Just don’t feel like you need to leave the high heels on in bed.
Depending on their respective anatomies, Rreverse Cowgirl might be more fun than Cowgirl. If she concentrates on getting herself off with his dick, guaranTEED he will like whatever she does and might even learn a move or two, or a spot whot gets her hot.
Another banger my friend!